Vacation Sex: Older Woman & Virgin Cub

Ava 11
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?

11 Comments »

  1. Dustin July 7, 2012 at 1:55 pm - Reply

    I’m a 20 year old virgin and i’d love to loose my v-card to a cougar it would be so awesome! He’s one lucky guy to have that happen to him!

    • Ava
      Ava July 7, 2012 at 2:39 pm - Reply

      Hey Dustin, I highly recommend being with an older woman for the first time. I felt lucky too because I know I’ll always be remembered:)

  2. Dustin July 7, 2012 at 5:08 pm - Reply

    Yes im really considering it.The only problem is I really don’t know where to look for cougars. And would a cougar really be interested in taking a cub like myself virginity?

    • Ava
      Ava July 9, 2012 at 11:04 am - Reply

      Dustin, I recommend trying maturekiss.com as a place to meet older women. Most cougars (myself included) don’t specifically seek out virgins, but we don’t shy away from inexperienced men either. Wishing you a fantastic first!

  3. Ed November 20, 2012 at 1:09 am - Reply

    Hi, great article! Im 21 and still a virgin, i’m a rugby player and son to graduate from uni in london…
    I cant leave a virgin… help me Ava?!?

    • Ava
      Ava November 20, 2012 at 8:00 am - Reply

      Hi Ed, Thanks for writing, and congratulations on your upcoming graduation. I’m yet to have another experience with a virgin, so I’m glad I took the opportunity when it presented itself. Dating sites such as MatureKiss are great places to meet older women who can help you out. Also, read my post Tips for Cub Virgins to guide you through the experience. Wishing you a great first time, Ed.

  4. Edward November 20, 2012 at 8:14 pm - Reply

    Hi I am a 19 year old virgin and am eager to lose my virginity to an experienced older woman. Do you have any tips to help me? Ideally, I would like to enter into a long-term sub/dom relationship.

    • Lola Page
      Lola November 20, 2012 at 9:36 pm - Reply

      As Ava said, MatureKiss.com is a great resource for meeting older women who would be happy to meet for no strings sex. If you’re interested in sub/dom relationships, then my recommendation is BDSMdate.com. It’s the biggest bdsm dating site, and you’ll find people near you for sure.

      On a side note, I just want to mention that we don’t email advice privately to our readers. We think that any help we give you publicly can then help others with similar questions. If you want Ava to address a specific question, please use our Ask Ava form. Questions asked there will be considered for upcoming posts.

  5. guru December 19, 2012 at 10:05 am - Reply

    Hi I’m 37 years old hot. So I like older granny for sex. I’m working in Dubai, don’t have hope. I’m a rich man, not a very sensitive person.

  6. Miguel January 29, 2013 at 2:42 am - Reply

    i lost my v–card to an older women at the age of 23, we still fuck every week, and love to please her and eat her up, she also said she was down to get recorded but was afraid other women would contact me online lol… to the other guys that were like me eager to find a older women to fuck, just be honest to them and tell them strait up how you feel and would love to learn from them and please them

  7. Jay May 17, 2013 at 2:05 am - Reply

    I lost my virginity to a girl younger than me but I couldn’t cum. I had drank too much and it just didn’t happen. Then I happened to meet a cougar a few months later and she gave me the ride of my life. I came three times. I’ll never forget, she was on top, and I was getting really close, so I told her I was about to cum, expecting her to slowdown…but she grinned and rode me harder until I busted big time.

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