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Christmas Crossdressing

Over the Christmas holiday I was in the gay adult book store and some big old white guy asked me to go to a gloryhole booth. I went in and he went to the other side. I popped in my quarters and as I was unzipping my pants an old floppy dick came through the hole. I just heard “suck it boy.” I licked the head and watched it raise and raise and raise. The more I sucked the fatter it got and I was honestly surprised, he was a good 8 inches. He started pumping his dick through the hole into my...

My journey into crossdressing

The following story is 100% true. Only the names have been changed. About 11 years ago, when I was 28, I met a 40 year old single mum of 2 called Michelle. We met through a mutual friend. The relationship was purely a sexual relationship. I had just broken up with my girlfriend of 3 years, and she had been single for 7 years after splitting with her violent ex. The first day we met, we ended up sl**ping together. As we lay in bed afterwards, we started talking about what we liked and didn’t...

Mom finds son crossdressing

Your mom is away a lot with her friends and she has recently divorced her husband. Right now she's away with her friends to celebrate breaking loose from that bastard and getting back on the market. Your older sister is 26 years old and just bought an apartment a couple of towns over. When moving out she found a bunch of old clothes she didn't want anymore so she left them at home for your mother to send to some charity. Now, you're home alone, your mom isn't coming home tonight since she's...

Caught crossdressing

The below is a true story so naturally names and places changed but the rest of it remains to be one of my memorable moments!!What seems like many years ago now when I finished university my then girlfriend Lexy and I went down to Cornwall to stay in her parents holiday home for the summer while we worked out what to do. To be honest at this point we both know that we aren’t “the one” for each other but I think we both had the same thought, see what happens over the summer and then make...

I was his bitch first time crossdressing

My growing curiosity was really starting to take control. I've spent so many years married, hiding my true thoughts and fantasies about sex.My wife and k**s were going out of town a couple of weeks ago and I was going to explore more of what I wanted. As the day they were going to leave got closer, my pulse would race and my palms would sweat.I just hoped I wouldn't chicken out.Finally, I dropped them off at the airport and as soon as I did, I was freaking out. Just thinking about visiting my...

My journey into crossdressing

The following story is 100% true. Only the names have been changed.About 11 years ago, when I was 28, I met a 40 year old single mum of 2 called Michelle.We met through a mutual friend. The relationship was purely a sexual relationship. I had just broken up with my girlfriend of 3 years, and she had been single for 7 years after splitting with her violent ex.The first day we met, we ended up sleeping together. As we lay in bed afterwards, we started talking about what we liked and didn't like...

Christmas Crossdressing

Over the Christmas holiday I was in the gay adult book store and some big old white guy asked me to go to a gloryhole booth. I went in and he went to the other side. I popped in my quarters and as I was unzipping my pants an old floppy dick came through the hole. I just heard “suck it boy.” I licked the head and watched it raise and raise and raise. The more I sucked the fatter it got and I was honestly surprised, he was a good 8 inches. He started pumping his dick through the hole into my...

caught my son crossdressing

I had come home early from work and found my son, Jamie, sitting at my vanity, putting on make-up. He was wearing one of my cocktail dresses -- and my stockings, my high heeled sandals and, it appeared, my lingerie. He hadn't heard me come in, so I just stood silently in the doorway watching him put on mascara, blush and lipstick. He was completely mesmerized by his own ladylike reflection, completely entranced by the girl in the mirror. He did a very good job with his make-up; clearly he...

My Early Crossdressing

I started cross dressing around 12. At first it was knickers or tights. As I got older I started to get more serious with it. Just after I turned 16, I'd often go out round the streets round town dressed in full girls clothes. I'd always prefer going out late in the evening in winter, as I'd not pass many people and id normally only pass a few cars, some would slow down as I walked along the side of the road.One day I was home alone, my parents were away for the week and my sister was staying...

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 sleep 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...

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...

Friday night crossdressing

Silky long sleeved blouse and skirt? A dress? Or just lounge around in my lingerie. Parking my truck my anticipation only grew to full out excitement, a huge smile was plastered on my scruffy face. I was almost skipping up the sidewalk. I'm sure some of my nosy neighbors saw me but I didn't care. It was a long week to hide Lisa within me. Once inside my apartment, I quickly got undressed from my work clothes and stood in front of the floor length mirror to admire my lingerie I always...

First time Crossdressing

I am a bisexual man, meeting straight, bisexual or gay men for our sexual pleasures. I post messages on various message boards like Squirt and Adam4adam that allow members profiles and posting messages. I also post to local Yahoo groups in my area that allows one to post messages to a small geographical area or to a distant user group. However, the best place to find no-strings attached meeting is on Craigslist where you can post an advertisement for a geographic area in a personal group erotic...

My first time going out as a Cross Dresser

MY FIRST TIME OUT AS A CROSS DRESSER A true storyIt was 14 years ago and I had been married to a beautiful petite woman she had long Cole black shiny hair with green eyes.. We had been married about a year and one night I came out playing around in a pair of her sexy blue panties and a sexy blue Teddy and started rubbing on her and having fun it made her so hot we both had the best sex we ever had in our lives.. The next Friday when I got home there was a bag on the table she told me to open...

How Hockey predisposed me to be a Cross Dresser

I had a thought the other day, my hockey equipment has a number of striking similarities to lingerie!To set the stage, I am a cross dresser. Like most of us, I love everything about ladies undergarments. I like seeing lingerie in stores, on models, on women, on men and of course on me! I love the feel when I am dressed up. I love the taboo of wearing them. I love the thrill of being "underdressed", that is wearing lots of lingerie under your manly clothes, when I go to work. I especially...

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