Shemales Porn Stories
Page 15

Dad trains me to be his wife


After a long and unstable marrage of 20 years, the divorce papers finally came. My wife and I only had one c***d, William, and he is very gay. My wife was too much of a homophobic bitch to support him. Even when he was younger we knew he would turn out gay. Always wanting to wear girl's clothing, dress differently, speak differently, even walk differently. I always supported him as a dad and as his friend. I never understood and I still don't understand my wife and how she could just leave her only c***d and I. I remember it was his 18th birthday, about five months ago. She came home from wo... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 3161  |  
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How I became a sissy

So it all started from answering a random craigslist posting that didn't even have a picture. I was off work and horny so I was cruising the ads and I came across a Cross dressing married dom and his wife looking for a sub. I was no stranger to the lifestyle and it intrigued me so I began to write an email. We exchanged back and forth for several weeks and then began talking on the phone. The day had come and they invited me over. I was nervous. I am a married guy. My wife knows all about my past experiences but had no knowledge of this relationship. I got my things together and put them in a ... Continue»
Posted by tg2027 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3159  |  
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A Little Twist at My Last Massage ...... By BigSof

I have a really bad back from an auto injury several years ago and have been getting massages to relieve some of the discomfort I have. The problem with that is I, like so many people with injuries, have an addiction. I’m not talking about pain killers… I am now addicted to massages! Now I know some of you are laughing thinking I am trying to 'be cute', but I am telling you, I could get a massage right now and 1 hour later if given the chance I’d do it again, and again, etc. The overall feeling of serenity and calmness you feel is my addiction. Of course any time you get a ... Continue»
Posted by bigsoftee 2 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3162  |  
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mom made me her sissy

"Mom! I called out as I got home from baseball practice, "I'm home!"

"Hello Danny, we have to talk," she responded, while exiting my room.

When I saw what was in her hands, I became nervous. Some of the guys I pal around with talked me into shoplifting a few things from a department store.

"Please explain where these items came from."

I should have told her I was sorry, and that it was just the one time,

But instead I said, "Tommy made me do it. He said it was a dare. I didn't want him to think I was a sissy."

The next thing I knew, I was in big, big trouble with Mom. I got ... Continue»
Posted by momandboys 1 year ago  |  Categories: Fetish, Mature, Shemales  |  Views: 3159  |  
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Allison the pool slut part 1

Allison had now had her fair share of whore experience. The teen boyslut had fallen in love with big cocks, anal creampies, facials, swallowing, and the rest of the nasty fun she had while becoming a sissy whore for her black neighbor and his dark dicked friends. Little did she know she was going to get the fucking of her life soon…


One day Allison arrived home to find a package on her door. It was addressed to Mark(her boy name) and did not have a return address just a note. The note read “Allison, I took the liberty of buying you some nasty whore clothes for when I return home in a coup... Continue»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3152  |  
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hotel steam room

Once I got to high school my thoughts of wearing panties and sucking cock subsided as I became a normal teen with a girlfriend,It wasn't till I was 22 that I would realise my true passion.I traveled to Toronto with my b*****r and his girlfriend so she could right an exam.We were on a budget so we all shared a room downtown.The first evening I was tired so they went for dinner while I stayed in.While getting a beer from the fridge I noticed her suitcase open and a bra laying on top.I immediately got hard as I looked at it and had memories of my younger days wearing Lingerie.I locked the door so... Continue»
Posted by sluttysherri 11 months ago  |  Categories: Gay Male, Shemales  |  Views: 3148  |  
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How i became a sissy/my first blowjob

I'm a 17 year old sissy now but i started crossdressing 4 years ago when i was 13 :).This is the story. One day my parents went to our lake house for the weekend with my s****r but i was feeling sick so they left me with my grandparents. They were taking care of me for a day or two and i got better so they left and i was home alone.I had 5 more days until my parents were back.One day i was feeling very bored so i opened my s****rs closet and looked at her stuff. I noticed thongs,i never knew she wore them (she was 17 back then). I wondered how they would feel so i put them on. I never felt sex... Continue»
Posted by sissygirl1988 12 months ago  |  Categories: Fetish, Shemales  |  Views: 3148  |  
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Got Caught

2 weeks ago i found myself alone as the wife had taken the k**s away for the weekend i felt the need to play. I went to work and finished early and raced home feeling very naughty indeed. I got in and ran a bath and had a nice long soak indeed and thought about what i would do and where i might get some fun at such short notice?

I got out my gear and put on a black basque with fake 40c inserts, lacy see thru black panties, black lacy top stockings, black strappy heels, skirt, top. I put on my wig and did the make up as best i could being a novice and looked into the mirror and got extremly... Continue»
Posted by abicd 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3146  |  
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my first gay fuck

I've slways crossdressed, from when I was 12 years old. I started by wearing my Mum's knickers and bra, tights, knee high boots and a dress or skirt and top. it felt fantastic wlaking around on high heels, in the back garden, knowing that all the neighbours had to do was look over the fence and see me all dressed up! My cock got so hard and I'd wank myself dry!
I carried on all through my teenage years, using girlfriends underwear. At the swimming pool, where I used to work, I'd have a shower wearing the girls high cut swimming cossies! The feel of the wet lucra around my ass and cock was rea... Continue»
Posted by Nikki_xd 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3127  |  
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Double Stuffed oreo

Met these two dark rich ebony beauties in this roof top bar, sweet and petite they were. Brown Sugar is what they called themselves. Brown has these baseball size titties with hard nipples. She stands at 5'9 with 3" heels, some of the fullest softest lips I have seen. Six pack, bun of steel WOW she can put a hurt-in on me. Sugar has long wavy hair mid of her back, eyes any man can get lost in. No tits just very large nipples,the kind to chew on. Thighs and cafes I would love to sink my teeth into. And some of the most sexiest feet and toes. These girls had something special going on.

We tal... Continue»
Posted by Gehld 1 month ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 3116  |  
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My first BBC fuck!

I went clubbing last week with my girlfriends that I work with and they recommended a hip hop club in a seedy part of town. I was alittle scared but we went anyway and well, and we were really having some fun there!!! I decided to dress like a real lil slut this night, a black minidress, lacey thigh highs and garters and black fuck-me pumps.

My girlfriends hooked up with some cute black guys and took off leaving me there kinda by myself. I was being hit on constantly by these hot black guys but I wanted a white guy, or at leas... Continue»
Posted by sataori_fukame 1 year ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 3111  |  
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I final found him and his friends

For the last 7 years or so I have been from one guy or girl to another looking for someone that I could serve sexually and not interfere with the rest of my life.

Last month I finally found him. I was at the local porn shop on Friday night cruising the theater and the peeps as usual. I was in the Theater by myself in the back row when a guy walked in he looked to be about 35-40 average build dressed in blue jeans and black shirt. He sat down across the aisle from me on the back row out of site from everyone coming in and out of the 2 doors. I sat there for awhile then decided to move ba... Continue»
Posted by tim_likes 8 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3111  |  
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3 weeks in Thailand

6 weeks ago I went to Thailand – Koh Samui for a 3-week holiday just to get out of the system.

I was on my own, in my 50s, divorced and mainly hetro but enjoyed a passing gay experience with “Jon” from a now closed down massage parlor in Manchester UK (told that story a few months ago). So went to Thailand - thank god for Viagra – to fuck a few hookers, get d***k and have a nice break. The bars at Chewang Beach were crowded and “factory like” , full of tit and sweat and I didn't like them. The girls were “well worn” and “routine” if you get my meaning – “me make you fucky fucky long time” ... Continue»
Posted by jimtheman699 7 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3112  |  
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Stacy

I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, neither one of us ever made a move.

My tale begins during the heart of beach season. It was a beautiful sunny day. I had suggested to Stacy that we take a trip to the beach and enjoy some sun and sea. But Stacy told me she didn’t own a bathing suit. The perfect excuse for shopping. I could have k... Continue»
Posted by LadyShi 3 years ago  |  Categories: Shemales, Taboo  |  Views: 3103  |  
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He has made me the town slut

We live in a very very small town, and now I am the town slut. This is the story of how my obsession with one mans cock turned me into the town slut.
I had been sneaking over to see Phillip every chance I could after he had fucked me and let me suck him. I couldn't get enough of his cock. I tried to see him at least once a week. I would usually blow him, but sometimes he would have the time to fuck me good and hard. I get off work hours before my wife and Phillips wife works later so this gives me time after work to dress up and head over to their house for some sissy fun.
One part... Continue»
Posted by firstknightd 1 year ago  |  Categories: Group Sex, Shemales  |  Views: 3103  |  
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I finally take the plunge

I finally take the plunge - a crossdressing story

I'd been crossdressing for a few months at this point but I'd never gone outside while dressed in women's clothing. I'd been to the shops once, wearing one of my outfits under my normal male clothes; that's the closest I've ever been but even that gave me an intense thrill. Even under a fairly loose coat, I'm sure people could make out the outline of my breast forms. Since that little trip to the shops had got me so aroused, I was determined to do it properly next time so I decided that the following Friday I would go clubbing ... Continue»
Posted by CDer 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3099  |  
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University Fun

I was 18 and had was in my first year at University.
I had chosen to go into a hall and to my surprise found I was sharing a room.

My room mate was called Pete. He was a bit taller than me well muscled and very butch. We got on well and had lots in common. We both did alright with the girls and were both enjoying being away from home,

The only thing I missed was being able to slip into some panties and stockings or tights for a nice wank and to fantasise. I had being slipping into my mums panties for 7 years and occasionally stealing my friends mums or s****rs. I had not plucked up cour... Continue»
Posted by webbyhose 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3099  |  
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long saturday at the arcade

what you are about to read is a true and accurate accounting of a day I spent in a video arcade booth

its early Saturday afternoon, and i'm sitting here in an arcade video booth dressed only in sexy little bikini panties, training bra (for my little a cup puberecent like titties) and a white silky like full slip, I have left the door slightly ajar while I rub my little sissy clitty, which is confined in a tight fitting chasity devise, and tucked back between my legs, while watching a really hot gang bang video, hoping for some action. when I happen to glance up at the door, I see your eye p... Continue»
Posted by robinlikesitrough 2 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3098  |  
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little bitch




To tell you a bit about myself and my life, it is just me and my dad that live together
as my bitch of a mother left us to start a new life with my dads b*****r, my uncle.
I am a 12 years old boy, but i'm not like most young boys from as early as the age of 5
i have always wondered what it would be like to be a girl. So from when i was around 10
i would try on my mothers clothes and after a while of doing this i decided to take a pair
of knickers and bra they wasn't too sexy but they made me feel sexy i could only take them
ones as im sure my mother would of noticed if i had taken ... Continue»
Posted by vince01 1 year ago  |  Categories: Shemales  |  Views: 3095  |  
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car sex

it start with my ex wife calling me to watch my k** for a few days while she and husband number 2 went away for a few days..now she and i were still very tight. we had been divorced for 2 years but still friends...so i had no problem packing a few things and going over to watch my k**....i sent her off to school and then hop into my car to go to the store..it was a chilly day out and as i came out of the store a young black girl came up to me asking if i needed a date. I looked around to see if this was a sting or a setup as this was not the right area for her to be looking for a date...as far... Continue»
Posted by dragoniis 6 months ago  |  Categories: Hardcore, Shemales  |  Views: 3090  |  
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