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Losing my virginity was probably an exceptionally calculated move on the part of my 17-year-old self. I'd been told by family to wait for true love, and told by everyone else to wait until I was ready. I knew he was in love with me. Unfortunately, even though I tried, I was not in love with him.
It didn't really hurt, more like a paper cut some one had rubbed lemon juice on, in my junk. He was average in size and relatively gentle. It mostly sucked. All in all, it was exactly what I expected.
He had a voice like syrup and he liked pouring that voice in my ear allll night. He was black and fixated on my white black-girl-booty. My bubble ass fascinated him. We had my first introduction to good sex a few times when we were between projects. Nothing concrete ever bloomed because we were just…busy having sex.
I had sex with a disabled person. That's not usually on a person's bucket list. He was pretty big considering how skinny he was, but we had a big mental connection and spent a long time talking. He revealed he was a virgin, not for lack of trying, and I saw that as an opportunity to enlighten him. The following two-year relationship ended horribly and the mediocre sex branded a virgin-aversion into my brain forever.
We were girlfriends for a bit, mostly drunk. We would get wasted on gin and go bar hopping, pretending to be gay, maybe wanting something else. One night we were in her apartment and she dropped a bottle of Jagermeister drunkenly off her 23rd floor apartment balcony onto a busy Vancouver street below. Thankfully, it was 3 in the morning so no one was injured. I got mad at her for endangering some one's life and we wound up sparring over her kitchen island, clearly inebriated. She sprayed me with the hose from the tap for some reason, so I tossed a cup of white wine on her. Somehow, we wound up having sex in a puddle of wine and water on the marble tiling in her kitchen. It was then that I confirmed that while I wasn't opposed to it and she said I was decent at it, blow jobs were more my style.
Everything with Matt was like being on fire. We had the same birthday, one year apart and were basically identical in every way except that he has a penis. We bonded over our mutual boner for cars. I wound up having sex with him parked behind a Safeway in a company truck. He was beautiful. His body was naturally muscular and tanned and he looked like Brad Pitt naked. He had a weird dick though, thick at the bottom and narrowing a lot toward the tip. In the dark, my brain assigned it the same shape as a pylon. Naturally, we burned out fast and we were only fuck buddies for about a month before we both got sucked into different jobs.
This was the first girl I met that I wanted to have sex with immediately. She was a glamazon and pure sex, all long golden legs and shiny golden hair. She even had this exotic streak of dark red running through her hair that she claimed was natural. She was dating a guy one of my friends was friends with and they were late to a party. She sat beside me at the table and I struck up a conversation about girly drinks (we both just wanted a beer). Talking to her mesmerized me, I just liked watching the way her mouth moved and how she laughed and cushioned her glass with the tip of her tongue when she took a sip. I thought it was just me until we went to the bathroom together and she dragged me into the handicap stall with her. Even better was that she preferred going down on me. We stuck together the rest of the night and endured everyone's remarks about how we were getting along so well.
He was a rich hairless hockey player with an ass so rock hard you could bounce things bigger than quarters off it. I met him while I was working and he came back to my workplace to ask me out. Facially, I thought he was 'meh', but I appreciate men going out of their way to ask women out so I agreed. He was the perfect balance of yays and nays; He had the body of a god, face of an average dude. Libido of a rabbit, penis the size of a child's. The penis size did not deter him from fucking me so hard I couldn't sit properly, which I wish was an exaggeration. We had a good time together until I discovered he liked having me on his arm and 'dating' me, but also had a fun time schtupping everyone else when I wasn't around. He cried when we broke up, tried to get me to stay. I did wind up getting wasted two months later and running into him. We wound up having epic and hot drunk sex and a vicious fight in the morning. Perfect balance of yays and nays.
I guess Connor and Sacha overlap. Sacha was Connor's best friend, an exotic looking guy with dark features and bright green eyes. We got along because he was smart and easygoing, a stark contrast to Connor's uptight and suspicious way of operating. We had drinks at a bar together a few times. He came over to Connor's one evening and we were all having a great time talking while Connor cooked. Sacha then started complimenting me and touching my neck and asking Connor questions like, "How can you not constantly kiss such a beautiful woman?". Oh my.
When he did kiss me, I was totally drunk because I was starving before we'd even started cooking and I expected some shit to go down. Instead, I wound up having a reasonably wonderful double-penetration-less threesome with two guys. Sacha was tall and lanky where Connor was short and muscular. Sacha's dick was bigger, and basically perfect save for the slight curve to the left, so he wound up having sex with me while Connor got the oral end of the stick. It only occurred to me after my relationship with Connor ended that he and Sacha probably tag teamed girls all the time with that set up. Unfortunately, I didn't hate being all kinds of touched by two different guys so I didn't care that much.
I was wasted, dressed like a "slutty superhero" on Halloween with a bunch of my wasted friends. He was dressed in a form fitting Green Lantern outfit which accented his ridiculous pecs perfectly. I remember asking him what he did, and he said he was in the armed forces. I made a joke about responding to the call of duty and we wound up fucking against a wall in a back alley. I was so drunk I mostly remember looking up at the sky and thinking: "Green Lantern would never fuck Black Widow."
I only know his name because I remembered to ask it before I slipped back in the club.
I was single for a long time after the Connor debacle, fishtailing out of control because I had convinced myself I was ugly and he was there for me during it. I might be, I have no idea, but I'd never thought of myself as ugly before then. He was technically with another woman that I hated when we had a massive fight and I confessed my feelings for him. We didn't talk for two months after that before he randomly started texting me. He never full on admitted to dating the other woman because he knew I hated her so much, so I let myself violate my never-being-the-other-woman rule as long as it stayed in text. Plausible deniability. We exchanged steamier and steamier texts until one day he admitted to dating her and informed me he'd broken it off with her. The split was 'mutual'. I think we lasted a week after that before we gave up and got together. He's the best sex I've had, creative and interesting and kinky. If we get drunk together we always wind up having the freakiest sex and loving it. He was not a fan of blow jobs when we started dating. Years later, he's definitely a fan of blow jobs and the sex hasn't gotten any less exciting.