My First Orgasm

I don't know why I've always been fascinated with how people discovered masturbation and orgasm.  Here is the story of how I had my first orgasm, on the floor of my best friend's bedroom.    When I was 13, my best friend Jeff and I used to do this goofy, innocent thing where we'd take our pillows and give them the names of girls we liked in class.  We would pretend they were real girls and we'd make out with them.  It was all fairly innocent.  We were never embarrassed or shy in front of each other, and really never thought we were doing anything naughty.     Jeff would usually name his Michelle, and I would name mine Jessica after our current crushes.  We would do this when we had sleepovers. Nothing much would come of it except I'd get aroused as I'm sure Jeff did. The first few times were fairly harmless and I have no memory of it going much further than a make-out with our fake girlfriends.     I do recall the first time we really got into it.  We were watching a rented movie, likely a horror movie where the lead actress ended up topless at some point.   Remember, this was the 80s so there was no internet porn so seeing breasts on a grainy VHS rented move was pretty hot for 13 year-olds.  Well, for whatever reason our pillow makeout that night was hot enough where one of us popped our erect penis out of our boxer slits and we began grinding against the pillows.  I don't remember if it was Jeff or me that had our penis out first, but I do remember at some point we both had erections sticking out of our boxers.  We made innocent comments about how horny we were and how hard we were and we took stock in each other's hardons.  We were mostly the same size, but I was a tad thicker and mine is curved to my right, where Jeff's stuck straight out. Like I said it was no big deal for us.  That night we just sort of ground into our pillows and eventually just stopped.  I had no idea how to masturbate or what an orgasm felt like, so I don't think either of us knew what to do.    Fast forward to the next sleepover. One of our friends in the neighborhood had a playboy magazine. I actually remember it as a "Playboy's Book of Lingerie". It was not filled with ads and stories, but rather all photos of models in various forms of lingerie, or naked.  Jeff told me he had it at his house and we'd look at it that night.  I was absolutely shaking with excitement as I raced over.  We could barely contain ourselves as we played video games and watched tv until his parents went to bed.  Then he decided to get the playboy and bring it to the basement rec room.    We spent what seemed like an eternity slowly and silently  turning each and every page together as we admired these beautiful women.  We had barely ever seen a real porn and the internet didn't exist so this was one of the most arousing nights of our lives.  As we thumbed through the pages we would comment on what girl we thought might have the same breasts and nipples as Michelle or Jessica, the real girls who we personified in our pillows.  We were so nervous as well as we didn't want to get caught by his parents, so all you could hear was a few whispers, some page turnings, and our breathing.     At some point we heard a squeak upstairs and Jeff agreed we should head to his room.  So we took the playboy and made our way to his basement bedroom.  We joked with each other as we noticed the erections pushing against our boxers. We were both wearing t-shirts and boxers, as we were just basically ready for bed.    In Jeff's room, he got on his single bed, and I sat cross-legged in the floor next to his bed. We each grabbed a pillow and started to make out with them as we tended to do. He and "Michelle" and "Jessica" and I went to town. Now, you have to remember that I knew the word "orgasm" and knew of "coming" but didn't know what it felt like or how to get there.  I had erections for as long as I could remember and likely played with them but never with and end in mind.  We were innocent in our pillow play but knew grinding and rubbing was in part of the process.     Because of the playboy and the eternity sitting in the other room thumbing through some of the most erotic imagery I'd ever seen, I was super horny and so was Jeff.   We absent mindedly made out and grinded on our pillows  when I couldn't take it any longer and I maneuvered the slit in my boxers to allow my erection to spring free. I was lying on my back and my next discovery changed everything.  I knew the most sensitive part of my penis was the left side of the head. So I took the pillow and laid it on my torso, just to the left of center, so the right edge of the pillow contacted the left side of my erection. I then took both hands and started to rub the pillow up and down....towards my feet then up towards my chest.  This rubbing motion stimulated the left side of my penis as the pillow passed up and back along that sensitive left side of the head.  In the past, I'd ground my naked penis against the pillow, but pulling the pillow up and down like this made me feel much better than ever before.      I glanced up at Jeff who was on his stomach with his pillow beneath him as he kissed it and ground his hips into it. I couldn't tell if his penis was out because we never took our boxers completely off.  We always just let our erections poke out of the slit. He glanced and saw me too but didn't really say anything.  We just did our things and never made it a big deal.     The next part I will never forget as long as I live.  As I laid on my back, sliding the pillow up and back over and over, my penis would occasionally also, due to the pressure, flip up against my stomach and down toward my leg as the pillow changed direction which didn't feel wonderful.  So I eased up on the pillow's pressure until I could rub the edge of the pillow against my erection, but keep my penis in the same position, as straight up as my slight curve allowed.  As I did this I got this deep, unique, extra-horny feeling that only happened a few times in my life.  I got a tingle that started in my belly button and travelled through to my anus.  A level of arousal seldom felt ever since.  Usually in these pillow makeout sessions we'd both just stop for whatever reason but I decided to keep going and see what happened.  I still remember the pattern on the light on Jeff's ceiling.  Before I could even understand what was happening the tingling started in the left side of my head, extending down my shaft into my groin. I held my breath and silently laid in absolute bewilderment as the first orgasm of my life tore through me.  It was the absolute gratest thing I had ever felt. A sensation so strong that my arms were tingling and my vision blurred as I stared at the pattern in that light on the ceiling.  I remember having to stop the pillow's movements as the pleasure was so intense and the head of my cock was so sensitive I could barely touch it.  I had no idea what happened. And I was too young to ejaculate any liquid. At least I don't remember anything coming out. I only remember the orgasm.    I turned to Jeff who was stil on his stomach making out with his pillow. I stopped him and told him something happened that felt so good and I was super sensitive. Being 13 I was still rock hard and I wasn't sure why I could barely touch it now without it being painful. Jeff said to me "I know what that is. It's your orgasm...I can do it sometimes too".  I was floored. I thought to myself, "how could he know about this feeling and never tell me!"  He told me that it only happened when he was real horny and he said he described it as when "you make it feel so good it hurts, then you have to stop". That's exactly what I felt and now I understood what this orgasm was.     Jeff told me the sensitivity would go away in a few minutes and he went back to his make-out with his pillow.  And I just laid on his floor in amazement as to what just happened. My eredtion was starting to go down but I was still in this state of bliss and bewilderment.  I remember eventually Jeff turned over into his back with his penis sticking straight out of his boxers. His technique was different than mine as he folded his pillow in half and placed it flat against the tip of his erection, and rubbed the pillow against his head in a circle.  He did this for about 10 seconds before he panted under his breath "orgasm, orgasm, orgasm, whoo whoo orgasm!  And with that I saw Jeff have his orgasm.  I don't remember anything coming out but I remember distinctly his back spasming and the telltale sign of that post-orgasm oversensitivity as he delicately slowed the pillows circles against the top of his arrow-straight hardon.    Jeff started to laugh and we looked at each other.  He knew what I had felt and I remember making some sort of joke about how he never told me about that feeling when we'd had our pillow make-outs before. Nothing more happened that night. We laid there a few feet apart, erections eventually recoiling and our cocks returning to their normal states where we could put them back into our boxers without strain or tenting.  We eventually drifted off to sleep without much more to talk about here   He and I had many of these sessions and I may tell more of these stories here.  But this was the true story of my first orgasm.