My First Time

Female • 16 years old • Rutherford, NJ

I was dating my first real boyfriend. He had a rep as a bad boy, which made me want him more. He was also a full five years older than me, and at sixteen, that's a big deal, especially to your parents. We'd been going out for a month and a half when my mom sat me down for "the talk." She insisted that guys were going to give me lines like, "I need to have it now," "If I don't get it I'll have blue balls," and "I'll leave you if you don't put out." At the time, I nodded right along and thought how stupid it was for guys to think that they could use such passé lines. They would never work on me.

Illustration by Thomas Pitilli

Until one day, when Bill was dropping me off, he used the one that struck fear into me. He said that we'd been going out long enough (a month and a half), and if I didn't sleep with him he would break up with me. Now to me, Bill wasn't just a regular guy. He was a twenty-two-year-old big deal, six-foot-four, with blond hair and blue eyes. I just couldn't see myself fumbling around in the dark with some half-wit at my high school, so I agreed. I thought about what my mom had said, but it didn't settle with me that it was just a line. He meant something to me. I wanted to do it right. At that moment, right after I agreed, my heart was in my throat. I looked at him sitting next to me in his car — at his body in his jeans, his flannel jacket, his big gentle hands as they gripped the wheel — and knew this was it. I was choosing him to do the deed, to turn me from a girl into a woman.

We arranged for "the night" to happen at his house. He didn't live in a household like I did, with two parents who gave a damn. His mom was an alcoholic who kept to herself, and his dad avoided her like the plague. I envied his freedom.

He went to a local drugstore and bought a pack of Trojans, and we went to his bedroom. I was so scared, and as he turned off the lights in the room, he left one on, casting a greenish glow. I took off all my clothes, and he slowly took off all of his. I had never seen his dick before, and it was huge. I touched it, and it was solid, veiny. Terribly frightening, like something out of a Stephen King novel. It grew of its own accord. Now, I wasn't stupid. I knew how reproduction and sex worked, and we had had plenty of makeout sessions, but things had never gone below the belt before. I looked up at him and said, "You're not putting that thing in me." I knew the first time hurt, but this was going to be agonizing. Worse than using a tampon without an applicator.

He smiled, kissed my head, and reassured me that he would go easy on me. Foreplay that night brought on an entirely different meaning — because this was definitely going to go somewhere! I was sick of being the last virgin among my friends, a subject of ridicule, and I kept hearing about everyone else doing it. It sounded so great, so cool, and I wanted to get it out of the way. I kept telling myself it was just a rite of passage. But as Bill's mouth reached my pussy to warm me up, tears slid down my face.

He looked up after a moment, and saw my fear. A sweet smile came over his ruggedly handsome features and he kissed my face, held me, and then put on the condom. I watched it all happen, detached, almost feeling separate from my body, so desperate to record this event in my mind. When he entered me, little by little, it hurt like hell. Worse than any menstrual cramps I had ever felt. I couldn't believe that I would ever come to enjoy sex as a whole. He reneged on the gentleness and thrusted into me more rhythmically, harder, and after awhile I stopped feeling the pain. Something had broken inside of me, and I became engulfed in warmth, wetness. He moaned and gave one last thrust, and I felt his dick pulsing in me. When he pulled out, we discovered the source of my pain relief. I had bled all over him and his sheets. Panicked because it wasn't my period, I cleaned myself up, while he removed the condom (which thankfully hadn't broken).

He wanted to do it again, but I refused. I was sore and scared, and just wanted to get home. He got angry with me, saying that "an experienced girl wouldn't have an issue with this" and that I was acting like a baby. I just lay there and cried, curled up on my side. This sure wasn't how I dreamed it would be. Then he apologized to me and held me — his guilt must've gotten the better of him. "I'm sorry. I forgot that for girls, it hurts a lot. Maybe I was asking for too much of you."

On the ride home, I felt different. Instead of a girl now, I was a woman. But what I really felt like was a scared kid who had gone too far with the wrong guy. He gave me a hug and a kiss, breathed into my tenth-grade hair, "Thank you," and I got out. After exchanging a knowing smile, I went back into the house. Instead of walking with my head held high, I came in slumped in confusion.

We're looking for stories about the first time you had sex. Email with 500-1000 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.
By sheer chance, Jack and I both ended up in Shanghai that summer.
According to just about every pre-college advice manual, floorcest is a bad idea.
"So no, I didn't lose my virginity in the most traditional way."

Commentarium (35 Comments)

Jun 29 10 - 2:24am

When I was 16 my bf was 21...I always felt like my first time was so perfect but after reading and relating to the end of this story I kind of feel differently :/

Jun 29 10 - 2:30am

Sad story, written well and with sensitivity. I appreciate the fact that the author depicts the guy not as some kind of cartoon, but as a human being capable of both kindness and selfishness, compassion and callousness. The age difference doesn't help, but like the author said, the essential issue is that she was a scared kid who went too far with the wrong guy. Still, if he had just taken the time to introduce her into sex a little more gradually, the outcome could've been a lot happier.

Jun 29 10 - 2:32am

Meant to add: losing your virginity if "things have never gone below the belt before" is total madness whether you're male or female. I'm surprised the guy didn't realize that, if he'd been around and was (apparently) willing to eat pussy.

Jun 29 10 - 2:34am

that makes me so sad for her.. My first time was undoubtedly easy because I was drunk and my hymen had broken after years of gymnastics. Plus I'm still with the guy who took my virginity because we had been close friends in high school. we've been together nearly five years.

Jun 29 10 - 8:34am
robert paulsen

sad story. well worth reading, though.

Jun 29 10 - 9:09am

Sad story. Makes me want to have a long talk with my daughter about the importance of loving and respecting the person you have sex with. And that there is no reason on earth to feel when needs to have it for the first time at 16 unless one really wants to.

Jun 29 10 - 9:52am

This is upsetting, but a lot closer to my own experience.

Jun 29 10 - 10:40am

Feels bad man!

Jun 29 10 - 12:13pm

Where does this notion that having sex makes you a woman come from? Having sex does not make you emotionally mature, or ready to handle responsibility, or make someone suddenly able to make good decisions.

Jun 29 10 - 12:30pm

I think everyone feels this way after his/her first time no matter how well you plan that first experience. The author did a good job explaining this confusing emotion.

Jun 29 10 - 2:13pm

"....Maybe I was asking for too much of you." What a classy, thoughtful, reassuring thing to say to a girl after you took her virginity. How about a side of You-were-okay guilt to go with the huge serving of My-mom-told-me-this-would-happen guilt. This pretty much qualifies him as a Grade-A douche.

Jun 29 10 - 3:34pm

If you think that's Grade-A douchery, then you need a refresher course in Douche Identification 101 (lab fee $75.00) because believe me, there are far, far douchier specimens in the wild. To be honest, I don't really see a problem with the quote you pulled, but maybe that's because I'm not interpreting it as code for "you were a bad lay" (which is what I think you're doing?).

Jun 29 10 - 4:21pm
uh huh

I'm always surprised when high school kids are dating (usually) guys well outside of hight school. It also seems to end badly more often then not. My group didn't have any older kids in it and I could never figure out where the freshmen/sophomore girls that were below me were meeting their much older/loser boyfriends.

Jun 29 10 - 9:10pm

16+22= statutory rape

Jun 29 10 - 9:59pm

Not in New Jersey, where 16 is the age of consent.

Jun 29 10 - 10:32pm

Umm... I'm fairly disturbed that no one is pointing to the fact that this guy was pressuring her into sex clearly before she was terribly interested in it as a sign that he was, in fact, a Grade-A douche. The whole "I'll break up with you if we don't do it now" thing? Totally emotionally immature. He shouldn't have been dating a 16 year-old girl to begin with, if sex was all he cared about. The dude in this story sounds like an idiot. He may have had some emotions and some level of compassion, but he was still a huge idiot. I've met better men. Trust me they're out there. I'm disappointed that so many still see this guy's behavior as "normal."

Jun 29 10 - 11:38pm

In some ways I agree with you, but I absolutely detest it when people say things like "if sex was all he cared about", because that's about the oldest and cheapest tactic in the book. There's absolutely NOTHING wrong with wanting to get laid, wanting sex to be part of a relationship, or losing interest if the other person's not ready or willing to become sexual. That goes for ANYONE, male or female, who's above the age of consent. Wanting these things isn't selfish or evil, and it doesn't mean that you "don't care about anything else".

Are there better men out there? Hell, yes! And none of these excuses the guy's behavior; he should've taken things slower, shouldn't have pushed, and should've understood that if he was going to date a 16-year-old virgin, he had to be especially patient and kind. But that's also what happens when the power dynamics in a relationship are unequal. Given that the author was obviously attracted to all the things about him that MADE that dynamic unequal, it's hard to see him as the consummate villain (no pun intended). He was just a douchey guy who wanted to get laid, and didn't take the time to help his girlfriend really be ready for it, but who at least cared about her somewhat. She was just a confused teenager who was attracted to someone who seemed self-confident and a little dangerous, and ended up getting hurt by the same qualities that attracted her in the first place. The only real moral is: live, learn, and hopefully do better next time.

Jun 30 10 - 12:41am

Wow, I did not like how this was written.

High school girls and wanting to date older. I always think that there's a problem with an older guy seeing someone in high school. I mean there are exceptions, but...

Jun 30 10 - 3:01am

your full of shit. the girl is a child. you dont fuck children. the guy is a piece of shit to go from above waist to fucking with nothing in between. his repulsive behavior is not within the normal/moral/halfway decent code people try to live by. the bullshit you say "everyone wants sex" yeah ok, but when one of the people is obviously still an immature kid, those little "dating" rules dont apply. hes a scumbag. and sex WAS all he cared about.

Jun 30 10 - 3:27am

get a grip, and save your half-coherent, foaming at the mouth, righteous indignation act for someone who gives a shit. no one is saying that it's awesome that this guy did what he did, but it's stupid and inflammatory to use the word "child" as if 16-year-olds are the same as 10-year-olds. they're teenagers, and teenagers fuck. they fuck each other and they fuck people they shouldn't and they fuck people who hurt them and treat them badly. your post doesn't help them; it's just a bunch of spew no one wants to read. STFU.

Jun 30 10 - 4:27am

I really wanted this to end with "I refused to speak to him ever again" or something similar :(

Jun 30 10 - 5:28am

This guy clearly hadn't heard of the Campsite Rule.

Jun 30 10 - 10:27am

Sex WAS all the guy cared about, is the point. I, nn, originally said "sex was all he cared about" not because I think it's wrong to care about sex, but because in this particular instance, obviously sex was all this guy cared about. You need to stop projecting and look at the situation at hand.

Jun 30 10 - 10:34am

Really sad that she thinks this makes her a woman now. Obviously it didn't because after sex, she still felt the same. Scared and confused. Should not have had sex with this guy, and should not have had sex yet. She doesn't sound mature enough, but that's just my opinion...

Jun 30 10 - 11:18am

Everybody feels this way after their first time? That's ridiculous. If you actually are ready to have sex, feeling sad and confused and wondering if you're a "woman" now will not be issues. When I first had sex, I was more than ready, I already felt like a woman despite the fact that I had never been penetrated by a penis, and I knew that I would be exactly the same person afterward. I was, and am. This is true of many people I know. I'm sorry if you're experience was different.

Jun 30 10 - 12:36pm

Sorry, I still think it's a lousy line that plays into all kinds of destructive stereotypes about gender relations. Did the guy care MORE about sex than her well-being? Yeah, absolutely. But the author clearly realizes that he was also conflicted (in his douchebaggy kind of way), and if she sees fit to make that distinction, I think we can as well.

Jun 30 10 - 1:34pm

Boys think having sex makes them a man. Girls think having sex makes them a woman. Been that way since the beginning of time. Ain't gonna change now. The only hope is to make kids smarter about their choices.

Jul 29 10 - 12:42am

What mother let's her 16 year old go out with a 21 year old? That is just ridiculous. And has sex only after a month and a half? Maybe I am old fashioned. But i would hope sex would come later especially in this relationship where age is a major factor and she apparently cared a lot about him.

Aug 04 10 - 3:55am

I think this story is a total fake.

Aug 17 10 - 5:08pm

this is such a typical story

Sep 22 10 - 7:06pm

rutherford!! represent!

Sep 27 10 - 1:25am
What the fuck?

"Fuck me or I'll break up with you," "I just lay there and cried, curled up on my side. This sure wasn't how I dreamed it would be."

Just because she was forced into thinking she should do it through "love" for this guy, and peer pressure, that was rape, loud and clear. Poor girl is going to have issues with guys for the rest of her life, and that pathetic bastard is going to manage to keep forcing young girls to have sex him. What a fuck bag.

I'm sorry, sweetie. They're not all like that.

Oct 20 10 - 3:40pm

"Just because she was forced into thinking she should do it through "love" for this guy, and peer pressure, that was rape, loud and clear."

"keep forcing young girls to have sex him"

This girl was not forced. A 16 year old is not some helpless child; she made her own decision (pressure or not). I can't help but think that adults that have a lot of bad experiences weren't told as teenagers, "It's not your fault, sweetie."

As for the guy, and besides the obvious age difference, I don't see how you could keep going after seeing her crying.

Jun 25 11 - 7:16pm

Thanks for sharing your story. Touching. Would have loved to know if it went on and for how long after this.

Nov 20 11 - 6:59am

This story made me cry so much. I remember my first time, I was only 16 and my b/f at the time was 21. I lived in a different town to him and was staying the night with friends. One of my apparent friends sexually assaulted me and when I told my b/f he made me feel guilty and that I owed him something to stop us from breaking up. He wanted my virginity and I was too obliging to make him happy than stand up for myself and say no, but, I gave myself to him. I wasn't ready and I hated every second of it. a couple of months later I fell pregnant to him because he was too involved in the act to stop and put something on and now I have to see his horrible face every second w/e as I kept my baby boy even when he told me not too. And now, 7 years on, I only ever remember how bad he treated me every now and then. This story is awful and the sad thing is that those of us who lose our virginity in these kinds of circumstances, generally suffer in silence, too ashamed to tell anyone how bad our first time really was.