An Absinthe-Loving, Polyamorous, Kinky, Sex-Positive Couple talk about all things Sex, Kink, and LGBTQ.

My first time – female

I wrote yesterday about how my first interpersonal sexual experience was with one of my best friends, and how it was scary and nerve-wracking and exciting and wonderful all at the same time.  Sometimes a first encounter is like that; the two people know each other well enough to work well together long enough to make something special happen.  Other times aren’t always so magnificent, but as life milestones they become resilient in memory nevertheless.  Such was the case for me during my 10th grade year of High School, when I had my series of firsts with my girlfriend at the time, B.

In the summer of 1996, at 15 years old, my Air Force father was relocated from Patrick Air Force Base in Melbourne, FL to Maxwell Air Force Base in Montgomery, AL.  We were quasi-familiar with the area and intimately familiar with the base; we’d been stationed there from 1986 to 1993, but had lived in the suburb of Prattville that first run through.  This time we were “in the city”, and I was entering High School as “the new kid.”  Granted, I wasn’t the only one.  Military-heavy cities see a high population cycle for “Brats”, and this particular school was no different.

One of the difficulties was finding somebody to date.  Most of my classmates came up through Elementary and Junior High together, so they had rapport established and knew where all the social circle boundaries lie.   I got to try to navigate that new landscape blindly, feeling my way carefully around who I liked and had a reasonable chance of having my interest reciprocated.  Come mid-October, I had firmly established crushes on C, D, and B.  (See, even then I was Poly and didn’t know it!) The only problem I had was, I could not for the life of me tell if any of them even had a glimmer of an interest in me.   I looked for ever sign I could, but as a dense, hormonally driven, geek of a teenager I had no clue the signs to look for.  None.

Until I got a note from B.  She had a thing for me and wanted me all to herself.   So I took that note and ran with it, and by Thanksgiving we were a couple.  I swore up and down, good little Christian boy that I was at the time, that I wasn’t go to try anything with her.  That didn’t last long.  

One of the first dates B and I had was to go see Star Trek: First Contact in theaters.  I grew up watching the series and the movies and for me it made perfect sense, plus it let me get in some snuggle time with B and get a sense of where things would lead.  We ended up, in typical teenage fashion, making out most of the movie.  And not one to pass up an opportunity, Christian upbringing or not, I let my hands wander.  And wander they did.  Up her shirt.  Under her bra.  Into her pants.  And there, in the most inglorious locations of the local cineplex, for the first time in my life I slid my hand inside a pair of panties and slid my finger inside the hot, wet, velvety embrace of a pussy.  I didn’t do anything so magnificent as get her off right then and there — I was too naive to fully know how yet — but she moaned into my shoulder and neck as I slowly pumped my finger back and forth, my hand movements pushing the limits of what her pants would allow.

As teenagers are wont to do, we saw each other as often as possible, making out in the halls between classses and going over to her house for “supervised” dates, which really meant her parents and younger brothers in a different room while we watched TV in the back room and made out on the couch.  Which led quickly from making out to hands inside pants, and she took a very quick liking to stroking my cock.  With a bit of teenage coaxing, by New Years her stroking my cock led to her having a go at sucking my cock.  She wasn’t an instant natural, but she was enthusiastic and started asking to do so every date we had.  My house, her house, or at the movies, if she could get me in her mouth, she would.  But with one problem.

Try as she might, B couldn’t keep her mouth open long enough to get me close to cumming from oral.  Her jaw would tense and start to ache and she’d have to stop, and despite her attempts her hand strokes (even with coaching) just weren’t firm or fast enough to get me close either.  So we reached a compromise.  She’d wrap her hand around me.  I’d wrap my hand around hers.  And with me controlling her, I’d use her hand as a stroke toy.  I’d squeeze her around my cock, sliding her up and down, until I started getting close.  Then she’d lean over, taking the head of my cock and part of the shaft between her lips, and suck hard while we finished stroking me to the point where I was cumming hard, filling her mouth.  It in no way prepared me for me for the proper blowjobs I would receive later in life, but at the time they were wonderful, and they got me used to the visual of my cock sliding between a set of luscious lips, which I still love.

We continued on the oral and fingering track for months, with her guiding me to her clit and teaching me how to hit it from outside her pants rub the seam of her jeans against her.  We snuck gropes and grabs and kisses whenever and wherever we could (much to frustration of our friends).  We’d go on double dates to the movie with our best friends (who were also dating) and end up watching each other as shirts came up or blowjobs were given with only an empty seat between us.  We talked abut having sex, wrote erotic letters to each other about having sex, and had phone sex telling stories about having sex.  And finally, come late April, decided we were actually going to have sex.

My parents were out of town for a weekend in early May.  My brother was staying at a friend’s house for the weekend.  I was staying with one of my friends nearby.  That Saturday my high school soccer team had an end of season barbecue scheduled at a local park.  She’d come to all my local games and had the okay to come to the barbecue.  It was the perfect combination of timing.  We agreed 2 weeks before that we couldn’t find a more perfect time, and she got a couple of condoms from one of her friends the week before so we’d have some protection.  And finally, the day arrived.

I picked her up from her house and told her parents I’d have her back by curfew.  We drove straight to my house, nervous and excited the whole way.  We slipped into the house and up into my room, where I put on some music (I don’t even remember the artist or album anymore) and started making out while  slowly stripping each other.  We’d never been naked in front of each other before.  Sure, we’d pulled up her shirt and pants and underwear had been pulled down, but we’d never had all our clothes off and been able to touch fully skin to skin unencumbered.  She laid back on my bed, and for the first time I lowered my lips between her legs.

I knew B’s taste.  I’d licked and sucked my fingers dry after fingering her, but I’d never had a taste straight from the source.    She was wet and musky and delicious, and pulling everything I’d ever read to mind licked stem to stern and wrote the alphabet and sucked and flicked and did my absolute best.    And kept working at it until finally — FINALLY — I brought B to her first non self-induced full blown orgasm.   My oral skills seemed to be the key to my success!  I kissed my way back up her body, my cock hard and throbbing and ready to burst.

Wanting to return the favor, B rolled me over and knelt between my legs, working as much of my cock into her mouth as she could, bobbing up and down, but again we didn’t make it very far before her jaw again began acting up again.  So we swapped places, with her laying down in front of me.  I grabbed the condom, rolled it on, knelt between her legs, slid the head just into place, and leaned down to wrap my arms around her as I worked my hips slowly until I was there.  I was there!  For the first time in my life my cock was buried to the hilt, completely embraced by a ready and waiting pussy.  No hand, no mouth, nothing had ever felt this good.  I lay there kissing her, letting her adjust, before I started moving my hips.  Slowly at first, feeling her grasp the entire length of me, and building up to a firm, semi-fast rhythm.  I held that pace for several minutes, her hips barely moving to meet mine, before she said seven words I will never forget.

“Are you going to be done soon?”

This wasn’t in the middle of some multi-hour marathon fuck.  We hadn’t been switching positions or grabbing for lubes or stretching out cramped muscles.  This was less than 10 minutes into standard, classic missionary sex!  I decided then and there to read every sex advice article I could ever get my hands or eyes on, watch every How-To video I could to never have my partner sound or look bored with my performance ever again.  I also decided to fuck her instead of trying to make love.  I thrust my soccer-trained hips as hard and fast as I could, not caring if I bruised B or not, and a few short minutes later exploded in my first orgasm during penis-in-vagina sex.

We got dressed shyly.  We left my house, less than an hour after we got there.  We went to where the barbecue was scheduled, but it had been cancelled, so I took her home.  Neither of us really spoke much.

We dated another 2 months.  We went down on each other a couple more times, but we never had PIV sex again.  I wouldn’t have it again until 2001, 4 years later.  I forgot the taste of B, the smell of her hair, and the feelings of her skin under my lips.  We saw each other at school over the next two years, but never had any classes together.  Eventually I forgot the sound of her voice.

But I’ll never forgot that blank look on her face and those 7 words she said.


Stay SINful, friends.

4 responses

  1. OUCH!

    Mr. No Name

    April 11, 2012 at 9:20 pm

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