Shemales Porn Stories
Page 17

found the perfect boy to make my wife

After a long and exhaustive search, I have finally found the perfect boy to make my wife.

He is as pretty as any girl I've seen, with unblemished, milky-white flesh, pouty lips, and a round, little bubble-butt that gets me hard whenever I picture bending him over and ramming home my seven-incher. I just know he'll take to my cock like a fish to water.

He is painfully shy to the extent he has difficulties meeting girls his age. He lives alone, rarely dates, and has a mild, submissive temperament. I am positive that once properly trained, he will bring me years of companionship and an inf... Continue»
Posted by lordmax454 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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First time out part 1

It was my first time going to a transgender-friendly bar “en femme”. I was 30 years old and finally had gotten to the point of being extremely passable. I always had a baby face and could pass for a much, much younger person. I had taken the day to prepare myself fully: I had used a mild depilatory cream to remove any and all hair from my neck to my toes. I plucked my eyebrows to create a sexy “bow” to them. I took a bath and cleansed my silky smooth body to make sure I was squeaky clean everywhere. I shaved so close that I could take the slightest, most fragile tissue or fabric and it ... Continue»
Posted by xraydid 5 months ago  |  Categories: Masturbation, Shemales, Taboo  |  
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Sam's Secret Pt2

This story merely has some public groping and some oral in it. Main character is a Femboy. Enjoy

It was nice for a change to wake up in the morning and still be sore from the anal pounding you took the night before. That’s how I felt this morning. Sore, but in a good way. Blaine had truly screwed me good last night. I could still almost feel the way his big cock had been able to invade my second sphincter. He’d had a good 2 inches more than he’d needed for that, which was probably why I was so sore right now. Shit, I was never getting out of bed if I kept thinking of that big thing.
... Continue»
Posted by Wolfshed66 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Sissy's Night In

Summer was approaching and the weather in Ireand tends to be quite irratic. Sunny one minute, rain the next. It gives way to storms which leads to this bried encounter one stormy night.

My home life consisted of two men in the house with me. There was my father; who tended to be distant probably because I was less of the jock a son is expected to be. And there was our lodger James, an old friend of my dad who tended to stay in the home on evenings which for a spell put a damper on my post school crossdressing but after a fortunate encounter with his hard cock I discovered he was quite open ... Continue»
Posted by emmadeevine 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Susan's First Night on the town - out in Publ

Susan had posted she was free on the night of March 22nd and was hoping for better responses than she had received from the two previous attempts to attract a date in the city.

A few days passed with no one seemingly taking an interest when a message arrived - plain and to the point "Could spend the day and evening with You.....dinner out? What time will you get there". Susan was taken aback! "Dinner out?" she thought. That was a very tempting offer, could she feel confident enough to actually go out on the town? She stalled, replying she had to sort out arrival times. "Ok. Do you want me t... Continue»
Posted by sexysusang 5 months ago  |  Categories: First Time, Hardcore, Shemales  |  
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Sissy in the Woods

David was up to something. Since we no longer had the luxery of my empty house to fuck in on weeknights other arrangements had to be made. He caught me one lunch time and told me to arrange a study date with him and his b*****r Peter that night. He told me he'd be picking me up at six and taking me for a drive. He wanted me to be ready with something particularly slutty. I being the ever obedient sissy slut agreed and looked forward to seeing my two favourite cocks again that evening. When I got home I was straight to my room, out of my nasty boy clothes and laid out some possible outfits for ... Continue»
Posted by emmadeevine 5 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Innocent mistake turns into sensual bliss

I was in the shower, and heard the sound of the garage door.
I got this huge devilish smile on my face, because I was going to put on a strip tease for Alex.

We have one of those whole house stereo systems, so I played my "Stripper" playlist, and a song called Pony from an artist known as Genuwine started playing! If you don't know it, look it up.
It's like the national male stripper anthem!
And because I did work as a male entertainer some years ago, I still have most of my old costumes, I put on one of my old tear away numbers, and proceeded to do my best Magic Mike impression...

A... Continue»
Posted by joosyfruit69 5 months ago  |  Categories: Anal, First Time, Shemales  |  
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What i do for my shemale mistress

See, I desperately like being fucked. I love being naked in front of other shemales. I guess I pretend that I'm their woman, and after she's had a hard day out working to buy nice things for me, then the least I can do is lie back and spread my legs for her.

I want to look all nice for her, so I'll shave myself so that I'm completely smooth, legs, armpits, balls and butt crack.

Then I'll want to warm her up. So I get down on my knees in front of her. I pull down her trousers, and let her mighty cock hang out.
I'll kiss her limp cock and thank her for working hard for me. I'll gently b... Continue»
Posted by raviraja00 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Grocery Shopping

Parris Morton walked up to the grocery store while chatting away with some lady from Tenders ‘n’ More who was taking the to-go order. Upon glancing to the left, Parris noticed a decently handsome, dark-skinned man wearing an oversized yellow polo, navy blue fitted baseball cap, and baggy jeans. Parris was somewhat attracted, but the guy was also on the phone. Parris picked up a basket and proceeded cautiously down a natural foods aisle – just to study the thug looking dude.

Luckily for Parris, the man with the sexy swagger of a walk, headed down the same aisle. The look on his face was almo... Continue»
Posted by faggyboi 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Self Confessions of a Gurl Lover

Self,

How I got here started a long time ago. Just for the record, I’m a forty-nine-year-old, twice divorced, father of two, former soldier. I did a tour in Desert Storm, spent some time in Germany, and eventually got out of the Army after twenty years of service to Uncle Sam. My k**s were born in 1990 and 1994, a daughter and then a son. Those k**s, well adults now, are my pride and joy. My second career is as an EKG technician and I really like it. For fun, I play cards, checkers, chess, softball, and a little basketball. I own a nice condo near downtown. Recently, I became a grandfather ... Continue»
Posted by faggyboi 5 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Trouble in class VI

Billie wrapped her robe around me,pulling me tight against her beautiful body. I lowered my head and kissed her firm tits. She inhaled with a hissing sound. I kissed my way to her stiff nipple. Billie held my head in place like a mother would. I began sucking her nipple. As I nibbled and sucked I felt her chest move quicker as her breathing quickened. I felt billies hands move between us and my pants fell. I moaned in anticipation as she slid my underwear down. I looked up into her eyes as she raked her nails over my stiffening dick. Her mouth opened and her tongue ran across my lips. I slid ... Continue»
Posted by Ilikestroking 6 months ago  |  Categories: Mature, Shemales, Taboo  |  
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Trouble in class V

The day finally ended and I headed to billies house. She wasn't there when I arrived so I went to the backyard and waited. As I sat it seemed like it was getting hotter so I stripped down and jumped in the pool. About thirty minutes later I seen her walk in the kitchen. I climbed out and knocked on the glass door. She turned and stared at me for a few seconds then opened the door. She asked what I was doing, I said it was hot while I waited for you,so I went for a swim. I watched her as she looked at my body. She reached over and started running her hand on my chest. I stepped closer to her, ... Continue»
Posted by Ilikestroking 6 months ago  |  Categories: Mature, Shemales, Taboo  |  
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A long overdue night of sissy sex

It seemed like it had been ages,since Kimber(KimberL33)and I had been able to have an evening of unbridled,hot nasty sex.The occasional ,blow and go, is always fun,but we were both in need of a good hot fuck. I had the house to myself for the evening,and my lover was as eager as I to join me.I showered ,shaved and douched,in anticipation of tonight,after getting squeaky clean i slid into a pair of shimmery panty hose and slipped my cock and balls through the hole that all o... Continue»
Posted by jeper11us 6 months ago  |  Categories: Gay Male, Shemales  |  
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Hitchhiker round 2

Hi All - 2 weeks ago I post a story of a hitchhiker I picked up OMG yesterday I received a text message from him (Jerome) saying he could not stop thinking about me and every time he is with his GF he thinks of me and had to see me again.
We made arrangements to meet at a cheep road side motel. He was in the room and as soon as he opened the door for me he grabbed me pulled me close, kisses me i parted my lips feeling his tongue pressing against them. His long tongue slide in and I flicked mine over his. He was moaning and holding me tight.
We broke from our kiss and sat on the bed. He co... Continue»
Posted by MichelleSissy14 6 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Yet More Island Slut, Part 2

Yet More ‘Island Slut…Part 2

When I woke up, the next morning, I was aware of three things; my ass was still a little sore, there was a stiff cock shoved between my cheeks and…I had to pee very bad! I handled the most important thing first then, stopped on the way back to bed to check out my ass in the full length mirror. Walking and sitting had been a little touchy because, my ass looked pretty bad. There were at least four distinct bruises; two at about the middle of each cheek then, two or three more on the lowest part of each cheek – right above my thigh.
I knew, from past experience,... Continue»
Posted by swat412 6 months ago  |  Categories: Anal, BDSM, Shemales  |  
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Valentine's Present

This is purely fictional, sadly.

I moaned softly as I felt her ejaculate into my anus and as I came onto the bedsheets.
I felt her tits squish against my back as she slumped over me. “You’re licking that up” She whispered.
“Fair enough” I said back.
“Happy Valentine’s day hun,” she whispered into my ear after kissing my neck. It was one of the only times she came in me instead making me swallow it or squirting all over my glasses. We lay there for a little, with her on top of me, her tits squished against my back, her soft dick resting against my asshole. The doorbell rang then. I... Continue»
Posted by nightlyfun002 6 months ago  |  Categories: Group Sex, Shemales  |  
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Trouble in class IV

Rubbing my thumb around her crotch Billie started to moan. After a few minutes she sat up and said we need to talk. I was mesmerized by her beautiful tits. Firm,unblemished with pink nipples. She pulled her top up and grabbed her robe. I asked what it was I felt. She said we can never speak about this to anyone. I said I promised not to. Billie took my hand and said she was unhappy as a man, and made the transition from male to female a few years ago and never regretted it. She noticed the bulge in my swim trunks and asked if I liked boys. Shocked by the question, I said NO! I hung my head and... Continue»
Posted by Ilikestroking 6 months ago  |  Categories: Mature, Shemales, Taboo  |  
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You're My Bitch Now Part 8

You’re My Bitch Now

Nikkie Silk

Part Six

Rick had fled from Chris’s room last night after the show and had locked
his door. He heard Chris knocking gently and asking him if he was OK,
but Rick did not answer. His mind was in turmoil. How had he allowed
Chris to talk him into doing what he did. His face burned with shame as
he remembered what he had done. He groaned as he recalled kissing and
licking Chris’s stockings before taking his toes into his mouth. He
covered his face with his hands at the memory of Chris sucking him off
on the webcam. How could he face Chris after this?... Continue»
Posted by nikkiesilk 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Sissy and the Lodger

My father worked a lot and when he was off work he preferred to unwind in his local resting hole rather than stay at home. As a result Ii had a lot of freetime at home. Nothing to be sad about it meant I had a lot of time to explore my burgoning crossdressing within the confines of ny own house. I could walk through every room wearing short skirts showing off my ever growing pantie collection. It made every day dress up day. When I had Peter or David over from next door, it meant even naughtier fun as I would have them regularily fuck me in the ass then I would suck their cocks clean. It was p... Continue»
Posted by emmadeevine 6 months ago  |  Categories: Anal, Shemales  |  
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Trouble in class III

Seeing her smiled gave me some courage, leaving my hand on her ass,I asked if she wanted me to stop. She said no,but be careful you might start something we both know shouldn't happen. The image of her nude body and us having sex was almost unbearable. Snapping out of it I sprayed lotion on her other butt cheek and rubbed. Slipping my fingers under her swimsuit and rubbed. My fingers found the crack of her ass and I slid down. As I reached the bottom she flinched and said I had to stop it.
I went back to clearing out the dead branches from the bushes and tried to get the images out of my min... Continue»
Posted by Ilikestroking 6 months ago  |  Categories: Mature, Shemales, Taboo  |  
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