Shemales Porn Stories
Page 69

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 8 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 8 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 8 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 8 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Norman and Anastasia Part 2.

Luke and I follow Anastasia up the stairs. Her wrap round dress is tight across her big firm arse. Luke looks over his shoulder at me and grins. His eyes are level with that big swaying arse. She reaches the landing and opens the door to the bedroom. She hesitates a moment before walking in. She climbs onto the bed on all fours and Luke climbs up behind her. Her grabs the material of her dress and throws it over her back, exposing her arse God!! Where did Norman find her. On all fours behind her he buries his face into her crack and licks all the way up it. Reaching between her thighs he grabs... Continue»
Posted by dasilva1672 8 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Comicon

Carmen Bullard sat down the last plate of scrambled eggs, thick-cut Applewood-smoked bacon, and toast with strawberry jam in front of her husband of nine years. He was seated at the breakfast table along with their two sons aged seven and five. The boys scarfed down their own meals while Larry munched away perusing the digital copy of USA Today on his tablet.

“Are you all packed for your flight,” the fourth grade teacher asked.
“Yep. I’ll head out shortly after y’all leave,” answered the average height, stocky dark-skinned man.
“Well, be safe and call me when you land. Have fun! Come on ... Continue»
Posted by faggyboi 8 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Confessions of a cross dressing slut....1st BBC

So about 6 months after my first taste of cock, i began talking with another man on xhamster. He was dark, handsome and middle-aged.

He told me how much i turned him on with my pictures and how much he'd love to meet. The problem was, he was married and worked as a professional and couldn't be seen for the sake of his marriage and career. No problem. I told him we could be very discreet and no one would find out.

We agreed to meet in Manchester. He booked a hotel near the centre. I thought one outside the city would be better and more discreet but he said this one would be fine.
It wa... Continue»
Posted by mileslong34 8 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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DReft..

How I became a Bi GURL


So how did you become a bi gurl?

That's the question almost everyone I meet or chat with asks me... how did you become such a sexy transvestite, when did you figure it out, when did you learn you liked cock.

I actually love the question, because it turns me on to answer it.

When I was 15 or 16 I used to sneak into my parents room, find my dad's stash of Playboys and jack off to them. The girls were sooooo beauitful, I just couldn't believe it. I wanted to see and touch one, which led -- I guess this is common among us gurls -- to digging into my Mom's s... Continue»
Posted by Girliemagbator 8 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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Stepdaddy & Boi

‘Pomp & Circumstance’ began playing over the loudspeakers. The graduating class of Eleanor Roosevelt High School marched inside. The boys wore green robes while all of the girls were wearing white ones. In the stands, sat the f****y of Claro Booker. The s*******n year old’s mother, Belinda, was present with both of her s****rs. His stepdad rounded out the crew that came to cheer him on. He had been a star pupil. And finished in the top ten percent of his class.

When his f****y saw him enter, they clapped and yelled. The five-foot-eight-inch, two-hundred-pound, chubby medium-brown-skinned gr... Continue»
Posted by faggyboi 8 months ago  |  Categories: Gay Male, Shemales  |  
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Another College Experience

My Junior year of college was definitely the most sexually active time of my life thus far. Granted, I just started my Senior year, but thus far, I haven't kept the pace that I did last year.

I started crossdressing a few years back and do it in public every now and then as I look pretty feminine when I get dolled up. I have made it a habit that every Halloween, I would dress as something sexy and girly.

Last Halloween, I had a plethora of costumes that I wanted to wear, but ended up wearing a sexy sailor's costume. It consisted of a very short mini skirt, a very low cut top, and a litt... Continue»
Posted by wattheef 8 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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We Met at the Gym

This is my first story. Feedback is appreciated.
When I woke up this Saturday morning I was hornier than usual, but I had to suppress my urges in order to make a 5:30am group fitness class. I put on my normal workout clothes, Gray/ White Stripe Shimera Boyshorts panties, Nike loose leg shorts, t-shirt, hoodie, socks and New Balance cross trainers. I like wearing the boy shorts for two reasons, one- they are very comfortable and two, sometimes I like to have my balls hang down on either side of the crotch. About 5:15am, I walked into the gym, swiped my membership card and walked past the r... Continue»
Posted by randy1stonez 8 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Chance Meeting at the Gym

This is my first story. Feedback is appreciated.
When I woke up this Saturday morning I was hornier than usual, but I had to suppress my urges in order to make a 5:30am group fitness class. I put on my normal workout clothes, Gray/ White Stripe Shimera Boyshorts panties, Nike loose leg shorts, t-shirt, hoodie, socks and New Balance cross trainers. I like wearing the boy shorts for two reasons, one- they are very comfortable and two, sometimes I like to have my balls hang down on either side of the crotch. About 5:15am, I walked into the gym, swiped my membership card and walked past the rows ... Continue»
Posted by randy1stonez 8 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Being a good slutty Sissy

Being a good Sissy for my mistress

“Hey Martina. do you like what you see?” Samantha, a very beautiful shemale with tits size D, asks standing in front of me. A smile curls her lips as she strokes her 8 inch cock.

“Yeah, I'd love to play with a cock that big.” Martina says licking his lips at the sight of pre-cum dripping from the tip of her cock. I’m a 5 feet 11 tall sissy original called Mark. If I have to dress for my shemale mistress as a sissy gurl I call myself Martina.

“Well then, come and get it. on one condition. You're my pet until I'm satisfied.” Samantha says with a smile... Continue»
Posted by Arnie65 8 months ago  |  Categories: BDSM, Shemales  |  
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Stefan's Blackmail

When I was about 19 I started to crossdress. I didn't have gay feelings or strongly identify as feminine but I felt strangely attracted to my older s****r's clothing. One day I tried on a skirt and I found this simple act feel so thrilling that at the next opportunity I tried on a two more things...a dress and and a pair of her jeans. I was always thin, especially when I was younger, and my s****r was only three yeas older than me, so I had little problem fitting in most her stuff. Actually the stuff at the back of her wardrobe, the stuff a year or two old that she didn't really wear anymore w... Continue»
Posted by tricked-sissy 8 months ago  |  Categories: First Time, Shemales  |  
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Spanish adult book store

A few years ago , when I was still experimenting with my Bi side , I went to Spain for a few days , walking round early one evening I chanced on a sex shop , .I went in and it was huge , I saw things that I hadn't anywhere else , I was in heaven.

Going further in there was a sign for theater so going through a door I found myself in the room with cubicles and little video players , I was pretty nervous but went and sat in one and started watching the films,
again the content was so sexy and new , to me , straight gay , lesbian but most of all it was the shemales, I was transfixed.
I wat... Continue»
Posted by jakuk 7 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Mysterious Feminisation

After a few months of my ‘relationship’ with Stefan I realised that I had irreversibly crossed over the border between being a straight guy who liked to experiment with cross-dressing into being… well, something else. I am not sure exactly when this realisation hit me. Was it when I was pulling on a pair of tight girly jeans that I would pair with high stilettos and found I was not thinking how I might look in the mirror and how the clothes felt to me, but how sexy my ass would look to him? Or was it when in my day job I could still feel his cum still swimming around in my stomach from the nig... Continue»
Posted by tricked-sissy 7 months ago  |  Categories: Shemales  |  
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How I became Jayne The Crossdresser

It started in 1976,around August,I had just met John a guy my around my age,who lived alone near me. He wasn't shy to admit he was gay,and I was curious,and I told him one Friday after we got back from the pub about my interest. Before I knew it John & I had undressed & I had Johns cock in my mouth,sucking him off,& he soon quaked into an orgasm,cumming in my mouth so fast I gagged slightly before I managed to swallow most of it.John was keen to make it a pleasure for me & wanked me till I shot my jizz over his face & hair. This seemed to stir his dick & I watched as it hardened to its 6" and ... Continue»
Posted by tvluver2008 7 months ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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Sissy's first BBC

This happened awhile ago, i was 19, and i figure some people have asked me to write more so here goes =]

I was lookin around on craigslist... so i was horny and wanting it! Scrolling around and found a black guy who wanted some ass. No real specific requests, so i figured i may as well reply. In my town it is a bit rare to find black men who are down to fuck a sissy! I had sucked one BBC before while visiting North Carolina, sucked him off in a park which was great =] But that is another story and not nearly as entertaining.

So he replied back. Very little info. A pic of his cock... whic... Continue»
Posted by AshleyXmith 7 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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The Surprise

A divorced man finds love unexpectedly.

My wife left me a few weeks after my fortieth birthday. She ran off with a coworker, leaving me with our condo in the city. Getting dumped was a wake up call for me. I joined a gym and began working out and eating healthier. I was never fat or anything, but I got really lean and cut and began to feel confident in myself.

My friends looked out for me, inviting me out to dinner and fixing me up with friends. Maybe I wasn't ready to date yet, because there really wasn't any spark with any of the women they were introducing to me. I wondered if ... Continue»
Posted by magas911 7 months ago  |  Categories: First Time, Mature, Shemales  |  
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Shemale Surprise

A married man is seduced and taken by a friend of his wife's.

"You can stay with Robert if you wish," Mary said on the phone.

I looked up from my laptop where I was pretending to be working when, in reality, I was reading, for the hundredth time, the brilliant novella 'Shemale School: a Teacher Seduced'. The story had created a new obsessive fantasy I had never even considered before: to be with a Shemale.

I even contacted the authoress to tell her how much I enjoyed it, and have since became one of her editors. I had just finished editing a gay cocksucking story that, althoug... Continue»
Posted by magas911 7 months ago  |  Categories: First Time, Shemales, Voyeur  |  
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