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I consider myself a late bloomer in a city where a lot of the girls I was in school with were pregnant by 16. Being slightly prudish meant I was sort of naive about a lot of things and finding myself alone in a room with an older guy I desperately liked led to the first (of many) confusing sexual experiences. I told him it was my first time, he suggested I take the reigns and guide him so as not to hurt me. I don’t remember much except my ruined zebra striped bikini bottom.
I was working in retail at 19 and having just started having sex, I was looking for my next conquest. I was bold and flirty with a Loss Prevention officer at my store. He was beautiful and I think not entirely aware of how young I was. I’d drive forty minutes on the weekends to meet at his apartment on the other side of the world. He liked it when I was on top, and he loved to do it with clothes on sometimes. I’d never learn much else about him. He was obsessed with anal, and I was very closed to the idea.
Danny (A different one)
My first serious boyfriend. I write this and am smiling because it was all very innocent. He was such a beautiful man, both inside and out, but I cannot remember ever feeling a strong desire for him physically. I never wanted to have sex with him. In our year long relationship, we had sex a handful of times. Strictly missionary. Never unprotected.
We’d been friends for years. In fact, he was my first crush in middle school, where I was staggeringly overweight and nearly invisible to the male species. After growing into my body (and shedding baby weight) I was a new girl in Doug’s eyes. I kissed him while trying to set him up with my best friend, after spending the night with my then boyfriend Danny. I dumped Danny the next day and spent that night at Doug’s mom’s empty house running around naked as we fucked on every surface we could find. This is when I realized that sex could be ridiculously hot. This was my first “multiple night sleep over” situation with a man and would forever make me abhor the act of actually sleeping with someone.
Mack and I “dated” in high school for a few weeks. He’d write songs about me, most of them hateful. After high school, his band blew up and he went on a world-wide tour (being featured in Rolling Stone at one point.) Upon his return he found himself dealing with an addiction, a fading fame, and a quickly deflating bank account. Above all else we were friends. I’d spend time at his house, consoling, listening, reveling in his tour stories. One night he proclaimed he needed sex. It was awkward and passionless and my mind was elsewhere for the entirety of the act. I kissed him goodbye and we’ve been great friends with no sexual spark since. He’s completely sober now.
I have a very sexually progressive friend who said I needed to hang with her before leaving home and moving to NY for good. I remember getting dressed with the knowledge that I’d probably be getting laid that night. I showed up to her house to meet up with her, her boyfriend (now husband), and their ridiculously attractive friend Brandon. We went to lunch and drank like fish, laughing like old friends and sharing long glances over tuna tartare at three in the afternoon when I was still well underage. We went back to their house and my friend proceeded to get naked. I’m not one to turn down fun, so I did too. Brandon was gentle and kind, but so much fun. I look fondly on that day as the day I began owning my sexuality. I’ve never been one to just agree to sex since that moment.
Oh man. Theatre school in New York City can be a doozy! Constantly surrounded my attractive, talented, physically fit people who are all 19-25? It’s a wonder I wasn’t more promiscuous during these formative years. There was this very talented, funny, and seemingly cool guy named Chris. I think two weeks into our first semester he crawled into my single dorm room late at night and kissed me like the world was ending. The sex was disappointing. His behavior afterward was maddening and mine was absolutely atrocious. I littered his room in post-its about how mad I was that he told everyone. I did mention this was theatre school, right?
Remember those confusing sexual experiences I referenced earlier? Cue Andrew. Met him at a giant NYC club on my 21st birthday. I was too drunk to walk down the giant staircase and this completely sober Andrew helped my friend Carmen drag me into a cab outside the club. He asked for my number, she gave it to him. I mean, I should’ve known it would be weird, he hit on me while I was so drunk I could barely say my own name! We slept together for a year. Most of the experiences were strange and scary and bizarre. There was one night he was so drunk I thought I’d die while he drove down the BQE. There were various days where we’d have to sneak into his basement apartment at his parent’s house. Where we’d wake up shivering and he’d have to go spend the morning with his family before making up some excuse for taking his car somewhere so he could drive me from Ronkonkoma to the Upper West Side.
Cool kid from high school who moved to Connecticut, which was the closest connection to my hometown I had in this lonely city. And those first few years are so very lonely. He came to pick me up from Manhattan, we drove to Connecticut. I saw my first snow fall that night and he filmed and edited a rather beautiful video of me running around enjoying myself. We got high as hell on medical marijiuana, watched Zeitgeist and had very rough sex in his loft apartment. He drove me back the next day. He’s recently become a Buddhist, but we still remain great friends on the social medias.
I was on Facebook one night, and I saw a picture of a cute boy from my hometown. We had 54 friends in common, surely we knew each other! So I added him. So began our year and a half long distance relationship. I went back home for a break and met him face to face for the first time. It was lovely, and I really did love him. We had great sex for the very few times we got to see each other over the year. He helped me open up sexually in a way I hadn’t before. I felt beautiful being naked with him, I wanted more every time. We broke up when I met a man in real life NY that made me think I could feel this way with him.
There isn’t enough room on the server to write about my relationship with Bryan. When it was good, it was great. In retrospect, the sex was always a bit removed, a bit detached. I remember thinking that he didn’t know the difference between fucking and making love. And sometimes I wanted to be his whore and sometimes I wanted him to tell me how desperately he loved me. It would become evident after two years of sleeping beside each other every night that we were terrible for each other. Maybe it was less about knowing the difference and more that he never actually loved me, nor I him.
Before the break up with Bryan, he confided in me that one of his biggest fantasies was to be a bit of a cuckolded boyfriend. He wanted me to sleep with another man and relive every detail to him while denying him pleasure. We were so far gone, I was so lonely in this relationship, I needed something new, so I agreed. I met Aaron at a bar where my best friend was tending. We slept together the night before I kicked Bryan out. I told him everything. He was a terrible lover then. Once Bryan and I broke up and I got back from Florida, we continued sleeping together for months and the sex kept improving, but I knew so little about him. I’d get entirely too attached, he’d try to ease out of my life without hurting me.
Irish bar manager at an Irish bar I frequented in Cooper Square. I no longer find Irish accents alluring.
Friends through the entire Bryan relationship. Had one very hot make out session while Bryan and I were together (that I told Bryan about and we worked through). He’d cook me dinner, talk about taking me on expensive trips, ask me to help him shop at Bloomingdale’s for his Ferragamo shoes. He was a lawyer with lovely hands, and a misogynistic streak that I could only laugh at. I mean, he had to be joking! He had a problem with intercourse, he never lasted very long. He hated that I liked sex a little rough, but he began coming around to the idea. He listened to my problems, and tried to help in any way he could. I sent him a text on my 25th birthday that said I maybe needed to cool it, because I loved him more than I thought I should. We haven’t seen each other since, both of us making excuses. It’s a shame, we were great friends.
Smart, funny man. We get on really well and can tolerate each other when completely wasted. We’ve slept together a handful of times, each time more drunk than the last. He refused to wear a condom once and I stormed out of his apartment, grateful to have not slept with him. Needless to say, we’re no longer sleeping together, but will occasionally go out to dinner and events together.
OkCupid date. I’d never hated someone upon first meeting them, until I met Brandon. He asked me when my last STD check up was. I went back to his apartment in the Financial District and had amazing hate-sex with this guy. I don’t remember what he looks like. I sent him a report of my clean records the next morning after seeing his the night before.
I’ve been sitting here for twenty minutes thinking of how to begin the Tom saga. Tom was a 40-year-old professor at a prestigious university. Tom had an 18-year-old son, that I’d meet and be frightened by when I realized that I related so much more to the young man beside me than the man I’d been sleeping with for months. Tom was kind, but very lost, he was almost childlike. Tom was fun in a way I can’t describe. We were relaxed with each other and I think that made it easy for him to fall in “love” with me. Tom scared me like no one ever has. He didn’t know how to let it go. He continued e-mailing for months after I ended things until recently where I sent him a strongly worded and painful to write e-mail asking that he stop all correspondence. Tom was my neighbor, I still see his mail in our mail room.
He saved my best friend’s dog in a heroic and selfless way that left him with bruises and scrapes. It was all I could do to keep from attacking him with love right then and there, so I waited a few hours.
Picked him up at a bar. He was lovely at first. I caught him videotaping me from behind a few weeks in. I’ve deleted them, and through some serious talks, we’re on the mend. I’ll never sleep with him again, but he seems to need a friend in this weirdo neighborhood.
Jim is the kind of man every woman should meet in life. He’s a gentleman who makes you feel beautiful, delicate, lovely, hot, and fucking powerful in a single glance. He’s mysterious and open with his feelings, he’s a beautiful guitarist. He’s in an open relationship with a beautiful woman (more on her later). Jim took the time to get to know me before inviting me to his home. I mean, nine months worth of courting in the way of coming in to my restaurant and sitting with me for breakfast every Tuesday. We’d talk about family and love and life and music. We’d talk about living in the coolest neighborhood in the world. I fell for Jim in these talks, I never expected to fall for him again behind the curtains in his airy loft apartment. He was a patient lover. He’d go down on me for hours, he’d explore my body with a respect and admiration that I’ve never felt before. I worshipped him.
Jim and Kat
Kat was the birthday girl the night Jack kissed me by the bathroom door. Kat is Jim’s partner. She is beautiful and smart, funny and quick to laugh. I love her laugh. The night it happened, we spent a lovely day together, walking through Brooklyn in the snow to a show in Williamsburg where we all slow danced and drank and kissed. It was beautiful in that way 20-somethings find progressive relationships appealing, yes. But also in a very real, very centered way. We genuinely cared for each other. The sex that followed was life changing. During it all, I felt cared for and like I could care for others without being judged or without “feeling too much.” I want to roll my eyes at myself as I type this, but I do love these people, and I love how they make me feel. Beautiful and strong and like I’m worthy of love.