Shemales Porn Stories
Page 75

The Making of a Sissy (Part 1)

It was the summer after graduation, and I was living with my mom who was recently divorced. She had been dating a lot during that period, which was kind of rough for me to deal with. I would usually give her dates a hard time, and to be honest I was completely unsupportive of her decision to be dating. Anyhow, I was up late one night watching something on t.v. when I heard her and her new boyfriend come home from a date. They were apparently somewhat d***k and making a lot of noise, but I just tried to ignore it. It wasn't much longer until I started to hear this moaning and rocking of th... Continue»
Posted by briantid8 6 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
8871
  |  
100%
  |  10

Break Down

Pu-Pu-Pu (Cough). Rattle. Hisssssss. Bang!

Robynn's car gurgled and grumbled, slowly crawling along until finally coming to a complete halt.

"Uggg . . . Not again!!" Robynn teared up in frustration. "Not now!" With all of the burdens she was currently carrying this was like the straw that broke the camel's back. As would be expected with most Sissies, Robynn wasn't mechanically inclined and had no idea what was wrong with her car. All she knew was that she was stranded in the middle of nowhere.

Honk! Honk! Honk! vehicles were expressing emotions since she was still in the middle of th... Continue»
Posted by amberfemxd 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
2627
  |  
100%
  |  3

Playtime Stories Ch 11 - Carla the Theater Whore a

11.

After I was done stage fucking the nice-tiitted dirty-blonde school girl in her thirties, Carla had lined up some more meat for us. She’d been “working” the crowd while I had the blonde bent over on her knees. Carla and I sucked off about three more cocks each before the crowd waned. It was late. Carla offered to take me to her place and although I really wanted to go, I had to make sure I made it to my meeting on time in the morning. I knew it was past three o’clock in the morning.
We compromised because we knew we both wanted to fuck each other. We’d both been sucked and fu... Continue»
Posted by 6988slutty_rbckyy 6 months ago  |  Categories: Anal, Hardcore, Shemales  |  
815
  |  
100%
  |  1

Playtime Stories Ch 14 - Masters and Subs Stop by

As with the story line of Ch 13, this one is mostly fantasy except the Master Titan and 'Hole-boy'. They are people I met but couldn't play with (yet).

14.

I stood up and tucked myself in almost making myself cum in the process. I looked at him with a quizzical expression as I stood and walked to the door, wondering what I’d gotten into. I asked him if he was sure it was safe. He said I was in no danger and everything was going to be fine.
I looked at myself in the mirror to see that my makeup was still fine, despite my phenomenal cocksucking. I still looked a cheap whore with... Continue»
Posted by 6988slutty_rbckyy 6 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
477
  |  
100%
  |  1

The Making of a Sissy (Part 2: The Metamorphosis)

As the morning rays of sunlight pierced through my bedroom window I was awakened from the most intense dream, reenacting what had happened the night before. My throbbing hard little cock was gently humping against the sheets of my bed while I couldn't stop thinking about the amazing big black cock I had in my mouth just hours ago. I could still taste him on my tongue, and I could smell him on my lips. What had happened to me? Why was I so turned on by all of this? I thought to myself, "Maybe it was just a one time thing, like a one night stand." My mom had been dating a lot lately, so I ... Continue»
Posted by briantid8 6 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
11659
  |  
100%
  |  13

Gangbang at Ricks part 2

Gangbang at Ricks part2
Don said were here you sexy slut, helped me out of the car, grabed my butt arm around me like he was showing me off look what i have for the party, opened the front door Rick and 6 of his buddies with just shirts on, a few of them stopped sucking. Everthing got quite for a min. when Damn our Hooker is over dressed, who's first, I should have tape measured it was close to 90" of cock all for me? The party just started. Sex music, some guys saying Danm, good head, I know I should have tryed getting my cock sucked by a guy, years ago, as we walked in to the front roo... Continue»
Posted by mrheat22 6 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
947
  |  
100%
  |  1

Kate monday evening

Kate turned to sally , what time are you leaving,
I'm being picked up at ten
I stood up and rinsed my mouth out
The girls were talking, Sally giggling
the Kate said Christine call Paul ask him to come round
Why ?
I want to film the pair of you
What no Kate please I responded
Christine do as your told, you just cum watching sally and me, so why don't you want us to have the fun of watching you two

I had no answer and I didn't want to upset Kate
I phoned Paul' his dad answered the phone and told me he was over the park playing football

I told Kate OK she said we will go over and... Continue»
Posted by sissychris 6 months ago  |  Categories: Fetish, Shemales, Taboo  |  
750
  |  
100%
  |  1

Christean a personal story of lust

Christean a story of personal lust

This not meant to be porn so apologies if you feel it is. It's the actual life of a porn addicted cross dressing bisexual, other- wise straight man ( well maybe not so straight ) with in exhaustive chronic need to be sexually stimulated.
He lived with a tier of secrets. For most of his life the secrets Christean held inside barely acknowledged and some which were not yet discovered.
In the current days Christean or Phynick has fully blossomed into a gorgeous horny slut gurl.
By slut gurl I mean he is a guy who is bisexual or actually pansexual but loves... Continue»
Posted by Christean 6 months ago  |  Categories: Fetish, Shemales, Taboo  |  
282
  |  
100%
  |  1

My 1st transgender experience

A recent addition to my friends list had a story about his first shemale experience which inspired me to write mine.

Many years ago I was living near the San Francisco area. I had purchased the most recent Hustler magazine and one of the layouts had Shannon. She was so beautiful, and oh my what a cock. I had only ever been with women and did not consider myself gay, but for some reason I wanted to suck that cock. I cannot recall how many loads of spunk I blew looking at those pages of Shannon, she was so gorgeous.

Realizing I wanted more than pictures, I borrowed a tabloid from a friend ... Continue»
Posted by francisjoe69 6 months ago  |  Categories: First Time, Shemales  |  
2795
  |  
100%
  |  4

Dressed for Sucksex

Dressed for Suckcess

(DISCLAIMER: This story is part reality/truth, and part fantasy. Please feel free to comment.)

It had been a busy time and I had not been out as Danielle for several weeks. I was so aroused I could hardly stand it. I had arranged to meet two of my crossdressing girlfriends at a bar that was tgirl friendly. We often hung out there since it was safe and there were a number of male admirers there. These guys were there to meet us so they were almost always clean and polite. I had already prepped my ass so I was completely clean and had lubed up hoping for some a... Continue»
Posted by Chrissycdslut00 5 months ago  |  Categories: Shemales  |  
1077
  |  
100%

A COMING OUT PARTY

We had met on XHamster.com. Our profiles confirmed we lived in the same city. We exchanged private messages at first then we started exploring mutual fantasies. How we like to dress in women’s clothing, especially the lingerie. We shared masturbatory stories with one another. Finally, we agreed to skype while we were dressed. We wore masks for our mutual protection. This went on for a few weeks until one day he took his mask off. What could I do? I had to reciprocate, even though I was terrified of being outed. No one, not even my wife knew of my little hobby. I had managed to keep it hidden f... Continue»
Posted by justluvtrans 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
6216
  |  
100%
  |  16

My story (Part 7) "Medical Lab Encounter"

Medical lab encounter

After I started taking hormones I met online a human laboratory doctor. I told him about taking the hormones and that I want to make full analysis for a Transexual and that I also want to take a prostate liquid sample. At first he thought I was not real till we set a date to meet at the lab he works in.

When I arrived at the lab, I walked directly towards the receptionist and asked for my Doctor friend. He called the doctor on the phone and told him their is a Sherry here asking for you Sir, then he asked me to sit a couple of minutes and the Doctor will come to me... Continue»
Posted by sherryladyboy 5 months ago  |  Categories: Anal, Fetish, Shemales  |  
1159
  |  
100%
  |  2

My story (Part 6) "Marriage as a male disaste

Marriage as a “Male” disaster

At a stage in my life I have doubts that I had a problem of being such a slut and wanting to be a women. So I decided to stop and try be normal, for sometime I could overcome my desires and so on. And thought I was cured, but actually it was all an illusion.
So I decided to get married and try to live a normal live. After sometime I got married to lovely decent lady that I really liked. But it was not love or anything of that. We got married after half a year. My first impression was that she was ver traditional sexually, and thought that the man does everythi... Continue»
Posted by sherryladyboy 5 months ago  |  Categories: Anal, Fetish, Shemales  |  
317
  |  
100%

a night with Master

As instructed I stood in front of the correct door, slightly early (definitely not late!!), my entire body waxed smooth and feeling more than a little bit exposed on account of wearing a super slutty outfit specially selected for me by daddy.

Nervously I knocked, hoping my appearance would be pleasing for daddy, and heard the words which made my heart skip a beat "come in"

Once inside I was ordered to kneel and thank him for the honor he had bestowed upon me by starting at his feet and kissing my way up to his rock hard cock, (which filled me with joy knowing that using me turned him on ... Continue»
Posted by slaveboyinadel 5 months ago  |  Categories: Anal, BDSM, Shemales  |  
889
  |  
100%

Cockatoo Part 5

Cockatoo Part 5


Following the call to Kritsada, I stayed in Cockatoo, chatting to Nin
who had brought me another beer. I asked her to join me for a while, and
we talked about last night. She had really hated Tony and was delighted
with what we had done. I was quietly impressed; she was pretty, her
English was excellent, had a great sense of humour and a charming
personality. I didn't know if Alex or Areeya had mentioned the job to
her, so I didn't say anything, preferring to leave it to the girls. I
asked her again not to mention anything about Sam to Areeya or Alex. She
was obvio... Continue»
Posted by nikkiesilk 5 months ago  |  Categories: Shemales  |  
290
  |  
100%
  |  6

Gangbang at Ricks part 3

= Gangbang at Ricks part3
There i was knee deep in Big Cock. I don't know why Guys like fight over a girl or gal the want to pound some Hot Wet, Tight, Hole real bad like a Bull. Wait a minute, I got to thinking, I am a guy in girl xxxy cothing. I got up told them all lets settle down, I was fresh fucked, Don his BBC, I was still Letting Daddy Rick up and my big load in his belly, he shot all over the sheets, He got up told me to clean up his mess, he made. Face down in his big load, Some one gave Rick the paddle, My BB was the ... Continue»
Posted by mrheat22 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
3483
  |  
100%
  |  1

My first BBC

Ever since I discovered "BBC" on the internet, I have always wanted to play with one. Before then, I had no idea that black men were into white sissies. In my mind I had them stereotyped as the type of man that would never have anything to do with a crossdresser. I thought they were too good for us. How wrong I was when I made my presence known on various websites. BBC's, handsome, well hung, BBC's from all over the world were telling me how hot I was and how they wished we lived closer so we could hook up.

That last part was killing me! Virtually every BBC I met online lived too far... Continue»
Posted by Cum_on_Eileen 5 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  
1279
  |  
100%
  |  1

Oh What A Night!

As the old 4 Season's song stated, oh what a night.

Having been a crossdresser on and off my entire life, I have done the old collect and purge routine too many times. After putting Jennifer away several years and relationships ago, the old urges returned recently. Having lost a considerable amount of weight and working out my feminine side emerged once and again, and boy am I having some fun. More about that in a later post. For now I want to share one of the hottest nights I have ever had while dressed.

Two weeks ago while my permanent fiance was at work I had a full 7 hours to play... Continue»
Posted by dicklover4two 5 months ago  |  Categories: Mature, Shemales  |  
517
  |  
100%

The nasty EXGF

We all have heard the stories, XGF who never did the nasty things we wanted to do, she told you that it was disgusting or perverted. Yea, only time can erase that lie.
Went to New Orleans few months ago, needed the break and to see the seedier side of the quarter. Walking thru the quarter I was inundated with all forms of humanity, some beautiful, others of questionable heritage but all were enjoying themselves. One particular bar was of interest and featured excellent drag shows.
After getting my drink and situating myself close to the stage, I settled back to enjoy the view.
The first few... Continue»
Posted by sprchf69 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  
2051
  |  
100%

I Knew I Was A Sissy (part V)

Time passed and here I am a freshman at University. I am leaving alone for the first time in a place far away from my hometown. I am excited as I finally have the freedom and anonymity to be who I want to.
The first days passed exploring the area around my studio apartment; my school was downtown so there were plenty of choices. I spotted some nice gay bars as well as places to shop underwear, dresses, heels and boots. But I started with a nice waxing. I found this place which was a bit far from home so discreet was guaranteed. I did a full body hair removal and when I returned home I kept l... Continue»
Posted by georgette32hk 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
2680
  |  
100%
  |  3