Sort by
Relevancy

Free Stories

69%
February 2nd
February 2nd. My first time being fucked in my ass. It was unbelievably satisfying but I want more. I was on a dating app for guys looking for guys. I was just curious never thought that I'll be longing for a dick in me. My first was so-so.. the 2nd time just a few hours after my first was fantasti... Read full Story
Princess Raven 2020-02-06 4,287 Crossdresser Amateur Blowjob Big Cock Asian domination Homemade
16%
First timer
Hello, im a guy, naked on my bed. First time since ive posted, tell me how would you handdle my asshole? Thats not been touhed... :*... Read full Story
Ve18 2020-02-21 2,573 Amateur
81%
JUST.... MY EVERYDAY FANTASY
No one knows of this. My dirty secret.... I get so hard always thinking about the next time I can get away and escape, put something on, smoke some pot, get fucked up and just get dirty. Always starts out me planning... finding a new toy, something new. I've tried many different things, you kno... Read full Story
martley 2020-03-23 4,313 Amateur Lingerie hotel room
100%
My First Experience
Preface: A few years ago I was surfing craigslist (back when that WAS a thing) and found a couple looking for a man. I responded to that post and went back and forth until we set up a time to play. I arrived on the night and had a few drinks, We chatted and I noticed that the husband kept touchi... Read full Story
rileystar 2020-04-01 19,002 Crossdresser Amateur Group Sex threesome Lingerie domination
100%
My first BBC experience
I stand 5 foot 8 and weigh 138 lbs. With a perky butt, long natural eye lashes, and clear smooth white skin I would always receive comments from women how jealous they were of my features but never did they want to pursue an intimate relationship with me. But I also didnt have much interest in them ... Read full Story
Jenny Hurle 2020-04-29 13,726 Crossdresser Amateur Bareback Creampie Big Cock Ebony self sucking
100%
First intercourse with a man
If you read my previous story, “First time with a man”, I gave my first blowjob. What I didn’t mention at the time, was that I was on my way to work about 2pm in the afternoon, (I worked the swing shift). That afternoon meet up was just to see each other, talk and maybe meet again later. But my e... Read full Story
Mistysis 2020-10-23 7,036 Crossdresser Amateur Bareback
91%
My Vancouver get a way....
I was in a different city, where no one knows me, free. My boi hole started to tingle as soon as I realized I could finally prowl the gay scene of a big city, with two and a half days of zero commitments I had little time to waste. I went to the hotel room in Abbotsford and showered, shaved and trie... Read full Story
badbadboi667 2020-12-14 6,089 Crossdresser Amateur Group Sex Bareback Creampie Blowjob gangbang Ass to Mouth cum in mouth
94%
My first time crossdressing with a man
It was Christmas night 2016 and I had gone out to the bar with a few friends. Came home a little tipsy and very horny! I rushed to my room, took off all my clothes and put on a very sexy, slutty outfit (black lace thong with matching bra, a blue sweater, black mini-skirt, and black knee high boots) ... Read full Story
Betty D 2021-01-18 8,242 first time Crossdresser Amateur Cumshot Fetish Blowjob Mature Homemade mini skirt small cocks black panties obese
96%
Ladyboy surprise in Bankgkok
A few years ago I went to Thailand for the first time, my first stop was the bustling city of Bangkok. I had heard stories about the nightlife, the girls and the tourists. The country had never appealed to me that much but through a twist of fate I ended up visiting the city of sin for a couple of d... Read full Story
Gracemel121 2021-03-25 11,648 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy cum in mouth
100%
The Dating Game
This happened a few years ago when i had just been accepted into Edinburgh University to undertake my Masters. As all students do, I went to the tourist spots with an eye on the other tourists and potential bars to frequent. Having come prepared with an arsenal of dating apps downloaded I was all s... Read full Story
chris1989r 2021-08-11 6,469 Amateur Bareback Big Cock domination Ass to Mouth cum in mouth
100%
Camming Down the Rabbit Hole Ch. 07
Opening my eyes I struggled a little as the residual cum on my face from last night’s show hadn’t been fully wiped off, I felt the dry and crusty leftovers crinkle on my skin, but couldn’t help but smile to myself as I remembered how it had got there. The intensity of that orgasm had been on another... Read full Story
Dani_does_Dallas 2021-10-22 6,156 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
100%
The Golf Bet
A couple of years ago I joined a new golf course, I wasn't the best golfer but very keen, I would be at the practice area almost everyday for at least an hour. Over this time I got to know a number of members and it was a good way of meeting people to play with. Over that year I met a number of new... Read full Story
chris1989r 2022-01-03 4,552 Amateur Cumshot Shemale Fucks Guy Guy Fucks Shemale cum in mouth
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 3,226 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 2,544 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,075 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
100%
First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... Read full Story
AllenB 2022-10-21 4,911 Amateur Big Tits Cumshot Latina Creampie Fetish Blowjob rimming Homemade cum in mouth latina ts
100%
Becoming Sissy
I remember my first true and sober gay sexual encounter. The guy from the party that was my first BJ and first penetration was one of the closest friends of the group. He bought a house up north and 3 of the girls and me went to his house to help paint and work on some things. This was about a mo... Read full Story
xspeeny 2023-04-28 7,449 anal Amateur Bareback Blowjob Big Cock sissy cum in mouth
100%
HE DIDN'T KNOW I WAS TRANS...
I'd worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
mika96 2023-05-11 6,436 anal Amateur Bareback Creampie Blowjob femboy Ass to Mouth
100%
First time.
Long did I contemplate ever meeting a trans gurl to fulfil my darkest desires. Sometimes I would convince myself that it's only a fantasy, other times consumed with the thought, even waking up in the middle of the night with a rock hard erection. My choice was clear. Try it. What do I have to lo... Read full Story
Danshorny 2023-05-11 5,581 anal Amateur
100%
Edging lessons for Hannah
Hannah and I began spending our weekends together. She didn't have a job and I was always free those days so every Friday or Saturday night became sleep over night where we could be two 18 year old sissies, doing each others makeup, playing dress up and sharing our deepest desires. Now that our rela... Read full Story
KaceyKlarissa 2024-01-25 3,587 Crossdresser Amateur Cumshot Masturbation Fetish Big Cock kissing Homemade sissy romantic cum swap edging teen (18+)
100%
Hits, Misses: G
Ok, what follows are some accounts of hookups and almost hookups I've had with transwomen in the late 2000s, early 2010s. Some I think about a lot. Others I've forgotten completely and am attempting to interrogate my memories. Things have changed a lot in the culture, mostly for the better. Visibili... Read full Story
bybaking 2024-02-06 4,436 anal Amateur Cumshot Bareback Big Cock Ebony Guy Fucks Shemale Interracial black Tgirl
80%
My 11 Sex Bucket List and 6 Sexual Habits
My Sex Bucket List : 11 things that I want guys to do for me. 1. Upside Down Deepthroat Balls Deep 2. Blindfolded Gangbang 3. Spitroasting 4. Cum Gargle 5. Anal Creampie Eating 6. Double-sided Dildo Play 7. Double Anal 8. Gay Train 9. Pissing In Asshole 10. Deepthroat with blindfold and ... Read full Story
cdmisato 2024-04-30 2,884 Crossdresser Amateur Asian sissy
73%
Vegas Baby: Swinging for the Fences
"Hello," Miss K said as she answered the phone. "Where are ya? You're gonna be here in 5? Alright. You got the address for IHOP, right? OK, See ya in a bit. Bye." "So is this girlfriend of yours on her way?" Jennifer chimed in. "I mean if she doesn't exist, this... Read full Story
shemale lover 2011-11-15 5,293 anal oral handjob
100%
Unconditional Love Chapter 8
After a two' hour nap, Alison and I awoke and the first thing we did was make our way to the bathroom to freshen up. I started up the hot water and climbed into the shower and' once she finished relieving her bladder Allie climbed in with me under the hot water and we embraced each other. We kiss... Read full Story
shemale lover 2013-02-04 6,160 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 13,754 first time sucking fuck domination
100%
Amatuer Strip Night Chapter 2
Sasha stood in her bra and panties looking nervously out over the crowd at the topless strip club. She shuffled her feet and looked down, her blonde hair covering her face and she wondered to herself if coming back out onto the floor had been a good idea at all. Sasha had just won first place at ... Read full Story
shemale lover 2012-10-21 3,699 Cumshot shemale oral sex cum swallowing
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 8,511 anal Cumshot shemale oral
100%
Reshooting the Scene, Chapter 1
I have been a porn aficionado since I was a teenager. My first dabblings were with Hustler magazine and a *very* hardcore mini-novel called “Her Busted Asshole,” which told the raunchy story of Ginny Cummings’ sexual coming of age. In addition to the very graphic story, it had full color glossy p... Read full Story
Lovelace 2021-06-07 4,366 Bareback threesome Blowjob blonde Big Cock Sex Toys Ass to Mouth
50%
Baby Face Jack's Biggest Fight
The referee held his gloved hand high in the air. The crowd was hushed as the ring announcer spoke, "Ladies and Gentlemen, the winner of this World Featherweight Championship Boxing Match to unify the title, by technical knockout, and still undefeated; Baby-face Jack Mc Coy." The crowd scr... Read full Story
shemale lover 2012-02-08 7,038 fuck oral
100%
Case of the Jealous Transsexual Chapter 1
I met her on a free amateur’s web site. I have to admit that I was not particularly looking for a transsexual at the time. I had posted some naked pictures of myself on the site and had been going through the tons of emails that I had gotten in response when I ran across Dee as she called hers... Read full Story
shemale lover 2012-03-19 2,890 anal sex oral sex kissing
76%
Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
shemale lover 2012-01-30 9,759 Stockings Big Tits fucking foot fetish
100%
A Night Out To Remember
A night out with Liz and Sue I had known Sue for almost five years but had known Liz for a lot longer. We had met while she was still at school although I was four years older we still became good friends. After she left school I helped her with her college work and more importantly when she need... Read full Story
shemale lover 2012-04-20 3,933 Cumshot oral sex crossdressing