Andrew / October 19, 2007 12:01 PM

Inspired by Time Out's current issue.

Mine was in the back of my parents' Aerostar minivan, my senior year in high school. It was not the best of times, but at least it was over with and I could start getting it on with a vengeance.

anon number 1 / October 19, 2007 12:55 PM

I'm not sure whether the first was in the Church confessional, or at that Boy Scout camp, I've repressed the dates and times.

anonymosity / October 19, 2007 1:01 PM

Where: My friend's living room floor (sounds trashy and disrespectful, and I guess it was, but at least I had the courtesy to wait until she was asleep in the other room)

When: '94-'95 New Years Eve

How it went: Me: "Ow." Him: "Gotta go."

What a waste of time. If I knew then what I know now (oh, such a grown-up thing to say), I would've waited until I was 25 before having sex.

Scrantonicity 2 NOT 1 / October 19, 2007 1:03 PM

Where: My friend's living room floor (sounds trashy and disrespectful, and I guess it was, but at least I had the courtesy to wait until she was asleep in the other room)

When: '94-'95 New Years Eve

How it went: Me: "Ow." Him: "Gotta go."

What a waste of time. If I knew then what I know now (oh, such a grown-up thing to say), I would've waited until I was 25 before having sex.

Sam / October 19, 2007 1:10 PM

Sophomore year, I was 15, and I didn't really like the guy that much. The summer between freshman and sophomore year I'd had this torrid love affair that resulted in a lot of making out, but no sex.

This guy had already done it with his previous girlfriend, so I figured, what the fuck, get it out of the way. We were in my parent's attic which was furnished and where us kids hung out.

It was uncomfortable and bad, and we never did it again. He started to annoy me, so I broke up with him two weeks later; his revenge was telling everyone at school that we'd "done it".

Moi / October 19, 2007 1:30 PM

Oh how I remember it so:

We were young and certainly falling for each other as newly turned leaved did from their trees in the face of a long cold winter ahead. Sly glances, rosy cheeks and fluttering hearts were the norm as we further became one. It was on a particularly cold fall night with most of the other students returning home from University for the weekend that we carved out our space in my dorm room. We shared music throughout the night and talked about art until we could do nothing more than gaze into each other's eyes. And with racing hearts we kissed and then as the sun of a new day rose we made love.

Ack! Cough, wha?

Freshman year of college in New York. My Dorm room and her Carlo Rossi. Awkward and short. Thrice more that week and we were no longer interesting to each other.

We laugh about it now- but both still blush when it come up.

Anon and 0n and on / October 19, 2007 1:41 PM

Sophomore year of college. I'd been lying for 2 yrs, telling everyone that I'd done it with a boyfriend in high school. This guy I'd been friends with for months was kind of a jerk but so hot! We had little in common but vast quantities of chemistry. And I'd just been rejected by his best friend. (Ah, those precious college years!) He'd just broken up with his "serious" girlfriend, so I was sure he'd done it! But, it turns out they were playing at being good Catholics, sleeping in the same bed and doing everything but fuck. He told me that part IMMEDIATELY after we did it. I did not divulge my deception and I've never regretted deflowering him!

charlie / October 19, 2007 1:43 PM

I don't "kiss and tell" but I will say that......

Foreigner was on the record player.

anon again / October 19, 2007 1:53 PM

Freshmen year of college. I met an upperclassman in the beginning of first semester and we dated on and off for the next few months. When we came back from christmas break we met up again. We did it finally in his apartment, on his futon, while shaggy's "it wasn't me" and oar's "crazy game of poker" played on repeat on his computer. It was after a night of underage drinking at a mexican night club. It was waaay short, but not very painful, and relatively fun in retrospect. We dated on and off for a few more months, but never slept together again, and that was it.

I had told him I wasn't a virgin before we did it. I'm curious if he could tell. Is that something that guys can generally tell?

anonima / October 19, 2007 1:55 PM

16, class trip to France, on the beach in Nice. With a guy from Tunisia. So stupid, but at least it was over with.

JAH / October 19, 2007 1:56 PM

Age `14, the sandy banks of Bear Creek, it was one of those crazy hot/humid nights that you only get in the south. With Wendy, the school slut.

Fun fact: I found out a few months later that she was one thing my best friends dad and I had in common!

anonymoose / October 19, 2007 2:13 PM

Junior year of college. We'd been dating for a few months and were in love. He had just come back from church (which I had skipped, bad kid that I am). Overall it was good, better than I expected for the first time.

The thing I remember most now was how his wool blazer was still on the bed and was scratching my leg.

Eamon / October 19, 2007 2:17 PM

She married me. I was JUST THAT GOOD.

Anon / October 19, 2007 2:39 PM

Well I was 25. It happened with my emotionally unavailable male roommate with whom I shared a crazy flirtation. We were both new to Chicago and lonely, and we went out for drinks and gave in.

I fell for him, like a 25 year old first timer would.
Of course we never became anything more. I don't regret it, at the time I thought it was the end of the world, and now it's just a story. I am glad I waited until I was 25, though. I would not have been ready earlier.

cashew nut / October 19, 2007 2:54 PM

i was fifteen, he was seventeen. he was the rocker type, a guitar player, with long hair and plenty of metallica t's. it happened in the back of his dad's chevette, parked in the middle of a cornfield. ah, decatur.

it hurt ALOT. at one point there was an exploding condom. i bled for a couple of days, if memory serves.

soon thereafter we were no longer speaking to one another. a couple of years later he apologized for being "such an asshole," but i think that was a ploy to get into my pants again!!

glib / October 19, 2007 4:08 PM

We were both freshmen in college. Both virgins. Both 19. I told her I was ready when she was. One night we went back to her dorm room and had at it. Three times within about two hours. It was pretty good.

Me / October 19, 2007 4:45 PM

Freshman year of college. In his lofted dorm room bed. We had been dating for the first two weeks of school and decided we were "in love."

It was pretty nice, all things considered. I remember wearing a matching Calvin Klein bra and panty set with gray tulips just for the occasion. After we broke up a few months later, I left that bra behind in some other boy's bedroom. Whoops.

kate / October 19, 2007 4:45 PM

I was 17, he was 19.

"Fever In, Fever Out" by Luscious Jackson was on.

It was pretty bad. We did it a couple times over the next few weeks but I figured out it wasn't supposed to be that awkward and we stopped "dating".

sexosauraus rex / October 19, 2007 4:52 PM

Still waiting....

ok, actually senior year of high school. she wanted to get "it" out of the way and I guess I seemed safe enough. Her garage. Lasted all of about three minutes. No completion. Almost got caught by my older brother who was coming back with his girlfriend who lived next door.

Second time was with brother's ex who lived next door... much better.

me / October 19, 2007 5:23 PM

I was 15, just shy of 16. He was my first serious boyfriend, and we'd been dating for almost a year. It was on the floor of my living room, right before leaving for school. He would drive to my house and take me school.

It was winter time, because it was still dark outside even though it was 6:00 a.m. or so.

I don't remember it hurting, all I remember is my boyfriend saying, "____, you're not a virgin anymore."

cinders / October 19, 2007 6:00 PM

it was this past may, i was 21, he was 27. we werent serious. he had joked about it a couple times before. we got drunk and did it on my bed. it hurt a bit and it was bloody. he regained conciousness a bit in the morning and asked if i had done it before. i shook my head "no." then he passed out for 8 more hours. ive only seen him once since. funny thing is, i dont regret it and i feel like society thinks i should.

Chutney Reader / October 19, 2007 6:25 PM

Post-prom hotel suite. I was 15/a freshman/a virgin; she was an experienced senior. It was sober, clumsy, and drama-free.

We weren't together for long, but afterward I didn't so much as kiss a girl 'til my junior year. Which of course at that age was an eternity. I'm not sure if "getting it out of the way" took the edge off, or made the enforced celibacy more maddening

? / October 19, 2007 6:38 PM

I actually can't remember my first time. I had sex with that guy so many times afterwards that they all started to blend together in one great big orgasmic blur. It could have been his back seat, or in the basement at my parents', or in his grandma's barn... that's right, we were (are?) country bumpkins. Where ever it was, it was good enough to do again, and again, and again...

J D / October 19, 2007 11:12 PM

In the grass @ "church" camp. (Young Life).
Ahh 1994.
We were 14.
Doing it in the grass isnt as romantic as hollywood would have you belive!

Claire / October 19, 2007 11:56 PM

I had just turned 16, and Jake was the only one who'd remembered my birthday. He asked me to Prom and I gave it up on the bunk beds. I hear he's a carpenter now. Just like Jesus was.

Claire / October 20, 2007 12:01 AM

Most depressing FUEL ever, btw.

anonymouse / October 20, 2007 1:11 AM

1998. i was 17. the former holiday inn in evanston, with a guy i met on the internet. this was back when meeting people from the internet still freaked everyone out.

i haven't spent time with him in real life since but we're still friends on the internet.

goner / October 20, 2007 10:31 AM

Freshman year of college w/someone I really didn't care about. The odd thing is that my roommate was doing the same thing across the room--about six feet away. I was unaware that this was going on. His girl later 'bragged' that she thought it was his first time. I never heard any complaints about >my

anonymoux / October 20, 2007 11:15 AM

unofficially, i was 19, he was 23. he was really tall and had an adorably giant nose. it was cold and uncomfortable in the backseat of my car, yet seemed like a fine idea regardless after a night of drinkin' & pot-smokin'. it wasn't technically successful, but it did leave me sore and walking like a cowboy the next day.

officially, i was 20, he was a year older. this time we had the comforts of a dorm bed. it was sweet; it didn't hurt, a little bleeding. then we listened to the super bowl shuffle on his computer.

ding / October 20, 2007 3:13 PM

when: i was 28; he was ... younger
where: summer, ann arbor
how it went: he cooked me dinner, we danced in the warm and humid night, we smoked, al green was in the stereo, it was freaking fantastic - the culmination of a summer-long seduction (his of me.) best. ever.

Anon / October 20, 2007 7:30 PM

I was a senior in high school and she was a junior. We'd been dating for almost a year and been good friends for a year before that.

We'd talked about it a few weeks before, acquired the necessary protection and waited for a time with enough privacy.

She came over to watch Super Bowl XXIX with my family, and at one point we went upstairs to "watch the game" in my room. My parents were always either cool or naive about that whole "going up to my room" thing...

Kaylee / October 20, 2007 8:03 PM

I had made some silly statement the freshman year of college about how I was going to be a 21 year old virgin because I heard someone say they were a "dying breed".

I'm a fairly determined person.

Lucky for me, I hadn't really wanted to "go all the way" with anyone I met until I was 21. Not that the guy I finally did lose my virginity was the best choice [he left me a month later for his ex fiance], but it went surprisingly smoothly. Aside from the horrible pain, there was no blood and he was really rather sweet. Plus, we had the whole house to ourselves, which meant we had about ten acres to ourselves.

RC / October 21, 2007 9:56 AM

College, sophomore year, bedroom loft, summer girfriend who came to visit. To that point, all acts of intimacy, every base on the diamond, had been a rock and roll party. She had about 3 years on me in terms of experience. In bed for about an hour, then the did the deed for 20 minutes (which I thought was pretty good at the time, considering friends had told me the gun would go off around the 2 minute mark during the first time). Was nice, lovely girl, however geographical distance and a lack of real desire for one another dissolved the relationship over the next six months.

Prior to jumping in bed, she put on the music, Carole King's 'Tapestry'. Perfect music for the event.

anon / October 21, 2007 3:48 PM

It was horrible! I don't even want to think about it. But I'm going to suggest to my friends with teenaged children to have the kids read the entries here and let them see how depressing the first time really is.

selective memory / October 21, 2007 4:06 PM

My more vivid memory is actually of my first real kiss. Summer after freshman year of high school, in the park with my first real girlfriend, laying on the grass. I went to kiss her, and was surprised when she opened her mouth. It was on the whole a softer and wetter experience than I had imagined. I managed not to be too forceful, and my mouth tingled afterward all night. She even let me feel her breasts and, IIRC, lick them a bit (ah, tube tops! ah, the late 70s!).

It lasted part of the rest of that summer, and never went much farther than that. Later when I was home from junior year of college, I had a fairly unsatisfying one-nighter with her (she was very small, very dry, and it was a bit awkward), although it wasn't a big deal. We managed to get each other off anyway, and no harm done and no hard feelings.

I sort of remember my first "real" time, which was during senior year of high school, but that memory is much fainter for me.

Nonny Nonny BuBu / October 21, 2007 11:16 PM

My sister's friend lived across the way in the co-op. She was also my best friend's sister and a three years older than I. I was home alone doing something weird like taking apart the toaster and putting it back together while in my bedroom. Miss thang come in the room and climbed into my bed and started asking me if I thought she was cute. I reassured her and moved forward to kiss her and we started making out. Then she asks me if I want to see the hair she has grown(?!) and I answer in the affirmative, with vigor. As I did my best clinical examination, she noticed the growing member in my shorts and freed the little guy. I instered tab A into slot B and that was my first time.
I was in the fifth grade.

ataraxy / October 21, 2007 11:42 PM

Maybe 15 or 20 years ago I realized I didn't remember exactly when my first time was. I know it was when I was in 7th or 8th grade, so that makes it sometime between the fall of 1980 and the spring of 1982, so I'm guessing circa 1981.

I had a boyfriend from the summer after 6th grade through the rest of grammar school, and we used to go to his house near school and watch All My Children and then fool around.

I can, however, remember with exquisite detail the first time with my fiancé as well as the first with the guy I dated for five years (and a couple other great firsts). Those are much more worth remembering!

ataraxy / October 21, 2007 11:44 PM

Er... we used to go to his house near school ON OUR LUNCH HOUR and watch All My Children and then fool around.

Do the Chicago Public Schools even let kids leave at lunchtime any more?

another anon / October 21, 2007 11:53 PM

my first time was when I was 25. I had dated this guy for the first three months of the year before he broke up with me. a month before I left for a year-long stint in london, we ended up getting back together. for some reason, I was bound and determined to no longer be a virgin. I basically had to convince him to have sex with me, which was not the reaction that I was expecting.

all in all, it was fine, but I honestly have to say that I didn't feel much. he was very thoughtful and it wasn't uncomfortable. we ended up breaking up three months later. even though our breakup was one of the most appalling I've heard of, I don't regret him being my first.

Mike Damone / October 22, 2007 9:55 AM

I was about 17 back in the early eighties when I walked Stacy home from school and she invited me to go swimming at her parent's house...

I got the feeling she more on her mind then just swimming, if you know what I mean. "This is some great iced tea," I told her in a reassuring voice to break the awkward silence and calm her nerves...

We proceeded to the changing room where we ripped each other's clothes off so fast I didn't even have time to take my socks off. If memory serves me correctly, I did pretty well for my first time--I lasted a good half hour at least and I could tell she was really digging it...

Of course, then she had the nerve to shake me down later for money for an abortion (apparently she had gotten pregnant) and vandalized my sweet ride when I couldn't come up with the funds. How's that for gratitude?

Vehicular Popsicle / October 22, 2007 9:57 AM

NYE 1987. Small town in Michigan. Chevy Chevette parked in the driveway of my HS drama teacher's house. Sub-zero and snowing like heck. A friend was housing-sitting for him, but he was jealous that I had a gal and reneged on a promise to let us stay there that night. The wine coolers froze. It was amazing.

B / October 22, 2007 10:00 AM

I was in my mid-30s before I had truly successful sex. I was married for a time, but we were unable to have full intercourse due to a physical condition that I had developed called "vaginismus." After our divorce, I finally got help from a physical therapist, so by the time I met someone new (a very kind, understanding man), I was able to have sex with very little discomfort. I would urge anyone who suspects they may have a sexual dysfunction to get help from your doctor. I know it's horribly embarrassing, but it's much more common than you might realize.

Jarvo / October 22, 2007 10:01 AM

Do you remember the first time?
I can't remember a worse time.
But you know that we've changed so much since then,
oh yeah,
we've grown.
Now I don't care what you're doing,
no I don't care if you screw him.
Just as long as you save a piece for me,
oh yeah

Enonymous / October 22, 2007 10:31 AM

Let me think... Oh. It was wintertime, as the party broke up. I was 17. She was 20, a friend of an acquaintance. We were blasted. She was sweet and a bit desperate (probably "getting it over with"). I was self-conscious and uninspired and treated her like garbage afterward.

She wouldn't recognize me, 'cause I'm swinging it now.

Anonymous / October 22, 2007 10:38 AM

December, 1991. I was 17 years old. In my bedroom listening to "The End" by the Doors. Foreplay & sex combined almost lasted as long as the song, a whole 10 minutes. Nervous as hell, but I wanted to know what it was like already.

mm mm mm / October 22, 2007 10:50 AM

I was 24. Chalk it up to a combination of Catholicism and a history of not dating guys I actually liked. But I liked this guy and I could tell, because we'd been fooling around up to different points, that he'd bend over backward to make me feel good and feel safe.

It was a Tuesday night. We watched a Netflix, went to bed and started making out. After he went down on me, I asked him to get a condom. He said "Are you sure?" (love that!) When I said yes, he dove for the bedside drawer. The sex was great and it just keeps getting better. I don't regret waiting and I definitely don't regret starting.

Nora Rocket is not shy / October 22, 2007 11:09 AM

Summer before my senior year of college. We'd been kicking around the previous year, first term, as I was abroad and he was dating an Other Girl in the second term. I picked him up that July for a week-and-a-half roadtrip from TX to CA and back. On the first night, he revealed the breakup with the Other Girl. On the second, we spooned all night on a friend's floor in NM. On the eighth, we bought a pack of rubbers and a pint of Cherry Garcia, put Portishead's "Dummy" on the stereo (with a brick on the lid to keep it closed and functional), and spent hours working it, on the pile of our shared sleeping bags that served as his post-college bed in that house.

Hours because, well, there was much to be tried, breaks to be taken, ice cream to be eaten out on the stoop, cigarettes to be smoked, and hands to be held as we lead each other back to the bedroom for another roll.

It was totally awesome and I regret nothing, even in the face of the secrets revealed later, the explosions waiting to happen between me and the Other Girl, and the absentee breakup that November.

Texas Dave, you punkass, wherever you are, you are appreciated.

anonapotamus / October 22, 2007 11:39 AM

we were best friends and i kind of woke up and we were kind of having sex and weezer was on repeat and the next morning there was a huge blizzard and we were stranded in the same house together and he kept talking on the phone to this girl he was sweating asking when she was goign to break up with her boyfriend so that he could take her out on a date all while i was making breakfast for him and that's what will lead you down a road of really fucked up feelings about men and relationships and friendships and truthiness.

anon / October 22, 2007 12:11 PM

we were both 15. laying in my bed, snow falling, everything silent except for the sound of us kissing and whispering. i asked if she wanted to- she bit her bottom lip, grinned a little and nodded yes. we both took everything off and rolled around on the bed some more. then i got one of my dumbest ideas of all times and decided i would really don juan it and up the romanticness by...turning down sex. I always imagined doing it for the first time in a hotel and told her something like "let's wait and make it Really special." Sybaris, maybe? Plus i thought it's what the guys in boyz II men might do. Blame it on tv: boy meets world, fresh prince- they all did it in hotels.

Really special turned out to be a week later at 3 in the afternoon in my parents uncomfortable bed after steve demanded 5 dollars to give us a ride and i told him to f himself on my front lawn. we went inside, got bored, said "eh, why not" then got down to it. Throw in a "i love you" on my part and a "jesus, don't ruin it" on hers.

Spook / October 22, 2007 12:11 PM

I got a late start. 3rd week of college freshmen year. I was the proverbial spook tossed into the cold, so when a beautiful older 22year old women who worked at the school cafeteria flirted with me in that thick New York accent, I was smitten. She wasn’t a student, and lived on the east side with her son. For 3 months, it was great. Missing home, on weekends I’d escape elitist campus culture for a ready made family.

I got to play good husband and daddy pretending I was raising a family while working my way through college. The boy’s real father was doing life for murder. She vowed her son wouldn't grow up like that.

It was the 90’s when crack cocaine hit the east coast streets like a tsunami and I’m sorry to say at first I enjoyed the crack culture vicariously. Instead of campus keg parties, she took me to seedy clubs including one she stripped at. Soon the novelty of “us” wore off. The clubs became dangerous, especially for an out of town college boy. For her the idealistic young leftist intellectual got old as flashy brash drug dealers like from New York’s Supreme Team, drove down to escape the heat. They tossed money around the clubs and swept up the “best” women. Violence soon erupted from the smaller local drug dealers who hated them.
One night my friend I were arguing because she kept returning the flirts of a young dealer from Harlem, when some other fool got into a fight over a spilled drink and shot the place up. The police arrested practically every one, but let me go with a warning after screaming at me, after I showed my college I.d.
Scared straight and we stopped dating, but stayed friends until around Christmas.

When I came back from break, she quit working in the cafeteria and became one of the kept women of Raful Edmonds who was the crack baron in D.C. I still have a picture of her all these years later. Man, she was beautiful.

Hazel / October 22, 2007 2:07 PM

Agreed, this is a depressing Fuel and I'm not gonna improve things.

I didn't know it'd be sex week here; I wrote the "Friends with Benefits" Detour piece but left out the more sordid details of course.

First time for sexual activity: 19. First time for what's defined as "sex": 29. Lots of angst in between, as you can imagine. The guy was wonderful and sweet so in ways it was far better than most "first times," although bizarrely painful.

Unfortunately we discovered, incontrovertibly, that something is really, really wrong with my body (like B's post above but probably not the same condition; it's inexplicable, physical, and NOT all in my head which is what I'm afraid everyone will tell me. Oh, and I can't afford to see a doctor...).

But hey, great to get it "out of the way" even if I ended up with a whole new problem.

B/S Monitor / October 22, 2007 2:34 PM

Spook...with all due respect...ahem...bullshit.

:-)

Spook / October 22, 2007 2:52 PM

B/S Monitor,ahhhh a jealous midwest hater,
" hate hate hate hate hate"
:-) never willing to step outside their vanilla comfort zone especially for "Love"

But I guess you also know what's fake because you also lived on the east coast during the late 80's early or 90's. I'm sure you even know what Go Go music is or was.

B/S Monitor / October 22, 2007 3:07 PM

Hmmmm...Interesting response.
Honestly, Spook, I expected something more from you.

I mean a person of your experience and education (both scholastically and in the "school of life").

You kind of let me down with your response, oh wise one.

:-)

Spook / October 22, 2007 4:40 PM

Monitor, son!

Why you get me started! Now I can’t resist!
kid! Back when, I was sooo East Coast! Yea I was all about the east coast hip hop
like the Wu Tang Clan is all about the Asian culture, son!

Like EPMD said “cause we was in there, cause we been there, now we otta there like LaGuardia”

Yea you know I had the "Kid N’ Play hi-top fade" and I was listening to the Doug E Fresh “La di da di, we like to party we don't cause trouble, we don’t bother nobody.”

Yea, I was there for the Go Go Music craze too! Not to be confused with the midwest “Bucket Boys” stuff. But I didn’t like the Go Go. As you can see, I was all about the east coast hip hop!

Man I miss it, ahhhh youth like Ahmad said in Back in the days

“Back in the days when I was young I'm not a kid anymore
But some days I sit and wish I was a kid again”
The only bad thing about the East Coast was the lack of BBQ joints, but rumor has it that more are popping up in the NYC!

Happy Monday, yall

p.s back to topic, what about Allan? Where, when, how'd it go?

and is Fluffy gonna take a pass on this? Was it with "Mini Todd?" her arch enemy!?!

your mom / October 22, 2007 4:51 PM

My first time was also with someone from the internet, back when Internet dating was only for geeks who couldn't get laid like myself (1997).

He was a young strapping computer tech of scottish decent and I was a chubby nerd a few weeks shy of my 18th birthday. We had a phone / chat romance for most of the summer after my senior year and towards the end of the summer, I flew out to see him.

We mostly fooled around in a hardcore way most of the week that I was there until the last night of my stay where we got a hotel room, some white zin, and a box of condoms.

He was a big boy, but It only hurt a little bit and I got over that pretty quickly. He lasted much longer than I anticipated and we were like rabbits for the rest of my stay. It was later in the evening when I realized that spermicide makes your mouth go numb. Good thing to learn early I guess.

We dated long distance for 2 years and spent the summers and holidays together. We taught each other how to be sexy and l learned a lot about myself and about men from him. I've since moved on, but I still google his name on occasion when I'm feeling nostalgic.

skafiend / October 22, 2007 4:55 PM

Spook...

G0 Go = "Doin' the Butt..."

Good times...

and your story, whether greatly embellished or true, seems like it's ready to be turned into a movie. Have your people call Larenz Tate's people...

Too Soxy / October 22, 2007 4:57 PM

Growing up Smiths really messed me up in the head viz a viz sex. Morrissey just made it all seem so...victimizing.

I lost my first attempt at a girlfriend at age 15 in part because by the time I tried to kiss her, she'd figured I didn't like her that way and decided that she didn't like me that way anymore. But we always had that brief spate of hand-holding!

Age 16, my girlfriend and I journeyed to third base back when third base meant a bit less than it does to today's kids (that is, hands were use where mouths so often are nowadays). Several times, we played around with each other's fun bits and did ye olde humpus dryus before her Catholic guilt freaked her out and we broke up. I swear, a whiff of Obsession still gets the loins a-stirrin', though.

Then it was years and years before any real action came into my life (somewhat ironically, with a very lusty Morrissey fan) after years of misery and striking out. Apparently I wasn't that bad, as she had no idea that she was my genuine first -- must've been all those tips I picked up from Penthouse Letters or something....

anonymostaciolli / October 22, 2007 6:54 PM

Freshman year of college. My high school girlfriend stayed in state, I had gone out to the east coast. She broke up with me after a month or so and started seeing somebody else immediately. When I came home for Christmas break, all of a sudden she wanted to get back together, and was ready to do it.

It was on the couch in my basement. The creepiest part was that it was while we were watching The Bad Seed.

She broke up with me again once I went back to school. Then got back together with me when I was home for spring break. Then broke up with me again. Oh well.

Helen Keller / October 22, 2007 11:04 PM

I dated a fat guy because I didn't want to be superficial and write him off, and I thought he would be a "good person". He really wasn't, he ended up being physically abusive. I was 16, he was 19, and so fat he crushed my 112 lbs and I couldn't breathe. Plus there was a lot of chub around his wiener that made it shorter and not easily accessible.

He freaked because I didn't bleed and accused me of not being a virgin. Whatever. Guess he wanted to hang our sheet in the town square. He fell asleep and I went in the the other room and gave myself an orgasm.

I stayed with him for a year and then, feeling I payed my karmic dues, moved on to a smokin hot Marine with a rock hard body and a baby's arm between his legs. Sweet Jesus things were good, and have been on par ever since.

Ask me about the sex I'm having in my 30s....holy shit it's mind blowing.

More please / October 23, 2007 12:42 AM

Mmm. Helen, I'll ask... How is sex in your 30s? Please share!

you can probably guess / October 23, 2007 12:51 AM

I was 24. The guy in the next door apartment, a manager at the Greyhound Bus station downtown (yeah, it was THAT long ago), had spotted me partially naked and informed me about it. One thing led to another & a few days later I lose my virginity as TV reporters broke the news at the 1980 Republican National Convention that George Bush was going to be nominated as Reagan's vice-president.

Well, the stars did not fall out of the sky and the guy was one of these "don't have 'em in your bed any longer than it takes to fuck 'em" types. So I'm back at my place at 10p, feeling that it's too late to do anything else that evening, and thinking, "My mother made me neurotic about sex for THIS???"

Helen Keller / October 23, 2007 9:21 AM

only if Gaper's asks. perv.

random / October 23, 2007 9:30 AM

15, back seat, country road, beautiful Mexican boy. both virgins-

the making out was always yummy and we did it everywhere, all summer. the sex, meh, but it was the start of something really great. sex, that is.

The relationship with that boy ended when high school started again. He broke up with me to go out with my best friend. Man he was cute.

More please / October 23, 2007 9:31 AM

Ah! Helen (Fluffy), I am not a perv. I am worshiping you as a heroin! :-)

More please / October 23, 2007 9:33 AM

I meant heroine. Sorry!

Ramsin / October 23, 2007 9:52 AM

Dear Gapers Block,

I never thought I'd write a letter like this, because I never thought this would happen to me. When the United Nations Bottle-Swallowing Kegel Masters Team moved in next door to my parents, I didn't really think much of it. Occasionally, I would go over and mow their lawn or help them install their mirror wallpaper or self-cleaning bearskin-and-satin carpet.

But the summer before I turned seventeen, when my parents went on vacation to Somewhere and I was all alone, everything changed.

One day I was out on the front lawn, doing my usual early-morning power squat thrusts when I felt twenty eyes on me. I innocently looked over with my big brown doe eyes, and was met with the hungry glares of the United National Bottle Swallowing Kegel Masters Team...

fluffy / October 23, 2007 10:24 AM

I'm not Helen Keller....sorry.

But here's my story: I had the biggest crush on this guy in college. I had messed around with other guys but never went all the way- no matter how turned on I'd be, it just didn't feel like the right time. So, the crush started responding and we began dating..we didn't 'do it' until I went to visit him in MI and stayed with him. He was a hot jazz drummer and we did it on the lower bunk bed in the bedroom he grew up in. It only hurt a little - no blood or anything but he was huge. Afterwards, he told me he loved me. That night, I met his Mom for the first time at dinner at a fancy restaruant. It hurt to sit! But I felt so special. cheesy, huh?
Anyway. we were together for a looong time after that - we're still friends.

Abby / October 23, 2007 10:27 AM

I was painfully shy in high school and college and had never had a boyfriend, just passionate crushes and stupid Amelie-style attempts at getting their attention. Finally I crushed hard on a guy and was determined that he would be my first. I was 23 and hated my virginity. He was 27 and very cute, friendly and safe-seeming.

I asked him to model for me one Saturday afternoon (I was an art student) and he agreed. He came to my house and I sketched him a little. He offered to get naked and then did. I painted him for a while and then approached where he way reclined and sort of got in his way. Things moved along quickly then. He looked terrified but laughed when I told him it was my first time. It was OK, not too painful, not too much blood. I convinced myself that I was in love and we got married three years later. Only after we split up ten years later, did I start having really good sex. I wasted so much time!

skafiend / October 23, 2007 10:49 AM

Two observations:

1. I am slightly surprised at the number of people (mostly women?) who didn't lose their virginity until their mid 20s. but I guess that's just me.

2. My favorite exchange:
Helen Keller: Ask me about sex I'm having in my 30s!

More please: Ok, I'm asking.

Helen Keller: Perv!

LOL

anonportunity / October 23, 2007 11:09 AM

anyone who commented that early sexual experiences sucked but now find it to be a wonderful, zesty enterprise- wear a blue bandanna in your left back pocket @ the next gb meet-up. those still unsatisfied in bed and would love fellow gapersblockers to teach them their passionate wisdom- wear it in the left.

red bandanna in left pocket for those who feel like they wasted time having bad sex in boring relationships. red in right pocket for those wishing to help them forget all that, like Tonight.

yellow in left if you're r.kelly. yellow in right if you welcome pee in your love life.

if you're spook- tie the bandanna around your face to compliment the beret and viva la revolucion. if you're a slender male art-thug with a bandanna around your neck- immediate ejection back to the places w/ no sidewalks.

ramsin / October 23, 2007 11:14 AM

Uh...this thread is getting Real Sex swinger party creepy.

Andrew / October 23, 2007 11:45 AM

Speaking of GB Get-Togethers, the next one is this Friday, 10/26, at Green Eye Lounge. We'll be there from 9pm till about midnight.

If you show up with a bandana, we'll laugh at you. :)

anon4 / October 23, 2007 12:21 PM

if you get bill clinton-style technical, my first time was senior year of college (so i guess i was 21) with a guy i had been dating most of the year, in his dorm room twin bed. it was pretty unexciting - he was kind of very underendowed, but I didn't realize it would make as much of a dfference as it did.

(in a non-techical way, i had a lot of "everything but" in high school that was a lot more fun and physically rewarding.)

lolo / October 23, 2007 1:18 PM

Me: 18, her 17. We had met through a mutual friend. She had an eye & designs on me, and I never would've guessed. She persued me, invited me over to her house, assertively and impatiently moved things along until we were on the back porch getting busy on the patio furniture. Yeah, we ran a big risk of being busted by her mom.

We were heavily involved for about a year thereafter. She was my first, but was waayyy more experienced than myself. It was a turbulent, effed-up relationship, and we were incompatible in most emotional respects. When we had breakup sex, she cried. But we continued to hook up occasionally again & again, because despite everything, we were completely compatible sexually and couldn't find each couldn't find another lover who even came close. And, over all these years, I have to admit that I still haven't.