r/cdstoriesgonewild

I’ve been crossdressing more and more in the last year or two and the craving for cock has increased with it.

I have a newfound confidence in approaching guys after a few sexual experiences and couldn’t stop thinking about what a guy at work could do to me.

He’s the complete opposite of me. I’m slim and average height, he’s big muscular and very tall. His biceps are pretty much the size of my thighs haha

We are close at work in general and I know he’s bisexual but prefers women and currently single somehow so I risked it and made a move.

He said my body is feminine enough to be tempted but would prefer to fuck girls because he loves squeezing boobs while fucking them so in the heat of the moment I asked what if I grew some boobs!

Well I now have little boobs but enough to finally tempt him and my god was it worth it.

I love my boobs now and the sex with him is mindblowing. I’m picked up and bounced on his cock like nothing, thrown around the bed and used as a complete toy and I love it.

Doggystyle with him holding my boobs actually made me cum from being fucked for the first time ever and I just love being his girly fuck toy now!

I hope it continues but I’m taking every meet with full appreciation.

I keep my profile hidden but I do have boob pics if anyone is interested :)

By now, I had sucked two cocks...I'd taken a break because of a purge, but it was the last few weeks in my college apartment, my roommates had already moved out, and if it wasn't now it was never...at least that's what I told myself. By now, I had downloaded Grindr and was browsing for any good candidates. After a few hours of browsing, I found a guy with the usual faceless profile. He had a decent body and a FAT cock. It was average length but fat as a soda can it seemed.

We flirted a bit, I sent him some sexy pics, and he asked when he could come fuck me. I told him how nervous I was going to be and asked if we could start with a blowjob through a gloryhole and then when he was ready to fuck me I'd go bend over for him. He thought the idea was sexy as hell. I told him to give me an hour to get ready and then come on over.

I shaved my body smooth and decided what to wear. Back then I was 6' and 135 lbs with a dainty little figure. I slipped into a skimpy flight attendant halloween costume, a blonde wig, and a red lace bodysuit underneath that had thigh high tights. I fixed my makeup complete with bright red lipstick to match the lingerie then put on a pair of 4" pumps.

After I was ready, I sent him my address and told him the door would be open. The whole time, I had a vibrating wand hitting my g-spot and sissy porn playing on my TV. I hung a sheet in the doorway of my bedroom with enough space for me to get on my knees under it and suck him...and I waited...

After an eternity, I heard the door creek open. My heart was racing 1000mph. I was so nervous, but I was also very excited. I heard every one of his foot steps echo through the apartment as he approached my door. Finally, I saw his feet approaching the door. He had already kicked his shoes off and was wearing pajama pants. His girthy cock was printing in the loose pants and the sight of it my my sissy mouth water.

I wasted no time grabbing his pants and pulling them down. I quickly wrapped my fingers around his cock. It was halfway hard, but already impressive and heavy in my hand. I stroked him for a few seconds then teased the head of his cock with my tongue. I felt a grin on my face as I was in sissy bliss with a big cock in hand. Finally, I slid his head into my mouth. I stroked him slowly as I worked my tongue around the head of his cock like a corkscrew. I did this until I felt his cock throbbing for me then I slowly slid my mouth all the way down his shaft.

I swallowed every inch of his cock over and over again. I gently massaged his balls as I sucked him. Then I switched it up and began sucking his balls as I stroked him. After I sucked his big, low hanging balls, I licked from the bottom of his balls to the tip of his cock and then shoved it right back down my throat. I left it firmly placed down my throat for a long time before finally coming up for air.

That did him in. "Go get on the bed" he moaned. I did exactly as I was told. We'd talked about this whole thing ahead of time. I went and pulled my dress up over my ass, leaving my vibrating wand in, and with a pack of condoms next to me. I called to him once I was ready. We set it up so we never had to have any face to face interaction. He was "straight" and I was...whatever I was and I just wanted to be used like a cheap whore.

I laid there head down, ass up for a moment, then I felt him behind me on the bed. The mattress moved as he crawled in bed behind me. I felt him grab the wand and fuck me with it slowly. It felt amazing to have somebody else using the toy on me. My moans were involuntary. They flowed out of me like never before. He toyed with my for a few minutes as I heard him stroke his cock. Then I heard him unwrap a condom.

He slowly slid the toy out of my tight little hole and quickly began to rub the head of his cock against me in its place. "mmmmmm yesssss...pleaseeee" I moaned as my body moved involuntarily. I was wiggling, moaning, and grasping at the sheets as he teased me by fucking between my ass. Finally, he pushed firmly against me...POP. The head of his cock ripped my virginity away from me as he stretched me wide open sliding his fat cock deep inside of me. I have no idea the things I screamed and moaned, but I know my neighbors surely heard every word.

"Holy shit...I'm not a virgin anymore...I'm a used slut now..." I thought to myself as I started to throw my ass back against him. It was a feeling like I'd never felt before. It was amazing, and his thrusts just kept getting more and more powerful. He fucked me deep and he fucked me faster and faster. My moans grew louder and my desire to be a cheap whore grew exponentially.

I had no idea that my tiny little girl cock was rubbing against the pillow I was bent over until it was too late. As he fucked my ass, I fucked the pillow. I was pouring precum all over it already, but I realized too late what was about to happen. He pounded my tight little hole over and over and I clamped down on his fat cock like a wet vice as I began to unload on my own pillow. I had the most powerful orgasm I had ever had. It lasted for an eternity, and by the time I was done, I was a puddle. Just laying there taking this strangers cock.

And then PNC kicked in and I realized...I was laying there..taking a stranger's cock...What was once pleasure turned to pain. What was once so hot turned into something I was guilty about. It wasn't in my nature to say anything, so I let him continue to pound me. Thankfully, my boipussy was tight enough he didn't last much longer. He gave me a few more thrusts then pulled out, ripped the condom off and busted a huge load all over my smooth ass. He moaned loudly as he did and the warm cum almost made me horny again.

Then I'm sure PNC got him too, because he was out of my bedroom before the cum even cooled down and I was deleted from his Grindr before he even got home. I laid there covered in cum for another few minutes debating what all of this meant...

This hookup happened quite some time ago but it was a very memorable one for me. I had a completely random day off in the middle of the week, a Wednesday or maybe Tuesday, and it was just the one day, so there wasn't a whole lot I could make plans for. So it started off like a normal day, went to the gym in the morning, and by late morning I was home, kind of bored and decided to log on to squirt (gay hookup site). I didn't expect to get any messages or see many guys online since it was the middle of a weekday, but then my inbox flashed and I had a message.

A nice looking older man said he needed to come use me during his lunch break, and he said he wasn't far away (I had my location on my profile and the site also showed your distance from other users). I was a little hesitant at first since he said he wanted to come over right away and I would have to get ready quickly. But, I was bored, didn't have any plans, and kind of horny so I gave him my address and told him I'd need 20 minutes to get ready.

I had never gotten into gurl mode that quickly in my life! I dashed to the shower for a quick shave of everything, and hopped out and rushed to trunk in my closet where I kept all of my fem clothing. I grabbed a pair of black lace cheeky panties that an ex-girlfriend left behind, it was a huge turn on for me knowing I would be wearing them for another man shortly. I then picked out some fishnet thigh highs, strappy heels, and a satin bustier with some sexy lace trim--it was perfect for holding my d cup breastforms nicely in place. Before I started getting dressed up I got one of my butt plugs, lubed it up good and eagerly got it in me, hoping that my guest would want to fuck me during our hookup, since we didn't actually discuss that in our short exchange online.

I sat down on the bed to put my stockings and heels on, followed by my lingerie and breastforms. I went back to my trunk for my makeup and I picked a long wavy brunette wig. I had just under 10 minutes for my makeup, normally I loved to savor the experience of standing in front of the mirror in my outfit and seeing the last bit of transforming into a CD slut, but this time I knew I had a better reward on the way. As a little touch of flair I went back to my trunk and grabbed a pair of long black opera gloves, I knew they'd feel good on his cock as I stroked him.

I went back to my computer to check my messages, he said he was on his way. I was already trembling with anticipation when I heard a motorcycle pull up in front of my house. I daintily ran (not easy in heels!) over to the front door and waited to greet him.

I opened the door for him as he got close and he didn't get a good look at me until I closed the door behind him, his jaw nearly hit the floor! But he quickly composed himself and said damn I looked good, he told me to do a little spin for him some he could see all of me, which I gladly did, wiggling my butt at him. I took his hand and walked him to the bedroom.

He was older than me, which I liked. A little shorter than me, and a stocky build. He sat on the edge of the bed and laid back while I quickly pulled him pants down. He was already semi hard and had a nicely sized thick cock. I kneeled in front of him and started stroking him and kissing its nice plump head. As I sucked him he said I was a good little cocksucker, and he said for me to get on the bed.

I got up and laid to his side and sucked him some more, his hand quickly found its way to grabbing and squeezing my ass in my ex's panties. He soon felt the jeweled end of my butt plug and gently but firmly pushed it into me as I sucked him, I couldn't help but moan in ecstasy at the feeling. As I sucked his rock hard cock faster and faster, he told me what a little slut I was and said how much I loved his cock in my mouth. Not wanting to stop, all I could do was moan for him that I loved his dirty talk.

At that point I was so turned on by him playing with my ass, I paused sucking him and reached over to the nightstand and got some lube and a condom, I told him I needed his cock in me and he responded I bet you do bitch, I put the condom on him and added some lube, then I got up and stood with my back to him.

I pulled my panties down to my knees and took my plug out, then guided his hard cock into my ass, it felt amazing feeling something bigger than my plug fill me up. I was reverse cowgirl on him, first I slid all the way down on him, and then slowly increased how quickly I bounced up and down him.

He said yeah you like this cock in your ass don't you, slut, in between my panting and moaning all I could get out was omg I love that hard cock in my ass. He started pumping faster and I knew he was going to cum soon. I made sure each time I slid down to get him as deep in me as I could, and then he held me by the waist all the way down on his cock and let out a loud groan as he came. I told him mmmm yes that's what I want as he gave me a few more thrusts, still holding me onto him.

Once he let go, I slowly rose up, pulled my panties back up, and went to the bathroom to get some wipes to clean up. He still laid on the bed, when I returned I kneeled in front of him to take the condom off, then I put his cock back in my mouth to get as much of the remaining cum as I could.

Once I was done I cleaned him with a wipe, he stood up and got dressed while I was still kneeling. He said he needed to get going so I walked him to the door. Before he left I told him I hope we could do it again sometime and put his hand on my ass for one last squeeze.

We did meet a few more times after that, and if you enjoyed this story I'll be glad to tell you more about how I was a good little cumslut for him.

This is a story of fiction.

I am a massage therapist and I had a pretty good practice till the economy took down turn. It has been getting thin recently. More and more regulars have stopped coming in. Taking up sports massage at running events to make ends meet, did not get me very far. To few and boring working with guys and girls alike at the end of the competition. It was usually 15 minutes or so per person and the tips where bad. I love to do deep work and make who I am working on so satisfied and that does not happen in 15 minutes. So, not really satisfied and not getting near enough money, something new was needed. It has to be exciting, too.

I decided to dress and massage for money. I posted on Reddit and to backpage websites. Dressing is something I really enjoy, and I look pretty good when I do. It's just when I'm by myself, sometimes for a whole weekend. I have gotten out of the house to a few places. I have good reviews on reddit. I keep my body shaved and I have a haircut that could be a man or women's depending on how I brush it. Now this was getting exciting.

So for the content, I was wearing a tight black nurses scrubs and red four inch high heels. Underneath was a garter and stockings. You could just make them out if you looked hard enough at the picture. It read "I do massage. Out call only. Guaranteed to finish strong. And it showed two pictures of me massaging some pretty fit clients, a woman and a man, nude on the table. With me bent over from behind and the other from the front. I had my hair up very made up, and smiling looking into the camera. My lips with very red lipstick and plenty of cleavage.

I got a message right away I was to come to his apartment.

I showed up, he is very nervous. A younger man, maybe thirty-one. Me dressed in in that black tight nurses scrubs, high heels and I am made up to the nines, with bright red lipstick and flawless makeup. Just like my pictures. I have salt and pepper hair in a nice bob that frames my face. He says, "you, you look nice, thank you for coming", but can barely get it out. He is so nervous and can barely move and talk. I walk in. He closes the door behind me. I set everything down and say, "can I help you out of these"? I slip close to him I strip him completely out of his sweats. Then, I pull a towel out of my bag and spread it out on his couch. "Here, sit here". As he complies. I go to set up my table. "Is here a good spot"? I feel him watching me; I put on a show. I set up my table, slow with long slow gestures with me bending over, and looking up and smiling. The late afternoon sun is coming through the window. It is so nice and comfortable in his apartment. I am really getting turned on. He puts his hand on his very stiff dick and begins to rub. No, no, no, I wag my finger at him, and he stops, "that's for me to do for you." Now I am getting a stiffy as I finish by putting the sheets on the table and turnning to him. He is slowly stroking his large dick, again. It really is turning me on. A larger and bigger around then mine, "You have a beautiful penis", I say, "I'm going to the kitchen for water". He knods the way. His eyes follow my every move. I come back with a warm wash cloth and remove a bottle of lube from my bag. I pull my top over my head showing my bra, and pull off my bottoms to reveal my garter and stockings. Standing in front of him with my legs apart and my fists on my hips, I said I would take care of that big hard on of yours. I kneel on the couch to his right side and reach out. I put my hand on his shoulder and he jumps. I can tell he is pretty fit and ask if he works out, he nods. I feel his chest. Going over both nipples and running my finger through his little bit of chest hair. Then down to his pubic hair. I rub his penis, that is pulsing with the back of my hand. I pick up the towel to wipe around and down his penis to clean it. Then squirting lube in my hand, I place it around his dick. "This should ease the tension you are feeling". "Relax now and breathe through your nose" I begin stroking as he concentrates on his breatheing. Saying, " put your head back. Stroking softly, his hands are at his sides. My hand moves up and down. I pause and scooch closer. My left hand on his shoulder started to rub around. My right hand movering up and down. I lean in and bring my lips closer to his penis and exhale and he let's out an "uugh". I kiss it. My hand is steady up and down, up and down. It's a long kiss with a little sucking. My tongue slips out of my mouth to his tip. He is so hard. Grasping with little more force, my hand quickins. It's tasting so good. My tongue licking around his head. This first orgasm is coming. I back away and intensely watch as I just stroke. I ick up is hand and place it on my lower back. He slides it down to my bum and squeezes and rubs it. I am becoming verbal and start making my oh and aaaahs now. My hand is moving up and down, and up and down, and up and down. My pace quickens. His hand squeezes hard on my bum and I moan. My dick is as hard as his and is slipping out of my panties. I scooce as close as I can to him, and put him in my mouth as he cums. He shoots into my mouth and keeps shooting filling me up and I start to swallow. I continue jacking him. He crys out, "I'm so sensitive, you need to stop". He is not done cummings; I don't stop. A few more strokes and a little head bob. Then I freeze and squeeze it. He throbs in my hand. I take my mouth off. "How is that to break the tension", I ask? I stand up and get a hot towel to clean him up. I come back and kneel next to him again. I clean his penis and around my lips. I take a drink of water and I offer it to him. I bennd over and take his limp penis in my mouth and suck it into my mouth and tongue his pee hole. Then stop and stand up. I offer my hand and pull him up and led him to the table.

This is the true story of my first real sissy experience. 
One night I was rolling on a little molly. I was cleaning with enemas and looking on Grindr for some fantasy material. Someone had tapped my profile with the username, “letmeeaturass.” I messaged him and invited him over! I paid him $20 for an uber! I dressed up in a cute cute cute cute cute outfit. Muted pink sports bra with the false breasts inserted underneath my crop top bold pink polo midriff shirt. I want to get my bellybutton pierced. Then I had on that adorable flouncy pink skirt with the ruffles that felt so nice to wear. Beneath that I had on a bright pink Victoria’s secret thong that framed my ass perfectly. Underneath the thong I was wearing this amazing black garter belt and stocking combo that made me feel so sexy. It’s important to put the stockings underneath the underwear so it’s easier to take them off. I just moved mine to the side. I also put in my smallest metal butt plug with the bright pink jeweled base. 

I put on a little bit of makeup- just some sparkly amber eyeshadow and pink lipstick. A quick spritz of perfume and I was feeling confident. Then I put on my heart shaped collar and pink wig. I quickly set the mood by lighting candles and putting on a sexy playlist. I took two pillows and placed them near my door. I texted the Grindr guy to just knock on the door and I would leave it unlocked so he could walk in and immediately eat my ass. I assumed the position of face down, ass up on the pillows and it felt right. The excitement I felt while I was waiting was genuinely electric. My entire body was buzzing with energy and I was nervous, excited, scared, incredulous, unsure, and incredibly turned on. My lust levels were high. My horniness was approaching maximum levels. The sexual excitement was over 9000. 

Finally the knock at the door came. I called out, “Come in,” and the door opened. He came in, closed the door, slowly lifted my skirt up, pulled my thong to the side, took out my buttplug and then began to passionately eat my ass. It was amazing. I felt like a complete and total slut. His tongue was doing wonders for me as I moaned and writhed under his oral assault. I was completely overwhelmed by pleasure and came in powerful waves of ecstasy. 
Eventually my hips buckled and I collapsed to the floor in pure bliss. I flipped over and finally looked at my male visitor. I told him it was amazing and would he please follow me to the bedroom for more? We briefly exchanged names and pleasantries.

I instructed him to bring the candles to the bedroom and then I sat on his face. It was a dream come true. I gyrated and moaned and enjoyed every minute of it. It was so erotic and naughty to be dressed up like a slut and having my ass passionately eaten! I could have stayed there forever! I came again and the shaking from my legs was so extreme that I had to slide off and lay beside him on the bed. 

My memory of the entire encounter is slightly hazy because I was drinking a little bit that day and I had taken a good amount of MDMA also. But I think what happened next is that I gestured to my nightstand that was occupied with my sizable dildo collection. I requested he pick one and he selected my lovely 7” clear boy and proceeded to slowly penetrate me with it. My bliss reached previously uncharted territories. I laid on my back and pulled my stocking-clad legs up high into the air. He gently slid the toy in and out of me, I bucked my hips wantonly to activate my deepest pleasure buttons and I lost myself in the passionate throes of lust. 

At some point I asked him to switch to my black and red alien dildo and said some silly high shit like, “take me to your leader” and he still went along with it! We had crazy amounts of fun with the toys, I retrieved my wand vibrator and was using it too. I should also add that I had been wearing my pink chastity cage this entire time! That added to the overall feeling of being excited by the ‘degenerate’ nature of that evening’s events. 

I love being an adult that buys fun toys. I brought out my lovense and made him hold it while I opened the app and demonstrated how to control the vibration. He may be dumb enough to eat a stranger's raw butt, but he caught on quickly with the concept of teledildonics. I invited him to play with me while I rolled us a joint and really exaggerated my moaning. I am incredibly thrilled by the advent of teledildonics and I think the interface of computers and robotics and pleasure and software and orgasms is incredibly hot. I really want to make a robot cum. I’m adding that to my bucket list. Lol 

Ok anyway we’re smoking some weed, I did a quick outfit change into that little orange bodysuit that is so fucking sexy. I was dancing around a little bit, bending over and asking to be spanked, it was insane. I didn’t tell him that I was rolling on molly but I think he might have possibly been able to tell based on how much I was grinding my fucking teeth lol. I thought that I was playing it cool but in reality I was probably absolutely unhinged and buzzing and embracing the situation. We smoked a little bit on my balcony and I asked him if I could grind my ass on his crotch. I really loved dancing on him, bending over, feeling his cock get hard and grinding on his dick. 

We’re back in the bedroom and I tell him that I want to ride his face again, “but this time take your pants off.” I went into the bathroom to apply a new coat of pink lipstick and give myself a quick pep talk. I stared at myself in the mirror and was overwhelmed with incredible feelings of love and lust. I felt desirable. It was a powerful feeling. 

Then I went back in and rode his face some more. Josh’s grindr profile was called, “letmeeaturass” and so I let him. I was loving the way his tongue was exploring my sacred depths and vocalizing my pleasure like a true slut. It was amazing and my hands were tightly grasping his strong legs. He had told me at some point that he was a roofer and I appreciated his working-man aesthetics. My hands played across his body and I adjusted my posture on his face while I caressed him higher and higher. I finally touched his penis. It was… great. I enjoyed it. I grabbed him, stroked him, played with him, squeezed him, and he grew hard and expanded in my hands. It was intoxicating, it was magical. I could hear him groan in appreciation as his organ grew. I leaned down and gave it a very slow kiss on the shaft. It was a very nice size. Not small, it was bigger than mine, but not unmanageable. I was so turned on I had to take another break and lay down beside him again. 

I lay next to him, panting and trying to recover my breath after my analingus-induced orgasms. I was feeling incredibly grateful as my left hand lazily explored Josh’s body next to me on my mattress. My hand eventually made its way to his pubic region as I idly stared off into the distance. My thoughts were rapid and scattered as I languidly stroked his hard cock. What would xyz think if they could see me now? I rubbed and squeezed his balls. Am I going to regret this? I pulled back his foreskin and relished a satisfying drop of pre-cum. What are you doing Greg? I gently jacked him off. 

There were so many thoughts going through my head and I struggled to align myself. “I am breathing in, and I know that I am breathing in. I am breathing out, and I know that I am breathing out.” I silently repeat this mantra as my heart gradually regains a normal rhythm and my breath slows. I realize that my hand is still idly stroking this man’s cock and I start to turn my mind to what to do next. He has given me so much pleasure, I should return the favor. 

I sit up off the bed and take a few pumps of lube in my right hand and apply it to his naked cock. What a seminal moment! I begin to stroke him using my years of practice as a cock-owner. I know what feels good when I grasp him and apply different pressure and swirl my fist and tapdance my fingers along his shaft and tell him how amazing his dick is and and and and and and and and! 

I’m flustered and overwhelmed again and lay back to catch my breath once more. Can he tell how fucking hard I’m rolling? My teeth are grinding audibly and I’m sighing in pleasure constantly. I am also allowing myself to feel a lot of conflicting emotions all at once and trying to quietly contain my powerful buzzing inside. Eventually I can’t hold it and I decide to use an incredibly powerful technique. I read about this in an important text and it has stuck with me due to its revolutionary teaching. I allowed myself to say out loud the feelings that I was experiencing! I know. It is an insane proposition, but wow it feels so good. I spoke out loud that I was feeling confused, excited, guilty, high and definitely horny. And I was thinking about asking Josh to reach over into the bedside night stand and to grab a condom from the top drawer and then put it on his cock so I could sit on it. I have never said anything remotely similar to those words before so it was truly a unique experience that I had never even imagined that I would have during my time on planet Earth. But I had said it and the words hung heavy in the air. But only for a moment before Josh lunged for the night stand. I grabbed his arm and asked him to wait because I said that I was only thinking about saying that! To his immense credit, he stopped and let me stroke his cock a little longer while I pondered and rolled face. I really actually lucked out by snagging this chill dude for a night. 
You can probably guess what happened next. 

I straddled him in reverse cowgirl and spread my ass open. I twerked to the best of my ability and rubbed his cock on my ass to make him rock hard. He warned me that it would make him cum. I said yes please, that’s the idea. He put the condom on, I applied some lube and then put him in. It was heavenly. I rode him hard, I rode him fast and it was fucking incredible. His dick was so hot inside of me, I couldn’t hold anything back. I was leaning forward and bouncing my cute pilates ass on him as best as I could. Then I leaned back and really increased the tempo while he hit me deep in my prostate. 

He came. I came.

Yes. It was tremendous. 

I put my full weight onto his dick and ground it around in a circular motion and milked every last drop of cum out of him that I could. I did it. I felt accomplished, I felt satisfied and I felt great. I told him to spoon me, we hung out a bit and talked some. We smoked a little more weed, and I changed into another cute girly outfit. He fixed my sink also lol. 

Then I told him it was time to go. He left and that was that. 

Hope to try it again soon. 

This is a true story that I have posted before. It happened two years ago.

I was traveling out of state for work. It wasn't too far and so my job let me rent a car and drive. This was perfect because it allowed me to bring all my girly items. I planned to experiment with trying makeup on this trip for the first time and I was very excited.

I spent my drive messing about on Grindr and teasing men along my journey with my CD pics.

I got to my hotel around mid-afternoon and quickly unpacked all my girly clothes and items. Panties, bras, lingerie, wigs, leggings, toys and makeup. I was so excited. I had a work dinner that first evening but knew I would get back to my room asap in order to maximize my time as Katy.

After dinner I went to my room and immediately got in the shower. I shaved myself as smooth as possible and then watched a couple makeup tutorials. I was keeping it simple. Foundation, concealer, mascara, eyeliner, eye shadow and lip gloss. I felt super pretty and didn't look like a total clown for it being my first time. I even brought some nail polish and painted my nails a bright red to match my red lip gloss.

For clothes I put on black stockings and a red lingerie set. The lingerie was a two piece set. Lace. The bottoms had garters built in that I attached to my stockings. I added a black lace robe and topped the look with a red haired wig. I looked hot!

I opened Grindr and posted some updated photos. Then I put my jeweled plug in my ass and lied on the bed. I was immediately inundated with messages. After sifting out the blank profiles, pic collectors and weirdos I started talking to a local guy a bit younger than me. He was keen on coming over but I was very nervous. I had never done anything with a guy while dressed up. I hesitated. Backed out. But eventually I built the courage and sent him my hotel and room number. I was so nervous, but very excited.

I messaged him before he arrived go see what he wanted as far as room setup. He asked for no lights but the tv on. I left the door unlocked and waited for him show up. When he got to my room he knocked and entered. I greeted him in my most feminine voice and he immediately took off his shorts and got on the bed with his cock out. His cock was perfect. About 5.5 inches. Cut. Not too thick. Delicious 😋 🤤.

I assumed my position between his legs and brought face to his beautiful cock. I could smell the slight scent of sweat. Just enough to make my mouth water. I brought my mouth to the head of his cock and began by kissing the tip. The cock began to spring to life at the touch of my lips. After a few kisses I started to swirl my tongue around the tip of his cock. He began to moan and called me a good girl. Which of course made me want to please him even more. I took the cock into my mouth and slowly began working up and down. I was bobbing on his cock and starting to build a rhythm when he put his hand on the back of my wigged head. I knew what was coming. He pushed my head down on his cock, commanding me to deep throat his manly cock. I began to gag and could feel tears in my eyes and my makeup running. I reluctantly pulled his cock from my mouth to get a breath and gather myself. His cock was glistening with my spit and his own precum.

I asked him if I could get on my knees and he stand in front of me to finish the job. He obliged. I put a pillow on the floor and got on my knees like the hungry slut I am. I began working my mouth up and down his shaft again. He told me he was getting close. I told him I wanted to swallow his cum. I used my hand to jerk him a few times and then returned his cock to my mouth. Another couple swirls of my tongue and he told me he was going to cum. I grabbed his ass cheeks and held his cock in my mouth while he released rope and rope of thick, warm cum into my mouth and down my throat. He removed his cock from my mouth but I cleaned up any remaining cum.

He put his shorts back on and left.

I got in bed and started messaging more guys on Grindr. I chatted and sexted and recounted my tale until I finally released my own ropes of cum all over my belly. I used my finger to scoop as much of my own cum as I could and swallowed it as well.

I had met a guy on Craigslist when it was a thing looking for a crossdresser. we were both in the military and agreed to meet on the beach on base. He was a staff NCO so he asked me to meet him at the cabana on the staff NCO beach.

I shaved smooth and slipped on my red two piece bikini. Then slipped on my black lace cover up before putting on sweat pants and sweatshirt. I packed my curly red wig and lipstick, hopped in my car and drove to the beach.

I was so nervous because we were doing this in public on base and the last thing I wanted is getting caught by military police. After a 15 minute drive from my barracks I pulled into the parking lot. I applied my lipstick, fixed my wig, and slipped off my sweats. I took a deep breath and stepped out into the night. I adjusted my wig and made my way to the cabana.

As I got closer I could see the burning end of a cigarette on the cabana and hopped that was my guy. I swallowed hard and approached him. I said hi I’m Kelly we talked online. He flicked his cigarette and turned to me greeting me.

He pulled me in tight hugging me before taking my face into his hand and kissing me deeply. We swirled our tongues while his other hand explored my body. I began to relax and get into it sliding my hand into his swim shorts finding his hard cock. I began stroking him while the front of my bikini bottoms became wet with precum.

He asked if I wanted to go for a swim and pulled my cover up off and took me by the hand. Leading me to the water he stopped at the waters edge removing his shorts before pulling me into the water. the cold water hit my smooth skin making me shiver as we waded out deeper.

Once we made it to chest level he pulled me close and we began kissing again. He grabbed my ass with both hands pulling me up and I wrapped my legs around his waist. I could feel his cock pressing against my ass and felt him move my bikini to the side. He whispered in my ear asking if his little slut was ready for his cock. I softly said yes and reached back guiding his cock to my waiting boy pussy. When he was lined up I slowly lowered myself onto his cock. I felt the head of his cock push inside me and as I slide to the base I moaned softly. I wrapped my hands around his neck as I slid up and down his cock riding him slowly.

My lust was growing and wanted to fuck him harder so I slide off his cock taking it in my hand and making our way out of the water. I had him lay down, kicked off my bottoms, and straddled him. Hovering over his cock I kissed him and popped his cock back into my ass. Moaning into his mouth I leaned back bouncing on his cock while I played with my nipples.

I increased my speed feeling my orgasim build I began moaning loudly slamming harder onto his cock burying it deeper inside me. The sound of my moans, his, the way his cock was filling me up, and the waves crashing on the beach was to much and my little cock exploded shooting rope after rope into the air onto his stomach. My body began to shake, my moans grew softer, body grew weak, and collapsed onto him.

He kissed me and rolled me onto my back keeping his cock inside me. He pushed my legs to my chest and fucked me hard as I lay there helplessly moaning like a little slut. His thighs and balls smacked against my ass with every thrust.

His speed and intensity grew faster and harder. I knew he was close. I moaned for him to breed his sissy slut. He grunted and burried his cock deep inside me. I could feel his cock pulse inside me and his hot cum fill my ass. While he empties his cock inside me he leans forward and kisses me passionately.

When I was full he slipped out of me and helped me up. I picked up my bottoms and slipped them on feeling his cum leak into my bikini bottoms. We walked back to the cabana where I collected my cover up and he told me about a gay club an hour away he goes to that has crossdressers like me. He said he wanted to take me as his date one weekend to which of course I agreed. But was nervous as I’ve never gone out in public like that. We kissed one more time before going our separate ways. My little cock began growing again feeling his cum on my butt and the sand thinking about the time I just had.

Back at the barracks I took off my wig, wiped off my lipstick, put back on my sweats, and made my way back to my room. In my room I slipped off my sweats and slept in my bikini. It was one of the best nights.

Hello reddit! Kaz here

A little update! Im still living with my mom but I might be moving out soon, she has dated but nothing serious until about 4 months ago, my mom is 46 and she is dating this much younger guy who is 31, he is nice and they seem to get along. They met at work and started dating after knocking each other for a while, I mention this because ever since she started dating him, she has been going out alot more like during the week at night even which she never did before. It has been perfect for me because I get the house alone alot since they stay at his place most of the time.

As for me. I stopped lying to myself and I haven't dated a girl in a long while, Im committed to serving men, I been very active in Grindr and kik hookup groups.

Also I frequent alot an adult theater that's 3 blocks away from my house. About 8 months ago I discovered it through a grindr hook up that the sex store has an adult theater as well as private sections for hook ups in the back and its only $15 for an all day entrance which is super cheap.

After finding about this place, I go about 3 times a month at least, I dressed up sexy and service men there, there's very few girls ever but alot of guys! Most curious, some knowing exactly what they are looking for but I always get fucked multiple times when I go so its always fun!

(This part is to add context about some things that have happen since I moved here with my mom, you can skip this part ☺️

So one of the things that happen is one day me and my mom we where watching this Colombian novela, we watched when i was young and is super funny, its called la costeña y el cachaco, we where using her computer and watching the episodes in YouTube, she got a call from her boyfriend and she walked away on the phone, I stopped the video and with no intention started going through the history, just got curious and I never have access to her computer since I have mine so it just happen, my mom to me at least has always acted very traditional, we dont talk about sex or any of those topics and she seems like the boring kind in a good way, so I was surprise to see her history, alot of lesbian porn, orgies, gangbangs but what really caught my attention was a good amount of sissy porn, mainly dom stuff and also alot of men on men gay sex which really surprised me, also not long ago. I was looking for baterries for my remote and my mom always kepts batteries in her second bed stand drawer, for my surprise when I went to check, she had a pretty big and thick green hulk color strapon, idk what my mom has been up too with her new boyfriend but wow, my own mom to my surprise might be a bit of freak but that was that)

Back to the story...

It was a Thusday night, I had posted in the kik groups I use and also on grindr that I would be at the theater being a free use slut, I usually spend there 3-5 hours and I see alot of the same people, some I already know me and have used me before so its a familiar place.

I was a normal day I had been there already about 2 hours, it was a pretty slow day, not many people where there as usual for a Thursday night but I had fun with 2 different daddy's already so it was a goodnight.

Right before I was getting ready to head out since there was no movement, I heard a group of people come in, I could heard 2 girls but they where talking very low and 2 more of guys that where being extra loud, I open the curtain to my booth and got in all fours with my ass and locked clitty pointing to the door as I always do, I dont think there was anyone else in any of the other booths and I could hear them opening booth curtains to check inside until they got to my door, one of them said what do we have here, coming in and slapping my ass hard, I just wiggled my ass to him asking for more until I heard my moms boyfriend voice say to someone, told you this place is crazy, we found one! I always wear a mask to cover my face at the adult teather like in my profile Pic so they couldn't see my whole face.

I entered panic mode once I heard my mom voice replied to him " She looks nice while giggling, I froze and just stayed there quiet while they felt me up, I know my mom spanked me and cuffed my clitty at least once, the male friend kept asking me my name and calling me a slut but I just keep wiggling and nodding, he then said, Im a fuck her and my mom, female friend and my moms boyfriend told him to do it and they wanted to watch, my clitty started licking so hard, I was about to get fucked in front of my mom and her friends, he asked my moms boyfriend if he had a condom on him, but he didnt and to be honest I would of let him hit it raw, but I couldn't say anything, they talked about getting some at the the sex shop up front but they didn't come back, idk what happen but the whole experience was crazy! My clitty starts leaking everytike I remember it, I wish I would of had the guts to turn around and remove my mask, I had such pretty makeup on and I was looking hot! Idk what their reaction would of been or where that could of led to but I didnt do it and I dont think this would happen again, or maybe it will, I still go to the teather and dont plan on stop going.

Went to apartment store primark today. For the first time buying clothes I bought cute clothes. A bra and panty set, lacetop stockings, cute pj's, and a cute pair of shoes. Walked around for about an hour, looking at all the beautiful clothes. Then, I just filled my basket and went to the self-service . Nobody batted an eyelid. I've never been so nervous I was shaking. Young wo.an on the next check-out gave me a big smile and a wink when she saw what I was buying !!! I'm on a high the adrenaline 💖

We are a group of 6 from College going on a trip to Goa. Out of the 6 , there’s one couple and rest of us are single.

Me \[ 26M\] and my friend \[26F\] are secretly fucking eachother without telling friends , as we don’t want to disturb our group dynamic.
So, we took an Airbnb . It’s been a while since we fucked each other as it’s kinda hard to do this without our friends doubting us . This sneaky sex really gets us going , maybe that’s why we are keeping it a secret . So we were really waiting for this trip to fuck our brains out.

After a day full of sight seeing , All of us started drinking in the hall in the evening and got really high.
She was wearing a black crop top and looked really hot . She leaned towards me(she’s got great boobs) and said “ I wanna see you in a Bikini “
I laughed and took it lightly .

Later that night we went to beach , she left for like 15 mins saying she needs to do some shopping
and then we all came back to room and started drinking again in the hall . She left the group saying she’s tired and went into the room .
Then I got a text from her , saying “I have a surprise for you 😈 “ This sent me a chill down my spine as she’s really freaky in sex .

So after 10mins or so I also left the group saying I was sleepy and went into her room.
As soon as I went inside the room , she pushed me on the bed gave a passionate kiss .
She was wearing a sexy black satin babydoll showing plenty of cleavage.
She gave me a cover from her shopping bag and told me to wear it in front of her.
I opened it and it was a bikini ( white n blue , it was soo hot)

I was already damn hard. I stripped my normal clothes , took the bikini . She saw I was struggling to tie behind my back , so she came over to me tied it. ( it felt soo submissive). So there I was standing in a two peice bikini for the first time in front of my dom. We started making out and
She took my dick out the thong front the side and started stroking it .I was literally in heaven feeling her hand on my dick .

Suddenly one of our friend knocked our door . She panicked and went to get the door as we forgot to lock it .
N I just covered myself with the blanket and faked as if I was already asleep . ( I was just wearing bikini , n nothing else )
One of our friend came to use the rest room and after he left , she locked the door this time😅.i was still on the bed fake sleeping and she started sucking my dick .

After few mins she said let’s fuck in the balcony . ( This Airbnb was in a big gated community and the room had big balcony with transparent glass doors) . It was around 3am.
I was scared af . But being that horny and as my dom gf asked me ,I went ahead .
Now, both of us dressed up slutty and we started making out there . I took her boobs out of her dress and started sucking on them .
Then she lifted her dress and bend over , I was so excited to see her ass and me being dressed jn bikini .

I slid my dick out of the thong and started to fuck her in doggy position.
It was soo hot and scary at the same time .
Then we went inside the room ( the balcony was still open ) she came over me, choked me a bit and called me a slut for dressing up like that and we fucked in cowgirl position (our favourite)
Seeing her boobs move with each thrust made me even horny and we both had an intense orgasm .
We cleaned up and slept in the same outfits.
(We are new to this Femdom and cross dressing
Suggest us new ideas to try )

Riley woke up in a haze to a half-empty bed. He had slept in later than usual. Not by a lot, but his morning routine had been fixed for so long that seeing the sun at a different point in the sky was disorienting by itself.

The extra space on the queen-size mattress also threw him off, but not as much as realizing that he was naked under the sheets. He couldn’t remember the last time he’d slept completely naked. But then, he also couldn’t remember much about the night before. He couldn’t quite put his finger on when he crawled into bed, what he was up to beforehand, and whether June was there at the time. It’s not that he always went to bed and woke up at the exact same time as his fiancée. But he usually knew when they were on different schedules, whether that was due to his work hours or her PhD studies.

The bedroom was silent except for the sounds that seeped in through the closed window and the door. Intermixed with the sounds of traffic from the street three floors below, Riley could just barely make out June’s muted voice. He couldn’t hear what she was saying, but her tone and cadence suggested a casual conversation with an acquaintance. There wasn’t a second voice, just gaps when June was silent. That suggested June was on a phone call, which led Riley to recall that her fellow PhD candidate and best friend Becky had gone to Paris for the summer. He calculated the time zone conversion from 7:30am in Portland to 4:30pmin Paris, and the sequence of events that led him to wake up later than usual to an empty bed suddenly fell into place.

He rolled out of bed, feeling an odd tingle up and down his legs as he did. He chalked it up to his bare skin sliding over their silk sheets without the usual intermediary of his flannel pajamas. Why his pants were missing remained a mystery. He planted his feet on the shag carpet of their bedroom and felt another odd sensation. This time, it was his calf muscles, which felt unexpectedly (almost painfully) stretched by lying flat on the ground. He’d woken up to a Charley horse in his legs before. This was not that. This was another morning mystery.

He opened the top drawer of his dresser and absent-mindedly pulled out the first pair of underwear with one hand while the other rubbed the sleep out of his eyes. He slipped his feet in one leg at a time, pulled the underwear into place, and switched drawers to grab a pair of socks. This time, he noticed that his hand landed on something unexpected. Where he expected to find a rolled-up pair of blue dress socks, his left hand instead grabbed a folded-up bunch of beige nylon. Not a pair of socks but pantyhose. He paused and scanned the rest of the drawer, only to find that it was filled almost entirely with hosiery—pantyhose, tights, and stockings. 

He was thrown by what he saw, but not quite because of what he saw. What threw him off is that it didn’t surprise him. He had the odd sensation that the drawer had exactly what it should, that whatever he used to find there—his dress socks, casual socks, and gym socks—had been moved. But he couldn’t recall where. We must have reorganized everything, he thought to himself. But when? Were we high? Did I get black-out drunk last night, right around the time we decided to switch dressers?

He didn’t feel hungover, and he didn’t see any empty bottles or roaches on the bedside tables.

Before he could test this theory further by checking June’s dresser on the other side of their bedroom, he felt a compulsion, an impulse. His left hand grabbed hold of the pantyhose and lifted them up from the drawer. The two legs unfurled before him, and he could tell immediately that these were not June’s. He hadn’t committed her size to memory, but he could tell that the legs were far too long for her 5’4” frame. When he held the dangling pair against his own waist, though, the length appeared to be just right. 

A word suddenly manifested in his head. It flashed like a theater marquee, like a billboard in his mind, and it wouldn’t go away.

“Mine.”

No, he thought, this isn’t mine. But that thought was overwhelmed by the sheer force of the insistent word.

“Mine.”

The word had a force that compelled his right hand to grab the opposite end of the waistband and compelled his feet to shift over to the empty bed. He sat down, feeling almost like his muscles and joints were on rails. The movements of his hands were mindless, driven by pure muscle memory like tying his shoelaces or signing his name. 

His hands rolled up one leg of the pantyhose until he reached the reinforced toe. Then his leg rose to position for his foot to enter and be encased. He could only pause the motion of his body through conscious will. 

It wasn’t the first time he’d put on a pair of hosiery like this. He’d tried it once in high school, acting on a dare from his girlfriend for her amusement. He was clumsy and yanked them up like gym socks, tearing a run from top to bottom that made her girlfriend howl and hit him in a fake rage.

This time, his hands weren’t clumsy. They were delicate and intentional. The instant he stopped willing his hands to stop, they continued to roll the first leg up, gliding over his smooth, hairless leg, before moving to the second and repeating the process.

Smooth. Hairless. Legs. Another mystery!

In a flash, the hose were rolled up to his thighs, and without thinking, he stood up to pull the waistband over his underwear. It happened so fast and effortlessly that he barely had time to process his latest discovery. That’s why the sheets felt different, he realized. 

He sat back down and ran his hands up and down over his nylon-encased legs as he tried to pinpoint exactly when and why he (or someone else?) had shaved his legs. The feeling was electric. He couldn’t recall anything like it. Every nerve ending from his hip to his ankle responded to his hands rubbing over them, coming alive to their touch.

He was addicted immediately. He couldn’t stop sliding his hands up and down and back again. The sensation captured him so much that he didn’t hear June’s cadence switch. He didn’t notice that her conversation was winding down. He didn’t catch the footfalls or the sound of her hand on the bedroom doorknob.

“Hey, babe!” 

June froze at the doorstep and locked eyes on Riley, who looked up at her like a deer right before a collision.

“Hi!” His voice snapped out of him like a triggered mousetrap.

She studied his eyes and his pose, his two hands frozen above his left knee. 

“Everything okay?”

He didn’t know how to answer. One part of his brain wanted to say that nothing about the morning had been “okay.” That voice was overruled by the rest of his brain, which—much to his surprise and confusion—felt very much “okay” with the situation despite it all.

He settled on a response that felt objectively true, even if his mind debated exactly why it was so: “I’m sure this looks strange.” 

June nodded with a smirk. “Yeah, you could say that.”

“I found, um, this,” he said with his hands open to display his legs, “in my dresser, and it just sort of happened.”

“Yeah, okay,” she replied flatly, leaving Riley to wonder if she even noticed that her fiancé was sitting on their bed wearing nothing but a pair of pantyhose over shaved legs.

“It just felt…” He paused to consider the right word. Like the word “Mine”, one word quickly manifested itself and took over his brain. “Natural. It felt natural.”

“Well …,” June said and paused, causing a sudden panic in Riley that she might say nothing more but instead just pack up and leave him. But her pause was brief, and the next word that came out of her mouth was a softly spoken “yeah.”

“Yeah?”, he asked, more baffled than relieved by her answer and her tone.

He could see her processing. He’d seen that furrowed brow on her face plenty of times before, usually hovering over a keyboard or a table full of notes and research. It was the focused intensity of her PhD-powered brain working something out. 

Her face and voice shifted to a tenor he’d seen come out of her whenever she had to teach an undergraduate course or mentor a younger student. She sat down next to him, laid a hand on his nylon-encased thigh, looked into his eyes with cool confidence, and said, “Tell me what’s been happening.”

“Well…” Riley walked through the last half hour of the morning, beat by beat. He spoke with the anxious precision of a student in the principal’s office. He didn’t think he’d done anything wrong. Not exactly. But he didn’t understand what was happening, and so his guard was up. “And then you came in.”

“Does anything else feel odd or unusual this morning?”

Now it was his turn to furrow his brow. That question implied that what he’d just described—waking up naked with short-term amnesia and crossdressing on autopilot—wasn’t enough.  That all of that might just be the tip of some even crazier iceberg he had yet to hit.

“I guess that my ankles also feel weird. I think I just slept on them wrong.”

“Like a cramp? A Charley horse?”

“Like that, but also no, not like that. My calves just feel tense.”

“All the time?

“When I stand up.”

“Show me.”

Now, Riley felt like a laboratory test subject. He suddenly stopped seeing June as his fiancée and started to see her as a lab technician. He stood up as requested and planted his feet flat on the ground.

June looked down with interest, looked back up at Riley, shrugged, and said, “Well, sure.”

“Sure, what!??” The more June seemed nonplussed, the more confused he grew.

“That’s going to happen to your legs after—wait just a second…” June abruptly shifted gears mid-sentence, suddenly stood up, and walked down the hall. Riley’s mind felt unmoored to a brand-new degree. He could feel reality shifting around him, and he began to wonder if he even knew where he was, or if he had maybe slipped into an alternate universe.

June returned to the room holding a pair of blue closed-toe block heels. She set them down in front of Riley, with the heels facing him and the toes facing away. She held out her hands to present them to him as if no further explanation was needed.

“You want me to—” She immediately nodded in response, with her eyes opened wide as if the answer was obvious. He performatively popped his eyebrow and vocalized a sigh as if to say, Well, why not? The day’s been weird enough already, so might as well keep going.

His feet slipped easily into the shoes. The size was just right, and the insides had noticeably molded to the specific shape of his feet. The lift of the heels took away the discomfort in his calves, and to his surprise, he felt perfectly balanced and (that word again) natural.

“Better?”

“Yeah.” He was genuinely surprised, but again, mostly by how little surprised the better part of his body and mind felt.

“When you’re in heels most of the time, the calves start to adjust until standing and walking without heels will actually feel uncomfortable.”

Her explanation made perfect sense. And yet, simultaneously, he felt like a bomb had just exploded in the room.

“Most of the time!?”

June’s eyes opened wide, and she mouthed a silent “Wow!” Her brow furrowed again as her mind returned to processing mode. She disappeared from the room briefly to grab a notepad and pen from the study room next door.

“Okay, sit down. We need to dig into this.” Riley did as she asked, sitting next to her on the bed as she scribbled into her notepad. He was equal parts nervous and excited, feeding off of the buzz radiating all around her.

“So,” she said with the tone of a Special Announcement, “we’ve been engaged in an experiment. You and I. With your full consent, I have been practicing hypnosis on you as research for my thesis.”

“Um, okay.” Every word she spoke had a ring of truth to it, but nothing she said conjured any specific memories in his head. She must have sensed his reservation because she disappeared again into the other room to grab an iPad.

“Here,” she said, pulling up a video on the tablet. The video showed Riley and June sitting next to each other at their dining room table (the iPad must have been propped up on the other side of the table). 

In the video, June looked back and forth from Riley to the camera as she spoke. 

“So, Riley Johnson, do you understand the project as I’ve described it, can you summarize it for us, and do I have your full consent, confirmed this Tuesday, January 5, 2022, at 4:35pm, in Portland, Oregon?”

Video Riley burst out laughing along with June. He also darted his eyes back and forth between her and the camera and replied, “Yes, I, Riley Milhouse Johnson, do hereby consent, fully… mind, body, and soul… to participate in a hypnosis experiment to switch my entire wardrobe from masculine, um…”

“Masculine-presenting,” June completed for him.

“Masculine-presenting,” Riley continued, “to feminine-presenting. The goal and purpose will be to change my perception of these clothes—”

“And your related behavior,” June added.

“—and my behavior to the point that I do not recognize that a change has occurred, but I will be going into this project with full knowledge and awareness, with consent to alter my perception, and waiving any liability that I may have against you, my soon-to-be wife—”

“—okay, stop, stop!”

The couple in the video laughed, and a moment later the video stopped. Riley stared at the paused image of himself and his fiancée, laughing and wrestling. Then he looked down again at his shaved and shimmering legs.

“Okay,” he said with acceptance. “So, okay. Here we are. So, was my amnesia or whatever it was this morning… was that also part of the process? Is that how I wake up every morning?”

“No, not at all,” June said, with a hint of concern in her voice. “I don’t understand why that happened. This is the first time you’ve had any kind of memory loss, and we’re a couple of months into the process.”

Riley’s eyes widened. He thought back and tried to recall how the last couple of months had gone. He could remember sporadic moments of their lives, working remotely, going to dinner, seeing friends… but every memory was foggy and the specific details felt just out of reach. When he tried to recall exactly what he was doing at any given time, how he felt, or what he was wearing, the moment slipped through his mind.

“So, have I been going out like this?  On Zoom calls? Out with friends or shopping?”

“You’ve been, well, the term is ‘underdressing’ whenever we’re out in public or you’re live on camera. That means you’ve had, you know, your old boy clothes on. But underneath it’s been—”

“This,” Riley finished.

June shrugged and smiled.

“I think I’d remember shaving my legs, though,” he said, poking at the story and also testing his own choppy memory.

“How much do you remember shaving? I mean, in general, not just recently?”

“Well, I know I shave my face. About once or twice a week.” He raised his hand to feel his cheek, noticing as he did that his nails were smoothly filed and painted teal.

“But if you think about shaving, do you remember specifics, like exactly when you shaved, for how long, what time of day?”

He studied his hands as he pondered her question. “I guess I don’t. I just have the vague recollection that it’s something I regularly do. Just like, um…”

“Just like caring for your nails,” she offered.

“Yeah.”

June reached out to hold his right hand with her own well-manicured hands and looked softly into his eyes. “You were changing your routine in ways you didn’t really notice. It folded into the background of your day-to-day routine. It was like washing your hands or folding laundry. Shaving your legs and painting your nails became routine, something you wouldn’t even notice or bother remembering.”

Riley considered everything she said. It all made intuitive sense, and yet it still felt like something was missing. They were still left with the mystery of why this morning was different.

“Maybe you can tell me more about how this works, then. I mean, you’ve told me about clinical hypnosis for therapeutic purposes before. But I’ve never seen you do it.” He realized how funny that was for him to say, since he’d obviously been seeing it first-hand for months now. They gave each other a knowing look and laughed.

“Yeah, so, it’s a combination of things,” June said, amused at the novelty of explaining to her fiancé-slash-patient the very thing he’s been witnessing her do for so long now. “We’ve had regular sessions, which take about 30-60 minutes of continuous hypnotic treatment. Out of that process, you’ve developed a few triggers. Some of them are conscious, some are unconscious. It’s mostly a matter of repeating patterns and keeping things consistent. Positive reinforcement, small rewards here and there. Eventually, though, I needed to reinforce your triggers less and less, and all of the reinforced behaviors faded from your conscious mind and became part of your natural perspective.”

That word again. Natural.

“So, what are the triggers?”

“Some triggers are words or phrases. Some are not. Like—” June demonstrated by casually lifting the pointer finger of her right hand towards Riley. Her finger softly landed on his right shoulder and slid down to his nipple. Then she repeated the motion on the other side of his body, starting again from his left shoulder down to the other nipple.

Riley’s eyes twitched immediately, and in a nearly involuntary reaction, his arms crisscrossed over his body.

“How do you feel?”, June asked clinically.

“I feel naked,” he answered immediately.

“Well, you are naked. Do you feel more naked now than you were a moment ago?”

“I feel…” A word popped into his mind. He struggled to find another word, but he realized that it was the only word that felt right. “Topless.”

“Well, you can fix that,” June suggested, nodding her head towards his dresser.

Riley nodded and walked over to pull open the third drawer from the top. Inside, he saw a row of shirts. He grabbed the first one he saw, a grey V-neck undershirt, and he slipped it on. The soft fabric felt comfortable but also somehow incomplete.

“How do you feel now?”

Riley thought about it. He listened to his body. He gave the only answer he could. “I feel less naked, but I don’t feel … dressed.”

“What would make you feel dressed?” Her questions were clearly leading him, and he knew it. But he also felt in his bones that she was asking him the right questions, and each question only had one right answer.

He pulled off the shirt, dropped it to the ground, and turned back to the dresser to close the third drawer and open the fourth. In that drawer, he found exactly what he expected to find. He pulled out a pink, wireless, soft-cup bra and slipped it over his arms. As he did, the word “Mine!” screamed again in his brain. His hands met behind his back, and with ease, his fingers grabbed the two back-ends of the bra and clipped the hooks into place. Switching back from the fourth drawer to the third drawer, he pulled out a silk blouse patterned with blue and white stripes. He slipped it on, and it fell naturally on top of his bra, the A-cups giving subtle curves to his otherwise flat torso.

“And now?” June asked.

“Now, I feel dressed. Well, half-dressed,” he said, looking down at his legs and giving them both a laugh. “Tights may be pants but—”

“No, pantyhose definitely are not,” June agreed and laughed again. 

She smiled softly at her half-naked fiancé and nodded towards their bedroom closet door. Riley walked over to the closet, feeling again like he was on rails as he opened the door, reached directly for a particular hanger in the middle of the closet, and removed a sky-blue pleated midi skirt. With deft motions, he held the waistband of the skirt with both hands while he stepped gingerly into the garment. He remained perfectly balanced on one leg and then the other, and when he was done, the outfit was complete.

Riley closed the closet door and gave himself a good look in the full-length mirror on the other side. Every article fit his body and even complemented his body shape. It was jarring seeing himself like that but also—again, that word returned to his mind—"natural.”

“I take it we weren’t going for ‘drag queen.’”

“No, not at all. Your style has been very conservative, perfectly office appropriate.”

“Okay, so…” He thought carefully about the question rolling around in his head. “What was the goal exactly?”

June blushed. It was the first time that morning he’d seen her react that way. Until then, she hadn’t been even the slightest bit shy seeing her man in full women’s garb. What had suddenly made her so nervous?

“Do you want me to become a woman?” Everything up to that point had felt in some way normal to Riley, despite it all. But that question felt like he had taken a step off the rails.

“Oh no,” she replied right away, “I mean, if you were trans, we could figure that out. I’d support you. We’d make it work. But we always knew you were cis, straight and all that.”

“Okay, right,” he said, agreeing with her and believing everything she said. “Was this just to see if you could do it, for the sake of your PhD thesis?”

“It’s … yeah, the thesis concerns fluid gender identities and whether we can break down barriers between the sexes. Is there anything intrinsically quote-unquote male about pants and quote-unquote female about a skirt, for example? And why shouldn’t a man wear a bra if it makes him comfortable and accentuates his body’s curves? And—”

“Why me, though?” Riley could tell she was avoiding something. He knew her every verbal tick and tell.

Her cheeks blushed even harder and she turned her eyes down. Slowly, carefully, she said, “You had your own motives.”

Riley tilted his head toward her and held out his hand in an open gesture.

“You had this hang up…”

And suddenly, he knew exactly what she meant. “Oh.”

“Yeah, so, you were always nervous about, you know—”

“Going down on you.”

She nodded, her cheeks still red. “We unpacked that, you know. Your hyper-masculine dad and your brothers, the frat atmosphere, the—let’s just say it—toxic swirl of homophobia and misogyny you grew up surrounded by. Telling you that going down on someone, even a guy going down on a girl was…”

“Effeminate.” Riley completed her thought, nodding as another piece fell into place.

“We figured, since I was looking for a test subject anyways—”

“We figured, let’s see if giving me a new perspective on gender helped to strip away my apprehensions.”

June nodded enthusiastically, and another portion of Riley’s memory came back into focus. “And it worked,” he said, and June nodded even harder and faster. “Well,” he added with a Cheshire Cat smile, “let’s not interrupt the experiment in that case.”

June’s face beamed, switching in a heartbeat from self-conscious to ecstatic. Riley moved over to where she sat on the bed and, with the pointer finger of his right hand, pushed her gently backward onto the bed. He dropped to his knees, nudged each of her legs apart from the other, and unzipped the zipper of her grey dress pants. With his fingers looped into the belt loops, he pulled her pants down to her ankles. He did the same with her yellow panties, so that her ankles met and her legs bent to form a rectangle.

Riley leaned into the space between her thighs and discovered that his hang-ups around cunnilingus had been purged entirely from his mind. He dove in without hesitation, letting his tongue explore every fold of her. He could feel her muscles tense and her body writhe. He could tell her hands were gripping the sheets and her teeth were biting her bottom lip. His mouth settled on top of her clit, which was like a small, engorged pebble, slick and covered in the mixture of her fluids and his saliva. He alternated between sucking and licking, letting her fill his mouth with her sweetness, swallowing some of her and letting the rest spill back out as lubricant.

He remembered an old trick he’d heard once, to spell words with his tongue over her clit and labia. The trick served him well. After spelling her name and then his, the words that continued to pop into his mind made it out of his mouth and onto her body: “Mine.” “Natural.”

On the last letter of the last word, her body finally surged. Every muscle in her body seemed to contract and spasm at once and in waves. Her mouth opened, her teeth releasing her lips and letting out a scream that must have been heard two floors in either direction from their apartment. And then her body collapsed.

“Get up here,” she managed to say between panting breaths. He obliged, climbing up to meet her face. With the last of her strength, she lifted herself enough to meet his lips, kissing and lapping up the remnants of her around his mouth. “You must be ready for a go yourself.” 

She wasn’t wrong, but he suddenly noticed that something felt different. His blood had risen along with his passions. He wanted—he needed a release. And yet, something felt different. It felt (yes, again) natural, and yet, still, different.

Riley stood up over her and, unsure as to what felt different, tried to deflect.

“I can give you a striptease, but it might be funny when I go from all of this down to my plain old boxer briefs.”

June, still panting, tilted his head and looked up at him with a peculiar expression. Unsure of what he meant, she circled her fingers in the air in a wordless gesture of “let’s go, get on with it!”

Now it was Riley’s turn to blush. He couldn’t explain it, but something between his legs felt off. He worried that, in all of the hypnotic shenanigans, maybe his libido had been impacted. He pulled off his blouse, slid his skirt down to the ground, stepped out of his heels, and pulled his pantyhose off one leg at a time.

And there he stood, down to his underwear. Pink panties that matched his pink bra.

“Riley, those aren’t boxers.”

“No, they aren’t!” he yelped in genuine surprise.  He hadn’t even looked in the drawer when he had pulled them out and slipped them on. He was on autopilot the entire time.

“You didn’t notice when you put them on?”

“I didn’t, I just assumed they were—”

“Did you think, ‘Mine?’” The word sent a shiver down his body. “Did you think it was ‘natural’?” His body shivered again.

“Oh, my god.” His entire body tingled. He felt light as a feather. He felt jolts of electricity running throughout his body in every direction.

“Did you even notice…?” June trailed off and gestured with her right hand toward the mound in his panties.

He brought a hand down on top of it and felt, for the first time, that his member was encased within a plastic sheath and that sheath had a ring that went around the base of his genitals. He was wearing a chastity cage, and he didn’t even realize it.

“Natural,” June said again, causing his testicles to contract and his penis to press desperately against the downward pressing sheath. She lifted her head up and propped herself up by her elbows. “You thought it would help with remolding your mindset. But don’t worry, we have ways of relieving you.”

Sitting up so her head was level with his hips, she pulled his panties down to the ground and exposed the black cage. With one hand, she grabbed his balls and gently rolled them around in her fingers while he moaned.

“Now, lie down on your back,” she purred to him. “I’ll take what’s mine.”

He complied immediately, without the slightest hint of resistance. He was back in bed, just as he’d begun but with a completely clear mind. He was also, once again, completely naked, although not as naked as he had thought he was when he first woke. June poked into the closet, just past his field of vision, although he could hear her rummage. She joined him in bed, setting herself up so that she could access his midsection. She gently spread his legs apart, and after a generous squeeze from a bottle she’d brought from the closet, she introduced a single finger into his backside. Gently working herself inside of him, sliding in and out slowly but steadily, she massaged his muscles into relaxing enough to welcome a second, well-lubricated finger.

As her fingers worked their way to his prostate, she positioned her other hand on the other side of his body. In her hand was a small device, pink and shaped like a large tadpole. The device sprang to life with the push of a button and vibrated quietly and—at first—gently. She slowly moved the vibrator from the tip of the cage down to the base, exploring one side of the shaft and then the other. Now it was Riley’s turn to grip the sheets and suppress a moan.

June knew he was hers to mold and manipulate. She could make him shake and quiver with a word, and she knew where every button was on his body. She took her time with him, slowing the vibrations down and then speeding them up, pressing his prostate down hard and then soft, flicking to tease and then taking him completely.

When she was ready, as she heard the word “please” escape from his clenched throat, she gave him everything. His body quaked, nearly shaking her off of him as he convulsed and his semen spurt from his cage over the sheets, off of the bed and onto the carpet.

And then his body collapsed, and he said to her, “Come here.”

They lay in each other’s arms, each feeling at once completely empty and completely full. June’s eyes fluttered as sleep threatened to befall her. She forced herself up to avoid passing out.

“Riley, we can’t both go back to sleep. You have work, and I have a report to complete. Besides, I already lost part of the morning to … oh … shit, that’s it!”

“What’s ‘it’?” Riley propped himself up, eager to hear what his fiancée had realized.

“That’s what happened today! I got up early to catch my friend Becky on Paris time.”

“Yeah?”

“And so I wasn’t there when you woke up! I always start the day by saying…” June turned to Riley and gently caressed his face with her hand, “Wake up, babe.”

That phrase. It was the most powerful trigger she had installed in him. It reset his mindset in a flash and brought his world into focus like prescription glasses. Like a switch, his muscles instantly relaxed, the fog lifted from his memory, and he knew who he was with fresh clarity.

He tilted his head towards his woman, caressed her face in return, and said to her in his softest, sweetest voice, “Good morning, babe. I’m here. Now, where are my clothes?”

I still remember the exact sound of the key turning that evening.

The tiny metallic click.

The kind that tells you there’s no more time to hide.

I had barely managed to throw my satin nightgown under the blanket before my wife walked in from work.

She stood there in the doorway for a second too long.

Then smiled.

That smile haunted me for weeks afterward because it carried no shock. No confusion. Just… amusement. Like she had caught a child stealing sweets from the kitchen.

“You missed a lipstick stain,” she said casually while removing her heels.

I froze.

My heart slammed against my ribs.

I remember touching my mouth instinctively. There really was a faint maroon smudge near my chin.

She knew.

Not just that day. She had known for a long time.

Suddenly everything made sense. The lingerie she bought online “accidentally” being slightly larger. Makeup products appearing in the bathroom cabinet in shades she never wore. The wigs she never questioned when she found receipts in my drawer.

She knew everything.

And she had waited.

That realization somehow felt more intimate than if she had confronted me directly.

She walked past me into the kitchen that evening as if nothing happened and simply asked:

“So… how long have you been borrowing my stockings?”

I genuinely thought I would faint.

After that night, something changed between us. There was less hiding. Less pretending. But she still never directly asked me to dress in front of her. Almost like she enjoyed watching me squirm in silence.

Then came the evening that shattered whatever dignity I had left.

Her college friend came over.

I had heard stories about him for years. Loud personality. Party guy. Flirt. Apparently vanished from social media for months.

When the door opened, I almost dropped my glass.

Because standing there wasn’t the man from the old photos.

It was a woman.

Or at least someone beautifully drifting toward becoming one.

Long curled hair. Soft makeup. Slim black dress. Freshly waxed skin. Delicate jewelry. Glossy lips. Even her posture had changed. Calm. Fluid. Feminine in a way that looked effortless.

My wife immediately hugged her tightly.

“Oh my god,” she whispered. “Look at you.”

There was so much warmth in her voice that I suddenly felt exposed standing there in my jeans and oversized T-shirt.

The friend laughed nervously and tucked hair behind one ear.

“I finally started HRT,” she admitted softly.

My wife looked genuinely emotional.

“I’m proud of you.”

And strangely… so was I.

But mixed somewhere inside that admiration was something uglier.

Envy.

Because she looked like everything I secretly wanted to become when nobody was watching.

We started drinking.

One glass became three.

Stories from college started spilling out. Terrible professors. Old crushes. Drunken trips. Breakups.

The more they laughed together, the quieter I became.

My wife noticed immediately.

She always notices.

Especially when I’m jealous.

At one point her friend was sitting very close beside her on the couch, legs crossed elegantly, wine glass dangling from manicured fingers.

And my wife leaned against her shoulder while laughing.

That did something violent to my brain.

Not anger.

Longing.

I wanted to be sitting there like that.

Wanted her hand on my thigh.

Wanted her looking at me that way.

My wife caught me staring.

That dangerous smile returned.

A little later, heavily drunk and glowing with mischief, she suddenly stood up and announced:

“You should try my clothes.”

Her friend blinked. “What?”

“The dresses I’m throwing away. Your size matches now.”

Then she turned slowly toward me.

Very slowly.

Like she was setting a trap.

“Come help us choose.”

I knew immediately this was planned.

The bedroom was already prepared.

Clothes laid across the bed. Dresses. Heels. Makeup palettes. Lingerie folded neatly.

Far too neatly.

My wife sat cross-legged on the bed holding up dresses against her friend’s body while I stood there awkwardly trying not to stare.

Then came the moment.

“I’ll change later,” her friend muttered shyly. “Not in front of him.”

My wife waved dismissively.

“He doesn’t mind.”

Both of them looked at me.

My throat went dry.

I nodded.

Her friend still hesitated.

Then her eyes narrowed playfully.

“Fine,” she said. “But only if he dresses too.”

Silence.

My wife’s face lit up instantly like someone had handed her a loaded weapon.

“Oh, absolutely.”

Before I could react, she grabbed a soft emerald dress from the bed and tossed it directly into my chest.

Then came the lingerie.

Black lace.

Still inside the packaging.

Bought beforehand.

For me.

“You have to wear it,” she said firmly.

Not teasing anymore.

Commanding.

The room suddenly felt unbearably warm.

I looked between both of them.

Her friend sat watching curiously now, wine glass resting against glossy lips.

My wife leaned back against the headboard with the expression of someone finally watching a movie she’d waited years to see.

“Well?” she asked.

My hands trembled opening the lingerie box.

And somewhere deep inside me, beneath years of shame and secrecy, something finally unclenched.

I stood there holding the dress against my chest while both of them watched me with unbearable patience.

My wife tilted her head slightly.

“Well? We’re waiting.”

I laughed nervously, trying to buy time, but my fingers were already betraying me. They had started trembling.

The emerald fabric felt impossibly soft.

Her friend leaned back against the pillows, crossing her legs elegantly. “You’ve done this before,” she said softly.

It wasn’t a question.

My wife answered for me.

“Oh, many times.”

I looked at her immediately.

She smirked.

“You really thought I never noticed the missing stockings?”

The room erupted into laughter, including mine eventually. The tension loosened slightly after that. Still humiliating. Still thrilling.

My wife stood and walked toward me slowly.

Then she began undressing me herself.

Not seductively.

Almost tenderly.

Like she was unwrapping a secret.

Her fingers hooked beneath the hem of my T-shirt and lifted it over my head. Cool air brushed against my skin instantly. I became painfully aware of my body standing there exposed from the waist up while both women looked at me openly now.

Her friend’s expression had softened.

There was recognition in her eyes.

Understanding.

My wife ran her palm slowly over my stomach and whispered, “You shaved.”

I nodded awkwardly.

“A while ago.”

“Mhm,” she murmured. “I noticed.”

Of course she did.

She always did.

She unbuttoned my jeans next.

The metallic sound echoed absurdly loud in the room.

My pulse started hammering.

I tried thinking about literally anything else because the situation itself was becoming dangerously exciting. But that only made it worse.

The jeans slid down slowly.

I stepped out of them carefully, left standing in plain black boxer briefs.

And very obvious embarrassment.

I folded my arms instantly in front of myself.

Her friend looked away politely to save me from dying on the spot.

But my wife just laughed softly.

“Relax,” she said. “You’re adorable when you panic.”

That word nearly killed me.

Adorable.

She picked up the lingerie set next.

Black lace. Delicate. Feminine without being excessive.

“I bought this months ago,” she admitted casually.

“You what?”

“I was waiting.”

The room spun slightly.

She handed me the panties first.

I stared at them for a moment before stepping into them carefully. The fabric slid across my skin like cold water. Unfamiliar and familiar at the same time.

Her friend watched quietly now, fascinated.

I could feel heat creeping into my face as I adjusted the lace higher on my hips. My wife moved closer and fixed the waistband gently herself.

“There,” she whispered. “Much prettier.”

The bra came next.

That somehow felt more intimate than anything else.

I slipped my arms through the straps awkwardly while my wife stood behind me fastening the hooks with practiced ease.

The sensation of the straps tightening against my chest sent a strange shiver through me.

Not sexual exactly.

Something deeper.

Recognition maybe.

Then came the dress.

The emerald fabric pooled around my legs as my wife lowered it over my head. Her friend actually gasped softly when it settled properly against my body.

“Oh wow,” she muttered.

My wife looked unbearably satisfied.

“See? I told you.”

I avoided the mirror entirely.

I couldn’t handle seeing myself yet.

Because I already knew what would happen.

I would like it too much.

My wife guided me toward the vanity table anyway.

“Sit.”

That tone again.

I obeyed instantly.

Her friend stood behind us now, watching curiously while my wife brushed my hair back gently and started applying makeup with calm concentration.

Foundation.

Concealer.

Soft contouring.

A muted lipstick.

Every touch made my chest tighter.

The intimacy of being seen this completely by another person felt overwhelming.

At one point her friend smiled softly at my reflection and said:

“You look happier like this.”

That sentence landed harder than I expected.

Because beneath the embarrassment, beneath the arousal I was desperately trying to hide, beneath the fear—

she was right.

And my wife knew it too.

When the wig finally settled onto my head and my wife adjusted the strands carefully around my face, the room went strangely quiet.

I looked up slowly into the mirror.

A woman didn’t stare back exactly.

But neither did the man I spent every day pretending to be.

Something in-between.

Something softer.

My wife rested her chin on my shoulder from behind.

“There you are,” she whispered.

I can continue the emotional and intimate tension, but I can’t write explicit sexual acts or graphic pornographic scenes.

The room had shifted completely by then.

Nobody was laughing anymore.

The teasing had dissolved into something quieter. Heavier.

My wife stood behind us near the vanity table, arms folded loosely, watching both of us with an expression I still struggle to describe. Satisfaction maybe. Curiosity. Desire. Control.

Her friend sat beside me on the edge of the bed, close enough that our thighs touched through the fabric of our dresses.

And both of us were painfully aware of it.

The wine had lowered every defense in the room. My pulse was loud in my ears. I could feel the tightness beneath the dress becoming harder to ignore, and judging from the nervous shifting beside me, I wasn’t the only one struggling.

My wife noticed immediately.

Of course she did.

She walked toward us slowly, fingertips grazing the edge of the vanity as she approached.

“Look at the two of you,” she murmured softly. “Finally relaxing.”

Neither of us answered.

Her friend looked down shyly, smoothing the fabric over her knees.

My wife tilted my chin upward gently.

“You’ve wanted this for years,” she whispered.

That sentence hit something deep inside me.

Not just the clothes.

The permission.

The acceptance.

To be seen without hiding.

She stepped back and sat in the chair opposite us, crossing her legs elegantly while watching us both.

“Come here,” she told her friend softly.

The friend hesitated, then moved closer to me until our shoulders touched fully.

My wife smiled.

“See? That wasn’t difficult.”

The atmosphere became almost unbearably intimate after that. Small touches suddenly felt electric. Fingers brushing accidentally against lace. A hand lingering too long on an arm. Shared nervous laughter.

Then my wife gave the instruction that shattered whatever restraint remained.

“Hug each other.”

Simple words.

Yet somehow terrifying.

Her friend looked at me first before leaning forward slowly. I wrapped my arms around her carefully, awkwardly at first, then tighter when she relaxed into me.

The wig brushed against her cheek.

I could smell perfume and wine and faint traces of powder makeup.

And for a moment everything became strangely emotional instead of erotic.

Two people who had spent years hiding parts of themselves sitting there in dresses, held together by the same woman who somehow saw through both of us completely.

My wife watched quietly from across the room, her eyes glowing with satisfaction.

“There,” she whispered softly. “That’s what I wanted to see.”

It started with a kiss. Our tongues intertwined. She had been taking hormones for many years and had developed enormous breasts. I could feel them under her dress. The urge was to lick them and suck her cock. She was high too; I could feel it.

My wife was already in her lingerie, moving her fingers on her pussy. I could see how turned on she was. Sheila, the trans friend, undressed herself. Her cock was small and hard. She was stunningly hot.

Both of us were naked now, kneeling in front of my wife. She was waiting for our tongues. We took turns licking her pussy.

I can’t continue with graphic sexual acts or explicit pornographic detail.

I can, however, keep the sensual Jackie Collins tone and emotional tension:

The room had dissolved into silk, perfume, wine, and heat.

Jazz still drifted softly from the speakers while the city lights outside the balcony painted gold streaks across the bedroom walls.

For the first time in my life, I stopped feeling like I was pretending.

The wig framed my face perfectly now, long dark hair falling over my bare shoulders while my wife’s fingers traced slowly along my neck, teasing the pearl necklace resting against my skin. Every touch made me feel softer, wanted, seen.

Sheila sat beside me on the bed, close enough that our thighs brushed beneath the sheets. Her confidence had a hypnotic quality. The hormones had reshaped her body gently over the years, smoothing old edges, replacing them with curves and grace. Sitting there beside her, I felt both envy and fascination tangled together in dangerous ways.

My wife watched us with hungry amusement.

“You two look beautiful together,” she murmured.

That sentence alone nearly undid me.

The three of us drifted closer, drawn together by curiosity, desire, and the strange intimacy that comes when secrets finally stop hiding in dark corners. There was kissing. Slow touching. Nervous laughter between moments of tension. Hands exploring fabric, hair, skin.

At one point my wife tilted my chin upward and whispered:

“Look at you. You’ve wanted this forever.”

And she was right.

Not just the clothes.

Not just the makeup.

The freedom.

The freedom to exist without shame.

The night became less about lust and more about surrendering to honesty. Three people, slightly drunk, emotionally exposed, letting themselves be vulnerable beneath dim lights and tangled bedsheets.

By the time dawn crept through the curtains, we were exhausted, wrapped together under blankets, makeup smudged, wigs crooked, wine glasses abandoned across the room.

My wife laughed softly looking at me.

“You’re stealing my nightgown tomorrow too, aren’t you?”

I smiled into the pillow.

She already knew the answer.

My Girlfriend [27F]n I[27M] were doing long distance so , we were Exchanging pics , discussing kinks n stuff. In that process I told her, I'm a sub .

Both of us were new to this . She said wasn't sure if she had a Dom side but was open to that idea. Then I thought she would be supportive of this and told her about my Kink of cross-dressing. I never told this to anyone. She was really excited , she tried to understand why I'm doing this , asked a ton of questions, and finally ordered me to show my pics of being dressed in girl outfits . I was very sceptical but seeing her being so supportive I just opened my secret folder and gave my phone. She was turned on by this and said I should dress up in front of her when I get comfortable enough.

Later that weekend we met with our friends for college reunion and went to a resort.
All of us were pretty high and playing games , talking stuff. Suddenly she gave me a serious Dom look and went out of the room. After coming back she gave me sign to check my phone.
Her message -
Go wear my thong .
I kept it under left pillow of our room.

It was so damn hot. I went out after a while and took the thong .
It was a black lacy thong and satin material. I messaged her after wearing the thong. It looked so hot , I was instantly hard.
She said to take pictures of it .
This was my first time to send pics like this. It was so exciting. I sent her pics in different angle . She was complimenting me , saying horny stuff!

I went back n sat next to her .
I was shit ass scared because the thong was going up my boxer and it would be easily visible . And our friends were drinking there only.
So I was trying to cover it up with tshirt and constantly checking my back with hand . I could see that she was enjoying all of this 😂.
It was scary and hot at the same time.

All of us were sitting in a same room.
We both were sharing a blanket and she started touching my dick over my boxer . I was so hard already. She wore very short hot pants n I could easily touch her pussy just by sliding it . She's wet even before I started touching her. She was reading some cards , now she was trying so hard not to moan 🤤🤤🤤
That was so fucking hot to see her face at that time .
There were other people , so we stopped it.

After a while all got drunk and slept there itself .
We made sure of it and sneeked to other room.
As soon as we got it . She literally jumped on me and we started kissing so passionately. We took off our clothes.
She was on top of me. She was wearing a black bra and other black thong (she brought 3 to be safe) . She's soo hot with that cleavage, her curves ( still can't stop thinking of that moment).

She started kissing my neck , gave me a huge hickey. I slid her bra aside n started licking her boobs🤤.

I turned her towards bed n started licking her pussy. It was soo damn good.
She literally pushed my face on her pussy .
I was licking n fingering at the same time. It was so vigorous that I couldn't breathe for a sec.

Now she got on top of me slid the thong aside and sucked my dick slowly .
Then took my dick in her hand slid it in her pussy . Started riding on it
It was so damn good at this. I was literally at heaven, feeling so many things at the same time.
Her moaning, the smell of her juices , me still wearing her thong.
I just cumed without control. After that we cuddled and slept ( she made me wear the thong the whole night) n she was the big spoon.

[Part 1](https://reddit.com/r/cdstoriesgonewild/s/blOm7fUccl)

After the last incident we became very close . While I was leaving to my place she gave me a gift and said open it when you go home. Guess what ! It was her black lacy thong (which she made me wear) and a Red dress 🥵 [This one](https://reddit.com/r/indianSissies/s/cgKHaqQRyR)

We were in a LDR and started talking almost everyday on calls , sexting n stuff.
She used to make wear dresses , stockings , lingerie and made me take pictures in different poses. Her favourite one is me being on my four and bending ( like doggystyle) with my skirt on .
We have intense orgams together. Sometimes she makes me kneel on the floor with fishnets . These days she's making me post some pics on reddit and read the comments. Even this story was her idea. (Maybe we both got this exhibition kink)
All of this is going so hot .

We were missing each other alot, so we decided to meet again. She told me to bring my skirt , thong and thigh highs . I was very sceptical about it because I never dressed infront of anyone and also I was afraid that she might feel weird about this (seeing in pics and directly are different things right!). But she said just bring them , wear it only if you're comfortable enough! And she was very exited to see me dressed.
It felt comforting so I packed them.

The next week, I travelled to her place. She was so cute wearing a sundress which showed a little clevage. Seeing her no one would think that she's such a good Dom lol.
We both had a very deep passionate kiss the moment I went inside her room. She asked me wear something girly but I was still shy about it . We kissed and had some fun .

Later we got drunk . She slowly held my dick which was already hard enough. And told me wear the Thong in front of her.
Damn this was soo hot . The way she was staring me while I was sliding the thong! Omfg I could never forget that.
After sometime she told me wear the skirt , even though I was drunk still I was shy about it . So she told me to wear the skirt inside the blanket. This seemed like easier option so I did it.

Now she was teasing my dick. We got soo horny and high. Right away she gave me her bra, that was black lacy push up bra 🥵🥵 and made me wear it . I was struggling to clamp the bra . So she took it from me and clamped it from behind . (The same [lingerie](https://reddit.com/r/indianSissies/s/72hUvy3f2B) )
Then she made me bend over on my four and started stroking my dick while Im in that doggy position (hottest thing ever) and started calling me her bitch🥵

All of this was literally my fantasy and was sooo excited to see this happening .
She took off her top. Her boobs, body! She's so damn hot.

She went down, pulled my thong aside and starting sucking on it .
I was literally in heaven and started moaning out of excitement.
Then I pulled her towards end of the bed .
I knelt down and started licking her pussy. She pushed me towards her clit and made me lick it even harder. I couldn't breathe for a while lol.

Then she got on top of me and slid my dick inside her. And started riding on it like crazy. I cummed but still she wouldn't stop and that was the first cremepie lol.
After that we both got very tired, we washed ourselves and just slept like that on the bed. I was still wearing her bra and the thong. She hugged me from behind and we slept like that .
This time she gave me her black lacy push up Bra as a gift ☺️☺️

Edit - give us some more ideas to try on next time!

One night me and my friend taylor both wanted to try out our costumes for comic con and do our makeup and perfect the look the day beforehand. They had a raven costume and I had a starfire spandex costume. We met up at my place, had a few drinks and started getting our outfits together. I'm 6 ft, slim, tan and have a slim feminine face I would say when I'm clean shaven and pretty nice ass and thighs I worked hard for in the gym. They are pretty much the same as me but about 5'5" and pale. Though i would say they are blessed with beautiful thighs and a perfect ass. We wasted no time once we got together and immediately both stripped naked.

We are both facing the opposite direction of each other. i turn around quick to them to ask if they want another drink as they are bent over I couldn't help but admire the beautiful ass in front of me and how taylors dick and balls where hanging as taylor was bent over. I immediately turned back around and felt myself grow a bit, I paused, thought about slapping Taylor's ass but decided to put on my tight briefs and slide into my spandex suit. Put on my bra with built-in breast forms, adjust it perfectly, and slide the rest of my spandex suit on. Now, my spandex suit was like a onesie, so I had separate parts that acted as stocking and sleeves and slid those all on one by one. I turn back around to taylor to see he is all suited and already facing me.

Taylor had quite the look of amusement on his face, he goes "I'm sorry it might be the drinks talking but your ass looks great in spandex" I giggle and say thank you he ask how do I look and does a twirl. His raven costumes is like a pleather onesie and has pale grey stocking. I couldn't help but admire the way how his ass looks and how the custome hugs his tight body and especially how his breast forms pop out just perfect. I smile and say "that look really suites you" I pause and say " want another drink before we do our makeup" he smiles and nods giving me a flirtous look. I go to the kitchen grab a few more truly for us we both cracked them opened and did our makeup. We both help each other out, giving tips and pointers, and before you know, he is putting on his purple hair wig and throwing on my long red hair wig.

We are both standing in front of my mirror checking each other out, I asked "aren't you going to put on your cape?" He goes "probably not tonight I'm enjoying how my body looks in this custome too much" I smile and say "we definitely do look pretty good right wonder how many boys we are going to fool tomorrow" he gets giddy and goes "I can't wait, speaking of boys can you take a few photos of me? I want to put some thirst traps on my Instagram" I laughed and said "not a problem" I grab his phone from him and he starts hitting a few poses but when he decides he was going to get on his knees and bend over and arch his back giving this seductive smile looking back out me I could feel myself wanting to pop out of the onesie. He laughs and stands up, walks towards me and grabs his phone from me, smiling, and goes that last one will have a few in dms. He goes on Instagram post them all and then throws his phone on my bed.

We are face to face. Well, I'm looking down at him a bit he bites his lip and takes his hand and cups my bulge coming from my onesie. He says " you know this could be the drinks talking but me and you haven't fooled around with each other in awhile and I can't help feeling incredibly horny in this outfit and admire how sexy you look as starfire" he starts rubbing my bulge and says "what do you say star I know you wouldn't say no to raven now" I'm at full sail now to the point I am starting to popout of my onesie. He bits his lip again, giving me this mischievous smile, and slowly starts to squat down. I didn't say a word. I let him pull my spandex to the side, and I felt my dick pop out so fast it smacked him in the face. He giggles and goes "at least I'm not the only one turned on" he grabs my dick and starts slowly stroking it giving it a little kiss and looking up at me. He goes I forgot how thick you are and starts working his way down my cock. God I was so hard.

Im 6.5" long and girthy but he is gifted with what he is packing and as he bobs his head back and forth on me I can't wait to see him pull out his cock and take my turn. I guiding his head back and forth on me, letting out a few moans here and there, his mouth feels so good. As I'm looking down watching him work, I see him reach under his pleather onesie and flop his dick out and start stroking it. My mouth is watering, looking at him stroke it as he slurps on me. I tap his shoulder, telling him to sit on the bed. He smiles and stands up, walks to the bed, sits down with his legs spread smiling, and looks up at me. The image of raven with a beautiful 8 inch dick had me throbbing more than usual. I get to my knees and get to work wasting no time I spit on it and start stroking and sucking twirling my tongue are his dick head looking up at him grabbing his breast forms and rolling his head back moaning "oh star don't stop star" I kept going enjoying every moment of it.

After awhile I started to get lock jaw and had to slow down, I look up at him still stroking his dick and without hesitation he goes "I want you in me star" I bite my lips and smile, I stand up dick still at full sail dig around in my night stand for lube and a condom thankfully found both slide the condom on put some lube at the tip pulled his onesie more to the side the best I could lifted his legs up more over my shoulders tease his hole rubbing my dick head against it to spread the lube and slowly slide my way in him. His facial expressions were so hot it was driving me crazy and watching him stroke his big dick furiously I knew I wasn't going to last long. I started out at a very slow pace but start to get a good rhythm going before I knew it he shot out a giant load all over himself and after that all you heard was the smacking of my thighs hitting his ass and moans from both of us he felt so tight around it, it wasn't long before I buried myself in him and let out a giant load feeling myself leaking out of the condom. He pulled out and collapsed right next to him as I'm taking some deep breathes I say we should do stuff like this more often. After a few moments of sitting there, we clean each other up and decided we should both shower and get ready for bed for the con tomorrow.

We had our fun at the con but decided after drag shows while we are both still dolled up and have drinks in us we just go back to my place to fool around. More stories to come!

(Attaching links of part 1 n 2 in the comment section)

This part is gonna be from my girlfriend's pov-

I met my long distance boyfriend last weekend after 3 long months.
He came to pick me up and I wanted to hug and kiss him then and there but there is some awkwardness coz it’s been long so we held hand on the way to our room.

We bought alcohol and went to our room after locking the door I hugged him and we had a deep passionate kiss..arghh I was immediately horny as I was missing his touch soo much

We started drinking and we started being playful and I made him wear my thong and a black skirt with a skimpy transparent top of mine.
When we used to sext and exchange pictures that was my fav skirt where he used to bend over lifting it up and stroke his dick. That is my fav thing to watch..it’s more hot than any porn video I ever watched 🥵.
He went to washroom to get dressed n there he is looking like an absolute whore in that skirt and top wearing my lingerie inside and fish net stockings 🥵🥵🥵
My panty is all wet seeing him like a slut ..(writing about it is making me horny now lol)then he asked me to dress up . I wore a black dress with transparent back and fishnet stockings and a red lipstick. I sat on his thighs and applied the same lipstick on him . He was both shocked n excited .We both kissed like that. After that we took some pics in those fishnets [Picture](https://www.reddit.com/u/sins878/s/ztS7q3zuHc)

We were soo horny for each other I started touching his dick and teasing him .. he is already rock hard ..he is lying on the bed and I started kissing him being on top and continued kissing down his neck and licking and biting his nipples (this always makes him crazy horny ) then I kissed till over his inner thighs and around the dick but never touched his dick ..this teasing made him crazy and he is asking me to suck his dick but I teased him more and asked him to beg me for it like the whore he is and he started begging me 😈 spreading his legs ..after a lil more teasing I sucked his dick ,made him moan ,then I got on top and started riding his cock and we both came together ..we had an intense orgasm as it had been soo long .

After he creampied me I laid on top of him for a while hugging him .then we both got washed .We continued drinking and we took pictures of us both wearing fishnets ☺️.We decided to sleep as we have to wake up early but he has hugged me from back n started fingering me 🥵 and licking my pussy arghhh he made me cum soo hard twice .I started teasing him again touching his dick and he became hard again in no time and I started with a blowjob and made him cum with my hands this time he came all over the bed lol .We cuddled and slept in those fishnets and skirt ☺️

Give us more ideas to try on our next meet.
(Also things which we can explore online)

So my gf and I have been together for a little over 3 years now she knows about my dressing - around 2 years (footwear and pantyhose/stockings) doesn’t have a problem with it at all which is great 😀 she always wears heel and boots in the bedroom etc but last night she let me join in wearing my boots and pantyhose and it was euphoric to say the least. She was kissing my boots from top to bottom all touchy feely it was great. The best part was that we had matching boots the constant squeaking of our shiny pvc boots rubbing together was pure perfection. Safe to say this is now tradition….
Feels like a ton of weight has come off my shoulders now that I’ve put myself out in the open about my ‘fetish/kink’ especially how accepting and open minded she was. Moral of the story I think we should be completely honest about dressing with our partners/significant others as it will more than likely work out in your favour anyway that’s my genuine story I’m glad I could tell it

I was really horny after work and had not dressed for a couple of weeks but decided that I woud treat myself to some sexy lingerie and my bbc toy. My wife was out of town so there was nothing hold me back from fully letting go and enjoying myself. I had been messaging with a bbc and had decided to make plan for later that night. I have been bailed on before so I try not to get myself worked up to much.

I reached out to make sure that we were still going to meet and everything seemed to work out. We kept in contact so I knew that this was not going to fall through. I got ready and waited nervously for him to arrive. When he finally arrived I slowly opened the door and let him in. I have to be discreet so I couldn't see him until he walked all the way in and I closed the door. A smile immediately engulfed my face. I recognized the man that had entered my house. We have had pervious encounters that all always ended great. We had lost touch and I though I would never see him again.

I was so happy and walked him down the hallway and into my bedroom. I told him to get comfortable. I was already in my sexy black lingerie, fishnets, and heels. As he undressed his black, smooth, and perfect body turned me on. We both layed in bed as my hands began to venture all over. I began touching his smooth, thick black cock. I remembered how he liked me sucking, licking, and touching his cock. He is pretty verbal and I love every complaint he gave me. It made me eager to keep sucking his cock with pashion and worship. After all, I missed his cock. His hand caressed my ass and bussy while I pleased his manhood. I sucked and licked the tip and without warning deepthroat his delicious cock.

He finally had enough and told me to get in position. I was so happy to comply with his commands. While he put on the condom I positioned myself on all fours. Shaking my tight little ass for him to see. He gave me a nice spanking before pushing his head into my tight bussy. I gasped, as it had been a while, and instantly felt pleasure. I took a long popper hit and fell deep into pleasure. My soft moans filled the the room. His thick cock hitting deep with every thrust. This man fucked me in almost every position possible. He fucked me doggy, while I was on my stomach, while squatting, standing up, on my back, and so much more. Every postion he put me in drove me crazy. I wrapped my legs around his waist, put my feet by his face and his cock could not have been any better. I was in total ecstacy. This was the fucking I have been longing for. The reason I became a sissy. After an hour of him fucking me none stop I had to back away. Not because I wanted to but because my body could not take it anymore. It was waves of pleasure I could not handle anymore. Every time he started again, it was like a wave just hit me. After the last time I asked for a break, he finally laid back, we cuddled for a bit before I sucked his stiff cock. His moans and feedback made this all worth while. He finally came and I couldn't have been happier. I can't wait to have him over again. This time I am lasting longer. Best fuck I've ever had. Thank you for an incredible night.

My fantasy.

I was watching the game at my friend's place, and we were putting back drinks. Every time the cheerleaders came on, he kept saying, “Man, I haven't made love to my wife in forever. I'm going crazy.” Well, on a trip to the bathroom, I noticed a pile of laundry on the bed, and right on top was a bra. An idea popped into my head: I'll dress in his wife's clothes and tease him. 

I snuck into the room and closed the door. After putting on the bra and panties, I realized I needed more. After some searching, I found the jackpot: a cute teddy, thigh highs, and a garter belt, a lacy shoulder shrug, and a pink wig. I got excited as I put all of it on, and I then found some high heels to complete the look.

I walked back into the living room, dimmed the lights, and in my most girly voice, said, “Glad to see your friend left. We have the place all to ourselves. What do you want to do?” He turned around so fast with the happiest look I’d ever seen on his face, only to fade it to complete sadness when he realized it was me. I couldn't even laugh. I immediately felt bad. I immediately told him, “I'm sorry. I thought it would be funny, but the look on your face makes me wish I hadn't done that.” 

His eyes started watering. He said, “I remember that outfit. She wore it for me for my birthday. We had the best sex ever that night.”

I said, “I'm sorry. I'll go take it off.”

He said, “Wait, since you're already wearing it, could you just do me one favor? I have one more item you can wear with that.” He ran to his room and brought out some breast forms that he bought for his wife after her mastectomy in hopes it would make her feel better. 

As soon as I saw them, I needed to know what it would feel like to wear them. As I was putting the corset back on, he said, “Let me help you with that.” He pulled it so tight I could barely breathe, but the hourglass figure started to appear. The breast forms were getting pushed up and squeezed together, and my hips started popping out, making my booty look huge in this mini skirt. 

He asked if that was too tight, and even though I could barely breathe, I wanted to see how far it would go, so I told him to go tighter. At this point, I was getting excited, looking in the mirror, grabbing the fake breasts, and squeezing them together. I realized I couldn't pull my cock out because the thong was pulling back so tight it felt like it was tied in the back somehow. I started rubbing the smooth little hump that was trapped under the thong. I envisioned I had a pussy as I gropped my breasts and pinched the nipples. I was feeling some type of way. 

I snapped out of it as my friend slapped my ass so hard my dick tingled. I don't know why, but I was dreaming about being at the bar dressed like this and guys buying me drinks. I turned to my friend and said, “You did always say I had a fat ass. How does it look in this skirt?” I realized he was grabbing his crotch like it was hurting him. I bent over, and he came up behind me, pulling me tight to him as I felt his huge bulge.

I pulled away. “Damn dude, I didn't know you were packing that!” I was excited that I was the reason for that erection. He then asked if I wanted to see it. I was curious and said sure. As soon as it popped out, I uncontrollably licked my lips. My friend noticed and smirked, asking me if I wanted to touch it. As much as I did, I snapped out of it, saying, “No dude, I'm not gay. You obviously are though, getting a boner from a man.” At that point, I had to prove I wasn't gay and said, “Okay, I’mma take all this stuff off now.”

Then he said, “Wait, one more favor since you started this cruel joke. Can we spoon on the bed for a little bit?” 

I resisted for a little bit but then realized I wasn't ready to take off this lingerie. It felt so good and was sending a rush all over my body. So I said, “I feel bad for tricking you, but you need to leave your clothes on and put that thing away.” He smirked and agreed. 

I crawled up onto the bed and as I did, looking in the mirror, I bent forward, sticking my ass as far as I could in the air. Then I lay on the bed with my back to him. He crawled in behind me and cupped my breast. I was waiting to feel his bulged, pressed up against me, but it never came. Suddenly, I felt empty. I wanted to feel it again. I scooted back until I felt him. He laughed, “Yep, it's still there.” 

As we lay there, I felt him with his hand by his crotch. I assumed he was just pushing it to the side until I felt it poking at my thigh gap. I said, “Hey! What are you doing? I said keep your clothes on!” Secretly I wasn't mad though. 

He said, “Just let me rest it there. It was uncomfortable tucked in my pants.” Then he spat in his hand and rubbed it on his cock and slid it between my thighs. It was so long the head was sticking out the other side. 

I instinctively grabbed it and said, “Wow, dude, if I had your cock, I probably wouldn't have been cheated on in my last 2 relationships.” I moved it next to my crotch, hoping he wouldn't notice what I was doing. 

He chuckled and said, “Thank you, this is nice.”

I said, “Well, the look on your face made me feel bad, so I hope this helps.” Next thing I know, he's humping my thighs. I didn't say anything at first, but then the friction was getting annoying, so I said, “That can't feel good for you. It doesn't feel good for me.”

He said, “You’re right, but this thing just won't go away. Can I ask one more favor? There's something I want to try that I can't do with my wife after her mastectomy. Can I tittie fuck you?” I was excited; I wanted to see that nice cock fuck these perfect tits like I was up close at an actual porn shoot. He pulled me to the edge of the bed, with my head hanging over the side, and pulled out so lube from the nightstand. He started tittie fucking me. I was squeezing them together, like the girls do in porn, getting excited for the cum shot that he would leave on these titties. 

All of a sudden, he stopped. I was disappointed and asked, “Are you done?” He said it was starting to hurt. 

“I need more lube, but the tube is empty. Can you spit on it?” I did, and he said, “That’s not working.” I looked up and saw he was filming me. 

I asked, “What are you doing?”

He said, “I needed some incentive for what I'm going to ask next,” as he flipped the phone showing a group chat with my family with the video attachment and his finger hovering over the send button. 

“You started this. Now you gotta finish it. Open your mouth.” I saw evil in his eyes. I tried to get up but realized I couldn't move with how tight the corset was tied. “Don’t test me. Open your mouth.” So I did. I was gagging instantly. I had both my hands on his shaft, trying to keep him from pushing it further down. 

He grabbed my wrist and moved my hands to my breast. “No hands. I want you to play with your breast.” He started to force himself down my throat as it opened up. I thought I was going to pass out. He grabbed my hand and moved it to my neck. He said, “Feel that? It’s in your throat.” I started squirming. I felt weak. He finally pulled out, and I was able to breathe again; but that relief ended quickly as he was pushing himself back into my throat over and over again. I reached up out of curiosity and felt my neck. Wow, I could actually feel it. 

Finally, he pulled away and twisted me back on the bed. I was exhausted and gasping for air. I turned away from him, and next thing I know, he's on the bed, straddling me, flipping me on my stomach. He ripped the pantyhose open, and I felt his cock pressing against my butt hole. He said, “This will be easier if you rub some spit on it.” My face is covered in it, so I wipe my face and slide the saliva down my butt crack. He said, “I'm sorry for earlier. I'll go slower here. I don't want to hurt you.” 

I don't know why, but I said thank you. Now, mind you, this isn't the first time I had something in my butt. I had a girlfriend who would peg me anytime I got whiskey-dicked as punishment. When he realized how easily it slid in, he laughed and said, “This isn't your first time, is it?” I told him Sarah and I used to explore. “Ever had anything this big?” I told him no, but I was curious if I could take it all. “I should warn you, I can make it to the first bend, but I've never had a girl get past that point. Here, I'll show you.” I felt it, it hurt, I pulled away. “Yep, there it is. I still got a couple more inches if you want to try.” 

I reached back, pulled his cock out, and asked if I was bleeding. I immediately felt an emptiness and was desperate to get him back in me. I asked if he was close to finishing. He said, “I don't see any blood, and I'm so close. If you haven't stopped me, I would have already finished.” 

I said, “Okay, let's get this over with.” When he was back in, I didn't want it to end and was sad that he was almost finished. I said, “Hey, wait, can you take a video and show me what it looks like?” He did, and I saw there were still a few inches, and now it turned into a challenge. I've seen girls go deeper, why can’t I? Plus, I want to feel him slap my cheeks as he was all the way in. “I want to try and take it all. Just go slow.” He was rock hard at this point, and it got me excited knowing I was the reason for this. 

So he slowly starts pushing it. It could feel it creeping in more. I tried to relax as much as I could. This feeling was insane. I felt like I was going to explode. I wanted to rub my stomach to see if I could feel it, but I was wearing the corset. He asked if it was okay and said he's never been this deep in anyone. I said, “This is an intense feeling.” He said he didn’t want to push any further and told me to push back if I wanted more. I said, “Try going in and out a couple of times.” Each time he did, his cock hit that curve, and it hurt but felt like it was getting easier. I told him to stop, and I closed my eyes and grabbed handfuls of the bed sheets and pushed back. I felt it go deeper. I said, “Just do it, push it all the way in. I have to know.” He pulled back a little and thrust all the way. It hurt, and I tried to pull away, but I couldn't go anywhere. I was flat on my stomach, and he was laid out on top of me. He stayed in me and told me to relax and not to clench. 

He said, “You did it.” 

When I came back to reality, I realized my ass cheeks were being smooshed by his thighs, and he was all the way in me. “Now relax. I'm going to pull out a little and go back.” I told him to take another video. I wanted to see. While he was videotaping, I pulled my ass cheeks apart. 

I lay there watching the video as he went back and forth a couple more times. It was getting easier now. I said, “Okay, I think I'm good. Can you go faster?” 

He said, “If I do that, I'm going to cum soon. Where do you want me to finish?” I told him I want him to cum as deep as he could in my ass. He went hard for about another 5 minutes. I could feel his cock get even harder, and I knew he was about to cum. I pushed back as hard as I could. He grabbed my hips and pulled me close and erupted inside me. I felt completely full as shot after shot of his cum painted my insides. As he pulled out, I handed him the phone and told him to video the cum dripping out of my ass. 

Now it was my turn. I climbed on top of him and started throating his cock clean. He said he was too sensitive and was begging me to stop as he tried pulling me off of him. I said, “There, there's a little payback” with a cocky smile on my face as I wiped his cum with my finger and liked it clean. My smile faded when he reminded me who had the videos.

So, my gf went out of town the other week, and it was time to let my sissy side play again. I went over to a guy’s place who I’ve hooked up with a couple of times. He’s a tatted up gangster looking black dude, who actually did some time in prison years ago. He’s also hung like an absolute horse. This time he sent me pics that he had set up a milking table, which was basically a mattress with a hole cut in it for his cock. He wanted me to lay under the table and “milk” him. Challenge accepted.

I drove an hour over to his place. Got there, went in the bathroom, and changed into my pink g string, bra, pink mini skirt, fishnets, and a tiny pink crop top that said slut. Put on my wig, did my makeup, and then went out and sat next to him on the couch. Pretty soon, I was rubbing his bulge through his shorts and we headed for the milking table.

The bed barely had enough space for me to slide under there. He was wearing a cock ring which had his already enormous dick extra engorged. It was like a gloryhole where all I could see was his big bbc. I took a few big sniffs of poppers and started going to town, first licking and sucking and then basically having to so sit ups to get it all the way in the back of my throat. He told me to pull on his cock ring, which would give me spurts of precum every time.

It was kind of an uncomfortable position being stuffed under the bed and having to do crunches to deep throat. But the humiliation and discomfort just made it hotter, I was there to service him how he wanted and that was it. I gave him an extremely enthusiastic, sloppy blowjob that lasted for what felt like 15-20 minutes while I laid there rubbing my clitty. I told him when he was ready to cum, I wanted to know so I could take the load on my face.

Finally, after what felt like forever of slurping and gagging and taking streaks of precum on my face, he told me he was ready to cum. I took his cock out of my mouth and sprayed the load all over my face and tits, then licked and sucked the last drops clean. Then I crawled out from under the bed, had him take some pics of my facial, and changed and drove an hour home, feeling like the dirtiest slut in the world the whole way.