Sort by
Relevancy

Free Stories

56%
Blow Job
My e-mail is: My rusted, green Toyota Tercel pulls into the mall parking lot. I pick a spot at the back, beyond where even employees park. The next car is a blue pickup 20 spots away. No one parks here, except at Christmas. But I know that I'll soon need the privacy. I'm a freak, a cross-dresser... Read full Story
shemale lover 2013-08-09 7,072 Crossdresser Masturbation Lingerie stripping party
86%
A wild adventure
I was driving down the Pacific Coast Highway one day in my pickup. It was sunny, and beautiful, a perfect California day. Only problem was the traffic. You could barely move. Still, you could hear the waves and the gulls and I was feeling good. I had noticed the blond in the convertable ... Read full Story
shemale lover 2014-07-23 5,724 Cumshot Masturbation shemale stroking handjob
95%
Mai
When I was twelve I met a new classmate named Dave, he and I became great friends hanging out, joining clubs and what ever else high school kids do. His family was from the Phillipines and he and his sister were the first generation born in this country. His sister Mai is the focus of this story. ... Read full Story
Zöe from Kingston 2018-08-09 11,509 Cumshot Bareback Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale Interracial cum in mouth
90%
Long weekend at work
So I am the low man on the scale at work. My job is with the City I work in dispatch and am one of the people responsible for getting road crews, hydro and sewer crews out to fix problems wherever they occur. My boss is a very attractive woman named Jamie. She stands about 152 centimeters and dar... Read full Story
Zöe from Kingston 2018-08-09 6,110 Cumshot Bareback Shemale Fucks Guy Blowjob cum in mouth
93%
Sissy Experience - Episode 1: The Beginning
Hello All, Hope you’re all doing well!! This story narrates the beginning of my crossdressing and sissy adventures. Before I begin I’ll tell you somethings about my family. We are a family of four consisting of me, mom, dad and an elder sister. I am currently 20 years old and in college. My da... Read full Story
brownsissyboi 2020-05-15 8,303 Teen (18+) Crossdresser solo Amateur Cumshot Masturbation Fetish Asian Lingerie Homemade
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 5,082 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
100%
Camming down the rabbit hole Ch2
How had I ended up in this situation? Sure I was going to need to make ends meet, but I could find a normal job couldn’t I? was I this desperate? Perhaps desperate wasn’t the right word, just over a month ago I had started out camming as a bit of fun, to maybe make a few pounds while I masturbated, ... Read full Story
Dani_does_Dallas 2021-08-11 3,815 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
100%
First Encounter (Mexican Travesti)
I grew up near the U.S.-Mexico border and am ½ Mexican Hispanic and ½ Anglo (white). I visited Nogales Senora on the Mexican side on and off during my teen years. As a young adult, I was fearless and sometimes went across alone to visit the strip clubs, get a cheap lunch, or look for Mexican sweetie... Read full Story
AllenB 2022-09-07 7,072 anal sex Shemale Fucks Guy Blowjob mexicana cum in ass first time with a tranny
100%
Tasting the good FLESH
I am no longer Virgin, en bon et du forme Thing never dared since I taste the enjoyment by all the senses and in all its senses... I discovered her when she smiled at me as a thank-you for giving her the way to the small-town supermarket where I was on business. Sandals at her feet of Cinderell... Read full Story
hippocampus_171 2022-11-10 5,010 Amateur Creampie Shemale Fucks Guy Guy Fucks Shemale Mature Ass to Mouth cum in mouth
100%
Towel Boi: You're Hired
Kasey Stevens woke up in his new studio apartment. The five-foot-nine, blue-eyed sissy with ash brown hair yawned and stretched before heading into the bathroom. He showered, taking good care to lather his rosy skin with strawberry scented body wash. He shaved his legs and rinsed off. Then, he appli... Read full Story
Faggyboi and Puzziboi 2023-11-14 6,292 anal Small Tits Crossdresser Amateur Bareback Blowjob Guy Fucks Shemale Interracial small cock big ass femboy
100%
The lover of Lisa
It wasn’t that hard making the change from friend to lover, and from lover to student of sensuality. Lisa made clear that I was to follow her directions, not that our relationship was predicated on that, but that she was going to lead me to a new place in my life. She had been a friend for mo... Read full Story
shemale lover 2018-01-04 11,049 shemale orgasm oral sex
75%
A Shemale Vacation Part 3
At the French border, it was discovered that we had no passports. We were taken from the train and into a room for questioning. All four of us, Josh, Olly, Harry and myself, were terrified. Sure, we'd been in a sticky situation before on this trip, sticky particularly for me rather than the others, ... Read full Story
shemale lover 2011-09-05 4,346 anal sucking cum
75%
Amy Finally Lives Out Her Fantasies Part 2
"Wow! What got into you?" "I don't know, I just decided to finally loosen up and go with my desires," she explained. "Did you enjoy it?" "Are you nuts? I LOVED every second of it!" I exclaimed. Figuring the alcohol played a very large role in her sudd... Read full Story
shemale lover 2011-09-15 3,812 Big Tits ass fucking fishnet
81%
Rebecca's Secret
-1- The hour was growing late as I looked around the cozy living room. Six of my friends were sitting in various places, in various positions, all watching some late night horror movie on the television. There was a feeling of general contentment. We had arrived at the house several hours earlier... Read full Story
shemale lover 2011-10-19 5,363 Cumshot shemale oral sex
100%
Rebecca's Secret Part 2
-5- Rebecca lay in my arms, trembling after the most incredibly orgasm she’d ever experienced. Hell, it was the most incredible orgasm I’d ever experienced and I wasn’t even the one who’d had it! We held one another in the darkness, myself stripped of every article of clot... Read full Story
shemale lover 2011-10-19 4,207 Small Tits asshole orgasm ass licking
84%
Page Sixty-Nine
When my wife suggested that we rent out the guest rooms above the garage to a college student it sounded like a good idea. It was very much like a small apartment, with a bedroom, bathroom, and small living room. No kitchen of course, but we could share ours and it seemed like a good way to make... Read full Story
shemale lover 2011-10-20 6,188 cum oral deep throat fucking
100%
Sexretary
Sam Nichols had a comfortable, reasonably well paid job in a computing firm called Stewart Computing. He was twenty two and had recently graduated college and had been lucky to find such a good job in the firm on the edge of San Diego, just a couple of hours drive away from where his parents still l... Read full Story
shemale lover 2011-11-12 8,374 anal shemale oral
66%
Cincinnati Apocalypse Part 4
The problem with Americans-one of the many, anyway-Giles thought, was that they had too much of everything, including too much money and too much time on their hands. What else could explain the vulgar extravagance of a place like Disneyland? The staff at the entrance turnstiles-guards, really, t... Read full Story
shemale lover 2011-11-23 3,166 hardcore celebrities shemale
100%
Bethany's Secret Part 3
-6- February 16th was my birthday and I was eagerly awaiting spending the day (and night) with my girlfriend, Bethany. I had met Bethany six months earlier, when she was just a new student in my high school. I had fallen in love with her at first sight and becoming her boyfriend became my top pri... Read full Story
shemale lover 2011-12-18 4,532 shemale oral fingering
100%
April Fools!!
I'm Jimmy James and I've been hanging out with the same six guys since we started college. We're a pretty close knit bunch and have stayed in touch since then. At 25, I'm the only one of the seven of us still not married. Even though we all still get together for parties and get togethers, for t... Read full Story
shemale lover 2012-01-04 11,588 anal oral cd
75%
Old Folks Part 2
It had been eleven months since that day when I arrived at Honey and Frank's house. It was about 1am at night as I stood in a quiet street waiting for Frank to pick me up. I had just finished with my last client for the night a good blowjob with him ending up cumming on my face. I was touching up my... Read full Story
shemale lover 2012-01-10 7,021 transsexuals erotica romance crossdressers
100%
Mieke and Ellen
It was early morning when I first met Ellen and Mieke. I was walking the dogs and they were out too with their dog. The first thing I noticed was that both of them were gorgeous. The second thing was dissapointment as I saw that Mieke was way too young for me. I'm 27 and she looked as though she... Read full Story
shemale lover 2012-01-22 3,261 Cumshot shemale oral
100%
Jon Story
When I learned we would be in Rio for a few days, I was overjoyed. Rio de Janeiro would have just what I was looking for. While on leave in Australia, I had developed a yearning for special girls, and through careful research, Rio seemed to be someplace very special indeed. It first started... Read full Story
shemale lover 2012-01-26 5,122 Creampie tits fucking big
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 8,411 anal sex Fetish fingering Sex Toys
100%
A Future Society
Anna was lined up with the other girls beside her, the heat from the electric torches on the wall stinging her bare backside. Her long blonde hair stretched down to the top of her ass, shielding her back from the heat, but she often wondered during line ups whether or not a bulb would burst and send... Read full Story
shemale lover 2012-03-05 4,553 Group Sex cum Shemale and Girl
100%
Fulfilling A Girl's Male Fantasy
"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at ho... Read full Story
shemale lover 2012-04-04 3,843 orgasm fingering oral sex Sex Toys
0%
The Day After
I explained in my previous story, which to really understand me you really have to read My life as a girl besides I am picking up where I left off but if you don't want to take the time to read it, I am what they call an intersexual. A term you should look up or go back to the other article to under... Read full Story
shemale lover 2012-05-04 3,441 Cumshot fingering oral sex cum swallowing
60%
Falling For My Roommate Chapter 3
If there's one good thing that college taught me, it was that concentrating in class the day after getting your first blowjob is very difficult. I must've gotten aroused at least four times during my first class, and a couple during the next. It was a true pity that I wouldn't be back in my room for... Read full Story
shemale lover 2012-05-23 3,333 shemale kissing lesbian
100%
Erotic Daydreams
Sometimes I think my parents should have named me Eykan, rather than Eukan. Since I was old enough to get an erection, I have masturbated one or more times a day, three hundred sixty-five days a year. I don't know how much semen I have spilled, but I'm sure that were every sperm in it had impregnate... Read full Story
shemale lover 2012-06-28 3,207 Cumshot Masturbation fuck
85%
Bookstore She-Male Whore
I love dressing up like a she male slut and going into an adult bookstore with movie booths. A lot of them have holes in the wall where you can watch and be watched. I love lifting my short leather mini skirt up and letting men see my cock pushing up against my black leather g-string panties. Som... Read full Story
shemale lover 2012-08-04 3,978 shemale cum jerking off rimming
100%
How I Became Vanessa Chapter 1
PART I: I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husba... Read full Story
shemale lover 2012-10-31 3,959 anal Cumshot Masturbation Sex Toys
100%
A Close Encounter
Another great tape and another great yank of the crank. Yea, she-males were pretty hot, Tom thought as he hit the eject bottom on the tape deck, but where on earth would he really find one? He had little doubt that if he did find a place where they hung out that there would be more than a few with a... Read full Story
shemale lover 2013-07-16 4,136 tranny Cumshot shemale sex transexual
94%
Working Late with my boss
Hello, I want to tell a story...my story, about my first love with a shemale who just happened to be my boss. I worked at a bed, bath, and beyond store. I had worked there for about 1 year and a half, and my boss really liked me. I always went and picked up her lunch with mine, never messed up. Her ... Read full Story
MightyMax1234 2014-01-11 10,442 shemale oral deep penetration boss
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,789 Crossdresser hardcore ass fucking cd
80%
JUERA MARICON
My name is Keven Jeanne and, Yes, I am a Sissy! When I was 13 I put on my mom's panties and some of her lipstick when she was at work. I had longish blonde hair and I ruffled it up - kind of teased it up - and when I looked in her dresser mirror, I almost ejaculated. Because what I saw looking ... Read full Story
Kevyn-JeanneHarris 2015-12-25 6,519 blonde shemale submissive cocksucking
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 18,247 big dick anal sex suck Blowjob cock sucking workplace
100%
Leslie
Where do I start? How about at the beginning. My name is Cal I am divorced and living alone. I am not a bad catch I am five foot eleven, short black hair, green eyes and no visible scars. I am a regular at the gym so I am in shape but not ripped. A seven inch uncut cock that I can use well. I... Read full Story
Zöe from Kingston 2019-02-04 9,413 Cumshot Bareback Blowjob Guy Fucks Shemale Bra and Panties
94%
The Transsexual Teacher
Greg was late for class. He ran through the hallways. They were very particular about being punctual here. His health teacher especially. She was very focused on such things. Greg had been late twice this week. He couldn't help that his car kept breaking down. Ms. Sin was a real hardass and didn't a... Read full Story
ASSEaster5678 2019-03-18 34,186 Shemale Fucks Guy school teacher sex
83%
Fantasy dream
So i had this dream and it gave me such a raging boner i felt i had to write it down. Im at a party, everyone is wasted and having a great time. I had been dancing and flirting with some blonde chick who kept mentioning her friend and wondering where she had gone. Eventually we found her and went... Read full Story
Wanksalo 2019-04-15 4,231 Cumshot Blowjob blonde Shemale and Girl
100%
My suit fantasy fulfilled
I've always had a thing for a man in a suit, a really smart suit. Maybe it's a secretary fantasy or something, but I just think every man looks sexy in a suit. So it was with great delight that upon making contact with a guy on Grindr a few weeks back, is profile pic showed him in a suit. While t... Read full Story
hornywilla 2020-09-14 3,191 Stockings Crossdresser Blowjob trans Lingerie kissing crossdressing bj crossdresser fucks hotel room hotel fun cdtv
100%
Camming down the rabbit hole Ch5
I was jolted out of my sleep by the phone on my bedside table vibrating, bleary eyed I picked it up and saw a message from the couriers that a package would be delivered today around 4pm. The realisation that this was the package I had been waiting for and I could finally wear something else in my s... Read full Story
Dani_does_Dallas 2021-09-29 5,215 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade cum in mouth webcams
90%
Camming Down the Rabbit Hole Ch. 08
A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... Read full Story
Dani_does_Dallas 2021-11-15 4,090 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 4,307 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
100%
First work day!
Having just graduated from college in Miami I took up fashion as a career! Impressed? In fact, I managed to land a job as a clerk in ready-made clothes shop. Sounds not as impressive as I’d like to have but that is just a beginning. You think there are no other interesting places in the whole ... Read full Story
shemale lover 2014-05-31 9,282 tranny asshole
92%
Finally, My First Tranny!!!
I just came out of the doctor's office in downtown Philly from my 3 month check-up. I was pretty horney since my doctor is a female and I had a complete physical so she and her nurse were in the room with me. I got to the train station to go back to Willow Grove and was standing on the platform when... Read full Story
shemale lover 2015-07-19 34,658 anal first time shemales
85%
Jenna & Stephen Part 1
Jenna and I have been friends for nearly 15 years. We dated ever so briefly about 12 years ago, but nothing more than kissing and heavy petting occurred before she decided it wasn't going to work out. At the time I was heart-broken, but looking back now, I realize she was correct that we weren't rig... Read full Story
shemale lover 2011-09-01 4,285 dildo orgasm
50%
At Risk
Diane was proud to be a shemale. She loved having a beautiful face; long, silken hair; fabulous breasts; a firm, flat tummy; functioning male genitals; long, shapely legs; and firm, compact buttocks. She loved wearing makeup and dressing in fancy, frilly clothes. She also loved the way men ogled her... Read full Story
shemale lover 2011-10-20 3,789 shemale massage stroking
100%
Sweet Sherri
"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people wa... Read full Story
shemale lover 2011-10-31 5,729 Big Tits transsexual big ass
100%
Jamie is taken Part 3
When this process was completed the Chinese gentleman s turned to his new acquisition in the floor. He lifted him up from the floor and deposited him on a high-backed chair; his legs still folded up, and tied him to it. Then he removed the strap from around his throat and instead shoved ... Read full Story
shemale lover 2011-11-30 6,632 Fetish domination bondage facefucking
100%
Marilyn's Family Reunion
The warm humid September air blew through the windows of the speeding silver Nissan Pathfinder as it cruised along the Belt Parkway. With the Marshall Mathers LP blaring out the stereo, Sharilynn whipped her SUV along as the wind whipped her ponytail and her plain white t-shirt. As little Mai lay sl... Read full Story
shemale lover 2012-01-02 4,589 sucking Shemale and Girl cum swallowing
75%
Becoming A She-Males Bitch Part 3
When my alarm went off, it woke me up abruptly and scared me. My heart was pounding so I took a minuet and got myself together. I went into the bathroom and removed my collar. I took a shower, shaved and applied my make-up. I grabbed a thong from my dresser; I picked out a pair of heels from my clos... Read full Story
shemale lover 2012-01-04 3,717 Cumshot domination humiliation
0%
Dreams
The TV is on with the sound on mute and I hear the sound of cars and trucks running by the outside of the building just close enough for me to hear the tires rubbing against the asphalt as they go by. I can't find much to do in this little town and the closest source of entertainment is a half h... Read full Story
shemale lover 2012-01-21 3,869 suck shemale fantasy
80%
Career Shift
Receptions are not my favourite things in the world to attend. I don't mingle and 'rub elbows' like agents and sales people do. I usually end up at the bar drinking alone, looking at all the phoney people. I am a writer, a sports column writer more specifically. The magazine that I write for is one ... Read full Story
shemale lover 2012-03-06 5,950 Group Sex Blowjob fingering orgasms
50%
Carol, The Saga Continues
It's very late Monday night as Carol returns from the date that J C had forced her to keep, she places her purse on the hall table, throws her jacket over a chair and walks toward her bedroom. She can't wait to shed this clothing that J C demanded she wear. As she walks, her feet, clad in the five i... Read full Story
shemale lover 2012-03-09 2,891 anal sex shemale deepthroating
88%
Didn't Know
My name is Mark Denny, turned 22 years old last friday. I work at the local supermarket as a cashier. Friday nights there is always this girl, Sandy who is my bagger. She is 5'7'' long blonde hair, beautiful blue eyes, full lips, from what I can tell a nice ass. Of course I was attracted to her, who... Read full Story
shemale lover 2012-05-09 3,972 anal sex Cumshot Blowjob
100%
Betrayed Chapter 1
She's having an affair. I couldn't ignore it any longer; the evidence was right there on my monitor that Wednesday afternoon. I had felt so... tawdry – a word I had thought I would never use – hiring the detective to follow her, follow up on my suspicions. It was as though I was betrayin... Read full Story
shemale lover 2012-05-28 6,613 anal sex Cumshot shemale oral sex cum swallowing