Have You Ever: Popped Someone’s Cherry?


Taking someone's virginity isn't easy. Trust me, I know from experience. For reasons unbeknownst to me, I seem to be some kind of magnet for guys who've never been fucked before. These guys aren't necessarily inexperienced in the sexual arena. They've just never met the right person. Or some of them are just beginning to explore their versatile side. And others are just coming to terms with their sexuality and desires all too late in their life.

The first time I've received such a request was during my freshman year in college. A new friend and I had began fooling around innocently. After a few sessions of tonsil hockey and mutual blow-jays, he asked me if I'd be his "first". I believe his exact words were, "I don't want to fuck it up with someone who matters." How very flattering!

Our attempt ended disastrously, to the point that I didn't even get my dick in halfway before he cried out in pain. We didn't ever try again and stopped hooking up shortly after. I've learned from this experience and others, and now I've mastered a technique for preparing a guy for the big moment (more on that later). In fact, this question came to mind after successfully popping a hot college jock's cherry this past Wednesday. His invitation–"You have the perfect dick for it"–was a lot more complimentary…

But enough about me! Now it's your turn to share some stories, whether they be disastrous or totally hot. So tell us, and tell us all the juicy details–have you ever popped someone's cherry?

– Dewitt

Photo credit: Corbin Fisher

For photos of Elijah getting his cherry popped, follow the JUMP:














404 thoughts on “Have You Ever: Popped Someone’s Cherry?

  1. Hey–the big thing is getting that technique right for the first-timers. Perhaps you’ll need to show me how that’s done (or at least teach some of the tops I’ve been with–I’m a sensitive bottom.)

  2. Yes I have and it was DAMN hot! The worst mistake guys make bustin’ the cherry is to take their dick out when the “OW OW OW’s” start. Do not do that! The pain of that asshole slamming shut upon withdrawl and the following ass-cramp is what I think most guys associate with anal sex. The key is to get the hole very relaxed and then slowly slide it in. When the pain starts have the bottom breathe thru it and let them back up on you when they feel they can.

  3. first guy I ever had sex with convinced me that hand lotion was just as good as lube — which it might be, if you’re a big ‘ole loose whore — but for someone’s first time, it definitely IS NOT THE SAME. I swear I felt constipated for like a month.

  4. Darson… maybe it’s me but when i bottom, and i’ve been fucked quite a few times, but the initial penetration is always excruciating pain. I have to tell the guy to pull out for a few seconds. But after that, shit he can pound me like a jackhammer.
    I’ve never took anybody’s cherry, but i remember the first time i bottomed was a good experience, it didn’t hurt at all. But the next morning the guy tried to fuck me again and it hurt like hell when he slid it in.

  5. It took me a couple of years to persuade my ex-husband to try bottoming, and I had to agree to buy him an iPod. Ever after that, I called him my Pod Whore. He decided I was too big for him and never let me do it again.

  6. Darson I totally agree that the worst thing you can do is take it out when it hurts…as a very experienced bottom myself, best thing to do is ease in slowly, and KEEP moving it around, the more you move back n forth, the sooner the pain eases off

  7. I’m a vers. and love it both ways…
    Even now after many years…a lot of times its much easier for me to get teased open…put it in, take it out, put it back in, take it out…then you can have it how you want, pound the hell out of it…
    I’ve got almost 9 and thick, and some cherry guys relax and take it well, with other guys its like cracking open a safe, but to me the three most important things are…too much lube is never enough, listen to what the bottom is saying, and patience, patience, patience!

  8. I’ve found that the position really matters – it should be one that puts the bottom in control – spooning is a great way to start. The top can ease into the bottom and the bottom can push back if and when he wants to.

  9. I recently popped someone’s oral cherry. Does that count?
    A few weeks ago I was at a bathhouse and I gave head to this one guy. He didn’t finish so we parted ways. 2 weeks later, we just happened to be there at the same time and I was sucking on him again. He kept pulling away from when he would get close and after telling him that I wanted him to finish, he told me that the first time I had sucked on him , I was the first guy and the only guy to have done that.
    After some persuasion, I was able to talk him into finishing. It was quite hot.
    I think later on that evening I saw someone else giving him head….

  10. When it hurts, the top should just stop, and hold it still inside, until the bottom gets over the ow factor, relaxes, and starts asking for it.

  11. It’s not only all about the proper technique, but the ability of the top to be patient with the bottom and stick to the right technique.
    I myself am a very tight bottom. My back door contracts back to it’s normal shape and tightness after every penetration. I’ve been with guys who are on the average size and they really caused me terrible pain. Once i was with a guy who gave it to me so comfortably and made me really beg him for more…and guess what he was more than 10″ and really thick, but man that guy knew that i’m tight and exactly what i need.

  12. my first was 10 years after I came out. I was about 33, dating this guy in Philly, and after he fucked me I said “Well, that was a first!”. He asked me what I meant, and I told him I had never been fucked. he was quite large (for a beginner – at least 8 1/2″) and it did not hurt a bit. What hurt was when I met him in the local leather bar for old-timers (no longer there) the next day, and several guys gave me a knowing nod. One actually said to my buddy, “So THIS is the virgin?” I was furious, but we continued to date for a while until it became clear he wanted nothing more than sex.

  13. Yeh, I have. 2nd time is the charm.
    First with my best friend in early high school. It hurt him and we stopped and never went there again.
    With my partner now. He’s the younger and I’m the older in our relationship. Our first time together was his first time ever. I made sure to make it so gentle, caring and a warm and comfortable environment. It was magical. The look on his face was pure ecstasy, the natural way.
    Thank God, we are approaching our 5th year together. And he feels just as good today, if not much better.

  14. I have penetrated a cherry ass more than once and each time after entering” I like to rotate ( counter clock wise ) this usually help the bottom 2 loosen up and once he lose enough I like 2 put the bottom on his back ( legs spread wide apart ) 4 some slow motion drilling making sure 2 hit the prostate just right while corkscrewing turning ( left 2 right )and b4 U know it he is begging 4 me 2 Jackhammer ( hence the name ) his ass until he CUMS !!!

  15. I popped a 30 year old’s cherry. Was hot, but i was still at that teenage stage where i hadn’t built up the stamina to fuck someone properly. It went in fairly easily but then he told me he’d taken some fairly big objects while home alone.
    I agree with Versatile Guy, if i get that pain (and i nearly always do) take it out for about a minute, then you can shove it back in and go for your life!!
    However this method doesn’t work for everyone.
    I’ve also popped a guy’s “enjoyment cherry” if you will- the first time he took a cock and loved it. That worked out because i was slow and rubbed all around the area and because I precum heaps its all well lubricated and helps the motion and eventually it can basically almost fall in because the hole is begging for it.

  16. BLACKJACK, don’t be so lazy when you write. You aren’t texting, you are typing in a blog, as I have mentioned before. It is sad that folks today just think it is too hard to write whole words so they resort to numbers. If texting had never been invented, the language would not be degrading so badly.

  17. I’ve only popped one cherry. The kid was 19 and we’d been chatting for a while and he kept saying how he wanted me to be his first and asking questions about getting fucked. I explained some basic “facts of life” and gave him advice on preparing for the event (cleaning and such).
    WE started the evening with a shower together, so that I could ensure hygiene, and to help him relax. Then I laid him face down and settled in to rim him. My thought was to give him the fill treatment and get him as hungry for it as possible.
    Once he was relaxed and wet, I took a silicone butt plug and placed it in my teeth and used it to slowly probe him a little deeper. (I’m not overly endowed, but my cock is thicker than average.) He said the sensation of getting penetrated more deeply while feeling my lips slide around his asshole was incredible.
    Once I was able to insert and retract the plug using only my lips, I shifted him to his knees and removed the plug, replacing it with my well-lubed cock.
    He was still super-tight (it was a smallish plug) and best of all, the long ramp-up meant that he was ready to cum much sooner and came while I fucked him, which is my personal favorite thing. (I make all my bottoms at least jerk-off while my cock is inside them, and my partner gets himself close and holds it there until I’m ready and we can cum together.)
    But to sum-up, the keys to me are: prepare, over-lube, and take it SLOOOOOOOOW…

  18. Yes I have …several times…both twat and ass…gentle and kind was I…then I fucked the hell out of the bitches…lol…luved it…n so did they…they came back for more…

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