Sort by
Relevancy

Free Stories

0%
Janine
Janine was born Johnathan Lee Morgan. He became Janine seven years ago. See, I've known Janine (or John) since high school. He and I were great friends. He was the first person I ever told I was bisexual. And he was very receptive to it. Since high school, I have dated both men AND women bu... Read full Story
shemale lover 2012-01-18 3,309 Big Tits Big Cock Shemale and Girl
100%
A Job in the Theatre Chapter 18
"You are not going to believe this," Andrew said. He managed one of Ted's businesses down by the beach. He was one of the few employees who were aware of Ted's special interests. "Believe what?" Ted asked taking the bait. "A new guy started working out over there about... Read full Story
shemale lover 2012-03-15 3,304 gay male huge cock stroking
50%
She had a COCK bigger than mine ..oh my !
this is no B.S ,no fantasy, no make belief, no fairy tale,.. this is a TRUE STORY and an ACTUAL EVENT. iv always been a very observant k** growing up always trying to find the unseen and overlooked things in life i guess you can say curious....how curious ??:] well... there was this older lady... Read full Story
shemale lover 2012-03-16 46,836 sucking Big Cock ass licking swallowing
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 4,745 Cumshot jerking off domination Sex Toys cum swallowing
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 2,593 Big Cock fingering oral sex small breasts cum swallowing
50%
Alabama Nan in Atlanta: Round 1
It had been three years since I had last seen my family for the holidays. I don't go see them often because none of them understand, except for my older sister Karen. This year I got brave again and decided to go. Knowing how much coming home bothered me, Karen was coming up to Atlanta from Mobile t... Read full Story
shemale lover 2012-09-20 2,690 Cumshot sucking fingering
100%
Ana in Action
I had fantasized about him for months. I just wanted to know what it was luck to have him pulsing inside me, to feel his body pressed against mine in sheer lust. I just had no idea that it would actually come about and that my wife would be the hook up. You see, Jim has been one of my wife's drinkin... Read full Story
shemale lover 2012-11-23 3,021 threesome cum fuck oral
100%
Anna, Ted & She Male (Carley)
Returning from Anna's class reunion, both Ted and Anna were pleased with their adventures. Anna was able to again experience something really hard and full between her legs and Ted was able to again perform as he did a couple of years ago after being turned on seeing his loving wife with two other m... Read full Story
shemale lover 2012-12-13 4,206 anal Cumshot shemale Big Cock oral
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,608 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
90%
My fantasy of losing my ass virginity
Before I start let me tell you that I am extremely closeted and I love to dress up in women's clothes. I love feeling girly down to the last detail, starting with a complete shave down, then make-up, fake nails, a wig, and of course the sexiest and most slutty clothes and shoes. Most of the time I a... Read full Story
shemale_at_heart 2013-06-04 6,370 Big Cock ass fucking facial ass licking deep throat cd
52%
My neighbor
Peter invited me up to his place to show me the lady I saw through my window. She was a beauty with very sexy lingerie and silk stockings. Her tits were large And I could see them under her transparent top. It didn't take long before I realized she was Peter, only beautiful and sexy. Sit and... Read full Story
warmcream 2016-04-05 5,450 Big Cock cock sucking crossdressing cum sucking ass sucking
81%
My First Sissy Meet Up
I had posted an add on craigslist asking people to let me suck them off at my place. After sorting out all the answers that I got I found a guy, John, that was incredibly eager, we agreed a time and date. The day came and I woke up so nervously. But I was determined to not let it show so I got... Read full Story
Felicia Smith 2016-06-08 12,123 Crossdresser Big Cock cumming cd sissy
73%
Tabitha at 19
Tabitha’s home from her freshman year of college. She’s gone off to California to a screamingly liberal school and I’m sure she’s been making new friends, learning new things, opening her horizons and fucking safely. After I popped her cherry and we had a very discreet summer of me teaching her a lo... Read full Story
Giantsquid 2017-05-16 6,674 Small Tits Amateur Cumshot Blowjob Guy Fucks Shemale cum in mouth
80%
Ann and I
Last night I had an awesome experience. I was down in Fort Worth to meet a tranny I had been talking to on squirt. I got off work early, took a shower and shaved my cock and balls and dressed in jeans and a t-shirt and headed down to Club Changes to meet her at four. The bar was pretty empty, Thu... Read full Story
Giantsquid 2017-10-13 13,946 Small Tits Amateur Bareback Guy Fucks Shemale Ass to Mouth cum in mouth
88%
Seattle Weekend
Saturday morning and such a beautiful day nice and cool morning I went for a run. I consider myself in fairly good shape for my age but I try and make it to the top of a hill in our neighborhood. I get winded fairly quickly. Coming down the hill I ran into a nice looking athletic girl, maybe 38 year... Read full Story
Jon Paul 2018-08-09 10,087 Big Tits Cumshot Bareback Creampie Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
Regina10 2020-11-23 4,995 Group Sex Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale pov Ass to Mouth cum in mouth double anal
75%
A Tuesday To Remember
A Tuesday To Remember It was much like any Tuesday for the last year, except when I came in my wife, Deena met me at the door coming from the garage. She grabbed my arm and started leading me into the living room as she said, “You better say yes, yes to everything.” I had no idea what she was tal... Read full Story
Setinkhan 2021-04-15 6,144 Small Tits Crossdresser Interracial
100%
Nikki's Massive Strap-on
A quick recap in case you haven't read my previous stories. My name is Kacey. I'm 20 years old, white, 5'10" and 150 lbs. I have straight, shoulder length dark brown hair, light brown eyes and a thick, 6" cut cock. My girlfriend is Hannah, who also 20 years old and stands 5'10" weighing in at 140 lb... Read full Story
KaceyKlarissa 2024-02-23 4,837 anal Crossdresser Big Tits Cumshot Fetish Big Cock Lingerie Shemale and Girl domination big ass Futanari sissy cum in mouth
80%
Seduced Willingly Part 2
She must have had on lacy silky panties, but cause as she picked up the rythm doing my back and lower back with her hands, her cock was slowing sliding up and down. I was literally having butterflies, I was probably trembling in my thighs and precum was leaking out of me like a faucet. I was more tu... Read full Story
shemale lover 2011-08-31 4,804 asshole Big Cock massage
83%
Attitude Adjustment
Angel sat on a chair in a crowd of women. She had come to this club to take in a couple of shows and she was really enjoying this one! This show was a group of hot looking guys that stripped for a living, which is nothing unusual in Miami, but these guys showed the "Full Monty", or in othe... Read full Story
shemale lover 2011-10-24 5,678 asshole Creampie Big Cock
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 5,987 anal sex shemale Big Cock
100%
Tilted Kilt Chapter 5
"What can I get you tonight?" "Mojito" I walk down the bar and bend over to pull the bottle of rum of the shelf with my back angled toward the customer at the bar. I always wear my short, plaid skirt low on my hips. I'm sure the tattoo on my lower back is in obvious display... Read full Story
shemale lover 2012-01-25 3,614 Cumshot Big Cock
100%
TV Cum Slut
As we sit on the couch watching Shemale porn, my friend Bob turns and asks. "Do you still wanna be my buttslut?" "Yeah, Hell Yeah! We've been talking about it for a long time." He smiles "Did you bring some stuff to get dressed up? You keep talking about it, and I'... Read full Story
shemale lover 2012-01-27 4,726 sucking cum domination crossdressing
100%
THE WONDERFUL ADVENTURES OF MISS K: QUEEN OF THE ROAD
Miss K drove the car through the Midwestern countryside, enjoying the early spring breeze that leaked through the SUV's window as it blew through her platinum blonde hair. Her tits were held up by the tight, white, midriff-baring top she wore that stopped just below the lower curve of her tits... Read full Story
shemale lover 2012-01-28 4,056 licking sucking fucking Sex Toys
100%
A Job in the Theatre Chapter 7
The next day Paula woke late in the day. She lay in bed feeling the glow from her bottom. It was totally erotic and the most satisfying sexual experiences she had ever had. The more she thought about it the hornier she became. She grabbed her cock immediately focused on how much smaller it was th... Read full Story
shemale lover 2012-03-13 2,687 Stockings cum oral sex
95%
Three for Fun
I was on my way home from the bar one night when I noticed a group of ladies standing on the corner talking. As I approached one yelled, “hey sexy looking for the time of your life?” I stop for a minute and stare at the three beauties in front of me. “Well the time of my life does ... Read full Story
shemale lover 2012-03-26 7,100 Big Cock oral sex cum swallowing fisting
85%
My Dominate Spanish Mistress Part One
Chapter 1: Should I even put this in chapters? I have always been somewhat of a sub. My previous girlfriends have never really inspired me to go any further than the regular sex acts, missionary and such. None of them have been shy about telling me about my sexual performance, they all seemed to sa... Read full Story
bruceclark 2012-07-28 4,324 Blowjob Big Cock facial domination
100%
Ride of My Life
As a student at college I wanted a bicycle for Christmas. I hadn't past my driving test and even if I had, I couldn't afford to run one with my Saturday job wages. My parents didn't have much money so I didn't ask for an expensive model by name, anything would do. I didn't think they could go far wr... Read full Story
shemale lover 2012-09-04 7,201 Crossdresser Big Tits Blowjob Big Cock heels
100%
Transsexual Sisters Chapter 2
MICHELLE AND NICOLE TRANNY SISTERS Part 2: Living with lesbians During freshen orientation the girls kindly declined approaches from many men and some women. They needed to find their bearings and were not ready to reveal any hidden secrets yet. They first needed a place to stay and searched t... Read full Story
shemale lover 2012-09-07 4,112 Cumshot Creampie Blowjob Big Cock tits licking
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 3,852 Cumshot Blowjob Big Cock heels
100%
Voodoo
I was walking though a neighborhood, looking for a house to brake into, I came up on to this house it was small, I think about a three bed roomed house, I walked up the path, then I walk around it to find a open window or door and I found an open window leading into the cellar. Yeah, I am Alex Ha... Read full Story
shemale lover 2012-09-09 3,939 Cumshot Blowjob Big Cock Ebony domination
100%
Girly
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2012-09-11 4,408 Small Tits Cumshot fingering oral sex rimming foot fetish
100%
Francis Meets a Black Stud
First some background: I am a male, about 5'5', athletic and have long light brown hair and fair skin. I was on the swim team in high school and college. In college I had started shaving my legs and arms to cut down on drag in the water. My girlfriend at the time liked and eventually talked me i... Read full Story
shemale lover 2012-11-20 5,048 Stockings heels self sucking
100%
TV in Training
The ad on the internet read... "Submissive cocksucker needed...will train if necessary. Horse-hung master seeks attractive TV cocksucker for oral servitude. Gentle but firm master will train you to be the good little cocksucker you have always wanted to be. Send application and photos to x... Read full Story
shemale lover 2013-01-04 3,801 sucking dildo domination handjob
75%
Find That Guy: Porn TV's TG Gameshow
Freddy was nervous as hell. His girlfriend Sue had signed them up for this stupid game show without even telling him. He still wasn't sure why he'd agreed. Sure they could win a lot of money, and they'd each get a grand just for participating. And sure they needed the money pretty bad. Desperately a... Read full Story
shemale lover 2013-03-04 4,611 sucking Big Cock jerking ass fucking big boobs
85%
A Great Cocky Owner
Immobilized, that's what I was. Although I did not know for exactly how long. My wrists and ankles were tightly shackled, and I was unable to see or speak because of the tight latex hood that had been put over my head. Nevertheless, I still managed to make out through the heavy gauge rubber the &... Read full Story
shemale lover 2013-04-26 5,583 suck Big Cock domination Latex bondage
66%
New Black Friends
I go to a small discount store near my house once a week to buy candy. One sales clerk is obviously gay. He is nice to me and we have short conversations when I pay. He is a tall skinny black guy 22 years old and his roommate is short and pudgy. Over the past few months I have often thought to just... Read full Story
FunFemMan 2014-07-08 4,337 Cumshot Big Cock ass fucking Interracial cd
62%
White Sissies on Black Dicks
Sunni inhaled the marijuana, held it in for a few moments, and then released a puff of smoke in the air. The effeminate white man with a platinum blonde Mohawk pressed the number two button on his phone to listen to the message. He heard a deep-voiced Black man say he needed his dick sucked and woul... Read full Story
shemale lover 2014-09-11 12,518 ass suck Big Cock oral sex Interracial cd
100%
Double Anal With a shemale
....He answered the door and there she was beautiful as ever. He had just paid 500 dollars to have a transsexual e****t come directly to his door and greet him. She had on a long pea coat and thigh high boots. When she took the pea coat off all she had on was a one piece swimsuit. Her tits were a 36... Read full Story
shemale lover 2015-04-29 5,393 tranny suck Big Cock ass fucking dp precum
95%
James's Cum Slut Part 4; Back to Boarding School
It was back to school time and I was back in the boarding house with James. We hadn’t seen each other all summer and were eager to relight the fire. But it was going to be hard. While we shared a dorm together, it would be hard maintaining the privacy. We had both packed items from my secondary ward... Read full Story
ATC97 2015-10-08 6,980 Crossdresser teen cd (18+) cum slut latex ts gangbang sex
94%
Shemale Ride Along Part 1
I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass. Now... Read full Story
qtball 2016-08-29 12,470 anal tranny Blowjob Big Cock bj asstomouth
88%
Shemale Ride Along Part 2
Note: This is a sequel to my previous story, "Riding in Cars with Shemales." If you would like some back story into how Terra and Matt met, please read it. If not, you can probably still enjoy this one by itself. * It was a wonderful day in May. The sun was shining. The sky was clea... Read full Story
qtball 2016-08-31 11,561 Outdoor Big Cock bj Shemale on Guy self fuck
92%
A Hidden Surprise
Winter term at uni means thicker clothes which enabled me to hide some surprises under my clothes. The thicker blouses and tights would conceal anything from a thin g-string or a heavy lace pair of panties. And, me being me, I took this change of wardrobe to my full advantage. I’d been Matt’s fuck b... Read full Story
ATC97 2016-12-20 13,961 anal Teen (18+) Crossdresser Big Cock doggy style
100%
All Woman and More
It was one of those soft southern nights you hear about in movies and old soft rock songs. I could smell the long leaf pines and the moon was nearly full. I had been on my own for so long that it rarely bothered me as it did in my youth. That lonely feeling that never quite goes away. Now it came on... Read full Story
Windmillchaser 2018-09-20 10,626 Bareback Shemale Fucks Guy Big Cock sensual romantic encounters Erotic Fiction
100%
Fuck Friends Forever
"Flip over..." Those two words come as a surprise, filling my mind with expectations. I find it interesting that Brian wants to switch from doggie style to a more traditional sex position, a romantic one at that. Hopefully, he won't be turned off if he sees my cock while we're having sex. I hope... Read full Story
ASSEaster5678 2019-01-09 8,809 Bareback Shemale Fucks Guy Big Cock Guy Fucks Shemale
91%
The New Housemate's Secret
https://chyoa.com/chapter/Introduction.150836 The New Housemate's Secret How will you discover the hot new tenant's secret? Chapter 1 by Bauer1 The doorbell rings, a soft knocking accompanies the bell to break the silence of the house. You look up from your laptop nestled snuggly in your la... Read full Story
Acche 2019-04-04 21,997 Big Tits Cumshot Creampie Shemale Fucks Guy Blowjob Big Cock Guy Fucks Shemale handjob titfuck titjob cum in mouth
66%
Spring Morning
First morning of spring After the long winter it was just starting to get brighter and greener, white anemones were blooming and in a few weeks spring would be at it's most beautiful phase, but for now the gloom of night and mist was just retreating back to the sea and sun was rising giving me ... Read full Story
Femboy Emmi 2020-05-11 3,595 Small Tits Crossdresser solo Lingerie
85%
Cheating Sissy Wife
My name is Ginger and my main stud is Keith, a truck driver, who is only in town once a week. We have and ongoing role-playing fantasy that we carried out whenever he was in town. I am his dutiful ideal housewife who is perfect in every way. My talents excel in both the kitchen and the bedroom. I fi... Read full Story
Regina10 2020-07-27 7,638 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
100%
TO BE OR NOT TO BE – FINAL ACT
TO BE OR NOT TO BE – FINAL ACT by Spanky de Bautumn Part 7. Sunny spent the night with Antonio and the next day they went to Mel and Shari’s for some fun. Antonio had school, so he was up and out early on Tuesday. Mel was in the shower and I was laying in bed, my mind wandering and not real... Read full Story
SpankydeBautumn 2021-03-02 2,541 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
80%
Group Sex
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-04-19 3,194 Group Sex Cumshot Bareback Creampie Shemale and Girl Guy Fucks Shemale cum in mouth
100%
Surprise while exploring dressed
I had been dressing at home for a while, taking pictures and enjoying myself. Usually whenever I had any sexual encounters I was not dressed and had a mixture of experiences as top and bottom. This is the day it all changed though. For the first time I decided to get myself dressed and head out.... Read full Story
slvr2291 2023-06-21 6,985 anal Amateur Big Cock cd first time dressed
74%
Sexy Young Shemale
When I was twelve my next door neighbors Sam and Ted trained me in the art of cocksucking and creamy yummy delicious cum eating for hours everyday during my summer vacation and I fucking loved it! I was small framed and wore my long blonde hair in a pony tail and always wore my smallest shorts so I ... Read full Story
shemale lover 2018-09-28 10,584 sucking Big Cock cum swallowing
100%
Shemale Pussy
My wife Carol loves to bring she-males home for me to suck and fuck while she watches and masturbates. She works at a club that has she-male entertainers and there's nothing like having a hot she male straddling your lap so you can oil her smoothly shaven body down with baby oil. It's even better... Read full Story
shemale lover 2011-08-25 4,442 first time shemale Big Cock
100%
My Surprise
Here I was in another strange town; the hotel was as usual just one of Those places you sleep in and I was bored and fed up with travelling A drink I thought I need something to relieve the boredom. An hour later I was in a bar in now what was the name of this town ?, Drinking alone in the corn... Read full Story
shemale lover 2011-08-31 5,601 Small Tits sucking pussy
79%
My Shemale Stepmother Part 1
My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was re... Read full Story
shemale lover 2011-09-01 18,938 tranny Big Cock jerking off
100%
Hot Part 1
I should have realized something was going on when it first started. I was her stepfather and Angela was about 16 years old the first time she started to hug around on me. This went on for several years until she became of age. After her 18th birthday, she started wanting me to kiss her on the lips.... Read full Story
shemale lover 2011-09-08 5,171 Small Tits anal sex Creampie