Sort by
Relevancy

Free Stories

100%
TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
SpankydeBautumn 2021-03-01 2,909 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 5,122 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov 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 4,129 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
100%
My story; don’t know which one... English version (1)
I notice that the're not many french language readers so have I decided to publish an English version End of the 80s; a tough time for a young reporter travelling thousands of km's for a crumb of titbit. A new event and more pressure every day for me. Seeing me in this floundering state during a ... Read full Story
hippocampus_171 2022-07-21 3,808 Small Tits Crossdresser Amateur Bareback domination Sex Toys Mature Homemade
100%
Groped on the Bus!
In real life I do not crossdress in public, I am not yet comfortable being my true transgirl self, I wear normal men's clothes and I look like a guy. So I look very different from my persona here. So...there I was standing among dozens of strangers at a bus stop. I kept looking up from my phone ... Read full Story
Chrissy Tunnell 2023-03-22 5,373 Small Tits Masturbation Fetish Big Cock Ladyboy Guy Fucks Shemale Frottage
80%
my new life with my sister-in-law
Yesterday, I went to visit my brother's newly-divorced ex-sister-in-law in her brand-new apartment. It was meant to be a friendly visit and an opportunity to discuss her new start in life. To describe her to you, she's a slightly chubby woman in her forties, blonde hair, blue eyes, very charming wit... Read full Story
DicksFly 2024-02-06 7,259 Amateur Fetish Blowjob blonde Lingerie Sex Toys Mature big ass Homemade
50%
My Parisian escapades,
My Parisian escapades, During my many business trips to Paris, I never miss going to see my friend. Sabrina is a Cuban transsexual that I have known for several months. With her, I can let go with complete confidence and live my fantasies. I am one of his friends and lovers who give him the ... Read full Story
sandratvtg 2024-06-25 2,820 anal Stockings Shemale Fucks Guy Fetish Lingerie Sex Toys sissy wig gode pumps rosebud silicone breast split panties
80%
Wild Night Of Sexual Pleasures
My gorgeous wife and I have explored every possible when it comes to hot sex and wild times. We've done every kinky thing that you can and would never imagine along with swinging with couples that we know and some we don't. We've enjoyed and shared the pleasures with horny lesbians hot bisexual guys... Read full Story
shemale lover 2011-08-13 4,030 sucking transsexual bisexual
100%
Amy Finally Lives Out Her Fantasies Part 3
Amazing the things one finds when on their significant other's computer. Benjamin -- or should I call you "Kyle"? -- you really should be more careful with hidden files, cookies and predictable passwords. You, along with anyone who reads this story (including you Dave), are reading t... Read full Story
shemale lover 2011-09-15 2,730 asshole orgasm ass fucking
80%
Alpha Gamma's Secret Part 3
-7- "This has been an important and exciting year for our sorority," said Jessie, House President, to the assembled sisters of the Northeastern University chapter of Alpha Gamma Tran. Today was a very special day. It was the annual Commencement Ceremony which marked a successful en... Read full Story
shemale lover 2011-11-03 3,921 transsexual orgasm ass licking
100%
Club sex the 25yo
There’s a very special private club around, it’d meetings take place in a very secret place. It takes a lot to gain membership. You have to either have a lot of money AND a friend in the club OR you have to take part in the ceremonies for at least a year. Also you have to be willing to b... Read full Story
shemale lover 2011-12-10 5,199 anal Group Sex lesbian
100%
Headmistress' Favorite Sport Part 10
When Denise came to she was lying in bed. She had been washed and she could no longer feel the annoying diaper rash. In fact she felt fine, clean and well rested. On her feet were what turned out to be black Oxfords with seven-inch heels. Her ankles were in steel cuffs and connected by a eight-inch ... Read full Story
shemale lover 2011-12-13 4,783 torture toys bondage and discipline chastity belt
80%
Headmistress' Favorite Sport Part 11
Denise lay in the trunk of the car, her legs tied together with rubber straps waiting patiently to see what would become of her. She had long since relinquished all control over her own life and knowing that she was just useless sissy-slut made it easy to accept that whatever was done to her was pro... Read full Story
shemale lover 2011-12-13 6,310 domination torture toys chastity belt
0%
Just a Sex Story
I just love to write stories about various types of sex. I love to write and masturbate as I write! The fact is, in fiction I have fucked everybody around and many who are not around. In truth I have even fucked you! And I am going to do it again. First unbutton my shirt and jeans then slip them off... Read full Story
shemale lover 2012-01-15 2,940 anal Big Tits shemale
100%
THE WONDERFUL ADVENTURES OF MISS K: QUEEN OF THE ROAD
Miss K drove the car through the Midwestern countryside, enjoying the early spring breeze that leaked through the SUV's window as it blew through her platinum blonde hair. Her tits were held up by the tight, white, midriff-baring top she wore that stopped just below the lower curve of her tits... Read full Story
shemale lover 2012-01-28 4,190 licking sucking fucking Sex Toys
0%
A Good Shower
Where do you start describing an evening like this? First is a description of us. My wife of five years is still the girl of my dreams. Putting aside her sparkling personality, she still meets all my standards for a perfect ten. I like them small, she is 4' 10', blond and built just right. I towe... Read full Story
shemale lover 2012-03-08 3,277 anal sex oral sex Sex Toys
0%
A Long Friday Night
Labor Day weekend was coming up. It is the weekend that I let myself go. On this weekend I do something that I save for most of the year. I just do it for myself. This year I was going to try to get a date with a young lady called “Lee”. Let me tell you something’s about me first. ... Read full Story
shemale lover 2012-03-17 3,824 sucking Asian domination jacking off
100%
A New Life Part 2
The next few days I spent packing and repacking. I would need to watch what I packed as I was taking a plain to meet Sara and Tom. Most if not all my toys would either need to be mailed or stay behind. I had packed five suit cases all of them filled with female clothing and shoes. My carry on was pa... Read full Story
shemale lover 2012-04-13 3,249 Cumshot Sex Toys cum swallowing sissy
100%
A Night of Makeup, Cock and Cum
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further,... Read full Story
shemale lover 2012-04-18 4,929 Cumshot jerking off domination Sex Toys cum swallowing
100%
Every Year
Imagine me. A slim eighteen year old boy, dressed. I mean Dressed. Dressed up that is, in my sister's clothes. I felt good, very good. In fact I felt incredible. I had done this several times before when my parents had been away but never to this extent. They were away for two nights, visiting Uncle... Read full Story
shemale lover 2012-04-22 5,737 Cumshot oral sex deepthroating crossdressing
75%
Amy & Hope
My name is Amy but my real name Anthony and I turned 21 and started my first step on becoming a woman I decided to get some breasts for my birthday since I'm becoming a woman so after the surgery I felt more like a woman I was 5'9 weight120 and had long brown hair and some perfect size tits they was... Read full Story
shemale lover 2012-04-25 3,605 Big Tits cum transformation oral sex vaginal sex
100%
Fuck Me
My life had become pretty boring and my sex life non-existent. The women in my life had all proven themselves to be untrustworthy, transparent and superficial. I was taking a break from the world. I just wanted to sit at my bar stool, get drunk and smoke my Cohiba until I could drink and smoke no mo... Read full Story
shemale lover 2012-05-08 4,540 first time Cumshot oral sex cum swallowing
100%
The Bitch Bites Back
Pamela stood huddled in the dark doorway, halfway down the back alley. It was cold and a light drizzle had settled in, the sheets of fine rain just discernible in the dull light of the single working lamp halfway down the alley. Pamela was in her mid forties and fighting a losing battle against t... Read full Story
shemale lover 2012-05-12 7,690 anal sex Cumshot oral sex wanking cum swallowing
33%
A Rare Treat
It was late. No one else was around. She could feel her pussy getting hot before she even put the movie in the DVD player. It was a lesbian flick, no plot, just hardcore girl-fucking. Justine always loved watching women fuck each other. Perhaps it was because she could never do it just like they cou... Read full Story
shemale lover 2012-05-27 2,562 Cumshot oral Sex Toys porn
100%
A Schoolgirl Story Chapter 2
I must apologise for the amount of time that it has taken for the second chapter of this story to come out. I have to admit that I had kind of abandoned it, but all your lovely feedback comments made me decide that I couldn't leave this one hanging. So thank you to everyone who wanted more of Wendy,... Read full Story
shemale lover 2012-06-05 8,736 Group Sex Cumshot oral sex assfucking
80%
Daniel, Dani, Dana Part 2
Looking in the mirror as I drove the highway, the new me felt and I thought looked great. A new hair color with the old one the trim, my face looked smaller and even more feminine. I never had this freedom at home and hated the idea of going back there. Final exams were all that was left to shed the... Read full Story
shemale lover 2012-06-08 3,863 anal sex Cumshot Fetish crossdressing
100%
Birthday Present Chapter 3
Her Side We were all laying around the den floor in a state of partial dress, our undies scattered about. Each of us had pretty well messed up her makeup with our love making, including Victoria. She lay back against the sofa with her dress barely covering her spent penis, a satisfied look on her... Read full Story
shemale lover 2012-06-17 3,135 Cumshot Fetish oral sex feminization
100%
Feminized by My Girlfriend Chapter 2
I followed Brook and Linda out of the spa onto the sidewalk and I looked around for the limo but it was no where to be found. As the girls started walking down the street and talking to each other, I asked where the limo was. Neither of them responded and just kept walking. I followed behind as clos... Read full Story
shemale lover 2012-07-14 13,937 Fetish oral Sex Toys feminization
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 5,508 Cumshot fingering Sex Toys feminization
100%
Brazilian Discovery Chapter 3
Chapter 03: Partying in Copacabana On the Ipanema beach, Barbara and Joan were joined by Tereza and Consuela. The beach was less crowded than the Copacabana one. Tereza pulled down her shorts and her T-shirt to appear in a quite hot red bikini, an uplift bra that was supported only by a band arou... Read full Story
shemale lover 2012-08-25 3,792 Group Sex Cumshot oral sex Sex Toys
100%
Quick Fix
My anticipation couldn't be expressed in words. It had been a while since I'd had a visitor to my apartment. The last experience had ended quite well, with the bed sheets being more than a little tussled up. I was preparing myself with an erotic movie. The sex scenes always turned me on, my ... Read full Story
shemale lover 2012-08-30 2,854 anal sex Cumshot Blowjob jerking Sex Toys
100%
Porshe's Escapade Chapter 3
Hi all it's Porsche finally back and able to tell you about another escapade. My male half has been so busy lately with work and vacation etc. that Porsche just hasn't had time to play. So for my first free day in a long time I decided to be Porsche all day long. I got out of bed and droppe... Read full Story
shemale lover 2012-09-05 3,270 Crossdresser Blowjob Sex Toys double penetration
40%
Kitten: A Pantyboy StoryKitten: A Pantyboy Story
It's easy now to look back and play armchair psychiatrist and see where my fetish for school uniforms and cute cotton panties started, but it wasn't until I met MISTRESS that I realized exactly how deep that fetish was ingrained in my mind and soul. Mistress knew I was a pantyboy after the first ... Read full Story
shemale lover 2012-09-10 7,255 Crossdresser fingering Sex Toys handjob 69
100%
Brian Becomes Brittney
My name Is Brian or at least it was the first 18 years of my life. Brittney is my new name.... All of this started when I was just out of high school. It was the beginning of the summer and I was feeling great. During the summer I was planning to do a study abroad program for a year before colleg... Read full Story
shemale lover 2012-09-21 4,909 domination oral sex Sex Toys
100%
Working with Trista Chapter 2
Day 3: That morning I was awakened as my phone rang; Trista was calling me telling me it was time to get up. She said that she would be over shortly. I hoped it was to let me out of the chastity device. That moment couldn't come soon enough, and neither could I! A few minutes later Trista knoc... Read full Story
shemale lover 2012-09-24 3,957 sucking cum Sex Toys
100%
Womanhood for Jenny Chapter 3
Jenny woke sore and stiff from her 'engagement party' session with Master last night. Padding silently to the bathroom, she began her daily ritual: douche, shave, and shower. Admiring her new implants in the mirror, she was proud of her feminine curves, and the bruises and welts of Master's 'loving ... Read full Story
shemale lover 2012-10-08 3,937 oral sex big boobs Sex Toys
90%
Brian Becomes Brittney Chapter 1
My name Is Brian or at least it was the first 18 years of my life. Brittney is my new name.... All of this started when I was just out of high school. It was the beginning of the summer and I was feeling great. During the summer I was planning to do a study abroad program for a year before colle... Read full Story
shemale lover 2012-12-21 5,375 Teen (18+) Crossdresser domination Sex Toys ts
94%
CD and BBC Gangbang 1
My name is Mike, as a "Gurl" I go by Fiona. I am a gay man, mid thrities, white, 5' 9' 165, reasonably handsome, both in and out of women's clothes. One of the ways I express my sexuality is to dress as a woman and get fucked by other men. Preferably in a humiliati... Read full Story
FionaFucked 2014-10-27 14,220 Group Sex gangbang Interracial cd sissy
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 7,844 Crossdresser hardcore ass fucking cd
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 18,286 big dick anal sex suck Blowjob cock sucking workplace
91%
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 13,682 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 5,361 Teen (18+) Amateur Cumshot Bareback Creampie Blowjob Big Cock Asian Ladyboy domination Guy Fucks Shemale cum in mouth
92%
The trip
I was at work and they decided that some of us had to go to Florida to work on some problems so I was picked. I went home and packed and made sure to pack some of my sissy outfits also because I would be in a hotel for 7 days and have the room to myself it was perfect. The next morning me and the ot... Read full Story
crossdresser55 2019-09-18 12,441 Stockings Crossdresser Shemale Fucks Guy Fetish Sex Toys
100%
my journey down the rabbit hole
The bathhouse was busy tonite, there were at least 20 or more men there when I got in , I paid for my room and walked in past the heavy buzzer controlled black steel door, it slammed tight behind me. casting a cool draft of air that trailed down the small of my back and fluttered over my enama clean... Read full Story
badbadboi667 2020-12-23 6,186 Crossdresser Amateur Group Sex gangbang Interracial Ass to Mouth
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 12,876 Small Tits Crossdresser Cumshot Masturbation Fetish Blowjob Lingerie Shemale and Girl cum in mouth
100%
First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
Trapbomb1 2022-07-29 7,108 Teen (18+) Crossdresser Bareback Creampie Blowjob Big Cock virgin virginity sissy cum in mouth double anal sissy slut virgin ass
83%
My day after forced feminization - fetish
My typical day starts with getting dressed in one of my favorite outfits. Short minidress, thigh highs, thongs, a corset and 6 inch Stilettos. I started wearing a corset to get my waist tighter and transition too the perfect hourglass figure. After Breakfast typically one of my wife's friends stop... Read full Story
TRTRAIN 2023-04-22 5,191 solo Amateur Masturbation Fetish Ladyboy Lingerie domination Sex Toys Homemade
100%
It Started by Waxing and Ended Up Something Else
The Best sex I ever had? With a 29 year old female about 7 years ago, (2017) Her alleged name was Ashlee, How did I know her? For about 3 years I was paying for a total body etc. professional waxing, with Karen who had a business in Lincoln. People have not lived until they have gone through... Read full Story
Linda Tiffany Vista 2024-05-09 3,924 Crossdresser blonde Shemale and Girl domination Sex Toys small cock Homemade
50%
An alumni gathering like no other; 2/2
... I opened my eyes, sobered up from the alcohol and my lust. Simo had already left. I had to get ready for the party, and I had to do it like a man! BUT, slut that I am, to make my breasts more prominent under my dark purple tank top, I tightened a transparent strap around my waist. You never kno... Read full Story
hippocampus_171 2024-06-16 2,564 anal Amateur Creampie Blowjob Sex Toys Mature small cock big ass cum in mouth
100%
I Believe
I Believe I had just started my senior year in college and was in my 3rd year of transitioning from a male to a female. I couldn’t start in high school so when I graduated and I started college I started as Nikki. The first three years working on my communications degree I used to see people goin... Read full Story
ShelleyParker 2024-07-08 3,147 Bareback Big Cock Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
66%
Outdoor Pleasures
Every evening of our holiday we would all dress up and head to the nightclub, the glamorous entertainment was for the young and old and it was great to hear the oldies applauding alongside the young ones… One night when we headed to the nightclub there was a sign announcing the entertainme... Read full Story
shemale lover 2011-08-13 3,088 anal sex asshole cum
100%
Adventure with a Couple
A friend of mine, who thinks that i lead an exciting sex life (okay, i DO, lol) has asked me to relate an incident from my experience where i had a session with a couple. So, R, here goes. i guess i should relate a bit about myself, so that you understand how this affair took place. i am a 41 yea... Read full Story
shemale lover 2011-10-15 4,760 Big Tits asshole Uniform Sex Toys
75%
Encyclopedia Erotica By The Fan
It was a normal-looking enough place. A small town in California. Looking at it, no one would ever guess it sat on the hellmouth. The Mouth of Hell. A portal to a multitude of dimensions filled with horrors and wonders. Many things came to the Hellmouth, drawn by its power. Vampires. Demons. Mon... Read full Story
shemale lover 2011-10-19 4,597 asshole orgy Sex Toys
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 21,377 Blowjob perky tits handjob titfuck
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,933 Creampie Big Cock ass fucking
91%
Lake Surprise
After finals of my first year in college in a northern university, I was ready for some real relaxation back home in the warm south. During finals I had started thinking how nice it would be to borrow my brothers boat and hit the lake for a week. I talked my roommate into making the trip home ... Read full Story
shemale lover 2011-12-08 10,889 anal Group Sex Creampie