When I was five I moved to a new state, where I still live. I didn't really mind the move, except for the fact that I was leaving my best friend behind, a girl named 'Brooke'. Brooke was only a couple of months younger than me, our parents were good friends, and she lived in the same apartment building as me, so we ended up playing together a lot.
Anyway, much to my delight, Brooke's family ended up moving to the same town as we did, and only a few months after us. We stayed good friends for another couple of years, but then the cooties-age set in and we stopped liking each other as much. During those years, Brooke started playing soccer and got incredibly hot, and filled out very nicely (straight black hair, cute little nose, brown eyes, blonde hair on her body, pretty tan, thin, but not anorexic, nice firm butt, medium sized boobs, really long legs). When I got older I started to like her again and she became my 'crush' (and prime fantasy for wanking).
Well, our families have stayed good friends, so I have many chances to see Brooke at dinners and things like that. Plus she lives near me, is in most of my classes, and our dogs are best friends. Recently, she and her family left on a vacation to Florida, and I was asked to watch their cat. Brooke has done the same thing for us in the past, so I wasn't surprised when they asked me.
Whenever Brooke came to cat-sit for us, I would leave my bedroom door wide open, and my only pornographic possessions (a couple of sex catalogs) in plain view on my bed, partially covered by my sheets, in the hope that she'd find them. It always excited me to think about her masturbating to my catalogs, and fantasizing about the same pictures I fantasize about. One time, when I came back after a trip during which she had been cat-sitting at our house, one of my catalogs was missing, and the battery on my electric toothbrush was dead! I had just replaced it a week or so before we left, so I had little doubt in my mind that she'd been using it! That really turned me on, so of course, I had to go and wank away with it vibrating on my boner.
The first time I went over to feed her cat, I decided to go up to her room, which is on the second floor of her house, and see what it was like. I thought I'd also try and find some of her clothes and see what size her bras were and stuff. Well, I was in luck! She had all her clothes strewn all over the floor, including a bunch of bras and panties, and even a swimsuit. She was a 34-B bra size. I decided it would be fun to try some on, and see how they fit me, especially since reading stories about cross-dressing on this website. My favorite bra was this lime-green one that was pretty snug on me (the straps at least), and my favorite pair of panties was a purple bikini-style that made my butt look cute (even if it didn't begin to cover my boner). She also had a thong and two G-strings, but they didn't fit me at all, and were uncomfortable. By this time I was pretty friggin' horny and aching to wank, but instead I started compiling a whole outfit. I put on this little polo shirt thing that fitted pretty well and showed my abs and these stretchy jeans. I loved the way all her clothes made me look big and muscular, especially her shirts. Oh yeah, I also tried on one of her miniskirts, and a pair of mini shorts, and they both showed my butt and made it look HUGE. Anyway, once I had on a whole outfit, I started stripping it off piece by piece, pretending it was Brooke stripping and I was watching her. By the time I got to the panties and bra, I was leaking precum from nothing but the thought! Finally, I allowed myself to wank. I put the bra back on, and climbed up into her bed (which is elevated, like a bunk bed without the bottom bunk), and started jacking by humping her pillow. She had a silky pillow cover, and it felt so good! When I was just about to cum, I turned over and started pulling on my balls and closing my eyes and smelling her bed and imagining she was there and WHAM I ejaculated so hard that I hit myself in the chin, and covered her bra in cum. It was the most I'd ever done! I loved it! Then I cleaned up, and went back home.
The next day, I went back to Brooke's house to feed her cat again, except that this time I was already horny and prepared. I went straight up to her room, and quickly found my favorite clothes. Then I started to look for my missing catalog, and anything else she might have. I hoped that I might find a vibrator, a dildo, an electric toothbrush, something like that. After a little searching, I found this shoebox underneath a bunch of clothes in her closet. When I opened it up, I found, not only my missing catalog (which censors penises and pussies) but also a couple of porn videos (called 'Hot Cherry Pies' and 'Debbie Does Dallas: The Revenge') and a six-inch blue jelly vibe (which I later identified as coming from my catalog)! I had brought some Vaseline this time, as a lube, and so I was ready for some serious jacking. Brooke has a little TV in her room above the foot of her bed, and a VCR underneath it. I decided I would put it to good use.
I popped in the first video, which turned out to be all lesbian, and started jacking off with the Vaseline by putting some into a lockable baggy and squishing it all around so that it covered the inside of the bag. Then I stuck my fully erect six and a half inch long dick in the baggy, placed the package between two horizontal pillows, leaned on top of the top pillow to create pressure, and started pumping in and out like it was Brooke's pussy. It felt so good! That, combined with the video and the fact that I was in the same bed that Brooke masturbated in, made me ridiculously horny. I orgasmed in no time (and it was GOOD)!
Brooke and her family were coming back from Florida the next day, so I put everything back, but added a little note in the Nike shoebox saying that I noticed what was in it and that she could keep the catalog in return for a favor, but I didn't know what the favor was to be just yet.
That was five days ago, and she just got back to me (by the way, she got really tanned in Florida). I'll let you know what happens in a later posting. I gotta go right now, writing this has got my penis aching for a wank.