A month before I turned 30.
Four weeks after our first date.
Coincidentally, our wedding night.
Although by the “classic” definition, I’m a virgin, I don’t consider myself one. My story. A few summers ago, I reunited with an ex-, and my parents dropped me off at her new appartment. Basically as soon as we were alone, we went at it in her bedroom. As it was my 1st time I was unsure of stuff, and stopped performong cunnilingus when she started to drip white “stuff” and smell odd. I now know I was on the right track and should’ve continued. After, I just “frotted” her, and, petted vigorously.
Like a number of the other guys that have posted to this thread, I “lost it” to an older woman. Well, we were both “goin’ on 13”, but she was my senior by two weeks, so that counts as an older woman, right? Right???
We had known each other since age five or six, played hopscotch and marbles, etc. We weren’t boyfriend/girlfriend or anything like that, just kids in the same neighborhood. One warm Saturday afternoon, she climbed onto the crossbar of my bicycle and we rode to a rather secluded swimming hole, expecting a bunch of the other neighborhood kids to be there. None were. We found out later that they all went to the movies.
Instead of going behind a bush and changing into her swimsuit, she simply stripped and dove in. Then I was faced with a dilemma: Strip also, or get “out cooled” by a girl! I couldn’t have that happen, so I stripped too. After a few minutes of splashing around she swam to the bank and said: “C’mon, let’s do it.” There was no doubt about what the “it” was.
For a bed, we spread our clothes and towels on the ground under a huge old oak tree. This was the first time for both of us, and given our age, as you may well imagine, the first time was very clumsy, but the job got done.
Next we went back in swimming, horsed around splashing water in one another’s faces, laughing and so forth. Such a feeling of accomplishment and relief! No longer would we have to stare at the ground around the drug store when the older kids got into discussions. We could have that knowing look on our faces. We had “done it!”
Later, we went back to where the clothes were spread out and gave it another whirl. The second time was slower, with more preparation, and was much better for all concerned. 
For a few days afterward I wondered if the acquaintanceship/friendship would change into something different, but it didn’t. I also belatedly worried about pregnancy, but that didn’t happen either.
Having been previously informed about “rubbers” by my grandma, I followed the Boy Scout motto of “Be Prepared”. I had one of the older guys buy a package of six condoms for me, but it turned out that I didn’t need them immediately. A strange friendship followed in which we’d get together physically at various intervals, sometimes months apart. This continued until we were out of high school, moved away, and lost track of each other.
In the nearly six years that we both remained in the same neighborhood following the initial act, we’d always smile at each other when the subject of “losin’ it” came up. That fine, silvery, summer afternoon was a happy memory for both of us.
PS: This has been a very informative thread. I’m amazed at the range of ages and variety of experiences that have been related here.
OK - I feel unique. I’m still a virgin…and i’m PROUD of it… I"ll happily wait until I find the ONE right guy…I’ll also wait until i’m married, call me old fashioned if you wish, I honestly don’t care It kind of makes me sad that i’m not likely to find a guy who’s also a virgin - but that’s what I’d like… for us both to be virgins till our wedding night…perhaps i’m dreaming…but then, I may never have the opportunity to marry ayway. (pssssst…any 25 - 35 yr old virgin Christian guys out there? grin_
I’m 30 by the way…
Just 13.
Funny that this topic comes up now. Me and my boyfriend just took a walk down memory lane. We both lost it to eachother in high school, and we decided to go on a picnic for lunch this aftrenoon. The place we ultimatly chose was the exact place we lost our virginty to eachother between sophmore and Junior year. Under a willow tree in the middle of a state park in tall tall grass. We had planned out every last detail ahead of time, so we spread out this greep plaid sheet of mine and just did it. Not the best sex ever, but an experiece I’ll never regrett. That was also the same state park where we had our first kiss (also to eachother). It’s been on my mind all morning.