Shemales Porn Stories
Page 67

Becoming his girl (Sissy story by GirlyGay)

In the summer after my eighteenth birthday, I met Nick. He was a thirty-something who lived in our building. My parents had gone for their yearly European trip, and I had been left behind this year because I had college orientation during what would have been the last week of their trip.

Mooning and alone, with nothing to do for four whole weeks until my flight up west, I took to the pool to catch some sun. I had not bought new trunks in a while, and so my old ones were riding high on my legs.

Nick was already at pool, beer in hand, sitting back in a barca-lounger. His broad, smooth che... Continue»
Posted by sissyAlyna 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  
2935
  |  
100%
  |  6

The Rendezvous Pt1 (Sissy Story by CassidyCaine)

Nick looked at the email he'd received from his wife at lunch again as he got ready to leave work. It had been a month since he'd confessed to her his love of dressing up in women's clothing after he'd kept it hidden since they first met. But, Nikki was insistent so he had tried to share that part of him. She had worried he was gay or didn't want her anymore but he'd assured her that wasn't the case. Yet after all that worry, she had emailed him to tell him that tonight she wanted to play with his fantasy and role play a little to see if she could get into it. She had rented a motel room and w... Continue»
Posted by sissyAlyna 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  
648
  |  
100%
  |  1

A Night at the Metro

Before the inevitability of gentrification set in, Toronto's Metro Theatre stood for many years as the city's last full-screen porn cinema. And while more recent innovations in pornography (such as home video and later, the internet) had taken their toll, the Metro had things to offer which could not be had elsewhere. Living on the other side of town, I was an infrequent visitor to this one-time temple to sleazy entertainment, but on the occasions that I did, I'd usually have myself a good time. This story is about one such occasion.

Exiting the subway at Christie station, I could feel the ... Continue»
Posted by sissymaidjanine 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  
1183
  |  
100%
  |  3

A young man's summer [full story]

MY BEGINNING

My name is Jason, and I am a typical teenaged young man; lean, horny all the time and really happy that I have reached the age where I can get a job that pays better than mowing lawns or delivering papers. My parents work all the time and me and my older b*****r John, have had the house to ourselves since I was 8 and he was 13, which meant no more getting up at 5:30 to go to a sitter who would either keep us all day or make sure we got on the bus for school.

I discovered the concept of sex early on; John would jerk off constantly if he thought no one was watching, this sta... Continue»
Posted by serious58 2 months ago  |  Categories: First Time, Masturbation, Shemales  |  
4348
  |  
100%
  |  3

Shemale Fantasy

He met Theresa in a gay club one night. He wasn't gay but he had always wanted to fuck a shemale and so had gone looking for one. She was perfect - tall, black, muscular, huge breasts and the slight bulge of her package pushing through her shimmering gold dress suggested she had a lot to offer. Her hair was black, long and curly and she wore bright make-up on her African features.

He couldn't believe his luck when she agreed to come back to his hotel. He could tell she was excited when, from beneath her dress, her hard penis brushed past him gently as they entered the room. Theresa sat on t... Continue»
Posted by strongerbuddy 2 months ago  |  Categories: Shemales  |  
3263
  |  
100%
  |  1

MISTRESS JILLIAN MAKES ME HER DIRTY BITCH

note:IMAGINARY STORY

i was in mistress jillian's home waiting for the guests to arrive.i was told by mistress jillian that tonight she will train me to be her slave for real.
it was 9 pm.
mistress was dressed in a beautiful white dress with no panties and bra underneath.
and i was kept naked with a leash tied to my neck as if i am a dog.i was hairy with hairy chests and hairy ass and also large bush over my cock and balls

at 9 15 pm the guests arrived.i found out mistress jillian accompanied with 2 beautiful ladies coming towards me.
she introduced me to the ladies and said that i am... Continue»
Posted by mistresspet26 2 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
712
  |  
100%
  |  3

Changing desires

Sat night 06/06/15

I had tried to open myself up all Fri night with no luck. I had a good enema, it took fucking ages to get clean. I did some poppers used my smallest toy to open up for the bigger ones. To no avail. My hole would not co-operate with my & my fellas attentions. I had closed up & my fellas tonguing had little effect, which totally got me pissed off as he is so good at it. Normally this always work if i'm a little uptight (happens sometimes).I had worn my hole out I pouted & pouted. I was beginning to get very forlorn as I felt I had let my fella down. Lots of pouting & sad fa... Continue»
Posted by lolawylde 2 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
1369
  |  
100%
  |  1

The She Bitches part 1. or Trans Fu By wildrichie6

This is the first sex story I have written. I hope you all like.



Lora was 5'10 in her stockinged feet she loved stockings, & Killer heels. She had been getting hassle from a guy online for a few weeks now It had started off nicely enough, compliments a little heart gift. But there was something off. Lora had tried to let him down lightly, wanting to take time to know him she said. You know, no rush. But the guy just got abusive then threatening. Sending this message"got your ip address soon find you bitch then you'll get it" Fuck,,, this fucker was really getting to her. Ok she thought... Continue»
Posted by wildrichie68 2 months ago  |  Categories: Group Sex, Shemales, Taboo  |  
975
  |  
100%
  |  2

The Lindy Factor

When I walked in the first thing out of the ordinary was the cute little blonde sitting on the couch with all her books all spread out next to her and she was typing in her laptop. She stopped and moved an index card so that she could read it better and then noticed me.
"Hi", she said. "You must be Steve right? I'm Lindy and I'm in a couple of Julie's classes. She invited me over for dinner, I hope that's ok?"
I assured it was and I went through the small living room into the kitchen where I could hear Julie making supper. I walked quietly up behind her while she was washing something in ... Continue»
Posted by subjaye 2 months ago  |  Categories: Fetish, Shemales  |  
1764
  |  
100%
  |  2

Sweet and salty

I was very down after my divorce, I started thinking of ways to subside the heartache. Talking wasn't enough, I needed something more. While I was waiting for a friend to get off work at his bar a lady approached and asked to buy me a drink. She was about 5'9", long red hair, and smelled so sweet with a smile that eased my heart; how could I say no. We sat at the bar long after closing several drinks in and a few laughs; she ask if I wanted to back to her place. Once again, how could I say no.
I told my friend I'd talk to him later and followed her back to her place. We arrived this nice li... Continue»
Posted by jimwinslow1982 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  
4112
  |  
100%
  |  3

Love to feel hans around me.

Hi again. I'm writing new chapter of my diaries.
By that time when I finished last chapter I was more fancy about the girly stuff with my breast and my body I loved to get attention and fun and excitement.
But that they when I felt the pain of that big monsters cock with my whole body. I no longer interest to being girl. I was scared and trifide ,,,,, what will happen if next time he wants to inter intier of that in me.
My mother always had her eyes on me and I always careful. But after that day when I go home I was walking widely because of that pain.
I went to get shower when I get o... Continue»
Posted by Echoes90 2 months ago  |  Categories: Anal, Shemales, Taboo  |  
788
  |  
100%
  |  4

Predator and Prey

So, about objectification.. I had a little trip to the state line treating myself to an relatively inexpensive vacation. I wanted to get out and away to find time in femme mode, socialize, indulge and build my confidence. I made the drive down there en femme checked into my hotel, ordered myself room service and kicked my heels off while stretching out on the queen size bed.

I took in a long hot bubble bath that I had bought from a boutique in LA. I took extra time in making sure my appearance was all pull together; I ended up wanting to try some new designer leggings I'd recently picked up... Continue»
Posted by LaArana 2 months ago  |  Categories: BDSM, Fetish, Shemales  |  
711
  |  
100%
  |  3

Corrupting Little B****r

DISCLAIMER: This story is solely a work of fiction. Any similarities between people living or dead is purely coincidental. No a****ls were harmed in the writing of this story.

I was s**n going on s**n when our m****rs moved in together (they would marry the following year). I had been living as a girl for a year and a half. He, my new little step-b****r, was f**n at the time. He had just started puberty, and was a bit shy around girls, it was kind of cute. He was also kind of cute, in that young, androgynous kind of way. We got along okay, sure we squabbled, and he, for whatever reason, w... Continue»
Posted by seityn 2 months ago  |  Categories: First Time, Shemales, Taboo  |  
4541
  |  
100%
  |  4

Dinner with Brooke

Brooke texted me on my way home from work, “I’m making dinner, come down when you get home.” I replied back, “Sure, I’ll stop and get some beer.” “No bother,” she said, “I already grabbed some. Just you is all we need.” This was always nice to hear, and it was always nice to see Brooke. I felt so comfortable with her especially since the many last encounters. But I never think any more than what it is. Just dinner.
When I got home, I went upstairs, dropped my bag and headed down the front stairs to her apartment. Her door was cracked open a bit so I knocked, saying hello and opened the door.... Continue»
Posted by ahsleymills 2 months ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
5647
  |  
100%
  |  6

Home For The Holidays

The light brown hair slid down off of Sondra's back, a little more with every thrust. Her white blouse contrasted with the hair but it was so nice to see as it slid off of her back and shoulders exposing more of her white blouse. Now it just hung on the right side of her head like some kind of weird colored rope. Her blouse was slowly sliding down to her shoulders exposing her white skin. It was a very beautiful white and every once in a while a round brown mole like an island in the middle of the great pacific ocean. Her back spread out before me curved down to towards the mattress as she tri... Continue»
Posted by subjaye 2 months ago  |  Categories: Anal, Fetish, Shemales  |  
1141
  |  
100%
  |  4

Fit and Tanned - Get's Fucked by Dan! Chapte

Fit and Tanned - Get’s Fucked by Dan! Chapter 1: The Prequel


I absolutely love some of the sexy and intriguing chats I have with my fellow XHamsters while online. Most recently, a sexy girl by the name of Feliciacd and I were chatting and reminiscing about what it was like growing up and knowing that you felt different from everybody else: our first awkward steps with experimentation, crossdressing and even some of our most memorable early experiences.

I had just started to share a story with Felicia about one of my early encounters with a man - and was crafting a carefull... Continue»
Posted by LittleMissLipService 2 months ago  |  Categories: First Time, Shemales, Taboo  |  
2219
  |  
100%
  |  18

The First Time My Ass Pussy Was Fucked

There's something about having my ass pussy penetrated and pumped during sex that makes me feel more feminine sexually. Perhaps it is the fact that the entering of me, the taking of me, the domination and seeding of me, that feels so right for a gurl like me.

Not too long after I started living as a gurl openly, a neighbor of mine at the small apartment complex where we lived introduced himself to me. He spoke British English which I find so charming and a bit arousing. We got to talking and found out we both had a lot of similar interests and backgrounds. I lived alone in my apartment,... Continue»
Posted by kinkyjodigurl 2 months ago  |  Categories: Anal, First Time, Shemales  |  
9239
  |  
100%
  |  22

My Crossdressing Teen Neighbor

There is a duplex across the street, the kind with an ill arranged addition that sprouts out of the top and basically looks like shit. It's a slum lord house, geared toward your average broke ass people. You'd think I was complaining, but I am actually quite glad such a place is right in plain view.
There is a young couple that lives there, hipster punk types. The dude is nice enough but a little awkward, but the blonde chick is a little flat chested blonde hottie with piercings and pastel highlights and a plus size ass. Needless to say I'd like to breed her good. Someone looks to ha... Continue»
Posted by cumquarts 2 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
4628
  |  
100%
  |  8

My journey to sissy satisfaction

I suppose it was satisfaction that I craved, I suppose that's what we all seek from life, isn't it?

I'd realised for a long time that I was a pervert. For me it was a realisation that came to me slowly, over years. In large part this was because I had tried to deny it to myself When society teaches you that the things which really, truly arouse you the most are wrong you try hard to convince yourself that other ways to relieve yourself sexually are just as satisfying.

So, as a young boy first experiencing pornography, I sought out the sort of vanilla, mainstream pornography that I pre... Continue»
Posted by bethanyuk 2 months ago  |  Categories: Group Sex, Shemales, Taboo  |  
1932
  |  
100%
  |  17

A Freshman Surprise...

So I haven't completed this short story I started a week or two ago, but I would like some opinions none the less :) Merci <3

Luke looked forward to Friday night more than he looked forward to Christmas each and ever year, because even Santa couldn't leave hot pussy under the tree for him to unwrap. That's why he loved clubbing so much, he knew there would be plenty of girls from his college dancing sloppily in the crowd each and every weekend...ripe for the picking. The cab ride seemed longer this Friday which was probably due to the anticipation Luke was feeling- he had not been o... Continue»
Posted by MariaSkye 2 months ago  |  Categories: Anal, Hardcore, Shemales  |  
1231
  |  
100%
  |  2