Sort by
Relevancy

Free Stories

57%
Black Cock & Birthday Presents Chapter 3
I raced upstairs but had to come back for my things. Darrell and Angela laughed about how he'd fucked me silly. "Take your time, girl," Darrell said. "I want you all dolled up in case I need some later." As I showered and touched up all the places not fully hair free from m... Read full Story
shemale lover 2012-06-26 2,665 anal Cumshot Sex Toys crossdressing riding
50%
Tea-Girl's Repeat Performance
It was the last night before my girlfriend was due back from the Hen Night she was on, and I had already washed her clothes from my previous day's fun with the electricity meter reader, during which I made a mess of her satin thongs, pantyhose and white body-tight top. I wanted to relax, with a bott... Read full Story
shemale lover 2012-09-01 3,641 Cumshot Masturbation Blowjob fuck pantyhose
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 7,729 anal Fetish cum crossdressing
71%
TGirl Initiation by 3 BIG BLACK 12
In my teen years I was often told that I was quite feminine.The high school punks always told me that I filled out the back of my jeans in a girly way. After taking a shower one day I did notice that they were right, I had a nice white bubble butt. Not to mention that my lips were also quite girly. ... Read full Story
TgirlJill4BBC 2013-06-04 9,067 Stockings Cumshot suck Big Cock Lingerie Interracial Latex
87%
Encounter with a dominant shemale
One night I was feeling really horny. I just came back from the gym and I wanted to release and relax. I then began my search for some fun on the personal ads section. I have always been into shemales especially verse aggressive ones. I found this one particular post about Asian bottoms. I was c... Read full Story
SecretAznMan 2013-06-28 47,988 Cumshot Shemale Fucks Guy Big Cock Lingerie ass fucking ass licking big boobs
95%
Shocking shemale surprise
I had been out with friends partying after a professional basketball game and reached my hotel around 12:00 I wasn't yet tired and not needed anywhere the next day I decided to call for a massage. I had an adult newspaper and really didn't read the add. I basically called the first number I came ... Read full Story
shemale lover 2013-06-25 7,090 Cumshot suck shemale oral Lingerie cum swallowing
97%
MY FIRST SEX WITH SHEMALE
This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... Read full Story
shemale lover 2014-11-23 26,243 tranny suck shemale fingering Lingerie ass fucking
89%
Four Inches Cock
[Fiction] I've always thought dating coworkers is weird and awkward but here I am walking upstairs to my apartment with my coworker after a nice first date at Italia Parlor - the best calzones for miles. Natalia is a gorgeous, pale American-born girl of Slavic descent. She has raven hair th... Read full Story
Uevari 2015-06-23 8,169 tranny suck Blowjob oral sex deep throat
65%
Prostitute Shemale
Im a shemale prostitute,and yesterday one of my customers, booked me as an out call to his hotel, I was dressed super sexy and looked hot, even the taxi driver couldn't take his eyes off me, so I gave him a little show and opened my sexy shaven legs, anyway got to the hotel, went up to my clien... Read full Story
pjboys 2017-04-18 8,251 ass suck Blowjob shemale cumming oral sex
100%
yes, Mother give it to me
"Do your fucking job right, Henry! Jesus Christ, what are you, five years old? If I ever have to call you in here again, you're done! You hear me? You'll never work in this business again! Now get the hell out of my office." Mona could feel every set of eyes on the floor anxiously awaiting the pi... Read full Story
ASSEaster5678 2018-11-28 12,775 Guy Fucks Shemale
66%
Sex in the kitchen with my hubby's friend - a cop
Ever since my wedding last year, I enjoy a great time with my hubby who loves me so much and takes care of me so much. Since he is married and having another family, he doesn’t stay with me all the time, but comes and stays at least 2 or 3 days in a month and we literally celebrate those nights wit... Read full Story
Manusha Tranny 2021-10-14 5,243 Small Tits Crossdresser Amateur Cumshot Outdoor Blowjob Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
50%
I'M A DIRTY WHORE EXPOSED TO PUBLIC HUMILIATION
There are people on porn sites who hunt down people like me and make me a world famous whore. They download all my photos that I publish. Sometimes they add descriptions to photos. They share my photos on all known porn sites, forums, chat rooms. More and more people have my photos. Some people edit... Read full Story
QUEEN HARLOT 2022-02-14 3,062 Big Tits Cumshot Blowjob public humiliation cum in mouth double anal whores humiliated whorehouse degrading degraded public humiliation
100%
Kate Berges the Shemale who fucked first in my ass
I was with her last week. She was in a duo. So I went there and rang the bell. Recognized me right away and gave me a deep kiss. I then asked her if she was available in the duo and her colleague a.) cums properly and if she would also fuck each other, which she confirmed. She then went out and c... Read full Story
Bigpruegel69 2023-12-17 6,813 Cumshot Creampie threesome Blowjob cum in mouth shemale + shemale
88%
Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
Regina10 2024-02-14 5,210 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
94%
New Girl in Town
Margo sat next to me in the coffee shop late that Saturday afternoon. His real name was Mark, but he was one of the loveliest Drag Queens in New York City. I had been dressing secretly at home in my mother’s and sister’s clothes for just over three years, but at 18 years old, I had never... Read full Story
shemale lover 2019-06-04 10,061 anal shemale oral sex
85%
A Girl Called Eddie
Carrie had always treated me like her little sister, even though we were only third cousins. Though she was only two years older than I was and not of exceptional physical stature, I had allowed her to dominate me for as long as I could remember. Not that she was exceptionally cruel or abusive in an... Read full Story
shemale lover 2011-08-14 5,452 anal sex asshole Lingerie
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 3,822 shemale orgasm nipples
100%
Shemale Adventure
You: early 20's, tall boyish good looks with a lean and muscular body. Dressed in tight leather pants, from behind your tight buns are revealed by the shiny black leather, as are your cock and balls from the front. You are wearing black leather boots and a denim shirt that refuses to hide your stron... Read full Story
shemale lover 2011-09-06 4,377 asshole Lingerie bisexual
100%
A trip to the dentist
My wife thought I was at the dentist but I was really with my special friend Sandy. It had been over a month since I could sneak away to see Sandy. My cock was wet and hard just from the ride thinking about what she would be wearing and how we would please each other. When She met me at the door I a... Read full Story
shemale lover 2012-01-22 3,628 anal Shemale Fucks Guy cum
71%
Shemale fun
Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... Read full Story
shemale lover 2012-03-16 2,855 cum oral sex swallowing
100%
Party Surprise - First sex as a Crossdresser
This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly s... Read full Story
shemale lover 2012-05-21 7,514 first time hardcore anal sex Cumshot oral sex crossdressing
100%
Shemale snapped
Camilla took a few steps out the door of her balcony to get a feel for the temperature. Thankfully it was cool out. It had been a hot day, which meant a cool night was welcomed. She closed the door and pulled out a pair of gold hoop earrings. She was suffering from a mild case of the jitters. The... Read full Story
shemale lover 2012-06-21 6,254 anal sex Creampie shemale Big Cock
100%
Shemale Whore and Arab Pimp
Hermaphrodite Whore It had been over a year since Johnny threw that tantrum that ruined me and got him excommunicated from mom. Holding me down when mom walked through the door with her friends, colleagues, whatever and they all gasped and screamed as my big brother finished doing me. We had... Read full Story
shemale lover 2012-07-24 3,036 anal sex Cumshot oral sex hermaphrodite
100%
David to Dee Chapter 2
His nipples had grown considerably over the last two months. Gina had been putting those little nipple suckers on him twice a day. Dave wouldn't be going to the gym anymore. Well, it had been a long time since he'd gone to the gym, anyway. Since Gina had had him shave his entire body, last spring... Read full Story
shemale lover 2012-07-30 5,782 anal sex Cumshot oral sex rimjob
100%
The girl inside me
I with my dolls outside the yard with Amber. What the fuck are you doing you little sissy? Screamed my daddy as he grabbed the doll out of hand and pulled me into the house. That day I learned what boys do and what girls do... but daddy I am a girl I said. Daddy looked at me just shook his head boys... Read full Story
shemale lover 2012-11-05 3,280 fingering facial oral sex sissy rimjob
96%
A Trip to the Beach
I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, n... Read full Story
shemale lover 2013-07-21 10,509 hardcore Cumshot Shemale and Girl oral sex kissing
80%
Owned sissy girl
I met the mature dominant couple that I now call Mummy & Daddy on the internet. Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for... Read full Story
Andrellina 2015-09-23 29,059 anal ass rimming cd sissy
92%
My Introduction to Crossdressing
I hope my story is appropriate for this site. It is rather basic in detail, but I have wanted to tell others how I got started for quite some months now. When I was twelve years old I started masturbating. At that time all my fantasies were about girls. Masturbating became quite an obsession with ... Read full Story
young&rampant 2016-03-08 6,008 first time ass cum masturbating
85%
My Knight
I felt good as a looked around the club and watch the Queens on stage perform their acts. I felt like I belonged here among this faction of society. Drag queens and Trannies were my people and the only thing I regret is being in the closet and not having the courage to do it more openly. However i d... Read full Story
Regina10 2020-06-23 3,838 Bareback Guy Fucks Shemale Ass to Mouth shemale + shemale
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 2,539 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
87%
I love cock!
• Hey guys I’m Jay, let me tell you how I learned I love cock. My first time was in college, and I know they say it’s a time to experiment. But boy did I learn a lot about myself. Like most kids I had a part time job for some extra cash. One of the guys in my department was an older heavyset guy nam... Read full Story
lkusex 2021-06-03 5,997 Amateur Masturbation Big Cock cum in mouth
100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,352 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
83%
the start of what to cum
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often mo... Read full Story
oliviabecket23 2023-07-04 6,748 Crossdresser Lingerie domination Sex Toys femboy forced webcams
100%
Brandi the Shemale Cums After MNF
So, I come home from watching Monday Night Football with some guys at the local pub. I turn on the TV and some infomercial for an exercise machine comes on. The model working the machine has a great body and seeing her workout is really working me up. My cock even gets a bit hard. Feeling a bit o... Read full Story
shemale lover 2014-04-25 7,107 tranny ass fucking ass licking
92%
A new girl around!
You know, things, I’m gonna tell you about started when I was a teen. I was like every teen guy, I loved web porn, looked at porn on the internet, surfing porn sites through the web space and masturbated a lot. I loved and now love to watch lesbian porn: it was so hot watching girls having sex... Read full Story
shemale lover 2014-05-21 18,565 shemale fingering cumming
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 15,295 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 24,400 shemale oral sex stiff cock
100%
Foot Massage by a Shemale
My wife and I had just finished a nice Sushi dinner in an upscale restaurant outside of LA, with an old college friend of hers. We strolled down the boardwalk and were almost past an asian style massage spa, when my wife said why don’t we take advantage of their 45 minute foot massage for $... Read full Story
shemale lover 2018-05-12 12,715 sucking shemale cum
80%
Me And Two Shemale Lovers
The ad in the local “underground” paper said “2 hot she-male lovers looking for inexperienced open-minded male for exciting new encounters….” It added a few brief descriptions etc. I thought to myself. “Why not, you’re open-minded and adventurous?” So... Read full Story
shemale lover 2011-08-09 6,545 anal sex shemale oral
80%
My First Encounter With A Shemale Escort Part 1
I was feeling extra horny as I walked up the stairs to the apartment. Knocking on the door I heard a voice from within say "come in". The door was unlocked, so I walked into the hallway which led to the lounge. Seeing no-one around I called out "hello", to which a reply came &quo... Read full Story
shemale lover 2011-08-16 4,748 anal sex shemale genderbending
100%
First Time With Shemale
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... Read full Story
shemale lover 2011-08-26 3,809 anal Creampie shemale
0%
The orgy with a shemale
I had to move to Japan back in the fall of 2004 and lived in Tokyo in a 3 room apartment.I could not pay all of the rent so I lived with a female school teacher age 27 years of age and japanese.Her name was Miki.There was a one more girl who was friends with Miki ,I never seen much of her.Her name w... Read full Story
shemale lover 2011-08-29 5,179 Big Tits asshole Big Cock
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 18,935 tranny Big Cock jerking off
85%
Lilly's Cock
Arriving at Wayne's house just after midday, I could hear voices and music coming from the back of the house, so walked down the side passage and through a gate into the back yard. There were about twenty people there, some in the swimming pool, some standing around the barbecue, others sitting on d... Read full Story
shemale lover 2011-10-08 4,214 shemale oral sex cocksucker
76%
Sissy Mailee's first black cock
As long as I could remember I have always had a craving for black cocks. My first time was a few years ago after partying with a friend of a friend. I had called up one of my CD friends, Suzy, to attend a Halloween party at a local warehouse. We had agreed that we’re both going to the party... Read full Story
shemale lover 2011-11-06 7,192 anal first time shemales
94%
My first shemale
This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when... Read full Story
shemale lover 2012-02-12 13,283 first time Creampie Shemale Fucks Guy
66%
A Girl's Best Friend
The party was in full swing when Ryanna and her friends arrived. Of course, they were an hour late, since Glenys had gotten lost on the way. The house was out in the back woods; the owners didn't exactly go out of their way to make it easy to find. Their fellow townspeople probably would have frowne... Read full Story
shemale lover 2012-03-06 5,486 Crossdresser Shemale and Girl oral sex condom sex
100%
Shy girl with a big secret Part 2
After Maria unloaded her seed in my mouth, I was amazed at the flavor, for it was sweet like sugar but had a bit if a salty tang. I kept most of her seed in my mouth, turned around, and kissed her full on the lips, letting the delicious cum flow from my mouth to hers. As this was going on, I started... Read full Story
shemale lover 2012-03-25 3,090 anal sex Cumshot huge cock large breasts
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 4,744 Cumshot jerking off domination Sex Toys cum swallowing
66%
A Night Out To Remember Part 2
Decisions... decisions... we all make decisions everyday and most of them are simple easy decisions. Some may take hours, some take seconds and some are made before we even know it. Some decisions carefully planned and some have planning at all. Some decisions are between several choices and some ar... Read full Story
shemale lover 2012-04-20 2,918 anal sex Cumshot Sex Toys
83%
Tgirl Shemale porn cinema slut
As you know I'm very much a normal living sort of TGirl, cooking, shopping, cleaning, just day to day stuff like everyone else...I haven't started baking cakes for the local Women's Institute or joined a knitting circle yet, but I'm sure you get the general idea!! Sometimes, however, I get the ur... Read full Story
shemale lover 2012-05-07 4,730 shemale oral sex bikini heels
73%
Black Girls Have Big Dicks
She was like no woman I had ever seen before. She walked into a room and everyone's eyes were on her. She just had that incredible presence that just lit up the room and everyone just wanted to be around her. I was working behind the bar of a trendy club when I first saw her saunter in on her long l... Read full Story
shemale lover 2012-06-27 21,316 anal sex oral sex black cock
69%
Addicted to Candy
Almost two long weeks had passed since my first meeting with my new slave Candy. Our first encounter was special and my sexy new sub had not left my mind since he walked out of my door. His juicy ass and hard thick cock have filled my thoughts each day since. I had found myself wildly attracted to C... Read full Story
shemale lover 2012-08-12 3,602 anal sex Fetish cum domination Sex Toys cd
100%
Weekend Office Sex
So I am the low man on the scale at work. My job is with the City I work in dispatch and am one of the people responsible for getting road crews, hydro and sewer crews out to fix problems wherever they occur. My boss is a very attractive woman named Jamie. She stands about 152 centimeters and dark c... Read full Story
shemale lover 2012-08-24 4,171 anal sex jerking oral sex deepthroating
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 14,823 Cumshot Masturbation Blowjob ass licking redhead
77%
Anything to make a sale
“David, you are not the right sales person for this account. I know the CEO of Cybertix very well, he’s been a client of mine for years, and he won’t relate to you.” I was sitting in the office of Victoria, my boss. There was a big sale opportunity at Cybertix and I badly ... Read full Story
shemale lover 2012-09-17 4,795 first time Cumshot Lingerie domination oral sex cum eating