Sort by
Relevancy

Free Stories

100%
Roberta, Molly and Ed
Friday "Commander Cromartie?" Lt. Commander Edward Cromartie, USN, turned toward the voice that had spoken his name. He saw two female naval officers, a tall willowy light-skin Black woman, and a short Asian one. The Black one was wearing the uniform of a full commander, the Asian of... Read full Story
shemale lover 2012-09-04 5,247 Cumshot threesome Blowjob Big Cock condom sex
90%
DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
CD DIXIE IN NH 2016-05-10 10,105 Big Cock cumming sperm ebony cock
50%
LE PROGRAMME D'ÉCHANGE SISSY ⚧️ ⚧️
Kristy a travaillé pour Le Matriarcat. Cela semblait plus officiel que ça ne l'était vraiment. Comme si c'était un "Nouvel Ordre Mondial". C'était en fait un club dirigé par des femmes spécialisées dans certains services que les hommes paient grassement. Cela pourrait être appelé prostitution selon ... Read full Story
Femboy 2021 2023-03-25 1,072 Teen (18+) Cumshot Big Cock gangbang Interracial Sex Toys gloryhole cum in mouth femination forcé poule mouillé Maitress bdsm poule mouillé
100%
The Experience of a Lifetime
My divorce was hitting me really hard. My wife outgrew our relationship and started living her own life and I had a front row seat to everything. My heart and life was upside down. I didn’t go out anymore. Friends and family both told me it was time to get my life back on track and start living ... Read full Story
therefill05 2020-11-30 19,873 Big Tits Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob blonde Big Cock Ebony Uniform domination cum in mouth
91%
HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
CDDIXIE4U 2019-01-08 33,069 Teen (18+) Crossdresser Cumshot Masturbation Bareback Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Lingerie domination Homemade Compilation cum in mouth shemale + shemale
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 2,594 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
66%
Cock Sucking Jail Whore
I've always known that I was not meant to be a guy. Being sexual curious I would look at porn mags like any one does. At first it was just magazines with pictures of naked woment. It was when I ran across my first Hustler magazine that my life was changed forever. Seeing pictures of studly guys with... Read full Story
shemale lover 2011-09-17 4,356 Cumshot asshole oral sex
100%
First fuck in public ;)
You’re only wearing a coat, I find a place where, I can kiss you then slide my hand between the flaps of your coat. I expose your breasts and slide my hand down across your tummy down to your pussy. My fingers start to explore your soft bush, working there way to your soft pink lips surrounding your... Read full Story
BalkanLoco91Ri 2019-08-26 3,740 Stockings Teen (18+) Amateur Big Tits Cumshot Outdoor Masturbation Bareback Creampie Blowjob Big Cock Uniform domination Homemade pov cum in mouth
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 5,981 Cumshot Bareback Creampie Shemale Fucks Guy threesome Blowjob Big Cock Ebony domination Sex Toys cum in mouth
100%
The Big Tiddy Goth Girl
Hannah and I went to the pool in my apartment complex. This was my first time dressed as female in public and I was loving my new, feminine tan lines. To keep a long story short, while tanning we were perv'd on and approached by a guy calling himself Mark. He was desperate for our attention and fumb... Read full Story
KaceyKlarissa 2024-02-23 4,502 Crossdresser Big Tits Cumshot Masturbation threesome Big Cock Shemale and Girl small cock big ass sissy femboy cum on tits goth
100%
David to Dee
"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... Read full Story
shemale lover 2012-07-29 12,405 Cumshot Masturbation oral sex
82%
Bikini Boy
I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage... Read full Story
shemale lover 2012-06-12 15,280 Cumshot Fetish oral sex crossdressing
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 8,380 Big Tits Cumshot Masturbation Uniform Frottage
100%
FILLE DE RÊVE ⚧️ ⚧️
« Alors, à quoi ressemblerait ta petite amie parfaite ? » « Toi », pensa Steph, regardant dans les yeux noisette avec des reflets dorés à l'intérieur. Il lui fallut quelques secondes pour se rendre compte qu'il devait répondre avec sa bouche. « Oh, euh… quelqu'un d'attentionné je suppose ? ... Read full Story
Femboy 2021 2023-02-17 901 Stockings Crossdresser Cumshot Fetish Blowjob Big Cock gangbang Lingerie domination Guy Fucks Shemale Interracial Sex Toys cum in mouth
85%
My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
the greatest liar 2019-06-14 11,719 Small Tits anal sex Latina Masturbation Bareback Creampie Blowjob Big Cock transformation gangbang Shemale and Girl Guy Fucks Shemale Sex Toys Ass to Mouth cosplay hormones high school real life situations
100%
Regina’s Double threat.
Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... Read full Story
Regina10 2022-02-08 2,964 Big Tits Cumshot Bareback Creampie Fetish Blowjob blonde Big Cock redhead Guy Fucks Shemale Ass to Mouth double anal
81%
Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
shemale lover 2015-02-27 6,914 Cumshot suck Shemale Fucks Guy Ladyboy ass fucking swallowing
85%
BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
bkkldby 2019-06-17 13,985 first time Teen (18+) Amateur Group Sex Big Tits Cumshot Outdoor Bareback Blowjob Big Cock Asian lesbian public place
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 7,291 Cumshot oral sex Latex sissy
50%
"SISSIFIED": 12 JOURS DE SISSY-MAS
JOUR 1: mardi 25 C'était le matin de Noël quand j'ai entendu frapper à ma porte, ce qui était, bien sûr, très étrange à dix heures du matin. À midi, j'allais chez ma famille pour Noël, et j'avais rarement des visiteurs inattendus. Toujours dans ma robe, je me dirigeai vers la porte et fus s... Read full Story
Femboy 2021 2023-01-20 1,234 Stockings Crossdresser Amateur Fetish Blowjob Big Cock Lingerie domination Sex Toys cum in mouth
100%
Angel Chapter 6
This is an entry in the Literotica Winter Holiday Contest, and is part of an ongoing series on the life of Angel Jones, a beautiful young T-girl in London. For more detailed information on her and on the other characters who appear in this story, please see previous episodes. Angel Jones was uns... Read full Story
shemale lover 2012-12-01 4,160 Cumshot oral tgirl
50%
Transsexual Sisters Chapter 5
Part 5: A friend is forced to say goodbye Cassie had made things right with Michelle and Nicole. She now had to square things with Randy. She found him in the hospital lounge. "Hi Randy, can we talk?" "About what? I think you made things pretty clear the other night." ... Read full Story
shemale lover 2012-09-08 2,744 Cumshot Masturbation threesome ass fuck
66%
Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... Read full Story
shemale lover 2012-09-26 12,727 Group Sex Cumshot shemale oral
50%
LA MÈRE DE BULLY M'A TROMPÉ ⚧️
C'est ma première année à la fac, et c'est déjà devenu l'enfer à cause du harcèlement. Mon tyran Jordan se moque toujours de mon corps. J'avais atteint la puberté tard au lycée, et quand elle est arrivée, je n'ai pas vécu le changement impossible que les autres ont fait. Au lieu de cela, j'ai des ép... Read full Story
Femboy 2021 2023-02-16 741 Crossdresser Cumshot Fetish Blowjob Big Cock Shemale and Girl domination Sex Toys cum in mouth
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,540 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
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 5,317 big dick tranny anal sex Cumshot orgy facial 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 4,651 Cumshot oral sex sissy
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 3,990 Cumshot Creampie Blowjob Big Cock tits licking
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 23,851 Cumshot Blowjob fuck fingering big boobs
100%
Transsexual Sisters Chapter 6
Part 6: A Party to Remember MICHELLE AND NICOLE MAKE A CAREER CHOICE After their tormentors were jailed, Michelle and Nicole felt relieved and happy for the first time in weeks. Whether from curiosity, respect or sympathy for their ordeal they became very popular around the USC campus. They we... Read full Story
shemale lover 2012-09-08 4,068 Cumshot sucking threesome Shemale and Girl deep throat
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 4,100 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
85%
The Gang
I had always thought of myself as female in spite of the fact that I was born with male genitlia. Even in my earliest memories where I had witness sex, I identified with the female in the relationship. As a small young child, I had always longed for womanhood each time I heard a woman sing or especi... Read full Story
Regina10 2020-06-29 8,745 Group Sex Cumshot Blowjob Big Cock Ebony gangbang double anal
71%
Angel Takes on Two Men
On the Friday after her experiences with Augustus and Peter, Angel attended the meeting of the Gay, Lesbian, Bisexual and Transgendered Association, and found Gus and Kenny both in attendance. After the meeting, which was rather ordinary, they joined her, either of them giving the other rather stran... Read full Story
shemale lover 2012-12-07 4,140 tranny Cumshot oral sex squirting
71%
Down the Path Part 2
I waited to hear from him again. At first, I didn't know if I really wanted to get together again. The first time we met, at times it was a little more intense than I was looking for. After a few days I couldn't get him out of my mind. I couldn't believe how badly I wanted him to call me. Finally... Read full Story
shemale lover 2012-09-16 4,958 hardcore Cumshot oral sex
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 22,654 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
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 8,411 Group Sex Cumshot oral sex assfucking
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 8,236 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
66%
The Coma Girl Brain Transplant
[This frivolous story is something I put together as an entry for a comedy competition earlier this year, not to be taken at all seriously, a bit more sci-fi than erotica, more of a mind-fuck than anything else so it’s not jerk-off material but hopefully some of you might still enjoy it] Thankful... Read full Story
cara_elaine 2017-12-19 6,420 Crossdresser Uniform domination
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 5,418 Cumshot oral sex deepthroating crossdressing
100%
Seven Lessons Part 1
Bryan was king of the road warriors. Speeding around the country in his sleek, powerful Mercedes selling whatever his latest job demanded. He was damn good at it too, always raked in huge amounts of commission until some faggotty client bitched about a one-sided deal he had put together and then it ... Read full Story
shemale lover 2011-11-30 2,936 Cumshot shemale oral
50%
The Visit
A visit to a hooker, where I describe my bisexual experiences *** It was a weekday, I had bummed off work and had made my way to Ipswich for a visit to Rona, my favorite hooker. She was a lovely woman in her forties, with a fantastic figure, not slim but not fat and with huge tits. She... Read full Story
shemale lover 2012-01-26 8,159 Group Sex licking sucking pissing fucking
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 5,116 Cumshot condom 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 4,496 Cumshot shemale cum swallowing mouth fucking rimjob
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 6,482 Cumshot Fetish oral sex cum swallowing
75%
Flowers in the Heart
Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... Read full Story
shemale lover 2012-11-11 10,347 anal tranny Cumshot oral
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 4,924 Cumshot Blowjob massage
100%
Don/Dawn of the Dead
I did all of the 'normal' things first. Checked all the doors, checked all the stores, closets, back hallways, stockrooms and bathrooms for zombies. Made sure everything was sealed off. Established a base inside the mall to operate from. Made an escape plan. Hid some of my guns and ammo in a cache w... Read full Story
shemale lover 2012-10-25 3,499 first time oral jizz
100%
Woman Cross Dresses for Power & Sex
Tucked in the far corner of a dark, dancehall parking lot, Sarah, also known as Robert, was having sex in a car with Joseph, also known as Josephine. Having sex in a car was no big deal. A lot of couples have sex in cars. Yet, if a passerby could see through the steamy windows, a sight to behold, ev... Read full Story
shemale lover 2012-10-09 3,887 sucking Fetish fingering crossdressing
85%
Whores and Pimps - Part I
Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... Read full Story
shemale lover 2012-05-13 7,904 Stockings Crossdresser Cumshot Fetish oral sex pantyhose
87%
Feminized By My Mother Chapter 2
My mom was staying in as were Jen's parents so we parked on a dark road and made out while I fingered her. Her panties were absolutely drenched when I was finished, and she rubbed her hand inside them and used her pussy juice to jerk me off, I spurted all over my pants and she laughed. "I ho... Read full Story
shemale lover 2012-07-24 13,040 sucking Fetish fucking sissy
100%
Couple and a Tranny
There is a saying that a single man looking for companionship and good fortune will seek someone for marriage. Lydia and I met several months ago on an online dating site. We agreed to meet at a bar restaurant for drinks and initial meeting. She was at the bar wearing a yellow sundress, white painte... Read full Story
Jon Paul 2022-09-20 5,188 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
90%
On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... Read full Story
shemale lover 2012-09-01 11,178 Crossdresser Cumshot Blowjob jerking pantyhose
100%
Vegas Honeymoon to Remember
I had dated my wife (Carmen) for about 6 months before we decided to Marry. One evening we were soaking in the Jacuzzi together and drinking wine. She always wants to try different things, which makes our sex life wonderful. Carmen asked me if I ever had any fantasies. I said I guess like most me... Read full Story
Jon Paul 2018-05-30 20,287 Group Sex Cumshot Bareback threesome Ladyboy Shemale and Girl
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 5,105 Group Sex Cumshot sucking doggy style
100%
A Shell of A Man
Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty w... Read full Story
shemale lover 2012-06-11 9,325 Cumshot Fetish sissy
65%
Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
shemale lover 2012-12-19 10,486 Masturbation Blowjob blonde ass fucking big boobs