Shemales Porn Stories
Page 80

Duty Bound- part 2

The red stilettos, though new, were surprisingly comfortable as Hannah stepped out into the warm evening air; her cock bulged with excitement under her tight leather pencil skirt, her black silk top with chiffon sleeves capturing her sweet feminine shape perfectly. She met Simone and Babs at a bar close to Transcendence; the other two equally sexily dressed. They had a few drinks and then walked the short distance to the new venue.

Inside, the girls were not disappointed with the new club; it was all tastefully appointed and the music and lighting were soft. It had the feel of a gentlem... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 414  |  
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Click, click, click....

Click, click, click…the sound of high heels contacting a hard surface has always attracted and aroused me. Whether it’s on tile floors in a hallway, the concrete of a parking ramp or the asphalt of a mall lot, I turn in anticipation to drink in some pleasing eye candy. How short will the skirt be, how long the legs and what manner of hosiery will adorn the object of my desire? Sometimes you can anticipate the leg length by the quickness of the steps, short light steps equal a petite form, slightly slower, paced steps announce a graceful flowing creature.
Click, click, click…today it was an ex... Continue»
Posted by MichelleFaye 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 976  |  
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Sandy comes to visit me

If you have read any of my prior stories, you know that while I was born as a boy, I more closely resembled my mother and my older s****rs. I was the only boy in our f****y, and from a young age realized that I was destined to live as a girl. It started early in life, with me sneaking into my s****r’s rooms and admiring their pretty things. Later on, I actually began “borrowing” things from each of my s****rs. I lived in secret, ashamed that I was different.

When I graduated from high school, I moved to the big city to attend the University. I was fortunate, as my grandmother loved me dearl... Continue»
Posted by Rickicd 2 years ago  |  Categories: Shemales  |  Views: 1737  |  
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Ladyboy Secrets

LADYBOY DIARY
by utubeslut

forgive the misspellings but inocent words get sensored
by the auto censeless

Diaries can be dangerous and have unexpected
consequences if they fall into the wrong hands.
Or the right hands ….


Early Spring and that meant a visit from my
Aunt Becky and my cousin Susie.
I loved Susie but she was kinda weird.
She had mood swings like she had permanent
PMS, very unpredictable.
Otherwise she was very sweet.
Crazy bitch.

The neighborhood girls were drawn to Susie
like a magnet. Crazy peop
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: Lesbian Sex, Shemales, Voyeur  |  Views: 1208  |  
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my uncle

The other day I was dressing up in my s****rs tight little black dress, I know I'm passable bit I had no idea how much... Well anyway I always heard I would look like my s****r if I had a dress on and believe me I did. So on this day I had some free time, or so I thought... I spent the day procurring my s****rs things and a few of my mom's.. see my mom doesn't have hair these days in her old age, and she is some what of a wig addict... So she has a great collection, my slightly older s****r helps her buy all of them so they are "hip styles" in moms words.. but I did my hair and makeup the sam... Continue»
Posted by 612Goo612 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3013  |  
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The Intimate Dinner Party

Susan and I were filled with anticipation as we arrived at Victoria’s house. We had been invited to what the written invite referred to as a “Sexy and Intimate Dinner Party”.

Victoria was renowned for her unusual, and always different, dinner and cocktail parties. She certainly did not like doing things the way other people did them. You never knew what to expect, but you always enjoyed them and could say that you’d had a new and exciting experience.

My wife, Susan, was looking incredible. She had a short black skirt that really set-off our beautiful long legs encased in sheer black sto... Continue»
Posted by didi_galtier 2 years ago  |  Categories: Group Sex, Shemales  |  Views: 1808  |  
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Training Sissygirl- part 2

Jim Grinned like the devil; he paid the cabbie and pulled Sissygirl toward the bar. As they went through she felt like a slave on parade; the mainly gay clientele were dissected by many transvestites and the odd pretty t-girl like her. Her cock rose and her bottom tingled as she felt eyes all over her; the feeling of being owned and controlled by someone else appealed to her erotic submissive nature and this exposure was certainly a thrill she had not expected.
Jim led her to a group of males who all introduced themselves as being ‘bi’; they all smiled wickedly at her and eyed her up and do... Continue»
Posted by midsummerman 2 years ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 329  |  
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HERMAPHRODITE GANG BANG PARK

INTERSEX GANG BANG

THIS STORY IS 80% TRUE.
I DID NOT CHANGE VERY MUCH OF IT


I'm intersex. The medical term used to be “Hermaphrodite.”
They even distinguished a “True Hermaphrodite” from
“Pseudo Hermaphrodite.”
A “True Hermaphrodite has an “Ovatestes,” a gland that's not
a testicle or an ovary but both. Yet neither.
Hermaphrodite is a stupid old term.

When I was..um.. young I 5was gorgeous.
B cup tits, perfect girlish figure, hips, ass, pretty face,
drop dead legs, everything.

My older br0ther turned me into a prostitute and used his
connection with our f@mily doctor
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 2280  |  
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Training Sissygirl - Part One

As Sissygirl strolled past Olmos Park in the heat of the day, a tingle ran down her spine as she thought of what may be to come in a few short hours. Her new Boyfriend Jim would be arriving at San Antonio International at any moment; Sissygirl was a little in awe of him as he liked her to be ‘just so’ and had so far been very domineering with her. Though her submissive nature accepted this, as being controlled fuelled her imagination and her arousal, she was also a little scared of how far he might go, she had not known him that long, and though she craved being intimate with him, this wou... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 528  |  
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Duty Bound Part 1

Ever since c***dhood it had been that way; delicate in the extreme and a want of soft bright things. School had proved to be difficult; not being like the others. A fondness for the stricter teachers irked the boys; patently apparent differences alienated the girls. The developmental teenage years were no easier, though liberally minded parents allowed chosen apparel to be worn at weekends, making the desired route in life that little easier. The tortuous journey through to adulthood now accomplished, and independence achieved, indulgence in a preferred lifestyle beckoned.

Hannah glanced a... Continue»
Posted by midsummerman 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 567  |  
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Crissie Fucks the Neighbor

It was a Saturday afternoon and I was all alone in the apartment as my roommate Kelly had gone home to visit her
mother for the weekend. I hadn't had a date or been more importantly been laid in several weeks. Needless to say I was very horny.
I quickly flipped through the TV channels and as usual there was nothing worthwhile to watch so I clicked the off button.
I'd already read the days newspaper and even completed the crossword puzzle.
The weather was fairly warm so I was dressed in tight cut off jean shorts and a snug fitting ladies t shirt. Underneath i was wearing
a skimpy leopard ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Mature, Shemales  |  Views: 2664  |  
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MY FIRST BLOWJOB

I met a shemale online called melisa and we had been talking over msn for afew days, mainly having saucy chats about sex and getting off. She asked me to meet her on the coming weekend which excited me as i was a virgin to cock.

We arranged to meet in a bar that was a stone's throw away from my flat, As i entered the bar it was pretty dark and i waited for my eyes to ajust to the dim lighting, then i noticed her sat at the bar wearing a skin tight, dark red dress that was knee high, she looked amazing. I walked over to her and straight away i was struck by a beautiful smile as she turned t... Continue»
Posted by handyman1991 2 years ago  |  Categories: First Time, Shemales  |  Views: 1515  |  
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Chrissie's New Client

I run a small investment consulting firm. Very small, actually it's just me. It's really just a cover business for what I really do which is to service my male clients clandestinely.
There are an average 20-25 active clients. They are all successful proper business man, many of them you would classify as professionals.
They are all referrals and have been carefully screened. Most of the men are straight but just like a girl with "something extra"occasionally. There are also some who I suspect are Bi-sexual. I don't really cater to the overtly gay community.
That's for no particular reason ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1078  |  
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Meeting A Guy on line part #2

We arrived at his hotel going in his room and just as we got in the door he turned taking me in his arms holding me tight around my waist, mine went around his neck and we stared in each others eyes smiling then I felt his hand sliding down from my waist putting both of them on my cheeks under the back of my skirt.
I didn't say a word at first just stood there letting him fondling them squeezing each lobe tight "dam you have a round soft ass" he said I just smiled more putting my lips to his and we embraced in a long wet kiss using lots of tongue.
I could feel his cock starting to get ha... Continue»
Posted by MonicaBond 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 1037  |  
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Meeting a guy from online part #1

I had been talking to a guy Jim online for a few months he was white 47 and we got into some very erotic conversations on line and even had phone sex together a few time then we decided to meet,I was all too excited thinking about seeing him in anticipating what both of us knew what was going to happen.
I got into town showered getting cleaned up putting on a short brown skirt with a white top over my very little panties and padded bra finishing my outfit with a pair of three inch black pumps, looking at myself in the mirror I thought I looked cute thinking he was going to like what he sees... Continue»
Posted by MonicaBond 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 836  |  
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HERMAPHRODITE BLACKMAIL

I remember it as though it were yesterday.
19 years old, jut dropped out of college over a sex scandal
with my History professor.
I managed to find a good job in a high end boutique
because I was beautiful, sexy and could pass myself off
as classy, even though I was a cheap whore.
My boss was a perverted dominatrix and immediately
made me her plaything as a condition for my employment.
As long as I obeyed her and serviced her clients.
I was making very good money as a prostitute for rich perverts.
I found a fairly nice apartment, no penthouse for sure
but far from a dump.
I del
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1508  |  
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It started w/the neighbors wife then her husband.

About 5 yrs. ago on new years I was invited over by the neighbors to party, they had some friends over; we were getting plastered and eating food celebrating the New Year. When out of the blue in front of her husband and friends the wife starts kissing me, I gently pushed her away not knowing how the hubby would react, much to my surprise, his reaction was almost as if he didn't mind to the point where it looked like he was turned on by it.
That night after everyone had gone, the husband had been long passed out, we went to my house next door, & I ended up fucking her. I remember her saying h... Continue»
Posted by MyaTranny 2 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 6424  |  
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double date fun

It was just normal saturday when the phone rang.I answered it an my mom was on other end.She said can I ask you to do favor for me? I depends on what it is.Well she said, you know Cathy (moms lez lover) she called me and ask me to go out on date tonite.I yea so go, she said want to but her son just moved back in with her.I said yea don't he know about you two?Yes he does but we were wondering if you go out with him with us.I said well let me think,she said he very tall handsome an 46 yrs old.I said but does he know I am fulltime crossdresser? Mom paused a minute and said yes he does.I said ok... Continue»
Posted by cdpaula 2 years ago  |  Categories: Mature, Shemales, Taboo  |  Views: 2004  |  
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The Making of a Sissy - Part Twelve

Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as she pulled her indoors.

“Well, you’ve certainly impressed Mr Roberts, and it’s nice to see you with your clothes on again. We are quite the little harlot now aren’t we? We’ll soon have you back down to earth; I’ve lots of chores for you!” Now it was sandy who was downhearted as she drove away fro... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 770  |  
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Encounter In The Park

It was near the end of my junior year in high school and my parents ere in the midst of their big divorce drama so I was spending most of my time at my best friend Kelly's. It was just Kelly and her Mother because her dad left the picture several years earlier. Kelly’s mom was a great surrogate mother because she knew what I was all about and accepted me with no reservations. Kelly was well on her way to becoming a hardcore lesbian so her mom really enjoyed doing girlie things with me. We used shop for clothes together and she taught me the proper way to apply my make-up and style my hair. ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2798  |  
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