Shemales Porn Stories
Page 14

my mom turned me into 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... Continue»
Posted by nicoleinberlin 3 years ago  |  Categories: Fetish, Shemales  |  
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First Time Shemale Surprise

It was pretty late and I was well into my drink. God knows where my pals had gone off too. I was sat in a bar nursing a bottle of beer when this tall, sexy lady sauntered towards me, her black wavy hair bobbing with each step and her dress shimmering purple and gold as the dim light reflected off it.

She rested her hand on my leg and without taking her bold eyes off me said, 'Hi. I'm Jess. Drink?'

I was still fairly lit, but completely taken aback by her directness, I still managed to mutter, 'Sure.'

'Bobby – Two whiskies.'

We clinked glasses and she downed hers in one. Not wa... Continue»
Posted by waraxe13 3 months ago  |  Categories: Shemales  |  
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Kitty's hitchhike

One Friday I went to the local shopping center about 5 miles closer to our home. I did some shopping and had a late lunch at a restaurant. But as soon as I got out, I came to know that some VIP has been murdered and there is a sudden transport strike. A 3 mile walk was no big deal for me if I had to. I started walking and putting my thumbs out hoping for a ride. Soon I was picked up by a guy who was noticeably older, driving a real nice older car. He said he could take me to the intersection near about 1 mile from my home and I would be able to walk home from there. That was fine with me. As h... Continue»
Posted by CumLovingKitty 8 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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Ladyboy Switch Story

I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same men naked however and something changes. I don’t really understand what happens to me.

I guess in simple terms it is this – I am a cock pig. The cock is the most exciting thing in the world for me. I love having it in my mouth. I love having it up my arse. I love seeing and tasting the cum that co... Continue»
Posted by ClassicCockx 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Paybacks Are Hell - The Gangbang

Paybacks a Are Hell
So I get a call from Denise, a friend that I haven't spoken too in about four years. She tells me that she was in town and would like to get together. I tell her that I am meeting my husband for lunch and she was more than welcome to join us.
As I see Denise walk in she looks just as she did when I had last seen her. Denise is 38 years old, she is a petite woman 4'8" about 118lbs, nice sized breast, light milky skin with deep natural red hair, married with one daughter in collage. She was a wealthy stay at home mom, dressed quite modestly and was always very involv... Continue»
Posted by jm6060 2 years ago  |  Categories: Voyeur, Hardcore, Shemales  |  
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couples sexual exploration

So here we are at our hotel room, on vacation for a week in Hawaii. This is our second night and we decided to bar hop. We had fun at the first bar, we stayed for three or four drinks (wife drink faster than i do), we were supposed to stay for one. We decided to hop to the next, this one bar was jumping! And not a line outside so we went in and head to the bar. This one girl started conversation with my wife as we wait for our drinks. She was petite a couple inches shorter then my wife with nice c cups tits, long silky brown hair looked mixed or Latina, pretty but didn’t think much of it. ... Continue»
Posted by welove2sex 2 years ago  |  Categories: First Time, Group Sex, Shemales  |  
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Babysitters Secret part 2

Synopsis: This is the second installment of my series "The Babysitter's Secret." I wish to extend my sincere gratitude to all those who wrote to me to share how much they enjoyed the story. Any time I can make one of my readers cum, I know I've done my job. In the previous episode, a husband and father of two young c***dren named Peter began an illicit affair with the teenage babysitter named Jenny Rove - a pretty young woman who Peter discovered was actually a transsexual. As our story begins, Peter is divided by his desire for Jenny and his devotion to his wife, Shawna.


Two months ... Continue»
Posted by drew1207 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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First Time With A Guy And First Time As A Gurl

worked summers in a factory by my house when I was in college. Nice, clean summer job. Charlie, the Chief Engineer was my boss. He played Div. 2 college football and still was in great shape. Thick arms and legs, big hands, broad shoulders. He was going a little bald, but otherwise...anyway. I wasn't into guys, so I didn't notice those little 'things'...signals, whatever. I had a somewhat steady girlfriend, but she went abroad that summer.
Being 19 I was, it seemed, always thinking about sex. Loved jacking off to the 'Men's Magazine; I found in the guys locker room. I especially found the Fre... Continue»
Posted by keripinkpanty 1 year ago  |  Categories: First Time, Shemales  |  
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Meeting In The Woods

It was about 7.30 in the evening and the sun was going down, but as it was summer it was still quite warm.
I parked my car in the road across from the wood, then clutching my carrier bag I walked down the road a little then crossed over and went into the wood.
The place I liked to go to was about 200 yds into the woods and over by an old wall that surrounded a large section of the Whipps Cross hospital grounds, you wouldn't go over there normally as it went no where, so for privacy it was ideal!
As I walked along I could feel my stockings and suspenders gripping my legs, I could feel the st... Continue»
Posted by annette14 1 year ago  |  Categories: First Time, Masturbation, Shemales  |  
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Baking a loving cake

The following letter I just wrote to a couple seeking horn toad letters about fucking them. When I get inspired I like to write, and for whatever reason this couple did it. OK, well, their sex was the reason!

Dearest Make a Cake,
What a pleasant name! Do you bake love madly? Or love baking up some sex? Either sounds ever so wonderful!

As to the Bears I always have hope for them every year. In case you were wondering the reason I even asked that is because I noticed the slippers you were wearing, and that C is very distinct to a true Bears fan. I suppose I would have more fun ... Continue»
Posted by Tigerpaw46 9 months ago  |  Categories: Anal, Mature, Shemales  |  
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.......Mt Frist Train

My First Train
There are so many sex terms used today it is mind boggling and each term has different meanings to different people. For example, “Gang Bang.” To me it means a women or a transsexual whom of their own free will copulates with three or more men. When a woman or a transsexual services seven or more strangers, she is having a train pulled on her. This is the story of my very first train.
A year after my wife found out I was a male-to-female transgender and I became her cuckold we both had a few new lovers. One of the guys I was fucking pretty regular call me up one evening an... Continue»
Posted by littleoralvee 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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A Halloween Party

I've always loved Halloween. It's the one day out of the year where I am confident to go out fully dressed as a CD. If anyone objects, I just say I'm going to a costume party dressed as a woman. I've seen lots of straight guys do it. . .or, maybe they're not so straight after all. Anyway, I was getting dressed up to go to a party at Doug and Jeannie's house on the waterfront in Mercer Island. The perfect venue for a Halloween party - both Doug and Jeannie were bisexual and very open about it and their parties were always filled with diverse folks from all lifestyles. The vibe at their ho... Continue»
Posted by rikki50 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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my first cock experience (true story crossdressing

I will never forget my first experience with another cock , it was the only time I have ever been with another man, now saying that I do date ts women, I love them as much if not more then I do genetic women. I was 12 years old and like any young boy , very horny . At that time my best friend liam and I would have sl**p overs and do normal k** stuff , sports , video games , camping , never did I think that one day I would have his warm milky cum in my mouth or his warm hard throbbing Dick inside my ass pussy .

It all started when we were looking at a magazine and saw a picture and article ... Continue»
Posted by dickissogood 5 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Daddys little helper 2

I was in shock. I had just watched a video of on my father's computer of my dad and my best friend Sam on the very bed I was sitting on. My friend was dressed in sexy pink lingerie and had sucked my father's dick until he had exploded all over Sammi's (as daddy called her) face. The pair of them had very obviously enjoyed the experience.

That wasn't what had really shocked me though, the shock came from a couple of things. The first was that as my father had unloaded his come all over my best friends face, I had been thinking that it should be my face that was receiving his tribute. The oth... Continue»
Posted by sparkyking 2 years ago  |  Categories: Shemales, Taboo  |  
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Norman and Anastasia

For the first time in my life, my uncle Norman was not pleased to see me. His s****r, my mother, had not heard from him in a little while and was worried so I had been volunteered to drop in on him and make sure that all was well. So here I am stood on his doorstep and he is peering round the door at me, holding the door open as far as he can to make sure that I can't see in but so that he can see me. He wears an annoyed look on his face. I am disturbing him in some way. It is then that all becomes clear. A voice speaks behind him.
"Who is that Norm?"
He turns his head so that he is speakin... Continue»
Posted by dasilva1672 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Picked up in the Park

It was a beautiful sunny day and I decided to take a nice walk in a local park. I wore a loose t-shirt and a pair of gym shorts so that perhaps I could get some sun tan on my freshly shaven bare legs. I walked my dog in this park from time to time and I was aware that it was kind of a cruisy place sometimes although on this particular day the park seemed fairly empty. I walked through some of the trails and it felt like I had the whole park to myself. I was feeling so horny that I almost ducked off into the woods to jack off when I spotted a guy coming towards me on the trail. He was abo... Continue»
Posted by rikki50 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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New Neighbour New Role

It was a hot damn day and my neighbour was out in her balcony with two of her pals, laughing, drinking and enjoying the heat. I'd just moved in next door and our balconies are parallel to each other, no private divider. At eighteen, these were my first moments of independence and I was loving being able to do what I want – a home to freely play with my boypussy. Although at this moment in time all I'd managed to do was unpack a couple of essentials - TV and console.

So yeah, I was checking them out in between haphazardly setting up my den and enjoying myself at the same time - what kind of... Continue»
Posted by waraxe13 3 months ago  |  Categories: Fetish, Shemales  |  
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Turned into a sex slave for Black Men

A few years back I spent time on and off with several
shall we say more dominating types of gentlemen. One of
them, who for this I shall call Leroy, just loved
when we got together to make me totally helpless.
It was our 6th or 7th meeting. Leroy and i had been chatting on Yahoo
and when he found out i was free that weekend he insisted
on coming over later that afternoon.
We talked about when and what he wanted me to be
wearing when he arrived. We settled on 4:00 and I was
to be wearing a red waspie, black fully fashioned nylon stockings,
black bra, short tight black... Continue»
Posted by sissirandi 1 year ago  |  Categories: Anal, Interracial Sex, 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 4 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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Mom Transforms Son into a Transsexual. Part 2

Mae and me were laying in bed cuddling when our Mothers walk in and informed us we had a doctor appointment Mae and I exchanged looks and went into the shower Willa came in the Bathroom and told us to shave each other's body.

We finished as told and dressed each other in our best prissy outfit and walked down stairs we quickly left, jumped into Moms Caddilac we drove for about a half hour then pulled up to a Medical Building. Me and Mae waited in a room while our Moms Talked to a doctor, 90 minutes later a Nurse marched us into The doctors office. The sign read Dr. Goldstien Our mothers w... Continue»
Posted by sissytimmy 2 years ago  |  Categories: Interracial Sex, Shemales, Taboo  |  
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