sex diaries

The Successful Ad Guy Who Uses His iPhone in Ways Steve Jobs Probably Didn’t Intend

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Successful Ad Guy Who Uses His iPhone In Ways Steve Jobs Probably Didn’t Intend: male, 23, East Village, single, straight.

11:30 a.m.: I wake up horny. This must be because I got high the night before and didn’t bother to rub one out before bed. I fantasize about a typical hipster girl. All she wants to do is suck and have sex. She talks dirty. Clean up.
1:20 p.m.: I’ve recently begun using Internet dating. I check my in-box. No new messages. I look over the messages from the girl I’m supposed to meet tonight — L . I look at her photos, deciding whether or not she’s attractive. I’m excited.
2 p.m.: I want to be in a relationship. I’m open and willing to commit but I can’t find a girl who is, too. I do the casual thing because it seems to be what I end up with.
3:17 p.m.: Watching TV. A commercial with a very attractive redhead comes on and I decide I wanna fuck a redhead. I plug in my computer and begin looking at free porn sites, typing in redhead in all the search boxes.
3:37 p.m.: Haven’t found the right one. I remember a conversation I had on a recent date about our generation having too many options and how saying yes to one thing means giving up something potentially better later. We’re never content.

3:41 p.m.: I find a girl I’m content with, masturbate to her video. Watch TV.
4:11 p.m.: I debate masturbating again because alone time when you have a roommate is sometimes rare. Check the dating site. I have a message. A girl agrees to drinks on Sunday. A booked weekend, this makes me happy.
4:15 p.m.: I masturbate to a porno I’ve seen before. I like when the girl talks dirty but not when the girl seems to be making up nonsense.
7:32 p.m.: Get ready for the date.
8:25 p.m.: When I meet L at the restaurant I’m already turned on by her glasses (very nerdy looking). She’s very thin and about my height. Lately I’ve been into tall women.
10:34 p.m.: We’ve made out several times. I really want to have sex with her but at the same time I really like her; she’s great company and I’m very attracted to her. I offer for her to come back to my place. She kindly says no and tells me that she wants to take things slow.
11:05 p.m.: I walk her home. It’s a good walk; she holds my arm, laughs at people on the street. I think to myself, “This could be us. I could have finally found something that works.”
1:30 a.m.: Back in the East Village, I masturbate to the thought of my date’s body, what it must be like to be with her, in love with her, having sex while in love with her.

10:30 a.m.: I wake up hard. I rub one out quickly, thinking about a friend of mine from college.
10:50 a.m.:I think about meeting my second Internet girl — Rebecca. I haven’t been with someone in a while, hence the whole Internet-dating thing.
1:20 p.m.: I get back on the dating site to take a look at some of Rebecca’s photos. She seems to have a tight little body and a quirky personality. I tug on my dick a bit looking at her picture. I don’t want to “poison” the idea of her yet, so I stop.
5:45 p.m.: I get off before I get in the shower, thinking about my date from last night and then some random shots of girls I know. Sometimes it’s like a slot machine of sexual fantasy. Whenever I finish, whoever I was thinking of is the winner of my imagination.
7:30 p.m.: I wait outside the bar. I see Rebecca walking up. I’m already excited about this.
8:20 p.m.: To my surprise, this girl is amazing. We’re both feeling good. We get into some serious conversation. Then somehow we tangent out into talking about sex and how necessary it is in our lives.
9:12 p.m.: We start making out at the table. We’re both getting turned on. She looks at me and says, “I want you.” SOLD!
9:20 p.m.: I text my roommate: “Condoms! In bathroom. Please. Stat. Home in 5-10,” to which he responds, “I’m on it. Done.”
9:28 p.m.: I open up the medicine cabinet to grab condoms (great!) and lube (thanks?).
9:30 p.m.: I lock the door and I’m already on top of her. I take off her shirt. Her tits are small and perky, very sexy. I get even harder.
9:34 p.m.: She takes off my pants and lays me down on the bed. She takes out my dick and starts sucking. I didn’t even have to ask. After a few more moments of sucking I decide I want to be inside her.
9:38 p.m.: I think that maybe she should have shaved a little bit. It’s not bad, just a bit unmanaged. I go down on her. She moans loudly.
9:43 p.m.: I jump on her as if I hadn’t had sex in years. After a while, she keeps checking to see if I came. Because I’m pretty buzzed, I know this isn’t going to happen. She starts begging for me to. I fake it.
10:27 p.m.: I pull out. My stomach rumbles. Something is very wrong.
10:32 p.m.: In my bathroom. Frantic. I turn on the sink really loud and get down on my knees in front of the toilet.
10:34 p.m.: The most violent vomit I have ever had in a long time has just occurred. I can’t believe this is happening.
10:40 p.m.: She is already dressed. I try to convince her to stay and she says she needs to wake up early. I try to pull her back to bed and she finally admits, “I just heard you vomit.” Damn.
11 p.m.: Walk her to the train. We kiss. As I put my headphones on I swear I hear her say “I hate you.” Think of ways to remedy this. I’m already thinking about a sequel.
12:03 a.m.: I masturbate thinking about the sex I just had. Go to bed.

8:12 a.m.: Wake up. Contemplate masturbation.
8:24 a.m.: Waiting for shower to heat up. Start tugging on my dick. I spin through my mental spank Rolodex and think of any girls I’d like to beat off to. I’m bored with all the girls I have in my Rolodex. I attempt to think of girls who are friends that I haven’t banged, but I lose interest. I need to find new girls to bang.
12:01 p.m.: At work. I glance over at a co-worker’s ass as she bends over to talk to someone. I fantasize a late night at the office, a gathering or party of some sort, we find ourselves in a quiet corner, etc.
9:27 p.m.: Officially hungry for sex.
12:45 a.m.: I get horny and decide to masturbate.
12:50 a.m.: On rare occasion, the fantasy revolves around being with a girl who cares about me, maybe loves me even. I haven’t had a meaningful relationship in a long time.

8:21 a.m.: Naked, waiting for shower to heat up, start jerking it. Uninspired and ditch the idea.
9:17 a.m.: I fantasize on a few women as they pass, mostly about getting head from them or bending them over.
1:40 p.m.: I have a strange desire for a blow job all of a sudden.
2:30 p.m.: I check through text messages, hoping that maybe I’ll get a response from the girl I had sex with on Sunday. I really would like to have sex with her again.
3 p.m.: I text a girl I’ve dated a few times to see if she wants to hang out tonight for a little bit. She works on the same block I do, but lives in Queens. She says she would love to.
7:12 p.m.: She meets up with me as I’m finishing up at the laundromat. I meet her outside and give her a kiss. I immediately notice she’s wearing a knee-high skirt, with gray stockings and heels. I already want to pin her up against the wall.
7:20 p.m.: After talking for a bit she finally blurts out that she isn’t looking to date anyone right now. I’m immediately crushed because we’ve already been on three dates. I don’t get why not one girl is interested in sticking around.
7:28 p.m.: My laundry is almost done and we’re still outside “trying to talk.” She won’t stop trying to “be my friend.” I tell her up front that friendship is not what I was looking for. I tell her I can try, but I can’t promise anything.

4:03 a.m.: I’m up, very tired. My flight is at 6:30 a.m. Going to visit my older brother who I haven’t seen in over a year.
11:30 p.m.: Land, meet brother.
12:20 p.m.: We get lunch at a family-style fried-chicken restaurant. I haven’t really seen any attractive women in this state yet.
2:20 p.m.: I go to the bathroom as if I have to take a dump. I use my iPhone to look up porn and masturbate.
12:23 a.m.: After meeting a slew of new family and eating even more chicken, everyone gets ready for bed. I go into the bathroom to brush my teeth. I take out my iPhone again, look up some porn, and let another one out.

2:30 p.m.: While eating at Joe’s Crab Shack with family, I think about the lack of women I’ve seen thus far.
5:45 p.m.: Saying good-bye to everyone, heading back to my brother’s place.
11:25 p.m.: Everywhere takes FOREVER to get to. We go to see a movie. There are a lot of high-school kids at this theater for this movie. Finally something to look at. I check some girls that are scantily dressed.
12:46 a.m.: I take a bathroom break. I see a girl with a great ass and jet-black hair. I think about a crazy scenario in which we have crazy random sex.
2:04 a.m.: Back at my brother’s apartment, I use the bathroom to masturbate before I go to bed. Thank God for my iPhone.

10:30 a.m.: I’m the first one up. I lay in bed thinking about the girls who don’t want to date me, and about how lonely I feel. Then I think about Rebecca and how much feeling rejected sucks. Then I think of L and why I haven’t heard from her in a while.
11 a.m.: I realize that the hottest girls I’ve seen thus far are all black or mixed. I typically go for white girls, but in the South I think I’d have to play the opposite.
8:02 p.m.: We decide to go to Hooters, pick up some wings, and drink beer and eat at his apartment.
9:23 p.m.: At Hooters, the waitresses are hot and whorish. While not every waitress is ideal, there isn’t one here I wouldn’t fuck.
11:35 p.m.: I’m a little upset that the night was so drab. I wanted to go out, get drunk, meet some Southern girl who would be impressed by some New York guy and then we’d sleep together.
11:45 p.m.: I masturbate in the bathroom and then go to bed.

TOTALS: Thirteen acts of masturbation, two dates, one act of intercourse, one act of fellatio, one act of cunnilingus, one instance of post-coital vomiting.

The Successful Ad Guy Who Uses His iPhone in Ways Steve Jobs Probably Didn’t Intend