The Orgasm Chronicles

(Editor's note 2024 - one of Wesleying's most popular articles ever. As of 2017 it had over 40,000 views. Had to memorialize it on the new site over 10 years later. Maybe we'll even do it again(??))

Spring is definitely in the air and as the end of the semester draws near, some sweet summer lovin’ is in sight! With so many orgasms on the horizon, let’s take a look back through the sexual histories of a few brave Wes students by asking just two simple questions: What is the story of the first time you came? And what is the story of the most recent time you came?

Here, we recount the first and last orgasms of some sexy Wesleyan sharers. All names have been changed to aliases chosen by the interviewee for the sake of privacy.

Lonestar (M)

First time: “So, at the time I wasn’t old enough to like physically come yet but the first time I had an orgasm was when I was probably in fifth grade and had no idea what an orgasm was. I thought that to have a baby all you had to do was to stick your penis in a vagina and it just happened. So, I was having a sleepover with my best friend and we decided to do this thing — at this time I still thought I was straight but I was experimenting a little — so we got water balloons and filled them up and put them on his chest to imitate boobs. It was in a back room upstairs and I got on top of him. We were dry humping a little and pretending he was the girl and I was the guy. I got this really intense feeling all over my body that started in my stomach and just felt crazy and took hold of my entire body and my toes were clenched and I was grabbing on to him and dry humping furiously. He thought he heard my dad so he was like ‘wait, wait, wait… stop, your dad is coming up.’ So I slowed down but the feeling needed to be resolved and I couldn’t stop so I dry humped him until this rush of pleasure and emotion and amazingness came over my entire body. I sat up and then it was his turn.”

Last time: “The last time I came was about twenty minutes ago. I was like ‘Damn, I’m stressed and hungry, I’m gonna masturbate.’ So I decided that would be my little incentive to start work, I would jack off and then start my psych paper.”

Pepper (F)

First time: “The summer before my sophomore year of high school, I went to a summer camp that was held in this huge New England mansion right by the beach. Every night, my camp friends and I would sit out on this huge front porch and stay up late talking and the conversation often turned to sex. I then realized that I never had an orgasm and that a lot of other people had. On the plane back home from camp at the end of the summer, I read a Cosmo article about ladies masturbating so when I got home, I decided to try it. I was really nervous about being caught for some reason so I was really secretive and made this huge deal about needing to take a shower and I waited for my family to leave the house. Then I locked myself in the bathroom and took a bath and made it happen.”

Last time: “This past weekend I visited my boyfriend at his college for his birthday. His roommate has a new girlfriend and they were hanging out together in the room, so my boyfriend and I were oddly sexiled and ended up not getting the chance to have sex the whole day of his birthday. That night, we were at a party in his friend’s dorm room and it was almost midnight and we didn’t want the day to end without him gettin’ some nice birthday love. So as the minutes were passing, I was like ‘I need to make this happen!’ and I pulled him out of the party and into a nearby study lounge and got on top of him and we started kissing. The study lounge has a big window and people kept walking by so we couldn’t do it there and it was almost 12 o’clock and we were like ‘We’re running out of time! We have to do it now!’ so we ran downstairs and went to this single stall bathroom in the dorm’s lobby. It was definitely a countdown to midnight and there was a lot of buildup so as soon as we got in the bathroom we stripped and did it with me sitting on the sink and him standing. So that was the last time I came.”

Frank Berkman (M)

First time: “I don’t remember that clearly, but I think I was about 13 and had just figured out how masturbation works. I was alone in my bathroom. Even though I had already learned about orgasms/ejaculation in sex-ed or whatever and knew what was supposed to happen, I was still sort of freaked out when it happened.”

Last time: “I procrasturbated while writing a paper on Sunday night. It was around 1 a.m. and I was alone in my room. Sorry I don’t have a sexier answer to this one.”

Funk Master Sex (F)

“I was always slow on the sexual uptake, if you will. When I was in elementary school, for a bit I thought sex involved a vagina and an asshole. At the time I was really displeased with that because I thought it was dirty. I have come to learn that isn’t how it is. Anyway, I couldn’t tell you if I have had an orgasm which probably means I haven’t. This one time the summer after my senior year of high school, I was in a hotel room and my mom ditched me because we were in a fight. My friend was going to come to the hotel and have a girls’ night in with me but she couldn’t so basically I was alone in this really ritzy hotel room in New York City. It’s a place where people go to have sex, there are all these couples, like they even have signs by these huge windows that say not to have sex by them. So I was like ‘How am I going to entertain myself?’ and I was looking for the mini-fridge and in a drawer I found this package with a vibrator that had oddly been opened. So I thought if I sanitized it I could use it and subtly slip it back in without having to pay for it, because I didn’t want my parents to see on the bill like ‘Oh, your daughter purchased a vibrator… and oreos.’ But anyway, I decided to use it and it came with this tiny little mirror so that you could situate it and figure that shit out. So I started using it, and I transitioned to the bathtub so there wouldn’t be an echo so no one in the hall could hear me. In the bathroom there was a stereo that had some pre-programmed sex music on it, but that didn’t add any sexiness. I couldn’t say for sure whether I orgasmed or not, but that was probably the closest I’ve ever been.”

Jellybean (M)

First time: “I was 13 years old and was in my basement one evening. It was about a week or so after I had miraculously realized you could get Internet on the Wii and wanted to look at porn for the first time rather than awkwardly do it on one of my parents’ computers upstairs. I literally just put in the word ‘porn’ on Google search and realized that even though the Wii had Internet, it was definitely not a computer and could not play any of the videos, so I repeatedly failed at finding anything to watch until a random video began to work. I knew what masturbating was, but I didn’t really know why kids did it, so I decided to try it to see what all the hubbub was about. Nothing happened for a couple minutes so I was really befuddled. Then, randomly, halfway through the video, I stopped in confusion and then I just came and really had no idea what happened even though it was sort of fun. At that point I put the pieces together in my mind as to why exactly people enjoyed cumming and have enjoyed it ever since.”

Last time: “The last time I came was three days ago in my room alone sitting in my chair by my desk.”

Yoko (F)

First time: “So, it’s junior year of high school and I had just been dumped by the boy that I lost my virginity to. I was pretty torn up, but mostly I missed the daily sex and was ready for a change of pace. I started seeing this girl, which I thought was so cool and rebellious. Neither of us really knew what we were doing, but I think that was part of the fun. One day we were fooling around on her bed, making out and stuff and she put her hand down my skirt. I was a little nervous, but then I told myself, ‘Wait, you’ve totally done this all before. No need to be nervous.’ Little did I know that I had never actually had the full experience—sex is one thing, but an orgasm is like nothing else! I felt this heat in my toes that I’d definitely felt before, but this time I didn’t shut it down. I don’t know if it was the soft touch of another lady, or whether I just felt really comfortable with her, but I let the heat rush over my entire body. It was such an overwhelming sensation, but it was so awesome. I wanted to feel it again. Before I felt this, I always assumed that I must have orgasmed because I had had sex. I was so wrong. To this day, some well-timed fingering is still the way to an insta-orgasm for me.”

Last time: “Saturday night. The Bourne Supremacy was playing. I really couldn’t tell you anything about the movie. I can tell you that I was with a real cute boy who is super good at picking up on my cues.”

Doing these interviews was more fun than we could have imagined. We were surprised that hearing about people’s orgasms was simultaneously hilarious and empowering. So props to all you Wes lovers who get down with yourself and your partners in such a variety of funny, sexy, sweet, awkward, and original ways. We hope your next orgasm is just as weird and erotic as you are. We wish you all a very steamy summer!

Love,

Darwin & Grey