Shemales Porn Stories
Page 58

Adult Video Store #1

A few years ago, a longtime friend of mine, Brian, asked me to help him move to a city about three hours away from our hometown. I told him that I was not happy that he was moving but that I would be happy to help him if I could.

We got everything loaded, which wasn't much, in both of our vehicles and headed out on a Friday afternoon. His new apartment was in a city I had never been to before, so I got to see many new things on this trip.

Before we left, he told me that it should take three hours and fifteen minutes to get there, if we didn't have to stop for anything. It was a long driv... Continue»
Posted by naughty_bi_interest 1 year ago  |  Categories: First Time, Shemales  |  
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My Ex-Girlfriend's Mom

My name is Bobby. Before I tell this story, let me set it up by telling a short story first.

At the end of my senior year in high school and into the beginning of the summer, I dated a girl for a few weeks but never got past making out with her. Her name was Jill. One weekend Jill and her mom, Lana needed to leave town and asked if I would check in on things at their house. I did as they asked and once, while I was there, I got on the computer and watched some porn, shemale porn.

A few days after they got back, Jill and I got into an arguement and I broke it off with her. She tried calli... Continue»
Posted by naughty_bi_interest 1 year ago  |  Categories: First Time, Shemales  |  
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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 1 year ago  |  Categories: Fetish, Hardcore, Shemales  |  
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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 1 year 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 1 year 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 1 year ago  |  Categories: First Time, Shemales  |  
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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 1 year ago  |  Categories: First Time, Mature, Shemales  |  
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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 1 year ago  |  Categories: First Time, Mature, Shemales  |  
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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 1 year 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 1 year ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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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 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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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 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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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 1 year 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 1 year 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 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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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 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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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 1 year ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
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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 1 year ago  |  Categories: First Time, Shemales, Voyeur  |  
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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 1 year ago  |  Categories: First Time, Shemales  |  
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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 1 year ago  |  Categories: First Time, Shemales  |  
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