Shemales Porn Stories
Page 74

I Knew I Was A Sissy (Part III)

The following months were pretty stressful. I was afraid that Nick may talk to somebody about me and then my secret would be exposed. At the same time I had to find a way to avoid hanging with those guys without raising any suspicions. I managed that by focusing on my classes and taking several extra ones. Nick didn’t talk so I calmed down. After Christmas I was relieved when my parents told us that we had to move in another neighborhood, that meant new school, new friends and, most importantly, long distance from the old ones.
I kept dressing at every chance; that means each one of the few ... Continue»
Posted by georgette32hk 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
2860
  |  
100%
  |  4

Dude Looks Like a Lady

Last night I was at a bar for a few drinks with the guys after hockey. We were joking, drinking and playing some pool. On the table next to us was a beautiful woman in her late 20's playing against her boyfriend. She had huge boobs that were spilling out of her tight tank top. I was having a very hard time concentrating on my game because every time she bend over to take her shot I got a huge glimpse of her wonderful rack. Her Boyfriend noticed I was staring and didn't look to pleased. He was also twice the size of me. After I finished my beer I told the guys I was tired and left. As... Continue»
Posted by niagaraguy72 6 months ago  |  Categories: Anal, Shemales, Taboo  |  
3894
  |  
100%
  |  4

Hitch Hiking across Europe

I wanted to go visit my cousin in Germany but couldn't afford it really, but on a whim I decided to go for it, just pack a few essentials and hit the motorway with my thumb out. Anyway to cut a long story short I finally got a lift from a couple in a nice big Mercedes, and started chatting, like you do about everything and nothing, when we came to a service station and they had to fill up with petrol and have a bite to eat, explaining i was kinda broke, the wife says that is okay, we will buy your lunch in return for a favour, and nothing else ......we sat have a meal and coffee, and the... Continue»
Posted by gkaye1954 6 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
2044
  |  
100%
  |  2

Paw-Paw and His Sub

“When you gone let Paw-Paw back in that ass, baby boi,” the sixty-six year old man asked.
“You tell me when you want, Paw-Paw,” cooed the short caramel-skinned twink.
“Aww, you know I want it now!”
“Come get it.”
“I can be on my way in thirty minutes.”
“Okay, baby!”

Rufus Clark went into the bathroom. He washed up. He put on a two-tone blue and cream long-sleeve walking suit, a pair of brown leather Stacy Adams slip-on loafers, and a brown Fedora hat. As he walked out of the house, he yelled to his aging mother, who lived with him, that he would be back late.

Rufus got in his green... Continue»
Posted by faggyboi 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
1101
  |  
100%

The Pill - part 3

This is the third chapter in the story of my adventures in London, on the day when I took a small pink pill and my face and body transformed into that of a beautiful young woman. However, I knew that I only had 24 hours before the effects wore off and so determined not to miss any opportunity as I had a day of sexual adventures, some planned, some on the spur of the moment. The story so far: I had started my day in the back of a van, in a multi-storey car park, choosing the outfits I would wear during the day, and discovering the wonders of my new female body. I had then greatly improved the d... Continue»
Posted by mallenwc 6 months ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
774
  |  
100%

The Booster and The Player

Princeton Wells soaked in the garden tub of his master bathroom and sipped on a glass of merlot. He relished the feeling of the bubbles tingling over his brown skin. He answered a text and relaxed some more. About five minutes, he stepped out and dried himself off. He lathered up with baby oil then put on his plush light pink UGG robe he had purchased online from Nordstrom a few weeks ago. He slipped into a pair of comfortable white house shoes and went into the bedroom. He pulled out a red lace thong and slid into them. Finally, he returned for his wine and headed out the door.

Princeton d... Continue»
Posted by faggyboi 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
697
  |  
100%
  |  1

Dichotomy of Life

Shane finished his final touches of getting ready in the hotel room. He made sure the gingerbread candle was lit. He lathered himself with cocoa butter and sprayed some perfume. The five-foot-eight-inch, one-hundred-forty-pound batty boi was so ready to see him.

Driving his silver 2012 Nissan Armada out of the parking lot on his lunch break, Chris headed towards the motel where his paramour was spending the night. He was barely a half-inch taller than Shane and weighed close to the same although he had much more muscle. He had met the brown-skinned vixen at a gas station.

Unbeknownst to... Continue»
Posted by faggyboi 6 months ago  |  Categories: Gay Male, Shemales, Taboo  |  
923
  |  
100%
  |  3

First time crossdressing with another CD

This is part one of a story, from a former user. I'd like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great.

First Time Crossdressing with a mate part 1


This is a work of fiction, though someday I hope to make it a reality.

-----

It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I dressed up like a slut for the first time, I couldn't stop thinking about meeting ano... Continue»
Posted by kumquat 6 months ago  |  Categories: First Time, Shemales  |  
436
  |  
100%

Bruce,,

As we all know the net has a wealth of information
about all kinds of sexual practices. In the fall of
last year I had began to read about things I never
knew existed. I found myself reading about BDSM, cbt,
tt, milking etc. It seemed that in any of these
situations where someone gave up control to another
person it exited me. I found myself overly excited
actually. Although I had never tried any of it, just
reading about it made my dick as hard as a rock. I
know that I love getting fucked and sucking dick but
these things sound even better. After reading so many
web sites I stumble... Continue»
Posted by klammer 6 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
1800
  |  
100%

Sissy gets first taste of latex, cock and spunk...

She imagined herself as a latex attired Dom with black thigh length boots, red corset, fishnets and a big black strap on cock who started by licking around her slaves balls and then behind them. She fantasised about curling her tongue into his dirty tight ass while she wanked him off, her tongue getting deeper and deeper.....Once his hole had opened and she had lubricated it with a generous drool of spit she slid first one and then two fingers to the knuckle in his tight ‘pussy’ and proceeded to finger fuck him. At first she went gently but then slowly started to pick up pace and vigour, addin... Continue»
Posted by Goosie 6 months ago  |  Categories: Anal, Fetish, Shemales  |  
1091
  |  
100%
  |  1

Cockatoo Part 4

Cockatoo Part 4

Return From Bangkok

It was late afternoon by the time my flight left Bangkok and dusk began
to fall about halfway back to Koh Samui. Lights from the fishing boats
in the Gulf of Thailand began to glitter like tiny jewels in the
gathering darkness. I could make out the dark shape of Koh Tao, and I
shivered at the memory of what had happened down there only a few weeks
ago. How close I had come to death in the cold, dark water, and how,
given a second chance at life, I was determined to make the most of it.

I spent half the flight worrying if I had made the right d... Continue»
Posted by nikkiesilk 6 months ago  |  Categories: Anal, Lesbian Sex, Shemales  |  
1950
  |  
100%
  |  12

Liquor Store Booty

“Barry,” called out Geneva Campbell. “Do you mind going to get a bottle of wine?” The attractive middle-aged woman made the request because they were expecting a visit from her cousin and his f****y since they were driving though the area. It had been years since Geneva had seen Marcus. On the phone with his wife, she was able to convince them to spend the night,

Barry yelled back, “Yeah. Give me a minute.”

The forty-six year-old, brown-skinned man shut down his game of Madden NFL 16 on his Xbox One. He walked out of the den to find his wife throwing together a casserole.

“Do I need... Continue»
Posted by faggyboi 6 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
2671
  |  
100%
  |  2

Christy’s Awakening.

“And you said you didn’t think you could do it!” John sounded surprised and to be honest I couldn’t blame him. He had just released his load deep inside of me with a loud moan. He was panting and trying to regain his composure and all the time I could feel him pulsating inside of me.

After what felt like an eternity he finally pulled out of me and rolled over. His eyes closed, he had the look that told me he was totally satisfied. I had surprised him this far, I thought, but I wasn’t satisfied, I needed more. John had woken the a****l inside of me. As he lay there, I slowly moved my ... Continue»
Posted by chuntercd1 6 months ago  |  Categories: First Time, Shemales  |  
2225
  |  
100%
  |  2

We all shared the rent, and they shared me!

It was my Junior year of college, at that point I was mostly a closet cross dresser, with the exception of Halloween, and a few select occasions. I had been sharing a house with two other guys, and I they both knew I would dress, but we didn't speak of it, well until tonight. I was sitting around doing shots and watching tv with my two roomies, let's call them Jon, and Barry. Jon was a small skinny Korean k**, who was very much influenced by Barry, the all American boy, tall, blonde athletic. Back to our story, the three of us started talking girls, and fucking, and moved onto "would you if ... Continue»
Posted by smonkeys32 6 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
5465
  |  
100%
  |  4

Crossdressing I Got Fist Fucked

I was feeling horny so I put on my blue satin dress with white polka dots, satin panties, my white satin gloves, garter belt & flesh colored stockings. Then I put on some deep red lipstick and lip gloss and topped it off with my blonde wig.

When I looked in the mirror and saw the sweet hot girl looking back at me I knew I'd find a guy who wanted to fuck me tonight.



I posted a picture of myself on Craiglist and within minutes I had half a dozen guys messaging me so I invited them all over.

The first guy who came to... Continue»
Posted by Doyoudeep 6 months ago  |  Categories: Shemales  |  
1330
  |  
100%
  |  3

My First Tranny Experience

I was in my mid twenties when I first became attracted to trannys. This was before the internet and it was harder to meet people, but I found an advertisement in a local newspaper for a TV named Susie who offered a massage service. I phoned the number and she sounded nice so I made an appointment.
I arrived on time at a small apartment block near the city centre. I was extremely nervous as I knocked on the door and waited for a response. The door was quickly opened and I entered, not knowing what to expect. I was very relieved as I walked in to see that Susie looked lovely. She was tall... Continue»
Posted by mjam21 6 months ago  |  Categories: Fetish, First Time, Shemales  |  
2650
  |  
100%

My Journey part 1.

My Journey.


As I sat in a small bar in a pub I thought back on my life and how it had brought me a Fifty year old cross dresser to this place and time.
Back in the late 70s and early 80s all the top shelf magazines were full of “lipstick lesbians” dressed in sexy satin and lace lingerie in various poses so when I got hold of some of those magazines the connection was made between feminine beauty, kissing, tongues, sex, satin and same sex love so all that was to follow in my life seemed to follow on from that for me.
I had began to enjoy satin ling... Continue»
Posted by silknsatinxxxx 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  
2278
  |  
100%
  |  6

Busted

Busted
Nikkie Silk
“Happy is what happens when all your dreams come true," Stephen Schwartz
Sandy came into the bedroom where I was still dozing, holding a pair of tights in her hand.
‘Babe, I wouldn’t ask, but I’m so pushed for time and I’ve just laddered my last pair of clean tights. I desperately need some before I go to this client meeting.’
She held them up as if to prove what she was saying.
‘OK,’ I said, still half asl**p, ‘what can I do about it?’
‘Can I borrow a pair of yours, pretty please?’
My eyes snapped open. What did she just say? I rolled over to look at her and my hea... Continue»
Posted by nikkiesilk 5 months ago  |  Categories: Shemales  |  
2263
  |  
100%
  |  8

Crossdressed Pigslut Takes a Cottage Assault

my sexual deviance is based largely around the high heel... of course with the females who wear them but also the nastiness i can get up to when wearing them myself..
i wont meet anybody for sex unless i'm wearing a pair of fuckme heels which are of a certain standard , the idea of wearing just stockings revolts me , as does wearing a pair of heels that i deem un-sexy.
the next obvious step up from wearing heels and lingerie and little black dresses is to be presented to somebody else who appreciates this sort of presentation. these somebodys are easily found online , however they can al... Continue»
Posted by THE-HEELS-STAY-ON 5 months ago  |  Categories: Anal, Group Sex, Shemales  |  
1195
  |  
100%
  |  1

The Cop & The Chubby

-Wyd?
-Watching TV. You?
-Laying in bed dick hard thinking bout your fag pussi hole.
-Oh wow!
-Come over tonite. My wife is getting ready for work. k**s are sl**p.
-What time?
-Be here at 11:30. You can stay til morn.
-OK.
-You know the drill. Park at the Krogers on Wynnton. Text me and I’ll come pick you up.
-OK Daddy. See you soon.

Russell Jones put his phone back on the nightstand. His wife of nine years exited the bathroom fully dressed in her scrubs. She kissed him before heading out of their two-story Dutch Colonial style four-bedroom house. She was on her way to the hospital... Continue»
Posted by faggyboi 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
1911
  |  
100%
  |  4