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

Posts tagged “First Time

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.   (more…)

My first time – male

What was your first time like?  What do you even consider your first time?  Does heavy petting over clothes that miraculously leads to somebody creaming in the pants count?  What about the first nervous skin to skin contact of hands to genitals?  That first time of oral, where one or both of you were far more nervous and too inexperienced to have a chance at orgasm?  Or do you only count that first time a penis, a hard throbbing cock, slid into the unbelievably hot, wet caress of an aroused pussy?  (There was arousal, wasn’t there?  No?  Ouch!  I’m so sorry, ladies, I know that’s a bitch.)

My very first experience with another person in which bringing the ultimate sexual release was the goal came when I was 13, and was with my best friend, J,  at the time.  He and I attended the same school, we were in the same Confirmation Class at the Lutheran Church we attended, and we often spent the night at each other’s houses, sometimes over entire weekends.  After all, it was easy for one of us to catch the other’s bus on Friday afternoon, hang out on Saturday, and then go to church together on Sunday morning.  We were young, we were boys, and most of the time we spent our time watching movies or playing videogames anyway.

Unknown to my parents at the time, I was involved in a porn distribution chain at my Middle School.  One of my friends had been given his fathers back catalog of Penthouse magazines, stretching from the mid-to-late 1980s to the (then) current 1994.  I would buy these off my friend for $3 apiece, and after a few days of reading every story in the Letters to Penthouse section 4 or 5 times and absorbing each of the pictorials, I’d turn around and sell them to other classmates (usually the 6th graders) for $7 each.  It was decent money for me and left we with no shortage of masturbatory inspiration.