Shemales Porn Stories
Page 68

Prostate Milking, Endless Orgasms!

if she wanted breasts."

"Oh no. That's the amazing part. The more I dressed him the more feminine
he became. By now I'd moved him her and her clothes into the other
bedroom. She wasn't happy with that but we came to an agreement; I'd milk
her once a week and she would sl**p in the other room with all her
female clothes. I'd even started teaching her to flirt with a guy although
I didn't tell her what I was teaching her or why. She really was becoming a
real woman. She'd grown her hair and I taught her makeup, had her ears
pierced, got her some jewellery, even got her some bra inser... Continue»
Posted by moekoes8 5 days ago  |  Categories: Fetish, Masturbation, Shemales  |  
2331
  |  
100%

Sweet, sweet baby, part one

I got a call from Lana, one of my long term fuck buddies who was worried about her son. He’d just turned 18 and she’d caught him wearing his s****r’s clothes many times. “Can you talk to him, Jack,” she said. “I’m sure it’s just a phase, but he needs a strong man’s influence in his life.” I was on the turn around from a delivery and didn’t have a load for the drive back, so my time was my own. “Sure, babe, I’ll be passing through in a couple days, but I’m going to need to dip my wick in your wet pussy first.” She laughed and said, “I was hoping you’d say that.”

I got in after dark and Lana ... Continue»
Posted by TruckerPerv 2 days ago  |  Categories: Anal, First Time, Shemales  |  
1478
  |  
100%
  |  5

Feeling the feminity in - Ladyboy

The age when feeling feminine, being a boy wearing girls clothes and feeling guys as my love.
Cross-dressing in closet and then as a ladyboy in closet.
This was came to know by a guy near his house.(Once he will see that the CD will take some bra and try to wear) Came to know about the change in him. Regularly watching him and noticing the changes in him.
Came to know, which others could not notice that its not him its her. He is average guy who was also thinking of sex as those age guys will think. he liked and asked the change happening to crossdresser/ladyboy. She accepted the change and... Continue»
Posted by lavanyassri 2 days ago  |  Categories: Anal, First Time, Shemales  |  
572
  |  
100%

''What's a man to do''...

After a long week in work I didn't really feel like going to the party we'd been invited to.
My wife said ''We have to go and you never know who might be there''.
I agreed reluctantly and showered and changed and we headed off to the party.

Now at this stage I must tell you these are no ordinary parties we attend. We're part of a group of people that like to play. Yes it involves swapping and doing kinky things with other naked people.

We arrived a bit late and so some of the guests had already shed their some of their clothing.
A few topless women sipping wine with men with bulges ... Continue»
Posted by guru6969 2 days ago  |  Categories: Anal, Fetish, Shemales  |  
3003
  |  
100%

Helping a gurl out

Just to explain a few things, we live on an island in the irish sea between Britain and Ireland. T-gurls are rarely heard from, nevermind seen for fear of negative comments.

Vikki was a t-gurl that my wife (K)and i met via a swinging site and had played with on a number of occasions. She would visit the island with work and when done for the day would indulge in meeting anyone who wanted to fuck her.

Vikki arrived on the island on the Wed and we met her on the Saturday. As this was our 3rd meet with her we had all got quite familiar with each other and enjoyed a very sexy evening togethe... Continue»
Posted by ManxTightslovers 2 days ago  |  Categories: Anal, Gay Male, Shemales  |  
1977
  |  
100%
  |  1

My Parents Had Gone Away on Vacation

My parents had gone away on vacation for a week. I was thrilled!

On my own for a whole week, free to do whatever I liked. And truth be told, what I liked was being nude, as well as dressing in women’s clothes. The first day they were away, I began enjoying my newfound freedom.

I am very slight of build, feminine really. My body is hairless save for in my crotch.

After dinner, I decided I wanted to enjoy myself nude. I turned off all the bright lights in the house, and left on a few lights that were dim. All the blinds in the house were open. I stripped off all my clothes and walke... Continue»
Posted by ssup28 1 day ago  |  Categories: Shemales, Voyeur  |  
2939
  |  
100%
  |  1

My Fucking f****y 2

My s****r had just come out of the closet with a handful of clothes and told me to take off the swimsuit. She laid out a pair of white cotton panties with cherries on them and a matching bra. A short pleated plaid skirt and a white button down shirt. She also laid out some white thigh high stockings and some black Mary Jane platform shoes. She said this one was mine.

She laid out a nearly identical one except that her plaid skirt was green whereas mine was red. She told me to get dressed but that she would help me with the stockings. "You know I have always wanted another s****r. "Someone t... Continue»
Posted by 6270daniel 1 day ago  |  Categories: Anal, Shemales, Taboo  |  
3138
  |  
100%

Pai-chan’s long walk home

School-gurl Pai-chan took the short-cut home from school, through the Sakura sweet smelling woods one Friday after class. The trail went past an old hut and as she approached it, a masked man jumped out from behind her, grabbed her by the arms and slipping a ball-gag into her mouth, d**g the sexy gurl into the hut.

There was a dirty, stained mat in the hut and her a*****or threw Pai-chan onto it. He lit a cigarette, his eyes glinting through the mask as he watched her struggle uselessly against the bonds.

“No... Continue»
Posted by tuckpussypeachpie 1 day ago  |  Categories: Fetish, First Time, Shemales  |  
1149
  |  
100%
  |  3

Deflowered at 17...Part 1 (ENGLISH VERSION)

Many friends, some of them curious and excited by my (recently discovered) Polaroid pictures made at the seaside (with stockings) when I was 17 years old, asked me to tell the story associated to them. Someone also pointed out, "but if in one of your stories you talk about your first man -see story “my first man”- after having been “initiated” by a trans, then who was actually your first man? "
First of all, let me say that I can assure you that my stories are not fancy, they are absolutely true. I can change some details, names, situations, ... but I do not not invent anything. Anyone who... Continue»
Posted by AngelicaTrav 6 hours ago  |  Categories: Fetish, First Time, Shemales  |  
367
  |  
100%

My new flat

I had not long turned 18 when i moved into my first council rented flat, before then i had been living at home and dressing up in the confines of my bedroom chatting to guys on web cam , some of them knew i was not a girl, but most of them did not.i am only 5ft 6in tall and weigh just under 10st i guess i have never been what you would call masculine .
i had been looking forward to and planning so much for when i moved in and had been out shopping for so much girly stuff for my new life.
I had not long got out of my Bath , skin was smooth not a trace of hair to be seen, i had spent 20 mins ... Continue»
Posted by julieanneff 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
2905
  |  
100%
  |  24

black man's sissy boy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The draw... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
6939
  |  
100%
  |  11

Crossdresser has cinema fun

It had been a few weeks since I'd had any action as Clara and was absolutely gagging for some cock. The girlfriend was away for the weekend so I planned a nice Sunday afternoon in a local-ish sex cinema. I got partially dressed at home wearing black hold-up stockings, black bra with inserts as well as see-through black panties, and a matching vest-top. I pulled on a pair of jogging bottoms and a sweatshirt, pulled on a pair of trainers, packed the rest of my stuff in a tote bag, and left in the car. The journey was uneventful apart from me feeling very lightheaded from being in a constant stat... Continue»
Posted by claracduk 3 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
1712
  |  
100%
  |  24

she showed them the pictures

Some years ago, While my wife and I were separated, I was out of state and she called to ask if she could use the computer at my place. When I returned home she asked about the pictures she found of me all dressed up like a whore with some guys cock in my mouth and of me setting on a dildo and taking the whole thing. I made up some story about I was experimenting with a fantasy I had but that I didn't like the real thing and I was done with that fantasy. ( I told myself she bought it.) We never talked of it again and we got back together. Life went on. Last Halloween her friend Tina and her hu... Continue»
Posted by firstknightd 3 years ago  |  Categories: Shemales  |  
1011
  |  
99%
  |  15

A walk in the woods.....

I was lounging around the house, like a lady of leisure, wearing an elegant robe in black lace with a pair of sensual seamed stockings held up by a six-strap suspender belt and of course a pair of my favourite spiky pointed hi-heels that are so comfortable to wear round the house. I'd put on one of my favourite bras and placed a nice pair of natural looking silicone titties inside - the whole ensemble topped of with some nice jewellery. The perfect femme fatale bourgeoise SLUT that I LUV to be. I'd just renewed my lipstick and was feeling very femme, VERY slutty and as HORNY as hell when the p... Continue»
Posted by caroletv31 3 years ago  |  Categories: BDSM, Group Sex, Shemales  |  
1807
  |  
99%
  |  9

Nice surprise on the journey to work

This is a deliciously erotic story sent to me by my fellow writer Ila, I hope you enjoy it as much as I did and also the second part of the story which is to come..

I got up early this morning for a change.  I had a feeling that today was going to be a good day.  At the time I didn't realize just how good.  The sun was shining for the first time in several days.  That, at least, was a good sign and an improvement over yesterday's rain.

I headed off to the bathroom for my morning ritual.  A quick shower and then I was ready to get dressed.  I put on my normal businessman's uniform ... Continue»
Posted by keliana 4 years ago  |  Categories: Shemales  |  
1241
  |  
99%
  |  9

I am such a slut .............14.

Please take a look at my other blogs to bring you up to date. They are true, both confessional and cathartic. Thank you for your comments ~Dani

I am such a slut .............14.



I found myself very horny starving for a man. I wanted someone, needed someone, really didnt care who as long as they had a nice cock. I dressed as a slut. A real slut. Short cut off jean skirt, White blouse, white open toed heels which showed my red toe nail polish. A pair of lacy black panties over my boyclit. Red finger nails, Red lips, heavy eye liner. Sprayed some Victoria Secret perfume which i had ... Continue»
Posted by snuggle11 4 years ago  |  Categories: Fetish, Hardcore, Shemales  |  
2674
  |  
99%
  |  13

Sissy Mailee's first black cock - part1

As long as I could remember I have always had a craving for black cocks. My first time was a few years ago after partying with a friend of a friend.

I had called up one of my CD friends, Suzy, to attend a Halloween party at a local warehouse. We had agreed that we’re both going to the party as slutty school girls. We met up at her place to get dress together. When I arrived at her place she told me she can’t go because she was coming down with the flu. There was no way I was going out in public for the first time by myself. I was super disappointed but she told me that her friend Brad woul... Continue»
Posted by aznfemboi 3 years ago  |  Categories: Anal, First Time, Shemales  |  
2072
  |  
99%
  |  15

my uncle

The other day I was dressing up in my s****rs tight little black dress, I know I'm passable bit I had no idea how much... Well anyway I always heard I would look like my s****r if I had a dress on and believe me I did. So on this day I had some free time, or so I thought... I spent the day procurring my s****rs things and a few of my mom's.. see my mom doesn't have hair these days in her old age, and she is some what of a wig addict... So she has a great collection, my slightly older s****r helps her buy all of them so they are "hip styles" in moms words.. but I did my hair and makeup the sam... Continue»
Posted by 612Goo612 2 years ago  |  Categories: First Time, Shemales, Taboo  |  
3023
  |  
99%
  |  14

Party Surprise - First sex as a Crossdresser.

This is a work of Fantasy. I hope you enjoy.

Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.

I didn’t consider myself bisexual, certainly bi curious at least. I liked watching guys stroke on cam and enjoyed the odd bit of cybers... Continue»
Posted by SatincdAus 3 years ago  |  Categories: Anal, First Time, Shemales  |  
2934
  |  
99%
  |  27

Slave Life: Part 1

Prologue: My thick thighs quivered and shook as the man standing behind me, my Master, fucked my tight cunt into the bathroom wall. My loud moans filled the room as I shot a huge load all over my thighs and the floor. I had never been fucked like this before! I didn't care who heard my loud moans as they echoed across the tile filled bathroom, and I didn't care who heard the sound of my Master penetrating my ass with his enormous cock. Just then my Master moaned and shot his load deep into my tight, warm, and heavily fucked ass. When he had finished pumping his load into my ass, the warm and s... Continue»
Posted by Slave_Alice1389 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
2971
  |  
99%
  |  14