Transvestite sex stories
Michael to Michelle 2- Glory hole revelation by SonicRush66
Since my first gay experience at the sex shop, not much has happened, I've been back and forth there, Claire has helped me get some sexy clothing and sex toys and we chatted about how great that evening was. I talked to Gary a few times, wank chatted over cam but not much. But the few months from them events I had started to train my ass with a dildo, completely shaved, lost some of my belly fat, but kept my curvy figure as best I could. Claire even started me on high doses of estrogen tablets w Read more...
Rating: 81%, Read 6227 times, Posted Nov 30, 2022
Fantasy | Anal, Bi-sexual, Blowjob, Boy, Cheating, Cum Swallowing, Gay, Group Sex, Threesome, Transgendered, Transsexual, Transvestite
GEOFFREY AND THE MEGA YACHT by CecilBCK
“We met accidentally on purpose in the showers three times this week. He told me he knows us by reputation and has invited us to be his guests on his mega yacht this weekend. He told me he knew we were both gender fluid and loved having sex with an audience.” “Did he have an erection for you in he showers? Did you have an erection for him? Did he proposition you? I want to know.” “Yes, to all your questions Sarah, he wants to have both of us,” I reply. “He had his hand on my erection when he t Read more...
Rating: 71%, Read 10115 times, Posted Nov 29, 2022
True Story | Asian, Ass to mouth, Bi-sexual, Blowjob, Cheating, Consensual Sex, Cuckold, Erotica, Exhibitionism, Extreme, Female, Group Sex, Hardcore, Lesbian, Male, Masturbation, Oral Sex, Threesome, Transvestite, Voyeurism
Instructor Mike’s Academy - Part 4 - Becoming a Girl by qtaimee
Warning: This is an explicit semi-fictional/semi-autobiographical multipart series involving White Daddy / south asian teen raceplay, crossdressing, and more. If you are not over 18 and/or find the notion of White Cock superiority to be offensive, then please do not read on. Instructor Mike’s Academy - Part 4 - Becoming a Girl Sadly, it was time to head back. I had cleaned myself well in Instructor Mike’s shower, and when my mother came home she was none the wiser to my day’s lesson plan o Read more...
Rating: 50%, Read 6079 times, Posted Nov 24, 2022
True Story | Anal, Asian, Ass to mouth, Authoritarian, BDSM, Boy, Discipline, Domination, Enema, Exhibitionism, First Time, Gay, Humiliation, Interracial, Male, Role-playing, School, Submission, Teen, Torture, Transvestite, Young
SARAH’S FANTASIES by CecilBCK
I was in my mid-twenties when I watched another couple fucking for the first time. Around the same time my then current man took me to a club where we watched one man blowing another man. They were both incredibly attractive and very talented. And the man having his cock sucked had the biggest erection I had ever seen at that stage. The first time I had two men was not long after that when I met them in the bar after a business conference a long way from home. They were both five years younger Read more...
Rating: 73%, Read 6373 times, Posted Nov 18, 2022
True Story | Ass to mouth, Bi-sexual, Blowjob, Cuckold, Erotica, Exhibitionism, Female, Group Sex, Hardcore, Lesbian, Male, Masturbation, Oral Sex, Pissing, Threesome, Transvestite, Voyeurism, Water Sports
My Sissy Son - Part 2 by CumCrazedCanuck
After my son Jason gave me that first blowjob, everything changed completely for us. When I think back to that moment, I knew I should have felt ashamed with myself. But while I was looking at his beautifully messy face and thinking about how we got to that point, I realized I wasn't ashamed. I wasn't upset with myself for being weak like I had been in our previous encounters. I wasn't embarrassed or confused. I was satisfied, content and to put it simply; happy. I was happy because Jason was Read more...
Rating: 78%, Read 18629 times, Posted Nov 02, 2022
Diary | Anal, Blowjob, Cum Swallowing, Gay, Incest, Masturbation, Teen, Transvestite
TEN INCHES FOR ADA. by CecilBCK
“Yes, I have, you know I have.” “I always get a buzz when some of the women I have arranged to have sex with you phone me or send me emails telling me in detail how you fucked them. I have an assignment coming up where that just might be possible.” I work as a male escort for Ada’s exclusive agency. She caters for female and male clients. Often both at the same time. In many cases a much younger trophy wife or lover wants to have a hung, younger man. As a trade off the wealthy man often wants Read more...
Rating: 74%, Read 6812 times, Posted Oct 06, 2022
True Story | Bi-sexual, Blowjob, Cheating, Cuckold, Erotica, Exhibitionism, Female, Group Sex, Male, Mature, Old Female, Old Male, Oral Sex, Threesome, Transvestite, Wife
Danni's Diet by Danni8585
My name is Danni, and I am a part time crossdresser who loves solo times. One such fantasy is making my sex part of my diet. I began watching myself cum in my bathroom with a mirror...that helped me come up with more nasty thoughts. And after my first try with a mirror, uncontrollably shooting my cum on it as bucked and heaved through several orgasms, this time is my epic. As lie back on my sex sheet with a pillow, in front of a door, with a Full length mirror attached. Next to me is my t Read more...
Rating: 38%, Read 2773 times, Posted Sep 24, 2022
Fantasy | Anal, Cum Swallowing, Exhibitionism, Extreme, Female, Masturbation, Solo, Transgendered, Transvestite
Hermia Aphrodite (Chapter 1?) by pANTSU
I sat on the bed, and viewed the marvel before me, close enough to reach out and touch. A sweet oval face, framed by long blonde hair. Long blonde eyelashes too, around massive pale blue eyes, sparking with life and personality. A button nose. Thick, pink, kissable lips. Moving down, a slender neck, high collarbones, and oh, such breasts! Large – maybe the size of grapefruit - and perfectly shaped, hanging deliciously from a pale chest. Further down, a smooth belly, tapered to a narrow waist, w Read more...
Rating: 75%, Read 10311 times, Posted Sep 21, 2022
Fantasy | Anal, Consensual Sex, Erotica, Female, First Time, Gay, Hardcore, Lesbian, Male, Oral Sex, Pegging, Romance, Transgendered, Transsexual, Transvestite
Mum, my goddess 4 by Fatman50
Why does time always slow down when you are waiting for something good to happen? My last lesson seemed to drag on for hours. When the bell finally rang, everyone jumped up, grabbed their bags and crowded for the door, Miss Richards shouting in vain for us not to forget to get out homework in by Friday. I could have rushed straight to the toilet block but l didn’t want to arouse suspicion, everyone else seemed more intent on getting off school property as soon as possible. Also, l was hoping Read more...
Rating: 76%, Read 49170 times, Posted Sep 21, 2022
Fiction | Anal, Ass to mouth, Bestiality, Bi-sexual, Blowjob, Consensual Sex, Cum Swallowing, Exhibitionism, Female, Fisting, Gay, Group Sex, Incest, Male, Mature, Spanking, Teen Male, Transvestite, Young
Suzy Unleashed Chapter 13 by Suzygurl
Suzy Unleashed Chapter 13 It’s been quite a while since I updated my diary, so I need to apologize for that. Some things haven’t changed: I’m still living as a woman, still controlled by my wife, Kathy, and still working as a receptionist/secretary/whore. Some things, however, have changed, and this is the story of those changes. If you’ve read my previous stories, you know that I had learned to accept the fact that I am no longer really a man. Actually, I guess that’s not entirely correct; Read more...
Rating: 64%, Read 4867 times, Posted Sep 13, 2022
Diary | At work, BDSM, Domination, Submission, Transsexual, Transvestite
Mum, my goddess 3 by Fatman50
It must have been a good ten minutes before any of us stirred. Jeff was flat out on his back, Mum was lying beside him, her head on his tummy as she nuzzled his flaccid cock. Dad was sitting up looking at one of Jeff’s magazines while playing with his cock. I crawled over to him to see what was in the magazine, not surprisingly it was full of girls and boys having sex with animals. Some of them looked younger than me. I pointed to one photo of a boy with a Labrador knotted in his bum hole. Read more...
Rating: 76%, Read 88709 times, Posted Sep 11, 2022
Fiction | Anal, Ass to mouth, BDSM, Bestiality, Bi-sexual, Blackmail, Boy, Coercion, Consensual Sex, Cum Swallowing, Domination, Exhibitionism, Group Sex, Incest, Male, Masturbation, Old Female, Oral Sex, School, Submission, Teen Female, Threesome, Transvestite, Wife, Young
Final Feminization VII by [JamesBondage]
Cloud awoke from a long slumber in a haze of grogginess and confusion. His eyes had scarcely begun to open when they shut involuntarily in pained surprise. Wherever he was now, it was bright, sunny and warm. Nothing like the dark city of Midgar and the slums below it. He wasn't used to the brightness. Combined with his headache and nausea, it took a while to adjust. As his mental fog began to dissipate, he sat up and took stock of his surroundings. To say he was taken aback would be an understat Read more...
Rating: 64%, Read 4662 times, Posted Aug 26, 2022
Fiction | Anal, Authoritarian, BDSM, Blowjob, Coercion, Cuckold, Cum Swallowing, Domination, Exhibitionism, Fan fiction, Female, Hardcore, Humiliation, Masturbation, Mind Control, Oral Sex, Slavery, Submission, Transsexual, Transvestite, Voyeurism
SARAH'S CUCKOLD - PART 1. by CecilBCK
For Sarah size is important, she enjoys me flaunting and using my thick, nine-inch erection. She has a magnificent size-fourteen ass on a size-twelve body with thighs to match. She loves being teased and licked. Around once a month she loves having a second man to pleasure her while I enjoy watching and perhaps joining in. To be fair to me we sometimes share another female which we both enjoy. Sarah is of French descent, bilingual, fluent in both French and English and as I recently discovered Read more...
Rating: 59%, Read 4818 times, Posted Aug 03, 2022
True Story | Ass to mouth, Bi-sexual, Black, Blowjob, Cheating, Cuckold, Domination, Erotica, Exhibitionism, Female, Gay, Group Sex, Hardcore, Lesbian, Male, Masturbation, Mature, Old Female, Oral Sex, Transvestite, Voyeurism
Athena Corp Chronicles - Chapter 4 - Best Practices by [JamesBondage]
THREE MONTHS AFTER THE FALL Ian's frown grew more pronounced as he waited his turn. He'd been in line at the security checkpoint for fifteen minutes. He always showed up to work at least ten minutes early. Now, thanks to this spectacle, he was five minutes late and counting. They'd warned him there would be more strict security protocols at the newly established Special Projects Division, but he didn't think it would take this long. The only thing he hated more than being late was someone else' Read more...
Rating: 61%, Read 3169 times, Posted Jul 27, 2022
Fiction | Anal, At work, Authoritarian, BDSM, Consensual Sex, Cosplay, Discipline, Domination, Erotica, Female, Hardcore, Humiliation, Latex fetish, Pegging, Romance, Slavery, Spanking, Submission, Torture, Transvestite
Instructor Mike’s Academy - Part 3 - Is this Love? by qtaimee
Warning: This is an explicit semi-fictional/semi-autobiographical multipart series involving White Daddy / south asian boy raceplay, crossdressing, and more. If you are not of age and/or find the notion of White Cock superiority to be offensive, then please do not read on. Instructor Mike’s Academy - Part 3 - Is this Love? I picked up the note and read carefully so as to not miss anything: “Hello little aimee. As the days go on, your instructions will become more complex but today we will Read more...
Rating: 50%, Read 2443 times, Posted Jul 19, 2022
True Story | Asian, Ass to mouth, Authoritarian, BDSM, Blowjob, Boy, Cum Swallowing, Domination, Exhibitionism, First Time, Gay, Interracial, Male, School, Submission, Teen, Transvestite, Young
Instructor Mike’s Academy - Part 2 - Now I Understand by qtaimee
Warning: This is an explicit semi-fictional/semi-autobiographical multipart series involving White Daddy / south asian teen raceplay, crossdressing, and more. If you are not over 18 and/or find the notion of White Cock superiority to be offensive, then please do not read on. Instructor Mike’s Academy - Part 2 - Now I Understand I did some yoga to chill me out and then went to bed. I knew I'd need a good night's sleep for what was to come. Class actually took my mind off of things until th Read more...
Rating: 60%, Read 6589 times, Posted Jul 13, 2022
True Story | Asian, Authoritarian, BDSM, Boy, Domination, Exhibitionism, First Time, Gay, Humiliation, Interracial, Male, Massage, Masturbation, Role-playing, School, Submission, Teen, Transvestite, Young
Instructor Mike's Academy - Part 1 - Taking the First Step by qtaimee
Warning: This is an explicit semi-fictional/semi-autobiographical multipart series involving White Daddy / south asian teen raceplay, crossdressing, and more. If you are not over 18 and/or find the notion of White Cock superiority to be offensive, then please do not read on. Aside from a few things altered, this recounting of several months of my life is almost entirely true. It feels good to get it off of my chest as a form of therapy regarding past sexual experiences. This experience almo Read more...
Rating: 80%, Read 5581 times, Posted Jul 13, 2022
True Story | Asian, Authoritarian, BDSM, Boy, Consensual Sex, Domination, Exhibitionism, First Time, Gay, Interracial, Male, Masturbation, Pissing, School, Submission, Torture, Transvestite, Water Sports, Young
Amazing Night With A Sexy Crossdresser by markerss
This happened a while back now, but the experience has stuck with me and I wish I could be with her again. At one point, I had become very interested in transsexuals and cross dressers and had even been with one that I met on Craigslist and another I met at a bar. Don’t get me wrong, I enjoyed being with girls too, but from time to time, I just had this urge or fascination to be with a tranny. Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought o Read more...
Rating: 69%, Read 8729 times, Posted Jun 27, 2022
True Story | Anal, Blowjob, Consensual Sex, Gay, Transgendered, Transsexual, Transvestite
Mistress Cruel Love - Chapter 4 - Mein Herrin! I Can Dance! by [JamesBondage]
Club Ishtar was jumping and so were Heather's bulbous curves. Her pudgy arms and thick thighs jiggled as she exited the bathroom and strode down the hallway back to the main room where the party was in full swing. The red satin of her dress stretched around her plump body as she strutted her stuff. Her confidence had been building steadily for months, but she'd never felt better about being a large and in charge female dominant since stepping into this Femdom wonderland. As the corridor opened Read more...
Rating: 65%, Read 2772 times, Posted Jun 10, 2022
Fiction | Anal, Authoritarian, BDSM, Black, Consensual Sex, Discipline, Domination, Exhibitionism, Female, Hardcore, Humiliation, Interracial, Masturbation, Oral Sex, Pegging, Plumper, Reluctance, Sado-Masochism, Slavery, Spanking, Submission, Threesome, Toys, Transvestite, Voyeurism
My Sissy Son - Part 1 by CumCrazedCanuck
As my euphoric haze began to fade and my vision came back to me fully, I continued to look down at my son's face. His glazed, messy, cum-splattered face. His eyes were closed lightly, as he began to lick his lips and "Mmmm" with delight. As he released my drained cock from his grip it rested on his cheek and he turned to kiss it again. I slumped back further on the desk and all I could think was "My God. How the fuck did we get here?" But to explain that, I have to go back to the beginning. Bac Read more...
Rating: 74%, Read 22624 times, Posted May 22, 2022
Fiction | Blowjob, Gay, Incest, Masturbation, Reluctance, Teen, Toys, Transvestite
Camming Down the Rabbit Hole Ch.12 by Dani_does_Dallas
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’t cum without something in my ass so she retrieved another one of my toys. This time however she said that she wanted to taste my load direct from the tap, so I laid back, she slid one of the larger Read more...
Rating: 76%, Read 2546 times, Posted May 05, 2022
Fiction | Bi-sexual, Blowjob, Cum Swallowing, Masturbation, Transgendered, Transsexual, Transvestite
Camming Down the Rabbit Hole Ch.11 by Dani_does_Dallas
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hoping to earn a little money, before being subtly coerced into dressing in lingerie, and taking small step after small step before I tumbled well and truly down the rabbit hole ending up wearing more fema Read more...
Rating: 75%, Read 4095 times, Posted Apr 24, 2022
Fiction | Anal, BDSM, Bi-sexual, Body modification, Coercion, Erotica, Exhibitionism, Male, Masturbation, Prostitution, Role-playing, Solo, Toys, Transgendered, Transsexual, Transvestite
Camming Down the Rabbit Hole Ch10 by Dani_does_Dallas
As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous night, which only heightened my state of arousal. One thing which did differ from the previous mornings was my sore throat. No doubt a result of my getting a little carried away although its scratching Read more...
Rating: 85%, Read 3285 times, Posted Apr 11, 2022
Fiction | Cum Swallowing, Exhibitionism, Masturbation, Pegging, Transgendered, Transsexual, Transvestite
Michael to Michelle by SonicRush66
This is the story of how I transformed from your normal straight married guy "Michael" to sissy slut "Michelle" I've always been curious about cocks since I was a teenager but I've never had the guts to try it. I've watched plenty of porn and wank chatted to hundreds of guys online but that's it, until now. I've had a few wank chats and roleplays with Gary before and it was fun, he'd go into detail how I'd be dressed up as a schoolgirl and he'd be my teacher and he'd use and abuse me and it wa Read more...
Rating: 91%, Read 5488 times, Posted Mar 24, 2022
Fantasy | Anal, Bi-sexual, Blowjob, Boy, Cum Swallowing, Gay, Group Sex, Transsexual, Transvestite
Camming Down the Rabbit Hole Ch9 by Dani_does_Dallas
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night before, by morning my cock was fully charged and my balls felt ready to burst. Reaching down I ran my hands over my chest, my stiff nipples jutting out causing a sharp intake of breath as their sens Read more...
Rating: 91%, Read 2142 times, Posted Mar 18, 2022
Fiction | BDSM, Body modification, Cum Swallowing, Exhibitionism, Masturbation, Toys, Transgendered, Transsexual, Transvestite