Sort by
Relevancy

Free Stories

100%
Working for a Living Chapter 5
I pulled out of Chris' cabin just after six in the morning on a sunny July day headed for the beaches of Southern California. Chris had left two days earlier to visit an old neighbor from years ago but I knew what he was really doing. He had had a visit from Kelly, an 18-year old from Washington a c... Read full Story
shemale lover 2012-10-05 2,604 Cumshot sucking fingering cum swallowing
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 5,394 cum ass licking oral sex
100%
First Time S & M Whore
Suellen certainly looked the part of a cheap S & M whore: black seamed hose, shiny pink patent 5 inch heels, a black leather miniskirt, and a translucent white nylon blouse that clearly showed the black bra underneath. Her long blonde hair swayed seductively and naturally. Well the hair was natu... Read full Story
shemale lover 2012-10-24 5,167 Cumshot oral condom sex
85%
Something about Danny
What was it about my daughter's boyfriend that turned me on so much? No one characteristic comes to mind. I suppose it was a combination of things. And perhaps a certain time in my life also. I was 52, divorced, alone and quite bored. I had been divorced from my husband Jerry for 12 years and did... Read full Story
shemale lover 2012-11-12 5,110 fingering domination handjob spanking little dick
100%
G Is for Gemma
Stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** It all really started on a Monday. One bright sunny Monday, early summer, an unusually warm day for June in England. And it really was stupid thing to do... Read full Story
shemale lover 2012-12-15 4,708 anal Cumshot cock sucking club
75%
Find That Guy: Porn TV's TG Gameshow
Freddy was nervous as hell. His girlfriend Sue had signed them up for this stupid game show without even telling him. He still wasn't sure why he'd agreed. Sure they could win a lot of money, and they'd each get a grand just for participating. And sure they needed the money pretty bad. Desperately a... Read full Story
shemale lover 2013-03-04 4,609 sucking Big Cock jerking ass fucking big boobs
100%
yes, Mother give it to me
"Do your fucking job right, Henry! Jesus Christ, what are you, five years old? If I ever have to call you in here again, you're done! You hear me? You'll never work in this business again! Now get the hell out of my office." Mona could feel every set of eyes on the floor anxiously awaiting the pi... Read full Story
ASSEaster5678 2018-11-28 12,773 Guy Fucks Shemale
77%
Changes
A story about a mysterious change and how it changed the life of two people forever. The sunlight practically burned my eyes as I slowly woke up. I blinked several times and closed them again for a moment. I felt like crap, way worse than I should have. Last night the guys and I had gone to the bar... Read full Story
bigtranslover 2014-02-11 6,010 female transformation
97%
Shemale Runner
This is based on a real life experience and is about consenting adults engaging in sexual activities, if you are offended by such themes as shemales then do not read on any further. I try to stay fit, I run every day after work for an hour. There is an old dirt track walking path that links fa... Read full Story
shemale lover 2011-09-11 9,339 anal facial oral sex
87%
Innocence
I had just gotten off the train from my work, and now I was standing outside of the station, waiting for my bus in the freezing cold. I wasn't overreacting; it was really cold. I was wearing a thick winter coat and gloves, but I wished I would have remembered to bring a scarf or something, because I... Read full Story
shemale lover 2011-11-04 5,257 blonde transsexual lesbian
100%
A Close Encounter of the...
Another great tape and another great yank of the crank. Yea, she-males were pretty hot, Tom thought as he hit the eject bottom on the tape deck, but where on earth would he really find one? He had little doubt that if he did find a place where they hung out that there would be more than a few with a... Read full Story
shemale lover 2011-11-13 5,011 Cumshot Blowjob massage
100%
The Terrace View Apartments Part 2
The Terrace View Apartment complex was an impressive site, to say the least. It filled up two entire blocks on the far-west side of town. I actually passed right by it at first; thinking that it was a fancy hotel because of the ornate architecture arrogantly rising over the privacy fences that surro... Read full Story
shemale lover 2011-11-18 3,744 anal cum crossdressing
100%
April Fools!!
I'm Jimmy James and I've been hanging out with the same six guys since we started college. We're a pretty close knit bunch and have stayed in touch since then. At 25, I'm the only one of the seven of us still not married. Even though we all still get together for parties and get togethers, for t... Read full Story
shemale lover 2012-01-04 11,397 anal oral cd
75%
Old Folks Part 2
It had been eleven months since that day when I arrived at Honey and Frank's house. It was about 1am at night as I stood in a quiet street waiting for Frank to pick me up. I had just finished with my last client for the night a good blowjob with him ending up cumming on my face. I was touching up my... Read full Story
shemale lover 2012-01-10 6,878 transsexuals erotica romance crossdressers
42%
Chinese Extremes Part 3
It was time to leave Mistress Ming's house and Lien was dressed, or rather tied up, by the two little sissies. First a brutal corset was fitted around Lien's waist, followed by a broad, black leather collar. Lien's hands were then tied in an armbinder, a black leather sack that held Lien's arms behi... Read full Story
shemale lover 2012-01-17 8,581 torture extreme bondage and discipline
100%
A Brief History of Tina
1 - Monday It really has been one hell of a week and more to come maybe, though I really am not sure how this is all going to work out. An awful lot has happened since last Monday, I am just beginning to make sense of it. Or at least, some sense. On Monday I decided to 'shake myself out of it'... Read full Story
shemale lover 2012-02-08 4,686 licking sucking cum fuck swallowing
33%
A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
shemale lover 2012-02-23 8,241 Fetish transformation dildo
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 13,936 first time sucking fuck domination
100%
Daddies New Girlfriend
Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cyn... Read full Story
shemale lover 2012-03-09 12,198 sucking Fetish crossdressing
100%
The Invitation
"You see, we have to come up with something that would be so embarrassing for you that there is no way that you would ever show those pictures of me to anyone, regardless of how d***k you got, or how horny you got or how pissed off at me you were,” Sally went on. “Something that wou... Read full Story
shemale lover 2012-03-20 6,117 Group Sex crossdressing feminization
100%
A New Girl
Still half-asleep, I purred happily when I heard the curtains being drawn. I could hear the sound of rain beating against the outside of the window, but the poor weather was the last thing on my mind. Still barely able to believe my luck, I slid my hand down the side of my smooth thigh, delighting i... Read full Story
shemale lover 2012-04-05 4,495 fingering oral sex small breasts cum swallowing
100%
A Slut is Born
There I was, one week before the end of high school. Going to college in the fall. Nice car, good family, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried in m... Read full Story
shemale lover 2012-06-26 6,385 anal sex Fetish oral facial feminization
85%
Busted and Hoodwinked
INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack a... Read full Story
shemale lover 2012-09-30 5,958 anal Cumshot Ladyboy oral
100%
Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
shemale lover 2012-10-21 8,676 anal Cumshot shemale oral
100%
Angel Chapter 2
Angel Jones stepped off the train and hoped she was in the right place. It was noisy and confusing in the terminal, a far cry from the relatively quiet station in her home town where she had boarded the train that morning. One hand clutched a small suitcase that contained her makeup and clean linger... Read full Story
shemale lover 2012-11-30 4,259 oral sex tgirl feminization
100%
A "Girl" for Kelly
Kelly was sort of a loner throughout her life. She had very few friends throughout high school and college, and if she weren't around them, she would spend her time alone. Her love life was just the same. She did have a few boyfriends, and only ever managed to get one to have sex with her. It wasn't... Read full Story
shemale lover 2013-03-27 3,838 hardcore sucking Big Cock Shemale and Girl big boobs
88%
Becoming Lisa
From when I was as young as 9, smooth and long blonde hair, I was always dressing in my older sister's panties and bra, panty hose. My breasts were kinda girlish and i had long nipples that would get hard when I played with them. I was older now, but still only had a small 4 inch cock when it was ha... Read full Story
shemale lover 2013-08-09 13,053 Crossdresser Masturbation Fetish Lingerie kissing
96%
A New TS Slut is born
There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried i... Read full Story
shemale lover 2014-01-29 9,132 Cumshot suck ass fucking oral sex Guy Fucks Shemale
79%
My Shemale Stepmother Part 1
My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was re... Read full Story
shemale lover 2011-09-01 18,927 tranny Big Cock jerking off
100%
Shemale Fantasy - Suck Fest
This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... Read full Story
shemale lover 2011-09-13 5,301 Cumshot jerking off pantyhose
93%
The Babysitter's Secret Part 2
Two months had passed since Jenny and I had first made love on that fateful, snowy night. At least once a week, occasionally many more, Jenny and I had found time to be alone and indulge in our secret affair. I had never believed any sexual experience could be greater than our first time together bu... Read full Story
shemale lover 2011-10-24 6,690 Stockings shemale oral sex bisexual
91%
Stepdaughters Pleasure Daddy
As I was showering, I was thinking about Anna coming. What would I say to her? How would I act? I felt very uncomfortable and I was getting extremely nervous. I finished washing, then shaved. As I was getting dressed, Dawn came in. "I know your hungry, Daddy, but let's go out for breakfast.&... Read full Story
shemale lover 2011-12-05 7,676 anal licking Creampie
75%
Backsliding: Tim's Story
Every man has a weakness, but not everyman knows what that weakness is until it is too late. The story I'm about to tell is something I'm not entirely proud of. My name is Tim. I'm a 22-year-old college student at California State University. I'm almost at the end of my senior year studying to be... Read full Story
shemale lover 2012-02-09 4,946 sucking fingering Guy Fucks Shemale
95%
A Helping Hand
It was late on a Friday night when I heard my parents arguing. It always happened whenever they were getting ready to throw a big party. My mother played the role of party planner and handled all of the details, but between caterers, musicians, and the other help something always went haywire. My fa... Read full Story
shemale lover 2012-03-09 14,901 Fetish bdsm transformation
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 4,092 anal sex domination oral sex transvestite
83%
Head Cheerleader Mikki Part 2
Last night was one crazy night. I spent the night dressed femme and being used like a slut by my girlfriend. It was a wake up call for me. I guess wearing my mothers panties from time to time should of given me a clue about how much I liked being a femme boy. So here I am sitting in my room looki... Read full Story
shemale lover 2012-06-10 3,216 Cumshot lesbian sex oral sex
71%
A Schoolgirl's First Time
I’d been emailing and phoning Dan for several weeks when he first suggested that we meet up. It was very exciting and I couldn’t wait. My every waking hour was spent thinking about it. The only odd thing was the request he’d made. “Can I ask you a bit of a kinky favour?&rd... Read full Story
shemale lover 2012-06-10 4,363 Cumshot Fetish Uniform oral sex crossdressing
80%
Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
shemale lover 2012-06-24 5,426 big dick tranny anal sex Cumshot orgy facial oral sex
100%
Bob and Carol and Gemma and Alice?
I sat there, in the kitchen, suddenly very nervous again. The previous half-hour had started out nerve-racking enough but I had settled, more quickly than I had imagined. Carol hadn't laughed, she had been kind, and interested, and considerate, and she had listened and asked intelligent questions. B... Read full Story
shemale lover 2012-07-22 3,698 first time Cumshot oral sex cum swallowing
95%
T-Girl University
Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for ... Read full Story
shemale lover 2012-09-05 14,822 Cumshot Masturbation Blowjob ass licking redhead
84%
Alex to Alice Chapter 1
Everything had started off simple enough for Alex. He had met Elena at a bookstore while he was researching for a college paper. She was quite the vision at 29. She stood a respectable 5' 8" with a voluptuous body. While slightly plump, she maintained her hourglass figure and filled out quite n... Read full Story
shemale lover 2012-09-25 4,661 Cumshot domination oral sex
95%
Fitting Room
Several years ago when I was just starting collage I had just gotten my grant money and like a good responsible young man I decided to spend it on some new clothes to try to be more attractive to women. I went to a clothing store that had both men's and women's clothing. While browsing around the me... Read full Story
shemale lover 2012-11-03 4,780 anal cum oral deepthroating
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 118,784 hardcore Cumshot sucking bdsm domination
94%
Taken Chapter 1
Georgia pulled her Mercedes out of the gas station in Albuquerque back onto interstate 40 heading east. It was a long drive ahead to Chicago. She hated traveling alone, that was for sure, but the move to the office back east made it necessary. It was either drive there or sell her Mercedes and buy a... Read full Story
shemale lover 2013-01-18 7,261 Cumshot Big Cock ass licking big boobs ass fingering
83%
Cindy She Thong
Dialogue from Cindy’s point of View: Her name is Cindy and she is a shemale. Cindy is a beautiful woman is every way except one. She does not like the term tranny and prefers being referred to as a shemale. She is truly happy living as a woman. She began taking light doses of hormones at 19 she had... Read full Story
mrstanley 2015-07-29 5,164 Big Cock ass fucking deep throat piercing
78%
Once wasn't enough!- my 2nd shemale exp
So after my first experience I got really into the porn I bought movies magezines got on websites just couldn't get enough. But watching it wasn't enough I had the real thing once and wanted it again. It had been almost a year now and only one person knew about what I had done that one fat... Read full Story
Duke04 2017-04-01 10,442 anal sex Shemale Fucks Guy ass fucking Shemale on Guy
82%
Halloween Double Cross
It all started off so innocently... My wife Jo, tall, slim, blonde, aged 40 with 34DD tits and the sexiest big ass imaginable, works as a doctor. Her hours are long and arduous. She often comes home completely worn out. Only during the holidays does she tend to recover her sparkle. She is gorgeou... Read full Story
ASSEaster5678 2018-10-29 11,303 Shemale Fucks Guy sissy Halloween
50%
Realization vs. Reality
So…here I sit. 40 years old and revisiting the confusion of my youth. I am, and always have been, a first string heterosexual male. From my earliest memories of when I began to notice girls, I have always delighted in the wonders of women. I became sexually active at age 16, and there has nev... Read full Story
shemale lover 2011-10-18 3,609 sucking shemale cumming
100%
Working for a Living Chapter 4
The buzzing of her cellphone on vibrate was barely noticeable over the hum of the vibrator between her thighs. Normally Jamie would have just ignored it but Chris had told her he might call if his meeting finished early. Her hand felt for the phone on the nightstand beside the bed. She looked at the... Read full Story
shemale lover 2012-10-05 2,881 anal shemale oral cum swallowing
100%
An Unexpected Surprise
When I walked into the bar, I didn't notice her at first; I sat in a booth in a dark corner and ordered a drink from the waitress. The waitress returned with my drink, and when I went to pay her for it, she said it had already been taken care of by the blonde at the end of the bar. I looked, and ... Read full Story
shemale lover 2012-11-21 9,862 Fetish orgasm
81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 7,045 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
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 15,244 first time ass Cumshot suck cd sissy make up
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 18,017 big dick anal sex suck Blowjob cock sucking workplace
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 3,867 cock transsexuals smoking cigarette
50%
Blue collar Master, white collar slave
I sit on the couch in my owner's house, dressed every bit the slave I am. My body from the tips of my toes to my eyelashes is completely and permanently hairless, smooth, soft and beautifully tanned. My upper body is clad in a thin, soft and pink rubber T-shirt and my ass is clad in a pa... Read full Story
shemale lover 2012-01-12 9,611 torture extreme fiction bondage and discipline
100%
The Mocha Club... A Wife's Awakening
Fran had spent a restless evening in her hotel room, flicking through the channels on the television, finishing the large glass of red that room service had brought her and writing up the actions from the client meeting earlier that day. Now she was bored. It didn't help that the hotel her manager h... Read full Story
ASSEaster5678 2018-07-09 9,038 Amateur