Sort by
Relevancy

Free Stories

100%
Roberta, Molly and Ed
Friday "Commander Cromartie?" Lt. Commander Edward Cromartie, USN, turned toward the voice that had spoken his name. He saw two female naval officers, a tall willowy light-skin Black woman, and a short Asian one. The Black one was wearing the uniform of a full commander, the Asian of... Read full Story
shemale lover 2012-09-04 5,382 Cumshot threesome Blowjob Big Cock condom sex
100%
Transsexual Sisters Chapter 3
Part 3: Their First Men Dawn and Cassie searched for Michelle and Nicole. They did not appear to be anywhere in the club. Pixie saw them looking and told them: "Your ladies left a long time ago with their new friends Marty and Brandy." Pixie said. They left me a note for you. "H... Read full Story
shemale lover 2012-09-07 2,893 Blowjob Big Cock fuck oral sex tits licking
100%
Love to Fantasize
I love to fantasize; it is one of the greatest things on the face of the earth. I have many fantasies, tho I have given up on a couple since I married my wife. I am a white male of 27 years, and since I was sixteen, I have had many erotic fantasies stemming from reading my parents adult story magazi... Read full Story
shemale lover 2012-12-20 3,790 Cumshot sucking ass fucking deep throat cd
97%
How I Met Alyssa
I groaned as the sun was shining onto my face. I turned around so I could get some more sleep, but I saw it was 9:22 am and I decided it was time to get up. I got out of bed and went to the bathroom of my little apartment to freshen up a bit. I looked at myself in the mirror and saw a 20 year o... Read full Story
shemale lover 2013-02-12 14,188 hardcore sucking Big Cock ass fucking big boobs
88%
How I became a Transexual
I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I w... Read full Story
shemale lover 2013-07-19 6,405 Cumshot Masturbation transsexual oral sex ass fingering
95%
CD Jinn New Adventure
So my last story "college experience" was about one of my three roommates finding out I was a cross dresser along with his girlfriend. His girlfriend Stacy encouraged him to dominate me and display power over me. I think that is really what she enjoys seeing. While he was slipping his cock... Read full Story
Jinn.V23 2014-04-11 6,874 Crossdresser threesome ass fucking domination rimming
87%
My 1st time with a shemale
I always had the fantasy to be with a shemale, and today i gained the guts to go to a shemale. I saw the add in the newspaper and called, she was a brazilian (ussually the best ones are brazilian :) ) When i arrived to her apartement, she had a beautifull lingeri, and i noticed her big tits, my co... Read full Story
zongf2008 2014-09-02 4,865 first time ass suck shemale dildo
90%
Lost Island
Bright light hit my eyes when I opened them after a long time. My mouth was full of sand, my toung dry and the taste of salt overwhelmed me. I was stranded. My boat sank in a terrible storm and my body was washed on this lonely beach of a tropical island. The sea was calm and there were almost no w... Read full Story
xgandalf 2016-05-04 6,366 sucking gangbang domination ass fuking Shemale on Guy
78%
Once wasn't enough!- my 2nd shemale exp
So after my first experience I got really into the porn I bought movies magezines got on websites just couldn't get enough. But watching it wasn't enough I had the real thing once and wanted it again. It had been almost a year now and only one person knew about what I had done that one fat... Read full Story
Duke04 2017-04-01 10,465 anal sex Shemale Fucks Guy ass fucking Shemale on Guy
73%
Tabitha at 19
Tabitha’s home from her freshman year of college. She’s gone off to California to a screamingly liberal school and I’m sure she’s been making new friends, learning new things, opening her horizons and fucking safely. After I popped her cherry and we had a very discreet summer of me teaching her a lo... Read full Story
Giantsquid 2017-05-16 6,703 Small Tits Amateur Cumshot Blowjob Guy Fucks Shemale cum in mouth
80%
Three In A Day
Clara felf especially slutty today. She briefly gazed at her long legs shimmered in the smooth, silky black stockings, and black patent leather pumps as she pressed the gas pedal of her car. Her olive skin and black wig were set off by the brightest shade of red lipstick she could find. Driving d... Read full Story
iluvgurls 2018-11-12 4,616 Small Tits Crossdresser Group Sex Cumshot Blowjob cum in mouth
60%
The Greatest Liar, Date With The Devil
The Greatest Liar, Trans Erotica With A Purpose © Alexandra Rios 2019, all rights reserved Disclaimer This is a work of fiction. All characters (including the narrator), firms, business entities, organizations, teams, products, medical providers, medicines, governments, government officials, c... Read full Story
the greatest liar 2019-08-20 4,162 Big Tits Bareback Creampie Guy Fucks Shemale
100%
Sports Bar Pre-drink
Sitting on the chair leaning against the bar, Steven sat quietly sipping on his rum and coke. It was a fairly quiet night at the local sports bar he often ventured to after work to wind down from his work shift. Steven looked up at the door as a small group of women walked through laughing and ta... Read full Story
Master VeeJay 2019-09-27 9,457 Big Tits Blowjob Asian Guy Fucks Shemale
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 11,416 Teen (18+) Small Tits Crossdresser Fetish Blowjob Lingerie Guy Fucks Shemale cum in mouth
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 5,285 Big Tits Cumshot Bareback Creampie threesome Guy Fucks Shemale cum in mouth
100%
The Fabulous Alessia Travestita
Alessia is a real transexual. Several of her porn videos are on this site. She collaborated with me in this story. Alessia is a natural blonde haired, brown eyed, mature fifty -five year old Transsexual woman from England. She is tall, very fit, stands 5'11," 36B-26-30 and a slender 133... Read full Story
darrell 2021-12-14 4,372 Crossdresser Blowjob blonde Big Cock domination Mature 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 4,825 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock Mature cum in mouth
95%
My TS Journey
I'm a straight, married guy in my 30's, at least that how I appear to everyone that knows me. I have an intense obsession with Trans women that I have been indulging since I was a teenager. Over the years this fixation has grown into something that ranged from watching porn initially, to having my a... Read full Story
iconicirish 2022-10-26 8,277 Amateur Shemale Fucks Guy Big Cock domination cum in mouth escort ts
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 4,741 anal Small Tits Amateur Group Sex Masturbation Guy Fucks Shemale Sex Toys Mature small cock big ass sissy femboy
94%
MILF Alessia Travestita finds a bottom boy
I was several days into a cruise to New Zealand and Australia with my wife. This morning my wife went on an excursion that I had no interest in, so I had the cabin to myself. I hadn't had any sex with my wife in the last 3 days due to the activities such as the various jaunts to Auckland and the sur... Read full Story
darrell 2023-08-13 6,218 anal Cumshot Shemale Fucks Guy Fetish blonde Big Cock domination Mature deep throat cum in mouth sandals
100%
Hung Shemale has Motorcycle Trouble near Vegas
I drive down a deserted two- lane highway outside of Las Vegas, Nevada. It is August and the temperature is well over 100 degrees. In the distance, I see a tall beautiful mature creature that walks alongside the road. As I pull over, I am stunned by her powerful physique. She sports an incredibly ti... Read full Story
darrell 2024-02-02 5,505 Shemale Fucks Guy Blowjob blonde Big Cock Mature deepthroat cum in mouth toe sucking Fisting Anal
50%
MISTRESS'S TERROR
The night had ended EXTREMELY PLEASUREABLE with BILLY, RYAN & PETER in a literal BANG and I was HAPPY. Now that BITCH I were married with our diamond 2 carat engagement rings and diamond wedding bands we were LESBIAN LOVERS. We were perfect together, Aunt Susie had groomed me into a SHEMALE DOMINATR... Read full Story
BITCHGURLvr 2024-07-01 4,237 cock transsexuals smoking cigarette
92%
My First Girly Cock
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2014-03-29 18,752 anal first time shemales
100%
Little cock convention
They came from all over the nation to downtown LA convention center. It was the "Little Cock Convention" I watched as men from all races and status came in. Sometimes they came with their wives,friends,Mistresses,lovers, or even their boyfriends. I was on Guard duty and walking the conven... Read full Story
shemale lover 2014-07-07 7,052 shemales hardcore sex humor
94%
Miss Tiffany Fulfilling Her Dream
Finally, I had everything I needed to dress up for a little fantasy today. Ever since I was a little boy, I had always thought my neighbor Steven was extremely handsome and sexy. At 6 feet 3 inches, Steven is exactly what is described as tall, dark, hard tone and muscular. Tonight, I would finally h... Read full Story
shemale lover 2014-11-17 4,599 ass licking perky tits face fucking
97%
The Roommate
I’ve been rooming with Bob for two years now. He and I met about 5 years back, while we both worked at the grocery store to get through college. We were good friends from the moment we met. We had similar interests, were both outgoing, good looking, and hated working at the grocery store. ... Read full Story
shemale lover 2018-02-26 21,357 suck Creampie ass licking
100%
My Surprise
Here I was in another strange town; the hotel was as usual just one of Those places you sleep in and I was bored and fed up with travelling A drink I thought I need something to relieve the boredom. An hour later I was in a bar in now what was the name of this town ?, Drinking alone in the corn... Read full Story
shemale lover 2011-08-31 5,618 Small Tits sucking pussy
94%
The Babysitter's Secret
The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated... Read full Story
shemale lover 2011-10-24 21,146 Blowjob perky tits handjob titfuck
75%
Experimenting with Cock
I was 22 and at the time did not have a girlfriend. I had a habit of jerking off at least once a day if not more. Starting masturbation at an early age made me bored by "normal" porn star videos. Leading me to amateur porn. Soon that became boring and I was experimenting with everything. O... Read full Story
shemale lover 2011-12-01 4,826 gay male oral
66%
A Night Out To Remember Part 2
Decisions... decisions... we all make decisions everyday and most of them are simple easy decisions. Some may take hours, some take seconds and some are made before we even know it. Some decisions carefully planned and some have planning at all. Some decisions are between several choices and some ar... Read full Story
shemale lover 2012-04-20 2,936 anal sex Cumshot Sex Toys
90%
Gali's Surprise Package
Chapter One Gali sat in the front row of John's class with her legs crossed, raising her skirt and revealing her garter. She had sat there since the start of a new school year, and it was her seat for the rest of the year. She'd taken Beginning English Literature from him last year, and she was a... Read full Story
shemale lover 2012-06-02 6,848 anal Big Tits Cumshot facefucking
100%
Fantasy to Reality
I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn'... Read full Story
shemale lover 2012-07-02 4,168 Cumshot Fetish deepthroating crossdressing
85%
My Dominate Spanish Mistress Part One
Chapter 1: Should I even put this in chapters? I have always been somewhat of a sub. My previous girlfriends have never really inspired me to go any further than the regular sex acts, missionary and such. None of them have been shy about telling me about my sexual performance, they all seemed to sa... Read full Story
bruceclark 2012-07-28 4,347 Blowjob Big Cock facial domination
80%
Brazilian Discovery Chapter 4
John, the husband of Susan (see Susan and John series) has travelled to Brazil for a one year training session. Mr Gupta has sent him as the pretty little Joan, in the hope he would lose any interest for Susan and leave him totally free to deal with his senior accountant! The corset maker had bee... Read full Story
shemale lover 2012-08-25 4,160 cum oral huge cock brazilian
100%
Girly
It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. ... Read full Story
shemale lover 2012-09-11 4,423 Small Tits Cumshot fingering oral sex rimming foot fetish
71%
Trucker tales
It was a really hot day down in the panhandle of Texas My dispatcher had pushed me to get down here for a load of potatoes and I had been driving for about 10 hrs strait and I was running close on my 70 also so I just wanted to get to the farm and get the load on and then find a long shower and a ho... Read full Story
shemale lover 2012-09-15 4,615 Cumshot sucking fingering ass fucking
66%
Discovering Mistress Sarah's World Part 9
Part 9 -- The Final Part Chapter 23 Leaving Work Josie's last week at work and concluding week of his normal life went quick. At work he spent time getting things in order for the next unlucky person to take over his job. Mentally he was already checked out of work. All he cared about was gett... Read full Story
shemale lover 2012-10-04 3,983 Fetish ass licking domination
57%
Futa's Are Real
I am writing this letter as my account of truth in the legend of Futa girls. Now I should write a little about me first. I am 26 now but when it started I was twenty-two. A college jock and loved women. I would go to all the parties and college bars and hang outs. I was good looking guy 6'3, 276lbs.... Read full Story
shemale lover 2012-12-14 5,433 Big Tits Cumshot sucking jerking
96%
New Horizons
Pete always was very open sexually speaking. "Don't knock it if you haven't tried it" was his watch-phrase when it came to sex. Being alone in a faraway land had just emboldened him a little more. Lately Pete had found himself fascinated by transsexuals whose pictures he'd seen on the ... Read full Story
shemale lover 2012-12-23 4,931 sucking dildo ass fucking ass fingering handjob
93%
New School, New Life
Part of my father's job is on-campus recruiting, so when it was time for him to spend a week at the university where I was enrolled for the following fall, we decided that I should go with him and familiarize myself with the campus. We left on a Friday morning to ensure I'd have a full week on ca... Read full Story
shemale lover 2013-02-06 8,778 Teen (18+) Crossdresser Cumshot sucking ass fucking
88%
Ivana Pushing Sissy's Limits
"You look ravishing," my wife Ivana said as I stood before her in a short red velvet dress with white tights and black Blahnik mary janes heels. She walked over to put a hair band in my long black hair. It was down to my shoulders now, flat-ironed straight. We stood together in front of... Read full Story
shemale lover 2013-03-19 6,728 Crossdresser Cumshot sucking Creampie ass fucking
76%
She didn't see it coming
I had seen her at a stop light while driving around looking for a spot to eat. She drove a red Pontiac Sunfire, the convertible kind that no self-respecting man would be caught dead in. She was gorgeous, at least from what I saw from my elevated platform of the SUV I was driving. She was petite, ... Read full Story
shemale lover 2013-07-17 5,160 hardcore oral sex big boobs kissing shemale sex
92%
A very special lady
I knocked at the door, unsure of what to expect. Living in a big city for the last year, where I didn't really know anybody, had certainly put a crimp in my sex life. Where I used to live, in a much smaller town, during my high school years, I'd been able to get my dick into many tight, warm and wil... Read full Story
shemale lover 2013-07-18 6,067 Stockings anal sex Shemale Fucks Guy ass licking ass fingering
96%
My First Time as a Girl
I was hoping to hook up with a straight guy. I have 2 b*****rs and a s****r I’m the youngest and a Freshman in high school. Always been fem preferred to play with my s****r and her dolls. My dad is an ex-marine. Tough guy. My b*****rs are following in dad’s footsteps, military orientated. I‘m a b... Read full Story
shemale lover 2013-12-07 6,629 tranny Crossdresser Creampie ass fucking cd
92%
Lucy's Change chapter 2
Chapter 2 Sunday was even darker and rainier than Saturday. We woke up still holding each other from the night before. We were spooning. Lucy’s warmth felt so nice against my back. Her legs only reached halfway down my calves, and I could feel her rubbing my legs with her toes. I could tell that sh... Read full Story
Alex1090 2015-03-31 6,392 anal big dick tranny shemale ass fucking
93%
CD Jinn College Experience
So being a secretive cross dresser is very difficult to do with roommates. I only dress when I know that no one will be around for hours I check class schedules and ask what everyone is doing all the time so I know when my chances to dress are. I was planning on dressing over the weekend. It was p... Read full Story
Jinn.V23 2014-03-27 6,034 Crossdresser Cumshot ass fucking domination cd
100%
Double Anal With a shemale
....He answered the door and there she was beautiful as ever. He had just paid 500 dollars to have a transsexual e****t come directly to his door and greet him. She had on a long pea coat and thigh high boots. When she took the pea coat off all she had on was a one piece swimsuit. Her tits were a 36... Read full Story
shemale lover 2015-04-29 5,412 tranny suck Big Cock ass fucking dp precum
96%
My First Sex with Tgirl
This is story about me......Hope you all enjoy it I was 19 years old and itching to have sex like every normal teenager. Years of jerking off to porn had only expanded my imagination and made me want to fuck a girl even more. I was turned on by just about anything and everything except gay porn. Ev... Read full Story
sach 2016-02-16 13,550 first time tranny ass fucking guy on shemale mutual suck
97%
Tiffany
The first time I met Tiffany I was amazed. She was a gorgeous brunette, about five feet six inches tall, shoulder length hair, nice firm, round tits, and an ass to die for. It was late in the evening when I got off work and uncharacteristically, I decided to stop in at Varsity's for a drink. ... Read full Story
TgirlLover4Life18 2018-05-18 18,646 first time Big Cock virgin woman shecock transgirl
100%
Seattle Weekend Part 2
I awakened to the smell of coffee and this beautiful silhouette of a girl standing at the window watching sunrise. I could see through her lingerie the beautiful breast and nipples, and the silhouette of her TG butt which was so sexy looking I was getting hard. I joined Gwen at the window wrapping m... Read full Story
Jon Paul 2018-08-13 6,791 Big Tits Cumshot Bareback Ladyboy Guy Fucks Shemale cum in mouth
100%
yes, Mother give it to me
"Do your fucking job right, Henry! Jesus Christ, what are you, five years old? If I ever have to call you in here again, you're done! You hear me? You'll never work in this business again! Now get the hell out of my office." Mona could feel every set of eyes on the floor anxiously awaiting the pi... Read full Story
ASSEaster5678 2018-11-28 12,811 Guy Fucks Shemale
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 4,706 Amateur Cumshot Shemale Fucks Guy threesome Blowjob Big Cock
100%
I was a Top before this experience
She was tall, 6 feet probably, a white colombian beauty, green eyes. Pretty gym body, strong but feminine, don't know how that works, but this was a work of art. Sweet but commanding voice, you know, similar to that voice that tells you that it's recalculating your GPS route or to turn left right no... Read full Story
Mizty 2022-11-03 6,568 Amateur Cumshot Shemale Fucks Guy Blowjob Big Cock Homemade
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 6,794 Crossdresser Lingerie domination Sex Toys femboy forced webcams
100%
Hung Alessia Travestita meets MILF
Hung Alessia meets MILF with Giant Clit Several days ago, Alessia a beautiful English Transvestite met a tall slim sexy Canadian woman named Sandra on the internet. They were captivated with each other's nude bodies and genitals. They immediately engaged in a video sex session together. Sandra fu... Read full Story
darrell 2023-08-13 4,239 anal Big Cock deep throat cock sucking milf fisting pierced cum shot muscular big clit Swallowing Cum Hard Body
100%
Shemale Pussy
My wife Carol loves to bring she-males home for me to suck and fuck while she watches and masturbates. She works at a club that has she-male entertainers and there's nothing like having a hot she male straddling your lap so you can oil her smoothly shaven body down with baby oil. It's even better... Read full Story
shemale lover 2011-08-25 4,460 first time shemale Big Cock