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I was 13, she was 17 and one of my brother’s best friends. I thought I was so lucky for even catching her eye. She played soccer and always came over in her dirty uniform. She also had tattoos everywhere, which I’m confused about to this day since she was so young. She was very gay and open, and I was shy and unsure about sex. She was gentle with me and taught me the way around a woman’s body. I thought it was serious, because, well I was 13 and in love, she thought it was just sex. She died in a car crash right outside my neighborhood after I was seeing her for a couple months. I still think about her.
Oh, Dalton. I have always been the funny, chubby, social butterfly that is every straight man’s wingman. And thats how it was with Dalton. We were young, 13 or 14, and best friends. I got him dates and three-way called him every day after school with his girlfriend on the line. He was athletic and very popular, we had sex in his theatre room one afternoon accidentally. It was my first time with a boy, but I didn’t make it a big deal. He was kind, but it ended quickly. I slept with him through high school randomly when I was horny and in between girlfriends. He didn’t mind. It was easy.
Girl with green hair
After Suzie passed, I wanted to stay emotionally unconnected so I had sex with lots of randos. I was in a Panera with my mother and there was a girl with green hair and glasses doing homework in the lobby. I followed her to the bathroom as my mother waited at our table, it was quick, and we didn’t speak to each other at all while she dropped her pants in the stall. I remember she licked my fingers after I pulled them out of her. I don’t know her name.
She was my sister’s babysitter, and technically mine also, but I was 14. And she was 16. We were playing hide-and-seek with my little sister and I let her touch me in the closet while my sister was downstairs searching for us. She never babysat again.
We dated most of freshman year. I met her on Myspace. She went to a Catholic school just like me and was extremely smart and adorable. 5’1 with braces and short hair, always wearing dickies and a bandana. Our first conversation was about my favorite band and she wrote me beautiful poetry. The sex was rough and random, she was far more experienced than me. She was the one who actually popped my cherry. Yup, it took that long. I came out to my parents while with her.
She was in my choir class and was a junior when I was a freshman. She was drama city and kinda dirty looking. She was a straight girl with a boyfriend. We hung out one night with a car full of people, and while they ran into the store, we stayed in the vehicle and fucked. I did all of the work of course. We “dated” for a bit while she still continued her relationship with her boyfriend. We traveled to Ireland together for choir and had sex on the plane.
I met Lyndsey at my high school, she was a year older than me, and was the only openly out person at my school, not by her choosing. She was caught making out with a girl on her softball team in a linen closest. She was naturally gorgeous and had a smile that lit up the room. We were in band together and started carpooling to school. Her parents were crazy when it came to her sexuality, which eventually split us up. While we dated, we had sex everywhere. Cars, basements, graveyards, parks, friend’s beds, public pools, restrooms at school. We didn’t waste any time. She made me really nervous cause I knew she was such a catch. She still is.
She was my best friend’s brand new girlfriend and we had plans to meet at my house then all go to the mall one winter night. My best friend bailed at the last minute when Shannon was pulling into the driveway. It was snowing and my dad didn’t want her to drive home, so she stayed. I had only met her in the hallways at school before then. She was short, blonde, skinny, and cute. Very vanilla and insecure. Just a fragile, good girl. We had sex that first night for probably six hours. She was in love with the way I touched her. She cried and told me she loved me that night. I told my best friend the next day and Shannon and I ended up dating for 3 years on and off again. My first true, long love. She’s happily engaged now and we still talk once a year or so.
I went to grade school with him. He was friends with Dalton. He was a virgin. Shannon and I invited him into our bed. He was thrilled, of course. Two girls for your first time? Pure bliss.
A guy I met at youth group, I brought him home with me one day and gave him a hand job cause he asked. We tried to have sex but he couldn’t stay hard and I was dry. Then I asked him to leave.
While Shannon and I were “off,” I met Danni from Shannon’s softball team. She was very tall and awkward and her mother was the cafeteria lady at the school. I think I dated her out of boredom. The sex was clumsy and bad and one-sided. The first time we tried to have sex she cried for at least 4 hours because she was scared I was going to hurt her. I lost interest quickly.
I met her through a mutual friend and she was a huge pothead. She was under 5 foot and chubby with rosy cheeks and a really high pitched voice. She wore crocs and gym shorts always. But I had the biggest crush on her, she was adorable and real and was an amazing baker and blunt roller. We had sex a couple times. Usually at 3 in the morning when she called and I would sneak out before she woke up.
The ultimate challenge. She was a beautiful, red-headed, perfectly curvy honors student that would be any parents’ dream daughter-in-law. And she was so in the closest. She was a textbook catch. We were really good friends for a long time, we went to high school together. She would show up at my house at least once a week without telling me and we would sit and talk in her car for hours. One night, she invited me over to hang out and I ended up spending the night. I kissed her on the couch in her parents’ basement. Her lips were like gold. A prize I had worked so hard to claim, and damn, it was worth it.
I met her at a gay club in St. Louis. She was a blonde bombshell knock out in a tight black dress and heels. And was terribly drunk. I met her on the dance floor, I was all over her body and she was into it. We drunkenly made out and she asked for my number. Turns out, she went to the same college as me and we dated for a couple months. The sex was weird and offbeat always, and no one ended satisfied. But she had a great ass.
She lived in the same dorm as me and we had the same friend group. She was known for sleeping around with boys, and cornered me one drunken night about her experience with a girl in the past. She took my hand and guided me to a study room full of windows, in the dorms. I pulled her pants down and pushed her against the window. It was rushed and messy. My phone rang and I walked out and left her there to take the call.
One of my best friends in high school and throughout college. She was hilarious, crazy, and had skin that glowed, smelled like coconuts, and felt like a baby’s bottom. We had sleepovers often and would always cuddle. One night, it turned into more. It was soft and slow and very casual. It happened often for months, but it never changed our friendship until my girlfriend found out I was sleeping with Keeks while with her. Sometimes even in the same room as her. I just didn’t view it as cheating cause I had no emotional feelings for her besides friendship.
Sarah had a crush on me for a long time and I definitely dragged her along and made her wait a while to get with me. She was as social as I, highly likable, and the sweetest soul I’ve ever met, but the physical attraction was never there for me. I eventually fell in love with her after almost a year and decided it was time to give her a chance and get physical. She was the only person I was ever with that met my sex drive. We had sex every night and were really connected. I taught her about her body and she let me do whatever I wanted to her. But, I was an asshole and cheated on her with Keeks, so eventually it ended in disaster.
We met on OkCupid. I was out of her league lookswise, but she could always keep a conversation. We hung out briefly and slept together once when we were drunk. She had serious body dysmorphia so I tried to make sure to treat her with care.
We also met on OkCupid. I must have a thing for straight red-headed girls. She was so intrigued by my sexuality and confidence, and after being very persistent, she took me home from the bar on the second date. Her house was trashed, smelled like dog pee, and she bit me everywhere while we were having sex. Not playful biting, hurtful biting. I was covered in bruises for weeks and never spoke to her again.
We met on Tumblr soon after Sarah and I broke up. I was looking for extra attention because I felt bad about the break up. We messaged on Tumblr, Facebooked, Skyped, talked on the phone, and met all in the same week. She lived 4 hours away. We had sex the second night I met her. She was the perfect blend of submissive and dominant. Sex was the only thing we ever got right. She was the first person I was with to get me off, and I craved it. It was the fix to all our problems. But the drama was too much eventually. After over 2 years, we called it quits.
Mal & Kynslie
We were college friends and these two ladies had been together forever. I had always been very into the mysterious Mal and she looked beautiful smoking a cigarette. Kynslie was just an added bonus. They brought me home from a house party when I was blacked out. I remember lots of skin on skin, wetness, and waking up in between them with no clothes on. I remember Kynslie and I having amazing chemistry that I was surprised by. I escaped in the morning before they woke up.
She was a music major that I met on OkCupid. She had a busy schedule and was still unsure about her sexuality. She was accommodating, sweet, but needy. She would come over every couple weeks and we would make out, and eventually we had sex. I was fully clothed, she wouldn’t let me undress her, but still wanted me to touch her everywhere. I felt like I was hurting her and spent the entire time checking in with her to make sure she was okay, rather than enjoying myself. I distanced myself from her after.