Sort by
Relevancy

Free Stories

75%
Ashley Simone Part 2
Thanks for all the letters of support and interest in my encounters with Ashley. The first story is on the nifty archive and was dated just a few days ago. As I stated in the first one, these encounters with a remarkable shemale are completely true and are not embellished. I received many ema... Read full Story
shemale lover 2011-10-23 3,403 Group Sex Masturbation oral sex
70%
Trans Sexual Clinic 04
It was some six weeks since Johnny had attended the clinic with Wendy and now he found himself wanting to go there more and more. He could not get DR. Francine out of his mind, he desperately wanted to have her hard cock in him again as he fantasized about leaning forward and sucking on her delectab... Read full Story
shemale lover 2012-04-12 4,080 Group Sex Sex Toys
100%
Steve to Stephanie Chapter 1
This is my first attempt at a longer story with deeper characters and a more evolved story line. Stay tuned for the next chapter. As always comments are welcome. * Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve... Read full Story
shemale lover 2013-01-29 4,055 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Dottie's Back Chapter 2
After tossing my purse onto the kitchen counter, I nearly ran across the backyard toward Kim's house. Stopping a few feet short of the fence, I kicked my heels over it, pausing to be sure they landed in Kim's yard. On a previous occasion, one of my heels flew into the yard next to Kim's. This forced... Read full Story
shemale lover 2013-01-29 3,335 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
58%
Janet Owns Me Now Chapter 5
It was a beautiful summer's day, perfect beach weather. i packed a light lunch and a bottle of chardonnay in the cooler and we headed for the closest beach, about a forty minute drive away. J. Looked beautiful in Her black two-piece bathing suit and floral silky wrap, Her hand light and warm on my l... Read full Story
shemale lover 2013-01-30 3,819 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
60%
Ass Whore Laurie, Double Penetrated
Ok, its Friday evening. My C List ad is finally published, "Ass Whore 4 MMM Tops" and waiting....waiting for some horney guys eager to pump up a hot sissy cock whore and willing to be in a group! Lot's of responses (my pics never fail!) but only singles looking for a one on one. So, I... Read full Story
Chasis88 2014-03-27 4,253 Crossdresser hardcore Big Cock ass fucking dp
69%
Catching Up with A Former T-Gurlfriend
I was jogging one Saturday morning at well known West L A park. I was jogging kind of fast almost sprinting when I came up on woman jogging slower than me. I almost ran into her as I was running. She moved out of my way I slowed down and apologized for being rude. That's when I realized she was a fo... Read full Story
Brett1 2018-08-06 4,590 Latina Shemale Fucks Guy Blowjob cum in mouth
94%
My First Time Made Me A Slut
A true story of my first time. And why I so need a daddy now. The first time I went out dressed. I went to a bookstore in east Portland. As I got out of my car feeling the breeze up under my very short silky skirt, trying to pull it down as cars were wizzing by. I walked or should I say wobbled the... Read full Story
Teddie 2018-09-12 12,883 first time Stockings Crossdresser Bareback Blowjob blonde Big Cock gangbang domination Guy Fucks Shemale slut cum in mouth
88%
Making love on the beach
= First = My name is Lely Bella Calistia, I'm an Asian shemale, I'm 27 years old, and I now live on a very beautiful island in Southeast Asia, I have only been here for 2 years and have a nice new life. I have a friend when I was a child, and we are good friends until now, but unfortunately wh... Read full Story
Bella Calis 2018-10-22 6,418 Blowjob Asian gangbang Guy Fucks Shemale
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,730 Big Tits Cumshot Masturbation Uniform Frottage
100%
Masturbation fantasies 2: Looking for Amanda
Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... Read full Story
ThatEroticWriter 2019-07-24 9,140 Big Tits Cumshot Masturbation threesome Frottage
100%
Sports Bar Pre-drink
Sitting on the chair leaning against the bar, Steven sat quietly sipping on his rum and coke. It was a fairly quiet night at the local sports bar he often ventured to after work to wind down from his work shift. Steven looked up at the door as a small group of women walked through laughing and ta... Read full Story
Master VeeJay 2019-09-27 9,680 Big Tits Blowjob Asian Guy Fucks Shemale
100%
Weekend Fantasy
have so many fantasies....the one that gets me lately, is having access to a house out in the middle of nowhere, for a week or weekend, where i can dress up, all day. No one knows of my lustful secret....so the idea of being able to stay this way without thought, gets me so hard and such in the moo... Read full Story
martley 2020-07-20 5,424 solo Amateur Group Sex Masturbation Big Cock Lingerie domination Sex Toys Homemade self sucking cum in mouth double anal shemale + shemale
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,909 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
100%
Shawshan part2
The summer weather has finally let up and cool evenings where you need a sweater are among my favorite times of the year. Charlene left now from prison and served her time for drug possession. We had become close friends as well as cellmates over the last few months. She no longer cuts her hair as ... Read full Story
Jon Paul 2021-05-20 3,520 Latina Masturbation Bareback Shemale Fucks Guy threesome Guy Fucks Shemale shemale + shemale
77%
im a cd slut
i started dressing about four years ago and i love it. it turns me on to see the guys watching me. to know that they are thinking about fucking me. i loved it. so i called a friend that i knew was gay and we couldnt wait to get together. it was on. i was invited to his house for drinks and a dip i... Read full Story
jenny green 2022-06-17 8,070 Crossdresser Bareback Lingerie Guy Fucks Shemale Mature
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 5,159 Cumshot Outdoor Creampie Fetish Blowjob Big Cock Ebony Guy Fucks Shemale public bbc massive
50%
FILLE DE RÊVE ⚧️ ⚧️
« Alors, à quoi ressemblerait ta petite amie parfaite ? » « Toi », pensa Steph, regardant dans les yeux noisette avec des reflets dorés à l'intérieur. Il lui fallut quelques secondes pour se rendre compte qu'il devait répondre avec sa bouche. « Oh, euh… quelqu'un d'attention... Read full Story
Femboy 2021 2023-03-18 1,025 Stockings Crossdresser Fetish Guy Fucks Shemale Interracial cum in mouth
100%
Groped on the Bus!
In real life I do not crossdress in public, I am not yet comfortable being my true transgirl self, I wear normal men's clothes and I look like a guy. So I look very different from my persona here. So...there I was standing among dozens of strangers at a bus stop. I kept looking up from my phone ... Read full Story
Chrissy Tunnell 2023-03-22 5,427 Small Tits Masturbation Fetish Big Cock Ladyboy Guy Fucks Shemale Frottage
100%
PRIS AVEC DES CONSÉQUENCES ⚧️ ⚧️
Je m'appelle Stephen et je suis étudiant diplômé à l'école de commerce locale. Je suis à mon travail depuis moins d'un an et, en tant que nouveau venu au bureau, je pensais que faire des heures supplémentaires ferait bonne impression sur mon patron. Eh bien, j'ai certainement fait une impression, ma... Read full Story
Femboy 2021 2023-03-24 1,111 Stockings anal sex Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth feminisation forcé attrapé
83%
Trans Daughter F*cks Daddy
This is true story. I am 50 age n avid shemale , Transgender, ladyboy lover. Two years back i was member of LGBTQIA community in Pune where i met this ladyboy trans girl . We spoke, chat sone time and immediately clicked. She said she lost her father and wanna me to be her daddy. I agreed and i ac... Read full Story
Stud4Shemale 2023-09-28 7,799 shemale Ladyboy transgender india Pune Shemale Fuck Man Man fuck Shemale trans daughter LGBTQIA father daughter fuck shemake cum popular shemale story best shemale porn
100%
Vegas Encounter- part Deux
Tuesday morning, it’s early and dark. Jack is in an Air BnB home in Summerlin, a suburb of Las Vegas. He met an online friend Diane and her friend/roommate last evening and we all slept in the King-size bed. I look around, Diane is sleeping curled in a ball on her side, but Holli is not here. M... Read full Story
Jon Paul 2023-12-22 5,723 anal Stockings Cumshot Bareback Asian Guy Fucks Shemale
50%
KING OF TRANNY CHASERS ENTRY 1
IT WAS AROUND 1AM AND MY GIRL FRIEND GINA AND I ARE GOING AT IT.HER NAKED BODY WAS HANGING OFF THE BED IN DOGGY.HER BIG CARAMEL ASS CHEEKS JIGGLED AS A POUNDED FROM BEHIND. SHE WAS SCREAMING "YES BABY" AND MOANING NON STOP..AS BEAUTIFUL AS SHE LOOKED AND HOW AMAZING HER BACK SHOTS WERE LOOKING..W... Read full Story
Ghostface drillah 2024-07-02 2,893 Amateur Big Tits Masturbation Big Cock Ebony Guy Fucks Shemale big ass Homemade Ass to Mouth cum in mouth
85%
My Erotic Free Shemale Porn Movies Sex Scene In The Air
My job as an airline stewardess always keeps me on the move. The fact that I am a shemale limits me to hanging out with a certain group whenever I go to certain cities. Well, one particular night flight, there was a handsome man that pinched me on my ass as I walked by. Normally, I would complain... Read full Story
shemale lover 2015-12-11 9,103 anal shemale porno
69%
From Mob to Shemale
Two years ago, I was a member of the Ciccio family in Chicago. I wasn't very high up in the organization, because I wasn't Italian. I had made my way up through the ranks, however, and was making a pretty good living. I had everything I wanted, got all the girls I wanted, and did just about ... Read full Story
shemale lover 2011-10-29 10,748 orgasm facial oral sex
81%
First time shemale encounter
Lets start off by saying this a very true story, one that i love to re-live over and over. lets begin I was in el paso, texas..my girlfriend at the hotel. Something in me decided to go to the strip club. So i did. After a few dances, i decided to leave. I had always heard in mexico it was very ea... Read full Story
iloveshemales112 2011-12-17 9,822 Latina Bareback Shemale Fucks Guy Big Cock
58%
Preggo Scat Sex
Sara was horny. For any type of sex. She was stuck on a bus heading to her school. After 14 years of wasting her time She discovered her own sexual abilities.She had her first practice by fucking her brother's friend. She didn't come to school to learn. She came to screw anyone in sight. She had ... Read full Story
shemale lover 2012-01-07 12,324 Masturbation lesbian peeing
100%
Emily and Steve Part 9
Over the next few weeks things really started to settle in at work. Emily was being more than accepted, she was being lauded. Emily, feeling much more comfortable as a woman, started being a much better worker. The quality of work that Emily was producing was far superior to Mike's work. She was fea... Read full Story
shemale lover 2012-04-07 3,007 anal sex Group Sex blonde oral sex
92%
End of a great thing
So in an earlier story I told all of you about I guy I literally ran into when I was trying on lingerie and it turned into my first sexually with a man. So we had a great time for several months. One night he called me over and we had our usual sexual adventure. After we were done he told me tha... Read full Story
Play1802 2014-03-27 4,117 hardcore Group Sex Cumshot suck ass fucking Interracial riding cock cd
50%
Urges
I've been having Urges to Get Fucked. The thought of a Dick in my mouth gets me so Hard... I masturbate to Sissy videos at least 2wice a week; I'll laydown on the bathroom floor to spread my legs to finger misf while I stroke my Cock w/ my right hand. Sometimes I wish there was a Strong... Read full Story
Ray Vegas 2017-07-25 5,273 solo shemale gangbang black cumming 69
96%
A Night of Lust
I was out at a night club with a few friends, and we were there for for a while before I noticed this sexy, rather short girl across from me at the bar looking over. I could tell, even from this distance that there was something special about her, I wasn’t sure what that was quite yet though. The mo... Read full Story
JessicaEdwards 2018-08-07 18,668 Stockings Amateur Cumshot Masturbation Bareback Creampie Shemale Fucks Guy Blowjob blonde Big Cock Lingerie deepthroating Guy Fucks Shemale cum swallowing deep throat deep penetration cum swapping pov Ass to Mouth cum in mouth anal fuck sloppy virgin ass
100%
Threesome fun
We had invited friend over who has big cock --he arrived and we sat around for awhile talking about sexual encounters of the past --I'm a bi part time shemale cross dresser who is very kinky --anyway it got around to looking around the house and as it happened we stopped in the bedroom , and all o... Read full Story
goodgurl34 2019-01-08 4,698 Stockings Crossdresser Amateur Big Tits threesome Blowjob Big Cock Lingerie domination Guy Fucks Shemale Mature Homemade threesome sex
100%
Liberty in Lisbon Part 2
So here I was walking down the Av da Liberdade feeling very pleased with myself. I had just thoroughly enjoyed an experience I thought would only ever be in my dreams and, the best part, there was more to come [cum]. In fact I found myself humming the 59th Street Bridge Song. Life I love you feeling... Read full Story
Rusty12 2019-07-31 5,159 Amateur Masturbation Bareback Creampie Shemale Fucks Guy cumming
66%
Laufhaus Besuch bei Wunderschöner Tranny
Hallo, heute möchte ich von meinen zweiten Besuch bei einer Tranny berichten, das erste mal war leider nicht so toll wie das zweite mal, vielleicht schreibe ich ein anderes mal darüber. Ich war in Graz bei einem Laufhaus bei TS Stefanie, über sie habe ich in einem Forum nur gutes gehört und habe ... Read full Story
johnschmit 2019-10-24 8,035 Big Tits Shemale Fucks Guy Blowjob Guy Fucks Shemale cum in mouth
66%
I love Shemales
Ever since I was 13 I have had a thing for shemales. I had always wanted yo experience sex with a shemale. So when I was 20 I decided to get on an escort site and find a sexy Tranny. I ran across the perfect one so I immediately booked a date with her. So the dreamday finally came and I was so excit... Read full Story
Weinerboy6969 2020-01-29 9,497 Creampie Shemale Fucks Guy cum in mouth
100%
Liberty in Lisbon Part 3
After Olivia had so perfectly taken my anal virginity, we laid in bed cuddling, touching, kissing and her cum leaking from me. I had not been so lovingly caressed for such a long time. It was just perfect. She asked me how I was feeling. I think I said before that I don’t do deep and meaningful very... Read full Story
Rusty12 2020-09-16 3,620 Masturbation Shemale Fucks Guy Blowjob old-and-young 69 sucking
100%
Sissy Slut and Stepdads part 2
My mother kicked Frankie out and swore that he was the last loser she would ever date. She believed that we were still having sex, and she was right. Pure raw animal lust drove us, and It was even better when we sneaked and got. That nervous adrenaline mixed with my passion and made me super horny a... Read full Story
Regina10 2021-02-15 4,396 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to 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 2,757 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
Dominated sissy goodgurl34
Mmmm ty Sir Deitrich --I'm standing in your open doorway wearing black latex stockings and garter and some hott red lace panties over top -I have a black corset on and a very sheer dress on ,wig and gurl mask ---my wrists are cuffed to a circle hook one on each side of the doorway door jam about 6... Read full Story
goodgurl34 2022-03-15 2,598 Crossdresser threesome redhead domination Guy Fucks Shemale Sex Toys Homemade shemale + shemale
100%
Amy and the Straight Jocks PT1
Only a couple close friends knew for sure and most others knew it as just a rumor. Amy dressed and lived life as a girl like she had since the start of high school when she moved from a new town. The jocks would laugh and whisper to each other when she walked by debating if the rumors were true. Co... Read full Story
DADDY4sluts 2022-08-09 4,087 Teen (18+) Cumshot Bareback Creampie Blowjob Guy Fucks Shemale cum in mouth
100%
Mommy, can I be your fuck-toy?
I saw my step-mom taking a shower by accident or so I thought. It was not until I saw her pretty big she-cock jus hanging there between her sexy well defined legs. It was even hard & it was already as big as my cock when its hard. It looked so big that it was a bit scary yet some muscle in my anus s... Read full Story
Curious_billy 2022-11-22 7,569 Amateur Cumshot Masturbation Bareback Shemale Fucks Guy Blowjob Big Cock Lingerie Mature Homemade Ass to Mouth cum in mouth seduction
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 4,914 anal first time Big Cock fantasy Surprise
50%
"SISSIFIED": 12 JOURS DE SISSY-MAS
JOUR 1: mardi 25 C'était le matin de Noël quand j'ai entendu frapper à ma porte, ce qui était, bien sûr, très étrange à dix heures du matin. À midi, j'allais chez ma famille pour Noël, et j'avais rarement des visiteurs inattendus. Toujours dans ma robe, je me dirigeai vers la porte et fus s... Read full Story
Femboy 2021 2023-01-20 1,591 Stockings Crossdresser Amateur Fetish Blowjob Big Cock Lingerie domination Sex Toys cum in mouth
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 5,734 anal Amateur Group Sex Cumshot Fetish Big Cock Lingerie big ass Homemade femboy shemale fucks shemale cum in mouth
100%
Dogging in the Park
The last two nights have been great fun in our local park. There is a parking lot where guys gather after dark and I was one of them. Both nights I was dressed up as a slutty CD with a black bra, fake silicone tits, black pantyhose and a short miniskirt. First Night: After waiting about an hour a... Read full Story
Rocky8844 2024-04-02 4,499 Crossdresser Outdoor Blowjob
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 3,927 Crossdresser Big Tits Bareback Blowjob Big Cock Ebony Guy Fucks Shemale big ass femboy cum in mouth
50%
Rassemblement d'alumni pas comme les autres;
Un rassemblement d'alumni pas comme les autres; 'Mer/Sable/Soleil' et pourquoi pas 'Sex' dans un club de vancance; nous nous sommes rassemblés pour fêter les 40 ans de notre 1ère rencontre en fac. La seule règle était de venir sans compagne pour revivre nos jours de 'frosh'. avec les ca... Read full Story
hippocampus_171 2024-06-13 314 anal Amateur Masturbation Sex Toys Mature small cock big ass Ass to Mouth cum in mouth
95%
Once a Slut Always a Slut
I held my breath – and then I knew I had crossed a line – I had become by my submission, in that instant of time, another individual. I had known Paul Phillips since I had arrived at the local school in the village some 6 years before. We had moved on together to the grammar school in... Read full Story
shemale lover 2015-06-17 12,182 first time shemales Group Sex
0%
Mike and Chris Together
Mike's sex life had taken a definite series of turns for the worse. When he called one of his favorite partners, Stella, she apologized for not returning his earlier calls, and told him she had been very busy lately. "I'm really sorry, Mike. I've had some great times with you, and I will alw... Read full Story
shemale lover 2012-02-07 5,415 anal sex Creampie Shemale Fucks Guy Guy Fucks Shemale
100%
My surprise Part 2
I managed to force myself free. I slammed my back against the cubicle door and I looked into her eyes. She was beautiful, amazing eyes, great face, nice pair of tits and a great body. She stood up, pulled her tights thong and skirt up and calmly walked by me touching my crotch and winking at the sam... Read full Story
shemale lover 2012-02-21 2,367 hardcore oral sex Guy Fucks Shemale
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 11,482 Group Sex Masturbation shemale Ebony facial
100%
Boi Toy
They met me off the train late in the afternoon. Their welcome was warm and friendly. I was exhausted from travelling and spent the evening in wonder as we first had drinks with friends of theirs at one home then all went out to eat at a restaurant, then back to another friends home for more drinks.... Read full Story
shemale lover 2013-01-29 6,205 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
96%
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 2014-11-25 10,405 tranny suck Creampie Shemale Fucks Guy ass fucking 69
80%
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 2014-12-03 6,694 tranny suck Creampie Shemale Fucks Guy ass fucking 69
91%
A little office fun
Two days had passed since Scott’s amazing night with Louise. He hadn’t heard from her at all but today he was finally going to see her again at work. He was nervous and excited all at the same time. Scott proceeded to his work desk and worked his day as usual. He hadn’t seen Louise at all throughou... Read full Story
Master VeeJay 2018-01-04 4,897 Big Tits Masturbation Blowjob Guy Fucks Shemale
78%
3 day I became a satisfy of men's desires
My name is Lely Bella Calistia, I'm an asian shemale and I'm an entrepreneur and I have a side job as a singer at some cafes. At that time my friend asked me to be a singer in the wedding, and the place is very far 4 hours journey, and when morning I immediately headed to the airport, t... Read full Story
Bella Calis 2018-06-26 8,801 Amateur Big Cock Asian gangbang Guy Fucks Shemale cum in mouth