Confessions of a Peeping Tom

Posted in: Voyeurism

My girlfriend Jenny and I were together for 3 years in high school before we went away to college. We lost our virginities to each other at our junior prom, and had sex regularly for the rest of our high school career. This was all, of course, before she dumped me at graduation.
Just as we were lining up to get our diplomas, Jenny whispered to me that she thought we ought to see other people. When we threw our hats in the air, she grabbed the guy next to her and started to make out with him. I learned later that she had sex with 3 different guys that night, and that all she could talk about with her friends was how great it was to mix it up for once. One of the guys she fucked that night was my cousin.
I literally could not get the girl out of my mind. I hated her for being a slut, but more than that I was jealous and pissed that I wasn’t one of the guys she wanted to hook up with. Worse than that, I had to see her all the time. I was a lifeguard at the city pool, and Jenny was always there in some tiny bikini, either tanning or splashing around. I pretty much always had a boner when she was there – all her suits were tiny and it always looked like she was about to fall out. She was constantly hitting on guys, and a couple times I walked into the guys’ bathroom to find her blowing some dude in the corner. Once, when I was leaving the pool, I saw that her car was parked right next to mine – and she was straddling some dude in the back seat. We made eye contact as I walked by, my dick rigid in my swim trunks. Jenny reached up her hands and pressed them against the ceiling, moaning, making it impossible for me to not stare at her perfect tits as they bounced up and down. When I revved the car to go away, I could hear her moaning crescendo as she came.
It didn’t take long for me to figure out that Jenny loved when I saw her, and that she really got off on it. She made an effort to hook up with guys at places she knew I was going. She started hooking up with my neighbor across the street, even though he was only 15, and they were constantly parked outside fucking where I could see them. I’d have to walk inside immediately, not to avoid watching, but so that I could jack off.
I figured that, once we got to school, things would be better. We were going to the same state school, but it was a huge campus and I figured I’d never see her. Then I could move on and get some action from a new girl, instead of just my hand while I thought about my old girl. I figured wrong.
There I was, moving into the dorms, excited to meet new people. I got all my stuff in, met my roommate, hugged my parents goodbye and went to get settled into my space. I opened the blinds on my window, and noticed that across the way, maybe 15 feet of alley space between us, was another dorm. Most of the blinds were shut, but the window just across and down from mine was open. Sitting in the window was Jenny, looking up at me. She waved, smirking. Then she looked across my building, probably scanning for other open windows, and took off her shirt. Eyes on me, she backed up onto her bed, shook off her skirt, and lay down. I think she was checking to see that I could watch her if she was on her bed. I could. She licked her lips, then reached down under her bed, retrieving a vibrator that I didn’t even know she owned. She pushed off her panties and bra, then turned on the vibrator and started using it on herself, first on her nipples then on her clit. I couldn’t stop staring, and I couldn’t stop my hand from slowly reaching down into my pants and pulling out my dick while I watched her. She smiled when she saw that, and then with one quick movement stuck the vibrator into her pussy. With that, my hand started going back and forth.
It didn’t take long for us to come, me watching her masturbate and her watching me jerk off to the site of it. When she saw my jizz hit the window, she arched her back and moaned in ecstasy. Then she smiled, slipped into her clothes, and blew a kiss at me. She grabbed her purse and mouthed at me, “Don’t move. I’ll be back.”
When she came back, she had a guy with her.

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