My First Time

Illustration by Thomas Pitilli

Female • 16 years old • Leicester, UK

I was sixteen and brimming with teenage angst, melancholy, and anger. Nirvana and the Smashing Pumpkins played constantly on my battered Sony CD player. My hair was dyed a cheap black that rubbed off onto all my pillowcases and the back of the couch. Basically, I was desperately trying to escape the realities of a middle-class, suburban family — the realities being that, rather uncool-ly, I was well looked after by mild, educated parents, fed, clothed, and given a generous allowance that I spent primarily on Silk Cuts, hash, and CDs.

He was twenty, from New Zealand, in a band, a casual pot dealer and skateboarder. Best of all, he lived with a friend in a chaotic, noisy house permeated 24/7 with the sweet smell of burning hash. My parents hated him.

I was sixteen and brimming with teenage angst, melancholy, and anger.

I had met him at a party thrown by his friend and housemate, and we'd spent a pleasant couple of hours smoking and making out. For the next six months or so, we had a sort-of relationship, in which he would text me a few times a week, I would go to his house, and we would smoke weed, watch horror movies, and make out. We were definitely not boyfriend and girlfriend. Nor were we really friends, actually — I was an utterly smitten kitten, but I got the distinct impression that he wasn't overly bothered, as evidenced by the facts that he occasionally forgot my name, and that his housemate used to walk me home because he didn't care enough to do it himself.

Eventually, I decided that the best way to advance our relationship would be to sleep with him. I had already broached the tricky subject of my virginity (in our group, still being a virgin at sixteen was unheard of) and he hadn't seemed too fazed. One day, we had the house to ourselves, and after awhile I decided to take the plunge. My exact words were "Get a condom. Let's do this."

There was a sharp, unpleasant pressure as we got started, and he seemed almost as nervous as I was. After the initial pain of penetration, it just felt weird, and not very pleasant. I was sweating, staring at the ceiling, and counting backwards from a hundred in my head, waiting for it to be over. Although he was disturbed by my lack of participation — I don't think I actually moved or made a sound during the entire process — he eventually finished, and went to dispose of the condom.

Looking down, I realized that the sex-ed warning that I might experience "light bleeding" was a huge understatement. The bed looked like a setpiece from The Texas Chainsaw Massacre, and my underwear was soaked. I had literally not seen that much blood since I'd broken my nose on a bouncy castle as a child. Nearly crying from shame and embarrassment, I tried to clean up as best I could, hobbled to the bathroom and fashioned a wad of toilet paper to line my pants, looking at myself in the mirror afterward to see if I looked different. (Apart from being a bit pale and sweaty, I didn't.) To his credit, he didn't mention the excessive bleeding, and we sheepishly went to share a cigarette in the garden.

It was actually my dad's birthday that day, and when I felt the blood start to soak through my pants, I quickly made an excuse about getting back to a party and left, half-waddling/half-running home. I immediately threw my knickers and pants into the trash, rang my best friend to tell her that I'd finally lost it, and went online to see if anyone had ever died from blood loss after losing their virginity.

Although our relationship died out a few months later, we met up again when I was eighteen, and now we live together. My dad's birthday remains known, between us, as our "sex-a-versary."

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.