Jim's First Dress free porn video

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Jim's First Dress By Gigi For Jim It started as just another day. He worked downtown at the office, dressed as usual like any typical guy; tie, dark jeans and white shirt. At the end of the day, on his way to the bus stop, he just happened to walk through a big department store. Normally he'd quickly look at the men's wear but today the pastel-coloured summer dresses caught his attention. They were on sale: just $10 apiece. He immediately thought about what it would be like to wear one and suddenly felt a rush, his heart beat faster and he felt a little dizzy. This was puzzling to him. There was one in the XL rack that seemed to be about his size. He was tall but the dress looked like it would reach down to his knees. It was sleeveless, mostly light pink with a cute pattern of little yellow and blue flowers. It had a short V-neck with a pretty white lining. The hemline of the dress was wide and free-flowing. Overall it appeared very loose so he decided he wouldn't need to try it on. In fact he was too timid to even stand in front of a store mirror with it. He had never felt a stronger urge in his life than right now, to own this dress. He thought to myself, "If a store clerk asks, I'm buying it for my girlfriend." But the clerk said nothing as she rang through the purchase except for "Have a nice day." That done he went straight home. His girlfriend Tamara was away for the weekend. Jim wanted to try on the dress right away and then experiment with Tamara's makeup, try on a couple of her purses, shoes, etc. He took off his clothes and felt a rush as he slipped on his first dress, just like the feeling he had back in the store. He opened the closet to store his male clothes and there IT was. A summer dress similar to the one he was wearing, just a lot smaller. It was Tamara's. "That's interesting," was all that Jim thought. For the rest of that evening and weekend Jim lounged around in his first dress. He even watched football on Sunday afternoon wearing his pretty dress. He tried on every shade of lipstick, eye shadow, and blush owned by Tamara. But he was careful not to use too much of any one thing so that Tamara wouldn't notice... he hoped. Just a half hour before she arrived home, Jim had finished cleaning up the makeup and hiding the dress; running through his mind were ideas for the next time she was away!

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Like most self-employed people Becky was struggling as a hairdresser during lockdown. No clients meant no money, but the bills didn’t seem to stop. She’d already resorted to cancelling every subscription she had and had even sold her TV on eBay. But she was still short of cash. At twenty-six years old and living the single life she had no one to help with the bills.Out of desperation she’d texted one of her clients to see if he needed a haircut and didn’t mind breaking the lockdown rules to...

Spanking
4 years ago
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First Swing Party in a Prom Dress

Cindy and Dennis stand outside the large mansion that has a swinger's party tonight. Dennis had called yesterday and got an enthusiastic invitation. Cindy was a cute blonde 18 year old recent high school grad. She is wearing her beautiful pink prom gown that barely holds in her full breasts and shows off her slim figure and firm small ass. Dennis told her to dress very nicely and Cindy had learned the hard way not to say no to Dennis. He had spanked her sweet ass until it was beet red when she...

2 years ago
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My first Dress

My first dress By Dedra Post This is one of my short stories about my life as a cross dresser. The beginning I had just turned 8 when Linda came to work for us as a live-in sitter/housekeeper, mom had put a advertisement in the help wanted section, Linda was the only one that would work for the salary mom could afford. She had just moved away from home in Washington state. She had lived with her father and four brothers and had the home maker for them since her mother died...

2 years ago
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Milwaukee Cuckoldrsquos Wife and the Crossdresser

Judy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her...

3 years ago
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Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

4 years ago
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Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

3 years ago
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A Confession A Night of Firsts

I hope you enjoy it. Please PM me or comment below and let me know what you thought. Of course I also encourage voting. If you go into the Forum section of the site you will see the Sex Stories Section. The CAW10 entries are there... I strongly suggest reading them as they are wonderful and written by very talented people. Enjoy! A Confession – A Night of Firsts I am a bit worried as I write this. Mostly because of what I have done and what I know, with absolute certainty, I...

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