Shemales Porn Stories
Page 9

Sara becomes The Bride


crossdresser – transsexual – sissy – bride – slut – wedding night – lingerie – oral – stockings – anal

Becoming Sara has been the most amazing experience I have ever had in my life. Between the clothes and living as her all the time, to becoming the thing men fantasize, it has been an amazing transition.

While I had some good friends, girls like myself that I met at one of the trans bars in town, I did lack male friends. I was never a sociable person, very much an introvert but since I have dressed, that has allowed me to get out of my shell.

T was a guy that hung out at one ... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: Anal, Fetish, Shemales  |  
826
  |  
100%
  |  2

My First Time as Sara... Pt. 05

crossdresser – sissy – lingerie – anal – trap – oral – transexual – stockings – coquette – sissy boi

I've become Sara now for just about a year. One year of exploring deeply who I was, my past, my history and who I've become at this moment.

I was no longer just John, the meek man who was dumped by his fiancé for not being man enough. That skin was shed. Instead I became Sara. I became empowered and in charge of my life. It was as if panties and heels, cute girl next door dresses and sultry and sexy lingerie gave me a sense of empowerment.

I also had Steve with me the entire way. He be... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: Anal, Fetish, Shemales  |  
506
  |  
100%
  |  2

Julia Teil 01

Teil 01: In die Falle gegangen

Alles begann damals als spätpubertierender 18 Jähriger.

Die Mädels in meinem Alter interessierten sich nicht für gleichaltrige sondern für die 20-22 Jährigen und die jüngeren hatten mit Jungs noch nichts am Hut.

Da wir aber als einer der wenigen Haushalte schon DSL hatten beflügelte das Internet meine Phantasien immer mehr und der innere Druck Sex mit einem Mädchen zu haben stieg. Eines Tages erzählte mir dann mein bester Freund er hätte eine Kontaktseite im Internet gefunden und sich am Wochenende mit ner geilen 38 Jährigen getroffen.

Wie er mir so d... Continue»
Posted by ringmyding 2 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
627
  |  
100%

Kitten Club

My name is Frank and my girlfriend is Joanne. I'd never even heard of
the place, but it was her birthday, so her choice. When I found out
what went on there, I wouldn't have gone anywhere near it for a very
good reason I'll tell you about in a minute.

You wouldn't have even known the club was there. It was down this dark
alley, lit by a weak streetlight, and just a green door with "The
Kitten Club" above in a faulty old neon light. A couple of bouncers
looked twice at us but let us in.

Once we were through that door, we were into a different world
altogether. It was like nowhere ... Continue»
Posted by lana100 2 months ago  |  Categories: Shemales  |  
3288
  |  
100%
  |  4

My First Time as Sara... Pt. 04


crossdressing – oral – crossdresser – heels – lingerie – fantasy – stockings – trap – anal – sissy

I love being Sara and everything it has awakened in me. In the months since I have been with Steve and becoming Sara, I have slowly shredded away my old self like a snake looses its skin. The only time I even dress up as John is when I'm at work. Even then, I have a little bit of Sara with me by either wearing panties and sometimes pantyhose under my khaki pants.

In the months as Sara, I've amassed a collection of clothes and slowly my closet was less John and more Sara. Skirts, bl... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: Anal, Fetish, Shemales  |  
597
  |  
89%
  |  6

A Latina babe with a surprise

A Latina babe with a surprise

That Winter we had escaped from the New York`s cold weather and had gone for a week to Miami.
My sweet Ana was so horny during these days… On the fourth night, after dinner outside in a nice restaurant, she suggested to go down to the hotel bar and pick up somebody to enjoy a good time for the rest of the night…

We decided finally to go out from our hotel and we ended in a nice pub just a few blocks away from there.
A nice brunette girl, Latino type, started a conversation with Ana.
My wife tried to speak in Spanish with her, but the girl said she only ... Continue»
Posted by Anitaslut44 2 months ago  |  Categories: Anal, Mature, Shemales  |  
1075
  |  
100%
  |  2

GloryHole experience

I entered through the rear door to the bookstore. It was nearest to the video booths. I knew it pretty well. I stopped by every time I was in this part of Texas. I was already wearing my bodyshaper and stockings under my street clothes. I had came in and purchased twenty dollars of tokens a few minutes earlier. I was clutching my oversize purse that contained my heels, dress, red wig, makeup condoms lube etc. This ABS had a restroom in the booth area. I loved that. I went directly to the restroom. It had 2 stalls and a urinal. No one was in there which surprised me as the lot seemed to be quit... Continue»
Posted by proudman2 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  
1680
  |  
100%
  |  3

Train Journey -Part I

Hi All,

A bit about myself, i am a bisexual male living in north india and i like to crossdress when am alone or traveling alone. I have to travel a lot for work to various places all over the country and i CD whenever i travel alone and have had a lot of fun with guys and girls.

Well as it happens i had to go for some work for a few days in orissa and my office booked me on the rajdhani 1st class. The train was at around 4 30pm. As i always do on long work trips before going to the train station i went to my regular lingerie shop( the owner knows am a CD, buts another story) and bought... Continue»
Posted by hornyboyind 2 months ago  |  Categories: Anal, Gay Male, Shemales  |  
492
  |  
100%

Gangbang at Ricks part 5

Gangbang at Ricks part5

All of us left when we got up, I counted Heads (cock heads lol) still 8 nice size, and Kim n Me us Sissy's woke up first, i told her meet me in the shower, we can have fun cleaning each other for the rest of the day. trying not to wake them all up, but i had a big problem Nicks big soft cock head was still in me all night, it's going to get messy, his and Don's loads in my belly, Kim grab that big butt plug try to pull nick out of me, she knew pulled it did a good job pluging back up. she giggled ... Continue»
Posted by mrheat22 2 months ago  |  Categories: Anal, Gay Male, Shemales  |  
440
  |  
100%

Jacki's Journey into Sissyhood Pt. 02

sissy – pussy – oral – strap on – anal – plug - cum – mistress

I awoke as sunlight began to creep into my bedroom. I might have thought last night was a dream if it wasn't for the large hairy arm d****d across my shoulders and the large cock poking at my backside. I tried to slowly slide out from under Steve's arm, only to have him pull me closer and kiss my shoulder. "Good morning Jacki," Steve said sl**pily as he yawned.

I took my free hand and grasped his erection, and laughed," It seems this guy has been up for a while now."

He chuckled back, "Yeah, well who can blame him h... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: Anal, Fetish, Shemales  |  
587
  |  
100%
  |  1

My First Time as Sara... Pt. 03

crossdresser – oral – sissy – lingerie – stockings – tranny – crossdressing – anal

I've been with Steve for a couple of months and to say I've been happier than at any time in my life would be a gross understatement. Being with Steve has been an awakening. I'm no longer afraid of life. I was shy and timid as John. I didn't make decisions. I didn't take the lead in anything and was easily bullied. My ex fiancé was the worse bully.

As Sara I came to understand a few things. I am starting to understand the power that woman have. I'm beginning to grasp the sway a woman can have when ... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: Anal, Fetish, Shemales  |  
613
  |  
92%
  |  3

The Making of a Sissy (Part 6: Broken)

The sound of rain beads beating against my window like a drum filled my bedroom as I got up out of the bed to make my way into the bathroom. It was the beginning of another hot, wet, and steamy summer day. This summer had felt like it was continuing on forever and also forever changing my life, but we had reached July and I didn't have much more time before I would be starting college. I began to draw myself a warm bath then slid my shorts and panties off around my hips and down to my feet. My freshly painted toenails shined through the lacy bikini as I kicked them into my hamper. As I pu... Continue»
Posted by briantid8 2 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
511
  |  
100%
  |  3

1st time-VERY young black TS hooker

A few years ago I was driving to work just before 8:00 A.M. I was stopped at a light while crossing a small bridge and saw a beautiful young black woman (so I thought) in a sundress. I had my windows down and happened to make eye contact with her. She came right out and asked me for a ride about a mile in the opposite direction I was going. Even though I am about as gay as a man can get, as she was so young and innocent looking I said ok. She got in my car and I headed where she directed me. The ride took about 10 minutes as we hit several red lights. She was kind of elusive to my casual quest... Continue»
Posted by reesielover 2 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  
1577
  |  
100%
  |  1

Baltimore glory hole HUUUUUGE black cock

I was in Baltimore on a business trip and, as always when I travel, I extend my trip through the weekend to go to gay bars and more importantly the porn shops with glory holes. I go there for one thing--to suck as many cocks as possible. My preference is almost ANY black man or white fems and TS's.

I took a cab after a gay bellboy at the hotel told me where to go for that reason. The cab dropped me off on a two block strip loaded with the bright lights of all-night porno shops. I talked to a few black teens that were hanging around and asked where I would find the most black men to go... Continue»
Posted by reesielover 2 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
2266
  |  
100%
  |  4

Jacki's Journey into Sissyhood

crossdress – sissy – anal - plug – oral

I thought to myself could I really go through with it this time? I had to at least try it, didn't I? I took another swig of wine and then brushed the blonde strands of hair out of my face again as and I read through the message one more time. "Jacki, Id love to get together and treat you like the beautiful gurl that you are. Look over my pics and if you like what you see, send me your number and we can set up something, Steve." I sat there in a matching red lace bra and panties and black patent high heels, with my makeup, and my favorite blonde... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: Anal, Fetish, Shemales  |  
1893
  |  
96%
  |  6

Tits Have Benefits Ch. 04

bisexual – lesbian – anal - strapon – cock sucking - feminization – transformation

Thank you for everybody's support for this story. Andrea gets an invite to visit Trish and Sandy in California and the story takes an unexpected turn, although I am guessing that some of you may have figured out what direction things might go. Please note that in the first few paragraphs there is a lot of plot development with no erotic scenes but fear not when the erotic scenes do cum, nothing is held back...

*

After transforming myself into a shemale and returning to claim the love of my life J... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: Anal, Fetish, Shemales  |  
511
  |  
100%
  |  2

My First Time as Sara... Pt. 02

sissy boi – crossdresser – tranny – lingerie – virgin

I look up at Steve and give him a genuine smile. A smile that tells him I want and crave him. In a whirlwind day that started with me buying some girly stuff to enjoy on my day off from work, is now ending with another mans cock in my lipstick covered mouth.

I have his legs open and I'm on my knees. My hands are now running over his muscular and tight legs and my tongue licks his stomach. I have a naked man, average in every single way, except for his very thick, 8 inch cock sitting on my couch and I'm in my black stockings wit... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
1266
  |  
100%
  |  3

My first cd sexual experience w my virgin roommate

My dorm room was wrecked trashed with take out containers and empty beer cans. I would ask my roommate Matt to help clean the place but he was always face deep in his hdtv playing video games. Maybe if he got laid atleast once in his life he would put the controller down. He never tried talking to any girls because he was always afraid they would turn him down because of his weight. And as much as I really needed the place cleaned I wasn't going to clean a dish but had a better idea. A few weeks ago I went into my room after class and created a cliche sexy girl name online account in hopes to ... Continue»
Posted by triplexvenom 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
6352
  |  
97%
  |  8

The civillian

I shadow wrote this story for a friend. The two of us hope you enjoy it.

When I finished high school I spent a few months working, before being drafted. Aside from a short period of training, during the first half of my term I spent most of my time behind a desk. I did spend a day a week doing guard or drill duty, to keep in shape and keep my field skills fresh. When things escalated and another unit was in need of a new sergeant, I was promoted and got reassigned. Still behind a desk, but now assigned to a war zone, I did spend a lot more time in the field. I had to go often to an improvi... Continue»
Posted by GalFa 2 months ago  |  Categories: Anal, First Time, Shemales  |  
1349
  |  
100%
  |  4

My First Time as Sara... Pt. 01

crossdresser – sissy – virgin – sissy boi – anal – lingerie

I only knew Steve as my landlord. To be exact, Steve was the only son of the two people that owned the small apartment complex I am currently living in as of right now.

My reason for moving here was out of necessity than anything else. Three months prior to moving in the 20 unit complex I lived on the other side of town with my then fiancé Sara. We're both late 20 something k**s that moved in together after collage and while the first couple of years seemed grand, it was bad things that were under brewing in the relation... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: Anal, First Time, Shemales  |  
2283
  |  
100%
  |  9