Love & Sex

Five Stories: People I Never Intended To Sleep With

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Tales of ugly ducklings who somehow talked their way into our sex lakes. 

Santa Claus

When he realized we were the same Chinese zodiac animal, one cycle apart, he groaned, "Oh, fuck." His consternation was funny, like his British accent was funny, like our mutual insistence that the fact that we'd met via our blogs meant one or both of us was an internet serial killer.

He had a dozen years, a dozen inches, and a hundred pounds on me, and with his glasses and prematurely pewter hair he exactly resembled Santa Claus. Stories of his ex-wife, told with the full force of fresh grief, only convinced me that he was closeted. We fell into one of those obsessive, shame-free, no-holds barred girl-and-gay-best-friendships. We shopped together, drank together, went to every festival ever, rented each other for weddings, whined about relationships and religion and family and work, and drew up itineraries for fantasy trips to Iceland and Japan.

I never wondered what he looked like under his paramedic gear. One big fat old guy, surely, was like every other big fat old guy. And Santa never did it with Mrs. Claus, did he? He seemed not just asexual to me, but anti-sexual, a twinkly eunuch who would only acknowledge his genitalia to soap it vigorously in the shower.

A twinkly eunuch who would only acknowledge his genitalia to soap it vigorously in the shower.

We got soaked on a weekend trip (to Comic-Con, of all places) and sprinted back to the hotel, collapsing into a massive sulk with cold pants and soggy socks. It was only natural to get off our wet things and wrap up in one of the fluffy hotel duvets. Finally the same height, I stared into his eyes — bright hazel, with a ring of sinister green — and the next thing I knew I was saying, around his tongue, in reference to my bra, "That comes off, you know."

On the drive home, we couldn't stop laughing about it — not at how funny it had been, more at how fun it had been. And how we'd never do it again, it had only seemed like a good idea at the time, we were cold, it was… our voices trailed off. When he dropped me off we kissed goodbye, ferociously, till we ran out of air, and it was like every Disney cliche in my life came true, about loving the inside instead of the outside, about beauty coming from within, about beauty not even mattering, just our connection.

And no, it didn't turn out to be a one-time thing. Which is totally awesome. — Premee

The Greeting Card

She was always just kind of "there," a friend of friends, hanging around with the crew. Nice enough, but meek and not initially captivating. Adequately cute in a tomboy pixie, "always the bridesmaid, never the bride" kind of way. She had a thing for me; I did not have one for her. With our friends, we partook in the usual slate of post-college pre-job activities: potluck dinners, cheap red wine, marijuana cigarettes, and the mining of Bob Marley box set for the choicenugs. Over several months, we went from hanging out in big groups of friends to hanging out alone together. 

I started to really enjoy her company, but on those evenings, it never escalated to anything more intimate than a shared joint. We were comfortable around each other (and often stoned), which allowed her to be a little more open. We had some engaging conversations about past relationships, future plans, and the dismal state of pop music. (Savage Garden and *NSYNC were charting at the time.) Perhaps I should have seen it coming, but honestly thought we were on the same platonic page.

I arrived at her apartment one evening and was promptly handed a card. It wasn’t a typical card-giving occasion, but i was mischievously instructed to open it. The front of the card featured cartoons with cute captions referring to new best buds, and the inside was completely blank save for one handwritten line, “I want to fuck you. Now." I had just been propositioned via a sex card.

I had just been propositioned via a sex card.

As I stared into the card for a moment, images of red flags waving frantically over silver platters collided in my head, only to be vanquished by two little hands pulling me in for her much-anticipated first kiss. We stood in the doorway making out like the plane was going down, until I was escorted into her darkened bedroom nearby. Shedding clothes, inhibitions and a hint of dignity, I threw her onto the bed and proceeded to kiss and lick my way down in between her legs, where I set up camp and went to town.

This process is usually a smash hit; number one with a bullet. Except on this particular occasion I wasn’t receiving any of the usual signals: no moaning, no, "Oh God," no arched back. Absolutely zilch. If we'd been drinking, I would have assumed she'd passed out. Thinking perhaps oral wasn’t her thing, I moved up and began fucking her in standard missionary. I may as well have been fucking a bag of rice. Zero response; no sounds, no words, no movement.

I quickly finished up and to my astonishment she whispered, "That was incredible," into my ear. I was totally baffled. How had this friendship gone so horribly awry? How had I just had the worst sex possible? I was under the impression that presenting a proposition in such a manner would have included bringing something, anything, to the table, even if it was just the cracker packets that rest beside the soup. I was wrong. — Scott

The Mixtape

The year was 1995 and I was in art school. Jonah was the ex-best friend and roommate of my ex-boyfriend. He taught me to play chess in the lobby of our dormitory and watched The Simpsons with me while Adam was cheating on me with various girls who did not skateboard or listen to Pavement.  

Jonah was punk as fuck but also had an emo-boy sensitive side. One night, the last night of sophomore year, he came to my dorm room with a bottle of Jackand a mixtape titled “Making lemons out of lemonade." This was before a mixtape was just a tattoo hipsters wear on their forearm; this was a carefully thought-out message. He was declaring his love; I was totally clueless. 

That night, we just had some drinks. I told him I liked Texas is the Reason and asked him make me more mixes. He did.   

Eventually, I caught on to the fact that Adam, my boyfriend, was a perpetual asshole and we broke up. The next fall, I ran into Jonah at a strangely serious screening of a Russ Meyer film and whispered it was my birthday. He pulled a bottle of Jack from his messenger bag and we killed it during the film. I dropped the empty and we laughed as it rolled, loudly, down the aisle of the auditorium.

I had turned twenty-two, but I didn’t have an ID because I didn’t drive and never went to bars. So after the film, he took me to a townie bar and pulled me through the men's-room window. I did my first shot of wild turkey. We played The Cure on the jukebox, and he was the first boy to tell me I was beautiful. We stumbled to his apartment and hid from his girlfriend, who lived next door to him. We opened beers, and he told me he had been in love with me from the minute he saw me in a Husker Du T-shirt on move-in day.  

This was before a mixtape was just a tattoo hipsters wear on their forearm; this was a carefully thought-out message.

I kissed him. He said, "Wait," and ran to turn on music, Jawbreaker’s “I Want You” on repeat. It was the first song on the mixtape he'd made me the year before.  

He was a sculptor and knew how to use his hands. We made love all night, and he talked about all of the things we could do together. In the morning, I snuck out while he was sleeping, finding cast-off clothes and leaving socks behind.

He never really forgave me for running away — I was banned from the house shows he threw for the next two years. I’m still sad, mostly because I lost a friend. — Kelly

Baby Mama

I saw Mark for the first time on my living-room couch, where he was buying weed from my roommate. I thought he was cute. Once he started hanging out more, I learned that he was also ten-years older than me, had a couple of kids with his ex-girlfriend, and was dating someone else anyway. (They didn’t get along very well, but according to my weed-selling roommate they, “fucked like crazy.”) I had a boyfriend myself at the time who I was planning to break up with — but because I wanted freedom, not a different boyfriend. Definitely not an older boyfriend who was sure to bring baby-mama-drama into my life.  Still, I couldn’t help flirting with him every time he came around, and was ridiculously pleased with myself when he quoted from a Stephen King book and I recognized it.

After weeks of flirting, we had one brief make-out session at the bar. At that point, I conceded that I wanted to fuck him but still refused to entertain the fact that he might someday be my boyfriend. This changed on one particularly hot May night.

We were going to the bar with our friends. While I watched from the car, Mark jumped up on the porch railing and tried to walk down it. He lost his footing and fell six feet to the sidewalk, landing in a hideous tangle of lanky arms and legs.

“You all right?” I practically screamed as he got up and came to the car. 

“Yeah, but my thumb hurts like hell."

Suddenly, I realized that I would get hit by a truck for the man passing out on the ground.

We collected his surly girlfriend outside, went into the bar, and sat in a booth. It was close to ninety degrees inside. Mark suddenly slumped over in his seat, pouring sweat, whiter then I’ve ever seen a living person.

“Feels like a bad trip,” he muttered as he slid to the floor. My roommate, helpfully, leaned over and shouted, “Dude, don’t be a bitch!  You just need a beer!” Suddenly, I realized that I would get hit by a truck for the man passing out on the ground.

“Get out of the way!” I screamed, diving to the ground to rescue him. My boyfriend appeared around the corner, holding up a plate (“I got fries!”), but the smile dropped off his face as I shouted that I had to go to the hospital. 

Mark’s girlfriend helped me carry him to the car and I drove him to the hospital since she didn’t have her license. When he came out of the E.R. hours later, loopy on Vicodin with his shattered thumb in a cast, he looked at me and said in wonder, “You drove me to the hospital."

I took care of him for the next couple of days, undressing him for bed and making doctor’s appointments. We were sitting out on my roof holding hands when he told me he loved me.  When I said, “I love you too,” I felt all my old promises and plans sliding away.

We’re still together, and though there has been plenty of baby-mama-drama, sometimes his little girl cuddles up next to me during a Disney movie too. It's all okay. — Ava

The Night John Kerry Lost

I was eighteen and newly impassioned about politics when I decided to volunteer for the Kerry campaign against George W. Bush. It was a bit of a disappointment. The shabby campaign headquarters in my small Southern town was staffed solely by two well-meaning stoners in their early thirties with strong political ideas but seemingly little ambition. Evenings after community-college classes, I would stop by the HQ and find the two in the basement sharing a joint while a DVD of Fahrenheit 9/11 occupied the few stragglers in the office.

On the evening of the election, the campaign "party" included myself, a friend, the guys, and three eighty-year-old veterans huddled around a small screen. As the votes rolled in and our hopes of victory began to look grim, we all decided to share a bottle of Jagermeister. The drunker I got, the cuter Sam — the older, more burnt-out of the two directors — became.

It is amazing how hard liquor can all but erase a woman's resistance to male-pattern baldness, extreme body hair and the overwhelming scent of patchouli.

It is amazing how hard liquor can all but erase a woman's resistance to male-pattern baldness, extreme body hair, and the overwhelming scent of patchouli. All I could see was his deep Mediterranean tan and surprisingly (after all the smoking) white, straight smile. Somehow (don't ask me how!) we ended up in the musty basement floor on what appeared to be a very old gymnastics mat. And surprisingly, the sex was good. 

I never saw him after that, but he called me once later that month — in the middle of Thanksgiving dinner, actually — and we chatted awkwardly. As strange as it all was, I've never enjoyed another election quite as much. — Meredith