Sort by
Relevancy

Free Stories

93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 15,434 first time ass Cumshot suck cd sissy make up
82%
My wife made me a bi-sexual
One night me and the wife were out drinking at a lounge on Maine Street it was getting late so we headed back to the car. As we were walking down the street, we walked by this adult bookstore called A-1 Adult Books joking around I said we should go in and look around (They had sex toys, books, and m... Read full Story
JamieLeeCD 2016-04-27 31,070 anal Blowjob cum glory hole bi-sexual
85%
An Unintentional Fisting
During the last weekend I ended up being busy, which I hadn't planned since that was suppose to be a weekend of anal bliss for me. I had finally ordered two new dildos and I was rearing to take them for a spin. Monday came and the day dragged on while all I could think about were the two black ... Read full Story
Purple Dagger 2018-03-02 7,048 Crossdresser Amateur Masturbation Ladyboy Sex Toys
100%
Blind Date
XtinaSmith2017 Anthony awoke to a piercing buzzing tune, a nice enough melody, but one he had come to despise shortly after he had made the mistake of making it his alarm. The culprit, his smart phone, was plugged in on the nightstand beside him and was in the process of making him gleefully aw... Read full Story
Gwapo67 2022-07-01 5,785 Bareback Creampie Shemale Fucks Guy Blowjob
80%
Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
Samantha sissy world 2022-09-20 4,905 Teen (18+) Crossdresser Big Tits transformation transgender feminization pov sissification Cartoon magic Gender Bender
97%
Leona
I think of myself as resolutely straight. I look at a lot of porn although I have plenty of girls to fuck. Steven, an old college buddy, dropped by and proposed that we go to a shemale bar that night. I was shocked and refused. But Steven retorted that if I was sure about my sexuality, I should have... Read full Story
shemale lover 2011-06-25 45,136 anal Blowjob cum
83%
Revenge is a Dish Best Served Hot
Commissioned by: Hobgoblin Written by: christhestampede ~~~ Yuffie climbed off the Highwind's ladder and stormed across the field to a nearby clump of trees, fuming and kicking at the ground as she went. Before entering the grove she turned and shook her fist at the departing airship, cursi... Read full Story
BoyVixen 2016-03-30 6,288 cum lesbian dickgirl
85%
Unforgettable First Time
I am in my late thirties and have known for a while that I have a sexy body. I'm 5'11", slim and athletic with little cherry butt and shapely legs. A lot of women have told me my body is sexy. A few men have mentioned it too. Sometimes I get photo-snapped at the pool or the beach. I've been luc... Read full Story
shemale lover 2016-05-06 10,280 cum oral deepthroating
80%
How I Became Vanessa Part 1
I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husband moved to... Read full Story
shemale lover 2011-09-09 4,459 anal sex shemale dildo
100%
She Took Control
I was at the bar on a Saturday night drinking as usual. I was scoping out the girls and hoping I could find something to spend the night with. I found absolutely nothing. I continued to drink and drink and drink until I blacked out for the most part and can’t really tell u anything after that.... Read full Story
shemale lover 2011-09-21 5,538 asshole Blowjob dildo
50%
Healthy Behavior
"Uhh…is Mr. Stanford around?" "One moment dear…ooh, damn heels. Makes it impossible to walk through doorways. Here I am ma'am. So, did the maid get you here alright? Hello? Earth to…" "I can't believe this…" "Oh, the heels? Yeah... Read full Story
shemale lover 2011-10-19 4,070 Big Tits transsexual oral
84%
Page Sixty-Nine
When my wife suggested that we rent out the guest rooms above the garage to a college student it sounded like a good idea. It was very much like a small apartment, with a bedroom, bathroom, and small living room. No kitchen of course, but we could share ours and it seemed like a good way to make... Read full Story
shemale lover 2011-10-20 6,143 cum oral deep throat fucking
100%
She's Not Hazel
My family had hired Maria awhile back a live-in housekeeper. She was from some small town in Brazil and was brought here through some charity from the church. She is only in her late 20's and is extremely attractive. she looks just like one of those girls you see party on E! Wild On, Her skin has a ... Read full Story
shemale lover 2011-11-29 3,403 oral cum swallowing
100%
Barbie Jo Adventures Part 1
Halloween night It was agreed by all three of us that we would dress up as women and Wanda as a guy. So when I arrived by taxi and went into the house I was wild that I was the only one dressed up. I stood there, my face as bright red as the lipstick I had on while Peter, John and Wanda whistled ... Read full Story
shemale lover 2012-02-17 4,614 Fetish cum swallowing stroking crossdressing
50%
Carol, The Saga Continues
It's very late Monday night as Carol returns from the date that J C had forced her to keep, she places her purse on the hall table, throws her jacket over a chair and walks toward her bedroom. She can't wait to shed this clothing that J C demanded she wear. As she walks, her feet, clad in the five i... Read full Story
shemale lover 2012-03-09 2,861 anal sex shemale deepthroating
100%
A Job in the Theatre Chapter 19
"Be a dear and get that bag from the car," Paula winked. "Sure," Billy said stuffing his erection back inside his leather pants. He stood, and for just a moment, was right next to Gary, almost touching. Gary could feel the heat waffling off of Billy. He looked so obscene with ... Read full Story
shemale lover 2012-03-15 3,150 anal sex shemale stroking shaving
87%
The Ebony TS of my dreams
This story is about one of the most memorable piece of cocks I've ever experienced in my 30 plus years of getting fucking. I just thought I'd write it down and share it simply because I'll never forget it and because I'm a married man and it most likely will never happen again. It happened about ... Read full Story
shemale lover 2012-04-02 4,569 Blowjob Ebony missionary position
66%
A Night Out To Remember Part 2
Decisions... decisions... we all make decisions everyday and most of them are simple easy decisions. Some may take hours, some take seconds and some are made before we even know it. Some decisions carefully planned and some have planning at all. Some decisions are between several choices and some ar... Read full Story
shemale lover 2012-04-20 2,993 anal sex Cumshot Sex Toys
90%
My life as a girl
He stood up and unbuckled his pants and let them drop to the ground. Pushing me down to my knees in front of him, his cock hitting me in the face. God it was at least eight or nine inches and his balls hung heavily down. There you go you little tease. He jokingly said. Its all yours to enjoy my b... Read full Story
shemale lover 2012-05-14 6,819 facial oral sex throatfucking
60%
A Sissy Boy is Made
By any measuring stick Greg Martin was a wimp, and a very submissive wimp at that. His wife of 14 years, Jaclyn, had discovered this even before the two of them were married. Actually, Jaclyn wouldn't have taken a second look at Greg, as most women didn't, had it not been for his submissive nature. ... Read full Story
shemale lover 2012-06-15 8,585 Cumshot oral sex sissy
100%
Birthday Present
Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all about the exchange and nothing else was said about my birthday. The day arrive... Read full Story
shemale lover 2012-06-16 14,285 Cumshot Fetish orgasm oral sex
100%
Fender Bender Chapter 7
The main Characters are as followed: My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I turned 18 a few months ago. Gary is almost 6', 185 pounds. He has short blonde hair and dark blue eyes. He has a nice tasty 7 1/2 inch cock... Read full Story
shemale lover 2012-07-27 3,236 Creampie ass fucking domination oral sex sissy
100%
Fender Bender Chapter 8
My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I turned 18 a few months ago. The last two weeks of summer vacation was a wild time for me, I knew that things would settle down once school started. Gary, my best friend for years,... Read full Story
shemale lover 2012-07-27 3,141 Fetish cum oral cum swallowing sissy
55%
Dawn's Diary Chapter 3
Back at home it took nearly a week before I was able to sit comfortably after my encounter with Sam and her huge dildo. My thoughts constantly drifted back to her. I continued to keep my body cleanly shaven and regularly wore the outfit that I had worn that evening with Sam around the house. I bough... Read full Story
shemale lover 2012-07-31 3,140 Crossdresser Cumshot oral sex
100%
Dawn's Orgy
Dawn always tried to invite new exciting guests to her annual orgy. One year she invited beautiful transvestites. Another time she invited female body builders. Over the years, she provided male and female strippers, drag queens and porn stars. This year topped them all. Nobody spiced up the gatheri... Read full Story
shemale lover 2012-08-03 3,875 anal sex Cumshot transsexual
100%
Transsexual Sisters Chapter 3
Part 3: Their First Men Dawn and Cassie searched for Michelle and Nicole. They did not appear to be anywhere in the club. Pixie saw them looking and told them: "Your ladies left a long time ago with their new friends Marty and Brandy." Pixie said. They left me a note for you. "H... Read full Story
shemale lover 2012-09-07 3,009 Blowjob Big Cock fuck oral sex tits licking
100%
Brian and Bree, and Mitch Chapter 2
"What ever I want?" Mitch looked deep into Bree's eyes, she sheepishly nods up at him, "I've always wanted to please a man, I'm just glad it could also be my best friend." She replied, her voice trembling with nervous excitement, "Just give me ten minutes, and meet me in ... Read full Story
shemale lover 2012-09-20 3,490 anal cum fingering oral sex
40%
First Sexual Crossdress Experience
How my secretary found out I'm a bi TV and how me and my TV friend educate her into some of the more zany aspects of TV sex. *** As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front o... Read full Story
shemale lover 2012-09-27 5,730 first time Fetish cum oral crossdressing nylon
100%
Amazon Archipelago
On the northern end of Stuart Island, in the far corner of the San Juan Islands in Washington State, an old lighthouse guards the broad, deep channel between the United States and Canada. No longer manned, the building and light tower stand empty now, replaced by a soulless but efficient solar-power... Read full Story
shemale lover 2012-10-24 5,513 cum ass licking oral sex
100%
How I Became Vanessa Chapter 1
PART I: I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husba... Read full Story
shemale lover 2012-10-31 3,937 anal Cumshot Masturbation Sex Toys
100%
Dress and Drive
I am twenty four years old and have been cross dressing for years now. I started when I was young and when my sister was not at home. Since then I have moved into a house of my own and I have built up a pretty large collection of clothes, shoes, make-up, and a few different pairs of fake breast. I d... Read full Story
shemale lover 2012-11-16 3,711 anal sex Cumshot fingering oral sex
100%
Angel Chapter 7
Angel Jones's Christmas sex affair with Dennis McGowan had been extremely enjoyable, but strictly a one-time thing. Although tempted to stay in London, in hopes of enjoying more of the lovely T-girl's charms, he had previously taken on commitments that had to be met, and he left London in order to m... Read full Story
shemale lover 2012-12-01 4,028 anal sex Cumshot tgirl
90%
Tranny Fuck
Its about midnight, and I'm horny a fuck. Couldn't find one of my late night freaks to come over and milk the cow, so i headed over to the east side to see what was going on at the strip club. As I get off on the exit, there's this long road that leads to the strip clubs. Its dark, on this side of t... Read full Story
shemale lover 2013-07-18 6,002 anal sex Blowjob ass licking 69 balls licking
87%
Fem Firm 3: The Return Of Frankie
PART 1 THE VISITOR Over the next couple of months, it was pretty much business as usual at the Firm. You know, depositions, court filings, motions, hot sloppy blow jobs and ass destroying anal sex (Thanks Angela!).Not to mention Friday Fuckfests. But since I started working here everyone se... Read full Story
bennyx709 2016-11-14 12,438 anal sex ass fucking oral sex cock sucking thick cock
92%
The Girl Next Door Ch. 02 by derezzed ©
Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the sunlight that h... Read full Story
StevelovesTgirls 2019-06-11 12,688 Amateur Big Tits Blowjob Big Cock Guy Fucks Shemale
100%
Chance Encounter 2/7
She turned over onto her stomach and lifted her ass up for me……. I’ve seen some gorgeous asses before but Vanessa’s ass! It was heaven, it was perfectly shaped, it was clean, it was smooth, it was divine and it looked tighter than I expected. I slapped her left cheek and I got an incredibly sex... Read full Story
Katlick 2019-10-10 6,276 Small Tits Bareback Blowjob Big Cock
100%
How I Became Vanessa Part 3
Hello dear readers, I strongly encourage you to read the previous two chapters of this story to fully grasp the sudden changes which affected my life. * At home, Elena was waiting for me but she wasn't alone, her boyfriend was there too. He was a tall black guy named Jeff. I told them all t... Read full Story
shemale lover 2011-09-09 3,861 cum transsexual oral sex
62%
Man Is Humiliated By Escort
I am a very adventurous, open minded married guy. I am 6'2", 150lbs and I have a 5" cock. My wife (Mary) is great but she is very straight laced and doesn't like to have sex but twice a year so I decided to look elsewhere to fulfill a few fantasies. I am sure my size and stamina have a lot... Read full Story
shemale lover 2011-09-30 7,279 sucking Big Cock cum domination
85%
Continuing to Love the Feeling
After an exhausting but exciting day, i slept very well and arrived the next morning ten minutes early. I went through the back basement door and began changing. Ten minutes later i heard Mrs. Hawthorne calling me, Bitch Sheri come up here now! My maids outfit wasn't complete but i went up to ... Read full Story
shemale lover 2011-11-03 3,577 asshole sucking cum fingering
80%
Vicky Part 1
"Dear Sir, We recognize you as a person of discerning taste. We would therefore would like to invite you to a display we believe you would find most enjoyable." What followed was an address and a date, one week away. My name and address were correct, but I didn't have a clue what they w... Read full Story
shemale lover 2011-11-14 4,808 sucking cum fingering
66%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2011-11-14 6,920 Big Cock Ebony transsexual
100%
Tranny Fuck
Its about midnight, and I’m horny a fuck. Couldn’t find one of my late night freaks to come over and milk the cow, so i headed over to the east side to see what was going on at the strip club. As I get off on the exit, there’s this long road that leads to the strip clubs. Its dark,... Read full Story
shemale lover 2012-03-25 4,574 Big Cock cum ass licking 69 position
100%
Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
shemale lover 2012-05-07 5,038 shemale Big Cock oral sex cum licking
90%
A Sissy Surprise
I got home early from my night out with the girls. Jeff wasn't in the living room watching tv so I figured he was in the bedroom jerking off so he wouldn't have to bother me with a request for sex when I was toasted. I decided to surprise him and slowly made my way up the stairs. I walked into th... Read full Story
shemale lover 2012-06-15 6,079 Fetish oral sex crossdressing
100%
Head Cheerleader Mikki Part 4 Mikki wants a Boyfriend
This is part 4 of Mikki's story. Please read the previous chapters. After Monday night at Tommy's house I came to the conclusion that I want to be with Donna when I'm Mick and guy when I'm Mikki . It's Friday night and Donna is coming over . My dad is coming home on Sunday so my mother wants to s... Read full Story
shemale lover 2012-06-16 2,665 first time Cumshot oral sex double penetration
68%
How I became a sissy
So it all started from answering a random craigslist posting that didn't even have a picture. I was off work and horny so I was cruising the ads and I came across a Cross dressing married dom and his wife looking for a sub. I was no stranger to the lifestyle and it intrigued me so I began to write a... Read full Story
shemale lover 2012-07-30 7,265 Creampie oral domination Sex Toys
100%
Abducted and Turned Out Chapter 2
2: Fun time So, after I blew the guy downstairs and told him to come and knock on my door and pay me to blow him again anytime, I went up and took a long hot shower and put on a nighty and went to sleep. I slept surprisingly well considering I had just spent a long night out selling my ass. I tho... Read full Story
shemale lover 2012-08-10 4,686 Crossdresser anal sex sucking Creampie facefucking
100%
Brazilian Heat
At twenty-six I did something I had been trying to do since I was eighteen. I finally took the vacation I wanted. Ever since my freshman year of college I had been trying to get to Brazil for spring break. Spring Breaks came and went and never once did I make it to Brazil. All I knew was that I was ... Read full Story
shemale lover 2012-08-26 6,990 anal sex Big Tits Blowjob ass licking
90%
Professor to Sissy Slut
I had just turned thirty-four and I was miserable. My wife of twelve years had left me for another man and was living with him. We were not yet in the process of filing for divorce and I was hoping she would have a change of heart. I was still in love with her but I understood why she had left. We h... Read full Story
shemale lover 2012-09-04 5,029 Stockings Cumshot Blowjob fingering ass licking
100%
Discovering Mistress Sarah's World
Chapter 1: Meeting Mistress Sarah Joe's heart pounded fiercely as he stood at the door to his Mistress's house. He did not expect to be so nervous at his first meeting with her. After all he had known her for over a year. Mistress Sarah had been gracious enough to allow him into her world. He was... Read full Story
shemale lover 2012-10-01 5,989 Fetish domination cum swallowing feminization
66%
Discovering Mistress Sarah's World Part 2
Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "ki... Read full Story
shemale lover 2012-10-03 5,813 cum domination Sex Toys sissy
100%
How I Became Vanessa Chapter 3
Hello dear readers, I strongly encourage you to read the previous two chapters of this story to fully grasp the sudden changes which affected my life. * At home, Elena was waiting for me but she wasn't alone, her boyfriend was there too. He was a tall black guy named Jeff. I told them all t... Read full Story
shemale lover 2012-11-01 3,613 anal sex Cumshot sucking dp
100%
Francis Meets a Black Stud Part 5
I finally came upon a plan that I thought would make everyone happy. I would keep on playing this game with my man. I figured that as long as I was dressed like a girl, it didn't matter who he showed those videos too. I mean no one would know it was me and after all, he would be finish his vacation ... Read full Story
shemale lover 2012-11-20 3,005 cum oral sex Interracial
66%
Frank & I Call On Jill & Mary
Frank is one of the horny young men who sometimes go with me when one of my lady friends wants another man or two to join us. Recently, he went with me when I called on Jill and Mary. Usually, when I call on them, I eat Mary's pussy and fuck Jill's ass while Mary sucks her off, but this time Mary wa... Read full Story
shemale lover 2012-11-22 3,866 tranny anal sex Cumshot foursome
100%
The Meeting
He could not believe that he was finally going to see her after all these years. Since his divorce, she had been all he could think of. He fantasized every day how it would be to see her again, make love to her again, and now the day had finally arrived. He could barely sit still. He had decided... Read full Story
shemale lover 2012-12-21 5,866 Crossdresser hardcore Cumshot Lingerie Latex
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,751 sucking Shemale Fucks Guy Blowjob Big Cock Interracial