Sex Diary: You Play the Game, You Get Bruised

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: Single 21-year-old, six months into a 10-month study abroad program.

Dec. 18: Last day of term in London; I fly back to Boston. I could have gone to New York, since it’s closer to my parents’ house, but I have ulterior motives: the guy picking me up from the airport. J’s a workaholic grad student and he’s doing ridiculously squiggly math problems when I show up at the gate. Our hands are all over each other on the interminable subway ride back to his place. After being best friends for two years and a two-year falling out over high school drama, six months ago we admitted to having feelings for each other. Now we’re finally both single for the first time ever.

After dinner with my best friend (gotta show off J), we go back to his place and don’t waste any time. The sex is fast, aggressive, and incredibly hot. Afterward, we’re both exhausted, but we can’t stop making out and touching each other. He tells me that when I get back from England in the summer, he wants to finally give our relationship a shot. I can’t stop smiling.

Dec. 19: In the morning I wake up and see him across the room at his desk grading exams. I pull on his shirt, make coffee, and come up behind him to kiss his neck. I like that I know that he likes that now.

On the train ride to my parents’ house, I worry that the stakes of this are unequal. I’ve had feelings for him basically since we met; he hasn’t always felt the same, but now that he does, it’s huge, because he’s so anti-commitment-phobic that he’s paradoxically afraid to take chances that might not work out. I, on the other hand, am a big fan of improvising. And I’m playing the field, at least until summer. But my feelings for him have never gone away completely, and now that we’re so close to having something, being away from him for another six months is going to hurt like hell.

Dec. 22: J comes for a visit. We go to dinner and hang out with old friends – some of them know about us; with others, we’re trying to keep it on the downlow to avoid pissing off his crazy ex, who’s still peripherally a part of our social circle. But they all see us show up together and leave together; one buddy casually mentions that J’s crashing at my house. Way to be subtle, guys.

No sex, though – J’s got a sports injury that keeps him on the bench this time. Frustrated. I also learn he’s never gone down on a girl. So I have to teach him how to give oral sex now? Damn it. I might not bother, since it’s never gotten me off. Still, given that he’s nearly 23, his lack of experience is a little unnerving.

Dec. 25: Last communication (via Facebook chat … lame) with M, the guy I’ve been semi-dating for the last three months in London. He’s stereotypically British in his reserve; he also randomly jets off around the world without notice, so he’s totally unreliable. I think we both know it’s fizzled out. But it was fun while it lasted … he earned the nickname “Marathon M” for a reason.

Dec. 26: I get into a fling with an old friend’s husband’s buddy. C has a wrestler’s body and is fantastic in bed. He’s also the most gentlemanly guy I’ve ever met, and it’s nice to be treated right after M’s inconsistency. I feel guilty as hell, though – because things just started getting off the ground with J, I’m only home for three weeks, C just had a bad breakup and seems to be falling for me at record speed … and I feel like I’m falling for him too. This is ridiculous. I just met him! He’s rebounding! I’m in love with J! But I can’t deny that we click and I feel fantastic when I’m with him. He’s also the first guy to get me off in five months, so that might have something to do with it.

I tell C about J, but I don’t tell J about C. Maybe a little dishonest, but we’ve talked about it — there’s no expectation of exclusivity yet. My brother gives me an affectionate and well-deserved ribbing about being a “playette.” But hey, I’ve been Serious Relationship Girl since high school — I deserve to have some fun, right?

Dec. 31/Jan. 1: Mindblowing sex with C on New Year’s Eve … and in the morning. Apparently I’ve just popped his drunk sex cherry. After he leaves I find a text from J wishing me a happy New Year. I feel like a crappy person. Later, C and I drive around the countryside talking about our lives. If I didn’t want to pull over and jump him right there, I’d say he’s my new best friend. But people don’t sleep with their best friends.

…Oh, wait. When I get home, I guiltily call J. He tells me he has to cancel his next visit because of a last minute work trip to New York. Oh. Great then. See you in six months. I’m pissed.

Jan. 5: C stays over the night before I leave my parents’ to go back to Boston to see friends for a few days. As he drives off in the morning, I stand on my porch staring at his tail lights, wishing irrationally that he wasn’t leaving. He stops and drives back; I run down the driveway in slippers, in the snow, and jump in his truck for an amazing goodbye kiss. Neither of us says a word, and then he leaves for good. This kind of thing belongs in the movies.

Jan. 10: I’m back in London. I call M hoping for a last hookup (sex with him is like crack), but he doesn’t return. Oh well. I find out later that he’s randomly jetted off … again. I’m tired of the flakiness. Meanwhile, C keeps calling and texting and IMing me constantly. At first it’s sweet, and we have a hot sexting session one night. (Am I too old for sexting?)

Then it becomes annoying. Do you not understand the concept of a fling, guy? I tell him to back off because he knows I can’t follow through on a relationship with him. Then I feel bad. Did I string him along? Should he have known better? Should I have known better? I get very little contact with J over the next few weeks. I wish he could understand that I need the occasional check-in just to make sure he hasn’t wildly changed his mind, because I’m paranoid like that, but he’s not good at declarations of affection. Presumably, if he changed his mind, he’d tell me.

Jan. 25: I drunk-text J that I miss him and I hope he won’t tease me for drunk texting him. Why do I do these things? He’s not good with anything that can be described as sentimental, and always turns everything into a joke. His response: “Hey, miss you too. And I reserve the right to ridicule drunk texting whenever I see fit.” Does that count as teasing? From him, it’s usually affectionate. We have a weirdly adversarial relationship. No one really gets it. Including me.

Jan. 29: It’s been nearly a month since I got laid and it’s starting to get to me. I’m not good at dry spells. I go out for drinks with my housemates, including the one that’s been flirting with me for a week, B. Come the end of the night, it turns out everyone else has left, and it’s just us; we hadn’t noticed because we were engrossed in conversation. He’s funny and charming and a little sheepish; I feel slightly idol-worshiped for my experience in the film industry, as he’s a “huge film nerd”. When we get back to the house, I can tell he’s trying to decide if he should ask me back to his room. Instead, there’s a hot but fumbling makeout in the stairwell and we both go to bed.

Jan. 31: B and I have dinner with our housemates, then find excuses to hang out afterward — washing up, tea, and a walk to the market because we’ve run out of wine. We forget the market and, in a city square, under a willow tree, he kisses me again. It’s better sober.

Feb. 2: After drinking with friends into the wee hours, B insists that I go back to his room. I tell him that’s too forward for me, but he says he just wants to cuddle and sleep. It’s nice — I’ve been missing human contact. In the morning he goes to class, but insists I sleep in until he gets back, and then he makes me breakfast. Damn, he’s good. I’m wary of his smoothness, but still totally swooning on the inside.

That night, he ditches a squash match to hang out with me and my friends. Wine flows freely here, and he gets drunker than I could tell and tries to literally carry me back to his room. I can’t decide whether to be amused or offended … going with amused for the sake of household harmony. We’re already breaking the golden rule; no need to make it worse by making a scene. I chat online with J about sports; he makes me a bet that I won’t be able to distract him from hockey playoffs with sex. I’m more than willing to take that challenge.

Feb. 7: I’ve barely seen B all week, and I’m starting to get flaky vibes. We’re both field-players, we established that early on, but I think he’s less considerate about it than I expected. I’m also suspicious that he’s still hooking up with his ex. But he helps me make dinner and gives me little flirty touches. Screw flirty touches. We haven’t even had sex yet. I want to get laid, damn it. When I only get to talk to J occasionally, I’m craving skin-on-skin all the more.

Feb. 12: B and I go out for a lecture by a pundit we both admire. He’s sweet and charming — he’s either actually into me or really good at his game. I think tonight will be the night, but when we get back to the house he cuts the date weirdly short and heads back to his room. Offended, I go out for a walk with a friend and rant a bit.

J and I talk for a little while, and I mention what happened — he’s not the jealous type — but he misunderstands and thinks that, in my dating life here, I’m playing for keeps. I try to soothe his ego, without outright admitting that he’s the only one I really want. Ugh, this long distance thing sucks hard. Especially with someone who’s emotionally squeamish. But the fact that he got upset at all was unusual for him — and it’s proof he still has feelings for me. Twisted? Yes. I’m trying not to care about that part.

Feb. 13: B and I had originally had plans for the 14th — not intentionally; it just happened to be a good day to see a film we were both interested in — but he says that if we see it tomorrow, we’ll have to miss our weekly Sunday dinner with our housemates. Trying to be easygoing, I agree that we can do it later in the week. Then one of our housemates mentions that Sunday dinner has been canceled anyway because B will be out.

I ask him what’s up — he’s clearly caught in a lie — and he says that he’s just “a bit of a flaker.” What the hell? He’s been totally disrespectful and I vow to end it. But somehow I still hold out hope that he’ll turn back into Sweet B. I give guys too many chances. I tell C about this, and C says he’s sorry I got jerked around — “And I still miss you and think about you every day.” I’m in enough of an emotionally vulnerable place to find this sweet and not weird.

Feb. 14: Spend the day shopping, getting drunk, and watching sci-fi with girlfriends. Avoiding rom-coms like the plague. I read nonfiction in the evening to keep my mind off men. I text J but he never responds. C wishes me a happy Valentine’s, but he mentions he has a new girlfriend now. That was fast. I find out later that B spent the holiday with his ex, who he swore he wasn’t still sleeping with. Figures. And to think I almost thought I was overreacting to his flakiness. I feel like a squash ball he’s been whacking against the wall.

Feb. 15: B hovers around me all day until I go out. Around dinnertime, I come home and go into the bathroom … and hear him in the separate shower next door. He pops his head out, thinking I’m his roommate, and I hear a girl giggling in there with him. Seriously? He’s f**king some other girl in our shower? A few hours later I run into him on the street, and he’s had a haircut. Which our housemate gave him. In the shower. I’m an idiot. He invites me to dinner tomorrow night, but I’m not free; anyway, I think I need to cut this situation off now before I humiliate myself any further. I wait around for J to come online, but he never does. Part of me still thinks it would be okay to hook up with B, just for the sex. The rational part of me says that’s stupid, and go get your vibrator you silly woman.

So I may be good at playing the field — at least at attracting other players to my field– but I don’t actually like it. I don’t like how it makes guys like C feel, and I don’t like how paranoid I got when I was on the other side of it. I want a boyfriend. I want J. I’m tired of the game — can we skip to the home run?

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