Sort by
Relevancy

Free Stories

100%
Becoming Amy
I had been dressing up in women’s clothes since I was a kid. Started with my sister’s clothes, I loved her school uniform. I used to prance around in it when I was lucky enough to have the house to myself, which wasn’t often. I loved pretending I was a school girl, and a rather nau... Read full Story
shemale lover 2011-12-06 6,671 anal shemales bdsm
100%
Just One of Those Days Part 3
Hello again. My name is Amanda, I'm 33 and single, since I discovered that Richard, my now ex boyfriend, was a nasty cheating bastard. He turned me into the woman I've become, confidant exhibitionist and uninhibited, especially with sex. I'm a natural blond with long hair nearly down ... Read full Story
shemale lover 2011-12-09 3,692 sucking
100%
Special Shemale Fun
Everyone in the hallway jumped slightly, turned and quickly looked at the tall girl near the sound of the slamming locker. Satisfied that there was no crisis at hand, the kids at the school mostly went about their business. Of course, there were the few admirers that glanced at the girl at the locke... Read full Story
shemale lover 2012-02-06 4,973 sucking shemale massage
100%
The Shop
I lunged backwards to get more of him in me. I heard him grunt as half of him slipped passed my tight sphincter muscle. The pain was in the back of my mind, somewhere but this unbelievable feeling of lust had taken over me. I looked over my shoulder (what a sight that must of been, a 18 year old ... Read full Story
shemale lover 2012-04-12 3,537 anal sex Fetish crossdressing facefucking rimjob
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 3,628 sucking Fetish Ladyboy rimjob
100%
Angel Chapter 6
This is an entry in the Literotica Winter Holiday Contest, and is part of an ongoing series on the life of Angel Jones, a beautiful young T-girl in London. For more detailed information on her and on the other characters who appear in this story, please see previous episodes. Angel Jones was uns... Read full Story
shemale lover 2012-12-01 3,984 Cumshot oral tgirl
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 13,518 Masturbation cum orgasm cumshots prostate
100%
Lady In The House Ch. 05
A story by MicheleNylons (Crossdressed prisoner is forced into prostitution.) From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread th... Read full Story
✘Transensual✘ 2019-02-25 4,267 Crossdresser domination PRISON prison sex
100%
Every Year
Imagine me. A slim eighteen year old boy, dressed. I mean Dressed. Dressed up that is, in my sister's clothes. I felt good, very good. In fact I felt incredible. I had done this several times before when my parents had been away but never to this extent. They were away for two nights, visiting Uncle... Read full Story
shemale lover 2012-04-22 5,273 Cumshot oral sex deepthroating crossdressing
66%
Mistress Jasmine Made Me a Slave
Since long I haven't written a story so maybe I am a little rusty but I hope you enjoy it anyway. There are some autobiographic parts in it but most is fantasy, which part is real and which is fantasy I leave to you. Like any other author I do love comments too, whether they are good or bad. So plea... Read full Story
shemale lover 2011-09-23 9,077 asshole bdsm fingering dominant
100%
A Night Out
One night I was out on the town. I headed out on my own as all my mates where shacked up with their girlfriends. It used to agitate me that my mates never came out anymore. It didn't take me long to get used to it. I'm an attractive guy in general, a little on the shy side but still did alright for ... Read full Story
shemale lover 2011-10-05 4,951 anal Cumshot oral
66%
The House of Lesslie
I. The mansion hadn't changed, not all that much, from how I remembered it. If at all, it had aged gracefully, as only English mansions can ¬ a massive Edwardian building that had served Lords and Ladies, had housed masters and servants for centuries. Around it, at a respectful distance, w... Read full Story
shemale lover 2011-10-14 5,352 pissing domination Latex
100%
Marilyn: Going Your Way
"Oh yes…eat me…ooh yeah…" Marilyn was laying on one side, watching her sister Sharilynn get gently eaten by Kat. Marilyn herself was bottomless, letting her limp dick hang down to recover from soreness. Yes, it was one of those weekend afternoons that stretched into... Read full Story
shemale lover 2011-11-08 3,331 sucking orgasm nipples
50%
The Invitation Part 5
This is the latest installment of a story about cross dressing and the changes in a relationship between a young man and woman at college. Bits are autobiographical, but not as much of it as I would like! If this is illegal where you live, don't read it. If this sort of thing offends you, don't ... Read full Story
shemale lover 2011-11-20 3,091 Fetish crossdressing feminisation
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 5,991 anal Creampie oral
100%
Mistress Jasmine made me a slave forever
I should have been honest. I mean I should have known that lies have short legs and now they had caught up with me. The worst was I had not only lost my place in my bed but had also lost my place with my wife. Somebody else occupied these places now. Let me tell you how everything went. More ... Read full Story
shemale lover 2011-11-26 11,165 Big Cock orgasm domination
0%
Jamie is taken Part 4
Jamie was now in great pain; his back felt like it was breaking and his balls were being crushed, but the presence of Master's cock in his mouth and throat focused Jamie's mind. Since arriving in Master's dungeon Jamie had undergone a change. He no longer thought of escape or of how shor... Read full Story
shemale lover 2011-11-30 3,298 orgasm domination bondage
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 12,217 taboo Fetish crossdressing erotic encounters
100%
Debbie Part 5
Debbie didn't wake up until her gag was wrenched from her jaws. Her hood, collar and earplugs had already been removed. "Wake up, shit-head," Mistress spat and slapped her face hard. Debbie came awake and noticed that all the straps holing her to the couch had also been removed. She felt a... Read full Story
shemale lover 2011-12-22 5,189 transgender toys bondage and discipline heavy
66%
Chinese Extremes Part 1
Phil had been looking forward to the competition for weeks and now that it was over, he felt slightly disappointed. Not that he really had anything to be disappointed about. He had advanced to the third round in the Karate tournament where he had met an admittedly better opponent. So it wasn't that ... Read full Story
shemale lover 2012-01-16 4,452 torture extreme bondage and discipline
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 8,346 torture extreme bondage and discipline
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 3,954 torture extreme bondage and discipline
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 5,812 Fetish cum domination Sex Toys
100%
A Job in the Theatre Chapter 14
Sarah and Paula shared at drink as they tried to decide what to wear for their date. "Every good outfit starts with lingerie. What do you think of these?" Paula asked holding up a pair of baby blue panties. "Nice. But I really think these will be better" Sarah said holding up ... Read full Story
shemale lover 2012-03-14 2,466 sucking shemale kissing
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 4,194 Stockings anal sex Group Sex Blowjob
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 4,174 transformation oral sex cum swallowing
100%
Beefy Buns
It's hard to get good help. Probably, that's true in any business, but it's especially difficult to find decent employees in the fast food racket. Believe me; I've tried. I manage the local Beefy Buns franchise--burgers, fries, and shakes is our mainstay, but the menu also features fish and chick... Read full Story
shemale lover 2012-04-22 5,831 anal sex Creampie blonde shemale
100%
Darling Nikki
Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She ... Read full Story
shemale lover 2012-07-15 7,159 Cumshot oral sex Latex sissy
100%
A Turkish Delight Part 2
As I sat in my hotel room I pondered my future and what may lie ahead. My passport had been seized and I was not able to leave Turkey nor could I tell anyone about my plight. It was late afternoon when a courier arrived at my hotel with a large white box. He rang the bell and upon answering I was gr... Read full Story
shemale lover 2012-07-16 2,535 anal Creampie Fetish domination crossdressing
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 10,304 shemales Cumshot domination oral sex
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 3,433 jerking oral sex sissy
100%
Sabbatical or Continuous Gang Bang?
My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My... Read full Story
shemale lover 2012-08-28 5,371 Crossdresser Cumshot Fetish Blowjob gangbang
40%
Kitten: A Pantyboy StoryKitten: A Pantyboy Story
It's easy now to look back and play armchair psychiatrist and see where my fetish for school uniforms and cute cotton panties started, but it wasn't until I met MISTRESS that I realized exactly how deep that fetish was ingrained in my mind and soul. Mistress knew I was a pantyboy after the first ... Read full Story
shemale lover 2012-09-10 6,857 Crossdresser fingering Sex Toys handjob 69
100%
My bitch
Her fingers touched mine as she removed my empty, soup bowl. Her skin was soft, warm to the touch, almost hot. I looked up, but she had already turned and was heading to the kitchen. That was the second time she had touched me. After appetizers, she had reached around my shoulder to slide away ... Read full Story
gag9gag 2012-10-13 3,672 first time Big Cock facial
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 6,066 sucking oral sex facefucking
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 3,055 Stockings sucking Sex Toys crossdressing heels
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 7,736 anal Crossdresser Blowjob domination ass fingering
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 16,962 Crossdresser sucking Big Cock ass licking big boobs
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 30,972 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 32,411 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
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 5,598 Crossdresser domination Guy Fucks Shemale cum in mouth PRISON FUCKBOY PRISON PUNK prisoner Prison Bitch
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 5,140 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
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 4,521 taboo femdom crossdressing
50%
A Night On The Town
The third Friday of every month is my day. This is the one day, or rather night of the month that I truly look forward to. Only twelve times a year, do I allow myself to totally, absolutely indulge myself. To be a slut! A total tramp! To luxuriate, and fulfill my desires that have been pent up insid... Read full Story
shemale lover 2012-02-06 2,620 Fetish nylons shaving
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 4,020 bdsm domination transvestite
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 7,764 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
71%
Xdressing school fucked by black teacher
This is a kinky sexual fantasy about my university teacher .Well it all started the first day my new teacher walked in the door .Six foot, very good looking black man .He was 15 years older than me very smooth with the girls.I just turned 21 and am three years into my transformation from male to fem... Read full Story
shemale lover 2012-08-16 4,030 anal sex cum swallowing black cock teacher
100%
Don/Dawn of the Dead
I did all of the 'normal' things first. Checked all the doors, checked all the stores, closets, back hallways, stockrooms and bathrooms for zombies. Made sure everything was sealed off. Established a base inside the mall to operate from. Made an escape plan. Hid some of my guns and ammo in a cache w... Read full Story
shemale lover 2012-10-25 3,410 first time oral jizz
100%
Angel Chapter 1
On her eighteenth birthday, fresh from her shower, Angel Jones looked at her nude reflection in the full-length mirror in her bedroom, and was mostly pleased with what she saw. Her blonde hair, down past her shoulders and still growing, was soft and shiny, and all that she could have asked for. She ... Read full Story
shemale lover 2012-11-30 5,877 wanking feminization climax
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 5,489 Crossdresser domination PRISON PUNK prison sex Prison Bitch
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,515 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
100%
The Biology of Music - I fucked my trans substitute teacher
I was never strong in school. I wasn't very interested in what we were being taught, and the teachers liked me enough to not give me too hard a time about it. I attended an all boys school. It was actually quite a religious school which makes this story all the more surprising. I was in the middle c... Read full Story
terrifictim 2022-01-03 3,574 Creampie Guy Fucks Shemale feet licking first time with a tranny teacher student
82%
Tranny Gas Station Attendant
This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intima... Read full Story
shemale lover 2014-06-29 7,632 Stockings shemale cumming
77%
Kayla and Tracy
Awoken by the sunlight, Kayla rubbed the sleep out of her eyes, then vaguely gazed at the city scene outside of her panoramic windows. Realizing that if was a bit cold to her left, she glanced over in that direction to confirm what she thought. “Damn, I must have slept a bit late,” sh... Read full Story
shemale lover 2017-11-02 10,011 sucking pussy big ass
100%
Sudden Shemale
I woke up from the anaesthetic, still very groggy and uncertain. I couldn't remember anything, and my head and body ached terribly. I glanced around, trying to lift my head off the pillow, but it just didn't work. After a few minutes, I tried again, and this time I managed to stand up. I was ... Read full Story
shemale lover 2011-08-30 5,537 asshole pussy Big Cock
100%
The Perversion of Bev - Part 1: The Beginning
“Some fucking romantic weekend this is turning out to be” thought Bev as she sat alone in the hotel room. Phil had told her he’d booked something special to celebrate their Silver Wedding anniversary and she’d been so looking forward to a weekend away without the kids. The fi... Read full Story
shemale lover 2011-10-11 4,327 anal first time shemales