Sort by
Relevancy

Free Stories

100%
Meeting Amanda
I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... Read full Story
rforasht 2022-07-20 8,086 Big Tits Cumshot Shemale Fucks Guy threesome blonde Big Cock Lingerie Shemale and Girl redhead Homemade Shemale fucks couple
100%
My 1st Time was Not the Only Time.
One late night after hitting the slopes and partying I left my friends birthday party feeling extra horny. It was about 6 or 7 in the morning now and after having no luck finding an escort I responded to an ad on craigslist posted by a trans woman. I figured two things, this dick isn't going to suck... Read full Story
LesFuax 2019-02-16 9,641 first time Small Tits Amateur Latina Bareback Creampie threesome Blowjob Big Cock ass fucking barebacking barebackedshemales first time with a tranny raw anal raw dick raw fucking firsttime
78%
Anal Therapy
My new psychiatrist wasn't at all what I expected. When I saw her name in the phone book, I pictured a dowdy old lady wearing a long, gray skirt and flat-soled shoes. What else could Dr. Edith Doss look like? I got my answer when a tall, leggy redhead stepped into the waiting room. A tight, black... Read full Story
shemale lover 2012-11-24 8,118 anal Fetish cum crossdressing
57%
Nicks Shemale Experience
Nick had discovered he had a thing for shemales 4 months ago after stumbling across some pictures on the Internet of a really hot ladyboy from a porn link site. This sort of thing had never turned nick on before but looking at pictures of the small-breasted brunette really made his dick hard. It did... Read full Story
shemale lover 2011-08-22 4,264 anal Fetish oral
100%
Mi primera experiencia anal
Les voy a contar una historia muy excitante de mi vida Soy un chico muy curioso desde temprana edad, desde que tenía 9 años jugaba con mis primos a las escondidas por las noches o a las carreras y bueno ya saben cómo todo niño siempre busca conocer y saber cosas y sentir cosas, pues un día Estaba j... Read full Story
Bigdick1689 2024-10-03 830 anal Amateur Cumshot Big Cock Homemade pov
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 14,638 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
100%
Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
Beryl 2023-12-12 8,103 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
100%
Beefy Buns
It's hard to get good help. Probably, that's true in any business, but it's especially difficult to find decent employees in the fast food racket. Believe me; I've tried. I manage the local Beefy Buns franchise--burgers, fries, and shakes is our mainstay, but the menu also features fish and chick... Read full Story
shemale lover 2012-04-22 6,582 anal sex Creampie blonde shemale
100%
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 15,242 Cumshot Masturbation Blowjob ass licking redhead
100%
From accidental trans porn addiction to a cum filled booty
One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... Read full Story
CDJaneBooty 2022-04-01 10,930 first time Crossdresser Amateur Cumshot Bareback Creampie Blowjob Big Cock gay Homemade Ass to Mouth curious first time with a man
28%
Current Fantasy
I really wanna get fucked for the first time and my dream way of doing it, always wanted to do a porn. The dream is that I go there and get done up in such a way, I am unrecognizable, just looking the best. Have a tranny come in and do my make up, the way she likes it and gives me a preview of what ... Read full Story
martley 2023-06-30 6,085 anal Amateur Group Sex Cumshot Fetish Big Cock Lingerie big ass Homemade femboy shemale fucks shemale cum in mouth
100%
My Noisy Upstairs Neighbors
So... I just moved into my new apartment a few weeks ago, and ever since then all day every day I have been hearing loud noises from my upstairs neighbors. Not just normal walking-around noise, but loud and heavy bangs, crashes, and poundings against the floor, my ceiling. Not only was the sound ann... Read full Story
Chrissy Tunnell 2024-07-15 4,542 Crossdresser Bareback Fetish Blowjob Ladyboy gangbang domination Guy Fucks Shemale sissy double anal
100%
Buffy the Shemale Vampire Slayer Part 15
The Slayer looked at the witch's ass. It was beautiful, she thought. Round and smooth and creamy white, each buttock seemed a half moon. Willow's impaled anus showed within the deep cleavage between the silken globes, its rim riding the stiff cylinder of Buffy's cock as she plunged it into the witch... Read full Story
shemale lover 2011-08-23 4,795 anal asshole shemale
85%
My weekend with Nicole
So I believe I last left off about how me and Nicole started dating and let me say it was some of the best sex I've ever had but there is one particular time I could share. So after about 2 months of dating I was basically staying almost exclusively at her place. So the first weekend I s... Read full Story
Duke04 2017-05-20 11,257 Bareback Creampie Shemale Fucks Guy Blowjob Big Cock redhead Ass to Mouth cum in mouth
100%
the orgiastic fever of a trans-milf
Simulating a woman, or the orgiastic fever of a trans-milf It's been two months since I moved to the megapolis, where I've discovered several places where the third gender goes. One of my first explorations was a huge lingerie shop in a MALL; I wanted to buy some sexy stuff without being noticed ... Read full Story
hippocampus_171 2024-09-04 2,805 anal Amateur Cumshot Creampie Shemale Fucks Guy Latex Sex Toys Mature small cock
80%
Buffy the Shemale Vampire Slayer Part 14
"Let's get this over with," Buffy suggested. "The sooner we start, the sooner I kick your demon ass." Baphomet smiled. "You will fuck the witch," he said, "while I fuck you." Buffy shook her head. "Willow's my best friend. I can't-" "Th... Read full Story
shemale lover 2011-08-23 5,522 anal sex asshole Big Cock
100%
Best trip to the mountains
I was driving out to the hills for some solo camping. I was alone since all of my friends had quit on me at the last minute, but i figured i'd just enjoy nature while i had the chance. I was almost through with the four hour drive, and noticed fewer and fewer cars as i got closer to the site. Onc... Read full Story
shemale lover 2012-03-04 4,211 anal shemales Group Sex oral
100%
Awakened by Candy
It was a Saturday and I was just strolling down the High Street, going nowhere in particular, when I noticed a commotion down a side alley. A largish male was pushing two girls around; they both looked pretty distressed. I grabbed the bloke as he slammed one of the girls into a door, and he went ars... Read full Story
shemale lover 2012-05-19 3,642 anal sex Cumshot Masturbation fingering ass licking
83%
The Making of A Sissy Part 12
Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as... Read full Story
shemale lover 2012-05-31 4,778 anal Fetish little cock sissy
50%
For The Sensual
For the sensual, description is everything. The collar. The collar is custom-made; one of two; her request. This particular one matches the corset. The corset—the "bustier." The collar. Literally, no choker here. She is disciplined. Her collars merely evoke ownership. She belongs. Sh... Read full Story
shemale lover 2012-11-14 3,582 anal kissing facefucking
100%
Sissy Slut and Stepdads part 2
My mother kicked Frankie out and swore that he was the last loser she would ever date. She believed that we were still having sex, and she was right. Pure raw animal lust drove us, and It was even better when we sneaked and got. That nervous adrenaline mixed with my passion and made me super horny a... Read full Story
Regina10 2021-02-15 4,603 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
100%
Camming Down the Rabbit Hole Ch. 10
As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous nig... Read full Story
Dani_does_Dallas 2022-04-12 3,984 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
100%
How A straight tatted white guy turned me out to a femboy
So I met this straight white guy on an app (wont say) hes tatted a bit thuggish and likes black femboys I noticed. At that time in my life I really didnt embrace being femme I was kinda in the middle doing the cute gay twink boy thing. He didnt mind me presenting male he did like black guys or femme... Read full Story
Ezra_Kyle25 2024-07-18 5,253 Crossdresser Amateur Ebony domination Guy Fucks Shemale Interracial big ass Homemade sissy femboy interracial fuck
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 10,907 anal tranny Cumshot oral
100%
The Making of A Sissy Part 11
Whilst Bella showered, Ellen and Sandy went down to the poolside to ready some ice and bottles for drinks later; there was Bella’s phone, Ellen tapped in the number to her own phone, and also took down someone else’s number. Ellen smiled wickedly. “I have a very sweet idea, but ... Read full Story
shemale lover 2012-05-31 3,140 anal Masturbation Fetish
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 6,356 anal Cumshot Latina Bareback Creampie threesome Shemale and Girl Lola
100%
an old friend
I hadn't heard from one of my oldest friends Dave for many years, we used to play in a band together, hang out and occasionally watch porn together after a night out drinking, with Dave usually falling asleep with a lit cigarette in his mouth, he is about 5'7'' medium bordering on at... Read full Story
NWLexxxi 2024-12-26 1,068 anal Crossdresser Bareback threesome breeding mmf
100%
Lola Chapter 4
We sat at the table. I had made the effort to cook a small three-course French-inspired dinner. I was in love, but Lola’s mind seemed elsewhere. - How nice… She was chewing absent-mindedly. - I have to ask you something. - Shoot baby. Ask away! Lola looked deep into my eyes: - Could you ima... Read full Story
BellaBeau 2023-10-30 6,142 anal Cumshot Latina Bareback Creampie Shemale Fucks Guy Frottage Homemade Lola
73%
Vegas Baby: Swinging for the Fences
"Hello," Miss K said as she answered the phone. "Where are ya? You're gonna be here in 5? Alright. You got the address for IHOP, right? OK, See ya in a bit. Bye." "So is this girlfriend of yours on her way?" Jennifer chimed in. "I mean if she doesn't exist, this... Read full Story
shemale lover 2011-11-15 5,825 anal oral handjob
100%
April Fools!!
I'm Jimmy James and I've been hanging out with the same six guys since we started college. We're a pretty close knit bunch and have stayed in touch since then. At 25, I'm the only one of the seven of us still not married. Even though we all still get together for parties and get togethers, for t... Read full Story
shemale lover 2012-01-04 11,848 anal oral cd
88%
Oh My, You Have a Cock...
It was a regular Friday night no different from others I'd experienced before. I was lonely having broken up with my girlfriend earlier that week. What a bitch! I needed to find me a sweet woman capable of matching my libido. My last lady was all about the lights off, missionary position sex, come t... Read full Story
shemale lover 2013-08-09 33,353 anal sex Cumshot Shemale Fucks Guy redhead
100%
Jo, Shemale Goddess! Part 1
Jo plumped the cushion and carefully positioned it until it was precisely at the right angle. Nothing less than perfection would do. Ricki, her friend of twelve years was coming to stay overnight and she would notice if the tiniest thing was out of place. An impatient knock on the door signalled ... Read full Story
shemale lover 2011-09-04 5,921 anal sex sucking shemale
100%
Angel & Victoria
Angel was a beautiful young girl living with two of her best friends, Monica and Amanda. All were transsexual, and the three shared everything together, from clothes, their sexy intimates, lovers, and each other's bodies. Angel was the youngest, at 23, a Japanese anime lover and the most... Read full Story
shemale lover 2011-09-23 6,594 anal Creampie Big Cock oral
100%
Job Opportunity
So. A bit about me. I'm 5'4", 139 lbs, long brown hair and deep brown eyes. 5.5 cock, cute 'bubblebutt'. I had been looking for a job for a long while with no luck, and REALLY needed the money bad. I finally got a call from the female owner of a coffee shop I had applied to. I had actually fill... Read full Story
shemale lover 2011-10-22 5,760 anal shemales hardcore
100%
Catching Up
It was with mixed emotions that I listened to the message on my voice mail. It was the familiar sound of Mark, a long time friend whose call I had missed earlier that afternoon. Now as I heard it, for the third time, I felt my stomach slowly relax from the uneasy twist that had taken hold the minute... Read full Story
shemale lover 2012-06-04 3,993 anal sex Creampie fingering
80%
Office Policy
“Ok ladies and gentleman, please put your hands together for the beautiful and talented Erika!” the DJ’s voice rang out over the thumping alternative beat as the object of my lust strutted to the stage. Erika’s saucy red curls bounced on her head and on her soft porcelain whi... Read full Story
shemale lover 2012-08-30 9,138 anal ass sucking threesome tits fingering sex blondie
87%
Fem Firm 3: The Return Of Frankie
PART 1 THE VISITOR Over the next couple of months, it was pretty much business as usual at the Firm. You know, depositions, court filings, motions, hot sloppy blow jobs and ass destroying anal sex (Thanks Angela!).Not to mention Friday Fuckfests. But since I started working here everyone se... Read full Story
bennyx709 2016-11-14 12,734 anal sex ass fucking oral sex cock sucking thick cock
92%
T-Girl Meets T-Girl
It was a silent car ride home. He looked at her, she looked out the window. She looked at him, his eyes were on the road. Neither of them broke the silence. It stayed that way until he parked in her mom's driveway. The soft-spoken young man told his girlfriend, "Goodnight Ashley. I'll call y... Read full Story
shemale lover 2012-08-29 6,610 anal sex Cumshot shemale and shemale domination blondie
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 8,612 anal shemale oral
83%
Teacher Student Confidentiality
It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... Read full Story
shemale lover 2012-02-11 14,655 anal Blowjob black fiction
100%
Force Feminized up Asshole
"Yea I thought the singing was OK but I don't really go for that style too much" "And the girls?" Brian prompted me. "Oh come on Brian leave him alone we all know he's not really interested in girls." "Give him a chance, people can change! Perhaps Carl's d... Read full Story
shemale lover 2012-02-13 7,065 anal Group Sex Fetish cum feminisation
80%
Honolulu surprise
Back in Honolulu, I used to fuck plenty of women as I was young, tan, blond, and in super shape with Triathlons. Mostly I would try to close the deal really quickly after I met someone, just going with “Hey you wanna go fuck?” question after a few minutes of chit chat. You would really b... Read full Story
shemale lover 2012-02-16 4,418 anal Creampie fuck
0%
Deep sexual fantasy part 2
I Know it been since last year since wrote about my bring up, and in that time space I have done a lot more. So remember i was saying that in part 2 I would talk about my fantasy....well to my luck it came through :). On a cold winter Sunday, coming from a business meeting i made my way onto t... Read full Story
shemale lover 2012-02-21 3,245 anal sex Shemale Fucks Guy virginity
100%
Buying Time
It’s a hundred dollars to use the sex machine in the public restroom. Insert a couple of fifty-dollar coins into the payment slot to remain anonymous, though of course it’s more convenient to just let the data terminal do a neural scan and auto-debit your account. A hundred bucks buys... Read full Story
shemale lover 2012-03-25 4,224 anal sex Cumshot shemale
100%
Betrayed Chapter 1
She's having an affair. I couldn't ignore it any longer; the evidence was right there on my monitor that Wednesday afternoon. I had felt so... tawdry – a word I had thought I would never use – hiring the detective to follow her, follow up on my suspicions. It was as though I was betrayin... Read full Story
shemale lover 2012-05-28 7,054 anal sex Cumshot shemale oral sex cum swallowing
100%
Big Surpise In Small Package
It was a Friday night and I was extremely horny and just my luck my girlfriend was out of town, but I wasn't horny for her I was craving cock. I knew I was bi for a long time and loved to have a nice hard cock to play with every once in awhile. So I decide to call my girlfriend to tell her I was goi... Read full Story
shemale lover 2012-06-11 4,629 anal Group Sex Cumshot Blowjob
100%
My Dominate Spanish Mistress Parts two and three
I wasn't going to write anymore for this story but i posted the first part of the story on 99chan's elit board which a recommend going to. Maybe with the help of some of you people writing or encouraging more writers on their stories the board might return to its former glory. After all some guy sa... Read full Story
bruceclark 2012-08-24 5,075 anal Latina domination slut feet
92%
A Shemale and Her Unexpected Friend and Me
There I was on the boardwalk waiting for texts back from trannies from craigslist. As I sat staring at the ocean, I yearned for some sexy shemales to get back to me. I started walking around the boardwalk more, anxiously, desperately. All the sudden, a beautiful older woman was walking by with her d... Read full Story
tysonsbakery 2015-11-16 7,214 tranny ass shemale domination double anal
72%
Sissy's Cherry Got Popped!
S)heplacement- Definition- Any sissy male that is willing to take the place, or replace any woman who is not properly taking care of their man inside or outside the bedroom... These gu(y)rls will make sure their makeup and lipstick is just right, their lingerie is matching, and that they are always ... Read full Story
Kevyn-JeanneHarris 2015-12-20 9,984 anal sex submissive sissy cross dresser
90%
Ginger loses her virginity
My friend's father, Mr Webster, had turned out to be anything but the pillar of the community he pretended to be. Despite his regular Sunday church attendance with Mrs Webster, it transpired he also enjoyed the company of other men. He was certainly enjoying me, and within a few weeks I had fal... Read full Story
Ginger__57 2018-03-26 7,306 Stockings Crossdresser Amateur Bareback redhead
92%
My wife Gwen
My wife, what can I say she is tall and leggy with thick, natural wavy orange-red hair with beautiful porceline skin and just enough freckles to tell you she is a true ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen. From the time we... Read full Story
Zöe from Kingston 2019-01-08 8,138 Shemale Fucks Guy redhead Guy Fucks Shemale cum in mouth
100%
Weekend Fantasy
have so many fantasies....the one that gets me lately, is having access to a house out in the middle of nowhere, for a week or weekend, where i can dress up, all day. No one knows of my lustful secret....so the idea of being able to stay this way without thought, gets me so hard and such in the moo... Read full Story
martley 2020-07-20 5,690 solo Amateur Group Sex Masturbation Big Cock Lingerie domination Sex Toys Homemade self sucking cum in mouth double anal shemale + shemale
66%
intimate Cousins
My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... Read full Story
Regina10 2022-05-13 6,548 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
Surprise Ending (Part Three)
I rolled my dick around her hole to spread the precum off it and lubricate it. The feeling was sensational and I couldn't spend much time easing my way in --I shoved right in the the hilt in one steady push. Karla practically jumped off the couch and screamed. I thought maybe I had hurt her (I am... Read full Story
Chantel13 2022-08-23 4,775 Crossdresser Amateur Group Sex Cumshot Outdoor Creampie Shemale Fucks Guy Big Cock Shemale and Girl redhead Guy Fucks Shemale Ass to Mouth
50%
The Greatest Lie Part 15
I think that if you could get honest answers, a lot of heterosexual guys would probably admit to having had at least a passing desire to be a girl. If they were honest, they would probably admit they thought of it "when I first noticed a girl's breasts" or "when I first felt a girl or... Read full Story
shemale lover 2012-01-20 6,727 anal hardcore erotic encounters fantastic
50%
I've just been fucked
I have just been sodomized, motherfucker deep within me. I received in my heart a prick long and wide. He enjoyed me, his cum dripping from my anus distended, opened, which bears the mark of the powerful flared tail that just screwed me divinely. I am happy, exhausted, panting, lying face down on th... Read full Story
Lailatvx 2012-03-20 3,613 anal sex Cumshot travesty