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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)
Great story! Had a similar experience with a friend that I still miss sometimes... One of my best sexual encounters of my life.
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.
@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.
Anal sex goes cleaner with condoms.
GROSS.
Don't throw the past away/
You might need it some rainy day/
Dreams can come true again/
When everything old is new again
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!!
I completely agree. Time to hear about the amazing-ness!
if enough people contribute good stories, i'm sure they'll make it happen.
Totally, the more people the more chance.
I think so too. People don't be too shy. Who says you even need to use your real name? Fake it.
@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.
Colbert Report? IM-ing? Holy fuck do I feel old.
I've read tow first time stories today on this
And they both end sadly...
Jesus - can i get a NICE first time story?
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.
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.
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.
HA! This is definitely the best way to lose it.
Hope my first is like this!!
sexy, naughty, bitchy = HOT!!
Love is my name
sex is my game
Fuck them till their hot babe. Sex is nothing to be ashamed of.
i love masturbating to this shit!!
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
How old are you
Girl, how old are you??!
hi I am first time guy needs female volunteers at Federalway WA 98003
reply me at billchrisfirst@gmail.com
r u friendship me plz i m waiting for you reply me at _ arfanzohaib@gmail.com ok
Hey man, there's no way anyone else on the planet would say no to that question.
Why would you say no to being a virgin...that first time hurts like hell!
In awe of that awnesr! Really cool!
Good point. I hadn't thoguht about it quite that way. :)
03046958520 THIS IS MY CELL NO. USING FOR YOU CALL ME OK
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...........
Awwwwww sooo cute
greattttttttttttt
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
?
I like your name and your game....
Oh, shit! I love masturbating to this stuff, hot. Oh, I feel like a bitch!
What the heck.