Sort by
Relevancy

Free Stories

100%
Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
darrell 2022-04-20 4,352 Group Sex Cumshot Shemale Fucks Guy Blowjob blonde Big Cock Asian Shemale and Girl Sex Toys Mature Ass to Mouth shemale + shemale
100%
Gangbanged By 3 trannys
Gangbanged By 3 trannys This is a story about the night I was Gangbanged by 3 trannys. I was at a Transgender after hours clubs that was filled with hot ass Tgirls. This tall white gorgeous woman was eyeing me the moment I walked in. She was wearing this fitting blue dress that showed off ... Read full Story
My Shemale Attraction 2022-12-11 8,503 Group Sex Shemale Fucks Guy threesome Blowjob gangbang Ass to Mouth cum in mouth
100%
Shopping plus extras!!!
Hi, so as you can probably imagine I buy a lot of underwear and have a few favourite places to shop. My favourite by far is Ann Summers. The range is great and the staff are so helpful . Anyway back to the story. So I decided to go get some new underwear to see in the new year, I got myself up and d... Read full Story
Samantha Jewels 2023-01-06 4,357 Crossdresser Amateur Cumshot Fetish threesome Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Castro - shemale goddes
Nobody would have believed the scene was true, her slender, smooth and tanned legs crossed in such a deliberately provocative way as to reveal a glimpse of crisp white panties. Her tightly fitting, classically styled little black dress cut to ensure firm large breasts were displayed to maximum effec... Read full Story
Law12 2018-03-04 5,067 Masturbation Bareback Creampie Ass to Mouth cum in mouth Supernatural
90%
My Recent Holiday Treat
I've come to accept that I am a bit of a dirty girl sometimes. Most of the time I think that I could easily fall into be labeled a nerdy, quiet goth girl, book worm and not at all up of current trends. A misfit as I was called in high school. But there's another side of me. A side that craves sexual... Read full Story
Gothtransgirl41 2018-12-04 6,606 Group Sex Bareback Big Cock Ass to Mouth cum in mouth shemale + shemale
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,596 Masturbation Blowjob blonde ass fucking big boobs
72%
Wie sich schlagartig mein Sex Leben änderte... Teil 1
ich war nun schon einige Zeit heimlicher Crossdresser. Nie wurde ich von meiner Freundin erwischt, auch wenn es manchmal wirklich knapp war! Ich hatte ein sicheres Versteck für meine schönen Sachen und meine Sextoys und konnte hin und wieder meine geheime Neigung ausleben wenn sie nicht da war.Trotz... Read full Story
Holly Swallow 2019-03-20 7,792 Stockings Small Tits Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob blonde gangbang domination Interracial Sex Toys humiliation Homemade sissy girlfriend chastity cage Ass to Mouth cum in mouth chastity sissy amateur crossdresser fendom
78%
A Little Girl Forever
Since I was a little girl I dressed in my sister's clothes, she knew it and she kept clothes for me and sometimes she bought clothes thinking about me. She was my accomplice and still is. When I was alone I dressed totally as a woman and I felt totally satisfied and realized as such, this included m... Read full Story
Mabel Cecilia 2019-05-06 8,040 Small Tits Crossdresser Amateur Cumshot Latina Masturbation Creampie Blowjob blonde Lingerie Shemale and Girl Guy Fucks Shemale Sex Toys Mature self sucking Solo Shemale cum in mouth double anal shemale + shemale
50%
J'ai enfin goûté la bonne chère/chair
Dépucelée en bon et du forme... Chose jamais osée depuis que je goûte la jouissance par tous les sens et dans tous ses sens... Je la découvris quand elle m'a sourit en guise de remerciement pour lui avoir cédé le passage dans la superette du bled où j'étais pour affaires. Sandales à ses pieds d... Read full Story
hippocampus_171 2022-11-09 1,069 Small Tits Amateur Shemale Fucks Guy Guy Fucks Shemale Mature Homemade Ass to Mouth Vintage cum in mouth
50%
Son fils se fait «punir» par maman
Les parents ont divorcé après que mon père ait été surpris en train de tricher. Après la séparation, j'ai choisi de vivre avec ma mère. Ma mère était très mécontente de la perte de son mari. Elle a commencé à fréquenter des hommes pour avoir des relations sexuelles. Tous les jours, je l'entendais se... Read full Story
Femboy 2021 2023-01-20 4,121 Stockings Crossdresser Fetish Big Cock Lingerie domination Guy Fucks Shemale Mature Ass to Mouth
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,652 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
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 4,424 Stockings Crossdresser Amateur Big Tits threesome Blowjob Big Cock Lingerie domination Guy Fucks Shemale Mature Homemade threesome sex
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 4,686 Amateur Cumshot Shemale Fucks Guy threesome Blowjob Big Cock
50%
Pa-mie sex-agénaire
Luxure frénétique d’une pa-mie sex-agénaire; entre rêve et réalité Je n’avais jamais fantasmé de mec viril, même après avoir offert ma virginité; mais à une fabuleuse sissy. Avant mon Ѐre, mes préférences de fantasmes étaient toujours avec des lui-femme glabres, idem concernant mes relations d’aprè... Read full Story
hippocampus_171 2023-07-09 848 anal Amateur Group Sex Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy Ass to Mouth
100%
Tony to Tanya Part 3
Sarah finished applying make-up to Tony's face. It was mostly subtle, just enough to highlight his eyes and cheeks. The only part that wasn't so subtle was the lipstick; bright red. He was already dressed up in a beautiful black dress that left his back and shoulders exposed and only went down to... Read full Story
shemale lover 2011-12-19 4,559 anal cum oral
44%
First time with a shemale
I must have been 16 back in the day, but I always looked older so it didn't really affect anyone's judgement in the sex world that I had loved since I can remember jerking off for the first time. I was walking the streets of Amsterdam that day, the Red light Disctrict looked like paradise on earth,... Read full Story
shemale lover 2012-02-14 7,160 first time Stockings Small Tits
68%
Shemale Porn Photo On The Wall Of Her Room
She was a truly hot shemale that I’ve been seeing for a couple of months now, from time to time. She had some really big tits and a dick that didn’t really get in our way much. It really wasn’t all about the sex. I loved talking and even cuddling with that girl. We talked about ... Read full Story
shemale lover 2016-06-12 6,519 asshole shemale Big Cock
100%
Threesome goes clubbing
Ft. Lauderdale is probably the most LGBT friendly city on the east coast. So many nice restaurants and clubs that welcome all and have many LGBT employees as well. Lydia and I have been married several months, we had met Joanne an absolute amazing transgender girl during a weekend trip to the Baha... Read full Story
Jon Paul 2021-07-08 5,268 Big Tits Cumshot Bareback Creampie threesome Guy Fucks Shemale cum in mouth
70%
His first anal!
Andrew was a very simple guy. He was not aggressive, very quiet and nice. Actually he was not quarrelsome, just a man of peace. But we all know that still waters run deep. Over the past few years, Andrew had longed for being penetrated. Vehemently. He needed to be bent over something and fucked thor... Read full Story
shemale lover 2014-05-09 8,871 anal shemale jerking off
60%
Teasing BIG BLACK COCKS at truck stops
I'm a white blonde bubble butt Tgirl living in Las Vegas and sometimes I go out and cruise the truck stops on I15 down south to I10. I do it at night and sometimes for a whole weekend in my mini van which has darkened windows. I love to get out of my mini van and walk around the back parking row at ... Read full Story
TgirlJill4BBC 2013-06-03 7,999 Stockings blonde Big Cock cum Lingerie Interracial Latex
71%
TGirl Initiation by 3 BIG BLACK 12
In my teen years I was often told that I was quite feminine.The high school punks always told me that I filled out the back of my jeans in a girly way. After taking a shower one day I did notice that they were right, I had a nice white bubble butt. Not to mention that my lips were also quite girly. ... Read full Story
TgirlJill4BBC 2013-06-04 9,069 Stockings Cumshot suck Big Cock Lingerie Interracial Latex
62%
Bobbys Preggo Shemale Turn
This is a story about how a 14 year old normal guy became a sexy 16 year old pregnant Shemale. It has many similarities to real events. Bobby was a normal guy. he grew up in a good family and was fairly popular. One day when he was in 9th grade his class recieved a new teacher. Her name was... Read full Story
shemale lover 2011-08-18 4,675 Big Tits shemale submissive
100%
Buffy the Shemale Vampire Slayer Part 5
By the time that Buffy arrived at Rupert Giles' apartment, the former librarian, her ex-Watcher, had just finished reading a new volume of what Edgar Allan Poe, in The Raven, had referred to as a "curious and quaint volume of forgotten lore." He'd just settled the large, leather-bound volu... Read full Story
shemale lover 2011-08-19 3,683 hardcore celebrities shemale
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 2012-12-21 118,796 hardcore Cumshot sucking bdsm domination
67%
My SHEMALE MOTHER
I was going upstairs from the shower in a towel and passed my mothers room on the way into mine,my mom said "can you help me with my hair-dryer". Thinking nothing of it I went into her room to see her seductively standing there, staring at me. I just stood there and said "your haird... Read full Story
davecoastx 2015-08-09 28,574 Big Tits suck shemale jerking mom
87%
Threesome for Desi
After months of looking for someone to join us for a threesome, we finally found someone and he is coming over tonight. We are all going to meet at your place so I get over there right after work to get ready. We both take a shower and get dressed before he arrives. We sit on the couch together as w... Read full Story
b0099b 2016-04-27 5,001 anal threesome cd Desi
81%
My Fantacy
I'm sitting here watching porn thinking about how bad I want laid. So, I figured I'd post a quick story of something that's been on my mind lately. See, I'm craving a good dicking. But, not only that. I want to wear my new stockings and garter belt with a black bra, lace thong an... Read full Story
Shiloh Patutie 2017-12-26 3,738 Stockings Group Sex threesome Guy Fucks Shemale Ass to Mouth cum in mouth
100%
New Orleans TS dream come true..
In was on New Orleans running water for the victims of Katrina in 2005. I went down to Bourbon St several times an one night I walked into adult fetish store and as I was looking around there was what appeared to be a very beautiful black woman bending over with a very short skirt on. I was admirin... Read full Story
jim3801 2018-09-11 10,647 Group Sex Bareback Shemale Fucks Guy threesome Big Cock Ebony Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
100%
Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
Regina10 2021-02-22 6,667 Crossdresser Bareback Creampie Fetish Blowjob blonde Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth double anal
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 8,824 anal shemale porno
75%
Super Shemale Tube At The Waiting Line
The restaurant was crowded - everyone in Boston wanted to be there, and I waited for an hour at the bar, hoping to get a table for one. But was I watched my chances of having dinner crumble to dust and glanced at Super Shemale Tube on my phone's browser, a girl sitting next to me asked "Hey, yo... Read full Story
shemale lover 2016-03-14 6,666 anal cum big ass
80%
Black Shemale Videos At Job Interview
Another boring job interview: I had to check endless series of candidates, none of whom were any good. It was just a secretary's position, but all sorts of people came, without having a clue what to do with a computer, pencil or copier. "Next", I yelled nervously, just wanting the day to e... Read full Story
shemale lover 2016-04-10 8,618 anal tranny cum
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 3,846 anal transsexual ass licking
100%
How I Used To Cum On Shemale Webcam
I like being a shemale and doing webcam shows. A lot of guys out there would never admit it, but they really like my sort - best of both worlds, so to say: tits, asses and cocks in one convenient package. And shemale webcam was also a lot of fun - I could play with myself as much as I liked and dude... Read full Story
shemale lover 2011-08-10 2,907 anal shemale cum
100%
Shemale Cam Made Me Explode
I really thought it would be just another quick cam session. I logged on to my computer, chose a girl and started talking. But after a while, she told me she's a shemale - then I realized I'm in the shemale cam section. I replied that it's ok - hell, I'm all about trying new things and broadening ho... Read full Story
shemale lover 2011-08-11 3,018 Big Tits cum fingering
100%
Sucking hard and good
I was never one of those transvestite porn fans or MTF & drag queen sex lovers. I much prefer sinking my teeth into kinky transgender personals or simply find myself a busty tgirl to love, hold and perform the best heshe fucking ever. So that's exactly what I did last night. I went to one of ... Read full Story
shemale lover 2012-03-26 2,790 Big Tits blonde oral sex large penis
33%
Superstar fun - an evening to remember!
Starting with a little history, let me say that I started getting into tranny fun back around 1990. I went on a visit to New York and had always been an avid reader of Screw magazine/ newspaper. Before the Internet was in full-bloom it was distributed nationally to all cities around the country and ... Read full Story
shemale lover 2012-04-03 3,048 anal sex cum ass licking oral sex 69 position
100%
1st time with Thai shemale
So after months of crosssdressing , camming and phone sex i finally decided to have a meet. I found a lovely Thai shemale on birchplace and went to see her in London. She was gorgeous and put me at ease straight away. After a few minutes of massage she started licking and sucking my nipples, then as... Read full Story
Nutcracker29 2013-04-09 9,265 first time suck Shemale Fucks Guy Asian big boobs
50%
It’s been to long
It’s been 3 weeks sense I had my boy pussy fucked. I normally get to see my boyfriend when my girlfriend is at work but we are both working from him now. I can’t even dress up in clothes and play with my self. I swear I’m about to go crazy. Luckily my boyfriend is my girlfriend child hood frown so h... Read full Story
Wet boy kitty 2021-02-01 2,364 Crossdresser Amateur Big Tits blonde cum in mouth
100%
Surprise Ending (Part One)
My wife is the picture of professionalism from 8 to 5, but after hours she is a sexual dynamo who loves men and women. Throughout our relationship she has introduced several of her gal pals into our bedroom, hot tub, shower, etc...you get the idea. Anyway, two weeks ago she let me know that one o... Read full Story
Chantel13 2022-08-23 5,469 Crossdresser Amateur Group Sex Outdoor Bareback Shemale Fucks Guy threesome Big Cock Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth
92%
All The Transexual Stories Came To Life
I’ve spent my adolescent years reading the transexual stories whenever I could. I had a long process of self analysis trying to figure out if I were gay or not, so I wanted to find a shemale who could be my first and see if I even like being fucked or sucking a dick. Thanks to the sex personal... Read full Story
shemale lover 2016-02-12 5,990 suck shemale ass licking
69%
Shemale Dating
We arrived late in our hotel room. The date was going well... but I didn't know what to expect, being new in shemale dating - I was excited and a little scared at the same time. She was a beautiful Latina: busty, dark exotic skin, fantastic lips; we couldn't stop kissing each other in the elevator. ... Read full Story
shemale lover 2017-02-12 12,758 anal sex suck deep penetration
89%
Father-In-Law Shemale Adventure
My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last momen... Read full Story
shemale lover 2012-07-04 7,406 shemale oral facial facefucking
100%
Blossoming Shemale
My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to prove it now, and to be honest, I didn't really have the desire. That was all before. I have to ... Read full Story
shemale lover 2012-08-01 5,019 Cumshot shemale Big Cock oral sex
100%
Bi male and anal sex
Thru out my adult sex life I have always enjoyed having my ass teased and played with. Then I started dating a woman whom loved to tease a mans ass with her fingers, yes fingers where she quickly got me use to taking 2 of her fingers. Then one night things changed. After a hot night of wild sex,... Read full Story
shemale lover 2012-10-10 5,364 anal sex cum jerking fingering
100%
Male or Shemale, Still a Slut
Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... Read full Story
shemale lover 2012-12-20 9,319 Cumshot sucking blonde ass fucking Guy Fucks Shemale
93%
Proud To Be A Sissy Chapter 7
"You're being really dirty little sissy slut today," daddy chuckled and asked, "What's gotten into you?" "Making up for the last few days I guess," I giggled hugging him tightly, "and I missed you too." "I missed my little sissy too." He repl... Read full Story
shemale lover 2012-12-24 7,608 Crossdresser Cumshot Blowjob Big Cock ass fucking
97%
Never Wanted To Be Your Girlfriend Ch. 02
So, after being made up like a slut, left glued to a pair of silicon breast forms, and caught sucking-off my best friend, I was pretty sure my day couldn't get any worse, but I had come nowhere near the end of my torment, as Michelle now had something else planned that I was probably not going to li... Read full Story
shemale lover 2014-07-21 9,492 hardcore Cumshot suck Lingerie ass fucking
57%
Sucking cock, a curiosity. Part 1
I've been a straight man since forever. I've also been into sex and porn since I was young. And my fetishes always involved tits and big asses. Any kind of tit play turned me on. Still does. When I was 14, I saw a porno and watched tittyfucking for the first time. It turned me on so much, ... Read full Story
bigdickthug 2017-05-22 5,104 Fetish Big Cock Sex Toys
94%
My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
SachinJoy 2018-10-04 32,631 Cumshot Shemale Fucks Guy Blowjob Big Cock Ladyboy cum in mouth
87%
TO BE OR NOT TO BE – PART 1
TO BE OR NOT TO BE – PART 1 by Spanky de Bautumn This is a story about how taking a play to New York City changed people's lives. A transgender coming of age story. I was born Harold Stanley Dayes, not a great name for a kid growing up. I know my parents loved me, but Harold was my mom's dad a... Read full Story
SpankydeBautumn 2021-02-22 3,865 Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob Ladyboy Lingerie Shemale and Girl cum in mouth
100%
Being taught a lesson .......... I think!
How did I end up on my back in my own bed, legs straight up with my ankles over her shoulders, ready to have my ass fucked from a lost bet? A bet that Alma clearly cheated at as we discover. I was off to Thailand for a 16 week course in Thai massage at a school recommended highly by a friend I ha... Read full Story
Curious_billy 2023-11-12 8,253 anal Amateur Group Sex Bareback Creampie Shemale Fucks Guy threesome Big Cock domination Homemade Vintage cum in mouth
100%
The Big Tiddy Goth Girl
Hannah and I went to the pool in my apartment complex. This was my first time dressed as female in public and I was loving my new, feminine tan lines. To keep a long story short, while tanning we were perv'd on and approached by a guy calling himself Mark. He was desperate for our attention and fumb... Read full Story
KaceyKlarissa 2024-02-23 4,837 Crossdresser Big Tits Cumshot Masturbation threesome Big Cock Shemale and Girl small cock big ass sissy femboy cum on tits goth
0%
The orgy with a shemale
I had to move to Japan back in the fall of 2004 and lived in Tokyo in a 3 room apartment.I could not pay all of the rent so I lived with a female school teacher age 27 years of age and japanese.Her name was Miki.There was a one more girl who was friends with Miki ,I never seen much of her.Her name w... Read full Story
shemale lover 2011-08-29 5,181 Big Tits asshole Big Cock
100%
Desiree and Big John
It had been only a week since I'd introduced "Desiree, the Hot to Trot Transvestite" to my girlfriend Suzie, leaving me not a bit surprised that she chose not to spend the very next weekend at my place. While she hadn't freaked out, she was concerned I was gay since I was so convincing but... Read full Story
shemale lover 2012-08-20 4,470 first time anal sex transvestite cum swallowing
78%
Anal Therapy
My new psychiatrist wasn't at all what I expected. When I saw her name in the phone book, I pictured a dowdy old lady wearing a long, gray skirt and flat-soled shoes. What else could Dr. Edith Doss look like? I got my answer when a tall, leggy redhead stepped into the waiting room. A tight, black... Read full Story
shemale lover 2012-11-24 7,729 anal Fetish cum crossdressing