Sort by
Relevancy

Free Stories

50%
The Sexiest Shemales Part 1
When I wake up in the morning, I wake up next to the sexiest shemale in the world...right after me, of course. I woke up this morning next to Holly, my beautiful shemale girlfriend. She was still sleeping in our big bed. The sun was shining in on our bed with our white sheets and white comforter. ... Read full Story
shemale lover 2011-09-03 2,753 anal Cumshot sucking
100%
Case of the Jealous Transsexual Chapter 2
Dee-Dee was becoming a little possessive after the 2 times that we had seen each other. She began calling me everyday, emailing me, wanting to know when will we see each other again and so on. To tell you the truth I had moved on. I had done everything with Dee-Dee that I felt could be done on a phy... Read full Story
shemale lover 2012-03-19 3,202 Group Sex Big Tits Cumshot
100%
Brazilian Discovery Chapter 1
Joan arrives in Brazil The plot from Susan and John series : Mr Gupta, the wealthy businessman had built his empire from scrap, starting from a small greengrocer shop in B'ham. He had slowly bought similar shops throughout England, federating them in a company that was powerful enough to build it... Read full Story
shemale lover 2012-08-24 5,150 Cumshot fingering Sex Toys feminization
100%
Transsexual Sisters Chapter 2
MICHELLE AND NICOLE TRANNY SISTERS Part 2: Living with lesbians During freshen orientation the girls kindly declined approaches from many men and some women. They needed to find their bearings and were not ready to reveal any hidden secrets yet. They first needed a place to stay and searched t... Read full Story
shemale lover 2012-09-07 3,922 Cumshot Creampie Blowjob Big Cock 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 3,640 Cumshot sucking ass fucking deep throat cd
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 3,816 tranny Cumshot shemale sex transexual
97%
Everything Is Not As It Seems
The ad says Femdom looking for malesub. Must be willing to follow all my instructions. Call xxx-xxx-xxxx for consideration. Well I answer the ad and am told to show up at the femdom’s home at 7:00. I arrive at the front door and am greeted by a beautiful woman. She’s wearing a low cut... Read full Story
shemale lover 2013-07-22 6,561 sex toy Cumshot dildo oral sex handjob
100%
Masturbation fantasies 2: Looking for Amanda
Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... Read full Story
ThatEroticWriter 2019-07-24 8,726 Big Tits Cumshot Masturbation threesome Frottage
93%
Virgin Slut Cravings.
There have been so many times that I have had to hide how I felt because I lived my life denying who I was. I was a closet queen who was pretending to be normal. Some might have guessed my secret if they were observant. I didn't do things that other boys my age did. I love hanging out at home like a... Read full Story
Regina10 2020-09-29 8,218 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Lingerie Guy Fucks Shemale pov
100%
TO BE OR NOT TO BE – FINAL ACT
TO BE OR NOT TO BE – FINAL ACT by Spanky de Bautumn Part 7. Sunny spent the night with Antonio and the next day they went to Mel and Shari’s for some fun. Antonio had school, so he was up and out early on Tuesday. Mel was in the shower and I was laying in bed, my mind wandering and not real... Read full Story
SpankydeBautumn 2021-03-02 2,327 Small Tits Crossdresser Cumshot Bareback Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 4,076 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
85%
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 2011-08-26 5,664 Cumshot asshole fingering
60%
A Sissy Boy is Made
By any measuring stick Greg Martin was a wimp, and a very submissive wimp at that. His wife of 14 years, Jaclyn, had discovered this even before the two of them were married. Actually, Jaclyn wouldn't have taken a second look at Greg, as most women didn't, had it not been for his submissive nature. ... Read full Story
shemale lover 2012-06-15 8,252 Cumshot oral sex sissy
80%
Bisexual Black Man's Paradise
The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... Read full Story
shemale lover 2012-06-24 5,216 big dick tranny anal sex Cumshot orgy facial oral sex
100%
Black Transsexual Gangster
Hi, everybody. How are you today? My name is Wanda Smites. Who the fuck am I? A fine-looking sister with a hot tale to tell you. I stand five-foot-eight, chubby but sexy, with light brown skin, long Black hair and pale green eyes. I've got big tits, a curvy body, wide hips and a big round ass. What ... Read full Story
shemale lover 2012-07-05 3,363 Cumshot domination oral sex Interracial
100%
Defend Each Other
San Francisco International Airport, San Francisco Ca. Main Terminal area 12:35 a.m. 16 September. Alex sat in the quiet airport terminal, fixing her lipstick in a small compact and checking her make-up, waiting for John to arrive from Japan. John had gone to Japan to convince his investor in ... Read full Story
shemale lover 2012-08-10 3,482 anal Cumshot shemale oral
88%
Call me
Shortly after I'd finished college I had a job with an import-export business whose main office was located near the cultural center. This area of the city was home to a small arts college, a large public library, several bookstores a small upscale hotel and a couple museums. I often spent my lunc... Read full Story
shemale lover 2012-08-15 4,720 anal sex Cumshot facefucking
100%
Brazilian Discovery Chapter 2
Chapter 02: First days in Brazil The tub was so large that it could have been a small swimming pool. Joan plunged into the water and started to lick Barbara's pussy underwater. When he rubbed the tip of his nose against Barbara's clit, she mightily climaxed several times in a row! Sometimes, inst... Read full Story
shemale lover 2012-08-25 3,558 Group Sex Cumshot oral sex rimjob
100%
Serving Waitress
This is the first “didi” story I ever wrote. It’s my deepest (and darkest?) fantasy. It probably needs to be rewritten at some stage because I think it’s been written too much by my male brain and not enough by my female side. The story begins….. My wife, Susan, ... Read full Story
shemale lover 2012-08-28 4,635 anal sex Cumshot Creampie oral sex
100%
Pleasantly Surprised
It was Friday night and Robert was sitting at home alone. His roommates were both out on dates, and his girlfriend, correct that ex-girlfriend, had moved all of her things out three weeks ago. It had been one of the dullest months in his adult life; four weeks of sitting in front of the television, ... Read full Story
shemale lover 2012-08-31 6,139 Big Tits Cumshot sucking threesome blondie
76%
Porn Princess
They say if you are going on a journey of revenge, to dig 2 graves, one for your enemy and one for yourself. I thought I understood the meaning of that saying, but never so much as right now. My name is Dan, and at the age of 21, I had been working for nearly 2 years as a production manager for ... Read full Story
shemale lover 2012-09-02 23,764 Cumshot Blowjob fuck fingering big boobs
100%
Working for Halloween
I stepped off the bus and walked the short distance to the 'Costumes and More!' shop. I couldn't believe I had agreed to do this, but if I was ever going to buy a car, I needed to get the money. You've probably seen them, this particular costume shop always has someone in costume out in front holdin... Read full Story
shemale lover 2012-10-02 4,558 Cumshot oral sex cum swallowing cd
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 3,696 anal Cumshot Masturbation Sex Toys
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 5,274 Big Tits Cumshot sucking jerking
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 22,551 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
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 6,600 Big Tits Cumshot Bareback Ladyboy Guy Fucks Shemale cum in mouth
90%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 13,076 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
Thai Ladyboy
One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... Read full Story
BEN437 2018-11-19 4,849 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
Seduced At The Gloryhole
I love to write Erotica. For story requests please send me a private message or email noirenoire10@gmail.com Enjoy! Golden blonde hair that rested just past her shoulder, piercing blue eyes, full luscious red lips with colorful sleeves of tatoo’d arms. Wow, she was immaculate. She locked ey... Read full Story
therefill05 2020-12-10 9,097 Big Tits Cumshot Bareback Creampie Blowjob blonde Big Cock Guy Fucks Shemale Interracial cum in mouth
100%
TO BE OR NOT TO BE – PART 3
TO BE OR NOT TO BE – PART 3 by Spanky de Bautumn Part 2. At the hotel in New York City, Sunny meets the bellhop, Antonio, and they go out for a drink when he gets off of work. The call came at exactly seven. I had woke up about five minutes before and was watching Antonio sleep. All of the oth... Read full Story
SpankydeBautumn 2021-02-23 2,302 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
Shemale Fantasy - Suck Fest
This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... Read full Story
shemale lover 2011-09-13 5,105 Cumshot jerking off pantyhose
100%
I Knew Her Secret
I had a serious crush on the postal lady, I would wait on her until I saw that she was coming and then I would either make up some reason to go outside and exchange words with her or I would watch naked from inside of my house. I know it sounds perverted but I just couldn’t get enough of her. ... Read full Story
shemale lover 2011-09-20 6,335 Cumshot asshole fingering
100%
A Close Encounter of the...
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 2011-11-13 4,826 Cumshot Blowjob massage
50%
How My Wife Became a Swinger
Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin. For the fi... Read full Story
shemale lover 2011-11-13 5,005 Group Sex Cumshot sucking doggy style
50%
The Sweetest Taboo
"Hey sis! Remember me?" Tisha Roberts stood at the door in complete shock looking at the person in front of her, the latest KaySlay CD whispering its aural presence in the background. She scanned the person in front of her, trying to figure out what was going on. The woman in front of h... Read full Story
shemale lover 2011-11-14 5,184 Cumshot cum swallowing handjob
100%
I Knew Her Secret..
I had a serious crush on the postal lady, I would wait on her until I saw that she was coming and then I would either make up some reason to go outside and exchange words with her or I would watch naked from inside of my house. I know it sounds perverted but I just couldn’t get enough of her. ... Read full Story
shemale lover 2012-04-04 4,742 anal sex Cumshot fingering
71%
Trans secretary
"Monica Barnes smoothed her skirt before entering the office of her boss, Cord Drake, the CEO of the company his father had founded thirty eight years ago! Like every other morning for the past two years, she brought along his coffee, her memo pad, and of course his copy of the morning paper! &... Read full Story
shemale lover 2012-04-30 4,056 anal sex Cumshot Big Cock oral sex
50%
A Trilogy of Trannie Tales
Terri and I had been having phone sex with each other on a telephone chat system for several days. We agreed to meet and go to my favorite park one day at around sundown, when most others would be leaving the park. Our intent was to flirt with and fondle each other around the other people, and then ... Read full Story
shemale lover 2012-07-11 3,417 Cumshot Fetish shemale oral sex
100%
Fifi La Femme: A Pansy at Last Chapter 2
Coming Out Telling our wives wasn't easy especially for me who had seduced Shirley's gorgeous hetero husband by dressing up in my wife Doreen's lingerie and make-up and offering him full homo sex as a limp wristed effeminate lady-man. It was my first experience as a queer and when Frank asked me ... Read full Story
shemale lover 2012-07-29 4,587 Cumshot oral sex sissy
92%
T-Girl Meets T-Girl
It was a silent car ride home. He looked at her, she looked out the window. She looked at him, his eyes were on the road. Neither of them broke the silence. It stayed that way until he parked in her mom's driveway. The soft-spoken young man told his girlfriend, "Goodnight Ashley. I'll call y... Read full Story
shemale lover 2012-08-29 6,020 anal sex Cumshot shemale and shemale domination blondie
100%
Porshe's Escapade Chapter 5
I'm walking through the crowded hotel lobby looking like a slutty school girl hooker, everyone's eyes are on me, and I'm being led by Jeff who is slightly in front of me holding my hand. We head to the elevator and step in just the two of us. I'm a little relieved yet now I start to get nervous of w... Read full Story
shemale lover 2012-09-06 2,548 Cumshot Masturbation Blowjob Big Cock fingering
100%
Bringing Daddy's Work Home
"Whew! I can't believe this shit." Marilyn Walker, recent high school graduate, stared into the reflection in the bathroom mirror and breathed deeply, thinking to herself about her latest situation. Here, she was standing in the bathroom of the office of some city bureaucrat whose name ... Read full Story
shemale lover 2012-09-25 6,835 Cumshot transsexual oral sex
60%
Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
shemale lover 2012-09-28 6,401 Cumshot Fetish oral sex cum swallowing
85%
Busted and Hoodwinked
INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack a... Read full Story
shemale lover 2012-09-30 5,745 anal Cumshot Ladyboy oral
100%
Always Be Closing Chapter 3
Hi, my name is Tom Jacobson but you can call me Marcy. I am 23 years old man. I'm 5'9" with light brown hair and a slim build. This is my third story about what happened on my first business trip after my luggage was lost. It all started when my coworker Tina convinced me to wear one of her spa... Read full Story
shemale lover 2012-10-17 3,547 anal sex Cumshot sucking
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 9,105 Cumshot sucking blonde ass fucking Guy Fucks Shemale
95%
A Black Tranny Fantasy
It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sl**ping with a black shemale was about to come true. She paused... Read full Story
shemale lover 2014-12-03 5,630 tranny Cumshot suck ass fucking Interracial
94%
Flight cancelled
I was on my way back from a long business trip to Chattanooga, Tennessee and deciding to hit the airport bar during my layover. As I walked up to the bar I noticed there was only one seat open. I took it. I ordered my favorite drink, an old fashioned neat with makers mark. As I sat there waiting for... Read full Story
Jsmithsub 2019-10-31 24,120 big dick Group Sex Bareback Shemale Fucks Guy Fetish Blowjob Big Cock pissing Ebony domination cum in mouth monster cock gang bang
84%
SUMMER VACATION by Spanky de Bautumn
In our house, it was a well-known secret that my mother kept her change in the top drawer of her dresser. The same drawer she kept her slips, chemises, panties, and all other satin, nylon, or lacy ladies undergarments. During the summer, my brother and I would run to that wondrous drawer when... Read full Story
SpankydeBautumn 2021-01-22 12,453 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
100%
I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... Read full Story
Madison Heights 2023-05-18 6,705 anal Shemale Fucks Guy Big Cock Frottage
100%
Ellen's Candy
Sometimes I get in the mood to suck a dick but I’ve never considered myself gay. I’m @ the very least bisexual but I don’t like to limit myself to that either because I think it restricts my sexuality. I get turned on watching all types of sexual situations that you could think of;... Read full Story
shemale lover 2012-04-02 5,062 Cumshot condom sex
100%
Neighborhood Restaurant Surprise - Kimi
I - The Meeting In the neighborhood restaurant I frequented weeknights after work, I had developed a friendly relationship with several of the college kids who worked as servers. Always having been attracted to the most feminine and petite of girls, dark, almond shaped eyes being a super plus, I ... Read full Story
shemale lover 2012-04-11 4,960 anal sex Cumshot fingering oral sex small breasts
100%
Jesse’s First Day
Jesse didn’t want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse ... Read full Story
shemale lover 2012-05-16 5,272 hardcore anal sex Cumshot
100%
Ellen's Candy
Sometimes I get in the mood to suck a dick but I’ve never considered myself gay. I’m @ the very least bisexual but I don’t like to limit myself to that either because I think it restricts my sexuality. I get turned on watching all types of sexual situations that you could think of;... Read full Story
shemale lover 2012-06-23 4,434 Cumshot shemale cum swallowing mouth fucking rimjob
100%
Your Best Damn Girlfriend Ever
There are times in a young man's life when it is so full of fun and sex that it's a wonder they survive. College is one of those times for many young men and it certainly was for me. I attended a small private collage in southwestern Ohio at a time when the world seemed to be totally focused on it's... Read full Story
shemale lover 2012-08-11 12,408 anal sex Cumshot shemale oral sex
100%
Whoring for freedom
It is four o'clock on a Friday afternoon and I have been driving for almost two hours on my way to a cabin in the middle of nowhere. According to the instructions my Mistress gave me, I still have about an hour to go. I have the air conditioner on because it is a very hot day and I have to make sure... Read full Story
shemale lover 2012-11-07 3,987 Cumshot teasing sucking off