When we asked for the best stories about the first time you had sex, we knew there would be some weird offerings. And there definitely, definitely were.
There was more than one international affair. There were people who knew their relationships were doomed because "he is a spooner and doesn't believe in air conditioning which is a lethal combination when you live in the tropics." We learned that there are "sexual vampires" out there. People have sex in the woods and then walk through cow pastures. There are plenty of caught-in-the-acts. Condoms are left on for far too long. A Beer Lady. Blue vibrators. Men who reach orgasm "while looking dead into Tom Hanks' eyes." People having sex in closets at a Christian camp. Dead Heads.
But there were also amazing stories from people who described feeling accepted for who they were for the first time, from people who found this post to be a great opportunity to be honest about their sexual past in their quest for sobriety and people who, after dealing with sexual assault, found someone to love them consensually and without conditions. To those people: right on. Your stories are "the best" in a very different and more heartwarming way than a lot of the stories we're about to feature, and in many ways, far more important.
But with that...
Pillow Talk via SwissLube
Age: 20 (Junior year of college)
Location: His apartment
Partner: 28-year old Swiss guitarist in my roommate's band
How it went down: The foreplay was amazing. I was on the last day of my period so I told him he didn't have to perform oral sex on me. Before he entered me for the first time he said (in a thick accent), "First I am going to put on this Swiss lube and then I am going to go inside of you". I was so tight (I couldn't even use tampons before losing my virginity) and it hurt so bad that I started crying and I kept making him stop. He then said "I kind of want to put a pillow over your face". I begged him to let me fellate him to orgasm just to make him stop and then I went home to my house where my 4 male roommates were playing Halo. They all high-fived me and then I went to bed.
Talk About A Big Lebowski via Buggie in June
Age: 20 (1 week before my 21st)
Location: His bed, in his house he shared with 7 other dudes. His room was the attic.
Partner: boyfriend, who continued to be my boyfriend for the next 3 years
How it went down: The Big Lebowski was on. We had sex. Then I cried and stared out the window (it was raining) for an hour. Jesus wept. That was the night conservative right wing Buggie started to die.
The Orthodox Virgins via therespizza
Location: King suite of a fancy hotel in downtown Baltimore
Partner: Very recent husband
How it went down: It was our wedding night, and despite having done damn near everything else, we had agreed to save the coitus, the final frontier, until we were married. We're Orthodox Jews, and hey, this was how we justified the everything else. He wasn't a virgin, having gotten religion in college after having his share of partners. I was, technically. After the wedding, still in our dress and suit (respectively), we drove over to the fancy hotel my parents graciously paid for (which is kind of weird in retrospect). I told him I had to "slip into something more comfortable", then went into the bathroom and got into a pair of fuzzy pink footy pajamas. I came out and did a striptease to "Natural Woman". I simply couldn't take this whole "deflowering" thing seriously. We commenced the consummation, in the bed and in the bathtub. I remember being underwhelmed, but knowing we would get better with practice. I didn't bleed, and it didn't hurt. I didn't come until we resorted to our usual fingerbanging - the clit wants what it wants, what can I say. Then we snuggled and watched Family Guy (which totally was still funny and not lame back in 2005), and ate leftover wedding food. It was perfect.
He's No Nathan Fillion, That's For Sure via blutack-jaguar
Location: His dorm room
Partner: A guy from the periphery of our friendship group
How it went down: I was very drunk and it happened while we were watching Castle, so I stared into Nathan Fillion's eyes on the screen over his shoulder while he got off and I wondered if all sex was really this boring.
Spoiler alert - it isn't.
That's What Friends and Their Husbands Are For via smurfette
Age: 20 (a month-ish before my 21st birthday)
Location: My best friend's bedroom their house
Partner: My best friend and her husband
How it went down: Backstory - I'm a nerd, and was a bit of a chubster in high school, so I didn't date. After I graduated, I stopped talking to everyone but my best friend from school, got hired by the USDA after a successful apprenticeship, and went to community college. I had a bit of a breakdown from lack of social interaction, and over the course of a year dropped out of college, did a fair amount of drugs (mostly pot), lost 60 lbs, became a vegetarian, quit my science job and started working at the local co-op. I met my first boyfriend at our weekly Dungeons and Dragons session.
We'd been dating for all of two weeks, and had several awkward fumblings where he couldn't stay hard for the condom and would roll over to sulk, and I was getting fed up. He was a virgin too, but he wasn't the only frustrated party in the bed, and I was trying to be supportive but he was having no part of it. I was at the end of my rope, and called my friend to go hang out and bitch. I still lived at home, but she was married and lived with her husband and two kids, so I'd stay at their place frequently. When I got over there, I was greeted with a large bottle of Boone's farm and a bong hit just for me. I griped it out, got ripped, and we started talking about solving my problem. She (and her husband) had made it quite clear before that he was available if I was interested, and I'd engaged in kisses and fumbling with him but nothing more. (We had an unusual friendship, to say the least.) At this point, I was super frustrated, and the alcohol was changing my attitude on the matter from "Isn't this odd?" to "Why the fuck not?"
Her husband came home from work to find a plan hatched and two tipsy girls with devious grins. He was game, so we took the party to the bedroom. Even fortified with liquid courage, I was nervous, but I really really wanted to fuck. There was some kissing between the three of us while clothes came off. I remember sitting on his face kissing her while she rode him for a little bit (I didn't want to go first because I'm a dork). I was on my back when he entered me for the first time. He was big, but it didn't hurt because I'd been masturbating for years. Honestly, it was a bit underwhelming at first. It totally got better though, and we went through a few positions until I ended up on top of him. I didn't come, but I got pretty damned close.
The next day I broke up with my boyfriend. I didn't tell him what had happened the night before. I never slept with my friend or her husband again, and we drifted apart eventually. It was nearly a year before I had sex again. My second boyfriend was awesome, and we fucked like nerdy rabbits. I wouldn't change a thing, except maybe dumping the first boyfriend sooner. He was a tool.
Just A Little Sex with a (Frat) Brother via Michael
Location: His bed
Partner: Fraternity brother...
How it went down: I attended a small liberal arts college in the south, and I ended up pledging a fraternity my freshman year. He was the president of that fraternity and three years older than me. Once a year the chapter would have this long, drawn out ritual that ended with the incoming pledges being assigned a "big brother," an upperclassman in the fraternity who would take the younger pledge under his wing. After the ceremony it was tradition for the big brothers to take their "little brother" back to the fraternity house to drink and whatnot. At one point in the night, we ended up going to his room to get some ice, which somehow turned into a slightly drunken awkward kiss that transitioned into slightly drunken awkward man-on-man action.
/actual true story.
The Dominant Older Woman via SageGirl's husband
Location: Her bedroom. 3am.
Partner: Then, she was the receptionist/dispatcher at my work. Now she's my wife. I didn't discover this till later, but she's three years older than me.
How it went down: She joined the company about a year after I did, I was in and out of the office a lot, because my job was mobile, so I'd stop and chat with her whenever I went by. She was fucking gorgeous, huge tits and whip-smart and funny. Me, being at the time, a fat, bespectacled nerd with a serious self-confidence problem, immediately thought "She's too good for me" and masturbated furiously to her image from afar but never made any moves on her for months. But we talked, laughed and, when my job gave me long breaks, I would keep her company while she wrangled the phones.
Conversations soon led us to discover that we had the same career plans (we both wanted to be cops) and just when I had barely wrangled up the gusto to ask "maybe we should train together some time?", she beat me to the punch and said (OH SO CASUALLY) "You should come running with me sometime!" A chance to see this girl in spandex? hell yes.
The run was scheduled for friday night, at the university campus next to her house. I got lost. Like, really lost. We were supposed to meet at 9pm (we both got off work late) and I didn't get there till closer to 10:30. She was good-natured about it, and off we went, running around the track at the university. At this point, I really didn't notice that her eyes were pretty much boring a hole into the crotch of my running shorts. And I really didn't pick up on the three times, she got super close to me and asked me whether I'd had any girlfriends (no), or had anybody kissed me (no) or whether I had anyone I had a crush on at the office (her, but I wasn't going to admit that straight out, so no). To say I was an oblivious sap would be an understatement.
After the run, she brought be back to her place, which was really a basement room she was renting, and fed me pie (pumpkin, this was Thanksgiving weekend), and basically, (now that I have the benefit of hindsight), chatted me up for two hours straight, inching closer and closer to me as the minutes passed (she had started out on the opposite couch, but then by the time things came to a head, she was sitting at my feet with her head in my lap). It wasn't until this point that I realized what she was after, and to say I had no idea what to do would be an understatement. I remember staring awkwardly away, trying not to burn holes in her cleavage, making vague "I'm not sure about this..." excuses.
Thankfully, I was in the hands of somebody on a mission, who was not even going to let the vague discomforted of a horny, unsophisticated 20-year-old virgin stand in her way. I later found out that this mission was due to the fact that she and the other receptionists had been speculating on the size of my penis for months.
She pulled my face towards her and kissed me (FIRST KISS WOOOO), and all her clothes seemed to fall off shortly after (I started wondering if a film crew was hiding somewhere in the room, because this shit only happens in movies right?) and we were on her bed, and oh god, I was able to touch her everywhere. This is when I discovered, low and behold, I was good at touching. (or maybe it was all the lesbian porn I watched? Watch lesbian porn, everyone, they are good teachers). Either way, she initiated everything, from pulling my clothes off to climbing on top of me. I was too lost in a state of delighted misbelief to do anything useful. I seriously thought I was dreaming. Up until, mid-act, my brother calls - and me, making dumb virgin moves - actually picked up. Hot beautiful girl raises eyebrows.
Brother: "When are you coming home?"
Me: Later. (hangs up, throws phone across the room).
I drove home shortly after, wondering if she had slipped something into my pie.
And All Because of a Diva Cup via M Owen
Age: 19 years old
Location: Freshman Dorm
Partner: Boyfriend of 2 years
How it went down: For the longest time I couldn't figure out how to use a tampon so I went to the school nurse and had her show me how. Then I got overzealous and decided to start using a Diva cup. My boyfriend was hanging out with me while I was trying to work it in. I couldn't get it in and was frustrated and on the verge of tears when I decided to have him help me stretch out. It was completely unromantic but he was totally into it and then neither of us orgasmed because I didn't need us to orgasm in order to get the Diva cup in. Poor guy. Things got better later of course.
And Air Mattress Does Not a Bed Make via Insomniac
Location: Air. Mattress. AIR MATTRESS! I couldn't afford anything else and was already in a shitty apartment in a shitty neighborhood after being told I could not stay with my parents for a summer between college semesters. The room was incredibly tiny. It was also in a hot city in the South in the dead of summer, and we did not have air conditioning. 101 degrees that day. All of this will play into the saga.
How it went down: He was my boyfriend (I'm a girl), and also a virgin.
Having sex on an air bed is at best a calculated risk, and at worst a complete and utter shitshow. This was the latter. Both of us were virgins, and he got a little...overenthusiastic when I suggested that it was time for us to do the deed. Because of the previously mentioned heat, we were both gruesomely sweaty (this will come into play later). We struggled a little bit with the condom and subsequent insertion, as novices are wont to do, and he started going to town. Like, REALLY going to town. He must have thought that the more athletic the thrust and the wider its range of motion, the better the sex.
So the air bed was rockin and rollin, when suddenly he thought it was a good idea to try to put his hands under me during a particularly hearty thrust. We lost our balance a bit and shifted to the edge of the bed, which as any experienced air bed user will know, caused it to tip over completely, ejecting us from the bed. He rolled a foot or so and, it being a tiny room, actually SMACKED HIS ERECT PENIS against the wall. I heard his cries of anguish and stood to help him, but because his body had tracked sweat across the floor, I slipped, fell back on top of the air bed, and popped it completely.
It didn't hurt for me at all, and we went on to have a pretty fulfilling sexual experience together. At his place. On a real bed. Anyway, I love trotting out this story when sharing worst experiences with sex.
The Mystery of the Conch Shell Condom via Butchie
Age: I was 16, he was 17, and I felt like a goddamn badass.
Location: Rural Pennsyltucky, against the upstairs wall on his divorced mother's condo's hallway, and because she wasn't really a person, it was lined with white shag carpet, and why this matters will soon be clear
Partner: My sweet, sweet high school boyfriend of OVER A YEAR come onnnnnn
How it went down: I was an emerging poet who loved and dated a boy for over a year just because he was the lead singer in a band and (this is what's more important) wrote the lyrics to all their songs. His mom—a local public high school English teacher who wanted desperately to be a writer, and with whom I hoped to connect so sweetly with that we'd go see Charles Dickens' plays together at Christmas, both of us wrapped up in scarves she'd knitted, or else we'd take bus trips to New York City just to smell the public libraries—hated me. Luckily, she hated Pennsylvania more, but before leaving for a week-long vacation in the Florida Keys with her overweight Match.com police officer (someone she called "Bubba,") she left him with a box of conch shell, spiral-shaped condoms, which are just as strange as you might imagine, "because I know what you're going to do in my empty house."
(To this day, I've never been able to find these condoms in a store again, which means that obviously way back in 2004, his mother must've ordered them specially from an online porn shop, which is great fun to think about!)
Chris and I were, as you might well guess, completely disgusted and freaked out, but we were also seventeen, so after striping one another bare, we began to have sex the only way we knew how: the way they do it in porn, with my back pushed against a wall, my legs wrapped around his waist, and Chris thrusting anxiously into me with unparalleled awkwardness and noise. I began to bleed—just a little at first, and "Keep going," he said, "don't worry!"—but then the blood continued, and in retrospect, it really wasn't any more blood than I imagine any other girl lost, but at seventeen, on a white shag carpet, in the upstairs hallway of a total bitch, we both panicked. We stopped having sex to try and clean the carpet, but the wet paper towel only smeared it and made it worse, and then we decided, Well, fuck it then, and resumed our former position, except now Chris' hands were bloody and wet from all the failed cleaning and we smeared it all over the wall.
I came, which is perhaps what's most surprising here, but we spent the whole rest of the week repainting the hall, scrubbing the carpet with every kind of "sit and wait" foaming cleanser available from our small-town hardware store, and every time I was over, we'd return to the hallway to neurotically examine the spot from different angles and in different light.
We didn't date a whole lot longer—that kinda push the kibosh on sexiness—and his mother has since moved, but I can't help but think about that hallway whenever I visit home.
The mysterious conch shell condom, however, remains a mystery.
BONUS: While she did not follow our guidelines and while this story had been published on her Myspace before in 2006, it would be unfair not to call out our fan-favorite, via dollyrkr:
Snuck out of parents house a week before my 15th birthday. 1988. Walked to the party in the surfer-laden suburbs of Lake Forest (yep, the OC baby!). Was wearing thin peach top with black bra underneath, and short black 80s skirt that had those 3 ruffles tiered down it. Was blonde. Was very blonde due to Sun-In. Was tan. Was pretty fucking cute. Was being very brave because I hung out with punks, losers, dorks and retards but I really wanted to lose my virginity to a boy based solely on his looks, since I couldn't find one who was worth my time, and I was fucking horny living among all those pliable sun-bleached-brained boys.
Sauntered around surfer boy party looking for boy to fuck. Wanted sex unbelievably badly would possibly explode upon contact. Girls looked at me knowing that I'd come alone, I didn't like any of them, it wasn't my scene, and I was invading their boy cliques. Held beer in keg cup and eyed up every last one of them fearlessly, I respected none of them and I walked as if in a force field, eyes roving like the Terminator's.
There were 4 boys that all girls wanted. They were the shining stars of El Toro High School. They were known as the Grommets, like the fish that played in the ocean in the day and fucked on the beach at night. They were golden. The sun kissed their eyebrows that flickered with their confidence. More than any of them I wanted a boy named Andy. It stuns me, I must have just forgot his last name over the last year or two. Maybe I'll remember it. Something with an S. I wanted him so bad and he'd never known I existed. I didn't want to know him, I just wanted to fuck him. So I never approached him or talked to him at school. I just walked by and lusted. His best friend was Mark Gotro. Mark was hot, he was a grommet. The four of them were huddled together near the keg and I listened as I pumped more beer in my cup. Andy was explaining that his goal for the evening was Really Big Tits. That's all he wanted, all he cared about. He was a year older and had been fucking for what I imagined as ages. This killed me because I was a budding B-cup back then.
It also reduced my inhibitions of approaching them, knowing I had no chance. So I introduced myself and looked round at them, these fifteen and sixteen year old kings. We chatted and Paul, the least cute one of the four, but still quite fuckable, seemed rather interested. I remember mentioning I'd been in such a hurry slipping out of my house unnoticed I hadn't even worn underwear! My palm over my cherry holding lips.
Then a miracle occured. Kevin Gotro, uber-king of the surfers of Laguna Beach, Mark's older brother, all eighteen hunky years of him appeared. He tousled Mark's hair complaining that his little brother's party was all there was to do that night. His skin so tan it made freckles in his cheeks, where his cheekbones lit, he stood above us in all his six footed glory with his strong broad shoulders and his golden eyes danced as if he were a wise old man and we were all just a bunch of silly gullz and boyz drinking kool-aid. I didn't say anything to him. I just stared at him. I asked his brother which room was his. Mark grinned and loudly announced my query, exactly as I knew he would. Kevin grinned at me. I just stared. He said "you wanna see?"
We went upstairs. I had fantasized about this for half my life up till that point. I was going to be a tigress. I would say all sorts of brilliant and witty quips. But instead what flicked through my mind was an episode of the Wonder Years that had played last night. Where he'd stood with Winnie on a hill and they were finally, fucking Finally, going to tell each other they liked each other. They stood on the hill and he drew circles with his foot. It symbolized shyness, and deep feelings of adoration that could not be spoken. In the bedroom there was thin shitty carpeting and my foot tried to draw circles, I tried to be the sweet innocent girl with the older man, but my foot kept catching on the carpet and I must have looked really foolish. He stared at me grinning for a while. Then he went up to the bed, which was a bunk bed. He didn't use the bottom, the bottom was removed for space. The lights were out. We kissed up there in the top corner of his room. It was the very first time I'd ever french kissed. It was like swimming underwater in a simmering cave. I forgot about sex, I just wanted to kiss him. I never wanted to stop kissing. At that point in my life I masturbated probably two or three times a day at minimum. Somedays I just let myself have it all afternoon. Being a latchkey kid and all. So I really only thought I wanted sex, but then I dove into his mouth and never wanted to come out. Light came in through the window and I would open my eyes for just a moment to glimpse him, afraid he'd stop if he saw my eyes. But his remained closed, and I stole more and more glances, astounded that I was kissing such a handsome man.
Then Andy came in. With a girl. I didn't look down, but I knew, he'd found a girl with big tits. Kevin said nothing he just kept kissing me and I sure as hell wasn't going to stop him. We moved our tongues and felt each others bodies while we listened to Andy get her breasts. She was resisting, stupidly, trying to make the situation more than it was. As if she weren't making out at a kegger in a room with other people in it. He was being as insensitive as a sixteen year old charmed shit can be. She was as secure of herself as any fifteen year old would be: does he really just want me for my tits? Yes sweetie, he does. And It's Ohhhkayyy.
Finally she relented and in the silence we felt him grope her to his heart's content. Our tongues still rolling like the waves he surfed, this made Kevin huge and by then we were naked. I was more wet than I'd ever been before, so much so it blew my mind. In the streetlight I saw his form mount over me, and my engorged lips hung open mouthed at the sight. It was heaven that form in that lighting, above me, about to take me. The girl below me said, "Andy", and Kevin glanced down for a second, which meant he had to whip his hair back across his face to clear his eyes, which was music. My legs were too close, and he fumbled trying to get in, and then he pushed.
It was the most painful thing I'd ever felt. I felt I'd broken bones, I'd never walk again, I felt the heat of the body's reactions to pain well like a pool over my pelvis, with Andy below I tried to not to make a sound, I tried to whisper, Please, no, it hurts too much, take it out.
Andy's voice bolted up as he rose from his molesting, "Yeaaah! Kevin!! Dang!"
Kevin was not to be distracted. He tried to soothe me, petting my hair back from my forehead saying he just needed to be gentle and slow and then it would be good. He tried to pull him out slowly and even that felt like I was being torn at. I let him push in once more and it felt no better, which seemed the cruelest joke of the gods to be played on me of many well done ridicules. I begged him off, with him becoming invisible to me in my despair. He laid back and whined, "Well, can, you, at least, suck it?"
I'd never done that before, of course, and the results were hysterical. Since all I'd ever heard was "suck it" and "blow job" I actually thought you just sucked it like a lollipop. No up or down, just put your mouth around it and suck, come up for air, apparently, as it turned out to be necessary to do, and then - blow? So, I sucked like a vaccuum, squeezing it tighter and tighter until I had to release, and then blew on the tip. He let me go on like that for quite a while, which must have just baffled him to no end, finally pushing me off, saying nevermind, and we all fell to sleep.
At dawn, I heard him awake and I feigned sleep for a moment. He sat up slowly enough at first, and then after a moment's pause, bolted out of the bed and there was great commotion in his bathroom, and then I heard his famous Orange VW bus peel away from his own house. Hurt, but
not surprised given the events of the prior evening, I sat up. There was blood literally as though I had been murdered all over the sheets, my legs, the blanket, Everything. It was like Carrie. I couldn't understand how that much blood could have come from me. Later I would learn that it wasn't just Kevin who got me so wet, I had indeed simulteanously started my period that night. I groped to the bathroom, stunned that I was dripping blood the whole way there, and tried to wipe myself as best I could.
I snuck back in the house through the doggie door, couldn't shower at that wee hour without Mom knowing I'd been out, so I slept for a few hours longer in my mess. In the full Sunday morning, after my shower, I went to Mom for Tampax.
"Oh! My little girl has become a woman!" She cried.
Image by none other than the incomparable Jim Cooke.