sex diaries

The Single Guy Juggling Five Girls in One Week

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Single Guy Juggling Five Girls in One Week: 29, male, single, East Village, straight.

10:17 a.m.: Sitting at my desk in a haze from the weekend. Single life is great, but it’s also fucking exhausting. I’m hanging with Redhead on Tuesday, taking Brunette to a concert Thursday, and I have two different online dates tentatively planned. I also need to see Gabs at some point and follow up with this girl I took home from a charity event last week.

1:25 p.m.: Blondie invites me over for dinner. We’ve been dating on and off for years, whenever both of us are single. She’s very much in love with me, and the sex is just amazing. But I know she’s not “the one,” and I purposefully keep her at a distance. I waver between guilt, feeling like things could work if I just chilled the fuck out, and extreme fear of commitment. Basically, when it comes to love and relationships, I am utterly insane.
1:30 p.m.: I accept Blondie’s invitation.
7:14 p.m.: I arrive at her place for dinner. She is cooking and wearing a ridiculously hot dress; her ass looks amazing. I’m already fighting the urge to lean against her and let my hands wander.
8:19 p.m.: Finishing our wine and talking about our families. It’s clear she wants more than a weekly hangout and bone sesh, but I just can’t bring myself to commit to anything more.
8:50 p.m.: Blondie is on the couch when I come out of the bathroom. I kiss her and then she starts to give me head while I’m standing up. Eventually, I pull her dress above her head, pick her up, and carry her to the bedroom.
9 p.m.: After I go down on her on the bed, we go at it in missionary. Then we roll over and she rides me methodically until she has an orgasm. I love a woman who knows her body. I can’t hold it anymore and finish off just after she does.
9:37 p.m.: I can tell she is dying to go again, but I’m just exhausted. So I give her more head instead. I can always tell when she’s about to come because her hands start to shake. She pulls the shit out of my hair when she has an orgasm, and it always hurts. But I love giving head. We listen to some music and fall asleep.

6:45 a.m.: Alarm is sounding and Blondie is guaranteed to be horny. I hate morning sex, but she loves it and doesn’t care that I hate it.
6:47 a.m.: All hopes of a quiet exit are dashed. I feel her hand cup my balls, and she starts stroking me. At least she knows how to get me hard! I spoon her and have sex with her from behind. Then I roll her over and we finish doggy-style.
10:54 a.m.: Thinking I need to have a talk with Blondie. As great as the sex is, it’s just not fair for me to string her along, and the guilt is starting to eat away at me. I wish I could just love her like a normal person.
2:26 p.m.: Plans for the rest of the week are set. I’m starting to entertain the possibility that I might have sex with five different women this week.
4:31 p.m.: Making contingency plans in case Redhead’s “thing she wants to tell me” has nothing to do with sex. I plan to bail early if things aren’t going well. Gabs is attending a party uptown and will certainly be DTF later. I tee her up for a booty call just in case.
6:15 p.m.: Redhead needs to reschedule. I’m really not disappointed.
7:04 p.m.: Arrange to meet Gabs at 9. We met about a month ago on a drunken Saturday afternoon and fucked that night.
9:25 p.m.: I am at Gabs’s apartment giving her a massage, which always makes me hard. I roll her on her back, and she goes straight into giving me a blow job. Talk about an alpha-male position. I hold the back of her head and finger her with the other. I am in complete control of her, and I can tell she loves it.
9:32 p.m.: Having very hot missionary sex. She is very loud.
9:34 p.m.: I’m about to finish myself when Gabs attempts to slip a finger in my ass. I pucker up instantly and squirm like I’ve been Tasered. I hate ass play. She laughs at my skittishness and takes her hand away, and I finish shortly after.

6:45 a.m.: Alarm sounds, and I quickly jump out of bed knowing that Gabs will try to sexually assault me if I don’t. I could probably muster up the energy for a morning breath-laden bone sesh, but I’m already thinking about tonight’s date with Online Girl. I tell her I have an early meeting and skip out the door.
11:16 a.m.: Figuring out who I haven’t followed up with this week. Since my girlfriend dumped me in October, I have met more than twenty girls and had sex with approximately eleven of them (including a few former flings). Most, if not all, of these encounters have a shelf life of three to five weeks. Juggling all of it is complicated and exhausting, not to mention expensive. I know that such behavior is not normal and likely a mechanism for avoiding true intimacy. I know I am capable of loving the shit out of someone if I could just get out of my own way. But hey, no rest for the weary, right?
1:33 p.m.: Take a walk during lunch, and it’s beautiful outside. I’m starting to get excited for eye-fucking weather. I hope Online Girl is wearing a sexy outfit tonight.
7:32 p.m.: Getting an awkward vibe from Online Girl on our date. We’ve hung out a few times, fucked a few times, and I genuinely think she could be GF material. But she’s been distant, and her body language speaks volumes. I have a strong feeling I won’t be getting into her pants tonight.
8:15 p.m.: Online Girl says she has to wake up early, which is code for “you’re not getting any tonight.” I’m disappointed things haven’t worked out, but I’m also not crushed about it. We have an awkward hug goodbye. I don’t expect I’ll ever see her again.
9:07 p.m.: Texting with Online #2 about our Friday plans. Despite the fact that we’ve never met in person, she wants to meet up in a group, and we both agree to bring single friends.
9:48 p.m.: Seriously considering jerking off, but my Internet just went out. There is no hope without porn, so I go to bed.

7:04 a.m.: Consider a morning jerk sesh but still no Internet. I also want to have a full magazine in the chamber for Brunette tonight. Brunette, petite with perfect tits, is perhaps the hottest girl I’ve ever had sex with.
11:02 a.m.: E-mailing my buddies and trying to get them interested in hanging out with Online #2 and her friends. I promise them they are hot, a complete lie since I have no idea what they look like. One of them replies all to my e-mail, “Get ready for Slut-fest 2011!” I promise we are not assholes. This is just how guys talk to each other.
7:31 p.m.: Brunette and I are absolutely pounding drinks. She seems to be in a relaxed mood, and we keep brushing up to each other. I place my hand on her back and she accepts my affection. I instantly get a semi.
9:40 p.m.: Brunette and I are quite drunk and making out everywhere.
11:30 p.m.: At Brunette’s apartment in Queens, ripping each other’s clothes off in her kitchen. I am completely shit-faced. We start having sex on the countertop.
11:38 p.m.: In Brunette’s bedroom, having an old-fashioned hair-pulling, ass-slapping, drunken romp. We can see our reflections in her mirror. We switch to doggy-style, and I have a Patrick Bateman moment in front of my reflection. I’d be lying if I said I wasn’t flexing. Brunette reaches between her legs and holds my balls while I finish.
11:42 p.m.: Brunette is resting her head on my chest, and we are about to pass out. Lights are still on, and I realize that I just fucked with my socks on. Oops.

8:48 a.m.: Wake up in a head-splitting haze, but also realize that I am hard, which is a rarity for me in the morning. I roll on top of Brunette, and I can tell that she has the same idea. We have missionary hangover sex and I come pretty quickly.
9:04 a.m.: Brunette’s apartment looks like a murder scene. Clothes and jewelry are everywhere. I briefly recall last night’s shit-show before realizing I’m late to work. Kiss Brunette goodbye and split.
5:37 p.m.: Texting back and forth with Online #2 to figure out a meeting place. We decide on an East Village dive. Considering how hung over I am, I can’t believe I’m going out tonight, but I have a feeling things could get interesting.
10:17 p.m.: Online #2 and her friends arrive. They are all quite hot, but instantly give off a meatpacking-club-scene-cokehead vibe. Not good. They join us at a table and we pair off.
11:01 p.m.: After nearly 45 minutes of painful and awkward conversation, my three friends get up to buy a round. One leans in and whispers to me that he “can’t take this shit anymore. These girls are crazy.” I nod in acknowledgment and tell Online #2 I’m going to join my buddies at the bar for a minute.
11:05 p.m.: We all split out the front door without saying goodbye. Kind of a dick move, but those girls deserved it. I can’t stand that whole scene.
11:16 p.m.: I send a “hey what are you up to” text to every single girl in my phone, except for Blondie. I know she hates it when I booty call her. Gabs agrees to meet up with me later. After that debacle with Online #2, I’m playing it safe tonight.
2:15 a.m.: Meet Gabs at my apartment. She pushes me onto the bed and immediately starts blowing me. She has great attention to detail and uses her hands very well. After about two minutes, I pull her up so she is straddling my face, and I return the favor. We fuck with her on top, and she has at least two orgasms. I take pride in that. I finish and we pass out.

10 a.m.: Surprisingly not hung over. Thankfully Gabs has to leave, and I pretend to still be asleep until she does.
11:47 a.m.: I can already tell tonight is going to be an utter shit-show. Eight of us, all guys, have dinner reservations. I’m not making plans with any girls tonight and instead am hoping for the best.
2:16 p.m.: Blondie texts and says she is annoyed that I haven’t been in touch all week. This is part of our usual cycle. We hang out for a while, and one of us gets too attached. Then we argue, don’t talk for a while, and eventually rekindle things. I apologize to her and make plans to see her tomorrow. Brief pangs of guilt subside.
10:15 p.m.: After several beers, multiple tequila shots, group singing, shit talking, and one massive vomiting session in the bathroom, my buddies and I stumble out of the restaurant. I am teetering on the edge of a blackout. Naturally, we head to a bar.
11 or 12 something: Dancing and making out with some girl. I have no idea what her name is or how old she is. I am completely wasted. I reach into her jeans and finger her on the dance floor. She is not wearing panties.
2:43 a.m.: Back at my apartment with No-Name Girl. My buddy is hooking up with her friend in my kitchen. No-Name Girl is on my couch with her jeans around her ankles, and I have her feet above her head. She asks if I have a condom, and I grab one. But I really have to piss, so we fool around a little bit more and I tell her to wait while I use the bathroom.
2:49 a.m.: I come out of the bathroom and No-Name Girl, her friend, and my buddy are all gone. I am quite perplexed but way too drunk to properly analyze the situation. So I pass out.

10:06 a.m.: Very hungover and trying to remember what happened last night. There are a few opened, mostly full beers sitting around my apartment and an opened but unused condom on my coffeetable. I recall coming home with my friend and those two girls, but I have no idea why they all left. I try calling my friend to make some sense of what happened, but no answer.
11:22 a.m.: Friend calls me back and tells me that when I went to the bathroom, No-Name Girl rushed into the kitchen and wanted to leave right away. So he left with them and split a cab home. Neither of us have a clue why she wanted to leave. Basically, I have no idea who this girl is, how old she is, where she is from, or why she left so suddenly after apparently wanting to come home with me. In fact, I probably wouldn’t recognize her in a lineup right now. Life is a mystery.
6:07 p.m.: Blondie texts me to say she wants to hang out tonight. I’m exhausted, but hanging out with her always somehow makes me feel better.
8:27 p.m.: Sunday whammies. All of this running around really isn’t very fulfilling. Though it can be fun at times, I can’t help but feel like I’m selling myself short. I really do want a girlfriend and somebody to love.
8:29 p.m.: Jerking off to Jenna Haze on PornHub. She looks like an ex-girlfriend of mine. I broke up with her after six months for reasons I don’t understand.
9 p.m.: Pop an Ambien and crash hard.

TOTALS: Six acts of intercourse, three acts of received oral sex, four acts of administered oral sex, one Patrick Batemen moment, one squirming reaction to ass play, one dance-floor finger blasting, one mid-date ditching, and one Sunday guilt-laden masturbation session.

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The Single Guy Juggling Five Girls in One Week