It was with the driving instructor's son. Driving lessons got a little awkward after that.
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Mr. First Man: aka the Virginity Bandit:
I was 16, he was 17. He was hot, older, and all my friends wanted to hook up with him. He was a friend of a friend and we were at a party. I had just broken up with my first ever boyfriend and was really drunk. We played beer pong and flirted all night. The night gets pretty blurry after that, but I remember fumbling with our clothes, rolling around on a cold basement floor and three thrusts. I remember not feeling like anything was different and explaining to all my virgin friends what a let down sex was.
Mr. Boy Man: aka the First Real Sex and then some:
After that, I was sure sex was not for me. My boyfriend and I ended up getting back together and he really wanted our first time to be special. Unable to tell him it wasn't going to be special after everything I had previously experienced, I pretended to be really excited. Instead of special, we got drunk at a party he had at his parent's house while they were out. After a few tall cans of BUSCH beer (a high school favorite of all the cool, hockey boys) we ended up fooling around. It led to sex in his older brother's bed. This time it hurt, and I remember fighting back tears. It was definitely more than three thrusts and I definitely felt different. We cuddled for a bit after and then got dressed and waited for my parents to come pick me up. He texted me after saying he loved me. It was pretty cute, considering I was 16 and he was my first boyfriend. I wouldn't say the sex was good, but it did leave me more hope for better sex to come.
We broke up a few months later and never quite mastered good sex, until we ran into each other a year later after graduating high school at a party. We ended up sneaking off to the bathroom at the party to "catch up". We ended up catching up quite well and quite a few times. We even ended up going back to my place and spending the night and the next day together. We almost got back together, but for the better, the only reconnecting we did was a couple drunken nights and not another roller coaster relationship.
Mr. Joke Man: aka the Driving Instructor's Son:
I had sex with my driving instructor;s son. It was painfully awkward and I remember just wanting it to end. It was in his basement after we had gone out for ice cream. We were watching My Super Ex Girlfriend, a movie he chose because he "liked the story line". More embarrassing than his choice in movies, was his cheesy lines to try and make me more comfortable. The sex itself lasted a whole of five minutes, and reminded me of my awkward first time. I had to pretend it was great. Driving lessons got a little awkward after that.
Mr. Man Crush: aka The Acquired:
In grade 12, my friends and I hung out with guys a couple years older who were all in college and working. One of them was the most attractive, nicest, and funniest guy I had ever met. I had a huge crush on him. He was dating this girl who used to hang around at parties, so he was off limits. By the end of grade 12, they had broken up. He came to our after prom party and we had a really hot drunken hookup against the wall of one of the cottages we were renting. We also fooled around on the beach that night. Unfortunately, we did not sleep together. I moved away to college and we kept in touch. I'd come home and we'd see each other at parties or run into each other, and would always end up making out but it never led to sex.
I was moving back to school in four days. It was Wednesday aka Dollar Beer Night at the local bar. I was drunk and feeling myself a little bit more than usual. I texted him to come meet us at the bar. By the time he and his friends got there, I had taken full advantage of $1 draft beers. Within 20 minutes of seeing him, we were in a cab and on our way to his house. We had sex a few times and it was better than any sex I'd had before. Probably because it was so anticipated and I'd been dreaming about this day since high school. He even called for my cab and paid for it. I felt like a princess.
I guess we continued to see each other, feelings ensued, and if you ask him, we ended up dating. Though the label was never agreed upon or official. And so began an on-and-off and on-and-off roller coaster of a relationship for the next two years.
Mr. Varsity Man 1: aka Big Mouth on Campus:
I had casually made out and fooled around with a guy on the varsity baseball team in first year. After moving back to school for second year, we occasionally still ran into each other and continued our make out, fingering, and blow job relationship. Until one night in November, I was really bored after handing in an assignment. He texted me to come over and even though we'd never hung out sober and I knew it was a booty call, I went over. We got really high with his roommates and then fucked. It was awful and awkward and I regretted it the minute we were alone in his room. I didn't finish (typical) and after about 45 minutes of abuse on my vagina, I told him I had to go. A few weeks later, everyone knew because did I mention, he went to my high school? Oh, and even better, he told everyone we made a sex tape and sent around fake pictures of my boobs. He was a real winner.
Mr. Varsity Man 2: aka Walk with a Limp:
My friend and I went to the campus pub one night and got wasted. We met these guys from the football team. Of course, I love football and team spirit and he looked like Nathan Scott. He was super cocky and that made him even more attractive. We went back to their place and got high, then went back to my residence and fucked. He had the biggest penis I have ever seen. His friend kept yelling, "Switch," I'm assuming because he wanted to switch partners? We all hung out the four of us and talked the whole night. In the morning, they offered to write a stats test for us, we declined, and they left. I was in so much pain, that I apparently walked with a limp… the guys on my floor made fun of me for it for a good two weeks.
Mr. Tinder Man: Aka that Black Guy from Tinder:
I downloaded the dating app for iPhones and went on a blind date with a guy from it. He was black and beautiful. We went out for a few beers and then parted ways. It had been super boring. I ended up getting really drunk with my friends and bootycalling him later. He came over and we had sex for a good couple hours. It was decent, but boring. He slept over, and we had sex sober in the morning. It was awful. He left and I deleted his number.
Mr. Drug Man: aka Summer Love:
I went through a period my friends and I call a "drug haze," where I spent more time high and drunk than I did sober. This was mainly thanks to a guy I thought I was in love with. He was beautiful, buff, and a bad boy. He was a dealer, funny, charming, and made me feel beautiful. He slept over at the beginning of June and he just never left. I guess the fact that he had no where else to go never really crossed my mind, because in my mind, he had chosen to spend all his time with me. Though the relationship was rocky at best, the sex was good and we were having all the fun. A memorable moment for me, however, and maybe a turning point in the relationship, was the time he cried during sex and we had to stop. I think that's when things got more real than fun.
After that, the sex was less and less constant and he began to play head games and hurt me more and more emotionally. This was also around the time he started sleeping with a bunch of other girls and basically using me because I was attached.
Mr. Radish Man: aka Who?:
My guy friends always joke about how big my boobs are. They call them my personality. As in, "I noticed your personality when you walked in the room." At a going away party for the boy I was in love with this summer, a guy came up to me and told me I had a great personality. He was obviously referring to my boobs, and I thought it was hilarious. We got super drunk and ended up fooling around in my friend's bathroom. We had sex for 2.5 seconds except I couldn't feel anything and it was awkward. I told him I needed a glass of water and went upstairs and never came back. We are pretty sure he went nuts and trashed the bathroom. I don't actually remember his name, but he had a radish tattoo on his arm. That's cool I guess.
Mr. DJ Man: aka Backdoorman:
My friend is a local DJ. He plays at clubs in the city. After a wild drunken adventure with our group of friends, we got drunk and I ended up heading back to his place. Surprisingly, the sex was pretty good. Until he walked upstairs drunkenly after and told a room filled of our friends we had butt sex. Which we didn't. I guess he regrets that because everyone brings it up to this day.
Mr. Best Man: aka My Best Friend:
Everyone says sleeping with your best friend is a mistake and I would have agreed with them a couple months ago. One of my guy friends is super buff and fit and used to be a stripper. I'd always joked that if we weren't so close, I would do anything to sleep with him. After a month of awkward fighting and hating each other beccause of a slip of the tongue, we had really awful awkward sex during which I cried and asked him to stop.
This led to another couple weeks of not talking. Finally, we made up and were back to the closeness we had before. One day after getting really baked, we were sitting talking about nothing and he went to the bathroom and sent me a Snap Chat of his penis. To anyone else, that probably sounds awful, but it's just very us. I went downstairs to my bedroom and sent him a picture in reply, one thing led to another, and we ended up having really hot aggressive sex. That weekend, we got drunk and it happened again, but this time more aggressive. Believe me, I had the bruises to prove it. We ended up being best friends with benefits and it was the perfect arrangement. Because of everything we'd been through, we could be completely honest with each other, and tell each other exactly what we wanted and how we wanted it. We also high-five after sex, which is really cool. This was really good, but the friendship was better!