Sort by
Relevancy

Free Stories

100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 5,281 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 5,141 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 3,428 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Camming Down the Rabbit Hole Ch. 10
As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous nig... Read full Story
Dani_does_Dallas 2022-04-12 3,473 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
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 1,309 Stockings Crossdresser Amateur Fetish Blowjob Big Cock Lingerie domination Sex Toys cum in mouth
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 4,880 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,851 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
62%
Crossdressed Lana - Hannover, Germany
Crossdressed Lana - Hannover, Germany Very Sexy & Compliant Sub-Slut Is Searching For Kinky BDSM Live-Dates At Hannover, Germany!!! I Am Bisexual And Want Men, Woman, Couples And Trans For Outdoor, Swingerclub, Porncinema And Public Sex. I Love To Wear Very Hot & Sexy Clothes Like Lingerie, Stoc... Read full Story
Crossdressed Lana 2020-02-06 4,263 Stockings Crossdresser Group Sex Outdoor Bareback Fetish Blowjob gangbang Lingerie domination Latex Sex Toys double anal
100%
Karen, My School Teacher Part 4
Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... Read full Story
FoxyHosed 2021-02-17 7,810 Crossdresser Cumshot Masturbation Fetish Blowjob Big Cock redhead pantyhose feet toes legs cock ass pantyhose legs
100%
bi to sissy caught and turned
It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... Read full Story
redthongthong 2022-08-02 8,890 Crossdresser bisexual sissy crossdresser forced feminization CAUGHT!
100%
Sultry Mistress,
Sultry Mistress, Natacha has now been living with me for over a year. It is a cerebral and perverse Domina who immediately wanted to submit me to her desires. She took power over me by making me discover my femininity during role-playing games. Like a spider, she imprisons me in her web a ... Read full Story
sandratvtg 2022-09-20 4,050 Stockings Amateur Lingerie domination Sex Toys
50%
SISSY AWAKENING
- Trou de gloire du sex-shop - "Hey bébé, quand est-ce que tu rentres à la maison?" le message texte bourdonnait doucement. Sortant discrètement le téléphone de ma poche, je tape "Même heure que d'habitude, juste après 5 heures, pourquoi... quoi de neuf ?" C'est mon amante Sarah, ma meilleu... Read full Story
Femboy 2021 2023-02-17 1,258 Stockings Crossdresser Outdoor Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
100%
COMMENT NATHAN EST DEVENU NATALIE ⚧️ ⚧️
Je m'appelle Natalie mais ce n'est pas le nom avec lequel je suis née; c'est plutôt le nom que ma femme m'a donné quand elle a fait de moi sa "sœur" et sa poule mouillée cocu peu de temps après notre mariage. Mon vrai nom est Nathan mais c'est un nom que je préférerais ne plus jamais utiliser parce ... Read full Story
Femboy 2021 2023-04-23 1,606 Teen (18+) Blowjob Lingerie Sex Toys small cock sissy cum in mouth sissify poule mouillée et fille premiere foi
87%
The Hotel Part 1
I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days. Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, fucked fem, huge dildos, and giant buttplugs are just a few of my fetishe... Read full Story
shemale lover 2012-02-11 6,061 Fetish cum domination Sex Toys
60%
A Ski Bunny is Born Chapter 3
Kim and I are thrilled that so many people are enjoying reading about our adventures. We have received so many really nice e-mails from lots of lovely people, its good to know you girls and guys out there are enjoying them! We had promised each other a trip to Europe but hadn't really made any fi... Read full Story
shemale lover 2012-06-22 8,281 Cumshot Sex Toys 69 position handjob
50%
RÉVEIL SEXUEL SISSY ⚧️ ⚧️
Si ses histoires étaient vraies, non seulement beaucoup d'hommes ont eu des réveils sexuels entre la fin de la trentaine et le début de la cinquantaine, mais beaucoup d'hommes de mon âge étaient curieux de se féminiser, de sucer des bites et peut-être même d'avoir des fesses. Mais je ne peux pas ... Read full Story
Femboy 2021 2023-02-17 1,154 Stockings Crossdresser Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial Sex Toys cum in mouth
91%
Birth of a New Sissy Part 1 Encounter
I met Jeff one day at the nearby tennis courts. I could never have imagined what the result of that meeting would be. I suppose I should tell you a bit about me. I'm a happily married 34 year old. About average in most respects. A little spare tire trying to form around the middle but in decent ... Read full Story
shemale lover 2011-11-17 5,319 cum Sex Toys crossdressing
100%
Camming Down the Rabbit Hole Ch. 07
Opening my eyes I struggled a little as the residual cum on my face from last night’s show hadn’t been fully wiped off, I felt the dry and crusty leftovers crinkle on my skin, but couldn’t help but smile to myself as I remembered how it had got there. The intensity of that orgasm had been on another... Read full Story
Dani_does_Dallas 2021-10-22 6,317 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
100%
Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
darrell 2022-01-03 4,333 Group Sex Big Tits Cumshot Bareback Fetish Blowjob Big Cock Asian Ladyboy Sex Toys Mature cum in mouth shemale + shemale
100%
My Sissy Fantasy Part 3
We come to another set of double doors, though these are glass paned in Victorian iron work painted white, as is the wall which it I set in. But due to the humidity all the glass is misted, including the dome and I can’t see where they lead outside. Jake opens one of the doors and we step into... Read full Story
shemale lover 2012-03-27 2,949 fingering oral sex Sex Toys
100%
Fender Bender Chapter 9
My name is Robert, I have been cross dressing since I was 14. I turned 18 last summer and this story takes place during my senior year in High School. I am 5'9" 160 pounds, blonde hair and blue eyes. When I am dressed I call myself Vicki. __________ I had met Julie at a recent party. Well... Read full Story
shemale lover 2012-07-27 3,413 Group Sex Cumshot Sex Toys
100%
First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
Trapbomb1 2022-07-29 6,746 Teen (18+) Crossdresser Bareback Creampie Blowjob Big Cock virgin virginity sissy cum in mouth double anal sissy slut virgin ass
66%
Elizabeth: Beginnings of a Sissy
I had a pretty good system going. My 18 year old sister would stay up to watch Sex And The City reruns with me (well she watched, and I smoked weed), and during the first ad breaks, would run downstairs and get changed for bed. During the next ads, I would go to the bathroom, and on my way, raid her... Read full Story
shemale lover 2012-04-02 4,664 first time Fetish Blowjob facial Sex Toys sissy
64%
Caught in Panties & Dominated
I love to wear sissy clothes, and I fantasize about being controlled by a dominating mistress, who forces me to wear her clothes, to take her boyfriend's cock into my virgin mouth, make love to his big stiff cock, deep throating it until he comes into my mouth, filling up my mouth until his hot cum ... Read full Story
shemale lover 2012-10-15 6,320 Fetish oral domination Sex Toys sissy
90%
DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
CD DIXIE IN NH 2016-05-10 10,220 Big Cock cumming sperm ebony cock
50%
lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
hippocampus_171 2023-07-09 4,698 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
90%
A Sissy (S)exercise Fantasy
I stopped going to the gym about six months ago, when money got tight and I had to find ways to reduce my expenses. I usually don't get to the gym much in the spring or summer months anyway, so it was an easy expense to cut. I hate going into the office all sweaty, so I avoid working out in the morn... Read full Story
shemale lover 2012-06-14 9,313 Cumshot Fetish domination oral sex sissy
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 7,623 Crossdresser Bareback Big Cock Ebony Ladyboy Lingerie Ass to Mouth cum in mouth double anal
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 4,168 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
90%
Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
Regina10 2020-11-30 9,235 Crossdresser Bareback Creampie Fetish Blowjob blonde Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth double anal
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,485 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
100%
The Three of Us
Imagine you are a lonely person on the inside, and just wanting all your life to be loved for who you are. Holli Artigas, was just that person. Wondering whether her obsession with Jon Silva, a football star, was from a casual encounter, or was she truly fond of him? Growing up in the Sao Paulo, ... Read full Story
Jon Paul 2024-04-28 3,187 anal Creampie Shemale Fucks Guy threesome Shemale and Girl cum in mouth double anal shemale fucks female
90%
Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... Read full Story
shemale lover 2012-03-01 13,929 first time sucking fuck domination
37%
First time Crossdressing
I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards that allow members profiles and posting messages. I also post to local groups in my area that allows one to post messages to a small geographical area or to a distant user g... Read full Story
shemale lover 2013-07-17 6,095 first time Crossdresser Fetish Mature bisexual
50%
SOUS LA DIRECTION DE MAMAN
Jaime n'avait jamais eu beaucoup de chance avec les filles du lycée. C'était venu et reparti, et maintenant il en profitait un l'été dernier avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un crétin ou un crétin, c'est juste que la vie et la... Read full Story
Femboy 2021 2023-01-26 1,465 Stockings Teen (18+) Crossdresser Cumshot Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
50%
SOUS LA DIRECTION DE MAMAN ⚧️ ⚧️
Jaime n'avait jamais eu beaucoup de chance avec les filles au lycée. C'était venu et reparti, et maintenant il profitait d'un dernier été avant de partir à l'université avec sa virginité intacte. Ce n'était pas vraiment sa faute, il n'était pas un salaud ou un douchebag, c... Read full Story
Femboy 2021 2023-03-18 1,054 Teen (18+) Crossdresser Cumshot domination Sex Toys cum in mouth
50%
PREMIÈRE ÉTAPE FÉMINISANTE
Aujourd'hui, ma mère et moi sommes allés acheter des maillots de bain dans un grand magasin local. C'était en début d'après-midi et nous avions pratiquement l'endroit pour nous tous seuls. En entrant dans le magasin, nous sommes passés devant une grande colonne couverte de miroirs, et je me suis ... Read full Story
Femboy 2021 2023-01-27 900 Stockings Teen (18+) Small Tits Crossdresser Fetish Lingerie domination Sex Toys
50%
LA CRÉATION DE MONICA ⚧️ ⚧️
Je savais. En regardant en arrière maintenant, je me rends compte que j'ai toujours su. Je n'ai jamais rien fait à ce sujet, jusqu'à ce que je sois prêt mentalement, émotionnellement et physiquement. Je suis né Matthew J. Smith au milieu des années 70 en Amérique centrale aux États-Unis. J'ai grandi... Read full Story
Femboy 2021 2023-03-30 924 Stockings anal sex Masturbation Fetish Blowjob Big Cock Lingerie Sex Toys feminization cum in mouth poule mouillé poule mouillée et fille poule mouillée poule mouillée
87%
Feminized By My Mother Chapter 2
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... Read full Story
shemale lover 2012-07-24 13,156 sucking Fetish fucking sissy
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 8,990 Stockings sucking domination
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 4,538 anal Crossdresser Cumshot Fetish oral domination
66%
Cassandra Chapter 1
Cassandra is a tease, a flirt, a slut, a girl who lives very much for the moment. Unconcerned with propriety or fashion trends, she dresses in clothes that go right for the jugular of a fetishist's libido. Spandex, leather, latex, spike heels, corsets, overdone hair, make-up and fingernails - these ... Read full Story
shemale lover 2012-03-27 5,867 sucking fuck orgasm crossdressing
100%
Dress Up
I don't know how to explain it. I am not gay although I may be passive bi. I have had sex with men, but not a lot and I have always been the one receiving, you know once a friend showed me a pack of pictures of his wife from fully dressed in conservative suit to complete nude with some action photos... Read full Story
shemale lover 2012-11-17 4,527 Fetish cum oral sex Sex Toys cum swallowing
88%
Caught Crossdressing by a Real Man
This story is a continuation of night club cum slut. Ever since I first wore panties for a boyfriend, I had built up a collection of lingerie. I gradually worked up from panties to the most erotic lingerie I could find. My fascination with cross dressing went a little further with a new fetish f... Read full Story
shemale lover 2013-01-17 35,497 Crossdresser sucking Lingerie ass fucking ass fingering
83%
the start of what to cum
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often mo... Read full Story
oliviabecket23 2023-07-04 6,738 Crossdresser Lingerie domination Sex Toys femboy forced webcams
91%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,380 Big Tits sucking ass licking fucking
88%
Feminized by My Girlfriend
About 6 months ago I joined a gym because I have never had a very masculine body and now that I just turned 21 it was time to finally get off my butt and try to build some muscle. That is where I met my girl friend Brook who stands 5' 9", has a fantastic body and a gorgeous face. She looks like... Read full Story
shemale lover 2012-07-14 16,539 Fetish oral Sex Toys feminization
71%
Becoming A Girl
This is a story how I became my step moms little girl. You see I had a very tragic childhood as a boy and grew up to become the girl I am today. But then again it is not so bad because for some strange reason it does feel very normal to me because it is the way I was raised and at times I have felt ... Read full Story
shemale lover 2012-03-03 8,193 anal sex Fetish fingering Sex Toys
50%
The change
Hello my name was Joe until I got caught in my girl friends cloths one day. Then my life changed ,some say for the better others say its for the worse. Here is how it all began. MY girg friend was out of town for a few days and I was house sitting for her . She had a cat I had to take care of. I ... Read full Story
shemale lover 2012-04-18 3,708 Sex Toys crossdressing sissy
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,516 Cumshot Masturbation oral sex
75%
Friends United
I'd been best friends with Brad since coming to the US from England as a child. We met at school and since those early years did everything together. He was very outgoing whereas I was passive. Now in our thirties we are still best of friends and even work in the same company. Brad loved motorcycles... Read full Story
shemale lover 2012-11-30 4,943 Fetish dildo Sex Toys crossdressing
100%
Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
shemale lover 2013-01-04 10,172 sucking Fetish Uniform domination big boobs
100%
Debbie Part 8
Moira sat in her booth at the entrance to the subway station and saw people pass by. She sat there every day selling tickets, and although several thousand people passed her during a shift, she could now recognize many of the regulars and she even knew when to expect them. It was now almost 9 o'cloc... Read full Story
shemale lover 2011-12-23 7,325 transgender toys bondage and discipline heavy
50%
Sissies Training Part 2
I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by ... Read full Story
shemale lover 2011-09-17 6,558 shemales Fetish bdsm
50%
The Visit
A visit to a hooker, where I describe my bisexual experiences *** It was a weekday, I had bummed off work and had made my way to Ipswich for a visit to Rona, my favorite hooker. She was a lovely woman in her forties, with a fantastic figure, not slim but not fat and with huge tits. She... Read full Story
shemale lover 2012-01-26 8,304 Group Sex licking sucking pissing fucking
25%
Adult Bookstore Dancer
Adult Bookstore Fun At one time there were eight adult books in my city now there is only one. Makes me very sad as I loved dressing up like a twenty-five cent whore and visiting them on the weekends. I think I enjoy all the humiliating comments and condescending looks the customers would make abou... Read full Story
shemale lover 2012-02-26 4,181 sucking Fetish cross dressing