Shemales Porn Stories
Page 7

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 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
494
  |  
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 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
441
  |  
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 1 month 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 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
614
  |  
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 1 month ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
508
  |  
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 1 month 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 1 month 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 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
1895
  |  
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 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
509
  |  
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 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
1265
  |  
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 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
6351
  |  
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 1 month ago  |  Categories: Anal, First Time, Shemales  |  
1351
  |  
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 1 month ago  |  Categories: Anal, First Time, Shemales  |  
2270
  |  
100%
  |  8

Tits Have Benefits Ch. 03

Shemale - crossdressing – feminization - transfirmation - anal – strapon – oral

Thank you for everybody's support for this story. In this chapter the complex dynamics of a polyamorous relationship including 4 women and a shemale is explored. Andrea becomes gradually and lovingly integrated into this 'f****y' while having the time of her life ...........

After transforming myself into a shemale and returning to claim the love of my life Jane, I was accepted into Jane's loving f****y of lesbian lovers, this despite the initial protestations of Jenny a tall blond bombshell. In fact J... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
503
  |  
100%
  |  2

Brad's Bitch

bisexual – gay – reluctant – domination – feminization

The phone rang. I pulled it from my jeans pocket and saw that it was Brad. Shit! I really didn't want a call from him right now. Maybe I should just ignore it. But somehow he always knew when I'd just ignored his calls. And then that was even worse.

I answered it, thinking only fleetingly about "the speech" that I'd composed and honed over the years and knew now that I would never actually give. I don't know why I even thought of it anymore. Maybe it made me feel just a little bit in charge of my life to at least imagine that ... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
2692
  |  
96%
  |  4

Playing with myself dressed.

I lived by myself for a while so no problem there, so after showering and shaving my balls and butthole, I set up my dvd player, (yeah it was a while ago), to play Ladyboys in Latex. I retreated to my bedroom to choose an outfit.
Hmmm, I feel naughty and nice tonight, so white, definitely white. I chose a white silky bustier with spaghetti straps and garters, and some brand new thigh high sheer white stockings. After I attached the garters, I pulled the laces on the back as hard as I could and tied them tight. I tucked the laces up so they wouldn't get messed up in my ass.
I looked in the m... Continue»
Posted by badboy4320 1 month ago  |  Categories: Anal, Masturbation, Shemales  |  
562
  |  
100%
  |  1

Cockatoo part 10

Cockatoo Part 10

Nikkie Silk

My heart skipped a beat as I heard Shane’s voice from behind me and felt his hand on my shoulder. It couldn't be, I thought, I must be so tired I was hallucinating. Alex said, ‘Hi Shane, glad you could join us.’ Nin looked as if she had seen a ghost, Areeya was smiling in welcome and I felt like I would pass out. The hand moved off my shoulder and Shane’s massive frame came into sight.
‘Hi Nin, Hi Areeya.’ he said, then paused and looked at me, ‘Hi Jamie, how are you? You look gorgeous babe.’
I looked at Shane and then Alex and back at Shane. It was clear ... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: Gay Male, Shemales  |  
267
  |  
100%

Tits Have Benefits Ch. 02

crossdressing – shemale – strapon – anal – feminization – oral – transgender

Well thanks for the positive feedback from my first story guys. I am touched that you picked up on the fact that this is actually a sensitive love story. In this next part Andrea finds that in choosing to be in a relationship with Jane she also is choosing to be in a relationship with Jane's lesbian friends.........


In summary may name used to be Andy, now it is Andrea. And after completely transforming myself into a woman, tits and all and with the only exception being my dick, I had returned to claim ... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
772
  |  
77%
  |  2

Never Going Back Again

feminize – feminization – transsexual – crossdresser – gay

To tell the truth, I never really figured out how to do the guy thing very well. I was always small for my age. People used to say that I'd shoot up someday, but it never happened. All through my school years, I looked about two years younger than my classmates. It didn't make for an adolescence filled with confidence, or even security. I was picked on mercilessly—teased, of course, but also actually beaten up from time to time.

It didn't help that I wasn't just small of stature but also small in the "manhood department"—s... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
2006
  |  
91%
  |  4

Successfully squirting like a sissy

After getting home from a long day of work i realized i would be alone for a few hours. I haven't came in a week. An all time record for me! Then i thought about using my toys on my sissy hole. My cock stands up throbbing with agreement. I thought about trying to make my cock squirt just by use of toys sad that i don't have the real thing.

I showered, cleaned out with a douche and stripped naked i sat down in front of my computer my cock rock hard.

Looking on xhamster i found a few sissy trainer compilations and bare-backing vids. The thought of a hard thick cock cumming inside me set me... Continue»
Posted by sub_guy_Sissy 1 month ago  |  Categories: First Time, Masturbation, Shemales  |  
939
  |  
100%
  |  5