1. Gary's Dressup Sissy


    Date: 9/28/2015, Categories: Anal First Time Shemales, Author: palmorr, Source: xHamster 

    When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games. One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One movie was all transvestite scenes. This shocked Gary but I found it a massive turn on. I'd been experimenting in wearing my s****r’s clothes for a while. Gary could obviously see this, so suggested I dressup. We went up to his s****r’s room and looked in her wardrobe. Gary immediately picked out her school uniform. She was a little younger than me, so when I slid into her grey pleated school skirt it was way above the knee. “Too short for school” Gary had commented. This went on for a few days. I would go over when Gary was alone. He'd have me dress up in the schoolgirl outfit, skirt blouse, panties and ankle socks, and we'd either play games or watch movies. Gary would tease me a little. But I could tell he liked me to dress up. Maybe he missed his girlfriend I thought. One day in his bedroom, with me in my usual schoolgirl attire, there was a clothing catalogue lying around; a big thick book ...
    ... full of clothes, Gary had been shopping for new football boots from it. I began to flick through the pages, looking at the beautiful women. Gary came and sat down beside me and closed the book, then opened at page one. We flicked through the catalogue together, commenting on the clothes, Gary would say how he thought I'd look good in certain outfits, making me blush, and I would choose ones that he should buy me. Eventually we arrived at the footwear section, again Gary picked out the shoes, always sky high heels. My cock began to stiffen, as I knew which catalogue section was next, as I'm sure did Gary, page 202, lingerie. &#034mmmm&#034 said Gary. I blushed. We flicked through the pages in silence. I waited for him to choose an item for me. He stopped at page 207. Black suspenders, panties bra and stockings. My cock twitched. &#034I bet you'd fuckin’ love to wear that wouldn’t you, you little sissy&#034 was Gary's response. Although a little surprised by the manner of his comment I said &#034sure&#034. I'd come this far, what was the point in being coy about it &#034I'd just love you to dress me like that&#034 Gary grinned a wicked grin. &#034Come on&#034 he said, darting from the room. I followed him into his mother’s room. He went straight to her bedside table and opened the bottom drawer. It was full with lingerie. All colours. &#034I found this lot this morning&#034 said Gary &#034 sit down&#034 I sat on the bed as he picked through the knickers, &#034don't mess them up ...
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