Losing Your Virginity

i wondered if i should go into his apartment.  standing there i suddenly remembered something i read: “we teach children not to go into stranger’s houses, so why do it as an adult?” and thought about how he seemed very nice and gentle, but remembered hearing about how rapists and murderers often came off like that.  but i wanted more than anything to do this very adult thing, so i put everything out of my mind and nervously followed him in.

he apologized for the mess; he was in the middle of moving.  his floor was completely covered in boxes and clothes and household things, except for a made-up mattress laying on the ground.  probably most girls would have been put off by the state of his apartment, but i thought it looked interesting and was even pleased that this room was so far off from the romantic dreamscapes girls are supposed to want to lose their virginity in.

he left me alone by the door to go use the bathroom.  not knowing what else to do, i put my purse on the ground near the door and walked over and sat on the edge of the bed.

he came over and sat next to me and we talked more, and then started to kiss.  i laid down and he was sort of kneeling over me as we kissed.

“you’re a lovely girl.”  his voice was kind of firm.  i imagined he was expressing irritation with me for earlier telling him about being insecure about my looks.  i felt uneasy for a moment.

i put my forearm across my forehead in order to hide my unplucked eyebrows that were visible now that he had pushed my bangs aside.

but then i reached for the top button of my blazer and struggled to unbutton the top button.

“can i?” he asked, his hands above my blazer.

“okay, if you can.  these buttons are kind of hard…”

but he unbuttoned it quickly, with ease.

i was embarrassed that i was wearing an old plain white bra.

“…no shirt.”

“no, i told you,” i said, and looked up to see if he was staring at my breasts, but he was to my surprise looking at my face.  i wondered if he thought they were unattractive or if maybe he didn’t like breasts.

“i don’t think you did tell me.”

i pulled off my skirt and underwear, and then he moved his head down.

for a while i stared at the wall, and then i caught a glimpse of his head down inbetween my legs.  i wondered what he was doing.

after a few minutes he came up and his face was hovering over mine again.

“did any guy ever do that to you before?!” he asked with nervous excitement.  i could smell my pussy on his breath.  i wondered if he was excited by the idea of being first.

“do what?”

i had felt his face and hair rubbing against my thighs, but nothing else.  (a few years later i would learn i am completely unable to feel oral sex due to past sexual trauma.)

“…eat you out.”

“huh?  yeah, of course,” i said nonchalantly, lying.

“you’re like, ‘well, duh.’ he said, kind of laughing, maybe embarrassed.  i wondered if he was excited by the idea of being first.

he moved in to kiss me.  i wanted him to kiss me, but i didn’t want him to think i would want something like that, so i turned my head to the side to dodge him.  but he tried again, grinning big, and we kissed and i was excited by him forcing a kiss on me and forcing me to taste myself on his tongue.

then two of his fingers went into my vagina and it hurt tremendously.  my eyes snapped shut and i started to moan both from pain and out of feeling an obligation to make him think i was enjoying it, and feeling like i wanted to excite him by moaning and groaning.

i peeked my eyes open and saw his face was right over mine, watching my reactions.  he was grinning stupidly.

“god, you’re wet.”

he took his fingers out and held them up to the light.  they were drenched.  i wanted him to put his fingers in my mouth, but didn’t say anything.  he wiped his fingers off on my inner thighs and i pretended to be grossed out by that.

“you’re like, ‘eww.’”

he started to finger me again, faster and faster and then started to roughly rub my clit and i was in so much pain i had to fight back tears.  i wanted to fake an orgasm so he would stop, but i didn’t know how to or what women even acted like when they came.

i kept moaning louder and louder.

“tell me what you want,” he said.

i was too shy to say anything.

he kept fingering me for a while and then stopped and got on top of me, and through his briefs rubbed his erect cock on my crotch which i liked a lot.

“do you want this?” he asked, his voice was gentle and sweet.

“yeah…” i moaned.

“okay!  let me go get a thing,” he said and bolted up.

i stared at his legs and ass in his green american apparel briefs as he walked across the room.

then he was kneeling down beside me, and i could hear him unwrapping a condom.  i turned to look at him.

“you don’t really want to watch this, do you?”

i turned my head.  i wondered why he would be embarrassed to be seen doing that.

then he said, “i think i put it on inside out…”

“oh my god” i said and started laughing.  is this really how i’m going to lose my virginity?

oh my god” he mimicked.

and i felt a bit offended and wondered if i wanted to have sex with someone who had teased me.

he got on top of me and i was in pain as he tried to penetrate me. i was moaning and maybe i sounded like a hurt kitten.

he put his mouth against my ear and shushed and whispered, “don’t be nervous.”

i wondered why he was saying that when i felt totally calm and relaxed.  it was completely the right time for this to finally happen.

he struggled to penetrate me again, which hurt to the extent that i didn’t even notice when he did finally penetrate me until i lifted my head up and saw his cock going in and out of my vagina.  it was so shocking and strange and interesting looking i wanted to keep staring at his cock going in and out, but i could tell he was looking at me staring and so i felt self conscious and laid my head back down.

even though i had been watching pornography regularly since elementary school this was so completely different than what i thought sex would be like.

i called out his name, thinking he would like that.

“god, you’re tight…” he moaned.

i wondered what that meant.

it hurt a lot.  he was fucking me really hard and fast (later he would admit he was incredibly excited to be having sex with an 18 year old), but somehow i loved the feeling and thought things like, “it hurts, but it hurts so good…”

he went on fucking me for awhile, me laying there half out of my mind in this strange painful pleasure, moaning like a hurt kitten.

but i was suddenly overcome with shame, stemming from feeling disconnected from him and his body.  i felt that this couldn’t have been good for him.

“i’m sorry.”

“…for what?”

there was a strong feeling of awkwardness.


More From Thought Catalog

  • Dangertime

    I get the impression that the dichotomy between the feelings expressed in the last paragraph and the rest of the essay is meant to come across as melancholic and a bit ironic. I don't really think that turn works though. The disconnect mostly just seem too unexpected (or maybe arbitrary) and that causes those emotions to feel unearned.

    • az

      i agree

    • http://www.facebook.com/people/Carlos-Ortiz/1279921705 Carlos Ortiz

      I think feelings are arbitrary in general.

      • eric

        Not by the time you've put them to words.

  • http://twitter.com/itchypeach etsena

    goddamn! this was very weird…porn version of thoughtcatalog..

  • LDN

    this makes me sad.

    i like the sound of the guy you lost it to, he seems nice. he definitely knew it was your first time.

  • Justsayin

    Idk. Last paragraph killed it (in a bad way.) You made it seem like sex was really good with him (although you stated the opposite throughout most of the essay.) And although losing your virginity can be a very emotional thing, I find it kind of naive and immature that after a month of being FWB, you think you'll never have sex that good or ever love someone as much. As your guy would say, “Like…you're 18. Grow up.”

    • alice

      Way to invalidate an individual's personal experience.

      • Frances

        I don't think this piece has anything to do with individuality. This woman lost it to a pile of brand name clothes. It's ultra-ridiculous (hey, a better name for your tumblr Ms. C) that she identifies with anti-capitalist politics.

      • http://twitter.com/AKAGoldfish Dickey El Shavaz

        How is pointing out someone wears American Apparel underwear in a work of narrative non-fiction inconsistent with Marxist politics? Oh right, it's not.

      • Frances

        How is a brand obsessed consumer whore inconsistent with Marxism? You really want me to answer that?

  • http://twitter.com/cream_dreamz Stephanie Jones

    What is with the lack of capitalization? Is this live journal?

  • xtos

    what the fuck……

  • http://twitter.com/t_baugh Travis Baugh

    why does everyone dick-ride stumptown so hard it's nothing special

    • cameron wray

      the glow from all the macbooks is super flattering probs

  • Anonymous

    Call me naive, but I hated how you presented the act of sex as such a hideous thing–the lying, the fact that you had sex with a stranger, the impersonal element–and how you were unable to recognize how ugly this encounter truly was. Not only was it wholly unromantic, it was completely lacking respect. You had sex WITH A STRANGER, which would be bad enough, but this was your FIRST TIME. Jesus, and at the end, you ask to have sex with him AGAIN. A part of me is totally disgusted and a part of me pities teenagers who are unable to grasp the concept of self-respect.

    • skyvillain

      I felt it was honest and captured a lot of the awkward self-doubt and conflicting feelings people have when having sex, especially for their first time. I don't think it's fair to judge someone who decides to lose their virginity with a stranger, and I wonder if it was a male if there would be that same judgement. And as the author mentioned she was a victim of sexual abuse, so I imagine a lot of the feelings are affected by very negative past experiences. I too could have done without the last paragraph, but overall the piece moved me and I'm glad the author didn't try to put some sort of cherry coating on her experience because people have false assumptions of what it should be like to lose your virginity. It's a personal experience.

      • http://tomhankssuperfan.blogspot.com megan boyle

        double-liking this in the form of a comment so there can be more positive comments on this

    • http://tomhankssuperfan.blogspot.com megan boyle

      to me, it doesn't seem like she presented sex as “hideous” or “ugly” by writing about her experience. i feel like if anything, because of the level of honesty present in this it's human and vulnerable and i felt a degree of “aliveness” while reading.

      do you feel there is an inherent need for sex to be “romantic?” what specifically isn't “romantic” about this? what is “ugly” about insecurity? why do you feel like she has personally affronted you with writing about her life?



  • 45hundred

    this sounds so unpleasant and uncomfortable. the last paragraph ruins it, though i didn't really enjoy reading any of it.

  • kharlamovaa

    I love the contrast within this article, in comparison to the other commentators. I found it complicated in a “i want this because this is what i'm supposed to want” but also “i don't really want this” way.

  • 305NYC

    I don't know. I kinda liked it. You didn't know what it was to lose your virginity . You just played it by ear through it all. It was confusing to read, but I'm sure you were more confused throughout it all.

  • alison

    i liked your essay. it was honest and brought me back to my first time. which was with a stranger and extremely awkward. small caps works for me too–evokes being a teenager. the last paragraph, whatever, maybe you could have let our imaginations figure out the ending. but good job, good article.

    • everyone

      i dont think this is an essay.

  • Ro

    The last paragraph threw me off, but not in a bad way. I feel scared now, because you sound a lot like me… I want to ask you for advice now..

  • Justbecauseitsssmutty

    Kind of just smut.

  • ANON

    Oh my god. This was exactly like my first time. You write so beautifully, please write more because this is probably the most honest thing I've read on TC. Thank you thank you thank you.

  • rushel

    This brought me back to my own first time, although, I can't honestly say I have a clue what the denouement is.

    Thought it would have been good when I first started, but I became progressively let down.

  • nayka

    It's the feeling of heartbreak that comes when you let someone in like this for the first time, of feeling as if your facade has been peeled away for the world to peer at and you've lost a battle within yourself. Sex reveals and strips you emotionally bare unlike any other action, and my first time was as raw as this one. The self-questioning and evident discomfort communicate themselves choppily–and each is augmented in its intensity through the choppiness–and with perfect syncopation. I never questioned myself more and less in a single moment than when I lost my virginity, and you captured that well.

    • Frances

      Then let's hear your story because you clearly are the better writer.

  • okay...

    dear penthouse forum

  • http://www.facebook.com/people/Carlos-Ortiz/1279921705 Carlos Ortiz

    I loved this article for many reasons, the fact that it got me hard at certain parts, a common expression on the pornier TC article's comment section, not necessarily being one of them.
    It was interesting and informational and felt sad and funny, and I found those feelings interesting also. I felt like I gained insight from it and empathized with girls and their sexual experience recognizing it as different and appreciating it for what it is.
    Felt self-aware of my limited sexual experience and shame that it was to a prostitue, not because of the act or implications in itself, but because it's the only time it has happened and I can only blame it on my personality and what maybe be perceive by some as lack of 'game'.
    Felt appreciative and respected you for sharing an intimate experience, then started thinking “maybe she didn't even find it hard” after seeing sex as the first interest listed on your author page.
    Felt intrigued by the meaning of 'past sexual trauma' being either physical or psychological and very interested .
    Felt like I wanted to experience 'something'.

    • http://www.facebook.com/people/Carlos-Ortiz/1279921705 Carlos Ortiz

      I also like how your reference for sex was porn because similarly my reference for relationships was TV as a kid, and we both experienced discongruity.

  • http://profiles.google.com/bpike53199 Brad Pike

    As a general rule, I always click pictures of girls in their underwear. It's worked out pretty well for me so far.

  • http://profiles.google.com/benj.caro Ben Caro

    I gotta say, the unformatted punctuation in this piece makes it really chilling, as if we're reading an AIM conversation from some tweenage girl. Very brave to be spilling out the details like this. Good job. Why did you wait til the second to last paragraph to describe him? I hope it was intentional.

  • JoseG(:

    I really enjoyed this. ^__^ not for THAT reason tho. :S lmao much love<3

  • Reallydudeeeee

    So, you got raped by a man in american apparel briefs (that's all you had to say for everyone to understand what kind of guy he was) who had such little self confidence that his idea of being funny was mimicking you when you were both self conscious. okay, not terrible at all or anything.


      I hope my first time is like this too.

  • http://profiles.google.com/bpike53199 Brad Pike

    I appreciate that thought catalog posts women writing unself-consciously about the experiences of being a woman and doesn't dismiss these stories as “live journal” or “teenage girl shit”.

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