Shemales Porn Stories
Page 9

A true story: me and a transvestite man - part 2

OK this is the second part of my true story.

I think I'd best point out that beyond the (I'm told) common early sexual experiences most straight men have as youngsters, with other men of their age, I'd not had any experience of men. You won't, of course, get many straight men who admit to this. But I'm not like most men.

However, this early experience was enough to leave me curious as to what it would be like to have fun with a cock. As you may have read in part one of this story, I was rapidly finding out, and loving it!

So, part one ended with me sitting on a sofa, and the lovely T... Continue»
Posted by Want_TV_CD_Cock 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
1888
  |  
88%

First shemale encounter - fantasy 2

I've always wanted to get some hard cock up my ass.

I was very horny and needed some sex right then. I looked up craiglist ads from my city, I was looking for a shemale hook up. When I the right one for me i messaged her instantly and got a reply few minutes later. She was perfect, her name was Alexa, she was short, C cups, nice smooth ass and cock to crave - 7,5" veiny with some round low hanging balls full of cum.

First shemale encounter - fantasy 2Perfectly pale, huge cock to suck on and eager to fuck my ass. After a little chat about the scenario we set the meet... Continue»
Posted by MrShy 2 months ago  |  Categories: Anal, First Time, Shemales  |  
4508
  |  
88%
  |  3

A true story: me and a transvestite man - part 1

* This is transferred across from my old profile (LookingForSomething) *

This isn't a 'story' at all, because it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more.

There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemales' 'Gay male', and 'First Time'.

OK, about 15 years ago I discovered that I got turned-on by 'shemales'. Let's be clear about that: shemale is a casual term for transsexual men, that is, they were born with a male body, male genit... Continue»
Posted by Want_TV_CD_Cock 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
3926
  |  
100%
  |  5

My friend Sally (Part 1)

I meet Sally on a sex dating site and although she knew from my advert that I cross dressed we originally meet for straight male / female sex. She was a mature lady with massive boobs who was hot for sex as hubby was unable to provide the service she now desired. We use to meet at a motel half way between where we both lived.

After a couple of meetings we got to talking about some more kinky things we would both like to do. One of these for me was meeting her with me as Jenny the sissy maid and her dominating me which she fancied giving a try as she had never done this before. So next mee... Continue»
Posted by Beau54 2 months ago  |  Categories: Fetish, Mature, Shemales  |  
3406
  |  
100%
  |  2

Daddy’s Pink Nightmare Room

My older, sometimes daddy is a big man in his late 60’s. He’s in excellent physical condition; and even has a small gym in his basement. His graying, hairy barrel chest and strong frame is still imposing for a man his age. Daddy (as I ALWAYS have to call him) is a former cop and says that’s one of the reasons his wife left him many years ago. He also got caught on more than one occasion, forcing prostitutes to service him, and pocketing d**g money which made him a dirty cop. I think over the years it pushed him to became angry and bitter, being alone and fired in disgrace; this made him not a ... Continue»
Posted by MatureBrownMan 2 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
2819
  |  
100%
  |  2

Student,

There are a few days when I came back from a business trip, I notice a guy who stops, and I wonder if I pick him up, though I do not have the habit of such moves, because of possible inconveniences. But I decide to sit in my car and connect to his destination if Is in the same direction.
I stopped the car in his vicinity and he immediately caught sight of it and unexpectedly sat inside. I started talking to the ignorant and continued to drive. He promised me to travel to another town from there, okay, but he could talk to me.
He seemed challenging to me with a nice body and faces, just to tr... Continue»
Posted by helllena 2 months ago  |  Categories: Gay Male, Shemales  |  
2979
  |  
81%
  |  2

SHARING NEW EXPERIENCES WITH SISSY CAROLE

A few months ago while chatting with Carole and talking about things we would like to do, she told me: “Would you like we do together some of the things we have talked about and we both like? Would you dare to make our fantasies a reality?” At first I thought she was like joking at me and I replied: “Of course I would like, do you think I am not able?” She then said: “Then why don’t I visit you and have a lot of fun with me”. I told him that I would think about it.

From that moment the idea of meeting Carole was in my mind all the time. I couldn’t stop thinking about it and that had me is a... Continue»
Posted by hageshiseiteki 2 months ago  |  Categories: Anal, BDSM, Shemales  |  
1813
  |  
71%
  |  2

The Meet 2

It had taken him two months of gentle persuasion to turn the shy man into this sexily dressed sissy. It started slowly, complimenting his first batch of pictures, mainly panty, cock and stocking pictures. Then the private chats exploring, teasing and planting the ideas in his mind, slowly instilling more and more control.

He knew he had him when the suggestions of outfits took hold and the pictures first appeared of this sexy black outfit. Then the requests to buy wigs and makeup worked. When the first private folder appeared and the password was passed another milestone was achieved. He r... Continue»
Posted by Kibrin99 2 months ago  |  Categories: Shemales  |  
1042
  |  
100%
  |  2

The Prom III . The Prom Event.

The Prom III . The Prom Event.




We walked into the large hall and it was filled with about 200 students. My 2 pals M. & I. called to us . “Danielle come sit with
us. " We were the last 2 of 10 at the table and I thanked my friends for saving our seats.? ” I want a dance.So do I" they said. "So do I". G. said then smiled.We sat & introduced ourselves to the others. I did not know anyone else. That reduced my anxiety. Only a select few knew my little and I do mean little secret.I quite nonch... Continue»
Posted by robin48 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
2078
  |  
100%
  |  4

The Prom III . The Prom Event.

The Prom III . The Prom Event.




We walked into the large hall and it was filled with about 200 students. My 2 pals M. & I. called to us . “Danielle come sit with
us. " We were the last 2 of 10 at the table and I thanked my friends for saving our seats.? ” I want a dance.So do I" they said. "So do I". G. said then smiled.We sat & introduced ourselves to the others. I did not know anyone else. That reduced my anxiety. Only a select few knew my little and I do mean little secret.I quite nonch... Continue»
Posted by robin48 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
1058
  |  
86%

Sissysub, just a slut

Once I am in your motel and I have shown you several different outfits you ask me to don the little girls purple dress which starts to send my clitty into a tingling fit. I am now realizing I am fulfilling a lifelong dream to have my boi pussy taken by a real man and I am in such a state that I have become almost hypnotized by your every command. You don't even tell me but I drop to me knees and crawl over to your larger than usual cock and anxiously cover it with my lipstick covered mouth. I hear you send a txt with your mobile phone but it seems unimportant to me and soon after I hear the un... Continue»
Posted by daddililzbitch 2 months ago  |  Categories: Fetish, Mature, Shemales  |  
1927
  |  
100%
  |  1

How i became an transvestite whore!

A year ago I was a straight guy with an ordinary sex life. This year I am a crossdressing hooker working the streets of West Hollywood. If there is a lesson to my story, it is to be careful what you experiment with, because you might end up being transformed into a tranvestite prostitute like me.

It all started with a brief experimentation in cross dressing. One Friday night I dressed up in slutty women’s clothing.

It took a few hours to get transformed, but I did look hot. Very hot.

I started by shaving the hair off most of my body. Shaved my legs. Shaved my chest. Shaved my underarms. ... Continue»
Posted by 34carolanne 2 months ago  |  Categories: Fetish, Shemales  |  
3058
  |  
100%
  |  5

Femdom wife wants a sissy training threesome

Married sissy sluts that completely sub to their wife are the fucking best. The dom wife can doll them up so good! One of my dirtiest threesomes was the second of the only 2 times I've had a FMCD 3 way. It was a femdom wife and her CD. I met her during a job I got called out to at her house (I work in the home service industry 24 hour on call some weeks) Sh was friendly and a little flirty while I was working on her emergency job at about 10 one night I definitely considered her cute too. She was smaller than I normally like on a woman but thick in the right spots 5'2" 180 to 200 pounds and ... Continue»
Posted by BBWandTrapObsession 2 months ago  |  Categories: Anal, First Time, Shemales  |  
2206
  |  
86%
  |  1

The Prom III. Pre prom.




http://xhamster.com/photos/gallery/8399809/151354304

The Prom III
Pre prom.
We talked on the phone a few times and had one short date on Thursday afternoon. Saturday was upon us fast. My 2 pals M. & I. called me that week and said they wanted to dance with me at the Prom. “Only if you call me Danielle?” I left them each hanging.
I tried on my prom dress 4 times on Friday and once Saturday morning. I shaved all over and no Mom did not assist me. I wore a white lacey padded bra with an A cup butt size 32. Of course I w... Continue»
Posted by robin48 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
1640
  |  
100%
  |  4

The meet

Sat at the computer waiting patiently, dressed as always in the black outfit the online friend had insisted on. Blond wig, full makeup, smooth shaven body. The amazing flesh tone fake breasts filling out the black silky bra sexily. The tight black blouse highlights the full breasts nicely. The long red nails tap the keyboard as the sissy logs in. Nails match lips, both a glossy red. The blouse is tucked into the knee length black skirt, that hides silky place panties, suspended belt and silky black stockings. The outfit is finished with four inch black patent stilettos.

The envelope symbol ... Continue»
Posted by Kibrin99 3 months ago  |  Categories: Shemales  |  
4014
  |  
81%
  |  8

My wife's a whore so am I

My wife's a whore / Me too!
****************************
Part 4
Saturday morning after our long and honest talk. I took Karen breakfast in bed. I sat watching her eat.
"So. Not changed your mind? Sure about all this?" She asked.
I nodded. "Yes. I'm sure. It's what I need. It means you get what you need. And we stay together." I smiled.
Karen smiled. "And you still want to submit to me, 100%? Have full control?"
I nodded. "Yes. Mistress." I grinned.
"Well you can start by wiping that grin off your face! And you can go and shave that beard off while I finish my breakfast!" She said firm... Continue»
Posted by need2bsub 3 months ago  |  Categories: Anal, Mature, Shemales  |  
4125
  |  
93%

Erika stretches my sphincter - Jul 2017.

It has been a few months since my last adventure and I apologize for the delay. Not much has been going on and because of that, I started to get the itch. You know - the one that says you need to get some. And online porn was simply not going to cut it. So I reached out on everybody's favorite anonymous hookup source - Craigslist - in the hopes I would get lucky. It's always a longshot, but ya never know; I have had fair success meeting fun and sexy and real people on CL. Of course, I've also dealt with a lot of shitheads and flakes and fakes as well. Call it a mixed bag. Nonetheless, ... Continue»
Posted by Quadrilateralus 3 months ago  |  Categories: Anal, Shemales  |  
3935
  |  
100%
  |  2

Let me teach you (Another fantasy)

I have been teaching at this high school for four years and the k**s really like me. I'm "the hip cool teacher", if k**s wanna skip a class they don't like or avoid a hall sweep they duck in my classroom. Well at the beginning of this school year we get a new student transfer to my class from out of district from way up north. She walks in and hands me her information and says "good morning, sir" and finds a seat. At first glance I can tell she's very shy, timid even.
I ask her to introduce herself to the class, she stands up and says "hi, I'm Rebecca and I'm from Michigan" and sits down fas... Continue»
Posted by Champdick 3 months ago  |  Categories: Anal, Hardcore, Shemales  |  
3661
  |  
100%
  |  2

Male wolf on herm bunny

You're now chatting with a random stranger. Say hi!
You both like furry.
Stranger: hi
You: hey
Stranger: 20 M wolf
You: 22/herm/bunny/bi


You: http://xhamster.com/photos/view/7181622-138999341.html#content
Stranger: Ref?

Stranger:

Male wolf on herm bunny
You: yum :3
Stranger: sexy
You: you like herms?
Stranger: I don't mind them, they look nice, but I'm a sucker fur bunnies
You: hehe ;)
Stranger: hehe
You: well this bunny wants to get on top of you and ride you hard :3
Stranger: hehe and this wolf wants to fuck your pussy raw
You... Continue»
Posted by TrapLover1234 3 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
967
  |  
100%

Awakening My Trans Nature, My Seventh Experience

I lay on the bed in underwear tasting my own cum, there was a slight hurt where my hands had been bound to the bed but nothing much. yet again there had been a quantum leap in my sexuality, the being sub to a dominant Mistress and being under someone else’s control was new but made perfect sense to me and felt perfectly right. To have to serve worked on quite a few levels. After some time I got up off the bed, put my heels back on and looked at the parcel. It was an envelope with a box in it about the size of a magazine but much thicker. If my new Mistress thought it was necessary it must be g... Continue»
Posted by SapphireSomeday 3 months ago  |  Categories: Anal, Shemales, Taboo  |  
2078
  |  
89%
  |  3