Ten Illustrated Stories About First-Time Sex

Funny, sad, and nostalgic tales submitted by Nerve readers.

Do you have a great first-time story? Tell us! My First Time runs every Tuesday on Nerve.com.

My First Time - Illustration by Thomas Pitilli

Illustration by Thomas Pitilli

Male • 18 years old • Maine

It was the end of winter break, and I was meeting a girl at the airport to head to NYC for a week of sightseeing before school started up again for the spring term. She had been my best friend for the past six months, and I think she'd known all along that I had a massive crush on her. She hadn't acknowledged my interest, though, except to say that she wanted to be single after a bad experience breaking up with her last boyfriend. I arrived an hour late, and as we were loading her luggage into the trunk of my '94 Volvo, it stalled out, so we were stuck waiting in the front seat until it would start again.

While we waited, we talked. I asked her about her vacation (she lived in Hong Kong, so any story was interesting), and told her about mine. And then it was silent. "I missed you," I said. "A lot."

"Me too," was her answer, and she leaned over and gave me a quick hug. In the darkness I fumbled for my keys and tried the ignition again; the car started and we headed for our college.

That night we were staying in the dorms, planning to make the trip to NYC the next morning. I dropped my two duffel bags off in my room, then went upstairs to hers to keep her company as she sorted through her three suitcases and two boxes of clothing, electronics accessories, and documents. Hours later, she finished putting everything into its proper place, and it was time to sleep so that we could get an early start in the morning. We hugged, said goodnight, and then I hesitated before going out the door. "You don't want to go downstairs tonight, do you?" she asked.

"You have to understand that I don't love you," she said.

She had a liberal attitude when it came to physical affection. All sorts of hugging and holding hands and kisses on cheeks were acceptable, which was very different from my upbringing. So I'd been surprised the first time she had asked if she could just fall asleep in my bed (we'd been watching the Colbert Report online and she said she was too comfortable to get up). But I'd gotten used to it, and understood that it didn't mean anything. I thought that that night would be no different. I wanted to stay with her, even knowing that my affection wasn't reciprocated.

Imagine my surprise thirty minutes later, when, after lying in the dark talking for what seemed like an hour, without warning, I felt her lips against mine. It was just a quick peck, but it stopped me mid-sentence. "What was that?" I asked.

"What was what?"

I rolled over and pulled her head toward mine, and kissed her as passionately as my inexperienced lips would allow. "That," I answered.

We made out for hours, and I felt and saw real breasts for the first time in my life, but we stopped short of going further that night. The next night, after driving to a friend's place in NYC, I audaciously reached down and teased her with my fingers, but she prevented me from pulling off her underwear when I made an attempt. The third night began the same way. We kissed, I fingered her, she ground against me for all she was worth — and then abruptly she was still. "I can't help myself," she whispered in the darkness. "I want your dick."

I was stunned momentarily, but my instincts took hold and I started to fumble with my pants button in the dark. But she grabbed my arms. "You have to understand that I don't love you," she said. "If you don't want to do this with someone who doesn't love you, I'll understand."

It was at that moment that I realized that I, tragically, truly did love her. But my body didn't give me time to think about how miserable that would make me in the near future. I wanted her more than I had ever wanted anything before in my life. Every fiber of my body was screaming at me to stop stalling, to pull this girl against me as tightly as I could and never let go. I pulled down my pants, peeled off her underwear, and lay on top of her, hard as a rock. I whispered breathlessly, "That you would ask that question means that you care. And that's enough for me," and slid into her.

My unrealistic expectations and her relationships with other boys spelled disappointment for me and disaster for our friendship. We had sex a few more times, but it was never like the first time again. It was worth it though, for that one night, that one hour of honest innocence and senseless happiness. I'll never forget it, and I'll never forget her.

Commentarium (41 Comments)

Mar 05 11 - 1:44am
DIC

Great story! Had a similar experience with a friend that I still miss sometimes... One of my best sexual encounters of my life.

Mar 11 11 - 6:57pm
ekym62

Great sexy story but glad I'm a guy and not the recipient of the de=virgining. I love you girl but the guy is notworth remembering. Hey just the way I see it.

Mar 05 11 - 2:41am
dude

@Female, 17 years old, Dakotas -- whose parents use condoms? The only reason I could think of was that they were swingers. I'm not saying your parents were swingers, but, you know. Maybe.

Mar 05 11 - 11:53pm
Catfishman

Anal sex goes cleaner with condoms.

Aug 31 12 - 1:56pm
The Heck.

GROSS.

Mar 05 11 - 4:18am
nope

Don't throw the past away/
You might need it some rainy day/
Dreams can come true again/
When everything old is new again

Mar 05 11 - 11:46am
petersealy

Sheesh - enough with the "first time" stories already - confused fumbling between people who don't know what they're doing. Let's hear some "best time" stories!!

Mar 05 11 - 1:21pm
pic

I completely agree. Time to hear about the amazing-ness!

Mar 05 11 - 11:46pm
go for it!

if enough people contribute good stories, i'm sure they'll make it happen.

Jan 31 12 - 7:18pm
Jenna

Totally, the more people the more chance.

Jan 31 12 - 7:21pm
Jade

I think so too. People don't be too shy. Who says you even need to use your real name? Fake it.

Mar 05 11 - 10:28pm
none

@dude ... Her mom probably wasn't reliable to keep up with the pill or other methods. And they didnt want anymore kids. So condoms seems like a logical last resort.

Mar 08 11 - 7:46pm
H

Colbert Report? IM-ing? Holy fuck do I feel old.

Mar 09 11 - 4:38pm
Cathy

I've read tow first time stories today on this
And they both end sadly...
Jesus - can i get a NICE first time story?

Mar 11 11 - 6:40pm
ekym62

Nice story and I admire it. You my girl, made a giant step in your life with a great attitude. You're going to be a heart breaker before you reach 30. The boys love you, be kind.

Mar 16 11 - 11:32am
ab

Wow, male person from AL, you ARE a horrible person. I hope it was only the raging teenage hormones that had blinded you to what doing the right thing is, and that you'll know better to treat people/women/girls like that anymore.

Feb 10 12 - 5:12am
bf

leave him alone, teenage years arnt spent with one person, live a little and let it just roll. I doubt there relationship lasted because she wouldnt have sex, he is a teenage boy who has needs she cant help him with... so what happens happens. I dont see anything wrong with it.

Mar 30 11 - 3:03am
MyFriendsJustLostIt

HA! This is definitely the best way to lose it.

Mar 30 11 - 3:03am
MyFriendsJustLostIt

Hope my first is like this!!

Apr 15 11 - 9:26pm
wheresmyvirginity?

sexy, naughty, bitchy = HOT!!

Jun 23 11 - 8:33am
Karthik

Love is my name
sex is my game

Jan 31 12 - 7:26pm
karma

Fuck them till their hot babe. Sex is nothing to be ashamed of.

Apr 15 11 - 9:27pm
wheresmyvirginity?

i love masturbating to this shit!!

Apr 26 11 - 11:11pm
Paige

I know this is going to sound corny but, I almost cried at the part where she said she didnt love you. Im such a nerd this tugged at mt heart strings just a bit

Nov 09 11 - 10:50pm
How old are you

How old are you

Aug 31 12 - 1:46pm
Yeah

Girl, how old are you??!

May 06 11 - 12:30pm
chrisF

hi I am first time guy needs female volunteers at Federalway WA 98003
reply me at billchrisfirst@gmail.com

Aug 13 11 - 8:06am
arfan

r u friendship me plz i m waiting for you reply me at _ arfanzohaib@gmail.com ok

May 23 11 - 3:23am
DonLaFontaine

Hey man, there's no way anyone else on the planet would say no to that question.

Apr 30 12 - 6:20pm
bryce

Why would you say no to being a virgin...that first time hurts like hell!

Jun 10 11 - 2:02am
Nash

In awe of that awnesr! Really cool!

Jun 12 11 - 10:01am
Lesa

Good point. I hadn't thoguht about it quite that way. :)

Aug 13 11 - 8:16am
arfan

03046958520 THIS IS MY CELL NO. USING FOR YOU CALL ME OK

Jun 15 11 - 6:06pm
ylshp89

How nice if yls (8/9/87) give her first time to me. I, shp will love and take care of her till end of our life...........

Jul 22 11 - 4:48pm
Blah

Awwwwww sooo cute

Sep 05 11 - 1:02pm
shezi

greattttttttttttt

Sep 12 11 - 1:30pm
Stefan

Hey so I live in Pennsylvannia and I am really hoping the YMCA that this guy lost his virginity in is not the one I live down the street from! hahahah because I know a few Ashleys that fit his description.....hahaha

Aug 31 12 - 1:48pm
Question Mark:

?

Oct 31 11 - 10:07am
Harold

I like your name and your game....

Jan 31 12 - 7:29pm
Janet

Oh, shit! I love masturbating to this stuff, hot. Oh, I feel like a bitch!

Aug 31 12 - 1:48pm
...

What the heck.