I think it mostly had to do with the fact that sex was a thing you did with "friends", and I did not have friends, so I equated it with people I did not enjoy or respect; and therefore it appeared unenjoyable and disrespectful. Terrible teenaged logic, but it's how I felt.
None the less, organically I'm an extremely sexual girl and before I discovered sex, I had spontaneous orgasms probably once every week or so, maybe more. I imagine it was just like what boys experience when they're going through puberty with preteen erections and wet dreams and such; awkward and confusing and unavoidable and exciting and shameful... And delightful. Still, I never even touched myself.
People in my school bullied me constantly about being ugly and uncool, and so I figured sex was not a thing I would ever have to worry about, anyway. Instead I spent most of my time worrying about online chat roleplay games, dragons (I fuckin loved dragons), and the video games I played nonstop in my basement everyday after school.
When I became a sophomore in high school I somehow managed to score a boyfriend- a really hot boyfriend, too. He was three years older than me and was new to our high school- a second year senior after being kicked out of military school. He didn't have the preconceived dislike of me that the rest of my school had and so was able to see that, in fact, I was neither ugly nor gross (and my uncoolness was apparently very cool to him.)
He told me he decided to ask me out after he saw a girl dump water on me, and watched me respond by chasing her down with a stick.
He had an eyebrow piercing and a car. As a teenager these things are basically like gold. He had pitch black hair, thin eyes and big juicy lips. He was very dark skinned naturally and even darker in the summer- watching him take off his watchband was a delightful lesson in tanlines, not a thing I had ever personally experienced, being so pale myself that my skin is practically translucent. He was- is- the only Jewish guy I've ever dated, much to my mother's chagrin. Oh well. Let's call him Ben. His name obviously was not Ben.
My mom and Ben got along famously, and when we started dating she turned to me and said "he'll be a great fuckbuddy until you go to college." She was right, of course, but it was still very embarrassing.
Ben was a perfect first boyfriend. He loved video games and swords and fantasy just as much as I did. He did not balk at my monstrous stuffed animal collection and he loved that I loved metal (even though he was more of a jam band guy.) He was understanding of my initial aversion to sex and walked through the bases with me slowly and respectfully. He started giving me head months before I felt comfortable with the idea of putting a dick in my mouth and never made me feel shitty about it or complained about unfairness.
His penis was a perfectly average size with a slight upwards curve. The bottom half of his shaft was the same color as the rest of him but the top half looked like it had been frankensteined on from a black person. He let me draw faces on it, and do this thing when it was flaccid where I would turn it inside out inside his body, cover it with his balls, and then release it and watch it slowly pop out again like a car coming out of a garage. This is apparently a very easy way to entertain a fifteen year old girl, in case you were looking for one (don't do that, by the way, unless you also happen to be a teenaged person.) After his cock and I had finally gotten acquainted, I could not keep my hands off of it.
The first time I ever touched his dick- my first of many future dicks- there was actually another girl in the room. She was trying to initiate a threesome but, I mean, she was clearly barking up the wrong forest. We were all in bed watching tv together. She started snoring, so we gave each other a look... He pulled his dick out from his pants zipper under the covers- I'd never even seen it before, and I didn't look then. I nodded consent at him, and he pulled my hand towards it. Trembling, I took it between my thumb and forefinger in the kind of way you might hold a plastic baggie containing a dead mouse; with both fear and unfathomable gingerness, as though it would break under the slightest pressure. I couldn't breath. It was so weird!
The other girl woke up and got up to go to the bathroom, and as soon as she was out of earshot he gave me an amused smile and said "look, you're not gonna hurt it." I exhaled, wrapped my hand around its flesh and fell in love.
That June he was kicked out of his parent's house and lived in my basement. We spent every waking moment together. He was leaving the state for college in the fall- I thought for sure that would be the end of it. I fell stupidly in love and so did he.
By the time my birthday rolled around in late August, I knew I wanted to lose my virginity to him. I meditated on it the whole week beforehand, getting my courage up to tell him to make love to me.
My birthday was less than a month before Ben had to leave for school. I was ready, and had a smile on my face all day in expectation. At dinnertime, my parents took us and my family out for birthday tacos, buy right after we placed our order I started to feel like death.
Dinner was a blur- I could not force myself to eat even a single bite of my food. My father screamed at me in the restaurant, claiming I was being a spoiled brat for some reason or another. My eyes welled up with tears as I swore I wasn't trying to be a problem, I just couldn't physicallh eat.
We returned home to find I had a fever of 102 degrees. I cursed my father out and ran to the basement with Ben behind me. He held me and calmed me down, and even though I felt sick we began to kiss. Heart pounding, I sucked his cock until he was hard, then mounted him and started rubbing my pussy on his erection.
"Stop," he breathed. "We have to stop right now or I won't be able to stop."
"So let's not stop."
"I...really? Are you sure?"
I pulled out a condom I had hid among the basement couch cushions and handed it to him. He slid it on, and then...
We just couldn't get him inside of me. The pain was monumental. My body being already weak from the fever, I couldn't hide the shock and gasped for air.
He stood up with haste, looking like a man who'd just accidentally shot someone. "It's okay," he said. "We don't have to do this now."
My mom called us to the kitchen eventually- my dad apologized and I opened presents, mechanically, completely uninterested. I watched other people eat cake. I frowned and said I wanted to go lay down.
Ben and I went upstairs to my parents bedroom to watch tv and snuggle. I was not put off by our earlier failure- I pushed, and I played, and eventually..
"Stop," he breathed, "we have to stop right now or else..."
"I don't want to stop. All I want for my stupid birthday is to have sex with you before you have to leave me."
When he climbed on top of me again I wrapped my whole body around him and pulled him hard, against our uncertainty, deep inside of me.
The pain burst like an explosion and shattered into waves of pleasure unlike anything I'd ever felt, or would ever feel again.
Despite the massive pain I didn't bleed even a little bit, and as soon as it was (unsurprisingly quickly) over we threw our clothes back on and held each other close underneath my parents' comforter- sorry, mom.
The next day I told my mother (mostly- I didn't say it happened in her bed.) She said mazel tov and took me to CVS where she bought me the biggest box of condoms on earth, glaring in defiance at the cashier as she told me, "you should never feel guilty about making sure you're safe. There's nothing shameful about buying condoms." Two weeks later she would take me to her OB/GYN and hold my hand through my first exam, signing me up for a prescription for birth control pills.
After that, Ben and I had sex three or four times a day until he left. We experimented with almost everything kids can think of- roleplay, crazy positions. We did bondage using satin ribbons. I had a riding crop left over from horse riding lessons. We used to fuck constantly while fighting against each other in Super Smash Bros. I never let him touch my butt, though. (True facts: the first sex I had with my next longterm boyfriend, which was several years later, was anal sex. In the woods. In a tree. No lube. Really.)
I thought our relationship was going to end when Ben left for school, but it stupidly didn't. He wanted to try being long distance. He didn't want to break up. I was too naive to disagree.
Ben got kicked out of college after his first semester. At that point, it became obvious that we were not meant for each other, though it took longer for us to acknowledge it. His parents bought a townhouse for him to live in and he sat around there doing nothing except getting high. He became friends with people who made me feel unsafe. He started making me feel bad about my weight (a hefty 118 lbs) and my intelligence (a defensive measure since I'd earned him his only college A by writing one of his papers.) A year later, he started refusing sex and we mutually agreed to break up.
True story- he met another girl two weeks after our split in one of his community college courses, and started dating her immediately. That was ten years ago! They got married, and very recently just had a baby. I'm happy for him; I'll always remember him fondly for being so patient and caring with me when I needed it.
Xo
