Shemales Porn Stories
Page 68

Becoming sissy Jenny Part one

Hi, my name is Jonas and I´m 25 years old. This is the Story of how I became a sissy. So actually my name is Jenny now. But lets not get ahead of ourselves. The story has a slow build up, I hope it´s interesting for someone. Thats part one, I will continue the story from time to time. Everything sexual in this story happens to people over the age of 18.

I guess it all started whit my mom being a gold digger. One of those women who have a pretty face and a nice body and try to make a living out of it. After a few years of being an e****t, getting to know people, sucking the right dicks, gett... Continue»
Posted by jenny42 9 months ago  |  Categories: First Time, Masturbation, Shemales  |  
1846
  |  
100%
  |  2

Trip to the mall

So here I was again on a trip the the local mall. My wife the finest shopper of them all was in need of some new makeup, so the good guy i am decided to open my wallet and take her. (NOW before we go any further, I am a closet shemale and now even crossdresser fan for years) So upon arriving at the mall weake our usual rounds and eventually stop at her favorite chain makeup store, yes I've been there before. Today though as my wife was doing her thing with a female sales person, I noticed a very interesting young lad working. Now there is always what considered the "gay guy" working in these ... Continue»
Posted by Fnumo38 9 months ago  |  Categories: First Time, Gay Male, Shemales  |  
4082
  |  
100%
  |  1

getting used by many

I had been talking with Kevin now for about a month online. We kept talking about getting together, and he wanted to know how far I would go. I had told him that I was a total slut and loved to be used, abused and humiliated. He said that I would be perfect pig for him, and if I was real and not just someone online looking to tease he would take care of all my desires. Kevin said that he would set the ground rules that I must follow for our upcoming encounter, and I said I would.

Kevin told me that I would be picking him at the el stop after he was done work which would be around midnigh... Continue»
Posted by slut2eatcum 9 months ago  |  Categories: Anal, Group Sex, Shemales  |  
3383
  |  
100%
  |  2

Ronnie

“So, Ronnie, how about another drink?” George asked me.

“Oh, George, I’m so d***k, but what the hell, sure, I’ll have another.”

“Thassa boy,” said George.

“Let me hit the head, George,” I said and slid out of the tavern booth, then staggered to the bathroom.
Once inside, I locked the door long enough to take off my pants, then my jockey briefs. and stuff them in my pants pocket after I’d put my pants back on. I looked at my swaying image in the old mirror over the sink. I smirked and pulled down my fly, and pulled out my hard cock. Then I almost fell over, and decided to stick my co... Continue»
Posted by ssup28 9 months ago  |  Categories: Shemales  |  
514
  |  
100%
  |  1

P and I spend an amazing night with Ivy!

P and I have been buddies and fuckbuddies for a little while. We're both bi and we hooked up through my fiancee (she loves to watch us play together) and we found that beyond playing with her, we had a bit in common. We're the same age, but where I'm kind of bearish, he's smooth. My cock is thick with a big mushroom head and his is longer and thinner. We both love to suck and stroke together, although that's as far as we had gone until that night.

P called me one night, wanting to have a guys' night out. Drinking, gambling and hitting strip clubs and sex stores. My fiancee said to have fun... Continue»
Posted by Mrtommyboy 9 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
724
  |  
100%
  |  2

She knew what she was doing

Oh god she knew what she was doing...

The latex gloves fondling my aching balls, fingers squuezing and tugging as he hungry, made up lips worked my shaft.

Her moans were driving me crazy and it was everything I could do not to empty in her throat right there.

I remember trembling when I walked up the stone path to the front door. 29 and married for 6 years, but here I was about to knock on the door of a man dressed in womens under wear. A year of shameful and guilt wracked wanks to sissy and tranny porn, watching those soft cute trannys sucking and taking cock like real women.

Af... Continue»
Posted by DaRoyale 9 months ago  |  Categories: Shemales  |  
795
  |  
100%

Becoming Kitty

I guess I should start with that I've loved to wear panties. In school, I would sneak into my mom's room and put on her panties. While I was straight, at least so I thought, my fascination with panties never stopped.

In college, after my parents died in a car accident. I had my first gay experiences, including my first crossdressing experience for Halloween my high school. After my parents passed away and since I was an only c***d, I basically came out and began to openly experiment with my sexuality with both men and women.

However, my true passion was dressing as a woman and having se... Continue»
Posted by CumLovingKitty 9 months ago  |  Categories: First Time, Gay Male, Shemales  |  
3273
  |  
100%
  |  7

Meeting In The Woods

It was about 7.30 in the evening and the sun was going down, but as it was summer it was still quite warm.
I parked my car in the road across from the wood, then clutching my carrier bag I walked down the road a little then crossed over and went into the wood.
The place I liked to go to was about 200 yds into the woods and over by an old wall that surrounded a large section of the Whipps Cross hospital grounds, you wouldn't go over there normally as it went no where, so for privacy it was ideal!
As I walked along I could feel my stockings and suspenders gripping my legs, I could feel the st... Continue»
Posted by annette14 9 months ago  |  Categories: First Time, Masturbation, Shemales  |  
4983
  |  
100%
  |  7

Kitty's Weekend for a Huge Cock

I have to tell about an experience that I recently had with an old school friend. His name is Avik. I had moved far when I turned 15. We accidentally met one day at a mall. He was not able to recognize me at all and of course he was surprised to see me as a female because he had last seen me when I was 13-14 yr old boy. He was here for some work issues. We exchanged numbers and I got to know that he still stayed at our old town. It was good to know that he was bi and really interested in me too. After some days’ chatting we got the pleasantries out of the way, he sent me some pictures of his h... Continue»
Posted by CumLovingKitty 9 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
5478
  |  
100%
  |  4

Sony Sissy Diary

I parked my car and walked across to the entranceway of a 1960's block of private flats. Rang the bell of no. X and walked in as the buzzer sounded. Down the hallway and the door to one of the flats opened as I approached. He waited inside and ushered me down the hall, pointing to a bedroom and inviting me to keep my bag in there before going on to the lounge. He looked relaxed but I could only say “I'm very nervous, let's go and watch some Xhamster”, so we went into his study and he pointed me to the desk chair. I logged in and he sat beside me in another chair. I clicked up four of my... Continue»
Posted by Sonya_CD 9 months ago  |  Categories: Masturbation, Mature, Shemales  |  
790
  |  
100%
  |  7

camslutdiary

hey guys and gurls...this is a story i wrote after a proper camsession i had with my former onlinedaddy...i think some of you might knew him...c2cmaster...he had his own slutstable with a blog where he posted plenty recordings he mad while viewing his sluts on webcam...i found this in the depth of my harddrive and thought i should share with you...enjoy!!! This pic was originally shot before daddy popped online!



First of all I have to say that fully dressed long sessions with daddy are very rare. So anytime we planed... Continue»
Posted by TVgirlyJenny 9 months ago  |  Categories: Shemales  |  
353
  |  
100%
  |  1

My first time as a bottom and with a tranny

So this is the story about how i got my first experience being a bottom, and why it was with a tranny

I was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the tranny porn was the best. The idea of having a beautiful woman fuck me was very very exiting for me.
... Continue»
Posted by Pepmeister 9 months ago  |  Categories: Anal, First Time, Shemales  |  
9527
  |  
100%
  |  10

Owned sissy girl of dom couple Part 1

I met the mature dominant couple that I now call Mummy & Daddy on the internet. I am a 52 year old sissy who loves to be dominated, feminised and made to be a humiliated mincing sissy slut.
Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for two weeks prior to my arrival - a daunting task to say the least...
They answered the door together - he was a tall very masculine mature man in a suit, his trousers had a large bulge at the... Continue»
Posted by andrina62 9 months ago  |  Categories: Anal, Mature, Shemales  |  
1527
  |  
100%
  |  6

The shemale and the studio part 2

We had been doing some group photgraphs of a f****y. I moved to the desk to write out an invoice! George was still very old fashioned about some things! As I dated the invoice I suddenly realised that i had been working for George for a year now! Later when we were alone I told him. He looked surprised. He nearly said something to me but changed his mind! Something was happening to George and I suspected his partner Robin was behind it all.
He suddenly asked me if I would be free later on, there was something he needed to discuss with me> I said yes of course I was free!
Things went very qu... Continue»
Posted by dasilva1672 9 months ago  |  Categories: Gay Male, Shemales  |  
1708
  |  
100%
  |  3

My first time as a Crossdresser

Its 18 months ago. I had now become comfortable wearing womens clothes. I had been experimenting for around 3 months. I gradually started to get more confident in both my clothes ......and without. I started to dress more like a slut. Short skits. Suspenders. Corsets. I had also become more comfortable with my body as well. My hole was tight as could be. Like everyone, i started with fingers, one, two .....before moving on to small toys. After a few months, i had graduated to a 9 inch dildo.....although i still struggled.
I felt so hot. So right.

I had been chatting with other CDs and m... Continue»
Posted by mileslong34 9 months ago  |  Categories: Anal, First Time, Shemales  |  
3216
  |  
100%
  |  11

Going to the Gym

“I’m headed to the gym, baby,” the six-foot-three-inch two-hundred-sixty-pound Black man said to his wife of seven years.
“Ok,” she replied barely looking up at her beefy, brown-skinned husband. “I’ll be at the hairdresser by the time you get back.”
“Alright. See you later,” Darius Woodham smiled.

The former Division One linebacker started his black metallic 2012 Ford Expedition and backed out of the driveway. At the end of the street, he stopped at the intersection and pulled out his phone. He sent a message to the person he was heading to see.

Three months prior, Darius was watching ... Continue»
Posted by faggyboi 9 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
7454
  |  
100%
  |  3

Doing Time

Keno Reese finished his lunch of a chicken patty, one slice of white bread, baked beans, apple sauce, and two-percent milk surrounded by the other three hundred plus inmates at the prison. He walked his tray up to the front and hurried to his cell to sneak a quick call on his contraband cell phone. The former d**g dealer asked his mom to put a few dollars on his books via Green Dot. She agreed to send him fifty right then. He waited on the phone as she completed the purchase online. Then, the five-foot-ten-inch, slim light-skinned biracial brotha walked out of his cell and onto the yard.

Ke... Continue»
Posted by faggyboi 9 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
5260
  |  
100%
  |  2

Finally




Finally



I had decided it was time, finally, to try the experiences I had dreamed
of my whole life. I had been a secret crossdresser since I was a c***d,
and had hidden this side of me from my wife and c***dren. The last few
years of my marriage had been empty, staying together mainly for the
k**s and a kind of inertia. But now, they had grown up, married and
left the area. I knew I would only see them infrequently. With their
departure, my wife and I quickly came to the realization that we were
better suited to live apart, and the divorce had been quick and
am... Continue»
Posted by klammer 8 months ago  |  Categories: BDSM, Fetish, Shemales  |  
1974
  |  
100%
  |  1

Confessions of a cross dressing slut

Following up on my previous post.
Just to recap......

I had just had my first experience of sex as a cross dresser. My first kiss, first time my ass had been tongued, first time of sucking cock and first time fuck.
I had the taste for cock now, taste for cum. I loved it!!

I was now in the taxi home with all sorts running through my head....how great last night was, how much i turned him on, how much i was turned on, what to do next......as well as knowing this flirting taxi driver would love to fuck my ass.
We exchanged small talk and he flirted a little, passing compliment after com... Continue»
Posted by mileslong34 8 months ago  |  Categories: Gay Male, Shemales  |  
3160
  |  
100%
  |  6

The College Fantasy Part 3 (Futanari)

I was on my back in the bed. My head was at the edge and she stood over me stroking her massive fleshy cock. I was transfixed by her luscious tits and the warm tingling was intensifying. Her words, "open up my little cum slut," echoed through my mind and I could only resist a moment. She slapped my face and as I opened my mouth in pain she filled it with her massive futa dick. "Thats a good cum slut, take your time and enjoy my cock." She spoke slowly as I imagined the smile on her face.

I could see nothing except the space between her legs. He cock was long and fat at best I could ge... Continue»
Posted by fictiong 8 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
505
  |  
100%
  |  2