Shemales Porn Stories

The Roommate Pt. 01

feminization – transformation – sissification – femdom – blackmail – anal masturbation – cock worship – crossdressing – whoring/prostitution – sissy

I lean forward, staring at a big cock going in and out of a girl's tight ass on my computer screen. I'm jacking myself off so hard, and I can feel the thong pressing against my asshole, I don't know why it's turning me on so much right now. I'm getting close, and stare intently at how the cock rhythmically thrusts into her ass. Suddenly, my cock erupts cum into my hand, filling it and then some with a huge load. A feeling of shame washes... Continue»
Posted by naughty_bi_interest 1 hour ago  |  Categories: Anal, Fetish, Shemales  |  
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Daddy's Girl








Daddy's Girl

The Hitchhiker

It had been snowing all day. A wet, heavy incessant snow that was covering everything including the highway. Combined with a wind-chill factor in the teens, Christopher was almost frozen stiff. He was elated when the huge semi pulled over to pick him up. He climbed up into the cab and smiled thankfully at the driver.

"Thanks a lot mister. I was just about frozen out there."

"No problem, son." The driver smiled at him. "Name's Zeke," the driver said and extended his hand.

Christopher took the offered hand and shook it. His hand seem... Continue»
Posted by sissirandi 6 hours ago  |  Categories: Anal, BDSM, Shemales  |  
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A Dream Cum True

As part of the national sales f***e for my company I travel quite a bit for my job. As a result I have a lot of time to explore my sexual proclivities. I have taken to collecting panties, bras, nylons, a few wigs and a little bit of makeup that I often bring with me because I travel regionally and drive a lot. I like to meet up with strange men in my hotel room where I get dressed up, get on my knees and suck cock. At first it was just other gurls who like to dress. While they remain my favorite I soon discovered I just like sucking cock. If I’m dressed and feeling girly I’ll suck a man’s coc... Continue»
Posted by smilinwillie2001 7 hours ago  |  Categories: Shemales  |  
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My first encounter with a man

As usual when I was travelling I was sitting in my hotel room working. I finished my work while drinking a beer or two, as the tingling feeling started to grow. In my suitcase I had packed my outfits and my toys ready for some hotel room action. Although; action meant myself, porn and self-satisfaction.

I took a shower and washed away all the dullness of a day on travel. I was stroking my cock and balls gently feeling the hairless skin glowing, and my cock started to grow. Since I was eager to save up for a massive load I finished the shower and started to get dressed.

The black panties ... Continue»
Posted by theevilothertwin 8 hours ago  |  Categories: Anal, First Time, Shemales  |  
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Shemale Surprise

anal – shemale – transgender – transsexual – oral – pantyhose – first time – stockings – wedding – lesbian

"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 e... Continue»
Posted by naughty_bi_interest 4 days ago  |  Categories: Anal, First Time, Shemales  |  
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Jamie's Descent Part 4

Chapter 4

Fiona stood in front of me and said sharply, 'Stand, slut!'

It was a tone of voice that made you think arguing about it wasn't such
a good idea. I got up as quickly as I could, nearly falling over in my
haste to obey. The tip of her pink tongue appeared and slid along her
full lips. She had seemed tall before, but now she towered over me. I
saw that somehow she had put on a pair of spike heels; open toed sandals
really, with two-inch spikes and thin leather straps that fastened
around her ankles. Her toes were painted a vivid scarlet and I wondered
what my toes would lo... Continue»
Posted by nikkiesilk 5 days ago  |  Categories: Gay Male, Shemales  |  
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Picking Up a Sissy at the Grocery Store

Not my story, but very hot:

I saw you while I was walking through the grocery store. You were bent over, picking up something off the bottom shelf. At first, I thought you were a girl, because of your nicely shaped ass and the fact that your low rider jeans were riding down, exposing a lacy white thong.

I was so turned on, my cock started to get rigid right away. If I had been wearing jeans, I probably could have hid it, but as I was coming home from work, I was in a suit and tie, and the thin fabric of my suit pants did little to reveal my hard dick.

I walked up to you, expecting to ... Continue»
Posted by widendeep 5 days ago  |  Categories: Anal, Gay Male, Shemales  |  
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Football Mascot – Gabi

Football Mascot – Gabi

Gabi was sucking on his favorite dick stick, the one owned by the black tackle of his dad’s football team. Talon was massive all over, but especially his cock. One of Gabi’s hands was sliding up and down on it. Gabi’s other hand was stroking the massive cock of the Center on the same team. Larry was white and even heavier than Talon but his cock was slightly, but only slightly, smaller. Pedro was between Gabi’s legs using his own massive cock to gently slap back and forth against Gabi’s sweet peter. It was a game invented by Gabi. Pedro was the Latino offensive... Continue»
Posted by tankengine123 5 days ago  |  Categories: First Time, Shemales, Taboo  |  
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An Interesting Friend CoCo

Hot CoCo!

Along the way I’ve had the pleasure of knowing 2 pretty nice ‘girlfriends’; one white and CoCo…hot and black. Casual, raunchy, sexy, free-spirited and just fun to be with.

CoCo was a marvel, a wonder of hormone therapy, with ‘her’ everything had gone perfect. She was about 5’ 8 “ with breasts that were well proportioned, not too big or too small, a great ass and killer legs. She was a little overweight, I’d just say a little ‘fleshy’, mildly attractive and oozed a physical glow of well being…along with a satirical sense of humor.

We met at one of those places that tried... Continue»
Posted by swat412 6 days ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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CaughtWith MyPants Down


When they walked in the unlocked door, I froze like a deer caught in headlights. Although Carol was my girlfriend and we had great sex, I still enjoyed my closet dressing. Well one afternoon when no one was around, I took a bubble bath and pampered myself. Then I dressed entirely in Carol’s lingerie and sexiest short skirt. I was feeling sexy when in through the unlocked front door, Carol and her s****r walked in, I couldn’t say or move a muscle. Carol and her s****r just casually walked around me and looked me up and down. I was totally surprised when her s****r took my... Continue»
Posted by dlishmis 6 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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Drink or Dare

crossdressing – threeway – first time – oral – anal – strap on

Ever since I was a c***d I had always fantasized about being a girl. Every chance I got I would sneak into my moms closet and try on her panties, slips, nylons and dresses. The feel of the sheer silks and nylons against my skin would drive me crazy. When I hit puberty and discovered the joys of masturbation these two activities seemed to combine perfectly. So much so that while jacking off dressed as a girl I would fantasize about being sexually used by men. Eventually I felt I needed a real life person to place my desire... Continue»
Posted by naughty_bi_interest 6 days ago  |  Categories: Anal, First Time, Shemales  |  
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Jamie's Descent Part 3

Jami’s Descent Part 3


The limousine took me to Harley Street, home of the UK's private health
industry, for the medical Vanessa had mentioned. To me it had seemed
less of a medical and more of a preparation for something. There were a
lot of the usual bl**d pressure tests and urine samples, but there had
also been a lot of measurements taken, especially around my upper body.
The doctor and nurses were efficient though and seemed satisfied with my
overall condition.

I felt the doctor spent a little too long on what he had said was a
prostate check. The doctor's finger seemed to ... Continue»
Posted by nikkiesilk 6 days ago  |  Categories: Shemales  |  
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The Wild Isabella

This is about the woman of my dreams. That I long for. That I crave. So let me tell you about a moment of madness I will never forget.

Her name was Isabella and she looked nothing like the posts on the forum. I'd heard reports that she was over 6ft, that she was fat, that she was not for the inexperienced.

It took an age to find her apartment and when I got there she poked her head coyly round the door. She was slim and Spanish, with blonde hair and big, blue, mischievous eyes. Perky tits and an hourglass shape - she sure was fuckable; although we I never got the chance, as she was the... Continue»
Posted by waraxe13 7 days ago  |  Categories: Fetish, Shemales  |  
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Enslaved



As I stepped into the department store, I had to resist the
natural urge to turn left and head for the electronics section.
Instead, I turned right, penetrating deep into the mysterious
world of women's apparel. Feeling conspicuous, I tried to look as
if I belonged, relieved that there were no crowds so early in the
day. This was the third time I had attempted this, and I was
determined not to chicken out again.
I knew what I wanted, but not where to find it - and I was
far too nervous to ask for help. Of course, it ended up being in
the last place I looked. Wandering anxiou... Continue»
Posted by klammer 7 days ago  |  Categories: BDSM, Fetish, Shemales  |  
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Maybe


As I stepped into the department store, I had to resist the
natural urge to turn left and head for the electronics section.
Instead, I turned right, penetrating deep into the mysterious
world of women's apparel. Feeling conspicuous, I tried to look as
if I belonged, relieved that there were no crowds so early in the
day. This was the third time I had attempted this, and I was
determined not to chicken out again.
I knew what I wanted, but not where to find it - and I was
far too nervous to ask for help. Of course, it ended up being in
the last place I looked. Wandering anxiously... Continue»
Posted by klammer 7 days ago  |  Categories: BDSM, Gay Male, Shemales  |  
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BEA 2016

first time – anal – oral – shemale – dominant shemale – submissive male – rimjob

Book Expo America. Here we go, again. Will it be the same thing again?

Fly in, get the baggage, take a smelly cab to the hotel. Meet my Sales Director, Victoria (who goes by V), in the bar.

"We've got to set up the booth, Jack. But first, let's have a drink or two!" She winked. V has been my boss for five years. She rode the team hard for sales numbers, but she was fair. We had up years and down years, she knew there was only so much that was in our control. I was her go-to guy. It always felt good... Continue»
Posted by naughty_bi_interest 10 days ago  |  Categories: Anal, First Time, Shemales  |  
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Bikini Boy

boy in panties – bisexual threesomes - bisexual lust – s****rs' panties – boy on boy sexfest – crossdressing pleasure – luscious girl on girl sex – secret lingerie stash

I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage. Then came the divorce. The fights, the yelling & screaming about the "other woman" resounded through the house & the k**s tr... Continue»
Posted by naughty_bi_interest 10 days ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Our Trip to Vegas

Tim & I flew to Vegas to meet with a client to sigh some contracts. We met with the client, signed the contracts and were going to spend the rest of the time doing some gambling and seeing the sights. We were in the bar at one of the casinos having a drink when a gentleman came over to us and said you’re Shauna Riley, aren’t you? We had never seen the man before but I answered yes I am and asked how he knew me. He smiled and said he had seen my pictures & chatted with me on Xhamster. This brought a smile to Tim’s face. We invited him to sit with us. After talking for about a half hour he asked... Continue»
Posted by shaunariley 10 days ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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MY PORN SHOP CONFESSIONS

AZNSWAG

if you read my blog on my profile , you can see my background into how i got into the porn shop business..
i thought it might be fun to share some of my personal stories: things that i have seen & done while working at the many different porn stores across my city. this is one of my many experiences that i will never forget


ill just name it.. my porn shop confessionals =)

i worked at this particular porn store from 2006 - 2010. usually porn stores are very hidden. usually they are in some abstract location where privacy is held to its highest... Continue»
Posted by AZNSWAG 10 days ago  |  Categories: Shemales  |  
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Transformed Into A Shemale

crossdresser – leather – virgin – shemale – lingerie – thrusts deeply – clad cock – tight denim

I was 18 when I first had sex with a man. This is the story....

I am a very hot looking guy. I say that knowing that some may consider me vain, or arrogant, but over the years I have had so many women and men tell me how fine I am, that I know it is true. I am 35, blond and blue eyed, 6'1," 180lbs, with a tan athletic body and a 7" beautiful cock. I have been dressing up as a sexy girl ever since I was 18 years old and had my first experience with a man. The following is how it all star... Continue»
Posted by naughty_bi_interest 10 days ago  |  Categories: Anal, Fetish, Shemales  |  
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