Sort by
Relevancy

Free Stories

100%
Sarah fucking in vienna
Sarah in Wien , sie nennt mir ein mir bekanntes Hotel in der Innenstadt, sowie eine feste Uhrzeit! Überpünktlich bin ich Vorort , komplett glatt , unter der Anzugshose einen schwarzen engen Nylon Slip , sneaker weißes Kurzarm Hemd, guter Duft , klopfe ich etwas nervös an der Zimmertür! Von innen k... Read full Story
Sarah Diener 2023-08-30 2,099 anal Crossdresser Amateur Cumshot Bareback Creampie Blowjob blonde Lingerie Guy Fucks Shemale sissy Ass to Mouth cum in mouth
100%
Feriengruss 22.07.24
Erneut ging es ins Cruisingworld Kirchberg. Eine herzliche Begrüssung, ab in die Garderobe und dann unter die Dusche. Bereits beim Eintreten hörte ich ein paar bekannte Laute. Als ich beim Zimmer mit der runden Liege vorbei gehen wollte, um an die Bar zu kommen, war kein Durchkommen mehr. Vom Innere... Read full Story
Cheryl_F 2024-09-02 212 Group Sex Cumshot Bareback Creampie Fetish Big Cock gangbang Shemale and Girl Guy Fucks Shemale pov Ass to Mouth cum in mouth shemale fucks female
100%
Meet Barbies Sissy
Imagination and fantasy can be a wonderfulescape as I am about to relate to you but let me first set the stage. Like many, I have been crossdressing privately for many years. My desire to wear panties, stockings, garter belts, slips and bras started in my pre-teens however, I stopped for a numbe... Read full Story
shemale lover 2011-09-18 3,503 cum dildo ass fucking
50%
Giving Away Virginia Holton
Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... Read full Story
shemale lover 2011-10-08 4,781 shemale cum ass fucking
75%
Rebound
My story is nothing new, like most girls who used to be boys I knew from an early age that I was different to all my school friends. My dad was a thug of a man, who enjoyed the physical battle of the rugby pitch as much as the post match booze up, but I took after the mother who died giving birth to... Read full Story
shemale lover 2011-11-25 6,411 anal Creampie oral
80%
Mandy Awakens Dave's Desires
We had been flirting across the bar for several weeks at this point. She was just so easy to talk to. Although she wasn't stunningly beautiful, she was quite attractive. Mandy is about 5'2" or so, 110 pounds. She has a light complexion to go with her strawberry blond hair, which she wear... Read full Story
shemale lover 2012-01-10 5,147 anal sex cum oral fingering
88%
Feminized By My Mother
Hello. My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is inv... Read full Story
shemale lover 2012-07-24 67,907 Fetish shemale oral feminization
96%
Caught
This is how I got caught masturbating and lost my virginity to my stepmom. I was still in High School but had just turned eighteen, and was still living with my dad and stepmom, Beverly. I was ashy kind in school and did not get many dates, this lead to lots of jacking off. I did not realize it at ... Read full Story
shemale lover 2012-12-17 11,165 anal taboo Masturbation oral Mature
92%
A Surprise Relationship
This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony&quo... Read full Story
shemale lover 2013-01-29 5,495 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
98%
Fantasy cums true
I was on a business trip staying in a nice Hotel. After a business meeting in my room I called down for room service. The maid came up a few minutes later and I let her in. She was stunning, 5' tall with black hair and the bluest eyes I have ever seen. Under her uniform you could tell she was very w... Read full Story
shemale lover 2013-07-11 8,698 anal sex Cumshot suck Creampie Shemale Fucks Guy fingering
41%
My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
bmogotti 2020-03-09 13,467 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 31,771 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
92%
The Girl Next Door Ch. 02 by derezzed ©
Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the sunlight that h... Read full Story
StevelovesTgirls 2019-06-11 12,796 Amateur Big Tits Blowjob Big Cock Guy Fucks Shemale
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 4,437 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
The Next Level
Nitromethane It's been a couple of weeks now since I sucked my last shemale cock and swallowed her load, and with enough distractions, it hasn't been too difficult keeping myself preoccupied and my mind off of satiating my new fixation. Still though, I do have my moments when I sit back and imagi... Read full Story
Gwapo67 2022-02-01 6,209 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
100%
The Girl Next Door Ch. 02
derezzed Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the s... Read full Story
Gwapo67 2022-05-13 5,542 Bareback Creampie Guy Fucks Shemale cum in mouth
92%
Southern Hospitality Ch. 04
XtinaSmith2017 Ash awoke feeling cold, he pursed his lips a little and shivered, curling up a little tighter, nude as he was, the action brought little relief from the cool air. He let out a soft murr of discomfort as his mind shook off the cobwebs of lingering dreams, he could see light throug... Read full Story
Gwapo67 2022-05-16 7,027 Big Tits Bareback Creampie Shemale Fucks Guy Blowjob Mature cum in mouth
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,962 Creampie Big Cock ass fucking
100%
Jack & Jill - his first time with a transexual
Jack and Jill meet It was when I went to the patio to enjoy a cigar after dinner that we met. On the road for business, I found a decent bar and grill near my hotel where I was welcome to enjoy a fine smoke. I had dinner and then moved outside for a relaxing smoke in the cool weather. I lighte... Read full Story
shemale lover 2012-04-09 5,530 anal sex oral sex cum swallowing deep throating
100%
Beefy Buns
It's hard to get good help. Probably, that's true in any business, but it's especially difficult to find decent employees in the fast food racket. Believe me; I've tried. I manage the local Beefy Buns franchise--burgers, fries, and shakes is our mainstay, but the menu also features fish and chick... Read full Story
shemale lover 2012-04-22 6,354 anal sex Creampie blonde shemale
100%
Fantasies Fulfilled
I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I think like a girl and naturally act like a... Read full Story
shemale lover 2012-05-26 4,549 anal sex Creampie Blowjob crossdressing
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 18,314 big dick anal sex suck Blowjob cock sucking workplace
100%
Porn Cinemas and GinaG
I really like porn cinemas, there is a certain seediness and sleaziness about them that makes them alluring to me. My problem is that living as I do in the south of the UK, there are no porn cinemas anywhere near me. Fortunately, I travel in my job quite a bit and so can get to cinemas in Birmingham... Read full Story
GinaG 2019-01-08 3,646 Stockings Crossdresser Amateur Cumshot Masturbation Blowjob Lingerie Mature cum in mouth shemale + shemale
100%
Exposure, Disclosure
The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... Read full Story
the greatest liar 2019-06-18 7,984 Teen (18+) Small Tits Amateur Group Sex Latina Blowjob gangbang Guy Fucks Shemale cum in mouth
81%
My wonderful life with Patl : The dinner
Hello All, Since Pat told me to serve her fully naked i was/i am really keen to back home and to make her happy. One day she told me, I hate to see you so hairy, I would like you will be fully shaved. I will be very happy to have your cock, balls and ass smooth as a baby skin. I will shav... Read full Story
jperrot 2020-07-21 4,154 Amateur Shemale Fucks Guy Big Cock domination slave guy
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 2,738 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
Wet & Messy Sex
It was the text I'd been waiting for for ages. 'I'm back.' it said. Anish, one of the kinkiest guys I've ever met had finally decided to return to his holiday home, just a few minutes away from where I live. He's a well off Asian businessman and has a lovely place to entertain. It's been a while sin... Read full Story
kiwicd 2022-04-27 3,689 Crossdresser Amateur Cumshot Creampie cum in mouth golden shower
50%
A Fantasy - Part 3
Sharon put her cell phone back into her purse, turned to Paula and I and said "I'll be right back, with the Chinese food!", gave us a wink and took out her wallet, grabbed some money and then went off to get our dinner. Paula was sitting on the floor, she leaned back on her left elbow and started... Read full Story
swollenrooster 2023-09-20 5,693 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
87%
Shemale First Time
First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married... Read full Story
shemale lover 2011-08-24 9,479 first time asshole shemale
100%
by a Shemale Part 2
I was awaken early Monday morning when Felicia lightly kissed me on the cheeks and said it was time to start my hormone regimen. I looked at her and she had her left hand opened and she had a white pill and in her right hand a glass of water. I was no longer fighting or resisting especiall... Read full Story
shemale lover 2011-08-29 6,277 anal sex sucking shemale
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,879 Crossdresser hardcore ass fucking cd
100%
Taking Ricky's Cherry
My work has me traveling all over the US and if you have read any of my previous stuff then you might have figured out that I have a major cougar streak. I just love being the first T gurl to a sexually inexperienced young guy. I was bored and horny in the hotel room, so I logged into a gay dating s... Read full Story
pennypenny 2019-06-11 8,694 Stockings Teen (18+) Crossdresser Cumshot Bareback Creampie Fetish Blowjob redhead Guy Fucks Shemale Mature Ass to Mouth cum in mouth
25%
Fantastic threesome w/ Miranda Pinocchio & Danielle Albuquerque
Today taken by the craving for something really big I call Miranda who answers me immediately and despite the language barriers and her way of speaking not always understandable we agree for 70 and a quiet thing. I sling in Naples, central area, the usual low in the alleys between via Marina and the... Read full Story
RonWisley 2020-05-04 4,925 Amateur Cumshot Shemale Fucks Guy threesome Blowjob Big Cock
100%
My new Life with Pat. Part 2
While Jean was discussing with the lady from the next table i feel the didlo starting to vibrate and then something like a small ball move up and down into the didlo, it was a prostate massage. I saw Jean playing with a remote control, He increased and deacresed the frequency of vibration and the ... Read full Story
jperrot 2022-08-09 5,242 Amateur Bareback Shemale Fucks Guy threesome Shemale and Girl domination Guy Fucks Shemale slave Ass to Mouth double anal webcams punishment
40%
See Me At Shemale Cam Tube
I was dressing when I heard a new e-mail arriving. "You're hot as hell on Shemale Cam Tube", he wrote, "Wanna meet me 4 lunch? Promise to be a gentleman!" It was cute, especially coming from such a skinny guy. I'm a big girl - over six feet, with strong legs and huge breasts whic... Read full Story
shemale lover 2011-08-09 6,678 asshole Blowjob shemale
100%
A Shemale Vacation Part 2
We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragem... Read full Story
shemale lover 2011-09-05 7,347 anal cumming cum swallowing
100%
Bagging a Bitch with Balls
Watching porn has given me a lot of ideas concerning what to do in bed--and elsewhere. Some of the guys and sluts in X-rated videos do it outdoors--in the woods, a park, poolside, or in a parked car. Some chicks flash their dicks--yeah, I watch shemale movies sometimes, too--in public places, and so... Read full Story
shemale lover 2011-09-27 5,643 transsexual ass fucking tit fucking
100%
April Fools!!
I'm Jimmy James and I've been hanging out with the same six guys since we started college. We're a pretty close knit bunch and have stayed in touch since then. At 25, I'm the only one of the seven of us still not married. Even though we all still get together for parties and get togethers, for t... Read full Story
shemale lover 2012-01-04 11,643 anal oral cd
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 3,191 anal sex Cumshot oral sex hermaphrodite
100%
Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
shemale lover 2012-10-21 8,927 anal Cumshot shemale oral
100%
Pygmalion
Some of the coed students in Professor Higgins' Sculpture 101 class regard him as a sexist or, as Amanda Blake describes him, as if she were living back in the sixties, "a male sexist pig." He does have an eye for the ladies, I'll grant you that (he's ogled me enough times!), but what man ... Read full Story
shemale lover 2013-02-22 5,361 hardcore Big Cock ass fucking Guy Fucks Shemale ass fuck
73%
Nancy the hot and sexy TS in Pattaya
Hi this is Ris, this is my third story. Well Last year I went to Thailand on lone trip. I went directly to pattaya and had rest and went to Walking Street in the evening. Was visiting many nude bars, ts Bars, dance bars. but while walking on the street one particular girl catch my attention. s... Read full Story
Stud4Shemale 2017-05-22 9,843 Big Tits Cumshot Shemale Fucks Guy Ladyboy Guy Fucks Shemale cum in mouth
85%
My dream pt 2
A few hours later I woke up and realized that I had fallen asleep. Sydney must have also fallen asleep as she was still in my arms. I tried to get up with out waking Sydney but that wasn't possible. She woke up and quickly put on her nightie so she could walk me to the door. When we entered ... Read full Story
Sydney Sun Min 2017-12-26 18,329 Shemale Fucks Guy
54%
Experience with Shemale Kadambari in Pune
PS: this is a genuine experience. Hey, I am back with another story. Let me introduce myself. I am ordinary guy who like to score shemale from Pune. I have already posted one experience with arzoo. So yes let's start, I had a normal chat with Kadambari on what's app discussing the rates. So she a... Read full Story
spidymoto 2020-03-24 6,745 Cumshot Blowjob shemale Big Cock Guy Fucks Shemale indian Indian Shemale Pune Pune Shemale
28%
Current Fantasy
I really wanna get fucked for the first time and my dream way of doing it, always wanted to do a porn. The dream is that I go there and get done up in such a way, I am unrecognizable, just looking the best. Have a tranny come in and do my make up, the way she likes it and gives me a preview of what ... Read full Story
martley 2023-06-30 5,701 anal Amateur Group Sex Cumshot Fetish Big Cock Lingerie big ass Homemade femboy shemale fucks shemale cum in mouth
100%
About Jack and Diane
Thanksgiving was over the college kids are returning to school and Las Vegas has slowed down from the busy restaurants and overcrowded casinos. It’s the best time of year to see a nice show for less. Jack’s friends had all taken off with families and he had time to think about how lonely he really w... Read full Story
Jon Paul 2023-12-20 7,435 anal Cumshot Bareback Fetish threesome Lingerie Guy Fucks Shemale small cock shemale fucks shemale cum in mouth shemale + shemale
72%
My First Shemale Sex
Another lovely short shemale story from our forum member, this time from a guy who calls himself "I Fucked A Shemale" I was at my best friends house a couple of years ago. I was maybe 18 i believe. His step mom was there. Well his new step mom that his dad just married like a few days b... Read full Story
shemale lover 2015-03-07 7,953 anal Blowjob cumshots
42%
Shemale Free Chat And Sex Adventures
It was another day at work at the mall. Being a security guard wasn't exactly the most exciting job in the world: I'd sit all and maybe get a few calls about some punk kids trying to steal DVDs. I felt like my talents were wasted there - I used to be a competitive bodybuilder, evening getting into f... Read full Story
shemale lover 2016-04-24 4,002 anal transsexual ass licking
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 12,920 sucking shemale cum
75%
Shemale Bitch
Hi there, First let me introduce myself. My name is Garry, I am 20 year old white guy with brown hair, and stand 5ft 10. I am British, but I have been living in the US for several years now, and this is a story about myself and a young shemale called Nikki. I first met Nikki when I was... Read full Story
shemale lover 2011-08-24 4,522 anal sex suck shemale
75%
The Installment Plan
“I never heard of anyone buying a Versace gown on layaway,” Karen, the fresh-faced young blonde said, admiring the designer dress on which her customer had just made another payment. Shaped to flatter, the gown was a gorgeous peau de soie satin. Its boned bustier created an incredible... Read full Story
shemale lover 2011-09-28 3,061 anal sex asshole shemale
100%
My First Time Out Part 3
Angelo was still working on Shayna's blonde wig. He fussed with it, combed it, and teased it. Angelo knew a romantic style was very important to Sir Dominique. Shayna was escorted to a tremendous makeup table. Saki placed a headband on her that stretched her scalp and raised her non-existent eyeb... Read full Story
shemale lover 2011-10-18 4,530 blonde shemale massage
100%
The Terrace View Apartments Part 3
Standing alone on the street outside the Terrace View Apartment complex, I found myself shaking uncontrollably with a mixture of apprehension and excitement. Physical exhaustion probably had a lot to do with my nerves as well. After all, I’d only begun what I had hoped would be a new life a fe... Read full Story
shemale lover 2011-11-18 3,535 anal cum oral crossdressing
66%
Tgirl
The year is 2044. My name is Robert. I am 26. Light brown hair. Dark brown eyes. 5' 9", 122 pounds. I work for a supercomputer research and development firm. Like many young men at the leading edge of technology, I am transgendered. My counselor is Dr. Elizabeth Paris. Under her con... Read full Story
shemale lover 2011-11-26 7,514 shemale transformation domination
100%
My dream encounter with a tranny
There is nothing more hot than to have a slim, pretty body on my hands to fondle. To feel their erections starting to grow and to taste their cocks in my mouth. I lose control when I'm around a shemale. I have fantasized a lot about getting fucked for long periods of time and in a lot of differen... Read full Story
shemale lover 2012-03-13 2,605 anal shemales hardcore
81%
A LadyBoy For My Wife
I have been happily married to my sexy Thai wife Lisa for three years now. My wife is Thai is petite (5'1") with a stunning figure, a tight ass and long waist length black hair. We had met in a bar in Thailand and subsequently we were married back here in the UK. She was very loving with m... Read full Story
shemale lover 2012-06-23 11,441 Group Sex Masturbation shemale Ebony facial