Sort by
Relevancy

Free Stories

85%
The sissy dreams
Everyday I wake up in a state , halfway between a happy sissy and a closeted white boy. My mind is constantly trapped in that state. Suffering in silence, the people in my life seem to be oblivious to it, I have it well hid. 48 years of fist fights and weed, long hair and leather coats, Oilfield job... Read full Story
badbadboi667 2021-01-04 6,031 Crossdresser Amateur Group Sex Outdoor Bareback Creampie Blowjob Big Cock gangbang domination Homemade Ass to Mouth cum in mouth
84%
Meeting and Eating Sammi
Meeting and eating Sammi I was the new guy in town. I frequented a local bar/restaurant and noticed a happy group of folks were there quite often. I guess I was noticed too when a VERY attractive young lady approached me and said "Hi. New in town?". We spoke for a while and I noticed that ... Read full Story
GirlyArms 2021-01-22 3,243 Fetish Blowjob handjob skinny surprise dick
77%
Amber part 2
After the night with Hollywood the next day seemed to drag by. As soon as I got back to my room, I quickly stripped. Falling back onto my bed, I slowly masturbated, my mind still reeling from last night. I'd actually sucked cock, not only that, but I liked it, I liked it a lot, and wanted to do ... Read full Story
ambersissy 2021-04-23 3,939 Crossdresser Amateur Blowjob Big Cock Guy Fucks Shemale Interracial
100%
From accidental trans porn addiction to a cum filled booty
One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... Read full Story
CDJaneBooty 2022-04-01 10,930 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
0%
Giving my first blowjob
I was recalling the first time that I ever gave a blow job while I was jerking off last night. I thought I would tell you the story and share what my experience was like when I finally took the plunge and made my first attempts at having sex with a man. At the time, it was a little awkward, but the ... Read full Story
SissyAnalPrincess 2021-05-11 5,305 Amateur Blowjob Danni Cherie
100%
Finally, a Vacation!!
My life has changed so much in the last 2 decades! When I discovered the existence of the trans gender, I was so excited that my life changed immeasurably for the better. I knew what I liked better than anything else. From not knowing trans folks existed, I went to running into them all the time. ... Read full Story
GirlyArms 2021-05-20 3,860 Blowjob trans skinny small dicks sexy arms
75%
Stoping by the Adult Video Store.
Has anyone been ever stopped at an adult video store. That a rhetorical question, I know the answer. The first time I visited an adult video store, I was in for the shock of me life. Just like any inquisitive twenty yr old, I thought the establishment sold adults videos. It never dawned on my about ... Read full Story
lkusex 2021-05-28 5,296 Blowjob self sucking Ass to Mouth
100%
The four of us
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-08-02 4,706 Group Sex Big Tits Cumshot Bareback Creampie Blowjob Big Cock Guy Fucks Shemale Ass to Mouth
100%
White Dress
It had been a busy week and come Sunday afternoon after a softball game I was craving a cold beer, a couple of my teammates decided to tag along and go to a bar. Once getting there the drinking started and by the time they closes down we still wanted to keep going. There a was a place that open a... Read full Story
Rominaxnxx 2021-10-08 3,325 anal first time tranny Blowjob Lingerie dress throat
100%
The Game 2
That next morning again Ada and I went down for breakfast and the table was smaller, It wasn't as grand as it had once been and to every guy at the table was now at least two girls. We had our normal breakfast and for once there seemed to be a little more chat between everyone, I think after bei... Read full Story
chris1989r 2022-01-24 5,014 Amateur Cumshot Bareback Shemale Fucks Guy Blowjob blonde Big Cock Asian domination Guy Fucks Shemale Ass to Mouth cum in mouth shemale + shemale
91%
The Girl Next Door Ch. 03
derezzed Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Ale... Read full Story
Gwapo67 2022-05-13 6,518 Bareback Creampie Shemale Fucks Guy threesome Blowjob cum in mouth
87%
Southern Hospitality Ch. 03
XtinaSmith2017 Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned ... Read full Story
Gwapo67 2022-05-16 5,240 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
100%
Tight Spot
XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... Read full Story
Gwapo67 2022-07-22 6,386 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
100%
Whoops, I fucked my bosses son! Real story, written by a tgirl
Normally I never would have entertained the idea of sleeping with a co-worker but when I saw my boss’s son for the first time, that idea quickly went out the window. It wasn't like I didn't think about fucking my co-workers, I did… in fact, I would leave work some days leaking with precum from the v... Read full Story
Madison Heights 2022-10-27 7,530 Bareback Blowjob shemale Big Cock Uniform Lingerie tgirl office sex cum in mouth coworker creampied workplace
100%
Birthday Blowjob
I have a large amount of straight admirer’s who love to watch me do my thing, and I occasionally get a request to do something on camera that they have asked for ( ask away by the way ask away) personally. Well this one’s a bit different as he wanted me to go to him and do it……….. You and I know th... Read full Story
Samantha Jewels 2022-12-11 3,672 Crossdresser Blowjob cum in mouth
66%
The colossus and me
The colossus and me... step by step towards completion (1) When my phone rang I was watching the World’s news in TV, only tragedies. It was Lina (cf. my previous story) on the phone. The colossus with an angel heart and an elephant dick. She was in my town for business. And without her saying ano... Read full Story
hippocampus_171 2023-03-07 5,778 Amateur Cumshot Creampie Blowjob Big Cock Mature Homemade Ass to Mouth cum in mouth
100%
I met a guy in the nightclub and I didn't tell him 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
Madison Heights 2023-03-25 7,347 Cumshot Outdoor Blowjob Big Cock cum in mouth club outfit Surprise Cock Partying surprised
100%
The Twink and the Bear
He stood there, slowly rubbing his hardened cock in the confines of the public toilet cubicle, trousers around his ankles, his legs adorned in black nylon stockings, held in place by the straps of his delicately laced suspender belt. It was so naughty to be playing with himself in a public place, wi... Read full Story
Daddybear71 2023-03-28 4,873 Crossdresser Blowjob Big Cock Mature 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 7,211 anal Amateur Bareback Creampie Blowjob femboy Ass to Mouth
100%
Mein erster Blowjob
Nun hat es endlich mal geklappt. Ich schrieb längere Zeit mit einer anderen Sissy und lernten uns immer besser kennen. Nach mehreren vergeblichen Versuchen sich mal live zu treffen, hat es dann endlich geklappt. Wir trafen uns auf einem Parkplatz. Ich hatte bereits einen heißen String, Strapse und e... Read full Story
Maja 2023-07-04 1,943 Stockings Small Tits Crossdresser Amateur Outdoor Blowjob Big Cock Lingerie Homemade sissy
87%
Me and my Trans friend have a threesome with a Tgirl
I was with my trans friend and we went over to her other trans friend's house and I met her for the very first time. We were hanging out and having a few drinks. She asked us what music do I like and I said metal. She plays Disturbed and Rammstein on her stereo system. Then she started playing with ... Read full Story
Miss Steek 2023-10-09 6,588 anal sex Masturbation threesome Blowjob music drinks Cumming twice Social visit Forplay
100%
How could I forget my first time .......
"Ok, ok, ok stop. No more. It hurts a bit" I said. "Just relax your ass baby. Push out like you have to go poo", my date said. How did I end up like this? A straight A college student, a devout Christian with a nice gf like me ends up in bed with this sexy woman ...... Ok wait, I thought she wa... Read full Story
Curious_billy 2023-10-29 9,785 anal Amateur Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Big Cock domination Homemade cum in mouth teen (18+)
100%
Fucked By BBC pt 2
It has been 3 weeks since I became a bbc cocksucker, since then I have learned to enjoy the taste and the feeling of a cock in my mouth. I have also learned the guys name on the 2nd day of being used by the guy, his name is Darren. One day while I was at Darren's giving him a blowjob he tells me ... Read full Story
kinkyguy18 2023-11-03 7,193 Group Sex Bareback Creampie Blowjob Interracial sissy Ass to Mouth cum in mouth
75%
My First Blowjob As A CD
My experience with giving a BJ to a friend in need all started when a buddy of mine was going through a divorce . We got together a few times and got drunk and he was feeling down in the dumps and very sad . the one time he told me the worst part of it all was he wasn't getting any sex anymore and t... Read full Story
Rocky8844 2023-11-13 7,773 Crossdresser Blowjob pantyhose sissy cum in mouth
100%
A true first time.
I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... Read full Story
Gtaaddict3 2023-11-21 10,022 first time cock suck Blowjob shemale Big Cock trans oral fantasy virgin escort big first time
100%
Leticia, a Shemale hooker in Berlin
Last week I was in Berlin again on business and wanted to take a look at what the capital has to offer. My interest immediately fell on Leticia. She answered my phone call right away and answered in English. As we agreed for an hour later. Tariff customary in the industry, 150 for 30 plus 50 for cum... Read full Story
Bigpruegel69 2023-12-12 6,796 Cumshot Creampie Blowjob cum in mouth
100%
Fucked by Dany Suad and sucked her off
I'm just back from Glasgow and finally had the chance to make an appointment with Dany Suad. I always found her wide hips, voluptuous thighs, her hot ass in combination with the strong cock extremely attractive. Her face is also very pretty. I booked an hour with a cumshot. She was wearing sexy unde... Read full Story
Bigpruegel69 2024-02-23 8,746 Amateur Cumshot Masturbation Creampie Shemale Fucks Guy Blowjob cum in mouth
100%
Escorted
Hello! Would it be possible to have you send an escort over? A beautiful escort. Not a plain looking woman but someone special, ok? .... Ok, got it. Thanks. I opened my door to a very very sexy woman. Dressed in a tight short dress that hugged her hips and accented her nice size titties. A very bea... Read full Story
Curious_billy 2024-03-13 6,720 anal Amateur Bareback Creampie Shemale Fucks Guy Blowjob Homemade
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 4,033 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
100%
Becoming a Chrissy - Chapter 1
I always knew I was a little sissy slut. When I was ten, I took a pair of my mommy’s panties to try on. It was a hot pink G-string that my petite mother must have worn when she was ready to get fucked by my daddy. It was just the right size to cover my prepubescent clitty and also stretch through my... Read full Story
mindlessrobot45 2024-05-13 4,796 Crossdresser Blowjob blonde femboy cum in mouth
100%
Pati - THE BIRTH OF A SLUT
I'm going with you and your friends to a large clothing store. I'm here as a boy, but we're going to the women's section. Full of beautiful dresses, panties... I can't take my eyes off it. She would like to have it all. We walk among the hangers and you and your friends choose clothes and underwear... Read full Story
patisx 2024-07-04 3,591 Blowjob tranny slut Tranny Whore turned into slut pati innocent slut pati slut pigtails whore patisx shy tranny for cash
100%
I was backstage giving blowjobs at a transsexual beauty pageant
I was backstage giving blowjobs at a transsexual beauty pageant I had this neighbor, who cross-dressers on weekends for a LGBT club. She invited me to an annual transsexual beauty pageant. Beautiful slutty shemales competing to be the official beauty queen for the club. She happens to be hosti... Read full Story
My Shemale Attraction 2024-08-07 4,449 Crossdresser Group Sex Big Tits Cumshot Blowjob blonde Big Cock Ebony gangbang domination pantyhose
85%
cruising park blowjob in the moonlight
Back in the early 2000's I was really having this lust for sucking cock. I would come home from work, watch porn, stroke, cum and then a few hours later I would want the real thing. So I searched the internet and found a site called "squirt". On this site they tell you where all the cruising plac... Read full Story
likesboth 2024-10-08 1,532 Cumshot Blowjob Big Cock
100%
My first cock sucking experience Black CD/Transsex
My first drunk TS/CD experience. True story It was the early 90's. I lived in LA and had not much going on in my life in terms of a sex life. I had ventured into straight porn and when I dared to, at the video store I would sneek in a shemale video here and there. I would find the scenes ... Read full Story
likesboth 2024-10-11 2,235 Crossdresser Amateur Blowjob Big Cock Ebony
100%
My first Escort girl
I was in my early thirties. I had just out of a relationship that ended very brutally. I was hurt for several years as I took it difficult. It was at this time, already having had my first sexual experience with a Crossdresser/Ts when drunk and still thinking of that experience that I decide... Read full Story
likesboth 2024-11-05 2,121 anal Cumshot Blowjob Big Cock Asian Frottage femboy
58%
Manual Sissificar a tu Novio
MANUAL DE LA ESPOSA Y NOVIA PARA SISSIFICAR A SU HOMBRE, DESCUBRIRLE SU LADO SUMISO Y CONVERTIRLO EN CORNUDO Y MARICÓN por MARINATVFEM Todo el proceso es una batalla psicológica que tienes que ganar siempre. Mantén la calma y no levantes sospechas. Entrénalo día a día con humillaciones continua... Read full Story
Marinatvfem 2017-09-25 22,237 Crossdresser Amateur Fetish Lingerie
100%
De drogas, sexo y otros placeres (Primera parte)
-Tienes 30 minutos para ponerte coqueta y bonita. Te espero en el cuarto, así que no te tardes mucho preciosa porque tú y yo la vamos a pasar sabroso ¿Oíste? Tras decir esto Felipe cerró la puerta en mis narices dejándome a solas en la oscuridad de su baño. De inmediato eche seguro a la perilla en... Read full Story
johan3092 2021-07-08 2,844 Crossdresser sissy putita nena convertido
100%
Luna parte 1 “Como me convertí en travesti”
Las aventuras de Luna. Parte 1 “Como me convertí en travesti” ¡Hola a todos! Soy Luna, una travesti de closet. Me encantan leer relatos eróticos de transexuales, mis favoritos son las transformaciones por parte de una novia/amiga/esposa, y pues como he leído tantos relatos y actualmen... Read full Story
Sofia Luna 2021-09-06 2,835 Crossdresser sissy crossdresser
100%
Mi amigo Alex
Poco antes de empezar a ir a la escuela me mude con familia a uno de esos barrios con todos los edificios iguales, había una gran cantidad de chicos de mi edad así que no me importo en absoluto. Cada tarde después de volver de la escuela salía a jugar o lo que sea y con el tiempo por alguna razón,... Read full Story
SR-D 2021-02-26 3,925 first time crossdresser lingerie
100%
La heredera 5. Fin de la herencia
Ultimo capitulo de esta serie en la que mi jefa, la hija de los dueños de mi empresa, me hizo descubrir un apasionante mundo y terminé en su casa haciendo el papel de su mujercita. Version para imprimir - Esto lo has preparado tu? -pregunté a Pepa- Esta buenisimo. - No, a mi lo de cocinar como ... Read full Story
Jmtv1996 2023-09-08 1,782 Shemale Fucks Guy
100%
Bunnie & Moonie – ¡Mi novia descubre que soy travesti y pasiva!
Hola a tod@s, soy Luna. Y estoy muy emocionada de contarles cómo cambió mi relación con mi chica desde que le confesé mi más grande secreto: ¡Me gusta ser una nena en la intimidad! Antes que nada, me presento, soy Luna, un chico que le gusta vestir de nena desde muy peque; soy muy delgada, de pie... Read full Story
Sofia Luna 2019-07-08 3,404 Crossdresser Shemale and Girl
100%
Bunnie & Moonie – ¡Mi novia descubre que soy travesti y pasiva!
Hola a tod@s, soy Luna. Y estoy muy emocionada de contarles cómo cambió mi relación con mi chica desde que le confesé mi más grande secreto: ¡Me gusta ser una nena en la intimidad! Antes que nada, me presento, soy Luna, un chico que le gusta vestir de nena desde muy peque; soy muy delgada, de pie... Read full Story
Sofia Luna 2019-07-08 3,483 Crossdresser Masturbation Shemale and Girl
100%
Mi primera experiencia anal
Les voy a contar una historia muy excitante de mi vida Soy un chico muy curioso desde temprana edad, desde que tenía 9 años jugaba con mis primos a las escondidas por las noches o a las carreras y bueno ya saben cómo todo niño siempre busca conocer y saber cosas y sentir cosas, pues un día Estaba j... Read full Story
Bigdick1689 2024-10-03 830 anal Amateur Cumshot Big Cock Homemade pov
100%
2 Traileros
Una noche buscaba divertime con alguien y publique un anuncio donde buscaba a un hombre mayor que me hiciera su putita y le gustara verme vestida. A los 20 minutos un hombre me envio un mensaje diciendome que es camionero y estaria esa noche en la ciudad. Eso me exito mucho y le pregunte donde podri... Read full Story
chz 2018-10-17 5,261 Crossdresser Amateur Group Sex Cumshot Bareback Creampie threesome domination Ass to Mouth cum in mouth
100%
La heredera 1
Hace realmente poco tiempo que entre en la empresa en la que estoy, como unos cuatro meses. Desde que entre me han deparado multiples y agradables sorpresas. Les cuento lo que me ocurrio con mi jefa, que era nada mas y nada menos que la heredera de la empresa. Hasta hace poco el trabajo habia tra... Read full Story
Jmtv1996 2023-09-07 1,536 Shemale Fucks Guy
100%
Mi aventura brasileña
Por obligaciones profesionales viajo con frecuencia a Brasil, donde la empresa donde trabajo esta construyendo una importante infraestructura marina. En algunas ocasiones cuando terminamos la jornada salimos a cenar algunos compañeros y habitualmente nos hace de cicerone Joao, un joven ingeniero bra... Read full Story
Carly Sand 2020-08-24 3,166 Group Sex Big Cock Guy Fucks Shemale
100%
la storia di Sara
Erano alcune settimane che ciattavo con Sara, una trans bolognese conosciuta per caso in internet. Di Sara ho visto solo il bel viso molto femminile con lunghi capelli biondi ed il suo meraviglioso seno. Una sera stavamo parlando e lei mi disse " alcuni mesi fa mi sono rifatta il seno, ho conosciut... Read full Story
Sissy Mari 2022-03-22 3,023 Crossdresser Amateur Cumshot cum Ladyboy Lingerie Sex Toys Homemade shemale + shemale sissy crossdresser siisy slut
100%
El nacimiento de una niña
Hola les relato parte de mi vida de cómo comencé a ser mujer espero les guste. Recuerdo que cuando yo tenia unos 6 años mi hermana y una prima estaban en el cuarto platicando y pintándose y midiéndose ropa lo cual para mi verlas asi no fue del otro mundo lo que me llamo la atención fue que decian q... Read full Story
Diegote222 2022-12-13 1,645 Stockings Small Tits Crossdresser Fetish Lingerie Homemade
60%
The Creators: Book One by
Chapter One: The Life Giver BRANDON My twin sister is dead, but she’s not gone. Death is a tragedy in the remote village of Towerhead, but it’s not a rarity. Farming accidents, disease, famine, natural disasters, you name it, it kills people in Towerhead. So, six years ago, when the oxen-pul... Read full Story
sagga 2018-09-18 30,886 Teen (18+)
100%
La heredera 3
Si habéis leí­do los relatos anteriores sabréis que tras una fiesta de la empresa me lié con la hija del director y ya en su cama me enteré de que tení­a una sorpresa entre las piernas. Tras pasar parte del fin de semana con ella llegaba el lunes y nos verí­amos en el trabajo. Version para imprimir... Read full Story
Jmtv1996 2023-09-08 1,537 Shemale Fucks Guy
100%
La heredera 4 (penúltimo)
Esta historia es continuación de las tres anteriores del mismo titulo. A modo de resumen decir que me lie con la hija del dueño de le empresa que resulto tener una sorpresa entre sus piernas. Version para imprimir Esta historia es continuación de las tres anteriores del mismo titulo. A modo de res... Read full Story
Jmtv1996 2023-09-08 1,236 Shemale Fucks Guy
85%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 120,130 hardcore Cumshot sucking bdsm domination
58%
La Señora de la casa te la va a meter todita
Tras mi estancia en varias ciudades y, aunque tengo mi grupo de amigas, a veces necesito desconectar. Para ello suelo perderme durante una o varias semanas por casas aisladas, de turismo rural en su mayoría. Siempre busco casitas con encanto, para disfrutar de mi retiro como es debido...con pisci... Read full Story
IdoiaBoom 2016-01-25 7,094 tranny Amateur shemale fuck ass fuck guy ass
86%
Marido grosero pero bien follado
Mxxxxa es una de mis amigas de mayor confianza, Ella es algo gipi en lo que a sus pensamientos, si bien nunca ha llamado la atención en su forma de vestir, peinarse, etc.... Ha sido siempre liberal y a pesar de tener un carácter marcado nunca ha exagerado o formado escándalos en público y demás. ... Read full Story
IdoiaBoom 2016-01-25 6,402 tranny Amateur shemale ass fucking fuck guy fuck ass
100%
Parcheggio Tir (ITA)
10/7/2016 Era una domenica sera,ed avendo poi il lunedi' libero,avevo deciso di farmi un'uscita serale,a caccia di cazzi che vogliano divertirsi. Cosi' mi ritrovo alle dieci e mezza di sera apoggiata al cofano della mia auto,a fumarmi una sigaretta annoiata. Il parcheggio di cami... Read full Story
JennySissyTG 2017-05-15 3,201 Crossdresser Outdoor threesome
50%
Sissy Amante de la Lencería
HOMBRE AMANTE DE LA LENCERÍA marinatvfem@yahoo.es Tengo 60 años y estoy casado. Llevo muchos años usando ropa interior femenina. Me encanta la sensación del nylon sedoso en mi cuerpo. También duermo con un largo camisón de satén todas las noches. Me siento muy cómodo llevando mi lencería femenin... Read full Story
Marinatvfem 2019-04-01 3,837 Crossdresser Lingerie Frottage