Vacation Sex: Older Woman & Virgin Cub

By my mid-thirties, I had never slept with a virgin and certainly didn’t expect to cross paths with one, let alone have a chance to pop his cherry. When I did fantasize about such an experience it would get me hot. Quick!

I was taking a much needed vacation in Central America a few years ago. Backpacking with a girlfriend, I was busy taking in the sights which included hunky hot latinos. I soon realized blondes get a lot of attention there. My friend wasn’t so interested, but I welcomed it. I had been in a dry spell and couldn’t get enough of the casual flirting. We were befriended by two men that gave us local tours and played guitar for us in the zocalo.

I’d always heard about women finding sex on vacation. Joao had gorgeous brown eyes, thick wavy hair, and a muscular build. He said he was 19, over ten years my junior. We got hot and heavy in a grassy park while our friends toured a nearby museum. He did seem a little inexperienced; he fumbled to unhook my bra and his kissing was not masterful, yet charming all the same.

I asked him if he was a virgin, and what I could understand (with the little Spanish I knew) was that he had a girlfriend but she said it hurt when he tried putting it inside her. I felt a lot of pressure, thinking I would be his first (you never forget your first) but I knew I’d be a good lover – gentle, experienced, loving, and patient.  And, I realized it might be my one and only chance to sleep with a virgin. I had to go for it!

Even writing about this now gets me a little wet. We ended up on a hillside outside an observatory. Fumbling in the dark, in nature, brought me back to my teenage days when finding a place to make out was part of the fun. It wasn’t mind blowing for me, but I think he enjoyed himself. Purrrr. I made sure to take it slow as I knew he’d come quick if I wasn’t careful. When I realized it was his first blowjob, I gave him an Ava special.

Joao kept in contact for years afterward, so I was sure I’d given him a memorable experience. This was pre-online dating when fulfilling a fantasy wasn’t so easy. Now, I think about seeking out another virgin. Maybe nineteen is too young, but I’m sure there are a few twenty-somethings out there that could use my help?

Cubs: Did you lose your virginity to an older woman? How was the experience?

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