My First Time, by You - hooksexup.com

Female • 16 years old • New York, NY

He was probably not the natural choice to deflower straight-A super-nerd me. His ridiculous primary-colored baggy pants actually fell down in the middle of the street on at least two occasions that I'd witnessed. He sold acid to my lunch-table companions. Most damning of all, he had been my best friend's boyfriend before she moved away.

I never really understood his appeal. He may have been attractive, but it was obscured by his flashy over-sized clothes. Nevertheless, I found myself spending more and more time with him once she was gone. He propositioned me over the phone one evening while claiming to be drunk. My sexual experience at the time was negligible, so I was morbidly curious.

We went to his house after school. On the way, he stopped in front of a drug store, and said he didn't have any more condoms. I rolled my eyes and went in alone. The man at the check-out asked if it was for a school project. Something like that, I said.

Illustration by Thomas Pitilli

In his room, I turned away when he tried to kiss me on the mouth. It didn't seem fitting somehow. I'd read that prostitutes don't kiss on the mouth so as not to get emotionally attached. I thought I was being worldly and sophisticated, but more likely I wasn't too confident about my kissing technique. I let him touch me and take off my clothes. My gaze wandered to the picture frame near his bed — it was of him and my best friend. He saw me looking at it and pushed it face down. I put it back the way it was. I missed her terribly!

The sound of his belt buckle hitting the floor snapped me back. Released from the confines of his pants, an enormous cock bobbed up. It was too big for his thin, sinewy frame, ridiculously so. When I put my hand around it, my fingers weren't even close to forming a ring. There was no way it was going to fit into petite little me! I demonstrated the impossibility as he lay on his back. It hurt slightly as the tip entered, but it would go no further. The pain didn't matter because the situation was just too deliciously ironic — he was so proud of his monster cock, but functionally it was useless in this case. I couldn't help but giggle at the absurdity.

Then I started to feel something different from the stretching pain. It was almost pleasurable. I looked down, and abruptly stopped laughing. Our pubes were touching! I hadn't been expecting that and didn't know what to say. Then he started rocking his hips and I began to feel dizzyingly pleasurable sensations I had never even imagined before. As I rode him, I figured it out — it was like getting a massage on the inside!

And I was in for another surprise. I'd done my research on the mechanics of sex and knew about the male refractory period. But at sixteen, he didn't have one. After we both came, we stopped for a second to change condoms and then just kept going. I kept that first condom, the one with a streak of my blood, as a souvenir of the our three-hour marathon and pasted it into my diary.

I got home at about eight that evening. My parents must've attributed my unmistakable glow to the joys of studying in the library. He and I later fucked on two other occasions. The third time he tried to get his best friend to join us, to my horror. It fizzled rather quickly after that. Then the pangs of conscience kicked in and I confessed everything to my friend long distance. Nearly two decades later, she is still my best friend and we still laugh about the fact that the same guy popped both of our cherries. We hear he's married now with two kids and makes a lot more money than either of us. n°

We're looking for stories about the first time you had sex. Email with 300-800 words. (Don't worry, we won't print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.

29 Comments

He probably makes so much money because of the confidence that his giant cock affords him.

JL commented on 10/06

Yuck @ the 'pasting bloody condom in diary' part

aj commented on 10/06

Obvious fake.

AB commented on 10/06

He probably makes a ton of money in appearing in porn movies. LOL

DZ commented on 10/06

Fake, fake, fake.

PL commented on 10/06

It's good that the psychological "ew"s were rounded out with a couple physical ones too. Incredibly vague on specifics and reads more like a Penthouse Forum entry for women, though. Kinda lame.

SG commented on 10/06

you KEPT the condom???? ewwwwwwwwwwwwwwwwwwwwwww

sw commented on 10/06

Re: "fake". It's not particularly well-written, but I'm willing to bet that the 20+ years since the event will soften some of the memories and possibly change the stories.

PM commented on 10/06

Something tells me the women editors were on holiday when this tripe was greenlighted. Maybe they were all menstruating together, I hear they do that...

hc commented on 10/06

what 16-year old has a body-rocking orgasm her FIRST time? let alone with a guy who has a supposedly 'monster cock'??? (unless it just seemed huge because it was her first time?)

JC commented on 10/06

This is so fake! No one has an orgasm the first time...how ridiculous!

KK commented on 10/06

completely fake...so annoying Hooksexup!

AB commented on 10/06

I can't believe I am even writing this, but OF COURSE some people have an orgasm their first time. Are y'all even serious about calling it fake for that reason?

AK commented on 10/06

this totally reads like a penthouse letter. i do not believe that this is an honest reader upload. puh-lease... bring back rose and olive, bring back Siege, bring back something that doesn't insult our intelligence

adg commented on 10/07

This doesn't read like a Penthouse letter to me at all. I know that Hooksexup usually only publishes things that are double-edged in some way, but frankly I found this story, with its humor and unabashed celebration of mutually pleasurable heterosexuality, to be a welcome relief from the usual tales of woe, neurosis, and self-destruction. Some people really do have a great first time even if, when written down, it doesn't come with the kind of countercultural subtext to reassure you that you're reading something "edgy".

I.D. commented on 10/07

"It was too big for his thin, sinewy frame, ridiculously so. When I put my hand around it, my fingers weren't even close to forming a ring. There was no way it was going to fit into petite little me!" It has nothing to do with 'edginess' and everything to do with style - like when you just know something is an urban legend. This story has the earmarks of a fiction. Don;t get me wrong - I LOVE Penthouse letters. And I guess I'm happy that this column has turned into something you can jerk off to - but, seriously, Hooksexup used to be so much more. Mary Gaitskill, The Lisa Diaries, et al

adg commented on 10/07

@adg: Maybe, and yet I've known women who talk (and write like that). I don't know, I still think if there had been one well-placed reference to heroin addiction or something, everyone would be cooing over it. I agree that Hooksexup used to be more, but I can't say I mourn the Lisa Diaries, which epitomized the kind of self-consciously edgy stuff I don't miss: a lot of dysfunction, but not a lot of warmth or eros.

I.D. commented on 10/07

WOW you kept the condom that is discoustin I am 15 and just lost my virginity and i didnt do that likes seriously WTF I may not be the most sexualy active or the most popular person in my school but that gives me no reason to be unsanitary and keep a used condom full of cum that has blood on and put it in my diary that is just not right.....why would you even want to keep that????????......and like seriously if you dont like the story then get over it there is no reason to call it fake maybe the person just didnt want to say the "slang" terms so they said the more scientific terms.....and some people do have orgasms there first time because i sure did and im not fake so ya get your facts straight before you try to call something fake

NSL commented on 10/08

you pasted a used condom in your diary? that is just sick.

ay commented on 10/12

This story is 100% true except for the "after we both came" part. That bit must have been added by the editors. I didn't have an orgasm, but it was an extremely pleasurable experience nonetheless.

TFR commented on 10/13

my first time, same thing. i couldn't form a ring with my fingers around his cock. and i giggled. a lot.

mm commented on 10/18

I don't know why everyone professes so much disbelief about these stories. My friends and I have discussed our first times, and they're all as varied as the ones I've found here, from funny to tragic, from longterm relationship to one night stand. And there are huge cocks out there in the world.

rem commented on 10/21

If this really is original, and not paraphrased from somewhere, the writer should take up writing erotica.

EM commented on 10/21

if you can't "even come close to forming a ring around his cock with your hand"...you are making this shit up unless you have baby hands or a "strong hand" like in Scary Movie 2. BULLLLLL shit That would be considerably larger than a cucumber...doesn't exist

mts commented on 10/22

Did my wife write this? This perfectly describes our first time together, though there was more than a little pain, she did have an orgasm and she could not wrap her hand all the way around it. Before you consider it a monster, consider that she is petite with small hands.

LAM commented on 10/22

Yes this did seem fake....For one they went 3 hours on their first time....Usually its painful even if she did enjoy it a little I dont think that they would go that long....2nd knowing its her first time he tries to get his friends to join in the 2nd time??? Weird! And she keeps the condom and has to mention the streak of blood.....Not everyone bleeds on their first time this was so stereo typical...FAKE I conclude....

AA commented on 11/03

Its so fuckin fake!!

AB commented on 12/17

All the people yelling fake - you're idiots. It is entirely possible, albeit rare, to orgasm your first time. The issue is usually the lack of skill on the couple's part rather than anything structural or biological. And secondly, different people have different writing styles. That did NOT read like a Penthouse letter - it read like a romance novel. If the writer reads a lot of those, it is likely that she (in this sort of situation) would write like one as well. That being the case, this could be true, or it could be inspired by her favorite romance novel. I have no idea - my point is, neither does anyone else here. So stop being whiny idiots already.

NH commented on 01/19

@mts you are an idiot

np commented on 01/22

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