Sort by
Relevancy

Free Stories

100%
Down the Path Part 3
I haven't been able to concentrate all day, didn't get anything done. All I can think about is having to go back to the bookstore tonight. I don't know if I can do it but if I don't I'm not sure what he might do. Maybe he just won't contact me anymore and I really don't want that. More troubling is ... Read full Story
shemale lover 2012-09-17 5,671 cum oral cum swallowing
100%
Five Into Three Does Not Go
Kristina It is waspish in the late evening out in the open in Portsmouth Harbour as we step out of the vehicle and walk over to the private section of the docks, the sign says Ceres St docks. Dark has long since fallen but lights, white, yellow and orange light up the skies. The feeling is one of... Read full Story
shemale lover 2012-11-07 4,756 cum oral sex Sex Toys
100%
Dress Up For The Girls Next Door Part 2
“Hot enough for you?” I looked up from the garage to see Lisa hanging her head out the window. She had a sexy turquoise halter on. Her tits bounced back and forth as she spoke. “Now it’s real hot with you hanging out the window.” No bra, Lisa never wore a bra when it... Read full Story
shemale lover 2012-11-19 3,598 sucking fingering cum swallowing
100%
Andre Becomes Andrea
I was in my first year of college. I was having second thoughts about the major I had declared: Psychology. I figured I was probably going to have to change it to something else. I went to a local University and was living in my brother's basement. I was not into the party scene, and having just tur... Read full Story
shemale lover 2012-11-28 4,357 first time orgasm sucking off
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 13,971 Masturbation cum orgasm cumshots prostate
60%
The Creators: Book One by
Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... Read full Story
sagga 2018-09-18 30,495 Teen (18+)
50%
DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
Femboy 2021 2023-02-07 1,467 Stockings Lingerie Shemale and Girl Guy Fucks Shemale Interracial Sex Toys cum in mouth
100%
Headmistress' Favorite Sport Part 4
Over the next weeks Denise and the others settled into the routine, accepting their new life. Cindy did, as Mistress Hoffmeyer had predicted, break very easily and now she had been remolded as the slave-sissy her master wanted her to be, docile and obedient. Others needed more effort and others less... Read full Story
shemale lover 2011-12-12 7,639 torture toys bondage and discipline chastity belt
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 4,711 torture toys bondage and discipline chastity belt
0%
Headmistress' Favorite Sport Part 9
When Denise returned from the academy all this was taking place without her knowing about it. She started her new life as a maid in Mistress Rachel and Master Tony's house alongside her mother, Susanna. Susanna had in the meantime developed into a complete slave, craving punishment and humiliatio... Read full Story
shemale lover 2011-12-13 5,658 torture toys bondage and discipline chastity belt
100%
Story for adults Part 5
Alice's life continued like that for a couple of years until one day Mistress Angela got fed up with Janice. Janice had never really been into the S&M-bit and in time this began to annoy Mistress Angela. At the same time Mistress Angela began to regard Mistress Jensen as just another freeloader.... Read full Story
shemale lover 2011-12-20 4,346 bondage and discipline heavy feet reluctant
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 9,452 transgender toys bondage and discipline heavy
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 4,429 toys bondage and discipline heavy reluctant
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 4,674 torture extreme bondage and discipline
20%
Chinese Extremes Part 7
Life as a slave continued for Lien and the others. Sucking, fucking and punishments in and endless cycle and only very rarely were they rewarded with an orgasm. About once a year they had the chance to be granted an orgasm, but only if they had been exceptionally good and lucky were they actually gi... Read full Story
shemale lover 2012-01-18 3,335 torture extreme bondage and discipline
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 8,352 Fetish transformation dildo
100%
Eve Quest
Chapter 1 My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy. My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,... Read full Story
shemale lover 2012-04-21 6,478 domination oral sex transvestite
100%
Eve Quest Part 2
Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed s... Read full Story
shemale lover 2012-04-21 4,376 bdsm domination transvestite
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 4,188 anal sex domination oral sex transvestite
50%
A Revenge Fuck
It had been a long day. I had fought the traffic after a miserable week to get home early and surprise my wife for what was to be a romantic weekend. But as I pulled up to the house my heart sank. I saw a bright red motorcycle in the drive way and something inside told me, "This isn't right!&qu... Read full Story
shemale lover 2012-06-03 11,279 shemale oral sex Interracial
100%
Feminized by My Girlfriend Chapter 2
I followed Brook and Linda out of the spa onto the sidewalk and I looked around for the limo but it was no where to be found. As the girls started walking down the street and talking to each other, I asked where the limo was. Neither of them responded and just kept walking. I followed behind as clos... Read full Story
shemale lover 2012-07-14 13,807 Fetish oral Sex Toys feminization
100%
Serving Waitress
This is the first “didi” story I ever wrote. It’s my deepest (and darkest?) fantasy. It probably needs to be rewritten at some stage because I think it’s been written too much by my male brain and not enough by my female side. The story begins….. My wife, Susan, ... Read full Story
shemale lover 2012-08-28 4,864 anal sex Cumshot Creampie oral sex
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 5,959 Fetish domination cum swallowing feminization
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 5,190 fingering domination handjob spanking little dick
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 9,087 Stockings sucking domination
100%
His Ultimate Fantasy
Jeff and I had been back together for a little over 5 years when I had decided to give him his ultimate fantasy. To everyone who meets him, Jeff is the all American boy. He is the quintessential small town boy. He always has impeccable manners, says his "ma'am's" and "thank you's"... Read full Story
shemale lover 2011-10-08 4,499 shemale orgasm pussy licking
69%
From Mob to Shemale
Two years ago, I was a member of the Ciccio family in Chicago. I wasn't very high up in the organization, because I wasn't Italian. I had made my way up through the ranks, however, and was making a pretty good living. I had everything I wanted, got all the girls I wanted, and did just about ... Read full Story
shemale lover 2011-10-29 10,613 orgasm facial oral sex
71%
A Night of Makeup, Cock and Cum - froam Annamalice
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further, I... Read full Story
shemale lover 2011-11-21 5,228 shemales Group Sex Fetish
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 6,155 bondage and discipline heavy feet reluctant
75%
Story for adults Part 4
Alice's place in the household proven to be quite complicated and very demanding. First and foremost she was Mistress Angela's slave and her needs came first. Pleasing and servicing Mistress Angela and Mistress Janice both sexually and otherwise took up a great deal of her time. Her life acquired a ... Read full Story
shemale lover 2011-12-20 4,398 bondage and discipline heavy feet reluctant
50%
Debbie Part 6
Debbie was awakened by someone holding a hand over her nose and mouth, so that she couldn't breathe. She struggled, weakly tossing her head before opening her eyes. She looked straight into the eyes of Dr. Jacobsen, smiling evilly down at her. He continued to hold her head so that she couldn't breat... Read full Story
shemale lover 2011-12-23 4,482 transgender toys bondage and discipline heavy
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 31,148 strapon porn
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 12,319 sucking Fetish crossdressing
100%
A Night of Makeup, Cock and Cum
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further,... Read full Story
shemale lover 2012-04-18 4,832 Cumshot jerking off domination Sex Toys cum swallowing
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 4,518 transformation oral sex cum swallowing
50%
A Perfect Life
The reasons I am not writing this myself. I have finally convinced someone to do it for me. She promised to post it on the Internet, but only as fiction. I suppose it is a bit unbelievable. It all started with the best of intentions. I had married my love while we were still in college. She... Read full Story
shemale lover 2012-05-05 12,720 transgender
88%
Feminized By My Mother
Hello. My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is inv... Read full Story
shemale lover 2012-07-24 67,560 Fetish shemale oral feminization
100%
Discovering Mistress Sarah's World Part 8
Part 8 -- Complete Surrender Chapter 21 Leaving Behind Joe's Life Mistress Sarah was very pleased with Josie's training and feminization. She was anxious to have complete reign over him so she sent him home a day early to pack up his things and prepare to leave behind his life in the Philadelp... Read full Story
shemale lover 2012-10-04 5,184 sucking cum strapon
100%
Property To Be Pimped
It had been weeks since I'd brought to light my idea of my wife, Suzie, strapping on a big dildo and taking me dressed as Desiree, the Hot to Trot Transvestite. While at first she teased me with possible participation, it never came to be, despite me bringing it up on several occasions. She really d... Read full Story
shemale lover 2013-01-17 7,367 Stockings Crossdresser sucking dildo Interracial
100%
Jamie is taken Part 3
When this process was completed the Chinese gentleman s turned to his new acquisition in the floor. He lifted him up from the floor and deposited him on a high-backed chair; his legs still folded up, and tied him to it. Then he removed the strap from around his throat and instead shoved ... Read full Story
shemale lover 2011-11-30 6,494 Fetish domination bondage facefucking
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 7,034 torture toys bondage and discipline
71%
Headmistress' Favorite Sport Part 2
Over the next week the twins trained him further. He was taught how to apply make-up and how to behave in a properly feminine and submissive manner and they trained his movements to be properly feminine. So as not to wear the skin of his ass, the twins introduced a new punishment tool for these trai... Read full Story
shemale lover 2011-12-12 4,961 torture toys bondage and discipline heavy
100%
Interstate Reas Area Whore
Driving down the interstate the sign said Rest Area one mile. My heart skipped a beat and there was slight stiffing of my male meat in anticipation of events to unfold. This interstate rest area was always packed full of eighteen wheelers as many as forty. Surely one or two of these truck drivers wo... Read full Story
shemale lover 2011-12-27 3,757 shemales oral whore
100%
Summer School
Dan woke to the sound of birds softly chirping outside his apartment window. Excited, he sat up realizing that he now finally had the apartment to himself the entire summer. He could do what he wanted and wear what he wanted. No longer did he have to keep many of his "pretty things"... Read full Story
shemale lover 2012-01-30 3,880 sucking cum fingering fucking
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,679 Cumshot Masturbation oral sex
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 5,412 Cumshot fingering Sex Toys feminization
100%
Down the Path Part 5
I force myself to walk down the corridor and to the elevators. When the door opens there is an older couple in the elevator and I get on and move to the other back corner. The man's wife is standing a little in front of him and I see him look over at me briefly. Then he looks again, giving me the on... Read full Story
shemale lover 2012-09-17 5,434 Fetish cum oral domination
100%
Brian Becomes Brittney
My name Is Brian or at least it was the first 18 years of my life. Brittney is my new name.... All of this started when I was just out of high school. It was the beginning of the summer and I was feeling great. During the summer I was planning to do a study abroad program for a year before colleg... Read full Story
shemale lover 2012-09-21 4,843 domination oral sex Sex Toys
100%
Dress Up
I don't know how to explain it. I am not gay although I may be passive bi. I have had sex with men, but not a lot and I have always been the one receiving, you know once a friend showed me a pack of pictures of his wife from fully dressed in conservative suit to complete nude with some action photos... Read full Story
shemale lover 2012-11-17 4,637 Fetish cum oral sex Sex Toys cum swallowing
90%
Brian Becomes Brittney Chapter 1
My name Is Brian or at least it was the first 18 years of my life. Brittney is my new name.... All of this started when I was just out of high school. It was the beginning of the summer and I was feeling great. During the summer I was planning to do a study abroad program for a year before colle... Read full Story
shemale lover 2012-12-21 5,309 Teen (18+) Crossdresser domination Sex Toys ts
80%
JUERA MARICON
My name is Keven Jeanne and, Yes, I am a Sissy! When I was 13 I put on my mom's panties and some of her lipstick when she was at work. I had longish blonde hair and I ruffled it up - kind of teased it up - and when I looked in her dresser mirror, I almost ejaculated. Because what I saw looking ... Read full Story
Kevyn-JeanneHarris 2015-12-25 6,433 blonde shemale submissive cocksucking
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 12,880 Guy Fucks Shemale
66%
wishing
When I would get off the bus from after school activities, I would always walk through this truck stop on I-94 east of the Twin Cities. I would always look at the truckers parked for the night in the back. I always wondered what would happen if I brought my desires and fantasies to life for one of... Read full Story
cd4fun715 2019-01-08 2,965 Crossdresser Amateur
66%
Cock Sucking Jail Whore
I've always known that I was not meant to be a guy. Being sexual curious I would look at porn mags like any one does. At first it was just magazines with pictures of naked woment. It was when I ran across my first Hustler magazine that my life was changed forever. Seeing pictures of studly guys with... Read full Story
shemale lover 2011-09-17 4,525 Cumshot asshole oral sex
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 5,224 shemales Blowjob cum
87%
The Hotel Part 1
I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days. Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, fucked fem, huge dildos, and giant buttplugs are just a few of my fetishe... Read full Story
shemale lover 2012-02-11 6,163 Fetish cum domination Sex Toys