Shemales Porn Stories
Page 59

Lodger's Surprise 3

Pete walked me upstairs and to my bedroom. He sat me on the bed and kissed me.
He explained that when he interviewed me for my job something about me made him think I might turn out to be a crossdressing sissy and that his former secretary Jenny and her sissy hubbie might be able to find out for him. As he spoke he undressed revealing a hard muscular body that belied his 60 years. He was hairy and there was a large bulge in his tight trunks.
I reached over and stroked the bulge and he smiled and pulled down the trunks. A thick cock shorter than Mikes but much thicker sprang out. Without bei... Continue»
Posted by maninnylons 1 year ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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How I learned of the pleasures of anal sex

This narrative is the journey that lead up to my first experience with anal sex. The details I have here are as accurate as I can recall and any dialog is essentially the best of what I can remember now. It of course gets more sexually explicit and graphic towards the end...

I was born and grew up in what many would probably call an average small suburb. In my early years, while starting puberty I began to explore sex the way I assume many boys across the world did to start. A few times during this period I became curious about girls and what made them so different from boys. One of the obv... Continue»
Posted by UnDressed2Thrill 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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My road to womanhood (so far....)

Quick Disclaimer: I don’t claim to be or think of myself as anything other than a student of humanity and so I claim no stance on my views or words being considered academic or certified for anything relating to gender or my view of the world, simply sharing my experience and hope that I accurately convey what I thought at the time and what I think now. I’ll frequently move between arguments of masculinity/femininity vs male/female gender identity vs biology/genetics (strictly-physical world view) vs sexual attraction, etc so please don’t try to correct me or overanalyze the specific words I u... Continue»
Posted by UnDressed2Thrill 1 year ago  |  Categories: Anal, Shemales  |  
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My First Time With A Boy!

These stories always start out with "the summer after high school" or "my first semester of college" but it doesn't gravitate to the true experience felt when actually going through changes in your life....hormonal changes. So let's just say for the sake of this story, that I was a teen....and he was a teen, and a teen is 13-19 years in age. But none of that matters. What's important is that this time of my life was full of huge changes. Cross-dressing was not new to me at this point, and by now I had well broken into the habit of using my mom's make-up. I mean, every time I looked in th... Continue»
Posted by Ivygurl86 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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My Masterfriend's Games or What Happened to R

It has been a few delicious weeks since I met my "Master" in person, and our relationship has quickly grown into something else. Our first few encounters were pretty straightforward. Not that there is anything straightforward about being on my back with my legs over his shoulders!

It was something else. There has been a concerted effort to know more about me and some of my fantasies too. It's not like they were hidden and all. My profile on "The Site" has a lot of fetishes listed and a few stories written from a personal perspective. I think he was just seeing if he can mesh some of my... Continue»
Posted by LeslieStone 1 year ago  |  Categories: Hardcore, Shemales  |  
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The Sissy a*****ion

You are walking along, you feel a presence, a person quickly comes up behind you and c*********'s you. You pass out but you catch a glimpse of his green army officer hat.


You wake up several hours later chained to a rack naked. Two identical women come out with a cart filled with cosmetics. First they take this special soap that when it touches your skin it makes your skin very sensitive and a sensation of pleasure takes over at the slightest touch, then the two women grab nail polish and paint your toes and the your fingers. Then, they grab a special foundation that they apply to your wh... Continue»
Posted by TheGoods69 1 year ago  |  Categories: BDSM, First Time, Shemales  |  
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rocky my giantess shemale lover

I have been having this wild hot dream of a friend that lives close to me a great tall CD I know on here and have been fantasizing of him getting much taller : I see Rocky walking up the walk my huge breasts are heaving in my tight dress as I rub my big long gurl cock in my tight silk panties ,a knock at the door tells me he is here as I open the door he even with out his heels on is much taller by almost six inches his eyes are wide as he takes in my huge swelling chest that looms just below him my big clit is rock hard by now as I watch my friend get dressed he already has his long legs enca... Continue»
Posted by huge_cock_rules 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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part to rocky busting angels cherry

Mmmmm I can feel it now as Rocky still has my throat full of his gigantic huge cock as he caries me over to the bed his giant form toweres over the bed as he dropes down to his knees and slides his huge cock out of my mouth and lays me on my back on the bed he lays the gigantic long shaft overtop of my body sliding the shaft up over my stomach through my cleavage up till the head is resting on my lips ,im trembling with both fear and anticipation my tiny virgin pussy is spasming waiting for it to happen his giant of a cock the head bigger than a g****fruit is leaking bits of cum from the last ... Continue»
Posted by huge_cock_rules 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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First blowjob (Part 2)

Two days after my chance meeting with my first "Daddy", I called him to set up a time to meet again. I had the name of the motel he wanted to meet at but wanted to make sure we could still get together. He said we could still get together. I was ecstatic!

He asked how much stuff I had to dress up like a gurl for him. I told him I had a wig, makeup and training bra that I stuffed socks to make it look like I had little titties. I also mentioned that I had a little short dress and a large collection of panties. He told me to have it all on by 4:30 but mentioned that I was to wear no pa... Continue»
Posted by KaylaCD15 1 year ago  |  Categories: Gay Male, Shemales  |  
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FUCKED HARD

hi,friends...its really awesome to share my personal experience with you all and in the same feeling i am f***ed to share a new story for all of you.it was friday when i came back to my home suddenly i came to know that my friend George is comming to my home.as u guys know i stay alone...i was very scared that what he will be going to do with me as he warned me not to go outside the house ....bell rang George was d***k and he was in mood to fuck me....He pushed me to the wall held me in my hips and bit and sucked on my thick juicy lips. Inturn, I put my arms around his shoulder and hugged him ... Continue»
Posted by ladyxboy 1 year ago  |  Categories: Hardcore, Shemales  |  
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Nate and his tranny neighbour

My first ever story. Depicting sex between a man and a transsexual.
It is lengthy but personally I enjoy these best. Constructive feedback is greatly appreciated, so feel free to write to me. Enjoy ; )

Nathan (Nate for short) was an average eighteen year old boy; liked girls, sports, partying, and being on his summer holidays he enjoyed the time off school. With some exceptions to the average rule, he loved his kinky dirty thoughts and porn. Frequently watching shemale porn, gorgeous busty women with big tits, a pretty female face but a thick juicy cock to be pleased, not a pussy to be fu... Continue»
Posted by BiTwinkxx 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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One amazing night with a married man

A few years before my dating (and sexual) life was totally relied on online dating (and porn) sites. As a result there were plenty disappointments; either due to fake profiles or due to members who presented themselves as courageous but didn’t dare to proceed on an actual meeting. As I am not that much into online sex (I do like some erotic chat but I totally hate cam sex) I was facing a long dry season.
I was about to give up that form of hooking up. Still there was a guy who was looking interesting. We had chatted several times and his replies were showing someone smart with a sense of humo... Continue»
Posted by georgette32hk 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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First BJ cd/cd

The first time I gave a blow job to another gurl was some years ago, She could only meet after 3 am when she got off work. I took a room with a hot tub in hopes of using it. I laid in some frozen vodka and a few munchies. I did my makeup, shaved everything to perfection. Corset, black stocking, FGPs (black and red toeless}, and I had my pedicurist put fuck me red polish on my nails.

She arrived on time and went into the bath to change. She would have been a very good looking trap with some minor effort. We got into bed and I asked a few necessary questions like are you disease free: Yes, L... Continue»
Posted by williegirle 1 year ago  |  Categories: First Time, Sex Humor, Shemales  |  
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my fantasy part II

I stood in front of my mirror thinking if I wanted to go to the street where the other girls of the night hung around or the local truck stop. I was getting hard thinking of being out that night!! Next thing I know my cock is out of it's tuck and straining against my dress. I need to stroke it so I free it from my dress and start rubbing it!! I'm so addicted to edging I stop stroking right before I blow!! I edge a few more times all the while contemplating where I would go. I decide right before my last edge and I will be going to the truck stop. I hang around my shit hole of an apartment whil... Continue»
Posted by nebraskasissypussy 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Becoming the neighbourhood slut - Part 2

Read Part 1 first :))
http://xhamster.com/user/analhottie/posts/406487.html

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As I was sitting on the floor still covered in Mark's cum, he continued to slap my face with his cock. He kept saying what a good slut I am. Every time he was saying "slut" or "whore" to me I could feel his cock twitching. He was loving it which was turning me on immencely.

He then grabbed my hands and pulled me up. He then lead me to his couch and put me in a doggy position. He then started kissing, slapping, licking and even gently biting my freshly fucked ass. My pleased moans were more than enough of ... Continue»
Posted by analhottie 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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Part 3 - Lisa Comes In

Make sure you read "Back in College with Kelly" and "Meet up with Kelly".

Lisa came in, setting her bag on the dresser and sat on bed next to me while I was trying to hide. Teasingly she said, “Are you naked under here?” while tugging at the top of the covers. I tried to tell her, “No! Stop!” but she quickly exposed me from my refuge. Nervous and embarrassed, I tried to cover myself with my hands and pull the sheet back up. Kelly came over telling me, “Stop, its ok. She knows.” “What do you mean, she knows?” I asked. “I told her about us and that’s why she is here” she said, while trying to... Continue»
Posted by ahsleymills 1 year ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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Nate and his tranny neighbour

Part two of Nate's fun ; )

Again all feedback is greatly appreciated !

It had been three days since Nate's time with Jez. It was 12 in the afternoon and he looked out his window at Jez's garden. There she was idly busying herself in the garden, that gorgeous feminine frame hiding a delicious thick cock. His cock started to harden at the thought of her again, and he was desperate for another time with her. With his parents out for a while he thought maybe he could try a chance going over. He had showered and washed 'all' areas of himself should he be so lucky. He put a tight t-shirt on w... Continue»
Posted by BiTwinkxx 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Christine ad the Neigbor

Hi. My name is Chris, though some know me as Christine. I am John Collins’ mistress. We care deeply for each other. John “keeps” me, he supports me financially and in return it is my pleasure to keep his sex life exciting, as well as to entertain any of his gentleman friends who drop over.

It all began innocently enough, I suppose, when I had just turned eighteen and had moved out from my f****y’s home to be on my own. To support myself, I worked as a landscaper as well as a housepainter. I was able to support myself ok in this way, though it required that I budget.

I rented the upper f... Continue»
Posted by ssup28 1 year ago  |  Categories: Shemales  |  
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Spencer's Surprise

Please note this story is pure fiction, and is just a fantasy

Spencer stood at the big mirror in his parents room. He slowly looked himself over. As he looked at the mirror, he stared at the gorgeous woman infront of him. He had been dressing in his moms clothes for a long time, but for the first time ever, he did his makeup, and it looked sexy. He stared at what he was wearing. A black lace bra, black silk panties with a lace trim, black sheer stockings with a lace trim, and a black garter belt. He finished off his look with the long blonde wig he had found. He knew he forgot some... Continue»
Posted by ZephyrTS 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Lisa Katie Day A little Tgirl Tart In Training.

Lisa A little Tart In Training. (part 01)...

I’m standing at the bedroom dressing table just putting on my red gloss lipstick I see you standing in the door way taking in the view of me in my Mrs Christmas outfit exactly as you see me in the photo's no my page here, Black & red Basque with suspenders, red silk thong Knickers, red stockings ,white frilly ancle socks, and my sexy santa's helper costume with my Red 5" high heels.

You walk up behind me, You startle me as you slap my ass and say you Naughty girl lisa, you've got my cock all hard with that sexy red number that your wearing you... Continue»
Posted by lisa_katie_01 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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