I’ve been a femboy/sissy for a bit now and while I have a solid figure, feminine facial features, and feminine behavior, how else do you all promote a feminine appearance? I still have some muscles and definitely am more on the femboy side so I want some help to go full sissy.
So this summer I went on a cabin trip with some friends. It’s mostly girls and a few guys. I’m kinda new to the friend group but they still invited me. Anyways I was getting out of the shower naked, completely limp, and one of the girls accidentally walks into the bathroom. I scream and coverup as she runs out. I get dressed and quietly tiptoe to the stairs. In the living room I can hear all the girls gossiping. She said things like “it’s the smallest dick I’ve ever seen, he had no body hair, his ass looked like a girl’s, my boyfriend would kill him with a single punch.” As they all laughed and humiliated me I felt my clitty get insanely hard. My sissy senses came over me, so I tucked my hard clitty and came downstairs. They told me they were all leaving and I said I had some stuff to get done at the house. When they left, I sprinted upstairs, got dressed up, and fucked the shit out of my dildo, thinking about how embarrassed I was the entire time. I sissygasmed twice and laid happily in my cum until they came back.
I need help. My neighbor has a new twink or sissy over every week and we’ve sometimes exchanged glances and I think he notices my feminine features. I’ve heard him destroying boy holes in his apartment and he’s DEFINITELY heard me sissy gasming. There’s so much tension but he has such a big roster he probably doesn’t even care if I come on to him. I’m debating knocking on his door caged up in lingerie but idk. What should I do?!
I’ve been a sissy for a bit now and have had a few cocks and a few doms but I’ve never been outside for an extended period of time in my outfits or tried to just go out and meet a guy in public. I had been locked for 2 weeks a little bit ago and I was losing my mind on dating apps. I hit up my sissy friend and she said I should accompany her to the local book store. I was confused but she said she meets a lot of guys there and told me to come dressed. I was nervous but eager to advance in my training so I powered through and got ready.
She pruposefully did not tell me it’s an infamous hookup spot with dedicated rooms in the back. I get there and I quickly learn that book store is lingo for sex shop lol. I’m shaking with nerves as we walk in and to take the edge off I check out sex toys and even buy a few.
The entire time we’re getting looks from guys in the store and I feel my nerves fade. She then tells me about the rooms. I can feel myself leaking as we walk to the back. We leave the “normal store” and enter a dark room that almost looked like a nightclub. It was a big lounge with a mini bar, couches, people hanging out and making out. Past the lounge are a bunch of small rooms with mini windows on the doors.
My friend tells me she comes here almost every weekend and gets used by multiple guys. I was honestly mad that she never shared it before. Anyways we get a drink each and sit down at a table. Groups of ppl are meandering around and most of them seem straight until a group of bigger, hairy guys walk in and I can immediately tell they’re interested. They come over with a round of drinks for us. I start getting tipsy and incredibly flirtatious with one of the guys (the fattest one). He starts rubbing my thighs and before I know it we’re hardcore making out in front of everyone. I feel his hand start to grab my cage and I feel my sissy persona completely wash over.
His friends and Mine start laughing and suggest that we split up. 2 guys with each of us. I get led to a room and we walk in to a dim room with a cheap couch, some cleaning supplies, and some things for bondage. I get on my knees and begin to suck them off. I’m having a blast and before I know it, I’m getting spit roasted. The other friend was fucking me first and came really quick on top of my ass so he just watched the rest. The fat guy had crazy stamina.
He slapped me, choked me, tied my arms together, put me in dog, missionary, prone bone, and a few more. Feeling his weight crush me made me sissygasm twice. I was already covered in cum downstairs so he pulled out quickly and came on my face with no warning. He caught his breath and they both just massaged me and admired all the cum. He petted my head and told me he’s there every Saturday and that if I want to continue to serve him, I’ll walk out of this place without cleaning the cum off. I happily agreed and we went to check on my friend.
She was getting much freakier. She was getting hit with belts, whips, and covered in even more cum when I went into her room. Once they finished we all walked out as a group, covered in cum, and they patted us on the ass as a goodbye. We drove back to my place, watched some hypno, jerked eachother off, and cleaned up. I’ve been back a few times and even been with upwards of 4 guys in a day there. 10/10 experience, I’ve found my new home.
When I was a couple months into my feminization training, my online dom decided it was time to attempt my first sissygasm. I was really nervous but whatever he said went. I had had some intense anal sessions by then but it usually got too painful before I could cum.
He ordered a larger dildo, poppers, handheld fuck machine, and a lot of lube to my apartment. I had a few drinks and then I hopped on a call with him. We started with some minor foreplay and I had already been plugged for 3 hours at that point (caged for a week).
I grabbed my medium dildo and began to warm myself up. He had me go much slower than usual as he really wanted to open my sissy hole wide. He was being particularly dominant and commanding so that I wouldn’t chicken out. He told me if I don’t sissygasm tonight, he’d keep me caged for a month. I was determined.
After about an hour and a half of sensual dildo play, orders, poppers, and sissy hypno He told me it’s time to step it up. I grabbed the handheld machine, attached the dildo, and began. He had me up the pace every 5 minutes and take a break every 10. I was moaning and squirming and so gooned out as I felt my hole go numb and a load start to build.
After 40 minutes, he instructed me to put it on the fastest setting for 3 minutes. This made my hole hurt so fucking bad but this was by far the farthest I had ever gone.
Instead of giving me another break he told me to suction the 8.5 inch dildo and begin riding. He told me I could change paces but that dildo wouldn’t leave my ass until I sissygasmed.
He sent me his favorite sissy hypno videos and I got to work with him watching me the entire time. I felt the work from the Machije fade for awhile until he instructed me to stop being a faggot and ride harder. I rode the hardest I ever had for 30 minutes straight and then sat on the dildo and caught my breath. I could tell I was close.
“Good girl. This will be your final round. If you don’t sissygasm here I may never unlock you. If you stop riding at all I’m hanging up.” I felt my body tingle is I got excited to finally do it. I rode that dildo for roughly another hour. No breaks at all. I was drooling, drunk, shaking, gooned out, but I didn’t care. I couldn’t stop.
For the last 5 minutes I rode as hard as I could and I could finally feel my prostate clenching up and a load building up in my clitty. I rode and rode and without even realizing it, giant ropes were shooting out of my cage. He told me to keep the pace up or the sissygasm will be ruined. I kept going as I felt the most blissful release of my life.
No post nut clarity, no aching, no sore asshole. Just pure bliss. After everything was out he watched me cleanup and told me tomorrow I’d be allowed to unlock myself and jerk normally. My asshole was sore later (duh I fucked it for 4 hours) but not nearly as bad as it should have been. I can’t explain a sissygasm but it is quite literally the best feeling a sissy can have. Thanks for reading!
So I got fully feminized by my first gf and after we broke up, I went on the hunt for a dom. I was super into one video call sessions and then being done but then I met a guy (let’s call him dom) who was different. He genuinely wanted to build a relationship and had creative tasks and wants from me. We met on Reddit and instead of having a horny video call he told me to get dressed and he just wanted to talk. We talked for hours and he made me do various sfw tasks, all the while complimenting me but also being stern. I didn’t even realize it was a 4 hour call by the time I went to bed.
I woke up the next morning and without even realizing it the first thing I did was text him. I was hooked. His deep voice, hairy chest, big forearms, his calmness, and his presence all took a hold of me. I couldn’t help myself. That night we had our first real session. It was sensual and slow but it was phrases like “use your words” and “slowly push your limits girl” that made me get so turned on.
Things started to ramp up. Our sessions got freaky (anal bead freaky) and we started having normal conversations throughout the day. He started sending me clothes, toys, and more. The big step was him buying me a vibrator that he could control from his phone. He would make me wear it in public and he’d buzz it if I took too long to respond to a text.
He started to include his friends in some of the calls and started buying me really expensive clothes. Come to find out dom is a married successful business owner so he really started to spoil me.
Then one day he says he has a big request. He says he wants to fly me out (a couple of states over) and make me serve him for the weekend. I get nervous. A year and a half before I was afraid to even put fingers up my ass and now I’m about to take fly to a guy. I said I’d think on it and it’s then that I remembered the day my parents walked in on me getting fucked (different story on my account lol. It was a few months prior). I had only taken 2 dicks at this point and that one was the only one that lasted more than 2 minutes. I was a novice and this was a big step.
I said yes. I told everyone it was a conference for school and I’d be staying in a hotel. I packed all of the nice stuff he bought me and got on a plane the next day. The whole time he was telling me of his sfw plans for us but kept all the nsfw stuff secret.
I’m in semi-feminine clothing on the trip and am wearing my chastity cage and butt plug the entire time. He makes me send him constant updates so he knows I’m safe, and I even snap a sexy pic in the plane bathroom lol. I land and my heart is racing. I know he’s a good dom and trustworthy but I couldn’t stop my heart rate.
I get into the terminal and I freeze. I see a tall hairy man, biceps the size of my head, nice slacks and shirt, expensive watch, tattoos on his leg, bald head, and a big beard. I feel myself leak and quiver.
He walks up to me, doesn’t say a word, and hugs me. I start to go weak as he pulls me tight and smells my hair. “How was the trip my good girl. Calm down it’s ok daddy has u now”. I feel my nerves go away.
We walk and talk casually to his car. He tells me his wife is gone for a week and how his marriage is on the downslope. Before we get to the car he has me go into the bathroom and dress full sissy (not nude obv). I come out of the bathroom and a big smile goes across his face.
We get into his car and he puts his hand on my thigh as we drive. We get to the grocery store and he gives me a list. He tells me to grab everything on that list and he’s gonna buzz me every 5 minutes to remind me who I’m doing it for. I happily agree. After that we get to his house where he has me fully strip and clean his house while he cooks dinner. I felt so feminine and sexy it was amazing.
He makes me sit semi on his lap and feed him his dinner and then he lets me eat mine. He has me do some other various tasks and then he tells me to get back into my sissy outfit. He instructs me to go and tie myself to his bed while he showers up. I can’t contain my excitement.
He comes out of the bathroom fully naked and I feel my clitty pulsate. He puts on sissy hypno at full volume and begins to caress and spank me. We start kissing and I can feel him plapping my cage. After a good 45 min of foreplay he pulls out a big box of toys.
He ties up my hands and feet, puts a choker and leash on me, and grabs a dildo. He rims my asshole for a bit and begins to slowly fuck me with the dildo. He had trained me so much at this point I did great but I was nervous about taking the real thing. He had shown me videos of him fucking sissies and teinks and he is extremely powerful.
After my asshole is extremely warmed up and I’m Gooned out, he begins to fuck me slowly in doggy. His moans and words of affirmation send me into another planet. Then with no warning, he goes full speed hard. I feel every muscles shake as he slams me into the bed, over and over and over. Everything goes weak and he doesn’t slow for what must’ve been 5 minutes straight. He abruptly pulls out and I let out the biggest moan of my life. He quickly flips me and shoves his dick in my throat. I’m not too good with bjs so I’m nearly choking with every thrust but I pull through for dom. He pulls out after a bit and tells me how good I’m doing.
“This is just the warmup session for tomorrow and Sunday so I’m not gonna drag this on too much. Do you think you can take one more hard round of prone bone my sweet girl.” I nod my head cuz I can barely speak and he flips me. He once again starts fucking my at an absurd pace with his big arms wrapped around my neck. I feel his entire body weight crush me into the mattress with each thrust. My feet are kicking furiously as he grunts louder in my ear. We were so fucking loud but neither of us cared.
He pulls out and begins to fuck me missionsry and hit my cage. He ruins my orgasm a few times and then he picks up his pace. Once again I’m so gooned out I didn’t even feel him pulling out and kneeling over my face. He furiously jerks his dick as he pulls my leash tight and before I know it he’s dropping a giant load all over my face. We both catch our breath as I lay there ruined, cum all in my hair and eyes.
“U served well girl. But don’t think I just brought you here for some basic doggy. Tomorrow will be much more interesting. Lay there for 45 minutes and catch your breath while I shower. I’ll unlock you after that and clean you and put you to bed.”
(I’ll post the details of that night and the wrest of the trip soon)
So I got fully feminized by my first gf and after we broke up, I went on the hunt for a dom. I was super into one video call sessions and then being done but then I met a guy (let’s call him dom) who was different. He genuinely wanted to build a relationship and had creative tasks and wants from me. We met on Reddit and instead of having a horny video call he told me to get dressed and he just wanted to talk. We talked for hours and he made me do various sfw tasks, all the while complimenting me but also being stern. I didn’t even realize it was a 4 hour call by the time I went to bed.
I woke up the next morning and without even realizing it the first thing I did was text him. I was hooked. His deep voice, hairy chest, big forearms, his calmness, and his presence all took a hold of me. I couldn’t help myself. That night we had our first real session. It was sensual and slow but it was phrases like “use your words” and “slowly push your limits girl” that made me get so turned on.
Things started to ramp up. Our sessions got freaky (anal bead freaky) and we started having normal conversations throughout the day. He started sending me clothes, toys, and more. The big step was him buying me a vibrator that he could control from his phone. He would make me wear it in public and he’d buzz it if I took too long to respond to a text.
He started to include his friends in some of the calls and started buying me really expensive clothes. Come to find out dom is a married successful business owner so he really started to spoil me.
Then one day he says he has a big request. He says he wants to fly me out (a couple of states over) and make me serve him for the weekend. I get nervous. A year and a half before I was afraid to even put fingers up my ass and now I’m about to take fly to a guy. I said I’d think on it and it’s then that I remembered the day my parents walked in on me getting fucked (different story on my account lol. It was a few months prior). I had only taken 2 dicks at this point and that one was the only one that lasted more than 2 minutes. I was a novice and this was a big step.
I said yes. I told everyone it was a conference for school and I’d be staying in a hotel. I packed all of the nice stuff he bought me and got on a plane the next day. The whole time he was telling me of his sfw plans for us but kept all the nsfw stuff secret.
I’m in semi-feminine clothing on the trip and am wearing my chastity cage and butt plug the entire time. He makes me send him constant updates so he knows I’m safe, and I even snap a sexy pic in the plane bathroom lol. I land and my heart is racing. I know he’s a good dom and trustworthy but I couldn’t stop my heart rate.
I get into the terminal and I freeze. I see a tall hairy man, biceps the size of my head, nice slacks and shirt, expensive watch, tattoos on his leg, bald head, and a big beard. I feel myself leak and quiver.
He walks up to me, doesn’t say a word, and hugs me. I start to go weak as he pulls me tight and smells my hair. “How was the trip my good girl. Calm down it’s ok daddy has u now”. I feel my nerves go away.
We walk and talk casually to his car. He tells me his wife is gone for a week and how his marriage is on the downslope. Before we get to the car he has me go into the bathroom and dress full sissy (not nude obv). I come out of the bathroom and a big smile goes across his face.
We get into his car and he puts his hand on my thigh as we drive. We get to the grocery store and he gives me a list. He tells me to grab everything on that list and he’s gonna buzz me every 5 minutes to remind me who I’m doing it for. I happily agree. After that we get to his house where he has me fully strip and clean his house while he cooks dinner. I felt so feminine and sexy it was amazing.
He makes me sit semi on his lap and feed him his dinner and then he lets me eat mine. He has me do some other various tasks and then he tells me to get back into my sissy outfit. He instructs me to go and tie myself to his bed while he showers up. I can’t contain my excitement.
He comes out of the bathroom fully naked and I feel my clitty pulsate. He puts on sissy hypno at full volume and begins to caress and spank me. We start kissing and I can feel him plapping my cage. After a good 45 min of foreplay he pulls out a big box of toys.
He ties up my hands and feet, puts a choker and leash on me, and grabs a dildo. He rims my asshole for a bit and begins to slowly fuck me with the dildo. He had trained me so much at this point I did great but I was nervous about taking the real thing. He had shown me videos of him fucking sissies and teinks and he is extremely powerful.
After my asshole is extremely warmed up and I’m Gooned out, he begins to fuck me slowly in doggy. His moans and words of affirmation send me into another planet. Then with no warning, he goes full speed hard. I feel every muscles shake as he slams me into the bed, over and over and over. Everything goes weak and he doesn’t slow for what must’ve been 5 minutes straight. He abruptly pulls out and I let out the biggest moan of my life. He quickly flips me and shoves his dick in my throat. I’m not too good with bjs so I’m nearly choking with every thrust but I pull through for dom. He pulls out after a bit and tells me how good I’m doing.
“This is just the warmup session for tomorrow and Sunday so I’m not gonna drag this on too much. Do you think you can take one more hard round of prone bone my sweet girl.” I nod my head cuz I can barely speak and he flips me. He once again starts fucking my at an absurd pace with his big arms wrapped around my neck. I feel his entire body weight crush me into the mattress with each thrust. My feet are kicking furiously as he grunts louder in my ear. We were so fucking loud but neither of us cared.
He pulls out and begins to fuck me missionsry and hit my cage. He ruins my orgasm a few times and then he picks up his pace. Once again I’m so gooned out I didn’t even feel him pulling out and kneeling over my face. He furiously jerks his dick as he pulls my leash tight and before I know it he’s dropping a giant load all over my face. We both catch our breath as I lay there ruined, cum all in my hair and eyes.
“U served well girl. But don’t think I just brought you here for some basic doggy. Tomorrow will be much more interesting. Lay there for 45 minutes and catch your breath while I shower. I’ll unlock you after that and clean you and put you to bed.”
(I’ll post the details of that night and the wrest of the trip soon)
I was a normal boy until I was 18. Never had sex but then I finally got a gf. Things started slow and she always pushed away the idea of sex. Then one night she tells me to come over. I think this is finally it. I get there and we have a few drinks and then she leads me to her bedroom. When we walk in, she has a tranny porn video on the tv that I watched 3 nights prior. She explained how she saw my search history and I thought she was bouta breakup with my ass. Instead she told me to strip and tie myself to the headboard. She did my makeup, put on a wig, put me in a dress, and began to jerk me off. Then she suddenly started fingering me. I didn’t even know why I agreed to this but I didn’t care anymore it felt so good. I came so quickly and she just laughed and made me sit in it. From there on out I was her good little girl. We’d have normal sex from time to time but she was determined to make me into a sissy. I enjoyed it more and more. It got to the point where she was making me wear vibrstors in public and she’d buzz it if I disobeyed. I even started to look more feminine. Unfortunately everything fell apart when we tried to order some estrogen and my parents found out. She started me on my sissy journey and I still keep her updated on my journey. She’s even had a few threesomes with me now that it’s a few years later.
So my parents have kinda known I’m into guys but they’ve never known I’m a sissy. Anyways they planned a surprise visit and lucky me it’s the same night a guy from Grindr is coming over. I’m all dolled up (makeup, wig, dress, heels, socks, u get it). Me and the guy go out for some drinks and right away I can tell he’s dominant and isn’t some DL scared guy. He is openly making me be submissive in public (this is important later). Anyways I get tipsy and we go back to my place. We have another drink and he wastes no time. Makes me grab my bondage and toys and starts warming me up. I start sucking his dick and it’s pretty normal sex to start but he gets real rough. He starts slapping the shit out of me and going really hard. I’m so bimbo’d out I don’t even realize that he is choking me as hard as he can, pushing my head into the sheets, and fucking me doggy at an incredible pace. Right at this moment my door opens and my fucking parents walk in. I’m so out of it but I see them and try to push him off. They scream and he stops for a moment. We kinda just stare at eachother in shock and then I feel a hand wrap around my neck and he pulls me up straight, still with his dick in my ass. He’s hugging me and grabs my limp dick and says “look at how useful ur little boy is to me.” My parents start cursing and storm out and I can’t even muster up the strength to push him off. He keeps fucking me and laughing and I start laughing too. He starts making comments while he rails me about how I’m such failed little boy. Next thing u know he cums on my face and leaves. I sat there for awhile and didn’t know what to do but I felt happy. I now had nothing to hold me back. Before I’d only give in when I was really horny but now it felt like I could truly accept my new life. Since then I’ve been a full time sissy. I barely dress masc anymore, ive served multiple men, and i even have a dom that now lives with me and makes me serve him every night. It was traumatic but probably the best thing to happen to me.