Sort by
Relevancy

Free Stories

93%
Ann Part 2
The next work day, that evening as I walk up to my townhouse, Ann is sitting on the porch and tells me, “Since you didn’t call I thought I’d come by, I was in the area anyway.” Even though I’d been with her the night before, I have to laugh and Ann asks, “So wh... Read full Story
shemale lover 2014-10-31 4,679 licking sucking swallowing
60%
Susan's First Time Part 4
The shadows of late afternoon crept across the city when Susan paid the cabbie off. Why had 'he' wanted her to come down to this neighborhood? She looked around with apprehension at the garish lights of bars and adult bookstores flashing in the growing darkness. One or two streetlights flickered on ... Read full Story
shemale lover 2011-10-14 2,992 Small Tits shemale massage
100%
Gender disfunction
Ginger and Steffi each took a chair in front of Dr. Winslow's desk and waited for her to speak. Looking up from a file, the doctor eyed the two girls for a moment, and then asked, "Which is which, I mean who's Steffi and who's Ginger?" Both girls mumbled their names, while Doctor Winslow w... Read full Story
shemale lover 2012-02-03 2,922 sucking cum swallowing
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 2,679 big dick Cumshot Masturbation small breasts
100%
Blame Abba Chapter 4
Part 10 Jeff again It was about half an hour before closing time that Saturday. Eric had just sent me off since we were very busy and I hadn't had a break since we opened. I sat in the back room, behind the bar, sipping on my lager. Then Jeff appeared, looking very sheepish, at the door. "... Read full Story
shemale lover 2012-07-18 2,424 Fetish crossdressing
100%
Afternoon Delight Chapter 2
The week was very busy getting ready for the party. All of Auntie's staff was invited, plus several students and professors that I didn't know. Well, this presented me with a small problem: Not all of them knew I was transsexual. I asked Auntie if I could wear a wrap skirt in order not to freak anyb... Read full Story
shemale lover 2012-08-26 2,510 Creampie Blowjob kissing cum swapping
100%
Porshe's Escapade Chapter 4
I received an email from Lisa a few days later. She again told me how gorgeous I was and how hard she came when Christie and her fucked me. She then wrote that Christie would be over the following Friday at 5pm to get me ready and then take me to the hotel for the bachelor party. I rushed home fr... Read full Story
shemale lover 2012-09-06 2,758 Crossdresser Big Tits Blowjob
50%
Tutoring Darla
"Professor ..." I glance up from my computer to see Darla, a sweet girl who unfortunately talks a mile a minute for far too many minutes at a time. I immediately wish her away—I'm too busy to pretend to listen to her prattle on today. Still, she means well enough and, anyway, I'm ... Read full Story
shemale lover 2012-09-08 3,693 Big Tits threesome ass licking domination
100%
Dream a Little Dream
I awoke to what I thought was an average day for me. Well average except for the fact that I woke up from one of the most sensual dreams I have had in my life. You know the kind don't you? The kind that makes you wonder if it was just a dream or real. The kind that makes you ache deep inside with lo... Read full Story
shemale lover 2012-11-12 3,406 cum oral sex swallowing
80%
First time
Ever since I was a teen I wanted to get fucked by a tranny. At 19 I finally got the opportunity when I moved to Leicester for university. I did a quick google search to find any in my local area. I stumbled across sexy TS from Colombia with 44DD and a 9 inch cock. My cock got extremely hard after se... Read full Story
tshirt1017 2015-10-08 8,156 first time tranny ass fucking mouth fuck anal virginity
78%
First Time Having Sex With A Shemale
Ok let's begin so I was walking down the street going to the store one day I saw a woman and her daughter moving into a house they had some heavy boxes that they need help with. At first I thought she was white girl but when I got closer to them they we're Asian becuase i only saw the back and they ... Read full Story
bigtranslover 2011-05-21 14,784 first time shemales interracial sex
93%
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 t... Read full Story
shemale lover 2015-01-19 6,126 blonde Big Cock Shemale and Girl
50%
Transgender Art: A Sampler
It's not often that transgender art offers viewers a glimpse of a female-to-male transsexual. Usually, the transformation is in the other direction, with the loss of the vagina in favor of male genitals and the acquisition of female breasts. However, one image does reverse this trend, showing a fema... Read full Story
shemale lover 2011-09-06 3,426 shemale transsexual transgender
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 3,502 sucking shemale stroking
100%
New 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 friends and after a nic... Read full Story
shemale lover 2011-10-05 2,713 anal sex Creampie orgasm oral sex
50%
Healthy Behavior
"Uhh…is Mr. Stanford around?" "One moment dear…ooh, damn heels. Makes it impossible to walk through doorways. Here I am ma'am. So, did the maid get you here alright? Hello? Earth to…" "I can't believe this…" "Oh, the heels? Yeah... Read full Story
shemale lover 2011-10-19 3,792 Big Tits transsexual oral
100%
First Time Dressed… at an Electronica Concert
I had been dressing as a girl to get off for some time now. For some reason there is nothing that turns me on more than a tight little cotton thong stretched across the bud of my asshole, holding my tiny little boy toy down where it should be. Over the years I’ve slipped into my mom and sister... Read full Story
shemale lover 2011-10-21 3,257 anal first time shemales Creampie fingering
75%
Surprise?
It was going to be a long day. Claire had never been much for the world of romance. Running from secret organizations and superpowered serial killers never left her much time for that kind of thing. She was always more pragmatic, trying to figure out how to survive or, when surviving wasn't an is... Read full Story
shemale lover 2011-10-27 3,139 anal asshole cum
50%
Plaid Pleasures - TG
Oh what a glorious time to be alive and horny. The miniskirt is back with a vengeance and the must-have item (for girls with the legs to show them off) was a short cute minikilt. I've never quite figured out why, but I've always found a tartan (or more commonly called plaid in the US) pleated ski... Read full Story
shemale lover 2011-11-05 2,940 sucking shemale cum
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 5,035 sucking Lingerie spanking
100%
Tgirl Fantasy Cum True
Before the gay man fantasies were the tranny ones. Looking back, I think I was drawn to them because they have the feminine bodies that I always loved mixed with cocks, the male body part that drove me crazy. 3 years ago I was jerking off to tranny porn online everyday. I loved the very hung t-girls... Read full Story
shemale lover 2011-12-07 3,694 first time shemales hardcore
100%
My Virgin Tale
It was a brutally cold winter night, even by Minnesota standards. It didn’t matter. I was just beginning my journey towards womanhood and needed to get out on the town for some much needed male attention. Technically, still in the closet, care was needed to make sure it went undiscovered anytime I s... Read full Story
Tawny Preston 2016-02-22 16,240 anal tranny sex Bareback ass fucking
100%
Leila's Secret
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 2012-02-10 3,029 first time hardcore fuck oral
80%
My Sex Change
It was the day I had been waiting for. My bags all packed, two years of saving and working hard and I could finally go on my round the world trip. I said goodbye to my friends and family and checked myself onto the plane. First stop; London. With my final waves and promises to return with present... Read full Story
shemale lover 2012-04-01 4,152 sex change jerking crossdressing
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 2012-04-01 2,748 first time orgasm fingering oral sex hermaphrodite
100%
The best of two Worlds
I just can’t help myself. The heat of Australian summer and the exposed bodies around me drive me crazy. It’s the hot wind playing with women’s skirts exposing their thighs and buttocks that make me loose my mind. I keep on looking down their blouses and up their skirts at every op... Read full Story
shemale lover 2012-04-25 3,042 facial jerking off huge breasts cum licking
100%
Burning Desire
Maia quickly hung up on Veronica and ran around, not knowing quite what to do. She ran to the oven and opened it, allowing a huge volume of smoke to escape. Her turkey was smoldering, obviously overdone. Coughing and blinded by the smoke, she ran to open the window. The alarm still sounded loudly. M... Read full Story
shemale lover 2012-05-07 2,453 Big Cock fingering oral sex small breasts cum swallowing
100%
Stephons first run in with Sora
I'm a young, attractive, slender, african american young man. I'm on my grind everyday. I like to drink, sleep, and fuck. I find that I can make any woman laugh until it is about that time to fuck. This is just one incident that proves this stament. Alright so I'm in one of my classes doing my re... Read full Story
shemale lover 2012-05-24 2,241 first time softcore t-girl
100%
Birthday Surprise
My girlfriend and I have the same fetishes and interests for the most part. We both find latex irresistible. We love the site of a tranny with a big cock. Robbie knew everything about me. For my birthday she went well out of her way to make me happy. The date rolled around. I figured it was jus... Read full Story
shemale lover 2012-06-19 3,919 tranny anal sex Cumshot Big Cock
0%
A Working Sissy Girl
I look up at my boots. Cute! Received delivery just day before yesterday, my boy friend hasn't even seen them yet. He'll like them, know he will. 3" spike heel ankle boots, very shiny patent leather, I look up at the one on my right foot. I run my hand down the thigh-high lace top seamed nylon ... Read full Story
shemale lover 2012-07-29 3,629 Cumshot oral sex sissy
50%
The Slave and the Sissy Part 5
Ella took the chain from their collars when they reported to her, together for the first time, in the morning. Pepper’s eyes were exceptionally bright this morning, and slave looked full of vigour and ready to carry out any command that befell him without the slightest hesitation. Pepper gripp... Read full Story
shemale lover 2012-08-13 3,605 anal sex little cock sissy
100%
Lesbian 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 2012-10-03 2,689 Cumshot Big Cock oral sex
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 4,003 taboo Cumshot shemale Mature
100%
Submissive sissy Jennifers first cock
There is a shy knock on your door. You open it, wondering who it can be. A stranger hands you the end of a dog chain, you can see that it leads to a red strap round his neck. "I'm Jennifer, Sir" he whispers, softly & huskily. It becomes clear now - you remember the conversation on the... Read full Story
shemale lover 2013-05-01 6,569 Stockings Blowjob fingering nipples
91%
My first tgirl Seduction, Damn Magnum
I decided to finally just go with my biggest fantasy for years, make love to a Ts. I Drive 18 wheelers across America and Im a very to myself kind of person. But at the sametime I can be that socual butterfly, standing 6 foot 5 having a tool 11 plus inches, I knew I needed special size condoms. Not ... Read full Story
Outkastinkz 2013-12-08 5,282 tranny Cumshot Big Cock ts dream
90%
Pretty panties in the toilets
Where I grew up in the North of England there wer many small villages with local toilets. Only much later in life did I realise how many sexy panty wearing dirty minded wonderful people are out there, I wish I had met more of them then, this is dedicated to all of them. When I was younger... Read full Story
jakuk 2016-05-04 4,245 suck panties wanking butt
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,034 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
66%
TO BE OR NOT TO BE – PART 5
TO BE OR NOT TO BE – PART 5 by Spanky de Bautumn Part 4. Sunny made a life changing decision and in the process becomes better acquainted with Mark. On Monday, I met Mel and Shari at the theater at ten to run lines. I was confident that I knew my part for the first act. My concern was with m... Read full Story
SpankydeBautumn 2021-02-24 2,039 Crossdresser Cumshot Masturbation Blowjob Big Cock Lingerie Interracial
66%
Can it get better than this?
I had to be in her area, so I set up another exceptional round with my TS ladyfriend on Friday. We smoked a joint (I usually don't) which made everything dreamlike, surreal. She is so feminine - hairless, tight skin (yoga) petite, but with this thick button cock I simply love sucking on. Can't get e... Read full Story
Action69 2023-04-06 4,776 Cumshot Creampie Ladyboy
86%
Party with my best friend
To continue the topic of shemales fucking girls, I am publishing this awesome story of a young girl getting fucked by her high school friend! Enjoy reading! My name is Cindy, and I am 18 years old. I have blonde hair and brown eyes, and boys think I am very sexy and attractive. But the story I am... Read full Story
shemale lover 2015-06-09 5,316 Blowjob blonde cum
95%
First Time Receiving
Within 30 minutes of small talk, she wanted Tony to fuck her. She had sucked many cocks, but had never been sucked herself.Adrian took Tony back to her apartment. He gently eased toward her on the couch. He put his arm around her shoulder. Adrian felt so excited, and felt her cock hardening.Tony ... Read full Story
shemale lover 2015-09-17 6,919 sucking shemale
75%
by a Shemale Part 3
I woke up the next morning not sure what just happened was real or if I just dreamed it than I looked around. I was laying naked in this mammoth canopy bed the bed spread and canopy were both pink and feminine and I realized it wasn't a dream I couldn't believe I was begging to be fucked. ... Read full Story
shemale lover 2011-08-29 4,288 Cumshot asshole fingering
100%
The Boy and the Fairy
Local folktales warned of Fairies, but such stories were long ignored or thought of as just a source of amusement. It was after all the twenty first century, mythological creatures were almost entirely forgotten in Dagsdown. But that didn't make them any less real. Since the age of five, Gregory ... Read full Story
shemale lover 2011-09-13 3,286 Small Tits Cumshot handjob
100%
First Real Cock I Got
I must have been around 15 and it was during a carnival festival. Most of the boys were dressed as cowboys, super heroes, firemen etc. For me it was the chance i was looking for to dress up on woman's clothes. I had picked up a mini dress, fishnet and a small top that was letting my belly free. I g... Read full Story
shemale lover 2011-09-20 2,953 anal first time shemales
50%
The Unkindest Cut of All
Darren's cock was huge, bigger, longer, thicker, harder than it had ever been, a living testament to Lindsay's beauty. The actress was even lovelier in person than she was on film, and Darren had seen a lot of her films. In fact, he'd been in two of them himself, the leading man to her leading lady.... Read full Story
shemale lover 2011-09-28 2,750 Big Cock orgasm anus
100%
Being Twins
I knew something wasn't quite right but I couldn't be sure. My life for the past 10 years with my wife Jane was great. My name is Richard. Jane was 5'8", 120 pounds, lean trim body, 38D breasts, beautiful blonde hair and stunning features. I was 5'9", 148 pounds, and little chest or body h... Read full Story
shemale lover 2011-12-19 5,312 hardcore erotic encounters fantastic
100%
The Hotel
The hotel room door clunked shut as we stood there embracing each other. The trip to the south coast had taken around three hours and I had plenty of opportunities to look across at Rachel's legs as I drove. Perhaps I should rephrase that - I had three very long hours of torment as I had just wanted... Read full Story
shemale lover 2011-12-28 2,820 anal shemales fingering
100%
Caravan
Somewhere between the coastal towns of Sherringham and Cromer there is a small caravan site. Set on the side of a grassy slope are around half a dozen pitches with fine views around the organic farm on which its a part of. Normally this would be a delightful place to be but today....................... Read full Story
shemale lover 2011-12-28 2,777 anal sucking stroking
100%
Beginnings
The Intimate Liaison You would think being at home all day while the wife works would give me all the time in the world to indulge myself as Michaella but not so. Being a closet crossdresser with a family and home to look after is OK but a great number of friends and family call in knowing I’... Read full Story
shemale lover 2011-12-28 3,445 oral orgasm submissive
100%
A Night Out Chapter 3
When I woke up Saturday morning Neerja was not in bed. I could smell bacon and eggs being cooked so I threw on my boxers and joined her in the kitchen. She had on sexy pair of cut off shorts and tight fitting t-shirt. Her back was to me so she didn't see me enter the kitchen. I walked up to her and ... Read full Story
shemale lover 2012-04-20 1,959 anal sex Cumshot fingering
88%
Pulled Over
She stammered as she answered him " Y..y..yes Officer." She wenton in her soft cultured voice"It's just that i'm going to be late to work again and my boss isso strict." She looked up to seethe the cop staring at her long legs and shifted uncomfortably. "Step out of the c... Read full Story
shemale lover 2012-05-08 2,422 hardcore Cumshot cum swallowing facefucking
50%
Training Sissygirl Part 3
Sissygirl stood, shaking a little as the tall and well-built males crowded about her soft and vulnerable body, the scent of their glistening cocks making the poor t-girl delirious; she knew she had no choice but to strip. The men stroked their cocks as the pretty sissy meekly began to remove her clo... Read full Story
shemale lover 2012-06-10 2,458 anal sex Cumshot domination little cock rimjob
100%
Olivia
So I worked with this girl at a Hot Topic in a busy mall where we both worked the same shift. I developed a massive crush on her over the course of a year. Her name is Olivia. She is a short haired brunette, with huge brown eyes, and a subtle amount of freckles around her nose. She is perfect tan fo... Read full Story
F7Z 2012-06-13 5,497 brunette Big Tits Big Cock
100%
First time with a shemale
well this all happened about two years ago when i was 18 i always have had fantasies of having a cock in my mouth and ass but i wasnt attratced to men jusst the cock so i decided to find a shemale. i live in a small town and thats hard so i found one about an.hour away in the city. so i talked to he... Read full Story
shemale lover 2012-11-04 4,208 first time anal sex orgasm
85%
Where No Man Has Gone Before
I write this with the faint hope that some day, some way, I can send it to the men of Earth. (Maybe via the Internet?) It's been over a year now since that night... I had been driving later that night than usual for me. You see I'm just a single, middle-aged guy who's good at fixing stuff. I had ... Read full Story
shemale lover 2012-11-23 4,437 sucking cum oral
100%
His Dirty Little Slut
He'd been watching her at the party all night; fishnets, short tight leather skirt, tight top, scarlet red lips, and dark hair. She looked like such a dirty whore, and she was living up to her looks; time after time she'd lead another man out the back of the house, and each time she'd return, wiping... Read full Story
shemale lover 2013-05-17 5,910 Bareback Creampie fingering ass fucking Guy Fucks Shemale