In the Beginning One of my first sexual experiences with another person was when I was about 11 or twelve and involved an older boy, Joel, who lived down the street from us. He and I were pretty good friends. We did a lot of things together; built forts, shot hoops, played football, played video games (Atari was all the rage!!!), rode our bikes around everywhere, listened to music, had sleepovers and snuck out at night to wreek havoc around the neighborhood. The coolest thing about Joel though was that he had his own porno mag collection.
When his folks were gone or late at night when they were sleeping he would pull them out and share them. It was mostly pretty tame stuff; Playboy, Penthouse, maybe one or two Hustlers. To me though it was like a whole new dimension had been revealed. I remember flipping though these magazines filled with pretty women in lingerie and skimpy clothing and being overwhelmed with a sense of awe. Joel would show me which ones he thought were really hot as I sat there wide eyed and nodding. I could tell how excited he would get when sharing them by the growing bulge in his shorts.
At some point he started rubbing his growing cock and eventually slid it out through the leg of his shorts. I had seen other boys cocks before and even my brothers' and father's, but had never seen a full on boner. His was a good 8" and pretty thick. I think I can safely say he is responsible for me having a size complex thoughout my teen years.
He told me stories about how he and his cousin would have these jack off contests. Whoever came first was the winner. I don't even think I really knew what cum was at the time. I probably only had had an erection a couple times at that point and had no idea what to do with the thing, but that would all change soon.
I remember him pulling out one of those industrial sized jars of Vasoline Intensive Care and starting to stoke his cock as he knelt next to the bed flipping though the magazine and finally settling on an image he liked. He offered me the jar and my own magazine and invited me to join him. I can't remember if I had admitted to Joel that I had never mastrubated before or not but I accepted his offer and tried my hand at it so to speak. That first time I think I only managed a few tiny droplets of pre-cum and felt a little embarassed about not being able to acheive any release. With a liitle more practice though I would soon experience my first orgasm, shooting jets of cum all over the bathroom wall, but that is a whole other story.
The reason I mention this whole episode here, in this journal, is what transpired in the weeks and months that followed this first experience and would come to pass as my first real adventure in crossdressing. You see, Joel also would introduce me to another little game.
I'm not sure how many of you remember those little Nerf basketball kits they used to sell. They included a little wire hoop you could mount on your door and a spongey little "basketball" that you could use to pretend you were Dr. J, Magic Johnson, or even Larry Bird (if you were little suburban honkies like we were.) Ooorrrrr . . . . . you could play another game (wink, wink, nod, nod to anyone that's ever seen Chuck and Buck)
The other game we played involved two Nerf basketballs and one of us playing the girl and stuffing them up our shirt while the other got to be the boy and feel "her" up. Whoever made the most baskets out of five shots got to be the guy while the loser had to stuff their shirt and be the girl. Of course he had the home court advantage so I was usually the one playing the girl and being felt up and I may have bouced a few off the rim (no pun intended) on purpose.
Most of our little role play sessions involved him coming up behind me and groping my "breasts" as he whispered dirty things into my ear in a throaty voice. Some times we would end up spooning on the bed. There were times I could feel his hard cock rubbing up agianst my ass and times that I think that I actually enjoyed it. Clothes were always kept on during these sessions and we would never touch one anothers genitals directly . . . that would be gay!!! But almost always we would end by pulling out the magazines and jacking off together.
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Hello Miss Delia. What a very sexy story. One of my favorite things is to chat about our early years of experimenting with sex, and the innocence of learning to enjoy our fantasies. I too started playing with other boys when I was about 10 years old. It involved a sleepover and a pair of his sisters nylon panty hose. It didn't take long for both of us to realize just what we wnated to do with each other! The rest was all so very natural, and we dressed played together for years thereafter. I have never written a blog about that night, but I still fantasize about it. It was so steamy and wonderful! Thank you for sharing your wonderful and sexy stories as well. I hope we can have a chance to chat sometime soon! Hugs, Roxy
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