Sort by
Relevancy

Free Stories

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 5,692 cum domination Sex Toys sissy
81%
First time in Bangkok
If you have read my story about the first time I was with a TS girl then you know my experience was limited to just a few times. So about 4 years ago I went to Thailand to visit my buddy who was working there in a high profile job with the Thai government. We stayed in his apartment on the 40th floo... Read full Story
shemale lover 2015-01-13 13,626 shemales hardcore Group Sex
66%
Diamond
She was a vision from behind. Her long curly hair fell down her back in golden-brown and raven ringlets to brush the tops of her black leather chaps. Her bottom was bare, thrust out of the tight leather leggings, round and full and firm. The bare skin was a deep, latte brown. High-heeled platform bo... Read full Story
shemale lover 2012-05-11 4,404 facial oral sex cum swallowing
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 4,297 cum fuck oral
100%
Darla's Diary: Slutfest 1993
Vacation Day One At last!! Another fantastic two weeks of freedom...the freedom to do as I pleased and dress as I pleased because it was my VACATION TIME!!! This year was better than other years because it was the first time my wife and I had two weeks vacation each. Just like she does every othe... Read full Story
shemale lover 2012-07-14 3,881 oral facial cum swallowing anus
100%
THE WONDERFUL ADVENTURES OF MISS K: QUEEN OF THE ROAD
Miss K drove the car through the Midwestern countryside, enjoying the early spring breeze that leaked through the SUV's window as it blew through her platinum blonde hair. Her tits were held up by the tight, white, midriff-baring top she wore that stopped just below the lower curve of her tits... Read full Story
shemale lover 2012-01-28 4,057 licking sucking fucking Sex Toys
100%
Fun With Friends Chapter 5
When I got home, I spent the rest of the evening thinking about how in a few hours I had gone from a closet cross dresser to a full on cock sucking, bend over and take it up the ass slut who was then shown to a group of strangers as a latex and high heel-wearing sissy. I'm not sure when I fell as... Read full Story
shemale lover 2012-12-12 3,243 Stockings sucking Sex Toys crossdressing heels
80%
The Grass Ain't Always Greener...
Lawn care takes an unexpected voyeurism and exhibitionism masturbation detour I cut grass, mow lawns, manicure shrubs, trim bushes, and plant trees. Right handed and always trimming from the right side, I've never been a switch hitter when using my hedge trimmer, if you know what I mean. Always ... Read full Story
shemale lover 2013-01-16 5,021 Masturbation Blowjob blonde jerking big boobs
50%
Sex with Shonda
I'm a workaholic by nature. I love my job but that's not why I work so much. I work long hours simply because when I get home I don't quite have anything productive to do. I just sit down in front of the television or I chat over the internet. Life at home is dull so the best solution seems to be en... Read full Story
shemale lover 2011-09-18 4,061 Blowjob fingering handjob
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 7,143 sucking Big Cock cum domination
0%
The Greatest Lie Part 19
The booked me as Alex Rios and handed me an orange jump suit and slip-on boots. I changed in a tiny curtained alcove and relinquished my clothes, shoes and purse, and became Inmate 265743. The booking clerk ignored my pleading eyes, so I begged. "You can't put me into a male population. I... Read full Story
shemale lover 2012-01-21 4,812 hardcore femdom erotic encounters
100%
A Dare Gone Right
'Well, Paul, if you're not man enough, just say so!' 'Come on, that's not fair, Isabel. I've never dared you to do anything this risky,' I replied. 'Oh yeah? Walking around the mall in a pink latex micro-skirt and no panties wasn't risky? My balls were swinging around for all to see!' 'Yeah... Read full Story
shemale lover 2012-02-26 3,571 dildo Sex Toys
100%
Rachel and Chris
Part 1 : Rachel and the Ring Yesterday was clear with a light but chilling winter wind present to remind all that the bit of warmth in the sun would only last a couple of hours at best. I struggled between sweating and freezing as I worked to remove the winter street grime from my roadster. Top ... Read full Story
shemale lover 2012-04-10 4,586 Cumshot oral sex Sex Toys
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 9,006 Stockings sucking domination
100%
Jesse’s First Day
Jesse didn’t want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse ... Read full Story
shemale lover 2012-05-16 5,439 hardcore anal sex Cumshot
100%
Daddy always wanted a little girl
I SAW my daddy and his friends fucking a tranny one night and the next night he had a poker party. SO I got some of the sexy clothes he had. MINI skirt black lacy crotchless bodySUIT heels, wig makeup, EVEN IN my wheelchair, I LOOK LIKE LIKE a whore. Toward the end of the night I rolled out to drive... Read full Story
shemale lover 2012-05-21 3,151 first time anal sex Creampie facial
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 3,811 Group Sex fuck oral
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 3,849 anal Cumshot Masturbation Sex Toys
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 9,044 Amateur
100%
Birth of a New Sissy Part 3 Completion
I suppose at some level I knew it would happen. Or at least I should have. After nearly a month of servicing Jeff's cock and fucking myself silly on my dildo lover things took a turn. I came home from work a little early on a day Laura was off as well. When I got home she was out, but as soon ... Read full Story
shemale lover 2011-11-17 5,185 cum domination crossdressing
100%
A Special Girl
Please allow me to introduce myself. My name is Steven Brun. I'm a young Black guy living in the city of Boston. I recently graduated from high school and started college. I go to Boston College. It's a school full of rich white kids but I'm liking it so far. The city is big, much bigger than the sm... Read full Story
shemale lover 2012-06-30 5,451 Cumshot Blowjob oral sex
90%
The Conference
It had been a long day at the conference. During my evening meal in the hotel restaurant with some colleagues I noticed a stunning looking woman across the room. We met eyes on several occasions and acknowledged each other with a warm smile. She stood up to leave the restaurant and I was able ... Read full Story
shemale lover 2011-12-24 5,603 Fetish crossdressing erotic encounters
90%
Becoming a Sissy Slave
He gave me the choice. He had programmed me for a week and knew which way I would probably choose, but he gave me the choice. I could get out. Or I could continue. It was up to me. On my knees or out the door. It was that easy. Now I had to choose. I guess I should backtrack, first. You ... Read full Story
shemale lover 2012-03-05 16,871 hardcore deepthroating cum swallowing facefucking
100%
Discovering Mistress Sarah's World Part 7
Chapter 18 A Life Changing Decision Sunday morning was not much different than the day before for Josie. He woke-up on the floor outside Mistress Sarah's bedroom, dressed in a silk night-gown and his cock was hard and aroused when he awoke. Just like Saturday morning, he crawled into the bedroom.... Read full Story
shemale lover 2012-10-03 5,433 cum domination oral sex feminization
100%
Hooked for one week in Vegas
Vegas: Night one. Went to Vegas to visit a friend who was a high end escourt... long story short, I wanted to try it, just to say I did it. She itroduced me to a young sexy guy who was at a convetntion for business... Young good looking guy, brought me to the very nice hotel room, was being nice... Read full Story
shemale lover 2012-11-06 3,061 first time hardcore fingering kissing
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 4,553 anal shemales lesbian sex
83%
Headmistress' Favorite Sport Part 5
A new part of the first year slaves training was introduced as part of the plan to make them hopelessly addicted to sex. Every evening when they finished class they would be escorted to a room covered in rubber on the inside. The sissies were ordered inside unbound and unescorted, dressed only in th... Read full Story
shemale lover 2011-12-12 6,265 torture toys bondage and discipline chastity belt
100%
Tilted Kilt Chapter 5
"What can I get you tonight?" "Mojito" I walk down the bar and bend over to pull the bottle of rum of the shelf with my back angled toward the customer at the bar. I always wear my short, plaid skirt low on my hips. I'm sure the tattoo on my lower back is in obvious display... Read full Story
shemale lover 2012-01-25 3,615 Cumshot Big Cock
50%
Alex One: House Sitting for a Friend
Sorry, this is a little rough. I've tried expanding the original version but ... i dunno. Anyways this should be a continuing series of some sort. Alex One: House Sitting for a Friend. By Alex Shouse. My friend Karen had worked her way through a somewhat bitter separati... Read full Story
AlexShouse 2012-07-12 3,903 dildo oral transvestite sissy
90%
My True-Love Story
My name is Kim Young. I'm a happy and healthy nineteen this year. This is my very first story (but not my first "submission!") My story begins five years ago, when our neighbors moved in next door. I'll always remember that sunny April afternoon in Omaha, when they climbed out of their ... Read full Story
shemale lover 2012-09-10 5,784 Crossdresser Blowjob pissing Lingerie handjob
85%
Fucking with Gina!
Hi! Here I am with my own story! I’m a young white guy, a good looking son of a bitch! When I was a college student, one of those numerous young people who always rush for something, then I was a focus of interest for lots of chicks around! But then something changed. Changed a lot. As I remem... Read full Story
shemale lover 2014-05-13 6,716 tranny asshole Blowjob
90%
Night With Shana
This meeting took place in Los Angeles, CA. I’m sure many of you are into shemale porn movies and will know who Shana is. For those of you who don’t know her, she is a gorgeous white shemale with long brown/blondish hair, big tits ( think there is some silicone in there — but who... Read full Story
shemale lover 2018-01-14 11,182 tranny suck face fucking
100%
Being Twins
I knew something wasn't quite right but I couldn't be sure. My life for the past 10 years with my wife Jane was great. My name is Richard. Jane was 5'8", 120 pounds, lean trim body, 38D breasts, beautiful blonde hair and stunning features. I was 5'9", 148 pounds, and little chest or body h... Read full Story
shemale lover 2011-12-19 5,474 hardcore erotic encounters fantastic
83%
Story for adults Part 1
This story is strictly for adults. If you are minor or if you are offended by stories with a sexual content, don't read any further. Chapter 1 Pete thought he was a very lucky guy. In his early twenties he was quite rich, having inherited a fortune from his late parents. Because of his relative w... Read full Story
shemale lover 2011-12-20 6,100 bondage and discipline heavy feet reluctant
58%
Preggo Scat Sex
Sara was horny. For any type of sex. She was stuck on a bus heading to her school. After 14 years of wasting her time She discovered her own sexual abilities.She had her first practice by fucking her brother's friend. She didn't come to school to learn. She came to screw anyone in sight. She had ... Read full Story
shemale lover 2012-01-07 12,092 Masturbation lesbian peeing
50%
The Greatest Lie Part 18
They say that prostitution is the oldest profession. I disagree. Some guy must have been a professional hunter to have gotten together the spare change to pay for that first commercial fuck. It's like that chicken and egg conundrum. Eggs definitely came first. Just as mutation precedes evolution, th... Read full Story
shemale lover 2012-01-20 4,207 taboo hardcore femdom
100%
TS Prostitute Urge
After college I began to explore the world. To that point I was the average male that happened to get a lot of tail. My sexual exploits with women were something I was proud of and always gave me a sense of being a real man. After years of watching straight porn and imagining myself in every possibl... Read full Story
shemale lover 2012-01-27 3,585 Group Sex sucking cum
100%
The Bounty Hunter - Working With A Partner
My boss, Carl Bronson, was pleased with the results of my first case, and gave me more jobs over the next few months. In each, I learned from my mistakes and was able to apprehend my target. Even better, I was finally earning some good money and doing something that was worthwhile and, more importan... Read full Story
shemale lover 2012-01-29 4,455 sucking Creampie cum fucking
100%
Freddy Gets Two Cocks
First a bit of background to this story. This is an actual account of one of my experiences. I am a male cross-dressing Bi-sexual. Versatile but prefer to take the sub bottom role. Chris is a guy I have met a few times, he is top only, well hung, not a good repeater but quite a long stayer. He does ... Read full Story
shemale lover 2012-11-27 3,512 Group Sex sucking rimming
80%
Growing up wrong
Hello my name is Krystal, but everyone calls me Krissy. I'm 25 & live in the Detroit area. I work at a local hospital as a Physicians assist & I love it! I'm pretty much a doctor but limited at meds I can proscribe & I don't have to have malpractice insurance. Last night was my third ... Read full Story
shemale lover 2014-03-31 8,237 shemales taboo gay male
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 5,170 shemales Blowjob cum
75%
My First Time Out Part 1
Shayna paced back and forth throughout the entire Suite while she nervously smoked the long thin cigarette. She occasionally stopped and peered into the mirror thinking that all of her hard work had gone to waste for tonight. She was dressed to kill and had no place to go. The red patent platforms w... Read full Story
shemale lover 2011-10-17 4,403 first time cum oral
75%
Experimenting with Cock
I was 22 and at the time did not have a girlfriend. I had a habit of jerking off at least once a day if not more. Starting masturbation at an early age made me bored by "normal" porn star videos. Leading me to amateur porn. Soon that became boring and I was experimenting with everything. O... Read full Story
shemale lover 2011-12-01 4,806 gay male oral
66%
Candy Pink Part 2
Chapter 4 My parents had a letter shortly after from the headmaster Mr. James Allen. I was to head out to CA before the start of winter term to get settled into the dorms and go through orientation. The letter said I should be there no later than December 1st and that they would arrange for me to... Read full Story
shemale lover 2011-12-08 4,441 taboo Fetish crossdressing
92%
Seduced Willingly
Finally, I moved to a city that was exciting, Miami. I moved to Miami looking for something new and adventurous. I grew up in very conservative town where nothing exciting went on. In Miami I found different languages, gay people, different ethnic persons, art, and culture. However, my job keeps me ... Read full Story
shemale lover 2012-04-16 5,885 anal sex cum orgasm fingering
100%
Brazilian Discovery Chapter 1
Joan arrives in Brazil The plot from Susan and John series : Mr Gupta, the wealthy businessman had built his empire from scrap, starting from a small greengrocer shop in B'ham. He had slowly bought similar shops throughout England, federating them in a company that was powerful enough to build it... Read full Story
shemale lover 2012-08-24 5,342 Cumshot fingering Sex Toys feminization
100%
Aunt Susie's Training Part 6
It was now 5 weeks since my cock enlargement surgery and Aunt Susie had been a dear helping me recuperate. We didn't engage in any sexual activity for fear that I would get hard and slow down recuperation. We would still sleep together and spoon at night while we slept as my new 40DD tits were n... Read full Story
BITCHGURLvr 2024-06-25 3,324 cock sissy Cigarettes
100%
Playing at home
This happened at age 15 (I am 18 now). I have full red lips, tall, slender and my ass was round like a girl and I have a very small dick (now it is 4.5"). When I got my PC I discovered this shemale things. Seeing a girl body with a big cock was awesome and after a while I found myself mas... Read full Story
shemale lover 2011-10-27 4,564 first time Masturbation oral object insertion
71%
Happy Halloween
Hello my name is Mike! Let me tell you a little about myself for the story. I'm about 5 foot 5 and thin, about 135bls. I am half white and half hispanic, so i have a nice light brown complextion. I don't have much body hair and am very GAY! I have always know that I was gay, there was never... Read full Story
shemale lover 2012-01-11 4,233 gay male cum swallowing crossdressing
100%
Alex Two: The Next Time
Part Two of ??? (there is another series I'll start too, Hopefully its not too repetitive and my fetishes aren't showing too strongly. heh. That is sort of a prequel to this, I guess. I had forgotten about it till just now when I found it in a misnamed folder.) Alex Two: The Next Time.... Read full Story
AlexShouse 2012-07-12 3,232 tranny Crossdresser Masturbation
100%
Different 3some in Acapulco
My job in a large travel agency takes me every march to Acapulco for the Tianguis Turistico, (Mexico tourist fair) that takes place in this nice resort. I very much enjoy those trips, and especially the pole dancing bars, were I would hang out at least 2 or 3 times during my stay. Those places ar... Read full Story
shemale lover 2012-08-23 3,458 first time threesome Blowjob fingering
81%
My stepmother has a surprise for me
My name is Robert, I'm 18, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men on the videos, that turned me... Read full Story
shemale lover 2013-04-08 234,702 suck Big Cock jerking big boobs cum swallowing
94%
Different 3some in Acapulco
My job in a large travel agency takes me every march to Acapulco for the Tianguis Turistico, (Mexico tourist fair) that takes place in this nice resort. I very much enjoy those trips, and especially the pole dancing bars, were I would hang out at least 2 or 3 times during my stay. Those places ar... Read full Story
shemale lover 2013-07-22 6,316 anal sex Latina threesome oral sex handjob
100%
The Birthday Gift Part 2
This story continues the events started in "The Birthday Gift." If you want the full effect you should go back and read part one. If you like it, and this story as well, be sure to vote and leave feedback. The TV standing in front of the bed showed the scene we had watched I don't know ... Read full Story
shemale lover 2011-12-29 3,500 hardcore cum swallowing bondage and discipline
97%
My First Encounter
I had just moved to a brand new city to take a high paying finance job. I had been some what of a workaholic my first six months here. I was working around the clock 7 days a week to make a good first impression. My hard work had finally paid off and I had received a promotion that came with a quite... Read full Story
bman8816 2014-07-08 8,565 first time tranny suck cum kiss