Sort by
Relevancy

Free Stories

50%
Transgender Art: A Sampler
It's not often that transgender art offers viewers a glimpse of a female-to-male transsexual. Usually, the transformation is in the other direction, with the loss of the vagina in favor of male genitals and the acquisition of female breasts. However, one image does reverse this trend, showing a fema... Read full Story
shemale lover 2011-09-06 3,664 shemale transsexual transgender
100%
Karen, My School Teacher Part 2
Just Staying a bit By FoxyHosed “Don't mention it. Now let me start on the pasta with meatballs!” She stood up from her chair “And besides, it will be nice to have someone to eat with, for a change!” She went to the kitchen to start dinner. “Make yourself feel at home!” I watched some TV ... Read full Story
FoxyHosed 2021-02-01 11,305 Crossdresser Fetish pantyhose Mature pantyhose cd
50%
Not your usual birthday present
So here we go again “Happy Birthday” to me, at 51 it’s not that great really it’s just a reminder your getting older!! Anyway here I am 51 having an absolute ball and fulfilling my wildest dreams, Justina likes being out of the closest and loooooves cock.. So for her birthday she hopes someone has ... Read full Story
Samantha Jewels 2022-01-12 2,882 Stockings Crossdresser Amateur Blowjob Big Cock gangbang Lingerie domination Sex Toys Mature cum in mouth
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 4,299 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
100%
Lady In The House Ch. 06
A story by MicheleNylons (Michele continues to be used by prison inmates.) From Part V Harry leant over me and kissed me full on the lips. "That was worth every penny; you are one hot nurse," he laughed. Harry grabbed a handful of my clean white skirt and wiped his cock on it. The silver... Read full Story
✘Transensual✘ 2019-02-25 3,834 Crossdresser domination prisoner prison sex Prison Bitch
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,724 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
50%
A meeting in the dining room
I sat in a boring dining room and ate a mediocre lunch in an even more boring hotel. The only thing that brightened the boredom was when a woman, ripe as a noble wine, entered. The skirt that barely hid her shapely nylon legs was perhaps a bit short, but otherwise it was a lady standing in front of ... Read full Story
Dussinvara 2024-07-15 2,247 anal Crossdresser Guy Fucks Shemale pantyhose Mature
90%
Young Crossdress, Meets His Daddy
Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very ... Read full Story
shemale lover 2012-08-17 4,613 anal Crossdresser Cumshot Fetish oral domination
72%
ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
SpankydeBautumn 2021-01-29 11,502 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 5,218 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
100%
Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
Beryl 2023-12-12 7,406 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
80%
fuck by my best friend's family
= Part 1. Alice's father = My name is Onikky 28-year-old Shemale from ASIAN, this story only shares the first experience of making love. The story begins when I first moved to a big city, looking for a new atmosphere, I don't have a place to live that I know is only my friend's name Alice who ... Read full Story
Onikky 2019-06-25 9,556 Amateur Masturbation Big Cock Asian Ladyboy gangbang Lingerie domination Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
87%
JoHannas Trainingsprogramm
Hallo Freunde, ich bin JoHanna Satin, eine Satin Bitch und Hobbyhure. Leider war ich die letzten Monate aus krankheitsbedingten Gründen nicht als JoHanna aktiv. Jetzt kann ich wieder JoHanna sein ! Ich will wieder als Hobby Nutte auf Tour gehen und Schwänze blasen ! Ich beginne meine Outfits zu sort... Read full Story
JoHannaSatin 2019-10-21 5,632 Crossdresser Amateur Group Sex Big Tits Cumshot Bareback Fetish Big Cock gangbang domination Guy Fucks Shemale Mature cum in mouth
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,743 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
100%
Mike der Pfleger
Mike der Pfleger Vorwort: Es handelt sich hierbei um meine allererste 'Sexgeschichte' die ich schreibe. Meine Schreibkunst befindet sich gelinde gesagt auf Amateurniveau. Die Geschichte ist frei erfunden und entspringt rein aus meinem perversen Gedankengut. Ganz nach dem Motto: 'Geschmäcker si... Read full Story
baileyjay69 2024-08-26 215 anal Crossdresser Amateur Blowjob Big Cock Mature sissy femboy
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 3,519 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
100%
My Noisy Upstairs Neighbors
So... I just moved into my new apartment a few weeks ago, and ever since then all day every day I have been hearing loud noises from my upstairs neighbors. Not just normal walking-around noise, but loud and heavy bangs, crashes, and poundings against the floor, my ceiling. Not only was the sound ann... Read full Story
Chrissy Tunnell 2024-07-15 2,819 Crossdresser Bareback Fetish Blowjob Ladyboy gangbang domination Guy Fucks Shemale sissy double anal
100%
My Noisy Upstairs Neighbors Part 3: Making Porn
In Part 2, I recounted how Paul, my commanding upstairs neighbor, coerced me into making porn with him and his younger roommate. Now, I'm excited to share the first video we created together. At 12:45 PM on Saturday, I nervously approached Paul's door. After knocking, Paul opened it with a smile ... Read full Story
Chrissy Tunnell 2024-07-16 2,273 Crossdresser Amateur Group Sex Bareback Fetish Blowjob Ladyboy gangbang Lingerie domination Guy Fucks Shemale sissy femboy
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 8,858 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
71%
meijiao dream
My father and I live on farms, mountains, forests, beaches. In the sunshine, I twisted my naked carcass to provoke Dad's animal desire, and the anus cave was large. Never close because Dad's meat stick sprays semen Wear neck collar, nose hook, hand shackles, foot shackles, bells, breast rings, st... Read full Story
Bluesyangiip 2019-05-07 4,195 Crossdresser Fetish Asian Ladyboy Guy Fucks Shemale Mature
80%
Manusha sleeping with a bank manager for loan approval
The incident of this story is almost 5 years old and this happened between me and a bank manager in a leading nationalized bank and you know for what he was demanding a favor from me? Hehehe.. That’s in the story..! This was in 2015 when I applied for a personal loan from one of the leading nati... Read full Story
Manusha Tranny 2021-10-14 7,691 Crossdresser Amateur Blowjob Asian Ladyboy Lingerie Guy Fucks Shemale Mature Homemade Ass to Mouth cum in mouth
77%
Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
Regina10 2020-09-16 5,545 Crossdresser Big Tits Cumshot Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Ass to Mouth
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 2,847 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
50%
I and the old man's story 后面中文
I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... Read full Story
Oldslut Sissy 2024-04-15 9,144 Crossdresser Amateur Masturbation Asian Ladyboy Guy Fucks Shemale Mature small cock Homemade sissy chinese teen (18+)
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 4,312 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
How I Became His Office Fucktoy
Until this job ended last year, every day at my lunch break I would service one of my many Daddies in his office in the building where I worked. He'd always slip me a few bucks, a $20 or even $50 afterwards, not as a payment for sex, but as a "tip" "for all the hard work you do here," he says. I wor... Read full Story
Chrissy Tunnell 2022-02-18 3,853 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,754 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
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 4,941 anal Crossdresser Big Tits Creampie Fetish Blowjob Big Cock Ebony Ladyboy Guy Fucks Shemale Mature big ass femboy
100%
A Wife Comes Around Chapter 2
I caught my breath after my wonderful experience, as we were all around the table now commenting on my orgasm. I sipped my drink and exclaimed that was the best orgasm I've ever had. It was getting late now and I had to get going. I put the sopping panty in my bag and thanked everyone. About a mo... Read full Story
shemale lover 2012-07-25 4,187 Group Sex Cumshot oral
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 2,539 Crossdresser Amateur Cumshot cum Ladyboy Lingerie Sex Toys Homemade shemale + shemale sissy crossdresser siisy slut
50%
L'ESCLAVE SEXUELLE DE MA COPINE ⚧️
Je me présente chez ma copine après qu'elle m'ait envoyé un texto me disant à quel point elle me voulait. Je frappe à la porte et elle répond. C'est une beauté aux cheveux corbeau, d'environ 5'10 avec des yeux marron clair et une carrure assez mince mais athlétique. "Je suis tellement contente qu... Read full Story
Femboy 2021 2023-02-17 840 Stockings Crossdresser Cumshot Fetish gangbang Lingerie Shemale and Girl domination Sex Toys cum in mouth
100%
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'attentionné je suppose ? ... Read full Story
Femboy 2021 2023-02-17 1,096 Stockings Crossdresser Cumshot Fetish Blowjob Big Cock gangbang Lingerie domination Guy Fucks Shemale Interracial Sex Toys cum in mouth
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 8,161 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
85%
Cheating Sissy Wife
My name is Ginger and my main stud is Keith, a truck driver, who is only in town once a week. We have and ongoing role-playing fantasy that we carried out whenever he was in town. I am his dutiful ideal housewife who is perfect in every way. My talents excel in both the kitchen and the bedroom. I fi... Read full Story
Regina10 2020-07-27 7,744 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
100%
First intercourse with a man
If you read my previous story, “First time with a man”, I gave my first blowjob. What I didn’t mention at the time, was that I was on my way to work about 2pm in the afternoon, (I worked the swing shift). That afternoon meet up was just to see each other, talk and maybe meet again later. But my e... Read full Story
Mistysis 2020-10-23 7,301 Crossdresser Amateur Bareback
75%
So good fuck with me and my klients.
Hello, I am Francesca, and I offer company to couples and women. A few days ago, a couple hired me for two hours.The woman was fucking me with her strapon while I was stroking the man's cock. She was pushing her hard cock deeper and inside me, I could feel my ass dissolving more and more. I turn my ... Read full Story
Francheskahotass 2021-08-11 3,442 Crossdresser Amateur Group Sex Cumshot Shemale Fucks Guy threesome Ladyboy Lingerie Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth