Cross Dressing free porn video

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It was the early 80's and I was over my friends house who's dad had a ton of porno mags in his laundry hamper in his bathroom. We used to look at it while his mom and dad were at work. We loved the looking at the hot girls but what got me the hottest were the guys who dressed as girls. When we couldn't take it anymore we would jerk each other off but I was the only one willing to give head. At 18 years old these guys would explode down my throat. What really got me off was when I would go home and lube my finger and fuck my ass while jerking off. The explosions were massive.

The images of the cross dressers were in my mind one day as I was at the mall when I was using the men's room. I needed to jerk off so I was looking for one of the stalls to take care of my pressing need. One of the doors was closed but unlocked, and I opened it to find a man in his 30's jerking off. His mane was Gary, he was surprised and first but he noticed me staring at his cock so he ask if I would jerk him off but I said no. I don't know what came over me but I told him if we went somewhere else I would blow him. He said lets go to my car in the parking lot.

I was worried being seen with him so I said I would follow behind him 20 or 30 feet behind him and then when in the parking lot I would get into his car. I followed him behind him and it was all I could do to keep my cock from popping out of my shorts. We got to his car and he told me to take out his cock and suck it but there were too many people around. The parking lot at the mall was relatively full s o finding a quiet spot was hard. Since the man was in his 30's i figured he had to have an apartment or a house so I suggested we go there. Gary mentioned he was married and could not take me home. So I asked if his wife was there and he said she was at work and not due home for a few hours. I said perfect she is not home but he was worried the neighbors would see him bringing home a man to his house when his wife was out.
I thought about it and asked who lived behind him and if the property had trees i could cut through the house behind him and run in through the back door which he would have already open. We drove to the block behind him and it looked like my plan would work so he dropped me off down the block several houses past were I would have to cut through. I gave him a few minutes and proceeded down the block. No one was looking and I ran through the house behind the Gary's house and I could tell no one was looking and I ran right into his house.
We smiled at each other because we both thought we were going to be able to pull off what was on both of our minds and we were eager with anticipation. Gary led me to the back of the house were his bedroom was and I started to take off my clothes. Looking to the one side of his bedroom he had a bathroom and I notice his wife had a dressing table with a make up mirror and her closet full of clothes. Intrigued I walked over to it and started poking around her make up. Devious thoughts welled up in my mind and I looked over and asked if he wanted a blow job or something unique. Gary knew what was on my mind and I told him to give me 15 or so minutes to transform myself.
I am of slight build and have very little hair. I don't need to shave and I have no hair except on my legs and under the arms. Even that is very fine and light colored due to my Nordic heritage. My sisters share a bathroom with me and I saw how they would but on their make up so I was sure I could do it myself as well.
He went to his bed I completely undressed and sat in the make up chair. I put on her wig, started with the cover girl for base, put on rouge, eyeliner, lipstick, a spritz of perfume and slipped into one of her dresses which was on the tight side. Looking further I put on her stockings and was surprised her shoes fit, I'm a mans shoe size 7 1/2. There were white gloves on the table and I put them on as well. I went to her full length mirror and was surprised at how good I looked. To bad I had no tits because I looked good.
Feeling naughty, I walked out of the bathroom and in my best sultry walk I sauntered over to Gary and his looked said it all but his raging hard on said it even more. I spun around a few times so he could see how I looked. I sat in his lap and wiggled my ass. I slid down to the floor and took his cock in my gloved hand and started to jerk him off. The look on his face was full of desire and I thought he was going to bust right there.
I leaned in and took his cock in my mouth and start to suck on his cock and I would here him sigh and his head leaned back but placed his hand on my head to push my head down to deep throat him. His cock was thin but long and I had no problem taking all of his 7". He seemed close so I stopped and pushed him back on the bed and in an act of deep desire I told him to fuck me. He looked perplexed he never had anal sex so I told him to get Vaseline if he had it and bring it back to the bed. I lubed up his got and me ass and laid on my back. I said fuck me like your wife but just enter in a little lower. He lifted my legs up high and slid his cock around trying to get it in. Finally he was successful and Gary was saying "GOD" your so tight and I reached up with my legs and pulled him in with my legs. His cock was thicker then my fingers but it still felt good. The look on Gary's face was priceless as he could not believe how good it felt. He started moving and his pace picked up to where I knew he was going to cum. He lunged in all the way and collapsed on my and i could feels his cock pumping cum into my ass. I keep pushing on him and he was in ecstasy. His cock deflated and it fell out along with most of his cum. While I was laying there i asked for some reciprocation and was only expecting to get jerked off, but to my surprise he took me in his mouth and blew me until I came. He actually swallowed my load and then we laid naked together for a few minutes. We both knew it was time to get dressed and get me cleaned up so i could leave.
That was the first of many times I would visit him he got to the point where he would but clothes for me so he could dress me up only to undress me.












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Cross Country Slut, Part 4I woke up in the darkened room [at least I realized it was a room] my first realization was that I was sore; not only my gaping cunt but up inside. My insides had really been re-arranged. I also realized that, not only did Bill have me firmly in the spoon position – with his cock jammed between my cheeks – but there was another body in the bed. As my mind started to work a little better, things started to cum back to me. I would find out later that, not only had I had...

1 year ago
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Cross Country Slut Part 3

Cross Country Slut, Part 3Once things had returned to normal – whatever the hell that was/is – we just lay there for a while in basic ‘recovery’ mode. I finally stopped shaking like hell all over and could breathe kind of normally following a lot of hugging and kissing. I found myself wondering if there would be a knock at our door; I’d been a little loud. Bill thought it was funny; he was also amazed.Yep, that had been a true multiple orgasm.I was glowing so hard that I was just tingling all...

3 years ago
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Cross Country Slut Part 2

Cross Country Slut, Part 2The next morning I didn’t know where I was at first; I DID know that someone had given me a good sexual workout. My cunt was raw, I had general aches all over and…my insides had been re-arranged. In some ways I’d always found the first and last things, as far back as I could remember, kind of erotic. I’d had a good time. Without disturbing the sleeping Bill; I slipped out of bed and made a bee-line for the bathroom; I really had to pee! The sun was coming up so, I...

2 years ago
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Cross Country Slut Part 1

Cross Country Slut, Part 1It began as just a little on-line chat in one of the old Yahoo chat rooms. It became private and steamy after a while. I asked him to wait for a few minutes, did my hair and a little makeup then, turned on my web cam. For the next few hours we chatted as things became VERY hot. By the time we said ‘good night’ I was sitting on my favorite butt plug, I’d cum twice – my panties were long gone after I’d made a mess in them after a while – my nightie was up around my waist...

4 years ago
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Cross Dressing Pegging and the Promise of a Three

After my last session with Ann, the gorgeous older woman (we’d call her a MILF nowadays) who’d discovered my love for cross-dressing, things were quiet for a couple of weeks. She’d only ask me to visit her when she knew her husband and son would not interrupt which so far meant when they had gone off to watch their football team playing away. It seems that they had a run of home games.Mind you, keen as I was to play with Ann again I did also enjoy replaying our sessions whilst lying on my bed,...

2 years ago
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Cross Dressing play turned horribly wrong fantas

It was just another warm Sunny weekday morning like any other in summer. My wife kissed me goodbye as she left for work, I took my usual pervy glance at her as she wiggled her hot behind out the door, I was setting up in my home office, ready for another day of working from home. I listened to the car roll out the driveway then the gate closed, I started working through the usual emails and meeting requests.. I got bored of work after a couple of hours I decided to go into our bedroom and rifle...

1 year ago
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CrossDressed Fairy Tales Snow White and the 7 Trolls

Sherry and Sadie, two married men, have a girl's night out at a bar. The evening goes badly and, like Sheherazade, who related the 1,101 tales of the Arabian Nights, they end up in great danger, desperately spinning stories to protect their derrieres. For material, they transgender fables they have read, hoping that their captors won't know the original. Will this strategy work? It will depend on you, the reader, because Sherry and Sadie will soon run out of ideas unless you...

1 year ago
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CrossDressed Fairy Tales Rapunzel

Some familiar fables transformed for readers of transgendered tales. In part 1, Sherry and Sadie, two married men on a "girl's night out" visit a lesbian bar and go home with Big Sue and Mike, two women who are dangerously upset to discover that they've been seduced by two cross-dressed males cheating on their wives. Like Sheherazade in the Arabian Nights, Sherry decides that the only way to protect their -- um, posteriors, is to entertain Big Sue with fabulous stories. ...

2 years ago
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Crossdressing the beginning

I would assume that for most men, interest in women’s clothing started at a young age. For me, this occurred when I was 11 looking through the Littlewoods, Gratton and Freeman catalogues that my mother used to have.At the time, I lived with my mother Jane, who was divorced, my brother Anthony and sister Sharon, who were five and three years older than me. It was quite easy to sneak one of the catalogues up to my room and thumb through them. If one of them had bothered to look at the catalogue,...

1 year ago
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Cross Country Vayage For Sex 8211 Part II

We all got ready to look around Liverno City. It was almost noon time. Before we go out, Nila Used my ‘One sim card’ mobile to call her friend along with their parents in a’telecom’call to convince them. We disembarked from the ship but, the weather was not so favorable. We walked through the shopping thorough fare and bought some souvenir and gift items. We walked along the broad walk and shoreline. We had lunch in a restaurant . After the lunch Nila went to the bathroom. I asked Mila,”did you...

3 years ago
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Cross country run

Three of us were on a cross country run on a summer's day when we fell victim to a sudden thunderstorm. The rain came down in sheets and we were thoroughly drenched. We were each wearing white shorts and thin white vest and embarrassingly these were now completely see-through. The rain kept pouring down, and we finally spied a cottage up ahead and decided to seek shelter. My two mates huddled behind me as I knocked the door. I covered my crotch as best I could. The door opened and a vision of...

Wife Lovers
4 years ago
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Cross dressing for my boyfriend

My name is Chris and I’m a 25 year old, white, bisexual male. I stand 5’9″ and weigh 135 pounds with light brown hair and brown eyes. I’ve always had somewhat of a feminine body and I’ve always enjoyed being a “bottom” when with other men. I met my boyfriend Mark about a year ago at a bar. The minute that I saw him, I knew I had to have his cock inside of me. Mark is 27 years old, 6’2″ and weighs 195 lbs with brown hair and a very hot body. He works out a lot and plays some sports. You could...

Lesbian
3 years ago
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CrossDresser Fuels Feminine Passion In Sai Now Sindhu

Hi, My name is Sindhu (using a female name). Here, I am going to write about how I am smitten by my girlfriend’s brother and turned from a straight guy to a dick-loving cross-dresser. My girlfriend and I started living together after both of us got a job in the same city. Both our families knew about this, and they were cool with us. We were happy together; we were enjoying our life to the fullest until her elder brother came to stay with us and took me to a fantasy world which showed me how...

Gay Male

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