Sort by
Relevancy

Free Stories

60%
Amy's Surprise 2: Enter Karissa
What did you think? Amy asked. Well, let's see, I started to answer, You gave me the best blowjob I've ever gotten, sucking your dick was about the best thing ever, and sharing your cum with you was incredible.all in all, I'd say it went well. Amy smiled and walked over to sit with me on the couc... Read full Story
shemale lover 2012-05-08 4,774 anal sex shemale Sex Toys
60%
A Revenge Fuck Part 3
Chase gripped my ass-cheeks and plied them apart, shoving his cock up, balls deep into me. My legs, stuck up into the air and folded back, my knees bouncing there even with my head as he fucked me there in his car. We faced each other, panting and kissing, hot breath and saliva mixing. His ruddy coc... Read full Story
shemale lover 2012-06-03 4,166 anal Cumshot shemale oral
80%
Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
shemale lover 2012-06-24 5,658 big dick tranny anal sex Cumshot orgy facial oral sex
100%
Caught by the Past Chapter 2
Previously - After a drink with a new friend he invites you back to his house. Strangely drawn to this handsome guy he persuades you to dress in girls clothes... Now You're wearing a sexy leather mini skirt, fishnets and high heels, your cocks like rock and you're just about to show yourself... A... Read full Story
shemale lover 2012-06-28 3,034 Fetish cum Lingerie oral sex crossdressing heels
100%
Dean and the Tgirl
"Hi, it's Kelly," the sexy transgendered girl cooed when Dean picked up his hotel room phone. "Just get in?" Dean asked. "How was the drive." "It was quick -- I made good time." "Bet your thirsty," Dean said. "Meet me in the lounge down... Read full Story
shemale lover 2012-08-05 4,314 tranny anal sex cum oral sex
100%
Your Best Damn Girlfriend Ever
There are times in a young man's life when it is so full of fun and sex that it's a wonder they survive. College is one of those times for many young men and it certainly was for me. I attended a small private collage in southwestern Ohio at a time when the world seemed to be totally focused on it's... Read full Story
shemale lover 2012-08-11 12,816 anal sex Cumshot shemale oral sex
100%
Brad and Tina
It started a year ago; I would get on the AOL chat rooms in hopes of meeting local dominant men. I was seeing a guy named Dan from time to time, just a fuck, nothing serious. Mistress Olivia was an incredible woman and the Domme I was currently serving. She satisfied most of my cravings to be ... Read full Story
shemale lover 2012-08-20 2,583 Cumshot sucking orgasm cum swallowing
80%
Brazilian Discovery Chapter 4
John, the husband of Susan (see Susan and John series) has travelled to Brazil for a one year training session. Mr Gupta has sent him as the pretty little Joan, in the hope he would lose any interest for Susan and leave him totally free to deal with his senior accountant! The corset maker had bee... Read full Story
shemale lover 2012-08-25 4,345 cum oral huge cock brazilian
100%
Porshe's Escapade Chapter 1
Hi, it's Porsche back again and rather disappointed. I thought I would get a much better response to my first story "Interactive Crossdresser...Dare Me" but i didn't. I was kind of reluctant to put myself out there since i have never dressed in public or in front of anyone else but my Aust... Read full Story
shemale lover 2012-09-03 2,078 Cumshot Blowjob Big Cock cum swallowing
100%
V Is for Vicky
"Mike, it's getting late. You really ought to go and fetch Martina." That was my wife Mary talking. We'd sat up until almost one in the morning waiting for Martina to get back from the party. At first I was reluctant, I mean, Martina was nearly eighteen and really we should be standing ... Read full Story
shemale lover 2012-09-07 4,060 Cumshot Blowjob Big Cock heels
100%
Transsexual Sisters Chapter 6
Part 6: A Party to Remember MICHELLE AND NICOLE MAKE A CAREER CHOICE After their tormentors were jailed, Michelle and Nicole felt relieved and happy for the first time in weeks. Whether from curiosity, respect or sympathy for their ordeal they became very popular around the USC campus. They we... Read full Story
shemale lover 2012-09-08 4,347 Cumshot sucking threesome Shemale and Girl deep throat
66%
Alabama Nan: BBW Time
I wanted Betty to know what true pleasure was. To know that "big" girls like us deserve to enjoy another person sexually. She gingerly followed me into my apartment as I turned on the lights. I knew Betty had no idea what was about to happen, but even though I kept telling her I wasn't you... Read full Story
shemale lover 2012-09-20 3,779 shemale cum fingering oral sex
85%
Busted and Hoodwinked
INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack a... Read full Story
shemale lover 2012-09-30 6,202 anal Cumshot Ladyboy oral
100%
Working for a Living Chapter 4
The buzzing of her cellphone on vibrate was barely noticeable over the hum of the vibrator between her thighs. Normally Jamie would have just ignored it but Chris had told her he might call if his meeting finished early. Her hand felt for the phone on the nightstand beside the bed. She looked at the... Read full Story
shemale lover 2012-10-05 3,036 anal shemale oral cum swallowing
50%
Gangbang: Daddy's Girl
"Oh yeah...that's daddy's girl," my dad moaned as he massaged my enormous round sticky ass. I'm 18 and my sister was about 5 years older than me, so who knew how long this had been going on for, I thought to myself. At least I tried to think as I slowly closed my eyes and bit my bottom ... Read full Story
shemale lover 2012-12-16 9,622 sucking cum gangbang
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 4,598 taboo Cumshot shemale Mature
97%
How I Met Alyssa
I groaned as the sun was shining onto my face. I turned around so I could get some more sleep, but I saw it was 9:22 am and I decided it was time to get up. I got out of bed and went to the bathroom of my little apartment to freshen up a bit. I looked at myself in the mirror and saw a 20 year o... Read full Story
shemale lover 2013-02-12 14,450 hardcore sucking Big Cock ass fucking big boobs
81%
My stepmother has a surprise for me
My name is Robert, I'm 18, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men on the videos, that turned me... Read full Story
shemale lover 2013-04-08 236,136 suck Big Cock jerking big boobs cum swallowing
100%
Bad Habits CD Fantasy
Why did I keep making bets like that, was the only thing I could think of while in line. Why did I keep making bets I was destined to loose, and then have outcomes like...well, this. I was standing in line to go to a cosplay convention, and was in full costume, but of the wrong gender. I was dressed... Read full Story
shemale lover 2014-07-21 4,002 suck Big Cock Lingerie oral sex cd
87%
Why you should never cam
* Sorry for the poor writing but since it is the summer and I am taking sometime off to reflect before starting school next year I thought I would write up about what had happened to me the summer before. It is currently a work in progress and if spot any spelling mistakes or errors feel free to cor... Read full Story
jennychen 2014-09-02 5,495 cock shemale Big Cock Asian
88%
Tgirl trained to be the town whore to serve ALL Black men
A few years back I spent time on and off with several shall we say more dominating types of gentlemen One of them, who for this I shall call Leroy, just loved when we got together to make me totally helpless. It was our 6th or 7th meeting. Leroy and i had been chatting on Yahoo and when he f... Read full Story
__tiffanylondontv__ 2014-09-30 6,306 suck shemale ass fucking Interracial big cocks
94%
Renting out a room
When my wife suggested that we rent out the guest rooms above the garage to a college student it sounded like a good idea. It was very much like a small apartment, with a bedroom, bathroom, and small living room. No kitchen of course, but we could share ours and it seemed like a good way to make a l... Read full Story
Alic91lovesporn 2015-07-29 21,715 suck shemale jerking orgasm domination
100%
How it all began...
It all started about 10 years ago, coming home after a night out in the town and feeling horny... My shoe's left in a heap by the door and a trail of kebab meat leading up to my bedroom, I knew that my happy wank time was about to commence. As soon as I got in my room my jacket was flung ont... Read full Story
Trans Delights 2015-11-16 4,567 sucking shemale cumming wanking pre-cum
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 6,594 blonde shemale submissive cocksucking
87%
My way to shemale sex
It all started with porn. 10 years ago, i was watching porn on my bed, jerking off watching a girl sucking a big cock. I looked at my cock and started wondering what that beautiful peace of meat tasted like. After a few moments of hesitation, my curiosity took over and i put my back against the wall... Read full Story
andre_xp_8 2018-07-24 13,997 anal Blowjob shemale first time
92%
Dani & Paulie - 2
Devon, it turned out, was a complete gentleman. The accent i couldn’t place was a hybred of south London in the UK and the Caribbean. He’d been in the states for a few years after being spotted as a student, modelling for some extra cash. He’d greeted me on the veranda like an old friend, a hug an... Read full Story
SissyDani31 2018-10-09 3,673 Crossdresser Big Cock Interracial
100%
Dressing and driving
A little about me, I'm married, and wife doesn't have a clue I like to dress up. I would love to have her know and accept it, but I don't think she would. I do cam and love to get instructions from people that are watching on cam. Am I a sub? I think I am. I like to drive dressed. When I take a driv... Read full Story
SandyCrossdresser 2018-11-26 5,883 Amateur Outdoor crossdressing driving Reast area
100%
Swallowing My First Shemale
Nitromethane It's been a couple of years now that I've been intrigued by shemales, and though I've met up with a few I've met online, I've still not gone any further than some stroking or letting them blow me. I'm not sure what my hangup is, since I can't seem to stop watching these gorgeous gir... Read full Story
Gwapo67 2022-01-18 4,177 Latina cum in mouth
100%
MILF Alessia Travestita finds a bottom boy pt 2
Several days ago, Alessia a beautiful Transsexual with a huge cock seduced Stan on their cruise ship. He willingly and enthusiastically sucked her cock and gave her his ass. She brutally throat fucked his mouth before pounding his ass. They spent over two hours together until they were interrupted b... Read full Story
darrell 2023-08-13 6,473 anal Shemale Fucks Guy Fetish Blowjob blonde Big Cock domination Mature deep throat cum in mouth sandals toe sucking
100%
A true first time.
I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... Read full Story
Gtaaddict3 2023-11-21 9,514 first time cock suck Blowjob shemale Big Cock trans oral fantasy virgin escort big first time
100%
My Girl Friend and A Shemale
I walk up to the door of my girlfriend’s apartment. As I start to slide the key into the lock, I can hear slight muffled noises from inside. As the door slowly opens, I am met by the sight of my girlfriend laying with her legs spread wide open on the couch and her super sexy friend Shayla, w... Read full Story
tgirlloverme 2011-09-07 7,846 threesome shemale oral
100%
Little cock convention
They came from all over the nation to downtown LA convention center. It was the "Little Cock Convention" I watched as men from all races and status came in. Sometimes they came with their wives,friends,Mistresses,lovers, or even their boyfriends. I was on Guard duty and walking the conven... Read full Story
shemale lover 2014-07-07 7,327 shemales hardcore sex humor
100%
My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts :) I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use the ... Read full Story
shemale lover 2014-08-25 9,631 sucking shemale teasing
90%
My shemale bride
I've been dating a beautiful girl for about a year, her name's Sasha, she's got long dark hair, beautiful blue eyes, slim very sexy body, perfect, my little angel, and we get on great, so much so we decide to marry, only one problem, she won't let me in her knickers, but this make me respect her eve... Read full Story
shemale lover 2015-06-01 15,555 anal cum domination
79%
Black Shemale Tube
It was truly a unique experience. One day I was very bored, and I was browsing through the Black Shemale Tube, and that's where I have found her. Sheila was a stunning Black girl, very tall and skinny! She had a killer body, the cutest little butt and small, firm titties. Since the moment we met thr... Read full Story
shemale lover 2015-11-29 25,138 shemale oral sex stiff cock
100%
Buffy the Shemale Vampire Slayer Part 3
Buffy couldn't stop smiling. It felt great to have left Spike on his knees, clutching his balls in pain after she'd sucked his cock and swallowed his load of icy vampire's semen. Sex was about power, not love, and nothing made a girl feel more powerful than reducing a man-or, in Spike's case, a u... Read full Story
shemale lover 2011-08-19 6,208 hardcore celebrities shemale
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 4,621 shemale orgasm pussy licking
100%
Cuba
A trendy upscale bar in La Jolla on a warm Friday night was not what I had planned. It's not usually my crowd, but a friend asked me to join him and I didn't really have any plans for the evening. What the hell I figured, I might even meet someone interesting. It's a warm summer evening with a li... Read full Story
shemale lover 2011-10-24 3,643 Stockings Cumshot oral
95%
My Girlfriend's Mother Has a Secret
A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-). Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pr... Read full Story
shemale lover 2011-10-30 34,209 anal shemale oral
100%
The Scenic Route
Ahead, the desert highway was flooded. But for Rose's own car, a cherry red 2008 Ford Mustang, the route had been empty for the past half hour. It was no surprise that the road had been nicknamed "The Loneliest Highway in America." The loneliness was fine with Rose, though. In fact, she pr... Read full Story
shemale lover 2011-10-31 3,637 blonde shemale
80%
Boy Meets Girl
"What's her sister look like?" Dave Newell asked his brother. "You've seen Steph. They're sisters." Stephanie Johnson was a hottie, no doubt about that, Dave thought. Still, that didn't necessarily mean that her sister would be a looker. If Stephanie were from Venus, her si... Read full Story
shemale lover 2011-11-05 5,488 asshole oral sex tgirl
95%
Losing My Virginity... Sort Of
Tonight was going to be the night. In just a few hours, I would no longer be a virgin. The route my girlfriend and I had taken to get there, however, had been somewhat strange. Lets start a while back. Her name is Kelly, and she's a beautiful girl. 5 foot 3, roughly 100 pounds. Her tits and ass a... Read full Story
shemale lover 2011-11-12 6,169 anal sex shemale Big Cock
50%
Going Up Part 2
Charlie's cock was as perfect as if it had been sculpted by a consummate artist. The rigid column of flesh rose from the dense thicket of his pubic hair and, lined with blue veins and topped by a once-pink gumdrop-glans that had ripened to a deep purple, looked as inviting as an exotic fruit. The eg... Read full Story
shemale lover 2012-01-01 3,138 Cumshot shemale ass fucking
100%
Tilted Kilt Chapter 3
Girls Only Party I drove down to my sister Katie's house in Carlsbad on Saturday morning to spend the weekend with her and her girlfriend Brandi. I live in North Orange County so it was only an hour drive. She's 25 and I'm 24 so we grew up together and were always friends. We shared our lives and... Read full Story
shemale lover 2012-01-25 3,263 Cumshot sucking Big Cock
60%
A Trans-Lesbian Montreal Love Affair!
St. Catherine’s Street in downtown Montreal is one of the world’s most vibrant streets and entertainment corridors. Known for its energetic, exciting and often crowded venues, it is lined with quality restaurants, theatres and many popular nightclub establishments. St. Catherine’s ... Read full Story
shemale lover 2012-02-12 5,242 Big Cock oral orgasm lesbian
100%
A Job in the Theatre Chapter 16
"Ted has invited me to his poker game" Paula let slip. "Oh really? Now that sounds interesting" Sarah said. "It will be if we come up with the right uniform. It's all boys so I am going to dress in some sort of domestic help type uniform. But of course it has to be the... Read full Story
shemale lover 2012-03-15 3,426 shemales anal sex Big Cock
100%
Emily and Steve Part 6
Emily and I lay in the sun of the hilltop clearing, occasionally speaking but mostly sitting in a very contented silence. The sun was high in the sky, and soon had dried the cum that had I spewed out across my stomach and chest. Other than the rustle of leaves, a few bird songs and an few whinnies a... Read full Story
shemale lover 2012-04-07 2,529 voyeur cum oral sex deepthroating
100%
My Lesbian Shemale Adventure
I had worked a day shift - I got off at about 5 and wanted to go do something. My two buddies, Niles and Will, were there and they asked me if I had ever been to this little bar in the same strip mall as the club I worked in. I hadn't. It looked dingy and dark from the outside, and since I didn't dr... Read full Story
shemale lover 2012-05-01 3,017 big dick Cumshot Masturbation small breasts
75%
The Succubus with a Cock
His cock felt so good between my lips. I savored every inch with such great passion he moaned and fucked my head farther down his shaft. I gagged many times but I was getting better at deepthroating. His balls were coated with my saliva, and soon the couch we were sitting on became wet to. I really ... Read full Story
shemale lover 2012-05-18 8,219 hardcore anal sex Cumshot cum swallowing
71%
The Superbowl
I was very surprised when my brother-in-law Tom invited me to watch the super bowl with some of his friends. The only reason he would “invite” me over was to be his little sex sissy, since he had enough pictures of me dressed as a girl sucking and being fucked by him I had no choice but ... Read full Story
shemale lover 2012-05-23 3,591 Stockings anal sex Cumshot Fetish deepthroating sissy
90%
Professor to Sissy Slut
I had just turned thirty-four and I was miserable. My wife of twelve years had left me for another man and was living with him. We were not yet in the process of filing for divorce and I was hoping she would have a change of heart. I was still in love with her but I understood why she had left. We h... Read full Story
shemale lover 2012-09-04 5,136 Stockings Cumshot Blowjob fingering ass licking
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 15,056 Cumshot Masturbation Blowjob ass licking redhead
66%
An Ass to Die For
It's a very strange thing. We all have our personal quirks. The things that make us unique and stand out from the crowd. I've just never met anyone besides me who has mine before, and to tell you the truth I'm not sure if it's a gift or a curse. You see, I have a girl's ass and not just any old girl... Read full Story
shemale lover 2012-11-13 4,276 big dick sucking porn
100%
Dream Lovers
Chapter 01 (edited) An Accidental meeting Doctor Matt Dillon treated scores of accident victims coming thru the Emergency Room. Cool under pressure, quick and aggressive, his record of successful treatment is impressive. His natural caring heart constantly battled the cool detachment necessary... Read full Story
shemale lover 2012-11-15 3,514 shemale oral orgasm
88%
Who's the Bitch Now?
Well I was approaching the big Three-O in a couple months and dreading it. I am still in decent shape but the genetic roulette wheel has been a bit unkind since I have been loosing my hair since my early twenties but shave my head so it doesn't look bad. On the other hand I have a good job even d... Read full Story
shemale lover 2012-11-15 5,877 shemale oral huge cock
66%
Angel's Interludes Part 2
Here are more of Angel's hot little interludes. Just unencumbered hot sex for your cold lonely nights. A Restaurant Interlude Angel and Bobby were sitting in a rather dark corner booth of a quiet little Italian restaurant. This was their second date and so far Angel liked him. He seemed willin... Read full Story
shemale lover 2012-12-08 3,328 Cumshot sucking shemale