Sort by
Relevancy

Free Stories

100%
Changling
‘My goodness!’ she exclaimed, ‘It appears that you've had an accident, youngster. You'd better come home with me so that we can make you presentable. It's quite safe, 'cos I live in the big house in the woods on the other side of the hill behind the toilets. Come along, now,’... Read full Story
shemale lover 2012-02-02 8,917 shemales Masturbation Big Cock
60%
Amy's Surprise 2: Enter Karissa
What did you think? Amy asked. Well, let's see, I started to answer, You gave me the best blowjob I've ever gotten, sucking your dick was about the best thing ever, and sharing your cum with you was incredible.all in all, I'd say it went well. Amy smiled and walked over to sit with me on the couc... Read full Story
shemale lover 2012-05-08 4,712 anal sex shemale Sex Toys
100%
Head Cheerleader Mikki Part 3 Michael is Back
To understand this story you must read the previous chapters. It's Sunday morning and I'm just waking up. I'm in bed alone. As I get up I see myself in the mirror. Still dressed in powder blue lingerie and a blonde wig. I wonder where the girls are. I leave the guest room and go into mine. I stri... Read full Story
shemale lover 2012-06-14 3,028 anal sex Cumshot Fetish
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 6,777 Cumshot Fetish oral sex cum swallowing
100%
Stranger at a hotel
This is very true,few years back my mother passed away,left me a bunch of money,afterward,i now had money,but no family,so i was wild,parting,having alot of,hot man sex,by the way,im a chubby,very fem. tan, smooth,i look, act,an love to be treated,like a girl,an love it when a well hung horny man is... Read full Story
shemale lover 2012-10-11 3,250 anal hardcore doggy style
100%
Francis Meets a Black Stud Part 5
I finally came upon a plan that I thought would make everyone happy. I would keep on playing this game with my man. I figured that as long as I was dressed like a girl, it didn't matter who he showed those videos too. I mean no one would know it was me and after all, he would be finish his vacation ... Read full Story
shemale lover 2012-11-20 3,054 cum oral sex Interracial
100%
Anna, Ted & She Male (Carley)
Returning from Anna's class reunion, both Ted and Anna were pleased with their adventures. Anna was able to again experience something really hard and full between her legs and Ted was able to again perform as he did a couple of years ago after being turned on seeing his loving wife with two other m... Read full Story
shemale lover 2012-12-13 4,361 anal Cumshot shemale Big Cock oral
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 17,577 Crossdresser sucking Big Cock ass licking big boobs
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 14,362 hardcore sucking ass fucking Guy Fucks Shemale
91%
My first BBC fuck
I went clubbing last week with my girlfriends that I work with and they recommended a hip hop club in a seedy part of town. I was alittle scared but we went anyway and well, and we were really having some fun there!!! I decided to dress like a real lil slut this night, a black minidress, lacey thigh... Read full Story
shemale lover 2013-06-06 10,101 hardcore Creampie Big Cock Guy Fucks Shemale Interracial
93%
Sissy schoolgirl and her black daddy
I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning... It was summer time. As always I spent m... Read full Story
shemale lover 2013-06-22 40,125 Teen (18+) Bareback Creampie Lingerie ass fucking Interracial cd
100%
My Greek Goddess
I'm Caroline. I'm 27 years old and I work as a solicitor in the West End of Edinburgh. I'm generally considered quite attractive, five-feet-five tall with dark blonde shoulder length hair and a pretty face, featuring big green eyes and pouty lips, and a nice figure with C-cup boobs. I've been blissf... Read full Story
shemale lover 2013-07-17 4,479 tranny brunette shemale Big Cock big boobs
88%
Tgirl trained to be the town whore to serve ALL Black men
A few years back I spent time on and off with several shall we say more dominating types of gentlemen One of them, who for this I shall call Leroy, just loved when we got together to make me totally helpless. It was our 6th or 7th meeting. Leroy and i had been chatting on Yahoo and when he f... Read full Story
__tiffanylondontv__ 2014-09-30 6,264 suck shemale ass fucking Interracial big cocks
94%
Fem Firm: Character Intro
Coxson & Dicster is a law firm made up of nothing but she males They are: Debra Coxson- 37 Debra has been a lawyer for 12 years and started the firm with her college roommate Angela Dicster 5 years ago. She's a leggy ash blond with 38D tits a great ass and a 9 inch cock. She loves to ... Read full Story
bennyx709 2015-07-29 5,539 Cumshot suck shemale oral
94%
Shemale Ride Along Part 1
I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass. Now... Read full Story
qtball 2016-08-29 12,728 anal tranny Blowjob Big Cock bj asstomouth
92%
Lady In The House Chapter. 01
A story by MicheleNylons ( Man in jail is transformed to prison slut.) How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild... Read full Story
✘Transensual✘ 2019-01-11 9,650 Crossdresser Bareback Creampie Fetish blonde Big Cock Lingerie domination Guy Fucks Shemale transvestite slut PRISON FUCKBOY prison sex Prison Bitch
42%
sexy jane story
I love the idea being a crossdresser wearing women outfit bars in panties n sexy outfit not just for the sex I love sex being on my knees sucking cocks in getting fuck by a big cock see win I was very young I had sex with 3 guys one day they ask me will I suck there cocks in I sand yes we want insid... Read full Story
45sexyjane 2019-05-27 4,419 Small Tits Crossdresser Amateur Big Tits Masturbation Blowjob blonde Big Cock gangbang Lingerie Sex Toys shemale + shemale sexy crossdresser
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,690 Big Tits Cumshot Masturbation Uniform Frottage
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 9,098 Big Tits Cumshot Masturbation threesome Frottage
100%
Liberty in Lisbon Part 3
After Olivia had so perfectly taken my anal virginity, we laid in bed cuddling, touching, kissing and her cum leaking from me. I had not been so lovingly caressed for such a long time. It was just perfect. She asked me how I was feeling. I think I said before that I don’t do deep and meaningful very... Read full Story
Rusty12 2020-09-16 3,582 Masturbation Shemale Fucks Guy Blowjob old-and-young 69 sucking
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,764 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
100%
Lola Chapter 5
Lola chapter 5 Summer vacation was coming to an end. Most of the time we had been to ourselves, mostly at home but also a couple of shorter trips. Beer tasting in Stockholm's archipelago, a trip to the west coast, overnight stays in hotels, everywhere we were received like any other couple. A fam... Read full Story
BellaBeau 2023-10-30 6,042 anal Cumshot Latina Bareback Creampie threesome Shemale and Girl Lola
100%
My girlish désires,
I am happy to spend my weekend at home to live my life as a woman. I apply a depilatory cream to my body, which I leave to act for a few minutes before going in the shower. I take this opportunity to do an enema to avoid unpleasant surprises during my girl games. Then, using a razor, I track the ... Read full Story
sandratvtg 2024-06-20 2,832 anal Stockings Fetish Lingerie Sex Toys femboy
100%
I was backstage giving blowjobs at a transsexual beauty pageant
I was backstage giving blowjobs at a transsexual beauty pageant I had this neighbor, who cross-dressers on weekends for a LGBT club. She invited me to an annual transsexual beauty pageant. Beautiful slutty shemales competing to be the official beauty queen for the club. She happens to be hosti... Read full Story
My Shemale Attraction 2024-08-07 3,825 Crossdresser Group Sex Big Tits Cumshot Blowjob blonde Big Cock Ebony gangbang domination pantyhose
50%
trans=demic
Trans-demic Chinese Flu Sam Wong read the email from Josh Epstein, the partner in charge of the fiendishly complicated real estate deal that had consumed the last three months of their lives. “You’re going to have to close this deal without me. I’m sick as a dog, and my wife just called an ambu... Read full Story
the greatest liar 2024-09-09 1,364 anal Small Tits Bareback Creampie Asian Guy Fucks Shemale small cock Ass to Mouth cum in mouth
85%
Buffy the Shemale Vampire Slayer Part 10
Buffy Summers was certainly no virgin. She'd lost her virginity to Angel, a vampire, thereby releasing him from the Gypsy curse that, as punishment for his having brutally killed the favorite daughter of their tribe, had restored his soul, that his conscience might torment him as he recalled the tho... Read full Story
shemale lover 2011-08-21 6,592 cum tgirl stiff cock
80%
How I Became Vanessa Part 1
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 husband moved to... Read full Story
shemale lover 2011-09-09 4,507 anal sex shemale dildo
100%
First Cock Came From Old Friend
It was Saturday and I had nothing to do so I decided to go for a drive. I got into my car and headed out of the city in no particular direction. After driving for a while I realized I was close to Jim's house. We have been great friends for years but have not seen each other for a long time. I decid... Read full Story
shemale lover 2011-10-03 4,967 asshole oral sex teasing
100%
Valentine's Day Hot Encounter
On a beautiful, cold Saturday morning in Connecticut, I woke up tired and in a bad mood. I cleaned my room, fed the dog, and decided to take him for a walk to go to the store to get some smokes. As I walked, I was thinking to myself "Fuck. No Valentine's Date for me this year." I could ... Read full Story
HotVersatileTs 2011-10-04 3,939 shemale Big Cock footjob
50%
Realization vs. Reality
So…here I sit. 40 years old and revisiting the confusion of my youth. I am, and always have been, a first string heterosexual male. From my earliest memories of when I began to notice girls, I have always delighted in the wonders of women. I became sexually active at age 16, and there has nev... Read full Story
shemale lover 2011-10-18 3,748 sucking shemale cumming
69%
From Mob to Shemale
Two years ago, I was a member of the Ciccio family in Chicago. I wasn't very high up in the organization, because I wasn't Italian. I had made my way up through the ranks, however, and was making a pretty good living. I had everything I wanted, got all the girls I wanted, and did just about ... Read full Story
shemale lover 2011-10-29 10,713 orgasm facial oral sex
100%
Sexretary
Sam Nichols had a comfortable, reasonably well paid job in a computing firm called Stewart Computing. He was twenty two and had recently graduated college and had been lucky to find such a good job in the firm on the edge of San Diego, just a couple of hours drive away from where his parents still l... Read full Story
shemale lover 2011-11-12 8,393 anal shemale oral
80%
The Giver and the Gifts
From the beginning, when my breasts first began to bud--that was my true beginning --men accepted my offer of them, pleased to receive such gifts. My admirers, admiring them, circled their soft, tender areolas with the tips of their forefingers, as delicately as though they were outlining the cir... Read full Story
shemale lover 2011-11-13 4,384 anal transsexual nipples feminization
100%
The Terrace View Apartments Part 2
The Terrace View Apartment complex was an impressive site, to say the least. It filled up two entire blocks on the far-west side of town. I actually passed right by it at first; thinking that it was a fancy hotel because of the ornate architecture arrogantly rising over the privacy fences that surro... Read full Story
shemale lover 2011-11-18 3,903 anal cum crossdressing
91%
Stepdaughters Pleasure Daddy
As I was showering, I was thinking about Anna coming. What would I say to her? How would I act? I felt very uncomfortable and I was getting extremely nervous. I finished washing, then shaved. As I was getting dressed, Dawn came in. "I know your hungry, Daddy, but let's go out for breakfast.&... Read full Story
shemale lover 2011-12-05 7,875 anal licking Creampie
100%
Gratitude from client
It’s been 3 years since I got my first experience. I mean sexual intercourse with someone who determined my further life. I still remember my first time with a shemale. She was a tall slim sexy legged blonde that once came into the office of our company. I knew she was an assistant of one of o... Read full Story
shemale lover 2011-12-05 2,391 oral ass fucking
50%
Next Phase - sequel to Continuing to love the feeling
Now I would like to have both of you engage in some light bondage, how do you feel about that? Maggie quickly replied, I'm up for anything and since Sheri's my Bitch she'll do as I say. Ok then, let's get started, Linda , please come over here and let me strap you into my special sex lounge.... Read full Story
shemale lover 2011-12-08 2,983 anal oral domination
100%
Tilted Kilt Chapter 5
"What can I get you tonight?" "Mojito" I walk down the bar and bend over to pull the bottle of rum of the shelf with my back angled toward the customer at the bar. I always wear my short, plaid skirt low on my hips. I'm sure the tattoo on my lower back is in obvious display... Read full Story
shemale lover 2012-01-25 3,736 Cumshot Big Cock
100%
Jon Story
When I learned we would be in Rio for a few days, I was overjoyed. Rio de Janeiro would have just what I was looking for. While on leave in Australia, I had developed a yearning for special girls, and through careful research, Rio seemed to be someplace very special indeed. It first started... Read full Story
shemale lover 2012-01-26 5,142 Creampie tits fucking big
92%
Candy's Treats
"Hi, I'm Candy," the pretty blonde Latina said to me as I sat alone in the casino bar. She had a nice pretty face and a great body with a store bought pair of dd's. I knew the moment she sat down that she was a pro. Five straight years in Vegas at the show had taught me how to spot them in... Read full Story
shemale lover 2012-03-06 5,649 first time anal sex Latina sucking cum
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 4,686 fingering oral sex small breasts cum swallowing
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 5,354 anal sex Cumshot fingering oral sex small breasts
33%
A Night At the Party Part 1
In case you haven't read about me before my name's Marlene and I'm a 28 year old transvestite. I live in Southern California (actually San Diego). I'm 5'9" tall, weigh about 135-140 and was lucky enough to be born with a thin build, narrow hips and shoulders, long legs and a tight ass that I ke... Read full Story
shemale lover 2012-04-17 2,705 Small Tits oral sex transvestite
100%
Eve Quest Part 4
Chapter 16 Monday morning I was told to wear my red panties, bra and ribbon; my white collar, bracelets and heels and a red sleeveless dress. Sheila and Jenny ate breakfast, got dressed and loaded me in the car. They dropped me off in front of the beauty parlor and Jenny said. "If Hilda f... Read full Story
shemale lover 2012-04-21 4,280 anal sex domination oral sex transvestite
100%
The Best of Both Worlds
Michael had left to go shoot some hoops with his brother for a few hours. When he got back, he found his wife in front of the computer. He kissed her and looked at the screen to see what interesting things she had been surfing for. He was more than a little shocked when he noticed she was looking at... Read full Story
shemale lover 2012-04-25 4,357 anal sex shemale Big Cock deepthroating
88%
Didn't Know
My name is Mark Denny, turned 22 years old last friday. I work at the local supermarket as a cashier. Friday nights there is always this girl, Sandy who is my bagger. She is 5'7'' long blonde hair, beautiful blue eyes, full lips, from what I can tell a nice ass. Of course I was attracted to her, who... Read full Story
shemale lover 2012-05-09 3,983 anal sex Cumshot Blowjob
100%
A Real Fantasy
It was a boring Wednesday evening. I was away from home on business. With nobody to talk to and nothing good on the TV I decided to go for a walk. I walked for a few blocks and noticed the neighborhood was changing from hotels and bars to strip clubs and adult bookstores. I had never been to a strip... Read full Story
shemale lover 2012-05-28 5,914 anal sex Cumshot Creampie facial oral sex
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 15,006 Cumshot Masturbation Blowjob ass licking redhead
66%
Would You
'Would you...?' 'Look the part to play the part....' 1 5' 4...dreaded, and to be dreaded....bookish, be-spectacled—damn near owlish....so much so that you might miss the way her tits spoke to you no matter how much she attempted to 'silence' them ....that you might miss the way her sk... Read full Story
shemale lover 2012-09-23 6,790 sucking cum massage
100%
Working for a Living Chapter 4
The buzzing of her cellphone on vibrate was barely noticeable over the hum of the vibrator between her thighs. Normally Jamie would have just ignored it but Chris had told her he might call if his meeting finished early. Her hand felt for the phone on the nightstand beside the bed. She looked at the... Read full Story
shemale lover 2012-10-05 3,010 anal shemale oral cum swallowing
100%
Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
shemale lover 2012-10-21 8,903 anal Cumshot shemale oral
50%
Gangbang: Daddy's Girl
"Oh yeah...that's daddy's girl," my dad moaned as he massaged my enormous round sticky ass. I'm 18 and my sister was about 5 years older than me, so who knew how long this had been going on for, I thought to myself. At least I tried to think as I slowly closed my eyes and bit my bottom ... Read full Story
shemale lover 2012-12-16 9,566 sucking cum gangbang
100%
Hi, My Name Is Hollie Chapter 2
Hi, everybody! It's me again. Hollie. You remember, the 19-year-old herm-girl with a buxom older sister? It's been a while since I last wrote, but wow. Things are moving right along. And in some fun, unexpected directions! Emillie and I have been spending more quality time together, playing around a... Read full Story
shemale lover 2012-12-19 4,460 Cumshot Masturbation shemale and shemale jerking ass fingering
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,861 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
100%
Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... Read full Story
shemale lover 2013-01-04 10,438 sucking Fetish Uniform domination big boobs
80%
The Grass Ain't Always Greener...
Lawn care takes an unexpected voyeurism and exhibitionism masturbation detour I cut grass, mow lawns, manicure shrubs, trim bushes, and plant trees. Right handed and always trimming from the right side, I've never been a switch hitter when using my hedge trimmer, if you know what I mean. Always ... Read full Story
shemale lover 2013-01-16 5,216 Masturbation Blowjob blonde jerking big boobs