When My Virginity & I Parted

This story is about my first time.

I'm an avid journal-keeper and historian-by-nature, which means that erotic encounters are dissected and classed and kept. In truth, though, my commitment to record-keeping began many years after my virginity and I had separated, so the record I made, a dozen years later, is hopefully more mental recollection than imagination.

It begins thus:

I was 19, and my sensual/erotic connections before then had involved lots of snogging, playful explorations under and around bras, and more than a bit of fumbling in cars. Plus skinny dipping. A surprising amount of skinny dipping.

My formative years were spent in a large country town. There was not much to do, sort of: drive-ins, working on cars, swimming in freshwater creeks. Although the town is on the ocean, in summer the waters are infested with box jellyfish, nasty little buggers with nasty little stings, so we had to stay in freshwater. I only once had a single tentacle on my arm, and the welt lasted for days.

I met a group of people who worked for a long-gone department store. An eclectic batch of 19-24 year olds, mixed gender. I have no clue now as to how we met, but the group 'worked', and we went camping, went to drive ins, had picnics. I have no idea how I met them, and absolutely no idea how, one night, I ended up in a spare bedroom with a 23 year old called Lisa. There was alcohol involved, not too much, and then we were kissing. Since I have since tracked her down on Facebook, I know that she keeps the same body shape: about 5'4, slim, short brunette hair, flat-chested. I honestly don't remember the progression, but I can still viscerally feel her hand as it slid down my jeans and grabbed my penis. It felt so very good. This went on for some time. Kissing, touching, stroking (still I had my jeans on), until Lisa asked me, 'What would you like?' I've never been a good one for being able to articulate my needs -- I just wrongly assume people will understand them -- and hesitantly replied, 'Can you suck me off?'

To be honest, I didn't expect it. Soon, though, my jeans and underwear were down, and I felt a soft mouth on my cock, moving rhythmically, I didn't cum. I was so intent on the feelings and novelty of it all, and in any event I think we might have been interrupted, so that was the end of the night.

You'll have guessed by now that this was not my first time, more the prelude to it.

So, a week or so later we are all out again, but this time I am going back to Lisa's place. She lived in a small 1970s wooden house, neat, small rooms. I didn't pay too much attention, being in a sort of distracted fog, wondering if tonight really was the night. It was!

We moved into her bedroom, and the action started. Kissing, touching, undressing. I mentioned Lisa was flat-chested. I should have added that she had literally no hint of boob, but big nipples. I really like nipples. I spent a lot of time licking, sucking and otherwise fondling them. I think she liked it. I hope so. Then I decided to head south, and this was my first time giving oral sex to someone, so I'm not sure how successful it was. I think I found her clit and not too much uncontrolled finger-banging stuff, and I do remember vividly her saying to me, 'Are you sure this is your first time? You're really good at it'. She probably said it to encourage me.

Did I mention she was married? No? Woops. But no fear, because her husband was in jail. I actually went with Lisa to visit her husband in jail (and with another guy, just as Lisa's friends). That was scary -- he was somewhat neanderthal, and soon after our visit ended up stabbing someone. Thoughts of him did flit through my head from time to time over the years; they were usually thoughts of being strangled by him because I had laid hands on his wife.

Where was I? Oh yes, being brilliant at cunnilingus. Then Lisa brought me up so we were level again, kissing and more fondling, and then her hand guided my cock inside her. Goodness, I still feel it. That first moment when flesh enclosed flesh, the warmth, the closeness. We stayed in a missionary position, with lots of motion, her logs locked on me, and probably sooner than she hoped, I came, shudderingly.

This is the bit I'm not so proud of. We hugged and kissed more, and then I excused myself and went to sleep in the lounge.

What?

Yep.

I needed time to be able to process everything that had just happened, and I couldn't do it with someone else. I still feel squicked, even now, wondering what idiotic ideas I had that made me think I should abandon this nude and lovely person to go into another room and wander inside my head.

The tally so far: Oral sex, tick. Lost virginity, check. Empathy, tact and 'afterglow', fucking big fail.

If time could unwind I would stay with her, ask what I could do to get her off, if that's what she wanted, and wake up next to her, again, if that is what she wanted.

There was an after-event of sorts, though not a flattering one. She and I never caught up like that again, but she did with one of the other guys in the group, and swiped me with 'His dick is smaller, but at least he knows what to do with it'.

Ouch.

Lisa, I doubt you'll ever read this. If you do, thank you. And sorry.

And now hopefully you're own 'first time' story will be way less embarrassing than mine.