Incidents In A Cross Dressers Life. Part 3 free porn video

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How I wish I knew more about cross-dressing when I was young and attractive.

I had an Auntie James who cross dressed with his friends but I was way too shy to ask about it. It was not until I was home on leave from the Marines that I had my first experience with dressing. I went to Rocky Horror Picture Show with James and his friends who were all dressed up. Some of them were very hot. We went to a coffee shop where all the Gays go after the bars close. A lot of Gurls where hitting on me. I have to admit I was very hard bodied way back then. I still remember what James told the gurls and some guys…"He's a breeder." I love that phrase!

To back up a bit, early on, well… puberty hit and I discovered that washing the Willie was great fun. I would lock myself in the bathroom on and off 5 or 6 times a day to whack-off. Hell, I would masturbate any time and any place when I thought no one was looking. I then graduated to fingers and anything else I could stick my ass. Mom almost caught me a few times. Maybe she knew but never said. Then in Junior High, I discovered porn. Trading cut-out pics was all the rage. Oh My: Penthouse and Playboy. I found some of my 1970s Centerfolds in an old book I had as a teen. They are still HOT! I was not sure why but I knew what I liked. I still love muff diving! I can breathe thru my ears.

Somehow???? I found a pair of my Moms pantyhose. I was intrigued! At first, I just sniffed the crotch. One day I tried them on and boy was it GREAT. I could have pounded a 10 penny nail threw 2 feet of concrete with my pecker! I came so hard that my face, tits and the wall were dripping with cum. I had to try everything that was femme. Next it was her common white panties. Then I went for the lipstick. God was that hot. I can still taste the first time: PINK.

Then it was getting the legs over my head so I could cum in my mouth. Never did get to where I could suck myself off. Oh to dream! I used to save my cum to use as a lubricant. I never did explore the "width" of my anal probing LOL. I still like the taste of my cum. I will suck the seed right out of its' pussy deposit. Licking it off a pair of tits - pure heaven.

Back to the femme stuff. Then it was the bra. She had big cups but I did not give a fuck. I was too busy polishing the Bishop! Panties, pantyhose and bra at the same time, WOW! I had long hair then and I'm sure IF I would have asked James, he would have given me guidance and plenty of gurls to teach me everything I need to know. I might have even passed (all 6'4"). I had no thought of sex with a guy or gurl. I'm not sure when that developed? My first BJ was when I was sleeping over at James and I woke up with my cock in someone's mouth! It sure beat the shit out of beating-off!!!! I was still homophobic and ask him to stop. Dumb shit me! In hind sight….. It would not be for another year when I went to University and had my first real blowjob from a girl I was dating. I still had a thing for pantyhose and would wear them under my pants. It was then I graduated to a vibrator and vibrating egg. I would insert the egg and go to class. I did not get serious until some years later when a fuck buddy asked me if I had a fantasy. I said dressing as a woman. She then spent the afternoon with me shopping. See other stories and my first pics. I was hooked but no longer pretty!

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Karl to Kayla Cross Your Heart

This is my first attempt at this so, please be kind with your reviews. Email your comments to me at '[email protected]' Karl to Kayla - "Cross Your Heart" By Kayla Eastcock Eatscock My name is, or should I say 'was' Karl Eastman and it all began one evening while I was at work. I am an average looking 26-year-old guy. Short, sandy-brown hair, blue eyes, 5'10", 145lbs. Okay, so I was a little thin, no big deal. Over the past few months, I had developed a bad habit...

2 years ago
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Onec upon a Cross Dresers Life 4

An Incident in a Cross Dresser's Life Part 4I always dressed in pantyhose while teaching class. I had on an extra tight pair of panties to hold in my butt plug. Every movement sent shivers across my nipples. The only person who knew was my fuck buddy and fellow teacher. She was the first to let me explore my cross-dressing (see previous stories). After school, we would go to the park in her van that had dark windows that no one could see in. She would sit back and I would eat her pussy until...

4 years ago
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The Priest Teaches His FlockChapter 10 Sally Rides the Cross

Father John hadn't even said hello to Sally. Pulling her along the corridor again, Sally knowing that they were going back into the basement again. She shuddered when she saw the cross. It was huge, standing over eight feet high, four feet wide, made out of heavy wood. It was a little strange for a cross, it looked like it was upside down, the cross piece lower down the upright, not near the top like a normal cross. At least the altar was gone, but she feared the cross, not sure what it...

4 years ago
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Crossover

Crossover Janet L. Stickney [email protected] There was never any doubt that I was going to be a girl someday. I mean, from early on I would wear pale lipstick and eyeliner with my hair usually braided. Then came the Crossover week and I was able to dress like a girl from the skin out, complete with hips and boobs. My father was a drunk that never cared what I did, and my mom was long gone so how I dressed was never an issue. I work at a small shop that makes and repairs video...

3 years ago
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A Crossdresser8217s Fantasy

Hello everyone, I’m a regular reader of the site and figured that it’s about time that I write a story. Let me first say that the story is completely fictional. Let me first give you a description of myself. I’m really petite and have an average ass. I’m 21 years of age and weigh about 50kg. If my face and chest weren’t visible, one could easily mistake me for a girl of 18-20. I’ve a light brown complexion and a darker ass. And my cock is about 6 and a half inches. Going back a few years, I got...

Gay Male
1 year ago
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CrossDresser Loves being used

I have cross dressed for almost fifty years. It started in the UK when I was eighteen, I had often read the various catalogs for mail order purchases and used to look at the women's lingerie pages where the ladies were wearing garter belts, girdles, panties, stockings etc., and I used to get hard and play with myself and jack off to the pictures.I was always fascinated at my older sister who used to wear stockings, garter belt, etc. and it excited me. One day when nobody was home, I went to my...

Crossdressing
1 year ago
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Cross dresser caught at home by wife and boss

Let me start off by saying that i have been secretly cross dressing for about 8 years now i also go to the local bookstore for an ocasional blow job ( i give and recieve ).I have been wanting to suck and be fucked for quite some time now and it is about to happen. It started when the wife brought home some fine under garments i just had to feel for my self. I was hooked and started a small collection of clothes . I dress up when the wife is away at meetings. Well as i said i was working at home...

Bisexual
4 years ago
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5000 Bet Crossdresser

My friend Cristina and I were just sitting around watching porn. It's something we do for fun now and then. Believe it or not, it has never led to anything. A scene came on where a guy was put in a wig and satin nightgown and fucked by a beautiful blond dominatrix with a strap on. We laughed at what an ugly girl he made and somehow it came up that I had a girlish look to me. She said that I would look much more like a girl in the wig and nightgown than the guy from the movie. I just...

2 years ago
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Bi Cross dresser thats me part 2

A week later Chris and I met to go cloths shopping. We met at a coffee shop in a town a hour drive from me. She greeted me with a warm hug followed by a deep kiss. Our obvious age difference drew some judgmental stares from a lot of the other patrons. Chris sensed the fact that I was uncomfortable. She whispered in my ear "If only they knew all of the cum I licked from your ass". We grabbed two coffees to go and headed out."So Eric said I needed to get something kinky to wear the...

3 years ago
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Fun with a cross dresser

I had a really good experience with a cross dresser yesterday. A mutual friend had recommended him after enjoying his services so I got in touch and he immediately responded by inviting me to go and meet him. It was most enjoyable. I have never been with a CD before but he seemed okay. He is late 50s and very slim. It was really quite strange. He came to the door in a dressing gown and invited me into the lounge where he explained how he had got involved in all of this by dressing up in his...

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