Sort by
Relevancy

Free Stories

100%
Becoming A She-Males Bitch Part 2
After last nights ordeal I was given something to drink and taken to a bedroom upstairs. What I drank must have had some kind of drug in it because I was knocked out. I bet I was asleep in just a couple of minutes. I barely even remember lying down. When I woke up I was naked, sore as hell and fe... Read full Story
shemale lover 2012-01-04 8,765 cum oral domination
100%
The Trip Part 3
I soaked in the tub for close to an hour, thinking about my predicament, it was only the second day of the trip, I figured if I was going to get through the week then I just had to resign myself and do whatever Joe asked of me, sex is just sex, I reasoned, it doesn’t matter who or how many peo... Read full Story
shemale lover 2012-05-20 3,582 anal sex Cumshot oral sex
100%
The High Bidder Gets Chrissie
My BFF Kelly belongs to an Alternative Lifestyles Club and her being a member always seems to affect me. Several times a year the club hosts what they refer to as a "Slave Auction". The rules behind the auction state that certain members who are selected by random draw are required to br... Read full Story
shemale lover 2012-08-15 3,762 Group Sex fuck oral
100%
Sissy Crissi Chapter 1
Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need ... Read full Story
shemale lover 2013-01-30 7,872 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Unconditional Love Chapter 8
After a two' hour nap, Alison and I awoke and the first thing we did was make our way to the bathroom to freshen up. I started up the hot water and climbed into the shower and' once she finished relieving her bladder Allie climbed in with me under the hot water and we embraced each other. We kiss... Read full Story
shemale lover 2013-02-04 6,269 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
66%
Carioca holidays
My best friend was a shemale named Monica from Rio de Janeiro , she was a gorgeous and sexy brunette , many time at her home she use to tell me many story about her city and the fun you can have as a cd , also she says the guys are really hot and very well packed . One night we where chatting about ... Read full Story
Suellen blonde 2014-09-02 3,366 Group Sex suck Lingerie crossdressing cd
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,837 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
75%
Honeymoon Suite 2
Jason is on the phone with room service, while I am about to change out of my wedding gown. I had just got married, and I was now the blushing bride. Yes I got married. I was nervous now and my pussy was burning, because of the crazy bet we had made about not having sex a week before the wedding. We... Read full Story
Regina10 2021-02-22 3,598 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
80%
Amber
The summer after high school I moved into this cheap hotel downtown. I'd been working in the mailroom for a large company, and really needed to get my own place, but I didn't have much money. I also wanted to have more time to play dress up. It was an old building that had seen better days. I ha... Read full Story
ambersissy 2021-04-23 5,321 Crossdresser Amateur Big Cock Guy Fucks Shemale Interracial cum in mouth
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 4,981 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
100%
Amy and the Straight Jocks PT1
Only a couple close friends knew for sure and most others knew it as just a rumor. Amy dressed and lived life as a girl like she had since the start of high school when she moved from a new town. The jocks would laugh and whisper to each other when she walked by debating if the rumors were true. Co... Read full Story
DADDY4sluts 2022-08-09 3,828 Teen (18+) Cumshot Bareback Creampie Blowjob Guy Fucks Shemale cum in mouth
50%
Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... Read full Story
Elainetguk 2023-09-06 4,767 Stockings Big Tits Creampie Lingerie Guy Fucks Shemale Mature
100%
A Shemale Vacation Part 1
I was eighteen, naïve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for m... Read full Story
shemale lover 2011-09-05 10,846 Cumshot sucking cum swallowing
50%
Sissies Training Part 2
I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by ... Read full Story
shemale lover 2011-09-17 6,505 shemales Fetish bdsm
100%
Tina's Secret
My name is Jordan Conrad. Those of you who read my "Rebecca's Secret" series probably remember me. If you've never read them, I guess I should give you a quick summary, so you're not in the dark about what's been going on in the past few months of my life. Bear with me during the slo... Read full Story
shemale lover 2011-11-02 7,338 asshole shemale oral
0%
Lady Denisa's Gang Banged
The young black youth aged eighteen was lying on the bed while I mounted him for the third time that day. I used his cock and muscular body shamefully to bring myself off with no thought for his pleasure. Kenny was my toy boy, an aircraftsman from the base my husband commanded when he wasn't away on... Read full Story
shemale lover 2011-11-22 4,385 shemale oral orgasm
57%
Debbie Part 9
It soon turned out that Debbie wasn't destined to spend the rest of her life as a whore. As she returned to the apartment one night one of Mistress' men was waiting for her. She had only just opened the door, when without a word he cuffed her hands behind her back, gagged her and put a collar and le... Read full Story
shemale lover 2011-12-23 6,339 transgender toys bondage and discipline heavy
75%
Permanent Stay in Mastersville Part 5
When I woke up, I was so sore that I could hardly move. My body was a mass of pain and as I removed the blanket, I saw how bruised and ugly all the abuse had made me. The sight of my battered body made me sob with self-pity. I lay quietly waiting for Master to arrive. I didn't feel rested, but at le... Read full Story
shemale lover 2012-01-08 3,786 toys bondage and discipline heavy reluctant
100%
Angel Chapter 9
Angel Jones had been working as a teller at the big London bank for over a year, and her duties had become almost routine to her. It didn't seem like a rut, because she enjoyed her work, and it paid well enough to meet her needs. She enjoyed a good relationship with her fellow tellers, mostly attrac... Read full Story
shemale lover 2012-12-02 4,227 cum fuck oral
93%
My First Time
This is my first ever story written about my first ever sexual encounter with a transgender woman. I really hope you enjoy and want to leave me some feedback… I have slept with many women in my life. I have been married, had more girlfriends than I can remember, several fuck buddies and far too m... Read full Story
⭐TransGurl⭐ 2016-06-21 23,128 first time tranny shemale tgirl ts experience
87%
THE ATTIC NOVEMBER 7
THE ATTIC NOVEMBER 7 – PART 1 THE JOURNEY AND GETTING READY. Susan had not had the opportunity to make the journey to the Attic dolled up to the nines so she made do with just wearing her black and pink lingerie under the hideous drab stuff (yuck). Having arrived early and parked up, she relaxed ... Read full Story
sexysusang 2018-03-09 5,871 Amateur Group Sex Bareback Blowjob Guy Fucks Shemale cum in mouth
88%
Tommy Tries to Make It Up
Tommy Tries to Make It Up I have written about Tommy before. He was the eighteen year old neighbor that always stared at me checking me out, basically eye fucking me and that made me so hot and horny I eventually took his virginity and trained up on being a great lover. Well he had moved out... Read full Story
pennypenny 2019-04-30 6,136 Crossdresser Group Sex Bareback Creampie threesome Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,416 Big Tits Cumshot Masturbation Uniform Frottage
40%
Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
PornoDating 2019-08-15 3,912 Crossdresser Amateur Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock Asian gangbang domination Guy Fucks Shemale Interracial sex Mature Futanari Frottage Compilation Ass to Mouth Cartoon cum in mouth double anal dating life in Mars? life
100%
Vegas Encounter- part Deux
Tuesday morning, it’s early and dark. Jack is in an Air BnB home in Summerlin, a suburb of Las Vegas. He met an online friend Diane and her friend/roommate last evening and we all slept in the King-size bed. I look around, Diane is sleeping curled in a ball on her side, but Holli is not here. M... Read full Story
Jon Paul 2023-12-22 5,392 anal Stockings Cumshot Bareback Asian Guy Fucks Shemale
50%
MISTRESS'S TERROR
The night had ended EXTREMELY PLEASUREABLE with BILLY, RYAN & PETER in a literal BANG and I was HAPPY. Now that BITCH I were married with our diamond 2 carat engagement rings and diamond wedding bands we were LESBIAN LOVERS. We were perfect together, Aunt Susie had groomed me into a SHEMALE DOMINATR... Read full Story
BITCHGURLvr 2024-07-01 3,353 cock transsexuals smoking cigarette
75%
Bambii's New World
My mind was racing the whole time. I couldn't believe where I ended up. But the sensations were running through my body. A 9-inch cock was ramming my boy pussy as hard as it could. Another cock, at least 10 inches, was being forced down my throat as his hands wrapped around my head, forcing me to... Read full Story
shemale lover 2011-10-05 5,107 shemales Blowjob cum
50%
The Zodiac Coins: Libra
2400 YEARS AGO... He was a humble shepherd. It was night and the flocks were sleeping. As he gazed at the stars, he saw a shooting star. He knew it was a portent of some kind, but was not mystic enough to know what. A little while later he saw another shooting star and guessed that wha... Read full Story
shemale lover 2011-10-18 4,619 Group Sex Masturbation shemale oral
100%
The Terrace View Apartments Part 7
My new life had settled into a wonderful routine. I would wake very early in the morning, usually still wrapped securely in Mistress Kendra’s arms. I would spend an hour or so working on my figure maintenance exercises, enjoy a cleansing enema, a refreshing bath and body shave, then I would la... Read full Story
shemale lover 2011-11-19 3,907 Creampie Blowjob domination
87%
Headmistress' Favorite Sport Part 3
There was no more time for Denise and Susanna to get over their chemically induced bout of incestuous activity as Denise was being sent to school. This was of course part of the plan. Slaves should always feel guilty about something and once their slave training was over, neither would be able to ma... Read full Story
shemale lover 2011-12-12 6,215 toys bondage and discipline chastity belt
0%
Headmistress' Favorite Sport Part 7
At the academy Denise and the others immediately resumed their old routines. The training for the second year slaves had started a few weeks before the new batch of sissies arrived at the academy. Not many new elements were introduced in the training as the second year was mostly about perfecting th... Read full Story
shemale lover 2011-12-13 4,580 torture toys bondage and discipline chastity belt
66%
A Girl's Best Friend
The party was in full swing when Ryanna and her friends arrived. Of course, they were an hour late, since Glenys had gotten lost on the way. The house was out in the back woods; the owners didn't exactly go out of their way to make it easy to find. Their fellow townspeople probably would have frowne... Read full Story
shemale lover 2012-03-06 5,433 Crossdresser Shemale and Girl oral sex condom sex
100%
Eve Quest Part 4
Chapter 16 Monday morning I was told to wear my red panties, bra and ribbon; my white collar, bracelets and heels and a red sleeveless dress. Sheila and Jenny ate breakfast, got dressed and loaded me in the car. They dropped me off in front of the beauty parlor and Jenny said. "If Hilda f... Read full Story
shemale lover 2012-04-21 4,015 anal sex domination oral sex transvestite
100%
A Ski Bunny is Born Chapter 2
My first real man. Hugs and kisses to everyone who contacted Kim and I expressing how much you enjoyed our first episode. This is the second part of our life story so far, and is the first follow up to 'A New Ski Bunny is born'. It recalls the first time that Kim and I included guys in our ... Read full Story
shemale lover 2012-06-21 4,851 anal sex Cumshot oral sex rimjob
71%
A Ski Bunny is Born Chapter 4
Our next port of call was Copenhagen (Denmark!). We left London early one wet afternoon and flew across to Denmark's capital, which was also wet! The flight was relatively short and when we arrived we caught a taxi to our city center hotel. We had 5 full days here and were intending to enjoy each on... Read full Story
shemale lover 2012-06-22 7,055 butt fucking facial oral sex
100%
Rebecca
I work at a large restaurant chain in their construction division. I spend my time co-ordinating the construction and remodelling of the stores in our chain. Part of my job includes travelling to locations where restaurants are being built, and ensuring that nothing goes wrong. I was recently in ... Read full Story
shemale lover 2012-07-11 5,412 Blowjob shemale oral sex
87%
Feminized By My Mother Chapter 2
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... Read full Story
shemale lover 2012-07-24 13,093 sucking Fetish fucking sissy
100%
Finding A New Purpose Chapter 1
It had all started when I had lost some stupid bet over a video game. "Loser has to jerk the winner off," my friend Mike said jokingly while warming his trigger finger up on his controller. "Ha, funny." During the game I tried staying focused on beating him soundly so I ... Read full Story
shemale lover 2012-08-07 4,281 oral sex masturbating toys
66%
Angel's Interludes Part 2
Here are more of Angel's hot little interludes. Just unencumbered hot sex for your cold lonely nights. A Restaurant Interlude Angel and Bobby were sitting in a rather dark corner booth of a quiet little Italian restaurant. This was their second date and so far Angel liked him. He seemed willin... Read full Story
shemale lover 2012-12-08 3,116 Cumshot sucking shemale
58%
Janet Owns Me Now Chapter 5
It was a beautiful summer's day, perfect beach weather. i packed a light lunch and a bottle of chardonnay in the cooler and we headed for the closest beach, about a forty minute drive away. J. Looked beautiful in Her black two-piece bathing suit and floral silky wrap, Her hand light and warm on my l... Read full Story
shemale lover 2013-01-30 3,633 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 14,013 hardcore sucking ass fucking Guy Fucks Shemale
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,555 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
80%
A New Spin On Role Playing Games
A New Spin on Role Playing Games By: Shawna Summers shawnavinylltv@gmail.com I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to rol... Read full Story
shawnavinyltv 2018-06-14 10,660 Crossdresser anal sex Blowjob gangbang Lingerie bondage
100%
Holiday romance
I had a special holiday with a malay ladyboy this summer, I've known her since 2012 I guess but we never met before as soon after I began a relationship with a ts from Jakarta that lasted for 5 years. I never lost touch with the malay girl, but we never managed to meet until this summer, when I invi... Read full Story
KhaleedJawwal 2018-11-19 3,889 Creampie Blowjob Ladyboy Guy Fucks Shemale Mature
88%
LONDON CINEMA LIAISON
When I lived in London back in the 80s and 90s, I would often sneak off to a porn cinema with stockings, suspenders and knickers under my suit. My wife didn’t much like sex, so this was a release for me to get away from home and have some sexy fun. Once I had found a suitable seat I would ease down ... Read full Story
GinaG 2018-12-14 7,040 Stockings Blowjob blonde Lingerie Guy Fucks Shemale Mature Ass to Mouth
100%
Gay friend of my brothers
As I mentioned in previous stories, my brothers met Adrian at university, he was studying nursing, he was in the same year as my brother and they were studying one or another subject together, Adrian has brown skin, green eyes, his short Chinese hair He has a slim body, he was 1.69 tall, his nose is... Read full Story
lkusex 2021-03-08 5,260 Amateur Guy Fucks Shemale
94%
Foursome with two ladyboys
It's been quite some time since I posted a new shemale story here. Hope all of You who have experience with shemales will finally have some courage to write about it and share it with us. Let this sizzling story by Tommy be an inspiration to You. Who wouldn't want to be in his place in this crazy fo... Read full Story
shemale lover 2015-03-15 6,664 Group Sex Blowjob cumshots
91%
Lakeside Awakening
If anyone had told the way I’d meet my soul mate a few years ago, I never would have believed it. It was my senior year of high school and I had recently gotten out of yet another bad relationship with a girl. Lina had been a pretty, chubby blonde with a nice personality but a nasty temper. We... Read full Story
shemale lover 2011-06-27 7,401 ass Blowjob shemale
100%
Vengeance is sweet
What a warm day. Really hot, perhaps even the camels fainted in the zoo because of the heat. The thermometer reached 35°C that day. At these temperatures people usually aren’t up to do anything. So did I, because I sat together with Claude in his front yard. We were both sitting on our bea... Read full Story
shemale lover 2011-09-04 4,492 anal shemales lesbian sex
81%
Rebecca's Secret
-1- The hour was growing late as I looked around the cozy living room. Six of my friends were sitting in various places, in various positions, all watching some late night horror movie on the television. There was a feeling of general contentment. We had arrived at the house several hours earlier... Read full Story
shemale lover 2011-10-19 5,189 Cumshot shemale oral sex
66%
Cincinnati Apocalypse Part 4
The problem with Americans-one of the many, anyway-Giles thought, was that they had too much of everything, including too much money and too much time on their hands. What else could explain the vulgar extravagance of a place like Disneyland? The staff at the entrance turnstiles-guards, really, t... Read full Story
shemale lover 2011-11-23 2,989 hardcore celebrities shemale
87%
They Were Right
They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... Read full Story
shemale lover 2011-12-29 5,756 shemale Big Cock porn
100%
Marilyn's Family Reunion
The warm humid September air blew through the windows of the speeding silver Nissan Pathfinder as it cruised along the Belt Parkway. With the Marshall Mathers LP blaring out the stereo, Sharilynn whipped her SUV along as the wind whipped her ponytail and her plain white t-shirt. As little Mai lay sl... Read full Story
shemale lover 2012-01-02 4,393 sucking Shemale and Girl cum swallowing
100%
Barbie Jo Adventures Part 5
Friday Night I've gone all week as Joe; no one at work has said anything to me about Monday morning. So I assume I got away without being exposed as a cross dresser. I was working late all week and finally Friday is here. I am so horny and anxious to become Barbie Jo. Hopefully someone will call,... Read full Story
shemale lover 2012-02-18 4,276 sucking Fetish cum swallowing
100%
Betrayed Chapter 4
I really wasn't surprised when Dianna directed me into the parking lot at Ringers. It was only a few blocks across town from my new home; a five-minute drive, if the traffic wasn't killing at the time. Consciously, it had not been a factor in my decision to take the new place. Sub-consciously... wel... Read full Story
shemale lover 2012-05-29 5,024 Cumshot orgasm condom sex
83%
Caught at Lunch
Only so long can you hide, if you are wondering what the hell I am on about then let me explain. As a part time transvestite dressing is always a thrill as is the joy of turning myself from a very average looking guy into a sexy cock loving slut, but due to where I live the chances to fully dress... Read full Story
shemale lover 2012-06-11 3,771 anal sex Cumshot shemale fingering transvestite