sex diaries

The Finance Guy With a Girl (or Two) Every Night

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Finance Guy With a Girl (or Two) Every Night: 34, male, Midtown East, financial consultant, single, straight.

9:40 a.m.: Awakened by a call from a stewardess friend of mine who I met online years ago. She’s Filipino, tall, gorgeous, lives in the Middle East, and calls me whenever she’s passing through for a night. I let it go to voice mail.
9:42 a.m.: More calls from her derailing my desire to sleep in. I debate turning off my phone. She’s not usually this pushy so I figure something is amiss and pick up. Turns out she was on her way to visit her new boyfriend in the Midwest and is now stranded in NYC and needs a place to stay.

11 a.m.: She arrives and gives me a sob story about her boyfriend being unsure he can meet her. Nonetheless, she tells me she has to be “good” for him. She climbs into bed and lets me play with her fake breasts and gives me a blow job.
7:30 p.m.: She decides she will spend the night and wants to go to a swingers party with me. We went to one two years ago (her first), where she kissed her first girl and loved it. It’s slim pickings on this night, and we settle on one that allows single men, which will be a new one for me.
11 p.m. We leave for the midtown soiree after having a few drinks at my apartment. She wears a tight black dress showing off her long legs and tight body. I’m excited at the possibility of the night.
11:30 p.m. We arrive at the midtown space and are greeted by a female porn star wearing nothing but a belt at the coat check. I realize I’ve been to this space before for a different swingers party. I always think I haven’t been to that many naughty parties but am starting to reconsider that notion.
12:30 a.m.: Sadly, the night is not going as planned. There is porn playing on the TVs (starring the coat-check girl). Almost all of the attendees are single men, and they are not shy about masturbating openly while staring at my date. It’s creepy, but we decide to have one more drink.
12:40 a.m.: A very attractive couple shows up with the owner trailing them with a bottle of vodka. The single men circle like sharks. They go into an empty room with two couches. I sense a window of opportunity and join them in the room on a couch facing theirs with my Air Vixen.
2 a.m.: She’s a beautiful blonde ex-stripper, and he is a good-looking surgeon dressed in a suit and tie, which is way overdressed for this place. She is clearly not shy, and you can tell between them whose idea it was to come. They are long-distance and decided to rendezvous in NYC for the weekend. It’s his first event like this. He’s nervous and freaked out by the men jerking off to his girlfriend. I don’t blame him.
2:30 a.m.: After finishing most of the bottle and watching our dates molest each other, they invite us back to their room at the Waldorf Astoria. They flag a limo to take us. I like how this couple rolls. I used to do the spontaneous drunken limo thing when I first moved to New York ten years ago, but it’s been awhile and I forgot how posh it feels even if you’re only going a few blocks.
3:15 a.m.: We settle onto the couch in their room, and most of us are a drunken mess. Air Vixen wants us to put on lesbian porn since those sites are blocked in the country she lives in. Nobody objects.
3:30 a.m.: The girls strip each other and remove our pants. We get simultaneous blow jobs with them pausing to kiss each other. At some point, the fancy glass coffee table gets knocked over with everything on it. We decide to move to the bedroom.
3:45 a.m.: We all end up naked in bed. Air Vixen doesn’t miss the chance to go down on her second girl ever. It’s a beautiful sight, and my date is supremely aroused by it. I’m happy we decided to stay at the party.
3:50 a.m.: Just when I’m gearing up for the climactic finish, Air Vixen surprisingly says it’s time to go. I initially resist and then join her back in the living room. She finishes me off with her mouth and tells me afterward that the beautiful stripper was dry where it counts, and she wasn’t feeling it all of a sudden. We collect our clothes in the living room that looks like a war zone, and I write them a message saying goodbye. I go home, both satisfied and disappointed, if that’s possible?

12 p.m. Wake up horny with my head full of naked sexy images. Air Vixen is gone. I masturbate.
8 p.m. Texting three different girls for their plans that night. I’m exhausted from the previous night so want something low-key. Surprisingly, the best offer comes from my ex-boss, who wants to grab comfort food, so I opt for fried chicken on the LES, which scratches me where I itch.
10 p.m. One girl who I used to hook up with regularly is recently broken up and with her girlfriends a few blocks away. A tall blonde South African I met at a New Year’s Eve party is out in midtown near my apartment. I grab a beer and watch tennis while I mull it over.
11 p.m. I tell the South African to meet me at my place.
12 a.m.: We spend an hour having lazy foreplay and sex by candlelight. I pass out (after I blow out the candles). Exactly what I wanted.

1 p.m. A cute brunette I met online and have been on two dates with asks me my plans for the night. She is a nurse, lives in New Jersey, and has the next day off from work. I visited her on the second date and left the next morning five orgasms later. I tell her I have no plans, and she resolves to come in.
3 p.m. I used to feel weird about having a different girl in my bed on consecutive nights (in this case, three nights). Eventually I started thinking I was living every man’s dream. Now, I just make my bed and clean up condom wrappers and other evidence. I wonder if I’ll ever be able to have a serious relationship.
7 p.m. We see a movie, have drinks, and she spends the night. Very relaxed, which I like.

4 p.m. Plans fall through with a Brazilian girl I went on a first date with two years ago. I take a night off from women and go play basketball, which temporarily neutralizes my libido.

3 p.m. A nurse I’ve been flirting with online for months texts me that’s she’s getting off at seven. Through our Facebook chats she’s told me she’s been with only two men, can deep throat, and is capable of ejaculation. The last would be a first for me, and although she’s very cautious and nerdy about meeting, I am intrigued.
7 p.m. She gets off work, and I try to get her to meet me at my place, but she won’t bite. We rendezvous at the W lobby bar in midtown, which has been my go-to place for first dates for years. I like the sexy vibe created by the fireplace, low music, and couches.
9 p.m. A couple drinks later, we leave and I invite her back to my place. She accepts, but insists in the elevator that she is not going to sleep with me. She gives me a 30-minute massage complete with hot oils, which is so good I almost fall asleep.
10:15 p.m. After some kissing and caressing, she slips her panties off and we are both naked. I can’t tell which I like more, the chase or the sex, but I think it might be the former.
12 a.m.: We have sex twice, but no ejaculation from her. Everything else is as advertised. She tells me she had fun being a slut, which makes me laugh, and she leaves at six to go to work.

6 p.m. I meet the aforementioned Brazilian girl and her roommate. We have appetizers and many drinks at a midtown hotel bar.
9 p.m. The night is going well, and I get a good vibe from both of them. In my warped mind I am thinking threesome but know that since they’re roommates I’ll have to choose. At the moment, it’s too much for me to deal with so I don’t stop them when they want to retire.
11 p.m. I decide to keep the night going and have dinner at Nikki. I chat with the hot Swedish waitress and her cute blonde Polish friend.
1 a.m.: Very drunk and dancing with the Polish girl. Three girls texting me to come meet them. While it’s probable I can take this girl home, I’ll leave that for another night and go with the sure thing. I tell the South African to meet me at my place in half an hour.
1:30 a.m.: She meets me at my apartment. She talks about giving me a massage but instead gives me a twenty-minute blow job (she’s very good), and then we have sex.

7 p.m.: Getting ready for an erotic party that night for couples and single women. The theme is Roaring Twenties so everyone is expected to dress up in tuxes, as flappers, etc. Prior to the party there will be a panel of sexperts and producers discussing a newly made adult film. My date, a sexy Latina I met online and have known for six years, arrives. She is bicurious, and we trust each other at these events, which is the most important thing.
9 p.m.: “Monogamy kills sexual desire.” “Most relationships eventually present lack of mystery and obstacle.” “Ashley Madison is the No. 1 dating website.” A few of the quotes from the hour panel questioning sex and societal norms. Very insightful discussion that I will ponder for days to come.
12 a.m.: Everyone strips to their underwear. Crowd is gorgeous, and a potent sense of excitement is in the air.
1 a.m.: Most couples are playing with each other or other guests. Sometimes when things are going well at those parties I get that feeling that there’s nowhere else in the world I’d rather be at that moment. A feeling I don’t get nearly enough and find myself constantly striving for.
3 a.m.: I pleasure a few women and have sex twice with a woman (anal the second time) with glitter on her chest (from another woman who was on top of her) and a tongue piercing. She takes my number and Facebooks me two days later. Go home with my date and a farewell gift of a vibrator.

TOTALS: six girls kissed, four acts of oral sex performed, six acts of oral sex received, five acts of intercourse, two acts of anal sex, seventeen orgasms.

Would you like to take part in the glorious tradition that is the New York Magazine sex diaries? Just send an e-mail to with your contact information and why you think you’d make a good diarist. If you’ve got what it takes, we’ll be in touch!

The Finance Guy With a Girl (or Two) Every Night