Shemales Porn Stories
Page 5

Maybe


As I stepped into the department store, I had to resist the
natural urge to turn left and head for the electronics section.
Instead, I turned right, penetrating deep into the mysterious
world of women's apparel. Feeling conspicuous, I tried to look as
if I belonged, relieved that there were no crowds so early in the
day. This was the third time I had attempted this, and I was
determined not to chicken out again.
I knew what I wanted, but not where to find it - and I was
far too nervous to ask for help. Of course, it ended up being in
the last place I looked. Wandering anxiously... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  
723
  |  
100%

BEA 2016

first time – anal – oral – shemale – dominant shemale – submissive male – rimjob

Book Expo America. Here we go, again. Will it be the same thing again?

Fly in, get the baggage, take a smelly cab to the hotel. Meet my Sales Director, Victoria (who goes by V), in the bar.

"We've got to set up the booth, Jack. But first, let's have a drink or two!" She winked. V has been my boss for five years. She rode the team hard for sales numbers, but she was fair. We had up years and down years, she knew there was only so much that was in our control. I was her go-to guy. It always felt good... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Anal, First Time, Shemales  |  
4175
  |  
96%
  |  6

Bikini Boy

boy in panties – bisexual threesomes - bisexual lust – s****rs' panties – boy on boy sexfest – crossdressing pleasure – luscious girl on girl sex – secret lingerie stash

I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage. Then came the divorce. The fights, the yelling & screaming about the "other woman" resounded through the house & the k**s tr... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
7166
  |  
97%
  |  4

Our Trip to Vegas

Tim & I flew to Vegas to meet with a client to sigh some contracts. We met with the client, signed the contracts and were going to spend the rest of the time doing some gambling and seeing the sights. We were in the bar at one of the casinos having a drink when a gentleman came over to us and said you’re Shauna Riley, aren’t you? We had never seen the man before but I answered yes I am and asked how he knew me. He smiled and said he had seen my pictures & chatted with me on Xhamster. This brought a smile to Tim’s face. We invited him to sit with us. After talking for about a half hour he asked... Continue»
Posted by shaunariley 1 month ago  |  Categories: Gay Male, Group Sex, Shemales  |  
4690
  |  
96%
  |  16

MY PORN SHOP CONFESSIONS

AZNSWAG

if you read my blog on my profile , you can see my background into how i got into the porn shop business..
i thought it might be fun to share some of my personal stories: things that i have seen & done while working at the many different porn stores across my city. this is one of my many experiences that i will never forget


ill just name it.. my porn shop confessionals =)

i worked at this particular porn store from 2006 - 2010. usually porn stores are very hidden. usually they are in some abstract location where privacy is held to its highest... Continue»
Posted by AZNSWAG 1 month ago  |  Categories: Shemales  |  
1742
  |  
100%
  |  3

Transformed Into A Shemale

crossdresser – leather – virgin – shemale – lingerie – thrusts deeply – clad cock – tight denim

I was 18 when I first had sex with a man. This is the story....

I am a very hot looking guy. I say that knowing that some may consider me vain, or arrogant, but over the years I have had so many women and men tell me how fine I am, that I know it is true. I am 35, blond and blue eyed, 6'1," 180lbs, with a tan athletic body and a 7" beautiful cock. I have been dressing up as a sexy girl ever since I was 18 years old and had my first experience with a man. The following is how it all star... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
3463
  |  
95%
  |  4

Jamie's Descent Part 2

Chapter 2


'That's it, baby,' Vanessa purred as she snaked her hips forwards and
back, gently sliding the strapon in and out of my mouth. I could no
longer think rationally, as any self control I still had slipped away and
trance like, my eyes closed, I sucked the rubber phallus in and out of my
lips.

'Baby, you love this don't you?' Vanessa's voice took on a hypnotic
tone, gently encouraging me to take more and more into my mouth.

I was too far gone with lust and desire to even register the question
let alone give her any answer.

'This is what you want, isn't it? You w... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: Anal, First Time, Shemales  |  
1414
  |  
100%
  |  4

Becoming a Slut

slut



Fuck I been getting down on my knees for a few years now, every since I was
caught given a guy a blow job by my father. Fuck lets start at the
beginning .

My name is Peter I live in the united kingdom in the north of England they
are quite a lot of chavs here and I used to get bullied a lot at
school. One day while I was skipping school I met a guy in the toilets in
the park.

I am quite effeminate long hair smooth pale skin and very skinny I am only
5'4 so small for my age and I am 14 my mother died when I was eight from
cancer and I have four older b*****rs I always w... Continue»
Posted by klammer 1 month ago  |  Categories: Fetish, Shemales  |  
1870
  |  
100%
  |  1

Steps****r

It started back in my sophomore year of high school. My father
was overseas with his construction firm on a six month build when my aunt
Marie had her accident. My mom wanted to fly up to see her in the hospital,
but it was the middle of the school year, and she didn't want me missing
any classes. That was when a neighbor of ours, and a close friend of my
parents', offered to let me stay with her and her daughter while my mom was
out of town. She promised to feed me, make sure I didn't stay out in the
rain, and make sure I was on the bus every morning. My mom was usually
incredibly pro... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
9894
  |  
96%
  |  6

Slut, maybe..

Slut

I was on my back in the middle of my neighbors king sized bed getting the
hell fucked out of me by one of his friends. Not only that, but I was
dressed like a slut. I used to be a teenage boy, but now, I am a
girlie-boy. A girlie-boy who's out to swallow as much cum and get as much
cock as she possibly can. How I got to where I am now is what I am going
to tell you about. But for right now, I had my knees pinned back and my
(still) tight asshole was getting a brutal pounding. I had my arms wrapped
around the broad shoulders of a very large man, holding on as best as I
cou... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
4116
  |  
94%
  |  2

Jamie's Descent Part 1

Jamie's Descent

Nikkie Silk


Chapter 1

What did we do before social media? How did we manage to get through
the day without that endless stream of dirty jokes, funny photographs,
gossip and links to dodgy websites that now fill our lives? Yeah,
yeah, I can hear you grumble. Get on with it, I can hear you say. Well,
dear reader, it was one of those links that started me down the road
to... oh, you'll find out soon enough. I was 18 and I had just come
down to London from my hometown in Norfolk after leaving school.

A friend of my father's had offered me a job in an off... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: First Time, Shemales  |  
1308
  |  
100%
  |  5

My first shemale experience

so i've read plenty of stories on this website and thought I would share my own with you from 2011

For years I had fantasised about being with a ladyboy, but didn't know how to go about it as I didn't want to pay for an e****t.
I found a ladyboy dating website and created an account, it cost $30 for the month but was still cheaper than paying for an e****t and slightly more classy.
After about a week of sending messages to compatible matches, I finally got a response from an Asian TS who was visiting from Malaysia. She said she liked my photos and wanted to meet with me that weekend, so w... Continue»
Posted by mick_c1990 1 month ago  |  Categories: Anal, First Time, Shemales  |  
1245
  |  
100%

Cockatoo Part 11

Cockatoo Part 11
Nikkie Silk

Areeya returned to the apartment sometime after we had gone to bed as the moorings needed more attention than Areeya had initially thought. After she and Shane had eventually got Cockatoo 3 safely secured on the pier, he had gone back to his hotel and Areeya headed back to get some sl**p in the apartment.
In the morning I had changed back into being James, albeit with a little reluctance. Alex had suggested I go on the boat as James and change into Scarlett for the evening. I thought it was one of Alex's better ideas as I didn't have anything suitable for the... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: Shemales  |  
898
  |  
100%
  |  3

Be-cumming a School Girl

Be-cumming a schoolgirl
From the time I was 5 or 6 I would sneak into the lodger’s bedroom after she had left for work. I would dress up in her lingerie and climb into her warm bed. It just felt so good wearing silky clothes which felt so delicate against my skin. I just loved to feel feminine. If anyone looked in I would pull the covers up to my neck to hide what I was wearing. A few years later I would be wearing my elder s****r’s panties and occasionally my mother’s when she was out. I guess she was suspicious because one day my s****r caught me out and paraded me in front of my parents ... Continue»
Posted by Sally5050 1 month ago  |  Categories: Shemales, Taboo  |  
3917
  |  
93%
  |  2

Room 209: First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – bra

I've been crossdressing for much of my life, as far back as I can remember. I would even go to sl**p as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight for some time so I have breasts. As a man, I have to minimize them all the time. As a women,... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: First Time, Fetish, Shemales  |  
1396
  |  
100%
  |  3

Mayberry, the Black Goddess

tranny – shemale - cocksucking – anal – spanking – domination – submissive

Another lonely night led me to walking down the dimly lit street and wandering into the sex shop. There wasn't too much adventure to be seen there, very comparable to my apartment.

I was looking at toys. Specifically, butt-plugs. Not that I didn't already have one; in fact, I was wearing one at the time. The little bell above the door rang.

I looked at the cashier, she stood there- blowing her bubble gum. I couldn't see who just came in. I was curious. I continued to look at the toys. I squatted to get o... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
1630
  |  
100%
  |  4

abused shemale toy strikes back

These are excerpts from a horny chat i had with a guy. All I did now was taking out our sidetalk and try to correct any errors, since we are both non native english speakers. he knows it is used here and I am sure the story will continue. I'd love some feedback to see if i will upload the next parts.
The story includes rough sex, dominance, breath play, v******e, and generally hardcore stuff, so if you are offended by that, stop reading. Since they are from a chat, perspective will change between us two, so everything from his perspective will be bold.

I come home to you. You are stan... Continue»
Posted by hikahuk 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
470
  |  
100%

Daniel Effeminate College Student Chapter 2

Chapter 2
The Party
At the end of their successful meeting Serge invited Adrian and of course Daniel to a party at the home of his employer for that evening. It was an event with a large number of people invited from the arts and business community artists, buyers and supporters of the arts and some musicians and a few from the theatre community. Adrian and Daniel arrived together and Daniel looked spectacular with his new hair style and wearing one of the new outfits which were purchased that afternoon. He felt wonderful and as he entered the large foyer. He looked in a huge mirror and admi... Continue»
Posted by colourfast 1 month ago  |  Categories: Gay Male, Mature, Shemales  |  
491
  |  
100%
  |  3

Daniel Effeminate College Student

Chapter 1
The Beginning

Daniel, an Italian boy in his late teens is starting a fine arts program at a college in the US. He had been awarded a full scholarship as part of an exchange program with the international arts community. He arrives before classes begin and has to stay in a hotel at his expense as the residence on campus in not available for a week. He is happy to be there as this is freedom for the boy as he can now begin to express his true desires to be gay and effeminate. At home it was not possible with the closeness of his f****y, friends and values of his community. However ... Continue»
Posted by colourfast 1 month ago  |  Categories: Gay Male, Mature, Shemales  |  
1938
  |  
100%
  |  3

The Apartment Part 2

I had found myself a new flat but was just discovering that it came with strings attached. I am not sure, but they are into swapping partners at a party. I was at my first.

I was sucking George's little fat cock while his tranny wife fucked me from behind. While we are in full flow, the other couple come into the party. Roger and Diana. Diana was a plump thing with a sweet cock while Roger was tall and thin. His skin was very white and covered with dark hair. His cock was hard and he stood in front of me while Diana kissed me! She moved from me to George holding her cock out for him to suck... Continue»
Posted by dasilva1672 1 month ago  |  Categories: Fetish, Shemales  |  
2249
  |  
100%
  |  1