Sort by
Relevancy

Free Stories

100%
Uncle sweet Lover
Uncle Barney called me this morning and wanted me to keep my evening free. He wanted to meet me at the motel with a surprise for me. I was so excited and could hardly wait. I had to decide on something to wear, but when I thought about it, I realized that I wanted to wear something special. He would... Read full Story
Regina10 2024-02-19 5,086 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
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 5,535 anal Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Lingerie Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
100%
KING OF TRANNY CHASERS ENTRY 2
LAST YEAR TO CELEBRATE MY BIRTHDAY I DECIDED TO FULFILL ONE OF MY SEXUAL FANTASITES. I HAD BEEN WITH 2 CIS WOMEN SEVERAL TIMES BUT NEVER HAD I BEEN WITH 2 TRANNIES. MY BIRTHDAY WAS ON A FRIDAY SO I SPENT THAT DAY AND THE NEXT CELEBRATING WITH MY FAMILY AND GINA..THAT SUNDAY I SET UP AND PLANNE... Read full Story
Ghostface drillah 2024-07-04 3,042 anal Amateur Group Sex Big Tits Cumshot Shemale Fucks Guy Fetish Big Cock Guy Fucks Shemale big ass Homemade Ass to Mouth shemale fucks shemale
50%
sine qua non: anal/vaginal pleasure
One thing's for sure, my desire is to be fucked and to fuck... And it's in this order of things that I've been wanting to fulfil my fantasies for the last two years. I'm not too fussy about choosing my partners, but luck has always smiled on me when it comes to finding the right one. However, over t... Read full Story
hippocampus_171 2024-04-05 3,830 anal solo Amateur Mature big ass sissy femboy
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 5,566 tranny suck Big Cock ass fucking dp precum
100%
Towel Boi: You're Hired
Kasey Stevens woke up in his new studio apartment. The five-foot-nine, blue-eyed sissy with ash brown hair yawned and stretched before heading into the bathroom. He showered, taking good care to lather his rosy skin with strawberry scented body wash. He shaved his legs and rinsed off. Then, he appli... Read full Story
Faggyboi and Puzziboi 2023-11-14 6,292 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
100%
Police House Call
My heart was beating a mile a minute when I heard the knock on my door. I was hoping that it might be Beau, or Larry, or if I’m lucky it would be Tom Cobb. He asked me to call him Tommy. I had been thinking about him recently. Bo and I had banged the night before, but I was as horny as ever. Larry w... Read full Story
Regina10 2024-04-19 3,829 Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Guy Fucks Shemale big ass femboy cum in mouth
100%
I had park sex with three HUNG black guys after dark !
So last night, I had sex with three black guys at a park last night as of writing today. This happened at midnight. But, let’s reverse and start from the beginning…. I left my house because I was feeling a little frisky and if anyone knows what sniffles app is , if you know , ..you know! So a hot sp... Read full Story
Ezra_Kyle25 2024-08-18 2,599 anal Crossdresser Cumshot Bareback Blowjob Big Cock Ebony domination Guy Fucks Shemale big ass femboy Ass to Mouth cum in mouth
100%
The Seductive Seed of a Tranny MILF
The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... Read full Story
Gwapo67 2022-05-03 8,094 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
delicious virile male flesh
Tasted delicious virile male flesh… The breeze caressed my swollen nipples giving me pleasant shivers. The two glasses of Riesling had also contributed to my excitement. My crotch was burning as if the disappearing sun had blown all its thermal energy into me. Under my fine lace panties, purple o... Read full Story
hippocampus_171 2023-04-23 5,189 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
90%
Tranny Fuck
Its about midnight, and I'm horny a fuck. Couldn't find one of my late night freaks to come over and milk the cow, so i headed over to the east side to see what was going on at the strip club. As I get off on the exit, there's this long road that leads to the strip clubs. Its dark, on this side of t... Read full Story
shemale lover 2013-07-18 6,039 anal sex Blowjob ass licking 69 balls licking
100%
Couple and a Tranny
There is a saying that a single man looking for companionship and good fortune will seek someone for marriage. Lydia and I met several months ago on an online dating site. We agreed to meet at a bar restaurant for drinks and initial meeting. She was at the bar wearing a yellow sundress, white painte... Read full Story
Jon Paul 2022-09-20 5,554 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
57%
story of Jojo
Some find it confusing of who i am or what i am, including me. i found some kind of definition: femboy A young boy who presents extensive feminine mannerisms and actions often blurring the line between a boy and a girl. Can be confused with a cross dresser, but it usually refers to boys at v... Read full Story
jojo58654 2017-09-12 10,986 Amateur transvestite strapon cd femboy
83%
Fun with a latina tranny
So I'm a big fan of a big tranny cock in my ass. Just throwing that out there early on here. So this past summer I decided that with my school being off I should get some tranny cock as fast as I could. I went on a site and set up a new account, hoping for the same luck I had a few months ago wit... Read full Story
shemale lover 2012-09-15 3,797 anal Latina cum oral Sex Toys strapon
90%
First Outdoor Fuck
Sat in my office with nothing to do was making me tired there was no customers to serve which was slowly driving me mad, what was worse was the hot weather outside which always makes me horny, knowing I had all my girly clothes in the boot of my car was making my cock twitch in my cheap nylon work t... Read full Story
shemale lover 2012-12-19 6,455 Crossdresser Outdoor ass fucking pantyhose heels
100%
Oneness with the bodies
many years went into just fantasizing being with shemales. I was getting hornier day by day to try it out. But being in a relationship there was hardly any room or time for it. I once experienced it in bangkok and confirmed that I really can do it and actually love it. One day suddenly it was br... Read full Story
zyankhaan786 2023-05-30 6,636 Group Sex Bareback Shemale Fucks Guy Big Cock domination big ass cum in mouth double anal
80%
Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
shemale lover 2012-06-24 5,573 big dick tranny anal sex Cumshot orgy facial oral sex
100%
A Series of Perverse Dreams, Part 1
My relationship with Hannah had always been mutual in the idea that neither one of us was ever truly the dominant one. It was an equal, balanced relationship of mutual fucking and sucking. However, I had REALLY enjoyed being made into a submissive sissy slut by Nikki. Something changed in me after o... Read full Story
KaceyKlarissa 2024-02-24 5,843 anal Small Tits Crossdresser Group Sex Big Tits Outdoor Big Cock gangbang domination sissy femboy Ass to Mouth cum in mouth
50%
Being Shemale
Every night I wear make up and dress up in a sexy lingerie. I stand in my balcony late night trying to lure men and women driving on the road. Last night a truck driver stopped near my house to inspect his vehicle. During his inspection he suddenly saw a long legged booty women in the balcony inf... Read full Story
babydriver 2024-06-04 3,718 Stockings Crossdresser solo Outdoor Ebony Asian Ladyboy Lingerie big ass sissy femboy
80%
The Farm
“See you Sunday, baby,” said Marcus Jenkins to his wife, Tasha. “Alright! Have a good day at work,” the wireless phone company retail store manager smiled. “Love you, Kobe! Love you, Tiara,” the wastewater plant operator said to his offspring. “Love you, too, daddy,” the youngsters rang out in un... Read full Story
Faggyboi and Puzziboi 2021-12-08 5,820 Teen (18+) gangbang Guy Fucks Shemale sissy femboy Ass to Mouth
81%
Tranny G's all Tranny Gang Bang
Chris had finally returned after a year overseas. During his leave he flew out to Phoenix and we would spend a few days in Las Vegas. We drove four hours and checked into the hotel. A year apart and we ripped our clothes off and fucked hard. We took a short nap and went for an early dinner. I told C... Read full Story
shemale lover 2013-03-05 7,857 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
90%
Riverbank Tranny Fucktoy
Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river. It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site. I had been chattin... Read full Story
shemale lover 2014-12-03 4,863 tranny hardcore suck Big Cock cum ass fucking deep throat
100%
My first Tranny
After a recent breakup and a few years of fascination I finally got the urge to post a M4T wanted add on craigslist. After several unwanted offers from old men I was finally send pictures and the number of a sexy Latin shemale named Ana. After exchanging text messages for about 15 minutes I was fres... Read full Story
cubanpapi305 2015-05-13 7,349 first time anal sex rimming 69 riding cock
73%
My first experience with a tranny
ENGLISH: I want to tell you about my first sexual experience with a transsexual in 2018. I was a bit drunk and got horny, I searched the internet and found a brunette tranny with 7 inches of cock, wavy hair, young and attractive. She had an HIV negative health card. We went to the motel and I was... Read full Story
cuchillo 2020-08-28 7,620 Amateur Cumshot Latina Shemale Fucks Guy Blowjob Big Cock Lingerie cum in mouth brunette ts fingers cocksuck
100%
My first time having sex with a Tranny
I have been obsessed with Trannies for as long as I can remember. There is something about a gorgeous feminine woman with a big thick cock that drives me crazy! I turns me on so much that I kept pushing myself further with my love for Trans women. I bought sexy dresses, underwear and heels to wear s... Read full Story
Joe22lovests 2021-09-15 12,103 first time Shemale Fucks Guy Blowjob Big Cock
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 5,598 anal Amateur Group Sex Cumshot Fetish Big Cock Lingerie big ass Homemade femboy shemale fucks shemale cum in mouth
20%
Extend Sissy
Extend pls! https://sissy.fun/sissy-bimbo-whre-mayatsarina-chained-up-big-butt-tranny-wth-toy-in-asshole/ , https://xxxposed.fun/prostitute-fucktoy-slave-bimbo-mayatsarina-for-rent-cheap/ , and also this https://xxxposed.fun/dumb-bimbo-whore-may... Read full Story
MayaTsarina Bimbo 2024-03-14 8,527 big ass sissy femboy Exposed Sissy exposed
50%
The BIG COCK that I will eat.
ENGLISH: Hello friends. In the link below, you can see the tranny cock that will fuck me in the days to come. I saw her advertised on the internet, I picked up the phone and called, I will see her when her clinical tests are negative for sexually transmitted diseases, because I will surely swallow... Read full Story
cuchillo 2020-09-18 7,943 Amateur Cumshot Latina Shemale Fucks Guy Blowjob Big Cock Homemade cum in mouth brunette ts swallow cum
100%
Dream Bride Tranny
My niece Avril and I rushed along the ground floor corridor of the hotel and made sure none of our relatives were watching us as we disappeared into the room. Inside, we were met by Miss Anne of the Kinky Brides Group, who immediately ordered Avril to strip me naked. "Please, not today,&q... Read full Story
shemale lover 2012-11-13 5,711 anal cum oral Lingerie
81%
That night....
I was extremely nervous when I pulled out my phone and dialed the number. Never before, in my wildest dreams, had I thought I would act on one of my strongest fantasies. I knew I would be nervous when I first met her, but after exchanging pictures and seeing that big, fat cock of hers, I knew I ha... Read full Story
bigTHICKY 2017-05-08 9,548 Big Tits Cumshot Latina Big Cock Ladyboy cum in mouth
50%
Towel Boi: Heading to Work
“Goddamn, white boi! You got the best fuckin’ ass,” declared the father of two. His steel manly form perspired as he moved hard into the bottom. “Look at all that butt shake! Twerk it for me, baby boi!” “Yes, sir,” cooed Kasey, gyrating rhythmically. “Hell yeah! It’s like fucking two big ol’ ma... Read full Story
Faggyboi and Puzziboi 2023-11-17 6,344 anal Crossdresser Bareback Creampie Blowjob gangbang Lingerie Guy Fucks Shemale Interracial sissy femboy bbc
100%
Playfull Sexy Shemale LindaTgirl
The overwhelming passion will start. When you date me... it will all start with kisses and wrapping with my legs around your body and showing of her gorgeous smal tits.The, while sitting on your lap I will whisper in your about what will be next.. About what turns me on... about sucking, licking,... Read full Story
TS-Linda. 2022-02-21 2,680 Small Tits Amateur shemale Lingerie escort money latina ass PAWG Pawg Tranny lindatgirl
100%
My addiction to anal orgasm,
My addiction to anal orgasm, I love feeling the sensual contact of my corset and my nightie on my skin. In front of the wall mirror in my bedroom, I take suggestive poses to arouse my desire during my lingerie fittings. Feeling vaguely like a woman, I lower my last barrier of chastity by sl... Read full Story
sandratvtg 2024-07-02 2,938 anal solo Fetish Lingerie femboy chastity cage rosebud GodeXXL
100%
Crossdresser 1st time!
Hi, im new to this. this happened about 3 years ago now. I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from th... Read full Story
shemale lover 2013-05-30 8,079 Outdoor Big Cock fingering ass licking virgin public cd piss
100%
I got anal creampied at the beach!
As soon as we got onto shore, I knew it was the perfect place. The hot sun was beating down on us and my body was tense with anticipation. Finally, we were going to be alone out in the wilderness with nobody around and could enjoy each other thoroughly. My hunky date and his monster cock were going ... Read full Story
Madison Heights 2022-12-01 5,046 Cumshot Outdoor Creampie Fetish Blowjob Big Cock Ebony Guy Fucks Shemale public bbc massive
100%
The switch
HI have been married for 12 years now. Trim and dapper, this 35-year-old's marriage was satisfactory enough and I played the role of husband well. Sex with the wife was still good, with both making out at least once a week or on rare occasions, once monthly. Twelve years on in this heterosexual rela... Read full Story
shemale lover 2014-10-11 8,619 anal shemale jerk off
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 11,750 Outdoor Big Cock bj Shemale on Guy self fuck
81%
Tranny Porno Tube Surprise Party
“Is that some tranny porno tube on your computer?” my roommate asked, catching me once again in action. “NO!” I replied and added “You should really learn how to knock!” I was simply mad because he caught once more. I was about to move in with my girlfriend the... Read full Story
shemale lover 2016-05-18 11,154 anal sex asshole cum
100%
Dirty Tranny Bitch
I was feeling really horny, massive nervous anticipation. I was all dressed up, looking for my first taste of cock. My name's Nikki, I was aged about 25 or 26 at the time, only 2/3 years ago, but I was fed up being the `closet' tranny tart, I wanted to try out some cock; in short, I wanted dirty ... Read full Story
shemale lover 2012-05-01 3,688 Stockings anal sex Cumshot oral sex finger fucking
100%
Totally dominated
I was out walking one night, a walk i used to make with my girlfriend. We had just broken up a few days ago. I don't know why I was walking here again, the memories weren't good ones. She had cheated on me with my best friend. Anyways, I was walking this familiar path through the city streets when I... Read full Story
shemale lover 2012-10-27 5,883 anal Group Sex Cumshot Creampie Big Cock oral
93%
Dominated
I was out walking one night, a walk i used to make with my girlfriend. We had just broken up a few days ago. I don't know why I was walking here again, the memories weren't good ones. She had cheated on me with my best friend. Anyways, I was walking this familiar path through the city streets when I... Read full Story
shemale lover 2012-11-12 6,986 anal tranny Creampie oral
88%
My first time as a Femboy CD pt 2
David ordered me to dance for him and I hurriedly got off the floor and walked over to the radio and turned it on. I changed the station from an alternative rock station to a top 40 one, which was better for dancing. After I selected the station I moved to the center of the room and started to dan... Read full Story
Nicole_femboyCD 2014-12-03 21,345 anal Crossdresser Cumshot Blowjob rimming cd
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,912 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
100%
Joanna the Tranny Prostitute
Joanna stood on the street corner and casually shifted her posture from one leg to the other. So far it had been a quiet evening for her with few punters around. Not many girls were plying the streets either. She’d had one customer earlier. He had been an Asian guy in a Toyota who’d stop... Read full Story
Joannacd1 2011-11-07 4,487 tranny Crossdresser Ebony
77%
How I Became a Tranny Whore Part 2
After my first night working for Mama T, I was hooked. At least once a week I was a worthless whore at her trailer. I would be at her trailer, ready to serve her cliental. Of course most the Johns picked one of the real girls over me, but there were the occasional guys that wanted some thing differe... Read full Story
shemale lover 2011-11-08 4,467 tranny suck asshole
100%
The tranny from work
I've always had a thing about trannies. Just something. Never sure what or why. I loved looking at them. Seeing their huge tits. Their nice asses. Then seeing a dick between their legs. Now I'm not gay but, was always interseted. I would look up escorts here in town just to see how far I would go. F... Read full Story
shemale lover 2011-11-24 3,904 anal first time shemales
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 7,884 first time hardcore anal sex Cumshot oral sex crossdressing
100%
Slut bi cross dresser
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 ... Read full Story
shemale lover 2012-11-24 4,750 anal first time cd
88%
First Time Outdoor Festival Fantasy
Fantasy Setting: Summer time in the mountains of Colorado the perfect bluebird weekend we all dream of. The day before an underground rave in the mountains all my friends bail on the show and was now left with either not going or going solo. Well I deiced what the hell and I'll go solo an... Read full Story
xaviergc8 2016-10-26 9,762 anal first time shemale gangbang bondage outdoors fuck toy
100%
Surrendering to Submission
Once, sometimes twice per week, I'd meet my Daddy at that same cheap motel where he'd use me like a doll. On those days, my asspussy would twitch and tingle in anticipation, so much that I had to keep a butt plug in to provide myself enough stimulation. I'd have to force myself from breaking out one... Read full Story
KaceyKlarissa 2024-10-03 668 anal Crossdresser Big Tits Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale big ass sissy femboy daddy
100%
Amy The Tranny Part 1
I met Amy at an adult theatre in town. She was dressed to nines in a mini skirt, tight halter top, and pumps leading up a pair of fishnet clad legs. I invited her into a private booth and once inside, went over her price for some adult fun. She told me I couldn't fuck her as she was on her per... Read full Story
shemale lover 2011-12-14 4,948 shemales hardcore anal sex Big Cock
100%
The Tranny Shocker
Tammy, my step daughter and I had not seen each other for a while and she called me suggesting that we meet for a drink. Naturally, I agreed. She suggested a gay bar near her home and we agreed that 7pm would be good. Tammy is a lesbian who is in a relationship with a beautiful, tall, sexy blond ... Read full Story
shemale lover 2012-04-23 3,691 anal sex Cumshot oral sex cum swallowing
66%
First Gay Experience
Me and a buddy decided to go see a rock concert at the Great Western Forum (that's what the Staples Center was called back then). I was 21 at the time, horny all the time and could never get enough pussy. So we go to the concert in our own cars since his brother lived nearby and he was going ther... Read full Story
shemale lover 2012-08-11 4,836 tranny anal sex Ebony fingering oral sex
93%
My first tranny
I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look i... Read full Story
shemale lover 2012-10-09 7,169 first time anal sex fingering rimming
88%
The first tranny I looked for
So i've had some tranny experience unwittingly. I respond to this ad on craigslist from this 19 year old tranny who lives fairly far away, but her picture was so sexy I decided to take the hour drive. So I drive to her parents house, nervous the whole way, when I get there I get out of the car. Ston... Read full Story
shemale lover 2012-11-04 3,114 anal sex Creampie little ass
100%
How I Became a Tranny Whore
When I was 30 with children at home I would get dressed in the bedroom. When it was time to leave the wife would take the children off for ice cream and as soon as they were out of the drive way I would head for my car. Of course when I returned home the children would be a sleep. The plan worked fo... Read full Story
shemale lover 2011-11-07 4,766 anal Cumshot cum swallowing