Have You Ever: Taken Someone’s Virginity?

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For the record, taking someone's virginity doesn't necessarily mean that they're a younger guy. If you knew the amount of older men whose cherries I've popped, you might gasp a little. Hell, it's even hard for me to believe. For some reason, I'm a magnet for guys who are having sexual awakenings and want to try bottoming for the first time. It's absolutely inexplicable.

As hot as it can be when the anal devirginization process goes smoothly, it's important to recognize that it's not always fun for everyone involved. Back in college, I had a friend who became more than a friend. He trusted me enough that he asked me to be his first. I believe his charming words were, "I don't want to fuck it up with someone who matters." Perhaps it was my bitterness over that statement, but I just couldn't get him to relax and get it all the way in. Or maybe I was just too big for him to handle. Either way, it didn't work out.

That's just one of my stories. Do you have any to share about taking someone's virginity? Was it an uncomfortable experience or did everyone involved seem to enjoy themselves? Discuss!

– Dewitt

6 thoughts on “Have You Ever: Taken Someone’s Virginity?

  1. Actually, I’m going to be taking someone’s virginity in about a week or so. . .I’m looking forward to it, and so is he!!! ;p

  2. I´ve got my cherry popped, By a guy who didn´t know what he was doing, I actually didn´t fell much, So I Don´t know if i had my cherry popped

  3. i popped my second bf’s cherry… we were in the back of my mom’s minivan, and as I was finally in and he was relaxed, he started crying… I freaked out,I pulled out and asked what was wrong since i thought I had hurt him badly… he said “I just love u so much…” I couldn’t get hard after that…

  4. I was 16, i totally breathed through it, the guy was huge and i was in massives amounts of pain, after wards he said, wow, you’re gonna be a power bottom someday… but, i swear after that first time, i never thought i would go back… i did, and i’m sorta power bottomish.

  5. Yes I have He was blonde with a muscle ass and a tight pink hole it took me a couple of minutes 2 get n & 4 his hole 2 relax but onces his ass muscle relaxed he would have worn me out if I did’nt call 4 time out . LOL ( Just kidding ) but we did FUCK 4 a long time……….

  6. not virginity virginity.
    but i’ve on some occasions been the first time the guy’s ever bottomed or topped or a few more occasions of being the first ever enjoying bottoming or topping? well, can’t remember…
    i’ve been atleast once a guys gay-virginity, but not nearly as many times as i tried/would of hoped to.
    other virginities can also be considered, just not the typical real one 😛

  7. yeah i got my cherry popped when i was about 16 by an older guy…he was huge and me(still to this day) am very small..it was painful but eventually felt better since he was such a nice guy about it

  8. I met this guy in a club. Very hot with his beautiful ass showing a bit in his jeans. Does that drive every top crazy, or is it just me? Well, we were all over each other on the dance floor and pressing against the columns. I realized then we were having two tops power struggle. We spent that same night together and he fucked me three times. Yeah, I know… Then it became sort of a relationship. Over the next month or two I managed to get him relaxed and trusting to fuck him. He said he’d never been fucked before and I could see it. He was completely cool with it and we were like 50-50 later on. Lots of fun, and yeah he had a beautiful ass. He loved me talking dirty to him. Little embarrassing when he told all his friends about it. lol

  9. 4 guys. one of which was in his mid 30’s and i was 21. he’s was gorgeous and i fucked his brain out.
    another guy i met online and i fucked him right before he had to go back home after school let out. I talked to him later and he said he’d never do it again because it hurt so much. two months later i get a text message at work that he’s been with his gf all summer and all he can think about is me fucking him. 🙂

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