Wills Jack Off Journal

By Will Anderson

Published on Apr 28, 2003

Bisexual

Masturbating with Stephanie's Panties

I recall when I was 15 or so in early high school days, I still had a crush on Stephanie, who lived on the next block. Her parents had a lot of money and they lived in a really impressive house. She was this very cute and popular blue-eyed blonde, cheerleader-type.....a Meg Ryan look-alike. She was a year behind me in school.

Her family was away on vacation and they asked me to feed the cats, and told me where the house key was hidden. One night, I remember it was dark and rainy, I got their key and slipped into the house. I fed the cats, then went immediately upstairs to Stephanie's bedroom and started going thru her dresser and clothes hamper with a shielded flashlight. I stripped naked, and with a raging erection, I explored each and every pair of Stephanie's underpants for almost an hour. Those in her dresser were clean, but the ones in her hamper were freshly crusted with that wonderful cunt smell. Those brownish-yellow slit crust that girls deposit in the crotch of their panties had became an obsession of mine at a very young age. Over the years I'd gotten a number of glimpses up her shorts or her skirt to her underpants when she got careless about not keeping her knees together. All boys that age yearned for shots like that. I recalled how hot and worked up I became when I had jacked off, fantasizing about reaching up Stephanie's dress. But this was better!

That rainy night I proceeded to have my own private orgy dressing up in Stephanie's panties, slips, skirts, garter belts, hose and bras. I pretended that I was she, and we were making out in the back seat of my dad's car. I imagined my hand running up her skirt to her panties, then my fingers slipping under her panty leg opening. My balls and asshole, and rock-hard penis had now became her sex organs in my fantasy that night.

I lub'd up my finger and shove it in and out of my asshole envisioning it was Stephanie's cunt and asshole under the panties. I remember I even went down to their fridge and found a large carrot, which I gnawed to a round tip, greased it up with some Vaseline from their medicine cabinet, and then proceeded to pull the white cotton underpants aside and fucked myself wildly with my new vegetable helper. As I did this, I very slowly masturbated myself, while sniffing the crotch of her freshest and crustiest panties pulled tight against my nose and mouth. I licked off the remnants of Stephanie's pungent cunt crust as her panty crotch became soaked with my saliva. It became a challenge not to cum too quickly, which wasn't easy given my state of arousal.

Finally, I couldn't stand not cumming anymore, so I lined up a dozen pair of her clean panties on her bed, jacked off with the carrot up my ass and shot semen, spurt after spurt, into a drinking glass from her bathroom, then poured my cum into the crotch of each of her panties. After my ejaculations subsided I rubbed the cum into each of her underpants with my stiff penis. I was careful not to deposit too much sperm as to make it too crusty or noticeable. I took her hair dryer and dried each panty crotch so they wouldn't stick together later. I then folded each up neatly and replaced them in her drawer as I found them. I kept some of the really crusty dirty ones for my collection at home to wear and jack off with later.

In the following weeks after Stephanie returned I couldn't help but get excited every time I saw her, thinking of my very own cum in every one of her panties, nestled right up against her warm moist vagina and asshole. My adolescent fantasies were quite intense back then, as I never had the opportunity to experience sex until much later. But it wasn't for lack of desire....just shyness, lack of confidence and fear of rejection. I had to settle for vicarious sex with various girl's thru their dirty underpants.

Next: Chapter 5


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