Shemales Porn Stories
Page 69

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 7 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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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 7 months ago  |  Categories: Shemales  |  
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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 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 7 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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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 7 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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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 7 months ago  |  Categories: Masturbation, Mature, Shemales  |  
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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 7 months ago  |  Categories: Shemales  |  
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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 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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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 7 months ago  |  Categories: Anal, Mature, Shemales  |  
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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 7 months ago  |  Categories: Gay Male, Shemales  |  
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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 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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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 7 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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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 7 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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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 7 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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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 7 months ago  |  Categories: Gay Male, Shemales  |  
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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 7 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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First Time With A Guy And First Time As A Gurl

worked summers in a factory by my house when I was in college. Nice, clean summer job. Charlie, the Chief Engineer was my boss. He played Div. 2 college football and still was in great shape. Thick arms and legs, big hands, broad shoulders. He was going a little bald, but otherwise...anyway. I wasn't into guys, so I didn't notice those little 'things'...signals, whatever. I had a somewhat steady girlfriend, but she went abroad that summer.
Being 19 I was, it seemed, always thinking about sex. Loved jacking off to the 'Men's Magazine; I found in the guys locker room. I especially found the Fre... Continue»
Posted by keripinkpanty 6 months ago  |  Categories: First Time, Shemales  |  
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divorced

After I was divorced from a 20 year marriage with
bland sex I met Marcella. She tuned into my
unfulfilled fantasizes and told me about her wild
sex life. After she introduced me to my first three
some with a black boyfriend I was hooked and we got
married. After that, my life was full of depraved
raunchy sex and even cross-dressing. (MF, MM, 1st-bi,
oral, anal, swingers, alcohol, cd, orgy, voy)

***

Marcella and I were a perfect match. I was in my 40s
and just out of a 20 year marriage with all sorts of
sexual fantasies She was divorced, in her 30s and
scaring guys off ... Continue»
Posted by pcarter 6 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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The College Fantasy Part 4

I walked towards the bathroom where she had gone before me. I was in a daze. The reality of what had been happening was sinking in and my body would not stop the incessant tingling. It felt like my skin was heating the room. A cold shower sounded magnificent.

The water was already running. I could hear it from the hallway. When I turned the corner into the bathroom she stood before me. Her whole body was exposed and for the first time I was able to observe all that had changed. Her tits had grown from the C cups they once were to D cups. Her feminine figure was as beautiful as ever... Continue»
Posted by fictiong 6 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Part Two: The Carpet Guys Koni Gets Ruined

Richard said something to Juan and they both laughed as I laid there in puddles of my own goo... my face covered in cum and stoned out of my sissy mind, I knew I couldn't get up. Richard pulled his pants up, leaned down and with his heavy accent, said, "chica our boss, Mike, will be here soon to check on our job... You'll need to tell him those big wet spots are from you okay? It's not our fault... " he stopped and snickered, "that you can't control yourself ya little slut." Both men laughed and went back to work. I couldn't get up. My body felt so heavy and sl**py. I didn't care who walked i... Continue»
Posted by Konicum 6 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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