My Crossdressing Story free porn video

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My Cross-dressing Story

All 100% true.


I was about 13 when I was home alone during the day, I went into my (older) sister’s bedroom and saw her school dress on the floor. For some reason, I thought I would try it on, so I undressed, put it on, and paraded in front of the mirror (no underwear). My immature little penis got stiff, but I had yet to discover the delights of ejaculation.

I walked around upstairs for about 30 minutes, then took it off and put my boy clothes back on.

The next year we moved house, and I started to get an interest in the laundry basket! Every bath time, I would have a look through and discovered my mother’s nylon full slips. I still hadn’t discovered what my right hand was for, so just got stiff which was nice.

It was around this time that one of my (male) friends and I started to ‘play’ - just undressing each other and groping each others cock. One day he suggested I wear one of his mum’s old bras, I did, it was nice! He tried it on as well. We continued to play in this way, then one evening he came to stay over while my folks were away. We looked through my sister’s things (she was away at college), and found a nice blue full slip, and a lovely baby-doll, very sheer and tiny sheer panties. We undressed each other, then he put the slip on, and I put the baby-doll on. As I pulled the panties up, I all of a sudden ejaculated. We both thought this was funny, but didn’t do anything more.

I then discovered girls, and my dressing reduced (but didn’t stop). When I finished college I moved away from home, sharing a flat with a friend from college. I had a good stash of porn, including some tranny mags. On the return from one of my trips home, I walked into a Dorothy Perkins shop. I came out with my first items – a white lacy front fastening bra, matching tie-sided panties, and a long waist slip (floor length). I got back to the flat, and dressed in my own things for the first time – heaven! I can’t remember how many times I came that night, but it was great!

I then bought a house, had much more privacy so my collection increased. Several slips (full and waist), several bra/panty sets, a couple of suspender belts, stockings, a basque, a short nightie and a long nightie (both with negligees). This was way before digital cameras, but I processed my own B&W films, so had a few pics.

Girls came and went, but then I met ‘the one’. We were married just over a year later and I got rid of my collection (and the pics). I stopped dressing – or so I thought. I was travelling around the country a fair bit, and started wandering into stores when away and looking at the lingerie, then bought a few items. I had a small collection that I kept in my car for nights away.

Trips to the US were fun, I would always got to a J C Penney or similar and buy a slip, bra and panties to keep me happy away from home.

Towards the end of this time, digital cameras cam out, and I found I could use mine as a web-cam. I had my first cam 2 cam session, came 4 or 5 times during the night while playing with like-minded others.

The sexual side of the relations hip with my wife was on the wane, so masturbation was my primary relief. She threw out some of the undies I had bought for her (2 white teddies), and also a lovely Kayser full slip. I managed to acquire these before they reached the rubbish and still have them.

There were many changes at work and I ended up home based. I had quite a few conference calls with customers were I was wearing just the Kayser slip!
I gradually added to my collection, and started to dress more and more. My wife retired, and this put a stop to things.

Now, in retirement, I can only wear when she is out for long enough, but I do like to cam with others.

I consider myself straight, and wouldn’t do anything without lingerie (or at least nice man undies), but I do get aroused by a hard cock in lingerie, and I have made quite a few guys cum just by dressing on cam for them. I have no wish to be a ‘gurl’, I’m just a hairy guy that like lingerie (on women as well).

How long will I continue? As long as it still feels good!!!

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Crossdressing Fun

Hi everyone, Vinnie here from bglr . I am 26 and love cross-dressing and being a slutty girl. Been cross-dressing from college .When my senior made me wear his sisters skirt bra and top and he lip-gloss and makeup. I loved it when he got so hard and he sucked my nipples while i rubbed his cock harder. We are alone at his place so he was biting my nipples on the sofa. We bunked college so he could have fun alone early. Once i sucked him before in wash room in local church. He said i looked very...

Gay Male
2 years ago
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Crossdressing Nephew and His UNcle

Once my Uncle and I established a relationship based purely on hot sex while I was dressed as a girl,he would always make plans for us to get together. He soon got his own place,it was on the other side of town and I thought it would be difficult to get together now. One particualr weekend,he called my parents and asked if I could stay over the weekend and help him do some yard work,and my folks said "sure". They didn't think anything of it. Friday night arrives and I pack only lingerie,panties...

Incest
3 years ago
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Crossdressing gangbang

This is not my story. But loved it so much that I was not able to stop myself from sharing with you all.. please do give your response to As I waved goodbye to my wife as she pulled out of our driveway for a weekend business trip a smile began to grow on my face. Anticipating another entire weekend all alone, and thinking of my plans to indulge my deepest fantasies, caused goose bumps to run up and down my arms. Heading back into the house I grabbed a cool glass of water to quench my thirst...

Lesbian
1 year ago
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Crossdressing

Hi back again… This is my friend new story. I met him in London last week .his name was mike. So let start… It all started a few weekends ago when I (mike) had been incredibly horny and my girlfriend was out of town. She wasn’t expected to be back for another two days and I needed some relief. She always wore really sexy panties and I loved the way they felt when she would grind up against my bare cock during foreplay. Being as horny as I was I went to the dirty clothes hamper and found the...

Gay Male
4 years ago
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Crossdressing with my Girlfriend

My girlfriend and I had been dating for several years and our sex life had basically become non-existent. It had been at least a year since we last had sex, and probably another six months before that. The problem was, as much as I loved her, I had developed a different kind of attraction.For some deep-rooted reason, I had grown a craving for ladies' clothing. Lingerie, stockings, high heels; all drove me crazy with lust. Eventually, this led to me dressing and wearing slutty outfits, gaining a...

Love Stories
4 years ago
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The Orchid The Storyteller

This story is an allegory of a real life relationship that developed in my life. It helped me cope with disappointment, and to perhaps be better able to accept the reality that had crashed upon my infatuated fantasy. I cope with the friendship better now, having decided that staying a part of her life is better than nothing, yet there are times when the attraction is still magnetic. I’m sure there are many of you out there who have experienced such a thing and perhaps this will give you a...

2 years ago
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Storyteller

The world is full of history and great stories. From a very young age I sat and listened to them and let my mind show me. As I grew older and my magic made itself known I wrote the stories down. It did not matter what else I had to learn or do, the stories still took me away. I was eighteen when I had enough of other people telling me what to do and when. I thought long and then created a wagon like the travelers. I made a second wagon that carried a tent and lots of cushions and a huge rug....

4 years ago
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crossdresser ashleythis my story

hi my name is ashley,I'm 48,and have been crossdrssing since I was 14.its about the time I discover masturbation.when ever I would take a bath or a shower I would take out of the hamper my sister panties and bra sit the and stroke my cock thru the material.often I'd find a pair of pantyhose,and would slip them on.felt so hot wearing them,I even wore them to school.lot times if no one was home I would sneek down to our shop that we had out back where you could not see it.inside I would strech...

3 years ago
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adult theater short storys

GLORYHOLEI'd love to be in a booth with a woman while she does her thing to all of those unidentified cocks! I have taken my wife to a local porn theater and made her take off her bra and pantyhose. She was wearing a very short skirt so hiking that up was no problem. I had her unbutton her blouse so the guys in the row we were sitting in could see her tits. They would move close to her and in the beginning she would panic but I held her there and told her to settle down and go with the flow....

3 years ago
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collection adult theater short storys

I love going to the local movie theater. my husband and i will go at a time that is not to crowded. normally there are a few couples there. we sit in the middle of the theater and begin kissing ... we get a few lookers. then i will pull up my skirt ( no panties - for easy access) and sit on his dick and ride him up and down. before you know it, we have people watching and wishing. it is amazing how hot that is. some have asked to join, but we tell them no, but are welcome to watch.Me and my...

3 years ago
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Sex storys

(All characters in this story are at least 18 years old) Here are some random sex story's that i had on my computer so enjoy...

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