u/cdresser70

So most of my stories are about me as a crossdresser but I have also met many sexy TS women while in guy mode. This is one of those stories. I was on a work trip but couldn't bring anything to dress up in. I was online looking to see if I could find a CD or TS to join me in my hotel room for some fun.

I got a message from a beautiful blonde TS, she said she'd love to come over and give me a massage and top me if I was into that! I said absolutely and we set up a time to meet in a few hours after she got off work.

When she arrived at the room, I let her in and she gave me a hug, her fake tits felt amazing pressing against me. I could tell they were cheaper ones because of how firm they were but I actually like those.

She told me to strip down to my underwear and lay down on the bed. Once I did, she did the same in front of me, taking her bra off but leaving her panties on. She told me to flip over so she could rub my back, then got on top of me and started giving me an oil massage.

I kept on trying to grind my ass upwards when I would feel her bulge between my cheeks. She pushed me down and said I'd be getting that eventually.

Once she was done, she told me to flip back over, where she straddled my face and pulled her thick cock out of her panties and starting rubbing it on my face. She teased me a little as I tried to get it in my mouth but she soon let me start sucking her. As I sucked her she rubbed my cock over my underwear but didn't start stroking it right away.

It didn't take much of me sucking her before she pulled her cock away and said omg I need to fuck that ass. She got off of me so I could take my underwear off and get on all fours as she got some lube from her bag. Then I felt her pressing the head of her cock into my ass. I thought I was pretty experienced at getting fucked but her thick cock took some time stretching me out.

After a short time and more lube she was all the way in me and started pounding away. She said wow I can tell you love getting fucked, don't you? All I could respond in between my gasps was how good her hard cock felt in me. Then she pushed me so I was laying completely flat on the bed, she wrapped her legs around mine, I could tell she was getting ready to cum. Sure enough, she tensed up and thrust into me as hard and deep a she could, letting out a long moan. She laid on top of me for a moment, and turned my head towards her to kiss her.

She pulled out and said it was my turn to cum. She laid on the bed and told me to stand next to her. She leaned over and started sucking my cock, pausing only to tell me to let her know when I was going to cum. She was amazing with my cock in her mouth, and when I told her I was going to cum she told me to stroke myself and cum on her tits. I quickly blew a huge creamy load all over her gorgeous fake tits.

She told me to lay down next to her, and then told me to clean up my mess, grabbing the back of my head and guiding it to lick the cum off of her tits. She gently played with her cock some more while I licked my cum off of her, as she told me to show her that I swallowed it.

After we laid there for a few minutes, she said let's go take a shower. The hotel room had a nice big shower for us to wash each other in. As we bathed, she got hard again, and pushed me down to her knees to start sucking her cock again. She said I was too good at it for her not to cum again. For having already cum in once already, I was surprised when she shot a decent size load in my mouth. I showed it to her and she told me to swallow it.

From there we finally cleaned ourselves up in the shower, dried off and got dressed. I walked her to the door, we kissed and said goodbye. A little while later, I got another message from her, she said thanks for such a fun time and she was already stroking her cock thinking about the fun time we had together!

This story happened this past year! It was real late on a chilly night in the fall, I had just met a guy from grindr at his apartment for a blow and go. After swallowing a nice load of cum, I got in my SUV to drive home and I saw I needed gas. It was well after midnight so I figured gas stations would be empty. There was no one at the gas station I stopped at--perfect.

As I stood there in my black velvet heels, shiny tan stockings, denim miniskirt, tight black sweater, and blonde wig to pump gas, a black sports car with dark window tint, either a mustang or a camaro I don't remember exactly, pulls into the gas station. It did a lap around all of the pumps, then it slowed down and did another lap, I figured the driver had to be checking me out!

As the car passed by me the second time I turned to smile and give a little wave. The car then drove over to the farthest corner of the parking lot and parked. I got back in my car and I just happened to check grindr, and I had a message--it said fuck is that you at the gas station with the white suv right now?! I replied yes, and asked if he was the black sports car. He told me to come get in his car. I drove over and parked next to him.

I got in his car, he was a younger guy in his early 20s. He already had his seat reclined all the way back. He said the moment he saw me he knew I was a CD and had to see if I was on grindr and couldn't believe it was really me.

It was a tight space but with his help I pulled his joggers down and was met with a nice bulge in pink satin panties! I rubbed his bulge for a moment and said oh now I know what turns you on! I pulled them down just a bit and his hard cock sprung out. Despite the awkward space I sucked him as I rubbed his balls still in his panties.

He started watching porn on his phone, and after that it didn't take him long at all before I felt his cock throb and he started squirting his nice warm cum in my mouth. It wasn't the biggest load ever but I was happy to get it anyway! I swirled his cum around the head of cock with my tongue before I sucked it up and swallowed it.

He laid there and said fuck you're the first crossdresser I've gotten head from, you're the best I've ever had. I replied of course, crossdressers always give the best head. I pulled the visor down to adjust my wig, I told him thanks for the cum, then I got back into my car and went home to finish myself off thinking about the two cocks I had that night!

This story is a little long but if you read it you'll see why. It starts out like many of my other stories--it's the weekend, I'm feeling horny, so I posted an ad online and updated my status on grindr and some other apps I'm on. Then I went and got ready for a night of fun while the messages came in. I had a plan this time! Where I lived at the time, there were plenty of hotels nearby. I specifically said I was looking for visitors to the area staying in hotel rooms, and that I would be arriving already dressed up. As much as I enjoyed getting fucked I said that night I was just looking to suck dick.

After getting all smooth in the shower, I got my butt plug in then I picked my outfit--I went with a blue lace bra and panty set, suntan pantyhose, red miniskirt and matching red pumps, and a low cut black top. I put my breastforms in my pushup bra, did my makeup, and finished with putting on a black wig, then I checked at my phone. My plan worked--I had tons of messages!

The first guy sent a cock pic and he was only ten minutes away, and said he hadn't cum in a week. I asked which hotel and his room number and once he sent it back, I grabbed my car keys and was out the door. He messaged me while I was driving and said to send another pic to get him horny. At a stop light I snapped a selfie blowing him a kiss, and he replied damn you got me hard already.

At about 9:30pm I parked and made my way up the stairs to his room, this was the kind of motel where all the rooms have their own exterior door--my favorite kind of motel!

He opened the door and I entered the dimly lit room. He pulled he shorts off and got on the bed, sitting upright against the headboard. He wasn't joking when he said he was already hard! I went to the foot of the bed, and crawled towards him--I spread his legs apart, laid down and started kissing and licking the tip of his cock. He kept whispering to me, "oh fuck yeah" and "fuck you're good". I hadn't even gotten him all the way in my mouth and he was telling how fast I was going to make him cum. The moment I started stroking him and got his cock nice and wet he erupted a massive load in my mouth--try as I might I couldn't swallow it all as he gave it to me. I kept sucking as his cock throbbed in my mouth. He said "fuck that was good head". I wiped the cum that was left on my chin and licked it off my fingers. I asked him if I could go over to the bathroom to clean up quick. I cleaned up, and touched up my makeup and lipstick. As I went for the door I told him I loved it and said goodnight.

I was back in the car right around 10pm. With the taste of his cum still in my mouth, I was still incredibly horny and I wasn't done yet! I checked my phone to see who else messaged me. The next guy I chose told me in his first message which hotel and it wasn't far, not even ten minutes. I asked if he still wanted me to come over and if he could send a cock pic. He responded right away with the pic and his room number, he told me he needed a little sissy slut to take care of him tonight.

Luckily, he was staying at the same kind of motel--all exterior doors to rooms. He was on the third floor, and as I was going up the stairs there was a group of guys on the second level outside a room smoking. One of them spotted me, and motioned to his buddies to look my way. They were pretty far but close enough to see me in my miniskirt and 4" heels going up the stairs. It was a rush being seen like that!

As I got closer to the room, there was a lone guy standing out the balcony vaping. Turns out it was he was my next date! He was wearing sweatpants and a hoodie. He told me I look even better than my pictures, and he took me into the room. We went over to the bed, and when he dropped his sweatpants to his ankles I was surprised to see he was wearing black panties and black thigh high stockings! He asked if that was ok with me and I told him I thought it was hot. I got to my knees while he stood there and I rubbed his bulge over his black panties. I pulled them down just enough for a nice, average size cock to spring out in front of me. I started licking his cock from the base, making my way to the head and started to suck him, rubbing his balls still in his panties and his leg with my other hand. He said I can tell that turns you on doesn't it, I continued to stroke him but I took his cock out of my mouth to tell him I loved a cock in panties, then I promptly resumed sucking him. He told me to keep sucking like a good little slut as he put his hands on my head to control me going back and forth on his cock.

With his hands guiding me, I began rubbing both of his legs up and down, feeling his ass in panties. I found out that's what turned him on, because as my hands got closer to his tight hole he said shit you're going to make me cum already. I moaned and he pulled me onto his cock even more, I gagged just a little but then he started squirting his cum into my mouth and let go of my head so I could keep sucking at my pace. This load wasn't as big but it still felt amazing to get another mouthful of cum. I cleaned him up as best as I could, then I pulled his panties back up over his still semi hard cock. He fell back onto the bed and told me I was a good little slut, and I could freshen up in the bathroom if I needed to. I put on some more lipstick and had to touch up my makeup a little bit since my eyes got a little teary from gagging. Once I was done I walked out, he was still laying on the bed. Before I left I stood in front of him and leaned over to run my hands up his legs and give his bulge in panties a gentle kiss. He stood up and walked me to the door, and slapped my ass as I walked out. The guys who saw me going up to the room were still out there as I left. They saw me leaving as well, and I could feel them watching me walk all the way back to my car, but nothing else happened with them.

It wasn't even 11pm yet so I sat in my car for a few minutes scrolling through the messages, trying to decide if it was time to go home or find another guy! One guy's message caught my eye, he sent me a pic of a nice thick, smooth cock. I messaged him back, and where he was staying was about 25 minutes away. I hesitated because that was a bit of a drive and although I was pretty sure this guy was for real, I've had guys flake on me in the past. I decided to make the drive, I was having too much fun that night to stop and his cock looked absolutely amazing.

I get to the hotel, but this one doesn't have exterior facing rooms, so I'd have to go through the lobby! I was pretty nervous because I hadn't really been out in any public place like a well-lit hotel lobby before. I said screw it, built up the nerve, and walked across the parking lot to the front doors. But they were locked because it was late at night and only guests could get in! I went back to my car and messaged him, he told me he'd meet me at the side door. He told me which one and told me once he was the the door waiting. I drove over to the side entrance, and walked to meet him. He opened the door and said you must be my date tonight! I said yes I am and told him my name. He told me his, put his arm around my waist and we walked up the stairs to his room. He complimented my outfit and said I walk great in heels, he said he wished his wife dressed the way I do for him. I was surprised to hear him tell me he was married, but it was common for guys I had been with in the past.

In the room, he closed the door and came up to me, running his hands up and down my arms, then he pulled me by the hips towards him, grabbing my ass with both hands. He kissed me deeply, and I wondered if he knew I already had two cocks in my mouth that night! I could feel his wonderful cock beginning to grow under his jeans, and he quickly guided my hand to his bulge. He walked me backwards towards the bed and sat me down. I thought we were going to get started but he sat down next to me to kiss me some more as I rubbed his now very hard cock over his jeans and he ran his hands over my nylon covered thighs.

I started undoing his jeans when he stood up to help me get them off, then he said wow you really want this don't you? I responded it's all I could think about during the whole drive! He told me he liked that as he pulled his underwear down to reveal my reward, and nice thick cock with a beautiful shape, probably around 7 inches or so.

I immediately started sucking him, savoring the feeling of the head sliding past my lips into my mouth. Right away he said damn my wife could learn a thing or two from you about giving head. As I got more of his cock in my mouth he said I looked hot with his cock in my mouth. He pulled it out of my mouth and told me to come suck him over on the couch. As I stood up he told me to get on my hands and knees and crawl to him as he walked to the couch. I happily got to the floor, he sat on the couch and stroked his cock and I crawled towards him.

"That's a good cocksucker, come and get it" he said as I neared him. Before I continued to suck him, he told me to pull my skirt up around my waist so he could see my ass. I eagerly did, and turned around and wiggled my ass for him. He leaned forward to rub my ass, putting his hand between my legs to find my bulge. He then run his hands back up to my ass and felt my plug.

He said he liked that I was plugged like a good whore and told me to keep sucking him. I got as close to the couch as I could and sat between him, rubbing one of my legs against his ankle as I sucked him faster and faster. I could feel him tensing up so I knew he was getting ready to cum. He pulled my head up and told me to open my mouth as he stroked in front of my face. I was more than happy to take a facial from him and I hoped he was going to give me a nice big load.

I closed my eyes, opened my mouth and stuck my tongue out a little, barely touching the head of his cock. He moaned and I felt the warm ropes land on my face and tongue. He rubbed his cock on my face and I put his cock back in my mouth to get the last bit of cum from him. I opened my mouth for him to show his cum on my tongue. I swallowed and opened to show him I did, he responded fuck you're such a good slut, he then told me to be a good whore and wipe the rest of his cum into my mouth. He watched as I sat on the floor in front of him licking his cum off my fingers.

He went to get dressed and I grabbed my lipstick out of my purse. He said no don't put that on, I want you to walk out of here just as you are so anyone who sees you will know what kind of whore you are. I pulled my skirt back down, adjusted my wig, and he opened the door for me. I told him thank you and was on my way.

It was past midnight, and even though I had more messages I decided it was time to head home. At home I messaged some guys to see how many more nights they'd be staying for so we could set something up. I passed out on my bed still dressed up and with my plug in me. When I woke up a few hours later, I jerked off all over myself and fell back asleep for a bit.

When morning came, I went over to the mirror and looking back at me was a crossdresser slut with messy makeup who had a fun night of sucking dick and eating cum!

a guy from out of town had found me on grindr and we started chatting, he and his trans girlfriend were going to be in my area for a few nights and wanted to host at their motel room. He told me they were looking specifically for crossdressers to enjoy, and that he was talking some others so there might be some group play. I told him I was absolutely up for it! I asked him if it was cool if I showed up already dressed up and he said they preferred it that way! It's always such a rush to be out in public all dressed up, even though for me it's almost always late at night to meet someone for a hookup.

I wore a blue miniskirt, black thigh high stockings, patent black pumps, and a leopard top. Underneath I had a matching red bra and panty set with my d cup breastforms doing their thing stretching out my top! I parked in the motel parking lot, checked my makeup in the mirror, touched up my lipstick and I headed towards the room! I always loved the feeling of cool night air on my stockinged legs and the distinct tapping of high heels on the pavement!

In the room, it was just the two of them. He opened the door and was only in his boxer shorts, and she was laying on the bed in sexy black lingerie, gently stroking her cock. They had some porn playing on the tv from their computer, mostly compilations of TS with guys fucking each other, so I knew what turned them on!

He took me over to the bed and asked his GF what she tought about the little slut he found for them. She responded that he did a real good job, and all she said to me was "you know what to do now". When I turned my head back towards him he grabbed my ass and pulled me towards him, he started kissing me swirling his tongue in my mouth and guided my hand to already growing cock over his shorts. He pushed me down on to the bed, and took his shorts off so his hard cock could spring out for me. I started sucking him when she took my left hand to start stroking her.

It wasn't long before he took his cock out of my mouth and motioned for me to get up. I stood and he turned me around, I kneeled on the bed and he pulled my skirt up. He spread my legs and stood in between them to rub his cock on my lacy panties while I continued to stroke his GF's cock. She was nice and thick, he wasn't as big but certainly enough for what I wanted!

He started to pull my panties down and I helped him get them down to my knees. That's when I felt him guided his cock to my ass--I helped him get to the right spot and before I knew it he was in me, putting his arms under mine to grab my fake tits and pulled me all the way on to him. All I could do was moan as I felt his cock fill me up.

Still kneeling on the bed but upright with him in me, he took my chin to turn my face towards him so he could kiss me some more as he pumped his cock into me. All while his GF watched and jerked off.

He stopped kissing me and pushed my upper body down towards his GF, I knew exactly what he wanted me to do. As he fucked my ass harder and harder, I took her hand away from her cock and started sucking it for her.

She put her hands on the back of my head to control me going up and down on her cock. She was absolutely packing, she had a nice thick, long cock--one of the biggest I've ever had. I tried my best to get it all. With him fucking me hard, I had use of both hands to stroke her.

As he fucked me, and I sucked her, he leaned over and they started making out. My mouth and ass full at the same time--it was amazing.

She told her boyfriend, "this little whore is going to make me cum!" and he said "me too, i bet this little slut wants me to cum in her!"

All I could managed was a muffled mmhmm with both of them in me. She came first, exploding an absolutely massive load into my mouth, holding my head down onto her cock as she pumped her thick cum. I swallowed as much as I could and then licked up what I couldn't, while he was pounding my ass harder and harder.

Then, he grabbed my hips and pulled me as hard as he could onto his cock while he groaned and his cock throbbed, filling me up with cum. He put his arms around me, grabbing my fake tits and pulled me up so he could kiss me more while he made his last pumps into me.

We both fell forward onto the bed, with him still in me. She moved towards the middle of the bed, and put her still semi-hard cock in my mouth. I laid there, him on top of me, and in me--and her cock in mouth as I gently sucked on the swollen head of it.

He eventually pulled out of me and went to the bathroom to clean up. She told me to come lay next to her, which I did. We chatted for a little bit, mainly her asking about how I started crossdressing and when I started sucking dick. She asked if we could take a picture together, so I did my best to put myself back together, grabbed some lipstick from my purse to touch up, and we took some selfies together. He came from the bathroom and was checking his phone to see if anyone else was going to join us. They had a few responses but no one else who was on the way.

It was getting late so I thanked them both for an amazing time and I said I had to get home. I told them if they were interested during their stay I'd come see them again!

I didn't realize how horny I still was--during my drive home I was on grindr to see if anyone needed a quick blowjob but no luck! But that will lead me to the next story I post! Hope to see you there!

-Stefanie xoxo

I was all dressed up on a friday night--tight black miniskirt, fishnet stockings, pink pumps, and a pink lace top. I just got my new d cup breast forms and loved how they looked in my pushup bra. I was on grindr trying to find a guy who needed a crossdresser slut to take care of him.

I started chatting with a guy only a mile and half away who said he could host. He sent me the location and I told him I'd be there in 10 minutes. I got my butt plug in, and I drove over to his neighborhood, but there was only street parking so I had to park around the corner from his place. I parked, got out of my car, and switched from my flats to my heels, I grabbed my purse with my hookup essentials and started walking towards his house.

I was walking down the sidewalk when a car I was approaching started up, turned its lights on, and pulled away! I was a little surprised but it was late at night and I didn't care that they saw me. When I got to his house he was waiting outside in front of the door.

He asked if had seen his last message on grindr, and I said I hadn't checked since before I left my house. He said he wanted me to wait a few minutes--that was his sister and her friend in the car that started up and pulled away! Of course I apologized but I told him I'd still suck his cock if he wanted. He reluctantly accepted and we walked to the street where his van was parked. I had never done anything in car but, I felt bad he may have been found out by his sister, and I needed some cum!

We got in the back, and he took his phone out to watch gay porn so I pulled his pants and underwear down to his ankles. He had a pretty average cock but that was enough for me. I sucked him for a bit when he told me to turn around. I maneuvered around when I felt his hands run up the back of my thighs, to my skirt which he pulled up to my waist. He started feeling my ass when he felt the base of my plug. He pressed on it with his thumb and his other hand reached under me to feel my bulge in my lacy panties. He said he wanted that ass next time and told me to keep sucking his cock.

I turned around and eagerly resumed sucking his cock, before long he said he was going to cum and I lifted my head just for a moment to tell him he could cum in my mouth. As soon as I got the head of his cock in my mouth he exploded a nice load into me. I swallowed it all, licked up and down his cock to clean him up, and then we got out of his car.

I told him again I was sorry about his sister possibly seeing us but I assured him that I was the gay one for dressing slutty and sucking cock, not him ;)

This is a short version of the very first time i dressed up and sucked cock. I'll remember it always because it was on new year's eve, quite a few years ago. My roommate was out of town so I had the townhouse to myself, and NYE wasn't that big a deal to me so I spent the night in, and got all dressed up. Being December, and cold, I went with shimmery tan tights, with fishnets over them, black strappy pumps, and denim miniskirt, a white turtleneck sweater, with purple bra and panty set underneath it all.

I was just beginning to fully dress up, outfit, wig and makeup. So I was feeling fairly confident and more importantly, horny. After a few drinks I posted my ad on craigslist, saying I was looking for a guy to come over for a quick blowjob. I was getting late at night so I knew guys would be looking for head if they didn't find anyone, and oh was I right.

The guy I picked to come over sent a pic and said he was 15 minutes away from where I was. I dimmed all the lights and waited by the front door for him. I was literally trembling in my heels looking through the front window! Then he pulled into the driveway.

I brought him into my living room, and sat down on the couch with him standing in front of me. He dropped his pants to reveal a nice, thick 7 or 8 inch cock, already getting hard. As soon as I slid the head of his cock over my red lips I knew from that moment on I was destined to be a crossdressing slut for men. I loved feeling his cock go from semi to raging hard in my mouth as soon as I started sucking him.

He grabbed my head with one hand to guide me back and forth on his cock. I stroked the base of it as I worked the upper half, swirling my tongue around it. It wasn't long before he tensed up and filled my mouth with cum in an instant. It was amazing to feel the cum squirt in bursts into my mouth, I swirled my tongue around it before swallowing it and cleaning his cock.

We didn't speak much during the hookup but after I was done he did say that was damn good, thanks. I stood up and walked him back to the front door and he was on his way.

It dawned on me that I was then officially a little CD slut! Then I went and checked my messages to see who else responded to my craigslist ad!