Shemales Porn Stories
Page 17

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 5 months ago  |  Categories: Anal, First Time, Shemales  |  


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 5 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Wet dream...

I woke up this morning with my panties wet, I am a male that dress as a woman and loves panties. My wife knows my tendencies and love them.

It has been a long time since I have had a wet dream, for some weird reason it happened and this is what I remember.

I was in my male mode. I was in a house full of people. Little by little I started to recognize faces and places. It was my friend Olga's house. It was a big house in the suburbs, two levels and great rooms. I found myself in the middle of the table with my friend having dinner. Everyone had an idea that she and I were going out,... Continue»
Posted by ilialenyc 5 months ago  |  Categories: First Time, Shemales  |  
  |  2

Cutting Ms Betty's Lawn ~ Chapter 2

Chapter 2

I nodded, of course I did. I wanted my pants off and I wanted to be touched and sucked. I loved sex and would if asked, say I was addicted to it. Betty undid the button on my shorts and they fell to my ankles as I stepped out of them. "Oh have such a lovely cock smooth and you shave it? she asked. "Well.....a little.....I hardly have any.....but the few I have look I take them off." Betty cupped her palm over my cock. It felt warm and I shivered thinking how much she seemed to like it. "Oooooooooh.......did you just tremble?........ Continue»
Posted by goodsonformom 5 months ago  |  Categories: First Time, Mature, Shemales  |  
  |  15

Cutting Ms Betty's Lawn

My mother had suggested I might consider cutting Ms Betty's lawn as none of the other boys in the neighborhood would. All the other mothers hated Ms Betty and wouldn't allow their sons to associate with her. She was one of my mom's friends and I thought nothing of it, so I agreed to do it every week. It seemed Saturday mornings would be best, so I put her in my schedule and planned on the following Saturday to the first.

I was doing a great job with my lawn cutting service, picking up new clients from word of mouth after I did a lawn or two, but my schedule was becoming full. I needed to sa... Continue»
Posted by goodsonformom 5 months ago  |  Categories: First Time, Mature, Shemales  |  
  |  7

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 5 months ago  |  Categories: Shemales  |  
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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 5 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
  |  2

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 5 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  4

gay sex with 60 years old man in chennai

Hi I'm ashwin, about me IM FAIR AND SLIM HAIRLESS BODY MY AGE IS 23. I LOVE GAY SEX CD SEX AND STRAIGHT SEX. TOTALLY IM A PURE BISEXUAL GUY THATS WHY I ALWAYS WEAR RING IN THUMB FINGER. BOYS OR GIRLS IF YOU WANT A HOMO SEX PARTNER THEN WEAR A RING IN THUMB FINGER AND MIDDLE FINGER, LEFT HAND OR RIGHT HAND IT DOESNT is my another true story which happened 2days back. As I told you in my last story I'm a call taxi driver in chennai. Before 2 days at morning I got a trip so I reached there to pickup my customer. I called him and said I reached so u can come sir, he said OK I'll co... Continue»
Posted by Ashwinchennai1 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  2


The secret sissy in question claimed to be a young, successful man,
heading his own department at work and living the good life. But he
yearned for his teen years, where he would passably dress up and meet men
off the internet. He wanted to be completely broken and feminized to the
point of no return.

Here is what I had to say, and after writing the little scenario at the
end I thought it might be a good enough start for my first posting to
this site.

Without further ado:

Hey there- this is a long message but consider it your first test.

I see you've posted your request under... Continue»
Posted by klammer 6 months ago  |  Categories: First Time, Shemales  |  

Yoü can´t decide

"He's here, Sissy- answer the door," she calls confidently from the
dining room where I just poured her a glass of wine.

I steel myself for the humiliating ritual that's been perfected through
rote repetition- though the number of times it's performed, like every
other degradation I suffer through on a daily basis, does little to
lessen the sheer gut punch of the act of pure submission.

I open the front door and step back to allow Sir through, my gaze
downcast as not to make the punishable offense of eye contact. In my
mind, the ridiculousness of this situation is heightened as he'... Continue»
Posted by klammer 6 months ago  |  Categories: BDSM, Shemales  |  


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 6 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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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 6 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
  |  1

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 6 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  7

Made me a woman pt.3: Swallowing my pride

I'm standing still frozen. After getting fucked, bred, degraded and then receiving slutty clothes, heels and jewelry by this big black man. He brought on three of his friends,equally as black and as big with muscles sitting on the couch eye fucking the shit outta me. I just walked outta the shower mmy long blod hair is did, my face looks extra whore-y. dark eye makeup, red lips and all. wearing a gstring and bra matching set. purple with black strings. a mini pink fishnet dress. a pair of 6 inch clear heels and an ankle bracelet with an engram an ace of spades. the clothes, heels, and jewelry ... Continue»
Posted by alexismorel 6 months ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
  |  1

Trans girls first public sex with a stranger

I just had an amazing, and accidental public sex experience.

I was traveling home from an out of state Thanksgiving weekend with friends, and I had to go to the bathroom. So I pulled off the highway.

I always hate public bathrooms because they are usually dirty. So I found a pull-off on the side of the road next to a swimming area. It was just about to get dark so I decided to get out of the car quick and scurry into the woods. There were two other cars parked there with people just loitering, but I made little notice.

There were a few footpaths through the woods that led down to the... Continue»
Posted by SissyAtHeart 6 months ago  |  Categories: First Time, Shemales, Voyeur  |  
  |  13

My all time favorite story part3

All credit to Julian0682

Ch. 03: Deep-Throat

As Tonya got up to answer the door, Bailey uncuffed Julian, and he got up and stretched, and sat on the edge of the bed. He was still savoring the taste of cum from these two lovely trannies, when the door opened. A tall blonde beauty walked in, and leaned down to give Tonya a kiss.

"Jenny, meet our cumslut," Tonya said, his softening cock dangling as he walked over to Julian and placed a hand on the back of his head, as if to show off a trophy.

"Hello cumslut, I am Jenny. Tonya tells me that you love to suck cock," Jenny said as he wal... Continue»
Posted by samcolt1911 6 months ago  |  Categories: First Time, Shemales  |  
  |  1

First time with "Ashli" part 1

My first time with a Trans

It all started back at a Halloween party. I went as myself I wasnt big on dressing. Up and I only knew a few people at the party. I noticed this absolutely stunning redhead looking at me from across the room I looked up and gave a smile I then grabbed my drink and went over to talk to her.

Her name was Ashli and she came to the party with only a few people as well we hit it off and I could not get over how sexy she was in her tight little dress she was maybe 110lbs and just over 5 feet tall with amazing tits. We decided to take shots together and then hit... Continue»
Posted by joker621 6 months ago  |  Categories: First Time, Shemales  |  
  |  1

A moment in Taos

I recall another meet I had with another dresser who happened to live in Taos NM. Again I met her on-line and after exchanging a few e-mails we planned to meet. At that point in time I was like an hour and a half away from there. She offered to meet at her place and she told me to text her when I got closer. But I had somewhat of a dilemma. Since the drive was going to take a while, I was debating whether I should dress first or find a place closer to change. I’ve only been to Taos like one other time so I wouldn’t know of a place to change in a hurry and wasn’t going to stop at some gas stati... Continue»
Posted by stormietv 6 months ago  |  Categories: Fetish, First Time, Shemales  |  
  |  1

The Transformation --- Prologue

I come from a very poor f****y of eight. My father is a mine worker who became very ill only a few months before the beginning of this story and got into early pension for a very small income. My mother is from very orthodox origins without any school and she can barely read and write so she was a housewife for her whole life. As the oldest male c***d from 5 s****rs and 3 b*****rs I had to quit school and find work to earn something so our f****y was kept fed. Our only property was our house in a very bad state so we had nothing to sell to get some money. If we sold the house we would have now... Continue»
Posted by harloch 6 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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