Sex Diary: One Week, Two Disappointing Rolls In The Hay

Welcome to the Frisky “Sex Diary,” in which an anonymous person shares the details of her sex life over the course of a few days. Sometimes these entries are filled with revealing romps, while other times there is nary a naked moment in sight. Some of these diarists are frequent contributors. Want to share a page from your sex diary? Email [email protected] All entries will be anonymous.Diarist: A single 20-something living in Brooklyn, who broke up with her boyfriend a few months ago.


9 pm: Meet up with co-worker and her boyfriend for a free show at Brooklyn Bowl, where I proceed to down three vodka sodas in quick succession. Send intentionally cryptic text to Brick, a guy I’ve hooked up with in the past and with whom I’ve recently reignited a playful GChat relationship. Pay little attention to the band and instead sit and chat with the couple, who are throwing a holiday party at their house on Friday. Ask if there’ll be any hot single men at the party. I ain’t too proud to beg. They claim that most of their friends are gay, but my friend’s boyfriend mentions a former work buddy who just moved here from L.A. and might be worthy. He says he’ll invite him for me.

10:30 pm: No response from Brick. Indignant.

12am: Meander home drunkenly, making a pit-stop to procure appropriately greasy late-night drunk food. Get home to see that Brick has sent me a GChat message in my absence. Dammit, if he’d gotten back to me a little earlier we’d be doing it by now, but having just consumed my weight in stir-fried noodles, I’m feeling distinctly unsexy. Our GChat convo quickly devolves into e-sex territory. He tries to get me to call him and talk dirty while he beats off, but I’m not in the mood. I tell him I’ll be in his neighborhood on Friday, so he should save it up til then.


3 pm: Peruse an ex-boyfriend’s Facebook page out of curiosity. We broke up two years ago, and I have no lingering feelings for him – I was the one who ended things, and definitely feel he was more into me than I was into him. Up until about six months ago, he was in fairly consistent contact with me, sending emails and attempting to make plans with me, but when he invited me to a Fourth of July party, I alluded to the fact that I was dating someone, and he’s stopped reaching out since then. Notice that someone has commented on his page, congratulating him on his new apartment with “Brooke.” Apparently, in the six months since he’s stopped badgering me, he’s met someone he’s gotten serious enough with to cohabitate. Makes me wonder if he was just desperate to settle down.


10 pm: Co-worker’s house party and I’m loaded for bear, as the saying goes. I hover over the cocktail table downing cava and strike up a conversation with a cute mustachioed dude whom I’ll call Shane. We get on like a house on fire, and though he’s not my usual type – I like uber-preppy frat boy flunkies or burly lumberjack types and he’s your textbook underfed hipster – I feel a spark. Turns out he just moved to town and lives in my neighborhood. He ducks out early to meet his sister, who’s visiting from out of town, but not before friending me on Facebook with his iPhone – I guess that’s the new asking someone for her number — and insinuating that we should go out and party in the hood sometime. After I leave, the host asks me how I liked his friend, and it’s only then that I realize he’s actually the single guy they invited on my behalf, unbeknownst to either of us.

11 pm: Text Brick something innocuous to get the ball rolling. Make plans to meet him at a bar near his house.

1 am: Arrive at bar to find Brick sitting alone, wasted and half-asleep. Really dude? After a month of laying the groundwork for a hook-up, I expect him to bring his A-game. So frustrated that I consider leaving, but don’t. We stumble back to his place, where I tell him to go down on me in the vestibule of his apartment. He does, sloppily. We get inside and proceed to have fumbling, largely unsatisfying sex. He puts it in my ass without any lube, which makes me furious – what’s he thinking? – then tries to put it back in my ‘gine. Uh, hello? Rule #1 of butt sex: lube. Rule #2 of butt sex: do NOT try putting it back in the vagina after it’s been in the ass. I tell him to go wash off his junk, which he does. By the time he gets back, we’ve both lost that loving feeling. I roll over and go to sleep.


7 am: Wake up next to Brick and have sleepy morning sex. In the middle, I feel myself getting emotional about my most recent ex. Stupid feelings ruin everything. He comes, I don’t. Fall back asleep.

9 am: Brick has failed to mention that a team of construction workers is replacing his bedroom windows today, but it becomes evident when loud hammering and shouting startles us awake. Guess that means I’ll have to sleep off this hangover at my house. We get dressed and he walks me to the subway station. We part with a quick cheek-kiss, neither of us feigning delusions about calling each other to hang out again. I chalk it up to a “palette cleanser” – otherwise known as rebound d**k. He’s the first person I’ve screwed since breaking up with my ex two months ago. Had to happen sometime, and at least since he’s a repeat I’m not adding to my number.

3 pm: Too hung over to function. And my butt hurts.


4 pm: Got a Facebook message from Shane, the cute dude I met on Friday, commenting on the “hot dip” I brought to the party. Euphemism? Exchange a couple vaguely flirty one-liners but make no plans to hang out. Consider asking him out if he doesn’t make a move in the next couple days.

7 pm: Email old high school friend with whom I’ve had some sexual/romantic tension for the entirety of our ten-year relationship. We’ve never hooked up, but I can tell he wants to. My attraction to him is mostly dictated by how horny/drunk I am. Tell him it’s been too long and we need to hang out soon.

8 pm: Holiday party at a friend of a friend’s – no eligible bachelors on the premises. The hostess’s quasi-boyfriend is the textbook definition of boor – a big, dumb, rude oaf who’s 33 and lives with his mother. Classic case of the uniquely New York-ian phenomenon of the awesome girl dating a guy considerably below her worth. Why do we put up with such f**kery? Am subjected to a disgustingly juvenile series of jokes regarding incest and morning wood before I decide I’m too old for this and leave.


11 am: Wake up from a dream in which I discovered that my good friend was secretly dating my most recent ex. Feel weirdly upset and haunted all day, and unfairly pissed off at my friend.

9 pm: A friend brings me along to a concert as her wingman, as she’s planning to meet up with a dude she wants to get it on with. He never shows. I try to comfort her, but I know she’s disappointed and frustrated. As we stand near the bar swaying to the music, Ed Westwick, aka Chuck Bass, sweeps in with his real-life girlfriend and I try not to stare. I go to the bathroom and he’s standing in the corridor outside. As I pull down my pants to pee, I am thrilled at the thought that he’s just outside the door, mere feet from my naked body. Consider complimenting him on his turn as the vampire-obsessed queer on “Californication” this season but decide against it. I don’t wanna be that girl.


4 pm: Engage in a discussion of golden showers with a married guy I’ve had a long-standing, inappropriate e-relationship with for years. But I know better than to let it go beyond the realm of the theoretical. No use getting all hot and bothered when I know it won’t lead anywhere. He mentions he’ll be at a holiday party tomorrow and says I should stop by and find him for a “hug and an ass-grab.” Uh, OK.

Plan to go to office party with former co-workers but my friend with the invite bails, so I resort to a bowl of pasta and “Sex Rehab with Dr. Drew.” God, that Kari Ann is a bitch.

9 pm: Check Shane’s FB page and notice that he’s changed his profile pic approximately five times since last time I looked. Narcissistic much? Officially no longer titillated and decide then and there I’m not gonna ask him out. Get a life, dude.


7 pm: Meet up with group of girlfriends for drinks and pop in to a media networking party that’s really just an open bar with a crappy DJ. Duck out after several drinks and meet up with another friend to see a band at a club nearby. She’s brought a dude she thinks I might be interested in. I met him some months back when he was visiting from England and he’s now moved here permanently. Hmm, he’s not as cute as I remember, but that accent makes up for a lot. Since he took my spot as my friend’s plus one, he offers to buy me a drink. We belly up to the bar and proceed to flirt for the next two hours. My friend leaves and we wander over to the holiday party that Married Dude mentioned he’d be attending. The Brit kisses me outside, and although nothing’s ever explicitly said, we somehow both arrive at the conclusion that he’ll be coming home with me. Inside, we do a quick lap. Married Dude is nowhere to be found, but I do run into a guy I had amazing sex with a few years ago and we make surprisingly not-awkward chit-chat. I chuckle to myself as I introduce former one-night-stand to future one-night stand. The Brit and I have a drink and then hop a cab to my place. I joke drunkenly that now that we’ve kissed he’s officially my boyfriend. He plays along.

11 pm: Back at my crib, we get down to business, but either he’s nervous or has had too much to drink, because he’s having trouble keeping it up. GAH. What the hell? I thought the older I got, the BETTER the sex was supposed to be. He fumbles with the condom. Finally he gets it up but after two pumps he pulls out and comes. F**KING AMATEUR. Frustrated and too drunk to bother being polite, I suggest he leave, telling him this isn’t really working for me. He insists I give him another shot (pun intended) and tells me he likes me. We leave and get a drink across the street, then come back to mine and tumble into bed. We have much more successful sex as quietly as possible – both of my roommates are home and sleeping. My bed squeaks something fierce, so he bends me over the bed and goes to town. His balls are HUGE, and they’re hitting the right spot. I whisper to him that I’m glad he talked me in to letting him stay. Afterward, we roll over to go to sleep.

4:30 am: Wake up to the Brit snoring loudly next to me. Feel a monstrous hangover coming on and hope I can get rid of him first thing in the morning without the requisite post-coital pillow talk and cuddling. In the cruel light of day I discover how unattractive I think he is.


9:30 am: The Brit is wide awake and quite possibly the single most annoying human on the face of the planet. As I burrow into my pillow and try to ignore him, he begins lecturing me on nutrition and telling me that he comes from a family of farters. Then he playfully humps my leg and asks to “do it” again. I tell him if he touches me I’ll throw up on him and that he can either shut up or leave. He cuddles up to me and falls back asleep for an hour, then thankfully gets up to leave, asking me for my number before heading out. I contemplate giving him a fake, but realize I’ll probably be forced to see him again in social situations since we have mutual friends. Good thing: he immediately calls me to make sure I have his number. Ugh. As soon as he leaves I strip my bed, cursing my slutty alcoholic ass and swearing to myself that after two hugely disappointing rolls in the hay this week, I need to start setting the bar a little higher. A girl needs to get laid, but this is ridiculous.

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