Sort by
Relevancy

Free Stories

31%
Headmistress' Favorite Sport
When Susanna lost her second job only two days after losing her first; she had no choice but to accept her sister's kind invitation. Susanna had been loath to do so because of two things. Firstly there was pride. Although she had accepted Rachel's offer of help with paying for the children's school,... Read full Story
shemale lover 2011-12-12 6,772 torture toys bondage and discipline
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 9,115 transgender toys bondage and discipline heavy
50%
Chinese Extremes Part 5
One morning Lien was one of three sissy-slaves were cleaning the slave toilets. The two others were using their tongues to clean the floor meticulously. Meanwhile Lien was using her tongue to clean the toilets. She was carefully licking the funnel leading down into the mouth of castrated toilet-slav... Read full Story
shemale lover 2012-01-17 3,991 torture extreme bondage and discipline
100%
A Downtown Moment
I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the compa... Read full Story
shemale lover 2012-02-28 4,703 pantyhose mistress
88%
Last night I drank my own cum
Once upon a time... There was a regular boy, who was always fascinated by women, but one day (casually) discovered the dirty and horny world of the "third way" of sex, the fantastic shemale-ladyboy-tranny universe, and it was like a shock for him, a very sweet shock, he never believed o... Read full Story
shemale lover 2012-03-03 3,634 Masturbation cum cum swallowing
100%
Nylon and Lace Part 2
Next thing I know is I'm having this fantastic dream, an erotic dream. I can't see faces or bodies or who is there, but a hundred thousand hands are softly caressing my body. They are specially interested in my legs, then my belly, then my butt. The number of hands are diminishing, but the intensity... Read full Story
shemale lover 2012-05-14 2,312 jerking oral sex finger fucking
75%
On School Grounds
It’s amazing how good the cloth feels against your bare skin. I had never thought of myself as anything but a straight and regular Joe. I didn’t think that I’d get a stiffy wearing woman’s clothing like this. I looked at myself in the mirror, just to see if my padding was ... Read full Story
shemale lover 2012-09-05 2,383 Crossdresser Cumshot Masturbation
100%
FMDM Inc - The Interview
I had just finished a therapy session and was glad to get back to my office and relax. I'd have to lay off the cinnamon stix in the morning, my bustier was tighter than usual. My mini-frig offered a variety of drinks and I grabbed the pitcher of iced tea and poured a glass. Settling into the rich... Read full Story
shemale lover 2012-11-14 3,180 Cumshot Fetish domination
86%
Goth Trans Girl Confession pt1
This is true confession. A journal entry of sorts. Sep. 2009 Anyway, I would say that my family is pretty open, at least compared to most of the families of trans people that I personally know. That doesn't mean that I didn't have a difficult time as far as there understanding when I my... Read full Story
Gothtransgirl41 2017-11-10 14,331 first time Bareback Creampie Blowjob
92%
Shy boy to bimbo sissy
it's all started when my older brother showed me a shemale masturbating video when I was 15. after I saw it I was instantly attracted to trans girls than cis girls. I was a very shy pale feminine looking boy.high school wasn't great, boys used to bully me. I am too shy to talk to the girls... Read full Story
drleena 2022-12-08 12,578 shemale submissive cross dressing chastity prostitue real story
100%
CD Gone Wild
I'm a little CD slut, and get strong sexual urges that I can't control or resist. I think I'm far from passable, but men seem to think otherwise. Some men value a slut as a precious thing; the kind I look for. For that reason, I'm proud to be a slut. I love to be told what a slut I am; being called ... Read full Story
PetiteSlutKimberley 2023-03-30 5,858 Creampie bareback anal sex bbc fucks cd
100%
Lucky Little Slut
Last weekend I wrote to my beautiful TS sister Roxanne to see if she wanted to play. We had done some group sex play a couple of weeks earlier and I was anxious to take it to the next level. She was as excited as I was to get the chance to play again. When she arrived we went to my in-home theatre a... Read full Story
PetiteSlutKimberley 2023-04-18 4,671 ts bbc bareback fucking cd slut Sister Play
100%
Mikaela Lilyskin My story
Hello! My name is Mikaela. I want to tell you a little bit about how I became a "Tranny" I grew up as a normal straight guy. When I was 15 years old, I was looking at a porn magazine and saw an Asian girl with a cock. Oh my god, how horny I got. I jerked and jerked to those pictures for several m... Read full Story
Mikaela Lilyskin 2024-03-27 2,681 tranny Amateur Cumshot shemale masturbating
90%
One Night In Heaven
As I arrived at Ginny’s place she met me at the door dressed In a see thought black dress stocking clad legs and high heeled shoes We kissed and cuddled a t the door and then she turned round to lead me into the front room. As she turned I saw her sexy ass and my cock started to get hard. ... Read full Story
shemale lover 2014-12-05 5,430 anal first time shemales
100%
Don't Go Into The Woods
Prologue I am standing here wearing a red plaid schoolgirl uniform skirt. It is so short that although I looked in the mirror before and couldn’t see my white satin panties I felt anyone looking at me could. My blouse is a white collared blouse typical of what you’d expect to see on a... Read full Story
shemale lover 2011-11-10 5,010 sucking Lingerie spanking
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 4,461 torture toys bondage and discipline chastity belt
100%
Headmistress' Favorite Sport Part 12
At the academy little had changed. As Denise was being led through the hallways, bound and gagged with a leash attached to her chastity device, she saw new sissies in training hurrying to class, eager to please the mistresses and to avoid punishment. The new sissies tried not to stare at Denise, but... Read full Story
shemale lover 2011-12-14 4,337 torture toys bondage and discipline
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 5,954 bondage and discipline heavy feet reluctant
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 2,607 anal sex shemale deepthroating
100%
Eve Quest Part 3
Sometime during the night I was released. That exquisite pain at the point my limbs were release must have dulled my recollection of the events. I'm reasonably sure I was given the Toilet command and I hope I did a good job. In any event, I was still on the bathroom floor when I heard my mistresses ... Read full Story
shemale lover 2012-04-21 4,218 transformation oral sex cum swallowing
80%
Michele And The Predator
The predator peered through the bedroom window and smiled; he couldn't believe his luck. This woman was just to his taste; he felt himself begin to stiffen as his eyes devoured her; he couldn't wait until he had his hands on her. In his mind he played out the scenario that he envisaged would soon ta... Read full Story
shemale lover 2012-05-13 4,249 Fetish transvestite fiction
100%
Body Image
"Sit down Mona. We have to talk." He had heard those two tiny sentences more than a few times in the last several weeks. Every time he did he felt a strange queasiness in the pit of his stomach. Yet no matter how hard he tried, he could not refuse. He walked over to the couch across fro... Read full Story
shemale lover 2012-07-23 7,055 Fetish domination submissive
100%
Shemale Whore and Arab Pimp
Hermaphrodite Whore It had been over a year since Johnny threw that tantrum that ruined me and got him excommunicated from mom. Holding me down when mom walked through the door with her friends, colleagues, whatever and they all gasped and screamed as my big brother finished doing me. We had... Read full Story
shemale lover 2012-07-24 2,894 anal sex Cumshot oral sex hermaphrodite
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,070 Crossdresser Cumshot Blowjob jerking pantyhose
76%
My Wife's Secret Fantasy Chapter 1
PART ONE: REALIZATION The old saying "you never really ever know some one" is quite true when it comes to my wife Debbie. Debbie has always seemed to come up with new surprises to keep our marriage stimulated and adventuresome. As I've recently found out though she seems to have been ke... Read full Story
shemale lover 2012-09-09 9,709 Crossdresser Cumshot Masturbation Lingerie heels
100%
Hidden Surprise
After staring at Angela's crotch for what seemed to be forever, the shocked young woman asked, "I-is that what I think it is???" "I guess it depends on what you think it is," Angela replied softly. "But how, why???" Midori asked. " I mean you have a cock for christ... Read full Story
shemale lover 2012-09-17 2,901 Cumshot oral sex
100%
Am I Who I Think I Am? Chapter 2
Well,I can't lay here all day and dream! I feel so good, so loved, so ravished. My smile is touching the pillow on both sides! I'm laying here daydreaming about my deflowering this morning. Inside me lives my lover's DNA, looking for a life to create. (Nice try little spermies, but you won't find it... Read full Story
shemale lover 2012-10-19 3,376 Cumshot sucking Fetish
100%
Sultry Mistress,
Sultry Mistress, Natacha has now been living with me for over a year. It is a cerebral and perverse Domina who immediately wanted to submit me to her desires. She took power over me by making me discover my femininity during role-playing games. Like a spider, she imprisons me in her web a ... Read full Story
sandratvtg 2022-09-20 3,831 Stockings Amateur Lingerie domination Sex Toys
100%
My wife turned me into her tranny
It all started after our marriage. We have been together for 12 months when she asked me if I would be willing to have her dress me up like a female as this was one of her fantasies. Little did I know where this would lead us to. She was very secretive about her job and I did not bother to ask, I fi... Read full Story
TRTRAIN 2024-01-15 7,029 Stockings Crossdresser Amateur Shemale and Girl domination pantyhose Homemade sissy shemale fucks female
85%
The invitation
The envelope was waiting on the mat when Jack and Sally got home from college to the small house they shared in North London. Sally scooped it and what was obviously yet another bill up from the floor and plonked them down on the table in the hall as she shrugged off her coat. The young pair were se... Read full Story
shemale lover 2014-12-15 6,599 shemales Fetish
80%
Leila
I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most. It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before. I'd stayed over at a friend's house and af... Read full Story
shemale lover 2011-09-27 3,486 sucking shemale stroking
100%
Permanent Stay in Mastersville Part 2
I had some time to think about this as she dragged me out the front door and threw me into the backseat of her car, shut the door and left me there as she went back into the house. I sat there in the car thinking about what would happen to me, if Mistress had really meant what she had said about tur... Read full Story
shemale lover 2012-01-08 4,235 toys bondage and discipline heavy reluctant
100%
Taken with a Strapon
I think I can trace my new addiction back to a short fling I had with a girl a few months back; I'm 22 years old slim; about 6', and fairly good looking. Not trying to be conceaded but simply stating girls would be atracted to me however it would be difficult for me to progress with them because... Read full Story
shemale lover 2012-01-18 3,422 anal shemale vibrator
66%
A Perfect Cuckoldress Wife
My wife rose slowly, before lowering herself down his length again. Her head tipped back, she squeezed her breasts, playfully teasing her own nipples. Her eyes opened, lustfully admiring the chiseled ebony body of her lover. Balanced skillfully on her stockinged toes, she began picking up the tempo ... Read full Story
shemale lover 2012-04-30 4,934 Cumshot Creampie Fetish crossdressing
100%
Erotic Daydreams
Sometimes I think my parents should have named me Eykan, rather than Eukan. Since I was old enough to get an erection, I have masturbated one or more times a day, three hundred sixty-five days a year. I don't know how much semen I have spilled, but I'm sure that were every sperm in it had impregnate... Read full Story
shemale lover 2012-06-28 2,934 Cumshot Masturbation fuck
100%
Brad's Bitch
The phone rang. I pulled it from my jeans pocket and saw that it was Brad. Shit! I really didn't want a call from him right now. Maybe I should just ignore it. But somehow he always knew when I'd just ignored his calls. And then that was even worse. I answered it, thinking only fleetingly about &... Read full Story
shemale lover 2012-08-21 4,691 cum oral sex missionary style
80%
T & T
My "Sister" and I have always been close growing up, we've shared "almost" every detail with each other, or so I thought. I say "Sister and Almost" very loosely, but neither have hardly any truth to them. My name is Anthony, most call me Tony, my sister's name is Terran... Read full Story
shemale lover 2012-08-28 5,106 anal threesome Blowjob rimjob
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 5,689 Fetish domination cum swallowing feminization
100%
Downsizing
Being frail and weak is a gift that not many men see the beauty of. Most consider it a punishment or something of that nature. There is another gift that many men don't see. That gift is affirmative action. Most other people lose the chance at some excellent jobs because of their race, creed, sex, e... Read full Story
shemale lover 2012-11-10 3,595 Cumshot sucking Blowjob
100%
Leila My Hermaphrodite Lover
I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most. It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before. I'd stayed over at a friend's house and after a ni... Read full Story
shemale lover 2012-12-17 3,970 taboo Cumshot shemale Mature
100%
Christy's Fantasy Come True Chapter 6
The alarm went off and Christy rolled over and hit the off button. The clock face was starting back at her flashing 8:00. Since it was Friday she had slept in a bit. Jim had gotten up early and left for work after spending the night. They had gotten into a minor argument last night but came to a... Read full Story
shemale lover 2013-01-30 4,909 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
88%
Tipping Point -- Chapter 1: Blow by Blow
Chapter 1: Blow by Blow October 12th Thursday evening. Tick, tick tick... the minutes pass by while Nick lies on his back, staring at the white ceiling fan that hovers above. He raises his head, bats his eye lashes, and yawns. His long, wavy, auburn hair falls down his back with small curls. ... Read full Story
Danielle Pillory 2015-11-24 5,185 anal shemale domination spanking submission
69%
Hormonal Family
Hormonal Family My name is Phil, a fairly normal middle-aged guy with a family composed of my wife, Carol, and kids, a son Billy who is 16, and 2 daughters, Sharon who is 19 and Cindy who is 14. I have always been the type of guy who is totally in control of almost every situation in my life w... Read full Story
PattiCake 2017-12-05 13,422 dominated hormones tamed bad boy to Good Girl
100%
My Afternoon With Venus - Part I
It was a stunningly bright and clear Saturday morning when I left my house to head out and run some errands. Nothing big, just little odds-and-ends that had been building up that I needed to deal with someday and it seemed like this was as good a day as any ... little did I know how good the day wou... Read full Story
funpics 2018-03-23 12,886 Amateur Shemale Fucks Guy Asian Guy Fucks Shemale Homemade
100%
Lady In The House Ch. 08
A story by MicheleNylons (Crossdresser must comply with jailhouse heavy.) "You!!!" Eddie screamed through the bars, then laughed. "Well done girls, quite a show, I really enjoyed that; and so did Michele obviously," he said snickering and pointing at the tent in the front of my skirt caused by... Read full Story
✘Transensual✘ 2019-02-25 5,541 Crossdresser domination PRISON PUNK prison sex Prison Bitch
100%
Lady In The House Ch. 09
A story by MicheleNylons ( Continued adventures of a cross-dressed prison prostitute. ) I lay there stunned, how had I miscalculated my effect on the Warden? The one man who could guarantee a transfer from this shit-hole; fuck!!!! The cravings of male sexual hunger within the confines of the ... Read full Story
✘Transensual✘ 2019-02-27 5,635 Crossdresser domination Guy Fucks Shemale cum in mouth PRISON FUCKBOY PRISON PUNK prisoner Prison Bitch
92%
My Neighbor
When I got divorced and was finally living alone I had many fun times getting fucked all I could by both men and women. I was always dressed when home and loved to stay that way all weekend long and would just put on some pants over my outfit to go shopping sometimes with a coat or shirt over my ope... Read full Story
crossdresser55 2019-10-29 16,294 Stockings Crossdresser
100%
Camming down the rabbit hole Ch1
Back in January 2020 I guess I was lucky, I did have a regular job although the pay was miserable and I did have my own place. On my wage all I could afford was a miserable bedsit in a neglected part of town, but on the upside I didn’t have to flat share and it worked well enough for me. The west... Read full Story
Dani_does_Dallas 2021-08-11 5,143 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
100%
The Girl Next Door Ch. 02
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 s... Read full Story
Gwapo67 2022-05-13 5,089 Bareback Creampie Guy Fucks Shemale cum in mouth
83%
A Stay At Cousin Clare's
As a teenager I always used to spend about ten days each year with Cousin Clare and her parents. Clare wasn’t actually my cousin, but her mother and my mother were at school together, and it was a convenient way to refer to her. Clare was an only child. At the time of the following exciting adve... Read full Story
lacemint 2023-08-29 6,164 Crossdresser sissy cum in panties panties crossdresser knickers Cousins clothes
84%
The Truckers Reststop
I had to work yesterday, it was Saturday,I had made plans to spend the day being the slutty little whore for the whole day, but work got in the way. I came home felt tried so I soaked in the tub, shaving my legs and puss yass and gurly clit. The weather was bad all day, when I finally decided to Fem... Read full Story
bigtranslover 2014-02-07 13,165 shemales gay male voyeur
80%
Buffy the Shemale Vampire Slayer Part 13
Buffy's cock slipped out of Baubo's mouth, and she licked the smooth skin of the stiff, elongated shaft with her tongue. Baubo had no hands, but, even so, she was a superb cock sucker. More than once, she brought the Slayer to the brink of orgasm, then backed off, letting Buffy's sexual passion abat... Read full Story
shemale lover 2011-08-23 3,593 Masturbation pussy shemale
40%
Bewitched, Bothered And Bewildered Part 2
Still sitting beside Vivian, his mother put the catalogue down and shuffled closer so he could feel the warmth of her thigh against him. She took hold of his right hand, brought it to her lips and kissed it. “Can you do it left-handed?” she said, squeezing his fingers affectionately. ... Read full Story
shemale lover 2011-10-15 3,065 Stockings crossdressing feminization
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 6,475 Stockings shemale oral sex bisexual
100%
My Beautiful Surprise
Mark Holloway groaned as he sat up in bed and reached behind him to touch Madison. It was six o'clock on Saturday morning in Birmingham, Alabama. His hand met only a cool pillow and undisturbed sheets. Then he recalled with an increase in his heartbeat that she was due to arrive at the Birmingham In... Read full Story
shemale lover 2011-11-01 5,693 sucking shemale cum
50%
The Sweetest Taboo
"Hey sis! Remember me?" Tisha Roberts stood at the door in complete shock looking at the person in front of her, the latest KaySlay CD whispering its aural presence in the background. She scanned the person in front of her, trying to figure out what was going on. The woman in front of h... Read full Story
shemale lover 2011-11-14 5,170 Cumshot cum swallowing handjob