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When I Was A Kid
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Straight Male / 21
Ex Boss
I recently came in contact with my old boss from my first job. Now I can’t stop thinking about this confession and how hot it was. When I was 16, I got my first job over the summer as a lifeguard. I was quite tall and skinny, not super fit or buff but I was a high school swimmer. I was also pretty shy at the time. I got along with everyone well and had a couple friends I still know from it. My boss however was very hot and attractive. She was 23, pretty young for a boss. She was just barely shorter than me, not busty but not petite either, red head, and eyes that you could drown in. In hindsight, I definitely didn’t hide my attraction for her well. The lifeguards were attractive but I really found my boss unbearably hot. I kept it to myself but again, I guess I wasn’t too secretive. She sort of flirted with me but nothing major and I thought I was imagining it until a friend said she was acting weird during a shift. Towards the end of the season, her car was “in the shop” and got a ride. Then she asked me for a ride home. I was thrilled to give her one but also just enjoyed doing nice things for people I like. We closed early because of weather and I took her to her apartment. As soon as I parked and looked over, she had her shirt and bra lifted and grabbed my thigh. I couldn’t believe what was happening and sat their like an idiot in shock. I snapped out of it when she started making out with me. Eventually she started blowing me in my car. Before I came she stopped and had me join her in her apartment. I had sex twice with my boss. It was the only time until I became an adult that I got to have unprotected sex with no worries. The first time she rode me and told me to cum inside her. I didn’t last too long but an impressive amount of time for a virgin. The load however screamed virgin as it was bigger than I have ever cum. The second time, I got to be more in charge of my own boss. I was pulling her hair and came in her again in doggy, albeit much less than the first time. The summer ended the next week and I never saw or heard from her again, until now. Now that we are in contact, I really want to hook up again. I’m sure she does too but she hasn’t said anything yet.
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