My First Time

Illustration by Thomas Pitilli

Female 17 years old Back of a car

My best guy friend, who had served as my first boyfriend years earlier, had recently come out to me as bisexual. His boyfriend was edging his way into our group of friends, which pushed us all a bit more to the wild side. The boyfriend was older and taught us to sneak out of our houses and steal alcohol from our parents. One wintry weekend, we made a daring plan to camp by the lake in our cars. We snuck out late, after listening at our parents' doors to make sure they had fallen asleep enough to miss the noise of our cars leaving.

Arriving at the beach, it became clear that the weather was not conducive to hanging out. It was pitch black and below zero. My friend Monica and her boyfriend, who had recently lost their virginities together, immediately holed themselves up in his car, and I knew they would be practicing their newly discovered hobby to help them generate heat.

That left me, my guy friend, and his boyfriend standing outside my SUV. We put down the back seats to make room, turned on some music and the heater, and chatted for a while. Soon though, we had to turn off the music and heater, because we knew that neither my gas tank or my battery would last through the cold night. So, we had to come up with a way to keep warm.

Both boys knew that I was a virgin. The boyfriend coyly suggested that they could help me out in that department. When I didn't laugh the suggestion off, my friend looked at me more seriously, and asked if I would honestly be okay with it. Partly because I still harbored hopes that he would fall back in love with me, and partly because I was sick of feeling more immature than all my friends because I was the only remaining virgin, I just shrugged and said "Sure."

I took a few shots of the whiskey the boyfriend had swiped for the weekend to fortify myself (even though I hated whiskey). Then it began. I didn't really do anything. It was all done to me. In retrospect, I didn't give up my virginity; it just disappeared one night. We started with me making out with each of them in turn. Then, because I felt more comfortable with my close friend, he went down on me while I kissed his boyfriend. They switched places a while later. Then, the process was repeated, but with each of them penetrating me this time. The experience was not pleasurable for me, but it wasn't particularly unpleasurable either, so I continually assured them that it was great when they asked.

Finally, I told them I needed to pee. I dashed outside naked and ran across the ice to some bushes. As I passed Monica's car, I heard nothing; she and her boyfriend had gone to sleep. This reassured me that the boys in my car would probably be tired too, so I waited outside in the cold, hoping to hear my car fall silent soon. Eventually I was so cold that I was sure my nipples could cut diamonds, so I ran back to my car and hopped in, but insisted that I was tired and it was time for bed.

The next morning, early enough that we were sure our parents wouldn't have woken up yet, my friend caught a ride home with Monica and her boyfriend. As far as I could tell, taking my virginity hadn't made him madly infatuated with me again. I was left with the task of driving his boyfriend home. We stopped for waffles at a twenty-four-hour diner. In the middle of our easy chit-chat, he suddenly looked at me and said, "Seriously, are you okay? Do you want to talk about what happened or anything?" His sincerity was touching, but I brushed his questions off, all the while thinking to myself, "There's nothing we can do now if I'm not okay."

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.