Sort by
Relevancy

Free Stories

95%
T-Girl University
Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for ... Read full Story
shemale lover 2012-09-05 14,540 Cumshot Masturbation Blowjob ass licking redhead
94%
My first incredible CD experience
Following my experience with Gloria I hooked up with some other shemales. The experiences were good, but nothing worth writing about...that is until I met Andrea. While on one of my typical business trips I visited a local drag club a few towns over. It was a very clean place and since it was a Frid... Read full Story
Joe Francis 2018-06-18 9,097 Crossdresser Amateur Blowjob redhead cum in mouth
100%
Meeting Amanda
I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... Read full Story
rforasht 2022-07-20 7,005 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
80%
Buffy the Shemale Vampire Slayer Part 14
"Let's get this over with," Buffy suggested. "The sooner we start, the sooner I kick your demon ass." Baphomet smiled. "You will fuck the witch," he said, "while I fuck you." Buffy shook her head. "Willow's my best friend. I can't-" "Th... Read full Story
shemale lover 2011-08-23 4,784 anal sex asshole Big Cock
66%
Buffy the Shemale Vampire Slayer Part 4
Damn! Wherever Willow was, she wasn't home. The witch still hadn't returned to her motel room. At least, this time, Buffy hadn't had to rely on Sunnydale's public transportation system. Xander had given her a ride across town. He'd offered to wait, to make sure that Willow was back, but Buffy, wa... Read full Story
shemale lover 2011-08-19 3,583 shemale orgasm nipples
100%
Pay the Genie Part 2
Scott leaned back on his couch and enjoyed the magical efforts of his new best friend, Ura the ebon genie goddess. His jaw ached slightly from paying for the oral loving he was then receiving, but as always it was worth it. It had been a few days since he found the magical pocketwatch that contained... Read full Story
shemale lover 2011-10-12 3,448 asshole shemale oral sex
50%
The Making of A Sissy Part 10
Bella quickly gulped down her vodka and cherry, her bottom tingling with anticipation as her new mature friend gave her a commanding look; she had so enjoyed being submissive for her at the end of a leash, and now she knew she would be bound tightly on a soft inviting bed, and made completely helple... Read full Story
shemale lover 2012-05-29 4,232 dildo oral sex Sex Toys sissy
100%
The Making of A Sissy Part 9
As they sat sipping drinks and discussing what shots would be done indoors or out; Bella’s little cock bulged in her sari as the mature redhead licked her lips as she discussed the ways in which Bella should be trussed, collared and leashed, amongst other things. Sandy stood up suddenly and ra... Read full Story
shemale lover 2012-05-28 3,061 shemales Fetish bdsm sissy
100%
Birthday Present
Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all about the exchange and nothing else was said about my birthday. The day arrive... Read full Story
shemale lover 2012-06-16 13,856 Cumshot Fetish orgasm oral sex
71%
Birthday Present Part 1
Birthday Present or (I've Looked at Love from Both Sides Now) Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all abo... Read full Story
shemale lover 2013-01-18 11,023 hardcore sucking Blowjob Lingerie ass fucking
100%
Buffy the Shemale Vampire Slayer Part 15
The Slayer looked at the witch's ass. It was beautiful, she thought. Round and smooth and creamy white, each buttock seemed a half moon. Willow's impaled anus showed within the deep cleavage between the silken globes, its rim riding the stiff cylinder of Buffy's cock as she plunged it into the witch... Read full Story
shemale lover 2011-08-23 4,181 anal asshole shemale
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 13,605 first time sucking fuck domination
92%
Thank you for Paradise
This hot shemale story was sent to me by our forum member Leeya and i'm anxious to share it here with everybody. It's a classy story about a guy who went to an Asian country on a business trip and met a very beautiful womain in a very romantic atmosphere... Little did he know that this young voluptu... Read full Story
shemale lover 2015-03-13 6,166 anal Asian Ladyboy
100%
Buffy the Shemale Vampire Slayer Part 5
By the time that Buffy arrived at Rupert Giles' apartment, the former librarian, her ex-Watcher, had just finished reading a new volume of what Edgar Allan Poe, in The Raven, had referred to as a "curious and quaint volume of forgotten lore." He'd just settled the large, leather-bound volu... Read full Story
shemale lover 2011-08-19 3,410 hardcore celebrities shemale
83%
Buffy the Shemale Vampire Slayer Part 6
Buffy arrived in the demon dimension on her elbows and knees, just as she'd been when her mentor, Rupert Giles, had been butt fucking her a moment before the spell they'd cast transported her from his apartment to this bizarre land of the damned. Her legs were still spread wide apart, and ass was st... Read full Story
shemale lover 2011-08-19 4,043 asshole shemale Big Cock
100%
Buffy the Shemale Vampire Slayer Part 8
Another torrent of semen rushed through the cavernous vagina, sweeping Buffy before its irresistible force. Again, she felt millions of fresh sperm wriggling over her bare flesh, thrashing their whip-like flagella against her erect nipples, puffy areolas, pert breasts, concave tummy, downy pubes, st... Read full Story
shemale lover 2011-08-21 3,436 tranny pussy
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 5,096 Cumshot cum swallowing handjob
50%
Cincinnati Apocalypse Part 2
This time, however, his fight against the Cincinnati Hellmouth was more personal. This time, it wasn't about loyalty; it wasn't about saving the world. It was about vengeance. It was about Anya. Although Xander hadn't seen Anya's death himself, Andrew Wells, who'd been with her at the time she'd ... Read full Story
shemale lover 2011-11-22 2,561 hardcore celebrities transsexual
100%
Enchantment of the Shadow Realm
It was a enchanting night. The moon was full. The street light reveled an other worldly stream of fog through what I could see of the dark forest. Unfortunately I was having a hard time appreciating all this beauty. I was stranded. I had missed the bus and had no way of getting back to my hotel. I h... Read full Story
shemale lover 2012-04-14 3,773 Group Sex Cumshot Big Cock facefucking
100%
Pounded to submission part2
Two days ago Joesph was checking out porn. A couple of BBW vids here some interracial there, the usual. Then he saw a just viewed picture with a Brazilian She-male and couldn't stop looking. With his curiosity getting the better of him he clicked on it. She was gorgeous! Her face appeared to be as f... Read full Story
shemale lover 2013-04-21 7,669 Cumshot suck shemale oral deep throat
92%
The Curse (Sissy Story) by sdvine
I wasn't really having a good time that night at the bar. Truth be told, I had been practically dragged out in the first place by my best friend Joe, who told me he was tired of me "sitting on (my) ass" every night "finding new ways to be boring." Quite frankly, if this is what qualified as being no... Read full Story
shemale lover 2015-02-27 6,665 ass Cumshot sucking cd sissy
66%
Castro - goddess of love (starter)
Nobody would have believed the scene was true, slender, smooth and tanned legs crossed is such a such deliberately provocative way as to reveal a glimpse of sharp white panties. A tightly fitting, classically styled little black dress cut to ensure firm large breasts were displayed to maximum effect... Read full Story
Law12 2018-03-02 1,763 tiny cock Supernatural
100%
Castro - shemale goddes
Nobody would have believed the scene was true, her slender, smooth and tanned legs crossed in such a deliberately provocative way as to reveal a glimpse of crisp white panties. Her tightly fitting, classically styled little black dress cut to ensure firm large breasts were displayed to maximum effec... Read full Story
Law12 2018-03-04 4,817 Masturbation Bareback Creampie Ass to Mouth cum in mouth Supernatural
57%
Next friday,next payment (I hope)
Update - monday march 19,2019 : strange - almost supernatural - thing happened when I was walking to a place where I used to suck, my lips start moving to the right side like to suck something,their movement was kinda "out of control", once I stopped walking I heared steps behind me,that was a ma... Read full Story
Najeeah 2019-03-20 3,278 Crossdresser Amateur Outdoor Creampie Blowjob Big Cock swallow cum
80%
Transsexual Savage
John had walked for eleven days. He was headed towards Fort Winston at the Hiat River, and he still had about three days ahead of him. The Hiat River was the natural border that separated the civilized world, where he came from, and the savage and brutal wilderness, where the natives lived and pract... Read full Story
Anal Orgasm 2020-07-10 5,995 Big Tits Outdoor Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Guy Fucks Shemale
50%
Giving Away Virginia Holton
Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... Read full Story
shemale lover 2011-10-08 4,358 shemale cum ass fucking
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 6,908 fuck oral
100%
Best trip to the mountains
I was driving out to the hills for some solo camping. I was alone since all of my friends had quit on me at the last minute, but i figured i'd just enjoy nature while i had the chance. I was almost through with the four hour drive, and noticed fewer and fewer cars as i got closer to the site. Onc... Read full Story
shemale lover 2012-03-04 3,691 anal shemales Group Sex oral
80%
Career Shift
Receptions are not my favourite things in the world to attend. I don't mingle and 'rub elbows' like agents and sales people do. I usually end up at the bar drinking alone, looking at all the phoney people. I am a writer, a sports column writer more specifically. The magazine that I write for is one ... Read full Story
shemale lover 2012-03-06 5,497 Group Sex Blowjob fingering orgasms
100%
The Invitation
"You see, we have to come up with something that would be so embarrassing for you that there is no way that you would ever show those pictures of me to anyone, regardless of how d***k you got, or how horny you got or how pissed off at me you were,” Sally went on. “Something that wou... Read full Story
shemale lover 2012-03-20 5,804 Group Sex crossdressing feminization
90%
My Pet
I went into the pet store very excited. I was really going to do this! I walked up to the girl behind the counter. She was pretty and looked very young to be working in a place like this. Hi. I'm interested in the pets in the back. Oh? What kind of pet were you looking for? The kind that... Read full Story
shemale lover 2012-05-02 4,993 big dick Cumshot Blowjob fingering jerking off
100%
Awakened by Candy
It was a Saturday and I was just strolling down the High Street, going nowhere in particular, when I noticed a commotion down a side alley. A largish male was pushing two girls around; they both looked pretty distressed. I grabbed the bloke as he slammed one of the girls into a door, and he went ars... Read full Story
shemale lover 2012-05-19 3,088 anal sex Cumshot Masturbation fingering ass licking
83%
The Making of A Sissy Part 12
Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as... Read full Story
shemale lover 2012-05-31 4,117 anal Fetish little cock sissy
50%
For The Sensual
For the sensual, description is everything. The collar. The collar is custom-made; one of two; her request. This particular one matches the corset. The corset—the "bustier." The collar. Literally, no choker here. She is disciplined. Her collars merely evoke ownership. She belongs. Sh... Read full Story
shemale lover 2012-11-14 3,006 anal kissing facefucking
93%
A discovery
The booze and caffiene had turned from a warm buzz into a slightly annoying headache in Miles' psyche. He watched as his live-in girlfriend Mary danced and ground against a tall blonde that could have been her younger sister. Club Inferno was at the point of orgasmic rush when the standing room o... Read full Story
shemale lover 2014-08-15 4,922 licking shemale pounding
85%
Unforgettable First Time
I am in my late thirties and have known for a while that I have a sexy body. I'm 5'11", slim and athletic with little cherry butt and shapely legs. A lot of women have told me my body is sexy. A few men have mentioned it too. Sometimes I get photo-snapped at the pool or the beach. I've been luc... Read full Story
shemale lover 2016-05-06 9,895 cum oral deepthroating
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 3,515 Masturbation pussy shemale
100%
Modified Covers
As a hobby, some artists enjoy modifying vintage magazine covers so that their original topics are transformed into transgender themes and shemale models replace the female faces and figures that originally graced the periodicals' covers. In the process, the titles of the magazines are sometimes cha... Read full Story
shemale lover 2011-09-09 3,115 transsexual transvestite transwomen
100%
Transgender Encounter
I was at the Mall in Torrance, CA looking for a new pair of pants. There was this lovely young woman named Sherry working there, who was very solicitous, helping me find my size and select a pair of pants that weren't too out of style. I hate to shop, you see, so I usually wear a pair of jeans or sh... Read full Story
shemale lover 2011-09-19 3,562 suck cum swallowing nipples
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,438 Creampie Big Cock ass fucking
100%
Trans State Private School
Tommy heard a rumor that the Trans State cheer leading squad (even though it had the prettiest, sexiest girls in the state), all had cocks hidden in their cheerleader panties. His school was playing Trans State that day, and Tommy had to find out if it was true. The squad was on the fie... Read full Story
shemale lover 2012-01-04 5,062 shemales gangbang cheerleader
100%
A Discovery
But you see, even in his druken stupor, Miles was leaning against the south wall of the dance floor hoping.dreaming that Mary would coax the woman she danced with to come back to their apartment for a while. Club Inferno was the premiere goth/fetish club in Hollywood, and it was not uncommon for adv... Read full Story
shemale lover 2012-01-22 3,352 hardcore fucking transgender
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 7,939 Fetish transformation dildo
100%
A Discovery
The booze and caffiene had turned from a warm buzz into a slightly annoying headache in Miles' psyche. He watched as his live-in girlfriend Mary danced and ground against a tall blonde that could have been her younger sister. Club Inferno was at the point of orgasmic rush when the standing room only... Read full Story
shemale lover 2012-04-29 3,957 Cumshot shemale Big Cock oral sex
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 12,243 transgender
100%
The Making of A Sissy Part 11
Whilst Bella showered, Ellen and Sandy went down to the poolside to ready some ice and bottles for drinks later; there was Bella’s phone, Ellen tapped in the number to her own phone, and also took down someone else’s number. Ellen smiled wickedly. “I have a very sweet idea, but ... Read full Story
shemale lover 2012-05-31 2,576 anal Masturbation Fetish
100%
Duty Bound Part 2
The red stilettos, though new, were surprisingly comfortable as Hannah stepped out into the warm evening air; her cock bulged with excitement under her tight leather pencil skirt, her black silk top with chiffon sleeves capturing her sweet feminine shape perfectly. She met Simone and Babs at a bar c... Read full Story
shemale lover 2012-06-09 2,218 shemale heels erotic encounter
100%
Blame Abba Chapter 2
Part 4 Out alone I wanted something which would let me wear my black 4 inch leather stilettos with ankle straps, really sexy shoes, my very first pair of TV heels. I opened the wardrobe to get them out, then started choosing; black seamed stockings; a black thong; my waist cincher bustier; my sho... Read full Story
shemale lover 2012-07-17 4,173 Stockings Fetish crossdressing
100%
Office Casual
"Good morning Ms. Anderson," Karen said as her boss walked past her desk station and into her office. "Good morning Karen," Ms. Anderson said, not even stopping to make eye contact, "I'm going to be very busy today, so I'll need you to let me know if you get any mail fo... Read full Story
shemale lover 2012-08-30 3,616 brunette cock Masturbation Blowjob shemale big
66%
Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... Read full Story
shemale lover 2012-09-26 12,547 Group Sex Cumshot shemale oral
100%
Becoming Aphrodite
My wife and I have been married for 10 years. She is a beautiful brunette of 5'8" and 120 pounds. With her long hair and her cute and innocent face, she looks a lot like the porn star Cheyenne Silver. I would dare to say she's even prettier: her extraordinary green eyes are totally unforgettabl... Read full Story
shemale lover 2012-11-01 3,891 Group Sex cum oral sex cum swapping
78%
Anal Therapy
My new psychiatrist wasn't at all what I expected. When I saw her name in the phone book, I pictured a dowdy old lady wearing a long, gray skirt and flat-soled shoes. What else could Dr. Edith Doss look like? I got my answer when a tall, leggy redhead stepped into the waiting room. A tight, black... Read full Story
shemale lover 2012-11-24 7,473 anal Fetish cum crossdressing
58%
The dentist assistant
She was so desireable the first time I met her, I had to come back again. It all started when I changed dentist, and first met, shannon. So steamy, hot fire red hair, and green eyes, with that tight nurse skirt and white stockings, and opened toed high heels with hot pink finger and toe nail polish.... Read full Story
shemale lover 2013-07-17 4,902 Stockings Fetish oral sex doctor
88%
Very Impatient on a sex fanstay
Are you ready for this Mish?" "Not really but it's too late to back out now." I stood in a dark alley before a metal door shaking with both anxiety and the cold, waiting for the door slot to open and for the night to begin. I wouldn't admit it to my friend Simone but secretly I hoped we would ... Read full Story
ASSEaster5678 2018-07-10 10,460 Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale Mature
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 29,999 Teen (18+)
66%
Trannies in Space
There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... Read full Story
ASSEaster5678 2019-01-25 11,720 Shemale Fucks Guy Guy Fucks Shemale Sex Toys space robots