Sort by
Relevancy

Free Stories

50%
The Chronicles of Drodge Mallea
Drodge awoke feeling fuzzy headed and stiff. Actually, "awoke" wasn't quite right -- "came to was more like it. She sat up in the lavishly furnished boudoir, stretching her athletic 6-foot frame as she did. Running a hand though her short, thick copper locks, she slipped out of the... Read full Story
shemale lover 2011-10-24 3,153 Cumshot shemale Big Cock
100%
Young Hercules: Versatile Stud by The Fan
Prometheus Academy. It sat atop a hill, dominating the vast region of Thessaly, Greece. It was the most prestigious school in the area. The most famous men and women of the world came there to get their education. The sons and daughters of kings and queens, ... Read full Story
shemale lover 2011-12-01 3,447 anal Creampie jacking off
100%
Sissy Training
This is a true story, looking back it is hard to believe it actually happened, but it did. I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We&r... Read full Story
shemale lover 2012-03-12 8,306 Group Sex Fetish bdsm
50%
Escapade
I'll never forget Homecoming this year. My boyfriend, Blake, came by my dorm to pick me up around 6 pm. He was in a very excited state and I could tell something was in the works. I asked him why he was so hyper and he told me that he was about to win the sex escapades, which was an annual challenge... Read full Story
shemale lover 2012-04-19 4,441 Cumshot oral sex deepthroating sissy
100%
Exotic Escapades Chapter 3
The smell of wood and coffee filled the quiet house as Tammy slowly picked herself up from a plush couch. Daggers of sunlight blinded her eyes as she eventually got on her two feet. Her body ached, and she noticed a small pink bandage on her left leg. The terror and pain of last night shook her as s... Read full Story
shemale lover 2012-05-05 3,132 tranny Creampie Big Cock Ladyboy fingering oral sex
100%
A Revenge Fuck Part 2
Frankie had been a great sport about the entire affair. She had taken me in, she'd showed me how to become and be the beautiful woman, Josie- she had completely made me who I was, even against her will. And then she was also there to shoulder support in my emotional crisis when things did not work o... Read full Story
shemale lover 2012-06-03 4,980 anal sex Creampie shemale oral sex
100%
Shemale snapped
Camilla took a few steps out the door of her balcony to get a feel for the temperature. Thankfully it was cool out. It had been a hot day, which meant a cool night was welcomed. She closed the door and pulled out a pair of gold hoop earrings. She was suffering from a mild case of the jitters. The... Read full Story
shemale lover 2012-06-21 6,392 anal sex Creampie shemale Big Cock
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 4,263 Cumshot Fetish deepthroating crossdressing
100%
Darling Nikki
Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She ... Read full Story
shemale lover 2012-07-15 7,548 Cumshot oral sex Latex sissy
100%
At Jake's Cabin
Jake and I had been secretly seeing each other for about a year. We took every chance we could get to go and fuck. Jake’s famly had a cabin on a private pond in northern Minnesota. He had asked me to go up there with him for spring break. He told the fam that it was a guy’s weekend to fi... Read full Story
shemale lover 2012-08-17 3,217 anal Cumshot Creampie threesome oral
50%
Devoted to Pleasure Chapter 2
Kelly was so bored when Janice was at work. She truly preferred to spend as much time as humanly possible with Janice. It seemed as if she enjoyed everything she did more when they were together. Because their days off and hours didn’t always align, Kelly often found herself looking for some w... Read full Story
shemale lover 2012-08-22 2,804 Cumshot oral foot fetish
95%
T-Girl University
Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for ... Read full Story
shemale lover 2012-09-05 14,955 Cumshot Masturbation Blowjob ass licking redhead
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 2,752 Cumshot Masturbation Blowjob Big Cock fingering
100%
Alexis Chapter 5
Mr. Hughes opens the door, and there stands his nephew Kyle. Just earlier today, he wouldn't have even thought about my existence; I just would have been that weird kid that doesn't ever talk to anyone. But now, I have all of Kyle's attention. His eyes are moving up and down my body, checking me out... Read full Story
shemale lover 2012-10-06 4,630 anal sex sucking Creampie kissing
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 6,452 Fetish oral domination Sex Toys sissy
100%
An Invitation
"Oh come on,Sarah. There has to be a way." An innocuous enough statement, but that's how it all started. I'd just received an invite to Cressida's annual Christmas party which, maybe not on the Hollywood A list, was within the cognoscenti an occasion not to be missed. The soirees of ... Read full Story
shemale lover 2012-11-16 4,723 Fetish oral sissy
75%
The dark elavator
I was working on a inportent computer tech. when this women send me a pc to pc message with a picture of a women say want to tast me baby. i look up and she says well how about it and winks i goto get lunch so i goto the elevator but it full. i dont want to take the red elevator its lights fliker... Read full Story
shemale lover 2012-11-18 3,033 anal sex sucking Creampie rimming
100%
Westward bound cum slut Chapter 2
Again I'm on the big bird headed out west for another fling. This time is going to be way different though, the players have increased, not to mention both sexes. The tale unwinds in the same fashion as the last trip out this way, the plane flight was long and boring, and being very nervous didn'... Read full Story
shemale lover 2012-12-16 3,696 anal Group Sex sucking Creampie cum domination
92%
Proud To Be A Sissy Chapter 6
It was still early and I wanted to enjoy the feeling of being dressed in my shear hose and garter belt, tiny g-string panties and matching bra and the form fitting shiny black mini dress that barely covered my stocking tops for as long as possible. So I spent some time doing some domestic chores and... Read full Story
shemale lover 2012-12-24 6,414 sucking domination ass fingering deep throat cd
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,508 Crossdresser sucking Big Cock ass licking big boobs
100%
A Night on the Town: Part 3
I woke up like I do most mornings, naked, in Gina's arms, her breasts pressed into my back, her semi-erect cock pressed between my ass. I laid there, thinking about the night before, smiling. Soon, I needed to go to the restroom, and gently rose, making sure I didn't wake her. I wandered out of my r... Read full Story
shemale lover 2013-05-31 3,557 Cumshot suck Creampie threesome ass fucking
100%
Roadtrip - Part One
My vacations started in five minutes, and I couldn't wait to get out of the office. I had been counting the days impatiently for 2 weeks. Unfortunately, I had made no plans but that was ok, I was going to sl**p late for days! A last minute customer call and I was walking down the hall and out the do... Read full Story
shemale lover 2013-05-31 5,717 Big Cock jerking ass fucking Interracial cd
83%
MY FIRST TIME WITH A SHEMALE - 2
DEAR READERS I DON’T KNOW IF YOU LIKED MY FIRST STORY AS THERE WERE NO COMMENTS ........ !!! After we finished our late dinner in the very cosy position she whispered “wanna have some wine honey?” I replied “I’d love to”. She got up leaving me sitting on her bed and poured two large glass-full of... Read full Story
Lisawantsu7 2014-09-02 6,725 hardcore Creampie Big Cock ass fucking Shemale and Girl
100%
I FIND MY ROAD IN SYGKROY
My name is Anastasia, although the real name is Nick. As you can see I'm a decent boy day, a normal relationship with girl (not so normal, but that another story!), Sociableness and not effeminate at work and generally to the outside world. But when you go home and my girl is missing, I beco... Read full Story
ANASTASIS CD CRETA 2014-12-03 4,023 first time Creampie Blowjob ass fucking 69 cd
69%
Motel Blackout
I always enjoy my sales trips. The trips fit into my crossdressing lifestyle and the thrill of being in a different town and different people. After a long day on the road, I had just checked into a motel just about 30-miles outside of Nashville, TN. For my overnight trips, I always bring my spe... Read full Story
browncherrygurl 2017-05-25 18,311 anal Crossdresser ass fucking sissy forced
76%
Louise's Bedroom
The dark and humid night consumed the street surroundings, the rain pattered softly against the car window as Scott pulled outside Louise’s house. Louise had never agreed to let Scott visit before and he knew that this would be the only opportunity to make a good impression and be with her in the fu... Read full Story
Master VeeJay 2017-12-12 9,558 Amateur Bareback Creampie Blowjob Guy Fucks Shemale Mature
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 13,589 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 5,291 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
100%
MY First Time with a non-binary/cross-dresser
After I had graduated high school but before I had left for college: I was hanging out with a friend and a friend of theirs at their friend’s house. For the story let’s call my friend Dan and his friend Charles. We were watching some movie on Charle’s (parent’s) big TV. Charles gets up eventually an... Read full Story
ghostpeople 2019-03-12 7,267 first time Crossdresser Amateur Group Sex Cumshot Bareback threesome Frottage Homemade sissy blow job condomless
69%
Sissy School
I arrived at the school at 8AM for the start of my new life. The school had promised a lot when I saw their website but I wasn’t quite sure what I was in for. I had arrived dressed in male clothes with none of my belongings as I had been instructed to on the website. I walked through the gates into ... Read full Story
Sissysophie780 2019-07-04 19,391 humiliation schoolgirl sissy slut punishment School uniform
90%
Saving My Marriage
I love to write Erotica. For story requests please send me a private message or email noirenoire10@gmail.com It was our anniversary. Today made five years that my wife and I have been married and we were taking a road trip to celebrate. I chose our destination but I let her choose all of our a... Read full Story
therefill05 2021-02-16 6,288 Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob Big Cock Ebony domination Sex Toys cum in mouth
80%
Group Sex
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-04-19 3,398 Group Sex Cumshot Bareback Creampie Shemale and Girl Guy Fucks Shemale cum in mouth
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 3,756 Crossdresser solo Amateur Masturbation Lingerie Homemade webcams
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 6,474 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
100%
The Next Level
Nitromethane It's been a couple of weeks now since I sucked my last shemale cock and swallowed her load, and with enough distractions, it hasn't been too difficult keeping myself preoccupied and my mind off of satiating my new fixation. Still though, I do have my moments when I sit back and imagi... Read full Story
Gwapo67 2022-02-01 6,038 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock gangbang domination cum in mouth
100%
The Girl Next Door Ch. 02
derezzed Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the s... Read full Story
Gwapo67 2022-05-13 5,444 Bareback Creampie Guy Fucks Shemale cum in mouth
88%
Alex and Jon
Alex was not beautiful, but had a sexy attractiveness that most could not help but take a second look. This was the case with Jon as he searched adult Friend-Finder ads for someone that would satisfy his desires and dreams of a companion. Alex, a transgendered Filipina girl, had the bronze skin colo... Read full Story
Jon Paul 2022-09-21 5,491 Group Sex Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Ladyboy Guy Fucks Shemale cum in mouth
100%
First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... Read full Story
AllenB 2022-10-21 5,310 Amateur Big Tits Cumshot Latina Creampie Fetish Blowjob rimming Homemade cum in mouth latina ts
100%
I got anal creampied at the beach!
As soon as we got onto shore, I knew it was the perfect place. The hot sun was beating down on us and my body was tense with anticipation. Finally, we were going to be alone out in the wilderness with nobody around and could enjoy each other thoroughly. My hunky date and his monster cock were going ... Read full Story
Madison Heights 2022-12-01 5,014 Cumshot Outdoor Creampie Fetish Blowjob Big Cock Ebony Guy Fucks Shemale public bbc massive
50%
How to Convince Your Wife to Try Black Cock
I didn't write this - but it's great info for all my sissy cuckold sisters out there desperate for their wives or girlfriends to go Black. I hope all your cuckold dreams come true! There are so many stories out there from white guys who admit that they want to see their wives and girlfriends,... Read full Story
Sissy Annabelle 2023-10-07 6,130 Interracial cuckold
100%
Regina's Vagina dreams
I think I wanted to be a female from birth. I once looked through a girlie magazine out of curiosity. I had impossible dreams and I longed to trade genitalia with them. I have always fantasized about my Vagina when I was younger. It was during those times that I would drift into my own private world... Read full Story
Regina10 2024-03-01 5,694 anal Big Tits Bareback Creampie Blowjob Big Cock Ebony gangbang Guy Fucks Shemale big ass cum in mouth double anal
100%
Hot Part 1
I should have realized something was going on when it first started. I was her stepfather and Angela was about 16 years old the first time she started to hug around on me. This went on for several years until she became of age. After her 18th birthday, she started wanting me to kiss her on the lips.... Read full Story
shemale lover 2011-09-08 5,303 Small Tits anal sex Creampie
100%
His teacher, The transsexual
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
shemale lover 2012-01-31 9,873 shemale Big Cock teacher
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 3,441 Group Sex Big Tits Cumshot
85%
Crossdresser At XXX Movie
It was hot and the sun felt like it was going to melt me. I was walking home from work. I never drive that much and I just got off the bus for a fast beer. I walked past this XXX Movie house and thought what the fuck, it has air and it is so hot. So in I go. I should say that I'm somewhat Bi. Tha... Read full Story
shemale lover 2012-03-30 4,126 anal sex Creampie handjob rimjob
100%
A New Girl
Still half-asleep, I purred happily when I heard the curtains being drawn. I could hear the sound of rain beating against the outside of the window, but the poor weather was the last thing on my mind. Still barely able to believe my luck, I slid my hand down the side of my smooth thigh, delighting i... Read full Story
shemale lover 2012-04-05 4,630 fingering oral sex small breasts cum swallowing
93%
My New Girlfriend Turns Out to Be a Shemale
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 dress... Read full Story
shemale lover 2012-05-22 8,436 anal sex oral sex titjob
100%
Birthday Surprise
It has taken me months to plan everything. It hasn't been easy to make the arrangements without him finding out but I think I have managed to pull it off. I have planned what I think will be the perfect birthday surprise for him. Today, when he gets home he will find a note with instructions. Happy ... Read full Story
shemale lover 2012-06-20 4,684 anal sex Creampie Big Cock oral sex
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 4,740 Cumshot shemale cum swallowing mouth fucking rimjob
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 4,254 cum oral huge cock brazilian
87%
Uncles Lessons
In '91' during my senior year of high school my folks split up. The whole thing was a mess, with me being sent off to relatives while my mom took my younger siblings to the gulf coast to stay with her parents. They sold the house and Dad moved to be with his new future 'ex-wife' outside of Dallas. ... Read full Story
shemale lover 2012-09-07 6,270 big dick Blowjob fingering ass fuck
100%
Who's The Sissy Now?
Like many people, I was bullied in school. I was small, slender and effeminate and, as a result, was often called gay, queer, fag and sissy by school bullies. The fact that what they said was sort of true just made it closer to the bone and more painful to hear. Like many teenage boys, I was going t... Read full Story
shemale lover 2012-11-14 7,094 shemale facial oral sex
96%
New Job, New Life as as Sissy Slut Chapter 2
I was left lying on the floor, my face completely covered in cum. I was wearing lingerie and a dog collar and I had just been fucked long and hard by my "boss." My virginity had been forcefully taken. The thing is that I loved it. I loved being manhandled by this muscular man and I really ... Read full Story
shemale lover 2012-12-23 7,553 Cumshot Uniform Lingerie ass fucking domination
94%
Proud To Be A Sissy Chapter 2
As I reached down to retrieve my clothes that Mr. Clark had thrown at me there was a bright flash of light. Without thinking I turned my head towards him only to be blinded by another flash from his Polaroid camera. "What are you doing?" I asked. "Just wanted to capture the m... Read full Story
shemale lover 2012-12-23 8,067 Crossdresser sucking ass fucking domination ass fingering
100%
Proud To Be A Sissy Chapter 3
I woke Monday morning actually looking forward to what the day may hold and feeling good about myself. I felt like I was a different person and as I thought about it realized that in a few ways I was. I laid in bed thinking I did have a little better understanding of my sexuality now that was so con... Read full Story
shemale lover 2012-12-23 7,476 Crossdresser sucking Big Cock Lingerie ass fucking
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 14,299 hardcore sucking ass fucking Guy Fucks Shemale