Every Time I've Had Sex With Megan Boyle, Pt. 1 of ?

Megan Boyle is the author of Everyone I’ve Had Sex With.


We were on my bed, facing each other on our sides. I was on my left side. It was ~3:30AM. There was some moonlight through my windows. We remained like this for maybe two minutes. Seems like my eyes were closed most of the time, because I was afraid of it becoming a situation where we were openly staring at each other, unsure what to do. At some point one of us moved closer to the other, in a “scooting” manner, I think, and I put my arm around her and we hugged for a small amount of time before kissing. Prior to this we had not touched in any manner that I viewed as romantic or sexual, in ~40 hours interaction with other people and ~80 hours interaction with only each other. We had slept in the same bed together maybe five times. I had, throughout, felt committed to not initiating anything romantic or sexual, except one night—a few nights before this night—I felt that I might want to initiate something, at her apartment, but she drank most of a Four Loko with a shot of tequila ~1:30AM, I think, to make a video to put on the internet, and we had also earlier that night ingested hydrocodone, Xanax, some LSD, and a little cough syrup, I think, and she passed out “big time,” it seemed, before I was able to initiate anything (she was on her back on her bed, unconscious, it seemed, with her MacBook on her stomach and I moved her arm to untangle a cord, or something, and moved the MacBook to the floor and lay beside her and sort of “pawed” at her arm and maybe shoulder a little, then meekly held her arm and briefly touched her hand probably, then put my arm on her arm and lay on my side, sort of facing her, and closed my eyes to sleep, in part thinking it could be interpreted, if she woke, as me sort of accidentally putting my arm on her arm, not me initiating something).

After kissing maybe ~90 seconds I think I began feeling that we were probably going to have sex, in part because it seemed like neither of us would want to stop until there was nothing more that could be done, and it didn’t seem like there would be another way for there to be “nothing more that could be done” than to have sex (at this point in the relationship I think neither of us ever expressed not wanting something, if the other person wanted something, but always defaulted to whoever wanted something). After maybe five minutes my pants were off, my penis was “out,” and it seemed like I was hovering it around her vagina for a medium amount of time, kissing her and sometimes touching her vagina with my fingers, I think, from above mostly. Her eyes seemed to be closed the entire time, which I interpreted as “not a good sign” because I had read from her “Every Time I’ve Had Sex” piece that I published on Muumuu House about a year ago, after reading it on her blog maybe two years ago, that she liked sex where there was “a lot of eye contact.” I think we moved in a manner where it was implied that we passively didn’t want to use a condom, in that there were probably thousands of tiny reciprocating movements, of increasing evidence, until I put my penis into her vagina, maybe guided by her to some degree, I don’t remember, that we were both acting as we wanted to act, in terms of condoms. I had read from “Every Time I’ve Had Sex” that she didn’t seem to have a strong concern, or any concern, maybe, about not using a condom.

We had sex ~50 minutes. I remember looking at the time after we finished because it seemed like a long enough amount of time that I felt unsure and curious about what time it was. I knew the approximate time we began because she was driving back to Baltimore ~8:30AM and we had calculated how much time we could sleep. We ended with our heads on the opposite side of the bed than we began. We were both sweating. I’m 90% sure I didn’t orgasm. I think there were moments when I focused on not orgasming, due to not wanting to without first knowing her thoughts about it. I’m not sure what caused us to stop. Seems like I must have felt that she orgasmed, as I did things with my fingers, and stopped. I felt optimistic that we had sex ~50 minutes because usually the first time I have sex with someone I don’t maintain an erection more than 5 to 10 minutes, I think.

12 NOV 2010 | SOLON, OH

We were at Jordan Castro’s parent’s house, in an upstairs guest room. I think it was ~11:30PM. After maybe two minutes of sex with me on top and the blankets over us, I think, we heard someone weakly knocking on the door (or making some kind of noise outside the door) and sort of panicked a little and stopped moving. I thought something important might be happening because we were both making quiet, but probably hearable from the other side of the door, “sex noises” that seemed like they would normally stop people from wanting to interrupt. Then I think the door opened a little, someone said something, and the door closed again. We were both naked, I think. Megan put on something quickly, I think, and went to the door. It was Mallory Whitten. I don’t remember what she said to Megan.

15 NOV 2010 | SOLON, OH

We were still at Jordan Castro’s parent’s house. Everyone in the house was sleeping. It was ~1:00AM. Megan was driving me to the airport ~6:00AM, then driving herself to Baltimore for a class she had that afternoon. We decided to ingest mushrooms and not sleep and film a movie. We each drank a cup of coffee and ingested mushrooms and a little Adderall, I think, and each “pooped,” or tried to, and showered. We did things on my MacBook a little in the living room then went to the basement. We kissed ~10 minutes in the “work out” room. We went in the “game room” and sort of rolled around on the carpet and did some somersaults, then went in a room that seemed to be used for working on things and closed the door and turned off the lights. We performed oral sex on each other (I was standing, I think, when she did it to me; I think she was on her back on the carpet when I did it to her), then had sex “missionary style” for what felt like a long time.

The mushrooms, somewhat unexpectedly, seemed to eliminate almost all inhibitions, most anxiety-causing thoughts, and all or most sensations not directly related to “sexual pleasure.” I seemed to feel unaware of almost everything except “sexual pleasure,” but maybe because it seemed like that sensation had, to some degree, “spread” to other areas of my sensory perception in a “blanketing” manner. It seemed like a detached yet “intense” form of sex. I think she orgasmed at some point, maybe when I performed oral sex on her, or after that, when I was fingering her, and then we had sex “missionary style” for what seemed like a long time, until I orgasmed in her, then went upstairs quickly and showered together in the guest room’s bathroom.


We checked into a large-seeming Hyatt after driving ~45 minutes searching for a hotel. It was maybe ~9:30PM. We put our things down and kissed standing—her back against the “foot” of the bed—maybe five minutes while relatively slowly removing our clothes. We remained standing a few minutes while I fingered her a little and she sort of fondled or “held” my penis. We seemed to be “taking it slow” this time. She moved backward, onto the bed, and I sort of crawled in her direction in an “advancing” manner, over her, and we had sex “missionary style” maybe 5 or 10 minutes. I think I orgasmed in her, then lay on top of her for an amount of time. I don’t remember if she orgasmed. I think she probably did because I usually don’t stop doing things to her until she orgasms. We showered separately, I think, then drove somewhere to eat dinner, I think. Thought Catalog Logo Mark

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