How Did You Lose Your Virginity?

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I had just run away from home again and was staying in my best friend Mike’s parents’ basement. (You can see Mike and his half-fro at top-left.) We all worked at the local McDonalds. One of our managers was a girl who had moved from California to Kansas City, in sort of a reverse late-teens flight from what she’d known; apparently when you can’t go any farther west, you go bounce back east. Poor Californians.

Her best friend was a girl named Sunny, who came out to visit and stay for a few weeks. At the time, despite the whole running away from home business, I was a pretty straight-laced kid—a literal choir boy. Sunny had purple, spiked hair and a lip ring. All my friends at the time thought I was horribly lame, but Sunny took a shine to me, finding my capacious knowledge for showtunes attractive, especially since she’d only recently vacated the beds of a series of typical post-high school punk rock assholes who treated all the punk rock girls like shit, since the girls weren’t the cheerleaders and prom queens they all craved.

Sunny had huge feet. I kissed them one night on a tube slide in the middle of a park. We went back to the rented house she shared with the McDonalds manager, stepping around cat turds and bongs. She filled up an old bath and invited me in with her, but I was too nervous to do anything but lean over the side and pour water over her from my cupped hands. I fingerbanged her on the couch with ignorant tenacity for about half an hour before she pushed my hand aside, took a swig from a two-liter of root beer, and mounted me. Amazingly, despite it being over in seconds, my previous clitoral doggedness had primed her pump, and she had her first orgasm there in my lap, or at least that’s what she had the courtesy to tell my friends.

She called me about a year later and said, “Guess what? I’m pregnant!” It wasn’t mine, but instead the child of a “really dumb, beautiful” Mexican man she’d be dating for a while, but who had already split.

Sunny wanted to be an artist—specifically, an animator. This was the inside cover of her notebook, which somehow remained in my possession when she went back to California a few days later. She gave me an unused train ticket and told me to come out and stay with her for a while, but I couldn’t be sure of myself, and stayed in KC for several more years before I, too, got the gumption to go east.

Last I heard Sunny had two children and had joined the Air Force, but I lost her number, so the only updates I got were through a grapevine of unreliable fidelity, until they stopped entirely.


33 Responses to “How Did You Lose Your Virginity?”

  1. 1 Kat

    !!! I was just thinking about this (my virginity, not yours) last night, because I wound up having sex while watching the same movie I lost my virginity to, Goldeneye. He was the manager of the video store I worked at in New Orleans. Part of my reasoning was that he was super nice and leaving for the Army in two weeks, so there was no way he’d have a chance to break my heart, unlike the supreme douchebag waiter I was in love with at the time. Like all of my stories about new orleans, this one has a sort of epic, depressing ending that’s probably better saved for another time.

  2. 2 tec

    I lost my virginity in a room full of teenagers (us, one other couple who were also going at it, and my poor friend Danielle in between us) at a pagan festival, to a punk kid four years older than me (yes - statutory) with a super tall mohawk who gave me a Skinny Puppy tape and kept calling me until he went to prison for dealing coke.

    You know, summed up like that it sounds much sleazier than I remember it being…

  3. 3 Phil

    I was two months into college when i began to go out with a slightly older girl in my dorm, which had lots of older students. She was a flute player, ensuring that my friends were able to make all sorts of clever jokes when ‘American Pie’ came out. Hooray. Then I spent the next four years overhyping the experience and the following break up all out of proportion. Was really annoying. Didn’t get laid during this entire period. All in all, a total fuck up.

    But I’m better now. Really.

  4. 4 Jim

    I actually lost my virginity in the garage of my then girlfriend who had been crushing on me since 4th grade. We both went to two different middle schools, but she still had a thing for me during the time (apparently keeping tabs on me through friends in my school, and watching my wrestling matches and other activities which where combined teams.)

    Come high school we met up again, both being ROTC cadets. She was a shy goth girl who was finally breaking out of her shell. We hung out a few times, made out and started dating, and then a month into the relationship we where in her garage (which she had like pillows and sheets and candles and stuff in to hang out in) and we had our first and second time. Ended up going at it for almost a hour and a half with me going down on her in between which was ALSO the first time I had done that. We banged like jackrabbits after that, anyplace anytime, but it started becoming almost like that was all our relationship was, having sex.

    In the end a year later she left me. She got to a point where even I held her back. She had some major issues, parents where both blind, where a former priest and nun, and the whole family had run away from Arizona where they where being stalked by people who her dad had turned in. She got into drugs and became bisexual (though I think more for fun that actually liking women) and has dated slimeballs since.

    I saw her again a year ago, we went to get coffee. The garage was torn down by the city, she was dating a real asshole I knew from college, and had recently lost her license for driving drunk with weed in her car and hitting 2 cars. Kinda sad cause I remember the shy little girl who was a A student and a sweetheart to everyone, and now she cant even keep a job at the mall, and is so damaged that no matter how many times she said such and such is a wakeup call she still does it. About the only thing I think shes not doing i hard drugs now.

  5. 5 andrew

    My first time was on my sisters birthday a few years ago in a hotel room my gf and i rented. it wasn’t our first try, but her being very small and me being 6′3″ some things dont seem to equal out. we dated for over 2 years and she recently dumped me to make it so that i could pretty much sleep around and live the college life and her not get jealous.

  6. 6 adam b

    mine is kinda weird. i was a junior counselor at this southern baptist summer camp i had gone to as a kid. at the time, i was actually christian, though in the super liberal way that my parents still are. in any case, i was a junior counselor, and so was david, who i had been a camper with for about 4 years. we were both teaching indian lore, which was pretty much just making stupid stuff out of beads. i had figured he was gay, and i was sure i was. we always had the same day off, and we would hang out. one night, we got back to the camp early, and decided to hang out in the crafts building. ended up fucking. we had no idea what we were doing, so it was not exactly great, but it popped the cork, and led to me figuring out a lot more about sex.

    so, two 16 year old male counselors at a southern baptist camp. it was my last summer there, after bitching out a fellow counselor about her insane, reactionary views and being asked to not reapply for a job. which sucks for them, because i was a really good counselor.

  7. 7 Rye

    My first time was with my wife about three months into college. It was awkward, short and repeated three additional times with little improvement. I guess there’s something to be said for experience though ’cause we’re still at it 7 years later, LIKE RABBITS BABY!!!!! Sorry.

  8. 8 Travis

    I lost it to Sportscenter. I don’t remember what was going on in the world of sports that day, but it was in the middle of the summer so it had to have been shitty baseball.

  9. 9 Deadgirl1121

    On the floor of a shower in the girls locker room in the basement of my church. Yes, I lost my virginity in a church and I wouldn’t have it any other way.

  10. 10 Jon

    At my best friend’s graduation party. We all had tents set up in his backyard, apparently we weren’t as discreet as we had thought we were…

  11. 11 andrew

    jons is my fav, i hate those times.

  12. 12 Rev. Spencer

    I was 17, and it was spring of my junior year. A girl one year my junior but worlds more experienced in sex just moved to Kansas City from Wichita. I was floored that a girl that cute approched a geek like me and wanted to date. Finally I got up the nerve to ask her to do the honors, and she gladly accepted. One night I walked to her house after my folks went to sleep to meet her. We decided we wanted a proper bed so headed back to my house. Half way there, a thunderstorm opened up and drenched us. We ran home through the downpour and snuck in. The first interlude was over quick, followed quickly by round 2. The whole thing would have been an awesomely romantic even, had I not forgotten to pull out the second time. She freaked and was super pissed. Fortunately nothing came of the mishap, and we had an awesome summer. Things ended at the end of the summer, but it was good times. If my parents knew, they never mentioned it.

  13. 13 Alex

    It was during summer school right after my freshman year of high school. It was my 15th birthday. Third best birthday present I ever got. It was with a girl whose mother lived in my town, but she spent the rest of the year with her father in KC. Her name was Kim Millenson.

    I exited her bathroom to find her standing on a green bedsheet on her floor. She was wearing a pair of black satin panties and nothing else but makeup. It was immediately then confirmed that the muffled “do you want to have sex with me,” which I’d sworn I’d misheard through the door moments earlier had not, in fact, been misheard.

    I’d never had a conscious orgasm prior to that afternoon, and when the big moment arrived, I was completely stunned. I clearly recall exclaiming, “Oh my god! What did you do?!?!”, and she was like, “I think you came.” I felt too awesome to realize how stupid that had been.

    A year later she was back in town again. She was pregnant from some guy and needed money for an abortion. I bought her Rickenbacher 4003 for $300 bucks, and that’s how I got into music. The next year she was engaged to some other guy and wanted one last fling through the city. And the next year I was one of only two friends that she invited to her wedding.

    The last time I saw her, she was pushing a stroller through the streets of New Canaan, CT. Random encounter, yet strangely on my birthday again. I looked down and asked what her beautiful baby’s name was; she answered, “his name is Alex.”

    I will have at least a one fleeting memory of her every year on July 17th until the end of my days.

  14. 14 Blip

    My first girlfriend, 7 years older, on my own very narrow bed, on my 18th birthday. She’s still a friend.

  15. 15 James kelly

    How come when Alex tells a story it sounds like something out of a movie :) And why do I picture Molly Ringwald in it? Could be my long standing Sixteen Candles crush on her…

    My First was at the ripe old age of 14 (she was 15).. and in my parents bed while they were down the street at my aunt’s and uncle’s place. We were too young, and I was freaking cause I was actually gonna have sex! If was brief, did not have a CLUE what were were doing, had some issues hitting the “target” at first.. and then the condom broke.

    I remember at the time Flipping out, because I was certain she was going to end up pregnant, not helped by the fact that she was late that month…thinking back, I remember that I never even got to my “O” face,…. was sad and pathetic and scary.. and 4 more years before I did it again…

    J.

  16. 16 Jim

    Yeah I was about 14 going on 15 for my first time. She was 16.

  17. 17 Dave

    I was 22, working at summercamp deep in the mountains. My college girlfriend had just dumped me. A local girl, a Mountain Woman, who worked in the commisary picked up the pieces of my broken heart. One night we drove up to the summit, took a sleeping bag and jumped a No Trespassing gate and did it overlooking the sleepy redneck hamlet twinkling below.

    She later felt guilty about stealing my innocence. She was probably onto something considering that I am now an insatiable sex fiend.

  18. 18 tec

    Alex said “I bought her Rickenbacher 4003 for $300 bucks,”

    Holy shit, man! The rest of your story was sweet, but I had a hard time getting past this. Do you still have it?

  19. 19 cdan

    We were friends. She was engaged, getting married in a few months after graduation. I knew she had had a crush on me for a while - there had always been some drunken flirting going on, but one day she leaned over and kissed me, and said, “I’ve wanted this for a long time.”

    The image of her taking off her engagement ring and setting it gently on the bookshelf will always be burned into my mind.

    It was horribly awkward. I didn’t finish and tried to fake it (hah!). I don’t think she bought it because she came up the next night to try again. Still awkward. I told her we couldn’t keep doing this, etc. She agreed.

    I’m sitting here thinking how much I would pay to go back to that night. Right now, I think I’d give around $5k.

  20. 20 macpherson

    just to prove that it does happen.

    aged 25, our wedding night. worth waiting for. totally. for both of us.

    since then it just keeps getting better. 19th anniversary this year

  21. 21 Rye

    Well I guess that marriage was built on a solid foundation.

  22. 22 Ryan

    I was 13, she was 14. A bit on the young side, but at the time it felt like it should have happened sooner. She was all super Christian or whatever, so we would make out but never get past about third base. Then, some six months into the relationship (and after much prodding and pleading), she agreed to have sex with me; but only if I loved Jesus more than I loved her. Naturally I was like, “of course I love Jesus more than I love you!”

    We broke up shortly thereafter.

  23. 23 andrew

    “It was horribly awkward. I didn’t finish and tried to fake it (hah!).”

    i’ve tried before it doesn’t work out to well.

    “aged 25, our wedding night. worth waiting for. totally. for both of us.”

    the girl i’ve liked for like past 6 years is waiting i believe, and if i could talk her in to marrying me i would have gladly waited with her.

  24. 24 macpherson

    andrew- don’t talk; ask. and if she wants to wait; wait. sex is great but not worth trashing a great relationship over.

  25. 25 andrew

    i’m 21 i dont need to be marrying anyone, and anyway i ask her like once a month

  26. 26 ThinkandDrive

    No deets. But I will tell you that I got a speeding ticket on the way over to my girlfriend’s house. ;P

  27. 27 Scott

    I fell in love with this girl when I was 14, she was 13. She was my best friend’s cousin. We dated for about a 6 months, and we did plenty, just never went all-the-way because she didn’t want to just yet — fair enough — we were really young.

    After we split we remained very close friends, but we both were dating other people. I was dating this girl from school, and we both worked at the same tanning salon. We ended up doing it in one of the tanning bed rooms and it wasn’t great so I guess I kinda messed up my chances for something special. But…

    Me and the girl I fell in love with when I was 14 dated on and off through high school and beyond into our early twenties — still no sex — it’s not like we weren’t doing it with other people, it just didn’t seem right to be doing it with each other…

    I’m now 34 and married to my aforementioned first true love. We didn’t wait until we got married, but we did wait over 10 years; and I gotta tell ya, it was worth the wait. We often wonder if we would have ultimately ended up married had it not been for our abstinence with each other. Not that I condone abstinence (trust me, it wasn’t *my* choice), but sex can really screw up a relationship if you’re head’s not in the right place…

  28. 28 jenny soul

    i was 18 and although i was drunk and i’m not likely to see the boy again, i do not regret it one bit.
    we were at a concert, id had a bit to drink and was enjoying watching a gig onstage. i reconised a boy who went to my school a few years older and we got talking, and ended up walking round till the early hours of the morning laughing, catching bubbles and enjoying the festival.i cant stress enough the connection we felt, the fun we had and the sudden rush of ecstacy i felt just being with him. the conversation never stopped. we ended up in his tent cos it had got cold, and i gave him a kiss. we started snuggling, just enjoying each others company and one thing led to another. i remember getting that thought, oh my word ‘its now’ but i sort of reveled in it. all ym worries about it had gone. outsde it was zero degrees but somehow i was nice and warm inthe tent! he was kind and gentle, but strong. we both came, and i ended up alseep in his arms. in the morning it was quite surreal.we couldnt really stop giggling. i knew it was not the sort of thing either of us would do, i had not even had any other sexual experiences other thn that. he was a very polite (and handsome) oxford boy, and gave me his number, and texted me a few times that day.
    that night, the next day of the festival…. it happened again. we discussed it before hand though, and what it would be longterm. we both go to uni at different ends of the country, and decided it wold be a nice one (well two off).
    i know that this guy is a good friend, we have had some amazing talks and we both wish it could be more.
    so i dont regret the fact i only knew the guy for 3 or so hours before we did it. i believe some people just click.i loved being with him and he loved being wiht me.
    i only hope the next time is wiht someone i respect and enjoy as much as him.

  29. 29 Annna

    I was 16. I promised my sister I would wait till I was 16 and that’s what I did. I had pictured it with someone who I would’ve been with for awhile. But my buddy has his own appt and there’s a party there just about every weekend and I had been going to these for quite some time. Never hooking up with anyone. Then one night one of the guys that lived there just decided to be like” heyyy what up girlie.” Haha Started with simple kisses then cuddling then to wating till everyone got out of the room and racing to lock the door. That being done, I lost it. The condom broke i guess, but luckily he was a tad bit drunker than I was so he didn’t bust. Thank jesus! But then we just got another one haha. And ya know even being drunk I was still fully aware of what I was doing. So kiddo’s don’t believe the “I was drunk I didn’t know what I was doing line” And we talked a lot after and how he wanted to keep talking and made sure we had each others numbers and so ons so we texted like a day later, then…like 3 days later, and…not at all anymore, So I’m not sure what to think of it? I kind of regret it but the way I look at it, There is no changing it so why the hell sit here and be depressed and think why aren’t we talking? I got laid bitch!

  30. 30 caleb

    I was 15 when I lost my virginity. It happened when my friend and me were walking around town waiting for our friend to pick us up for a party. After we got picked up our friend who was driving told us that he had to stop by his girlfriends and pick her and her friend Hannah up. We got to his girlfriends house and Hannah kept whispering back to her and I was nervous about what she was saying because I was really stoned when we got there. We went to the party and me and her talked and made out a bit. She told me how she thought that I was hot and asked me if I wanted to hook up for the night. When we left the party Hannah came to my house because my mom was gone for the weekend. We got to my house and had sex then hung out for a while the next morning before her friend picked her up.

  31. 31 Lisa

    I’m 18, and still virgin! I been going out with a guy for 2 years and we always break up and go back together since he moved from the country but we’re nearly breaking up AGAIN. The reason for this is my parents are so annoyingly overprotective and he wants me to go to miami with him paying my ticket, but it’s just not possible. It’s kinda sad the reason we have so much prblems. I just hope my first time is after Im married or just with the guy I’ll b spending the rest of my life with.

  32. 32 Maryam

    I lost my virginity to my father when I was 13. Better said, both of us agreed to transfer it to him… Let it be said that there are many different solutions to this age old question. Not all are appropriate for everyone. Do as your heart tells you and don’t let anyone pressure you to surrender yourself sooner or later than you’re ready. Your sexuality is a wonderful gift, use it wisely.

  33. 33 Sarah

    i lost my virginity when i was 16,
    my friend (whom today i know is a liesbian) asked me to come over one night,
    i thought yeah just a normal night, when i got to my friends house though,
    she was full like yeah lets go watch a movie (her parents were out for the night),
    she went to choose a movie when she came back she was wearing nothing but
    panties :O
    i was like what the hell are you doing, she told me that it was normal and that she’d done it with plenty of people in our year, so naturally i followed along.
    We started making out, it felt kinda weird making out with another chick but meh,
    she then grabbed my boobs and started to twist and turn them, for some reason it felt kind of good, i was rather surprised.
    so in return i grabbed hers, then she stoped and slid her hand down my pants :O
    i was like !!!!!! what are u doing and then she pushed me back and told me that its ok, everyone has done it, its only natural.
    she started to finger me up, she slid my pants down, then my panties and started to lick my clit.
    this was the first time anyone had ever done this, i hadnt even touched my virgina in that way before, but the sensations that went though my body omg it was soo good.
    i let her continue to lick and fingure my pussy, i felt a drip go down my leg and then i realised that i was all wet, i was like ? why am i wet, then she explained everything
    she then took off her panties and started finguring herself, she asked me to do it, i slowly slid my fingure into her virgina, it felt sooo weird at first but after a while i liked it. after i got used to it i stuck my tongue in her pussy, i wasnt really sure what to expect but her juices actually tasted nice, i continued to lick her and fingure her at the same time.
    she then got me to stop, she got up and went out to get something, at the time i didnt know what she was doing but soon i realised, she came back with a dildo.
    she sat back down on the bed and started to push it inside me, i pulled back with agony. she then pushed it inside herself moaning as she did it, i was interested but scared. it looked as though she was having soooooo much fun and that it felt soooooo goood, i grabbed her hand and brang the dildo over to my virgina, i told her to do it gentlely, she slowly inserted it into my wet pussy, (most guys dont know this but for some girls first time sex hurts) as she pushed it inside me i allmost cried, a small stream of blood dripped out of my virgina.
    but after a couple of time inserting it in and out the pain cleared away and i could feel pleasure :D, that night i had 2 orgasms, i was having the time of my life and it was with another girl :P
    i will never regret that night and without it i dont know where i would be today
    it was the best thing i had ever experianced, that was the night that i lost my virginity, to my best friend, we are now dating (im bi-sexual btw), we’ve been going out now for 3 years and i will say that lesbian sex (no offense guys) is way better than having sex with guys, we know where to touch each other and where to lick,
    if u want to try it dont be affraid, its the best thing you’ll ever do in your life
    i agree with maryam, sexuality is a wonderfull gift

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