Sort by
Relevancy

Free Stories

100%
Denial: Third Comes Conversion
It had been a few weeks since Mark had became Miranda full time. He no longer had any of his own clothing and had taken a place as servant in the home. Janine had been slowly beginning to work Mark over by using 'creative discipline' and during the last day few weeks had began altering his behavior ... Read full Story
shemale lover 2012-08-16 3,687 jerking oral sex sissy
80%
Aunt Susie's Training Part 5
Aunt Susie and I woke up around 1030AM and Aunt Susie said we need to get ready for a surprise appointment in the city. We put on our make up, I pulled a ponytail again and we got dressed in jeans and heels and matching white button down shirts which we left untucked. We drove first to Aunt Susi... Read full Story
BITCHGURLvr 2024-05-16 3,673 cock sissy Cigarettes
100%
Headmistress' Favorite Sport Part 10
When Denise came to she was lying in bed. She had been washed and she could no longer feel the annoying diaper rash. In fact she felt fine, clean and well rested. On her feet were what turned out to be black Oxfords with seven-inch heels. Her ankles were in steel cuffs and connected by a eight-inch ... Read full Story
shemale lover 2011-12-13 4,733 torture toys bondage and discipline chastity belt
75%
Debbie Part 1
He had gotten a job with a large company doing odd jobs, mostly filing papers and bringing out mail. It wasn't much, but it was enough to pay for a small one-room apartment on the seedier side of town. Since he was still very shy from his experiences in high school he hadn't made any friends yet, bu... Read full Story
shemale lover 2011-12-22 9,454 transgender toys bondage and discipline heavy
84%
She never saw it coming
When I was 19/20 I used to frequent LGBT bars roughly twice every month. Most nights not much would happen but I found myself going to the trans nights more often. Until I eventually had some experience with trans girls. It was mostly fairly soft fun. Me getting oral and occasionally topping th... Read full Story
chris1989r 2022-02-01 5,257 shemale gangbang facial
83%
Teacher Student Confidentiality
It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... Read full Story
shemale lover 2012-02-11 14,135 anal Blowjob black fiction
100%
An Invitation
"Oh come on,Sarah. There has to be a way." An innocuous enough statement, but that's how it all started. I'd just received an invite to Cressida's annual Christmas party which, maybe not on the Hollywood A list, was within the cognoscenti an occasion not to be missed. The soirees of ... Read full Story
shemale lover 2012-11-16 4,690 Fetish oral sissy
90%
DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
CD DIXIE IN NH 2016-05-10 10,324 Big Cock cumming sperm ebony cock
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 6,493 transgender toys bondage and discipline heavy
66%
Debbie Part 10
Debbie might have lived out the rest of her life if it hadn't been for some events, which started back at Mistress' mansion. Several years after selling Debbie, Mistress Helen Chamberlain still ran her ruthless slaving operation. Giselle was still her favorite slave, constantly restrained and regula... Read full Story
shemale lover 2011-12-23 5,080 transgender toys bondage and discipline heavy
100%
Fifties Housewife After the Party
I had not fallen asleep after Darren had, exhausted, after the party and the incredible lovemaking we had shared. I just couldn't come down from the high and emotions of the whole direction we had taken. I was lying spooned against him, his warm cock nestled warmly against my ass. My nightgown seeme... Read full Story
shemale lover 2012-08-03 3,608 anal sex Cumshot spanking
88%
Caught Crossdressing by a Real Man
This story is a continuation of night club cum slut. Ever since I first wore panties for a boyfriend, I had built up a collection of lingerie. I gradually worked up from panties to the most erotic lingerie I could find. My fascination with cross dressing went a little further with a new fetish f... Read full Story
shemale lover 2013-01-17 35,618 Crossdresser sucking Lingerie ass fucking ass fingering
100%
Headmistress' Favorite Sport Part 6
At Mistress Rachel and Master Tony's house Denise was pushed into the role of maid along side her mother, Susanna. Susanna had been reshaped exactly as Mistress Rachel wanted it. She was now a devoted little nymphomaniac slave who loved her mistress and master and who would do anything for them. Lik... Read full Story
shemale lover 2011-12-13 4,715 torture toys bondage and discipline chastity belt
80%
Headmistress' Favorite Sport Part 11
Denise lay in the trunk of the car, her legs tied together with rubber straps waiting patiently to see what would become of her. She had long since relinquished all control over her own life and knowing that she was just useless sissy-slut made it easy to accept that whatever was done to her was pro... Read full Story
shemale lover 2011-12-13 6,246 domination torture toys chastity belt
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 3,893 toys bondage and discipline heavy reluctant
75%
Flowers in the Heart
Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... Read full Story
shemale lover 2012-11-11 10,548 anal tranny Cumshot oral
90%
Collette's Property
I've been Collette's lover for four years now and this gorgeous, incredibly kinky woman still continues to amaze me. Our sex life would be unimaginable to most people, even those who live lives embracing BDSM and other fetishes, and it's Collette who makes it happen. Of course everything is a trade ... Read full Story
shemale lover 2012-12-19 8,104 anal Crossdresser Blowjob domination ass fingering
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 8,866 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
100%
Fulfilling A Girl's Male Fantasy Part 2
Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a ... Read full Story
shemale lover 2012-04-04 4,468 Stockings anal sex Group Sex Blowjob
75%
Rebound
My story is nothing new, like most girls who used to be boys I knew from an early age that I was different to all my school friends. My dad was a thug of a man, who enjoyed the physical battle of the rugby pitch as much as the post match booze up, but I took after the mother who died giving birth to... Read full Story
shemale lover 2011-11-25 6,313 anal Creampie oral
87%
Finishing School for Shemales
Mistress K looked at the school report and smiled. She wouldn't describe herself as an evil bitch, but plenty had. She was proud of her position. Headmistress of the Finishing School for TGirls. So many beautiful shemale girls had left her careful administration and gone on to happy lives, or ... Read full Story
shemale lover 2012-08-09 10,597 shemales Cumshot domination oral sex
90%
Young Crossdress, Meets His Daddy
Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very ... Read full Story
shemale lover 2012-08-17 4,616 anal Crossdresser Cumshot Fetish oral domination
100%
The formidable weapon of women
five ears of marriage, my desire for my wife having greatly diminished, she decided to take control of my sexuality. A female association transformed her in a few months into a perfect dominatrix both physically and cerebrally. Every night before bed, she approaches me, dressed in a latex comb... Read full Story
sandratvtg 2024-06-19 2,408 anal Lingerie femdom submissive femboy huge toys
100%
Mike der Pfleger
Mike der Pfleger Vorwort: Es handelt sich hierbei um meine allererste 'Sexgeschichte' die ich schreibe. Meine Schreibkunst befindet sich gelinde gesagt auf Amateurniveau. Die Geschichte ist frei erfunden und entspringt rein aus meinem perversen Gedankengut. Ganz nach dem Motto: 'Geschmäcker si... Read full Story
baileyjay69 2024-08-26 237 anal Crossdresser Amateur Blowjob Big Cock Mature sissy femboy
100%
The best of two Worlds Part 3
Ever since I got married my sex life has become great. My French wife Jacqui is absolutely stunning. She is in her late thirties, blond with a slim body to die for. Her only complaint is her breasts size. I can’t find anything wrong with them, but then again women know better. She is highly se... Read full Story
shemale lover 2012-04-26 2,795 Outdoor oral huge tits
100%
Flowers in the Heart Part 2
Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... Read full Story
shemale lover 2012-11-11 6,356 sucking oral sex facefucking
80%
The Terrace View Apartments Part 6
The days start early for the Terrace View Apartments sex slave staff. Especially the newest sissies that have yet to completely adapt to their lives of sexual servitude. My first full day as a sissy slut began at 4am when I was yanked roughly out of my cage. My hands were quickly secured behind m... Read full Story
shemale lover 2011-11-19 4,007 anal orgasm fantastic
100%
Just One of Those Days Part 2
Hello again. My name is Amanda, though sometimes I use the shortened version Mandy, when the mood suits me. I'm 33 and have stayed single for three years, since I discovered that Richard, my boyfriend, was not only cheating on me with dozens of women, some my so called friends but was al... Read full Story
shemale lover 2011-12-09 3,304 cum massage shemale sex
91%
My step mom turned me into a sissy slut for dad
When I was in High school I would spend the summers with my dad and step mom. She was so hot and always dressed sexy, They were always very playful about sex, not like my mom and step dad. I loved the atmosphere. During the week they would work all day and I would have the place to myself. I would ... Read full Story
shemale lover 2012-02-20 71,223 taboo Fetish
88%
My first time as a Femboy CD pt 2
David ordered me to dance for him and I hurriedly got off the floor and walked over to the radio and turned it on. I changed the station from an alternative rock station to a top 40 one, which was better for dancing. After I selected the station I moved to the center of the room and started to dan... Read full Story
Nicole_femboyCD 2014-12-03 21,228 anal Crossdresser Cumshot Blowjob rimming cd
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 8,660 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
100%
The Terrace View Apartments Part 3
Standing alone on the street outside the Terrace View Apartment complex, I found myself shaking uncontrollably with a mixture of apprehension and excitement. Physical exhaustion probably had a lot to do with my nerves as well. After all, I’d only begun what I had hoped would be a new life a fe... Read full Story
shemale lover 2011-11-18 3,426 anal cum oral crossdressing
83%
Discovering Amber
I have always enjoyed women's lingerie. From looking at catalogs to seeing girlfriends wearing it I have loved the look and feel of sexy, silky lingerie but for me it has always gone deeper. At 18 I tried on my first set of panties, oh my God that was wonderful! It was all downhill from there. Event... Read full Story
shemale lover 2012-09-28 6,274 Cumshot Fetish Lingerie oral sex
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 6,648 shemales Fetish bdsm
25%
Adult Bookstore Dancer
Adult Bookstore Fun At one time there were eight adult books in my city now there is only one. Makes me very sad as I loved dressing up like a twenty-five cent whore and visiting them on the weekends. I think I enjoy all the humiliating comments and condescending looks the customers would make abou... Read full Story
shemale lover 2012-02-26 4,255 sucking Fetish cross dressing
100%
Permanent Stay in Mastersville Part 4
My training was now reaching full speed and I was handling the maid's duties in the house, while at the same time spending a lot of time with sex training. Diane, on the other hand, was clearly reaching the end of her stay with Mistress. It was quit clear that a buyer would soon be found for her and... Read full Story
shemale lover 2012-01-08 4,590 toys bondage and discipline heavy reluctant
87%
Caught by my Sister Chapter 4
I woke up late on Sunday with the distinct taste of cum still in my mouth from the night before. For the life of me I couldn't even remember how many cocks I sucked at the party. I slowly got myself out of bed and took a long hot shower. It took me a long time to scrub all of the dried cum from m... Read full Story
shemale lover 2012-06-18 6,872 Cumshot Fetish Blowjob Lingerie
100%
How it began (1/x)
About two years ago I was in a relationship with a woman that I'd always considered to be out of my league. She was a tall, tattooed lady with black hair, who used to wear incredibly saucy dresses, knee-length boots and flamboyant make-up. Me, on the other hand, I have always been a quite unrema... Read full Story
sissylennie 2022-09-07 4,238 Crossdresser threesome domination mistress Cuckolding Cuckold Sissy
100%
How My Wife Became a Swinger
Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin. For the fi... Read full Story
Loveto 2011-10-12 8,739 anal bisexual gay strap-on
50%
How My Wife Became a Swinger
Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin. For the fi... Read full Story
shemale lover 2011-11-13 5,299 Group Sex Cumshot sucking doggy style
100%
First Date With Daddy
My Dream Date. It hasn't happened yet, but a girl can hope, this story is very short story based on my fantasy's. It was Sunday night and I had my first date lined up with daddy. We hadn't met, but we had spoken online at depth and exchanged numbers. I had sent him a couple of pic... Read full Story
SEXYBADGIRL 2023-03-17 5,139 Crossdresser Bareback Creampie domination
100%
End of the Beginning Part 2
The relieved pair headed to the shower. Matthew leaned over to turn on the water. Jamie realized she would have to remove her wig or it would be ruined. Matthew looked over at her inquisitively. “It’s a wig; I have to take it off.” Jamie answered to the unspoken question. “I ... Read full Story
shemale lover 2012-04-14 2,719 anal sex Creampie oral sex
95%
My TS Journey
I'm a straight, married guy in my 30's, at least that how I appear to everyone that knows me. I have an intense obsession with Trans women that I have been indulging since I was a teenager. Over the years this fixation has grown into something that ranged from watching porn initially, to having my a... Read full Story
iconicirish 2022-10-26 8,372 Amateur Shemale Fucks Guy Big Cock domination cum in mouth escort ts
100%
2.ΜΕ ΕΝΑ ΦΙΛΟ ΓΙΑ ΤΣΟΝΤΑ ΣΕ ΚΙΝΗΜΑΤΟΓΡΑΦΟ Μια φορα με πηρε ενας
2.ΜΕ ΕΝΑ ΦΙΛΟ ΓΙΑ ΤΣΟΝΤΑ ΣΕ ΚΙΝΗΜΑΤΟΓΡΑΦΟ Μια φορα με πηρε ενας φιλος μου να παμε να δουμε κινηματογραφο τσοντα.Δεν ηξερε τιποτα για εμενα οτι ειμαι crossdress.Εγω τις περισσοτερες φορες μεσα απο το τζιν φοραω καλτσες η καλσον ανοικτα απο κατω, σουτιεν η μπουστακι και φυσικα στρινγκ.Η αισθηση του ν... Read full Story
crossofia 2023-10-01 4,735 anal Stockings Crossdresser Amateur Group Sex Cumshot Masturbation Lingerie Sex Toys Mature big ass sissy cum in mouth
50%
Headmistress' Favorite Sport Part 8
For Denise her life as a fully trained slave began with a stay at Mistress Rachel's house before joining the twins' household. Since it was their idea to turn her into the sissy she now was, it was agreed that she would be their slave. But as the twins were moving out of Mistress Rachel's house and ... Read full Story
shemale lover 2011-12-13 5,965 torture toys bondage and discipline chastity belt
100%
David to Dee Chapter 2
His nipples had grown considerably over the last two months. Gina had been putting those little nipple suckers on him twice a day. Dave wouldn't be going to the gym anymore. Well, it had been a long time since he'd gone to the gym, anyway. Since Gina had had him shave his entire body, last spring... Read full Story
shemale lover 2012-07-30 5,860 anal sex Cumshot oral sex rimjob
100%
How I became a Transexual
I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I w... Read full Story
shemale lover 2012-04-15 3,340 anal transformation oral glory hole
100%
Wet & Messy Sex
It was the text I'd been waiting for for ages. 'I'm back.' it said. Anish, one of the kinkiest guys I've ever met had finally decided to return to his holiday home, just a few minutes away from where I live. He's a well off Asian businessman and has a lovely place to entertain. It's been a while sin... Read full Story
kiwicd 2022-04-27 3,568 Crossdresser Amateur Cumshot Creampie cum in mouth golden shower
71%
Filthy Little Beast
I had very few memories of my early childhood. The ones I did have were anything but pleasant. I did remember my mother and her blind hatred of my father and myself. She was very tall blonde woman with cold blue eyes named Monica. My mother always dressed in the most expensive leathers and satins in... Read full Story
shemale lover 2011-12-02 12,586 taboo Fetish crossdressing erotic encounters
66%
Chinese Extremes Part 4
The ride to Master's residence was completely uneventful for Lien. The whole way she lay in the trunk of his limousine, hooded and gagged, with her legs strapped together and her arms secured with the armbinder. The trip may have been uneventful, but Lien wasn't bored. She spent the whole trip fanta... Read full Story
shemale lover 2012-01-17 4,676 torture extreme bondage and discipline
100%
A Game within a Game Part 1
Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... Read full Story
shemale lover 2012-03-05 14,356 Fetish bdsm crossdressing bisexual
25%
A Strange Romance
Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to ... Read full Story
shemale lover 2012-07-05 6,972 Creampie Fetish crossdressing virginity
100%
Tony to Tanya
My name is Tony and I'm an average 19 year old boy. I'm 5 foot 7 inches tall, have shoulder-length brown hair and blue eyes. I often get mistaken as a girl from behind because of the length of my hair and because I look after it really well. I've been told I'm as good-looking as most girls my age. M... Read full Story
shemale lover 2011-12-19 4,384 cum dildo ass fucking
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 11,101 Fetish crossdressing feminization
85%
Alternative Plans
Another Goth Trans Girl Confession I really enjoyed my first sexual experience. I had gone to the local adult entrainment store and purchased some toys; a butt plug, a 10inch purple dildo, some lube and condoms. I would occasionally play with my toys while watching some internet porn. I loved ro... Read full Story
Gothtransgirl41 2017-11-10 11,323 domination cum in mouth quickie
100%
The Greatest Lie Part 4
Don’t get me wrong, I don’t hate being around people. Actually, I hate being alone: it brings out the weird self-critic inside me. But god, do I hate crowds. Fall registration brought mobs to the campus. The half-empty dormitory that I had shared with a few Asian engineering students was... Read full Story
shemale lover 2012-01-19 4,777 taboo femdom crossdressing