The Pseudo-Fameball Oversharer in a “Secret” Relationship
DAY ONE
12:30 a.m.: After a tremendously dull networking event, I head over to my favorite NoLita imbibery, Sweet and Vicious. I Twitter my intentions, with the hope that a certain someone sees it and meets me there.
1:00 a.m.: The person I wanted to see my Twitter obviously didn’t, but two of my barely legal followers did. One of them is kind of chunky, but her friend is tolerably cute. The chunky one has lapped me on margaritas twice now, but I keep my eye on the prize.
1:45 a.m.: After ably convincing the chunky one she’s too drunk and needs to go home, I whisk the cute one into a cab and down to my apartment overlooking Ground Zero.
2 a.m.: I momentarily panic, having completely forgotten her name.
2:15 a.m.: Still can’t remember, but at this point it probably doesn’t matter. She’s pretty wasted, and the slobbery blowjob reinforces this fact. I can’t tell if she gives bad head because she’s 22, or because she’s blacked out.
2:45 a.m.: Realizing this girl will never be able to get me off with her mouth, I whip out a condom from my blazer pocket. I’m promptly shut down, and thereby resort to jerking myself off into her mouth.
3:00 a.m.: Tell her I have an early VC meeting and she needs to leave. Give her $20 for a cab ride home.
3:10 a.m.: Twitter something clever about blowjobs to make that certain someone from earlier jealous. See, we’re not really in a relationship. Or rather, we don’t let people know we’re in a relationship, since we’re both pretty high profile online personas. I have over 1,600 followers on Twitter, and she writes for a very well known liberal internet newspaper. The blogosphere would go crazy if they knew about us.
3:15 a.m.: Nicole. The 22 year old was named Nicole, I think.
12:15 p.m.: Wake up and Twitter something cute @Nicole, just to further confuse her when I don’t answer her texts for the rest of the week. Back to sleep.
10:00 p.m.: Thinking about masturbating, but wind up falling asleep before I can even get my laptop out. I feel old for being too tired to jerk off.
DAY TWO
3:20 p.m.: Plan on getting dinner later with the secret lady, and I rub one out to clear the pipes for later. Twitter something about how excited I am, both literally and figuratively.
5:00 p.m.: Dinner is uneventful, she goes on and on about how her boss is so demanding. I inevitably wind up fantasizing about her boss, who is a rich, powerful Grecian blogger, and could totally support my goal of never having a real job again.
7:00 p.m.: Back to her apartment, where things get hot and heavy early. Unlike last night’s encounter, this woman is a fair bit older, but her experience shows and I enjoy every second. I don’t normally like sober sex (or have it at all, for that matter), but with her, it’s incredible. She just knows what she’s doing, and I don’t get that with the girls I typically sleep with.
9:30 p.m.: She wants to go for second round and I happily oblige. My only complaint is her proclivity for being on top…she’s a bit of a feminist, and it shows in the bedroom. I don’t think she’s ever blown me, come to think of it.
11:00 p.m.: I’m spent, but before passing out I Twitter an anti-semetic feminist joke, just to piss her off a bit. She playfully smacks me for my smarmy comment and I fall asleep next to her.
DAY THREE
9:00 a.m.: ARGH! I hate waking up before noon, and even her offer of morning sex can’t rouse me. She leaves for work pissed at me, and of course now I can’t get back to sleep. Today is going to suck, and I Twitter that.
6:30 p.m.: Feeling better after napping all afternoon, I head over to a Tumblr Meet Up. Tumblr Meet Ups are surprisingly awesome, since the guy/girl ratio is far better than any other tech party (besides the iVillage parties, but I’m not allowed at those anymore).
7:00 p.m.: The regulars are here, plus a new circle of cute girls. I swear to god, these Tumblrettes are duplicating.
9:10 p.m.: Already drunk, and playing spin the bottle with 6 twenty-something girls. I feel like I’m back at UND, except I never really did this stuff back then. I Twitter about how cool Tumblr is.
10:45 p.m.: Besides a few makeout sessions during spin the bottle, I don’t think anyone is coming home with me tonight. I ignore a text from my pseudo-girlfriend; need to keep on the offensive a bit.
11:30 p.m.: Back home, jerking off to some YouPorn. I always feel kind of awkward getting off with Ground Zero behind me, but I’ve done worse.
11:45 p.m.: Finally respond to *her* text that I promise to see her tomorrow.
DAY FOUR
6:00 p.m.: Realize I’m supposed to speak on a panel about blogs or some shit tonight at the W. Fucking Web 2.0 conferences. Not really sure what it’s about, but these things are all the same. Awkwardly, she’s on the same panel. Practice my trademark kissy face for the inevitable photo-ops later.
9:00 p.m.: Panel went fine, though we were sitting next to each other and caressing each other’s legs throughout the majority of it. No way are we going to make it back to the apartment.
9:30 p.m.: Knew it. She drags me into the bathroom at the W Hotel bar and locks the stall. At moments like these, I wish she wasn’t morally opposed to blowjobs.
9:45 p.m.: I love a mindblowing quickie. We sneak out of the bathroom one at a time, but I’m paranoid one of Nick Denton’s spies spotted us. I Twitter something about my paranoia.
10:30 p.m.: Back at her apartment, we go at it again.
11:15 p.m.: Pillow talk, she suggests taking our relationship public, and I get pretty snippy towards her. I’m way too old to get serious…if that were to happen, engagement would be inevitable. I tell her this, but she somehow turns it into me being presumptuous. I roll over and stop responding to her.
DAY FIVE
10:45 a.m.: She doesn’t even bother to wake me up, and I’m alone in her apartment. I decide to go through her laptop email, but can’t crack her password. I Twitter something about passwords.
10:30 p.m.: Masturbating over Ground Zero, again. That’ll be the title of my memoir one day. I Twitter that I’ve figured out the title for my memoir.
DAY SIX
2:00 p.m.: Gawker writes something about me and my secret relationship. Fuck fuck fuck.
5:45 p.m.: Pick out one of my favorite blazers for dinner at the girl’s.
7:45 p.m.: Meal is just so-so, Jews are awful cooks. She looks amazing though and it more than makes up for her shitty culinary skills.
8:00 p.m.: We start making out heavily in the kitchen, and she whispers that she has a surprise for me in the bedroom. That’s all I need to hear.
8:05 p.m.: Oh my god, she’s actually blowing me! Like The Dark Knight, the actual execution is somewhat disappointing. Better than most, but still not what I expected. She doesn’t swallow, and instead runs to the bathroom to spit. What is this, high school? I Twitter that while she brushes her teeth.
8:45 p.m.: Time to reciprocate, something I happen to excel in. I wish women gave head like I give face.
9:00 p.m.: After 3 concurrent orgasms on her part, it’s time to get down.
10:15 p.m.: Totally spent, time for bed.
DAY SEVEN
10:30 a.m.: I break my rule about waking up before noon for some morning glory.
11:10 a.m.: The best part about morning sex is that I’m usually only half awake for it. As a result, I often have dreams while doing it. Today I dreamt I was at Bloghaus banging John Carney’s wife. Just kidding, but I Twitter that because I find it uproarious.
1:15 p.m.: Went to Sunday brunch; ran into John Carney and his wife. Awkward, and yes, I Twitter that too.
3:00 p.m.: Back to her place = afternoon delight! Alas, I can’t get the Starland Vocal Band song out of my head the entire time. I debate Twittering the lyrics, but decide to hold back for once.
7:40 p.m.: Back home, making plans to meet up with some of the Tumblrettes from the spin the bottle debacle.
11:55 p.m.: Fuck. Fell asleep, missed Mad Men, and have 4 text messages from Tumblrettes. I’m getting way too old for this shit. Twittered.
TOTAL: 1 act of cunnilingus, 2 self-induced orgasms (never forget), 2 subpar blowjobs, 6 acts of intercourse, 0 Tumblrettes banged, 14 Twitters.