Shemales Porn Stories
Page 70

Me and My First Time

This story is not a work of fiction, this is the story of me really and my first experience of having sex with another male. I'm indulging myself really, rather than any potential readers.

I've been cross dressing for a number of years now, on and off. In those periods of indulgment I've used butt plugs and dildos to heighten my pleasure and I've also dreamed of having sex with a man I've always considered myself to be straight, I don't go through life looking at men and fancying them, but when I go into my feminine state I dream of having a cock to play with (rather than just my own). I... Continue»
Posted by uktransvestite 9 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  7

Pleasuring Me - A Nylon Poem

Up in the morning and ready to dress,
Must have slept roughly my hair is a mess.

My nightie hangs loosely from shoulder to waist,
But juts out below, well I am in no haste.

A rub on the nylon, my prick feels so great,
Suddenly remembered I must not be late.

Out from the drawer comes a suspender belt,
Followed closely by stockings, which I should have felt.

There in the toe of the black nylon mesh,
Is some of my sperm, 'fraid it ain't fresh.

No matter to me, to the drawer I go back,
And a new pair of stockings with seams, yes they're black.

Out of the packet and up... Continue»
Posted by SheerLonny 9 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
  |  1


Hi so the first time i went to a bathhouse was when i was 18 , i was dating a 44yr old dominate top tranny (Tina) who had the biggest uncut latino thick cock, her cock was the one that made me not only give up on girls but she turned my body and mind into a complete bottom sissy , my butt became her pussy and my hole was being waxed ,dressed stretched , eaten , fingered and breed!!! i was so scared when she came inn me and pnp made me forget about the fear and just enjoy!!!! we loved to smoke T and poppers during sex ... anyways we were bored and high and she had me completely dressed up in he... Continue»
Posted by daddyssissyLA 9 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
  |  4

My First Time - part 2

Seems right that I talk about the second time Steve and I had sex. Don't worry I'm not going to talk about them all, just some of the kinkiest times we had. The second meet was notable not only for the sex but also I was sort of willingly pushed into a higher level of crossdressing. For a long time I had been wearing panties, tights, stocking etc under my male clothes, when I got the chance. I had worn dresses etc when home alone, but this was different.

I got a text message from Steve on the Sunday evening after our Saturday night, saying he had enjoyed himself and did I want to do it ... Continue»
Posted by uktransvestite 9 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  4

Jayne's Story Part 2

My story now continues in 1978, I was no longer seeing my earlier lovers, & had moved to London,& to become friends with Dave,a guy I meet in a disco one friday. I would normally get the last train back to my West London bedsit,but Dave insisted I stayed at his apartment south of the river,so we went there.Being very d***k,neither of us was shy talking about our private lives,& I told him I liked wearing womens clothes,& was in fact wearing a bra & panties as we spoke. Dave said he didn't belive me,so I removed my jumper & shirt exposing the black 36a bra underneath & dropped my jeans to pro... Continue»
Posted by tvluver2008 9 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
  |  2

Santa Baby

Santa Baby

Nikkie Silk

It was the last Friday night before Christmas, and the pub was packed
with office workers intent on celebrating the Christmas spirit by
getting as d***k as they could manage. Slade were belting out ‘Merry
Xmas Everybody’ over the speakers and the whole pub was raucously
joining in with the chorus. People were kissing under pieces of plastic
mistletoe and more than one office romance would begin, and probably
end, that evening.

The group that had grabbed a table to the side of the bar were typical
of the customers in the pub. Working at one of the companie... Continue»
Posted by nikkiesilk 9 months ago  |  Categories: Shemales  |  
  |  13


Since I moved from Knoxville back towards the airport in Alcoa, I have had some fun times with a big dick black daddy, a hot, young hung white country boy and an older white daddy dom with a big, fat beautiful cock. However, I hadn't had much contact with the neighbors other than hanging out with some of the girls and getting snickers from the men. That all changed this past summer (2015)

Across the hall, two young college age guys moved in and they immediately noticed the effeminate sissy boy next door. I tried to avoid them as much as possible though I did sort of like the humiliation wh... Continue»
Posted by CuteGuy2Use 8 months ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  3

Part 3

I suppose I had better get the one where I had my fantasy, out of the way. It's not that interesting, unless you are me!

When dressing I always fantasised about two things, either having sex with a guy whilst wearing lingerie and stockings or being pounded by a big black guy with a 12 inch cock. I got one but not the other!

In one my chats with Steve he asked me about my cross dressing and why I did it etc. I told him that above all, I just love cross dressing. He had tried it in the past but it hadn't done anything for him. We got into a discussion about female clothes and what I ... Continue»
Posted by uktransvestite 8 months ago  |  Categories: Anal, First Time, Shemales  |  

Ballsy Secretary

Shemale - cum-eating – dominant – submissive – big cock – secretary – boss

A few more good strokes and I'd be like a fire hydrant. My breathing was ragged; my fist pumped up and down the long neck of my cock nearly as fast as my heart beat in my chest. I love this part. That moment where your knees go weak and you finally give in. Your eyes clench shut and the pressure from your balls explodes up your shaft until your tip blasts that first strand of cum and sweet relief finally takes you over.

I was there right now. My big girl had never looked harder; the massive pole looked lik... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
  |  1


It Started With Tattooed Eyeliner

"We settled on black, right?"

"I'll leave it up to you," I said. Lynn began organizing her bottles and
tubes, preparing the ink for the tattoo machine she used for applying
permanent makeup. In this case, she would applying permanent eyeliner to
my upper and lower eyelids.

"Good. Black is basic. Now, we never really settled on what style. There
are a lot of things you can do with eyeliner, and you've specifically
asked that I not take into account your being a male. Is that still what
you want? This is the last chance to change your mind."

"Y... Continue»
Posted by klammer 8 months ago  |  Categories: Fetish, Shemales  |  
  |  1

Yesterday we went shopping...

Yesterday we went shopping.

Master Silk had decided that my undies were dowdy, and my heels not high enough, so we went shopping. Naturally, we shopped in a town not too local to us - we didn't want our cover completely blown! (OK, it was Bath! Lovely tea shops in Bath!)

I wasn't wearing my sissy outfit - I'd not convince anyone! But I was wearing tight jeans to show off my bum, and a girly blouse. A dog collar around my neck was disguised by a pink silk scarf. Our first shop was good old Marks and Spencers, a stalwart of the British high street. M&S may have an old fashioned imag... Continue»
Posted by sissy_jenny 8 months ago  |  Categories: Anal, BDSM, Shemales  |  
  |  1

Gracie and her best friends son...

Gracie was attending a birthday party at her friend Rachel's house, who's son was turning 18...

"I've known Rachel for more ten years now and she is one of the few type of friends who actually stick around. It felt as if not too long ago I was turning 18, but I was now in my early thirties and Rachel probably felt old too now that she was was nearing forty!... But anyways let's continue with the story...

There was plenty of alcohol available, for those in the appropriate age range of course, and Rachel loved her drinks whenever the occasion called for it. I was the only other f... Continue»
Posted by adblman 8 months ago  |  Categories: First Time, Shemales, Taboo  |  
  |  2

Wet dream PART 2

Driving to my place it was a conflict, I was totally wet and my companion I bet she was too.

Olga was my co-pilot and could not help to notice that she was day dreaming, I looked at her and under her glasses I saw in her dark sparkling eyes that she wanted something. Her imagination was running wild.

We came to a traffic sign and she in a sudden move got into my crotch, unzipped my pants and let herself into my manhood, moved again my thong and .... I had to go, the light was green, this little brat got me again!!!! We took the highway and she was kissing and pumping me at 90kh.
... Continue»
Posted by ilialenyc 8 months ago  |  Categories: Fetish, First Time, Shemales  |  

My Ex-Girlfriend's Mom #3

The three of us were laying in Lana's bed, recuperating from an awesome sexual experience. Or at least awesome for me. I could only imagine what kind of sexual experience these two beautiful, busty, extremely hung ladies have had. Lana, the "mother", very sexy for an older woman, with a ten inch cock. And Jill, the "daughter", a knockout in her prime, with a twelve inch cock!

We talked about what we had just done. They told me I was a natural at sucking cock and couldn't believe I had never done it before. But it was true. I told them I had only had sex with real girls before tonight. But f... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  8

Crossdresser Dominated For The First Time

Chapter 1: A Couple of Painters

One very long boring day in the middle of summer, i was home all alone, my parents were at work and my siblings out somewhere. I decided it would be a good day to dress up and have fun while i was home alone. I went to my secret stash of clothes i keep in my closet and picked out my purple lingerie. It consisted of a purple and black lace bra with matching thong and garter belt with black stockings. I put it on then went to get my cute blonde shoulder length wig, it fitted nicely as i applied my make up.

Once i looked like a sexy girly slut i... Continue»
Posted by Badassgirl123 8 months ago  |  Categories: First Time, Group Sex, Shemales  |  
  |  12

Panty Fantasies - Coleen's Magic

Feminization - body change – gender swap - sissy - panties – satin – lingerie – cocksucking

He swallowed hard, his body tense with anticipation and admittedly a small amount of fear. He didn't _really_ know this woman and her beauty was no guarantee of her honesty. He was exposing himself as he had never done before, all in a desperate attempt to capture his dreams, to experience the most intense pleasures.

Looking around the bathroom he saw that it was finely appointed with grey and pink marble and fine Italian tile. The towels were Egyptian and felt wonderful. The whole penth... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: First Time, Fetish, Shemales  |  
  |  6

Public Panty Change

Bisexual male - mmm threesome – crossdress - panties – bra

It had been a couple of months since I'd met and dressed up for my sugar daddy. He'd had a lot of money and was willing to buy me any outfit I wanted, along with panties and makeup for the complete girly look. In exchange, of course, I dressed up and provided him with an afternoon of hot sex that had left my little girly hole stretched and aching. So, when he contacted me once more and suggested another day of shopping, I jumped at the opportunity. I made the usual preparations: shaved my girly hole smooth and rinsed myself o... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  4


An old story of mine but you might enjoy it


I couldn't believe my eyes when I saw the message and telephone number
written on the inside front cover of the book. I smiled as I recalled
the number of times I had idly opened these books in anonymous hotel
rooms on my business trips. It had started three years earlier when I
had joined the sales division for the company I worked for. I was
twenty-three and had never worked in sales before, but I was keen to
succeed in my new role.

I was going to have to adjust to quite a few new lifestyle changes, not
the least of which wou... Continue»
Posted by nikkiesilk 8 months ago  |  Categories: First Time, Shemales  |  

A night with Louise....a very special "girl&q

Before telling about an evening of 'earthly delights' with a crew member on my boat, I want to say this story is dedicated to a new online friend, Zoe.

As I have mentioned in some of my stories, I owned and operated a 100' charter yacht in Alaska for over 20 years. My target audience could be any race, age, size, or sexual orientation. What they all had in common was they had to have the financial assets to pay top price for a 10-15 day trip with only 12-15 passengers.

One year I needed a crew member immediately and one was hired in Seattle one morning, and that afternoon he was landin... Continue»
Posted by 1kaaboom2 8 months ago  |  Categories: Hardcore, Shemales, Voyeur  |  
  |  5

Experiences Of A Crossdresser

This is an introduction to my crossdressing experiences – touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever.

I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like slips and sheer blouses. I would typically be drawn to anything black, but did have a fondness for nude tights and white slips, also.

I usually liked the 'mysterious and seductive' look. I wore mostly black – tight dresses or skirts, of... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: Anal, Fetish, Shemales  |