Sort by
Relevancy

Free Stories

100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,061 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
100%
Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
Curious_billy 2023-05-07 7,343 Teen (18+) Amateur Cumshot Asian Ladyboy domination Homemade cum in mouth
100%
Dressed in holiday style Part 2
I was up by 1 p.m., showered, changed into some fresh panties and donned some hated boy clothes to hit the streets. I stopped by a local coffee shop (not the national chain-brand type) and over a mocha latte the barrista was kind enough to give me a few pointers about where she thought the best holi... Read full Story
shemale lover 2011-11-20 2,068 anal Stockings cum
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 3,625 anal Shemale Fucks Guy cum
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 3,302 gay male huge cock stroking
100%
Proud To Be A Sissy Chapter 4
As usual, Mr. Clark was sitting in his recliner when I went into his house. "Good morning daddy," I beamed kneeling before him. "Morning," he grumbled but smiled and said, "more like afternoon." But you do look sweet." "Thank you daddy," I rep... Read full Story
shemale lover 2012-12-24 8,148 Cumshot sucking Big Cock gangbang bukkake
86%
My TS experience in India, Pune
Im 6 ft tall fair with handsome looks and regular exercise keeps me fit and healthy. Im also blessed with quite big and thick cock with indian standards. Im total shemale fan and I watch shemale porn crazily every day. I was in search of TS or Shemale in pune since long then one day I was searchin... Read full Story
daynightfun7 2013-07-10 13,186 suck shemale fingering ass fucking Guy Fucks Shemale condom sex
97%
Never Wanted To Be Your Girlfriend Ch. 02
So, after being made up like a slut, left glued to a pair of silicon breast forms, and caught sucking-off my best friend, I was pretty sure my day couldn't get any worse, but I had come nowhere near the end of my torment, as Michelle now had something else planned that I was probably not going to li... Read full Story
shemale lover 2014-07-21 9,489 hardcore Cumshot suck Lingerie ass fucking
56%
Big cock shemale from Pune, India
I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... Read full Story
Stud4Shemale 2017-05-22 95,920 Big Cock Asian Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
60%
Sucking mature huge cock stepdad
When mom passed my stepdad KEN was alone for 3 yrs he made comments like you need tighter shorts your hair smells pretty one day as I was Su king my friends 5 inch cock as he surf cum on my face KEN walked in my room then told my friend to leave I started to cry and he said it was ok he new i was a ... Read full Story
Cumsuckinfool11 2018-04-11 7,651 Crossdresser Blowjob Ass to Mouth cum in mouth Big cock dad
88%
Tommy Tries to Make It Up
Tommy Tries to Make It Up I have written about Tommy before. He was the eighteen year old neighbor that always stared at me checking me out, basically eye fucking me and that made me so hot and horny I eventually took his virginity and trained up on being a great lover. Well he had moved out... Read full Story
pennypenny 2019-04-30 6,209 Crossdresser Group Sex Bareback Creampie threesome Blowjob Big Cock redhead Guy Fucks Shemale Ass to Mouth
85%
Loving Strangers
In the past I had never failed to disclose my sexuality to a new male prospect. I looked good in my tight dress that showcased my woman's ass, and the spike heels that made me look so fuckable. I knew from past experience that guys could get really pissed and violent when they found out you weren't... Read full Story
Regina10 2020-06-23 4,690 Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Ass to Mouth
97%
Shemale fucks guy - My gf fucks my slutty ass.
I have a shemale girlfriend & we both are in a relationship. One day, I decide to give her a visit. I'm 5'7 guy & she's 6 feet. That makes her tall & intimidating & whenever we meet, it's me who become her gf. I visit her, she takes me in. SHe pulls me towards her while giving me a deep kiss. I ... Read full Story
glodobox 2020-12-04 22,212 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade cum in mouth
87%
TO BE OR NOT TO BE – PART 1
TO BE OR NOT TO BE – PART 1 by Spanky de Bautumn This is a story about how taking a play to New York City changed people's lives. A transgender coming of age story. I was born Harold Stanley Dayes, not a great name for a kid growing up. I know my parents loved me, but Harold was my mom's dad a... Read full Story
SpankydeBautumn 2021-02-22 3,860 Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob Ladyboy Lingerie Shemale and Girl cum in mouth
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,649 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
TO BE OR NOT TO BE – PART 3
TO BE OR NOT TO BE – PART 3 by Spanky de Bautumn Part 2. At the hotel in New York City, Sunny meets the bellhop, Antonio, and they go out for a drink when he gets off of work. The call came at exactly seven. I had woke up about five minutes before and was watching Antonio sleep. All of the oth... Read full Story
SpankydeBautumn 2021-02-23 2,523 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
hippocampus_171 2023-01-11 4,357 Stockings Crossdresser Amateur Group Sex threesome Big Cock domination Mature foursome Homemade cum in mouth shemale + shemale milfs
100%
Philippines Vacation with a Dominant Big Cock Ladyboy
I am still in a state of unbelievable joy that I was lucky enough to experience this but I 100% did and I can’t stop thinking about it as I thought things like this only happen in porn or fantasies. Buckle up because this is a wild one and happened in Manila May 2024. I had the opportunity to vi... Read full Story
AllenB 2024-07-14 2,598 Bareback Creampie Shemale Fucks Guy Big Cock Ladyboy Guy Fucks Shemale cum in mouth domination act filipina ts filipina ladyboy
88%
My first taste of shemale cum
This horny story was posted at our forum by a guy named Capablanca who seems to have finally admitted he prefers playing with shemale cocks over playing chess. ;) I have already described my first encounter with a shemale - an amazing experience. One thing I've been looking for since that first e... Read full Story
shemale lover 2011-06-28 40,431 Blowjob cum domination
87%
Big Booty Black Boy Gets cheated on
I have been secretly bi throughout my life. But nobody has known. I have had several girlfriends and all. One physical trait that I developed at the age of 18 was a big booty. It grew so much that I couldn't hide it much. One time I went to the gym with tight clothes and my curves were obvious. A lo... Read full Story
Flatch 2015-10-29 7,458 tranny ass Ebony
85%
Continuing to Love the Feeling
After an exhausting but exciting day, i slept very well and arrived the next morning ten minutes early. I went through the back basement door and began changing. Ten minutes later i heard Mrs. Hawthorne calling me, Bitch Sheri come up here now! My maids outfit wasn't complete but i went up to ... Read full Story
shemale lover 2011-11-03 3,481 asshole sucking cum fingering
100%
A Cock Loving Slut
My name's Jake and this is the story of how I became a cock craving slut. It started a year ago, I was walking home in the rain, when I slipped and fell into a muddy puddle. As I bundled myself up, a car pulled up beside me and rolled down the front window. I recognised the face of Neil, a man fr... Read full Story
shemale lover 2012-02-23 3,966 Fetish cum fingering Sex Toys feminization
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 46,830 sucking Big Cock ass licking swallowing
100%
Bday wish cum true
It was my thirtieth birthday and my wife Alisha had a surprise planned for me, it was one surprise that I will never forget. I found myself on a plane going to Amsterdam, Alisha had planned a dirty weekend for us and what better way than to spend it in Amsterdam. We did the usual, walked round the r... Read full Story
shemale lover 2012-08-14 4,699 Masturbation cum domination oral sex
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 4,088 big dick sucking porn
92%
Proud To Be A Sissy Chapter 6
It was still early and I wanted to enjoy the feeling of being dressed in my shear hose and garter belt, tiny g-string panties and matching bra and the form fitting shiny black mini dress that barely covered my stocking tops for as long as possible. So I spent some time doing some domestic chores and... Read full Story
shemale lover 2012-12-24 6,296 sucking domination ass fingering deep throat cd
88%
In my bedroom...
Daddy walks in to my room and lays down in bed, right behind me. He starts caressing my stocking covered legs…daddy likes it when I lay in bed in my sexy lingerie. I’m wearing a white garter belt, white stockings and silky white panties. Daddy caresses my sissy bum as he starts kissing my neck and m... Read full Story
lea1234 2014-10-07 5,610 Cumshot suck ass fucking 69 cd
86%
Valerie Halls Car Trouble
I am a teenage trans working my way through college was on my way home from my night job at an adult store in my little SUV when the engine died so I pulled over to the side of the road and put my flashers on. I get my cell out called the roll back service that I knew and waited a short bit for Henr... Read full Story
CeeRVee 2017-05-02 6,168 fingering ass fucking hard dick stroking Ass to Mouth
100%
Fuck Talk with Melanie Jackson (A talk show transcripy)
THIS IS AN ORIGINAL TRANSCRIPT OF THE PROGRAM “FUCK TALK W/ MELANIE JACKSON” DATED MARCH 10TH 20__ MUSIC CUES ANNOUNCER: Hey everybody! Welcome to “Fuck Talk” with Melanie Jackson”! The show that talks about, you guessed it! FUCKING! Any kind of fucking! Straight fucking! Gay fucking! Any kin... Read full Story
bennyx709 2018-08-28 4,617 Cumshot Blowjob Big Cock Interracial Mature
80%
Three In A Day
Clara felf especially slutty today. She briefly gazed at her long legs shimmered in the smooth, silky black stockings, and black patent leather pumps as she pressed the gas pedal of her car. Her olive skin and black wig were set off by the brightest shade of red lipstick she could find. Driving d... Read full Story
iluvgurls 2018-11-12 4,590 Small Tits Crossdresser Group Sex Cumshot Blowjob cum in mouth
100%
Quick trip to the park
Monday Morning again, I hate Mondays, why can’t the week start on Tuesday! Thought Justina ,while she stood semi naked in the kitchen drinking her coffee with a semi. I finished my coffee and made my way to my bedroom to get dressed. As I entered my bedroom i spotted my new dress i’d bought on S... Read full Story
Samantha Jewels 2022-01-12 2,334 Crossdresser Amateur Cumshot Outdoor Blowjob Mature crossdressing Ass to Mouth cum in mouth crossdresser amateur
100%
The 10 in Bay 10
On the USS Corinth, there were 10 bays - the first bay was for the captains and their personnel, the second bay for first class, the third bay for business, and so on. The back bays were reserved for the ship’s workers. All the way back in bay 10 was the engineering bay. Those in bay 10 rarely inter... Read full Story
sevon 2022-10-03 4,781 Cumshot Bareback Big Cock Futanari shemale + shemale
100%
Used in a hotel room
This is a recurring fantasy I have about being used in a hotel room. I’m working on making this a reality but for now this will have to do. I travel a lot for work and end up in many cities across the world. Usually I am out and exploring bars and restaurants. Always ends with me jerking off alo... Read full Story
slvr2291 2023-01-11 4,661 anal first time Big Cock fantasy Surprise
100%
mushrooms in all shapes and forms
Mushroom season is open! Yummy! I love mushrooms, in all shapes and forms. We were about fifteen mushroom lovers who only get together to pick mushrooms, without any other friendly gatherings! For this last outing of the season, our splendid instructor was accompanied by her cousin, who was sup... Read full Story
hippocampus_171 2023-11-24 6,505 Small Tits Amateur Cumshot Mature small cock big ass bisexual cum in mouth bald men glabrous
100%
Late Night Snack (Touch me in the morning)
I was awakened abruptly by someone banging on my door at 1am. At first, I thought it might be Harry, the man who replaced Mr. Cobb in my bed a few nights ago. He had been persistent and horny constantly. I think it was because fucking trans women like me was new to him and he hadn’t got enough of th... Read full Story
Regina10 2024-03-28 3,945 anal Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Ebony Ladyboy Lingerie
100%
Ill take all the cum I can get
I'm so horny today. I need some dick bad. So I dress up, I put on a sexy push up bra, a slutty lace top, a naughty little g string, and lacy thigh highs with a garter belt. Before getting dressed I showered and gave myself an enema. After I showered, I used some fds so I smelled sooo good after ... Read full Story
spreadforalldik 2024-07-09 1,072 anal Crossdresser Group Sex Cumshot Creampie Blowjob ass fucking Ass to Mouth cum in mouth spitroast
81%
TV loving cock
Sorry I didn't keep you posted on Saturday night, but I was sorta busy being my usual slutty self. Story to follow: I talked to a guy on megaphone. He works as a night security guard at a big office building on the edge of town. He is there all by himself in this huge, mostly vacant building, in ... Read full Story
shemale lover 2015-11-17 5,738 Cumshot sucking Big Cock
100%
Sex In Stilettos
Standing before the full-length bedroom mirror, I treated my reflection to an almost unjustly critical appraisal. My indecently short black leather dress clung for dear life to my every curve and went perfectly with my high heels, whorish fishnets and black leather jacket. It was the sixth outfit I ... Read full Story
shemale lover 2011-08-13 4,453 Cumshot tattoo cum swallowing
100%
I am a Shemales' Bottom Slut Part 2
I have been with Nancy and I have moved in and quit my job and I run around her house naked 24/7 so she can take me whenever she wants and I love her cock. She has taken pics of me naked with her cum inside my ass and posted them on the web. Nancy said," We are going to have a party to... Read full Story
shemale lover 2011-10-04 3,930 Creampie cum oral
100%
In My Place
I looked disbelievingly at the clothing on the bed before me. They were all mine; all of them. How did she know? How did she find them? I just could not believe what was happening to me. I could not do this. It was not what I had ever wanted, despite what she appeared to think. And him....... I h... Read full Story
Loveto 2011-10-12 3,994 cum transsexuals crossdressers
75%
Pleasure in the Park
I'd ridden that ride a thousand times.... But I just kept getting back into that huge queue line. I was at the local theme park riding the newest addition to the ragtag assembly of attractions, the Master Exploder. It was the craziest coaster I'd ever dared step my foot into. Everyone else loved ... Read full Story
shemale lover 2011-10-26 3,327 first time Stockings cum
50%
A threesome to remember
After a few cocktails I was relaxed in the chair as I watched Annie unbutton Jeff's shirt and kiss his chest. Her ass was right in front of me as I watched her black nylon covered legs run up to her tight skirt that just covering her full ass. She knows how much I love tight skirts and nylons and fo... Read full Story
shemale lover 2011-11-07 2,677 shemales sucking cum
88%
A happening in the bar
I was tired. I was tired with daily boring routine. I really needed to change something. My life had become boring and my sex life was expressionless. All women I knew proved to be untrustworthy, light-headed and superficial. I really wanted to take a break from the world. I just wanted to live my l... Read full Story
shemale lover 2011-12-05 3,487 first time big dick oral sex cum swallowing
100%
Tony to Tanya Part 2
Tony woke up on Saturday morning feeling excited without knowing exactly why. He tried to sit up, but his left arm was pinned down by Sarah's body. This was normal for a Saturday morning, since she tended to sleep at Tony's house on Fridays. The reason he was excited suddenly hit him. On Tuesday,... Read full Story
shemale lover 2011-12-19 3,153 sucking transsexual cum swallowing
80%
A Drive in the Country
It had been a rare hot dry day and the evening promised to be hot as well. Toni the lovely CD I have met down here in Wales arrived as arranged just before dusk in his car to collect me and take me somewhere secluded he had found for some outdoor fun. We drove about a mile before Toni pulled over... Read full Story
shemale lover 2012-02-29 3,855 Stockings Blowjob huge cock wanking cd
100%
A Job in the Theatre Chapter 5
An hour later, with a few drinks behind them, they heard a knock on the door and Paula knew it was show time. Sarah introduced her two friends to Paula and then fixed drinks for everyone. Paula fought back pangs of nervousness and tried to remember all the things he had learned from Sarah to cond... Read full Story
shemale lover 2012-03-12 3,065 suck cum swallowing
100%
A Job in the Theatre Chapter 8
Sarah smiled at her. "Oh yes dear. I will be happy to teach you. Don't worry about a thing. I will show you how to be the best damn girlfriend he has ever had." Paula was so relieved to hear that. If anyone could teach her how, it was certainly Sarah. "But first...first you need to he... Read full Story
shemale lover 2012-03-13 2,455 shemale cum oral sex
100%
A Job in the Theatre Chapter 15
Making Gary my bitch Paula got to the theatre early Thursday and got dressed and did her makeup. There was still at least an hour before the curtain went up. She knew Gary would be waiting for her in his dressing room. She knew his cock would be hard too. She could just imagine the thoughts going... Read full Story
shemale lover 2012-03-15 2,249 sucking cum massage kissing slurping
83%
Becoming Missy
It all started back in 1973 in Seattle, Washington. I was 21, living on the south side with a couple of buddies while we were all stationed at area military bases. One Friday night we had a party at our apt. I was standing outside by my car smoking a joint when this guy pulls up in his pick-up. &quo... Read full Story
shemale lover 2012-03-31 3,754 Fetish cum oral sex crossdressing rimjob
33%
Superstar fun - an evening to remember!
Starting with a little history, let me say that I started getting into tranny fun back around 1990. I went on a visit to New York and had always been an avid reader of Screw magazine/ newspaper. Before the Internet was in full-bloom it was distributed nationally to all cities around the country and ... Read full Story
shemale lover 2012-04-03 3,047 anal sex cum ass licking oral sex 69 position
0%
A Night to Remember
PREFACE I kept my female alter ego (Nicole) a closely guarded secret from my wife for over 15 years of our marriage. I've always enjoyed exploring my feminine side from a more realistic sense -- most cross dressers I met try to wear skimpy outfits and stockings that only a handful of genetic wome... Read full Story
shemale lover 2012-04-28 3,415 anal sex cum nylons
90%
Adventures in Babysitting
When I was 14, me and my BFF, Ashley, started our very own babysitting service. She made an announcement during church and we immediately started getting phone calls. One day, Ashley said, "Come here...U gotta check this out." And she pulled out a handful of 20's. "Damn, where'd yo... Read full Story
shemale lover 2012-08-14 6,106 Crossdresser cum fingering oral sex
100%
Desiree and Big John
It had been only a week since I'd introduced "Desiree, the Hot to Trot Transvestite" to my girlfriend Suzie, leaving me not a bit surprised that she chose not to spend the very next weekend at my place. While she hadn't freaked out, she was concerned I was gay since I was so convincing but... Read full Story
shemale lover 2012-08-20 4,469 first time anal sex transvestite cum swallowing
100%
First Time as a Cum Slut Chapter 2
The next day I was very excited and nervous. I put on black stockings, black lacy panties, matching bra, padded it out, and put on a pale blue top with a short flared pleated grey skirt. As I walked along to the spot, I had butterflies in my stomach and nearly turned to go back home, but he appea... Read full Story
shemale lover 2012-10-05 2,988 anal cum oral crossdressing
96%
How I Really Got My BA In College
I was living in an off-campus apartment building two months into my first semester of a two year BA program. I lived on the 22nd floor and my three friends Ray,Jim and Dan lived together on the 13th. As it was Friday night I threw a couple loads of laundry into the wash and went downstairs to cadge ... Read full Story
shemale lover 2013-02-12 6,238 Cumshot sucking Blowjob ass fucking swallowing
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 6,364 Big Cock ass fucking facial ass licking deep throat cd