The Trader Who Will Fly for Sex

Portrait by Matthew Woodson

12:30 p.m. I dash to JFK. I am on one of my MFM swinging adventures tonight, flying to one of our finest flyover states. I have Adult Friend Finder to thank.

12:31 p.m. My swinging M.O. is simple: Exchange recent pics of him and her. Talk on the phone. Set a date. Fly. Fuck like mad. Return to NYC. When it works, it is a very efficient way to get hot, no-strings-attached sex.

12:32 p.m. The hubby keeps annoying me with texts. Decide to humor him. After all, he is letting me have sex with his wife.

8:20 p.m. We meet at T.G.I. Friday’s. Wifey looks like her pics, which is good. Hubby seems a little nervous. I act like I’ve known them forever—give him a hearty handshake, kiss her on the cheeks. We order drinks and talk.

9 p.m. Back at the hotel. We are both undressing wifey. She has massive breasts, which I love. I play with them. Hubby is naked, playing and taking pics.

9:30 p.m. Wifey deep-throats me … awesome. Hubby alternates between taking pics and encouraging her.

10 p.m. We have sex in a variety of positions. While it feels good, there is no way I am losing control. That is a big swinging no-no, unless the couple wants that.

11 p.m. Halfhearted sex for the second round, but I am tired. I dutifully take the camera for a bit.

11:30 p.m. Saying our good-byes. I tell them to keep in touch and send me the pics so I can store/post them on my AFF profile.

Illustration by Quickhoney

6 a.m. On first plane back to NYC. I’d give the night before a B+.

3 p.m. Still horny as hell. No prospects. I jack off at home.

3:15 p.m. Surfing options. I am really into interracial sex. I have significant relational issues with African-American women. My shrink tells me that I am excluding an entire dating pool, but I can’t shake off some of my residual high-school/college issues.

11:30 p.m. Hitting my favorite bar in the East Village. I am not very good at the asinine bullshit/social Kabuki required to convince some girl to come back to my apartment.

Midnight Drinking solo. I have told my shrink that I think I am a misogynist. She tells me I should listen to women more.

Noon The Lord’s Day. Jack off.

11 p.m. At home and horny again. I fire up—it combines two aspects of porn I thoroughly enjoy: black-on-white sex and amateur swinging.

6:30 a.m. My morning wood is like clockwork. I think about my ex-girlfriend. I know, it’s an NYC cliché—the jaded New Yorker with the magical “ex” they cannot get over.

Noon Lunch on the desk. One of the admins is a sistah … with cantaloupe breasts and a slim waist; too bad she’s a cliché as a single mom. I can imagine those breasts being very fun.

7 p.m. See this banging Latina with sweater straining over fake breasts. I remind myself that I need to date a stripper before I die.

11 p.m. Horny before bed. Check out AFF. No prospects of interest.

7:30 p.m. Drinks with S., one of several older women I dated two years ago, after actively focusing on the MILF demographic.

8:30 p.m. S is telling me about her nonexistent love life. I decide to push my luck. I ask her for decorating advice, as I am trying to spiff up the bachelor pad.

9 p.m. She takes the bait. We head home.

9:15 p.m. I lose all pretense and jump her. Clothes off, I go down on her. She reciprocates.

9:30 p.m. I slap on a condom and start missionary style. She is more verbal than I remember.

11 p.m. I have three orgasms. This was great, mainly because I went into drinks not expecting anything. Grade: A-.

8 a.m. Thinking about last night. I like dating older women because they are more open in bed and less possessive. And the power imbalance: I am the younger one with the career, the six-foot-tall-and-200-pound athletic frame, the smarts, the dick, and the Platinum AmEx.

4:01 p.m. Hitting the gym tonight and prepping for a big swinging party tomorrow night.

10:30 p.m. I fire up the Dark Cavern (interracial amateur and meeting site) and Mrpeepers (amateur porn). They do the trick.

11 p.m. Tired, I crash. As I fall asleep, I think to myself: I need a new fling and some regular sex.

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Trader received 59 comments

As a black woman I would love to know what his “issues” are. I think the first one is actually writing “sistahs.” I hope he gets somewhere with therapy.

Inherently soulless, shallow, and shameless. It reeks of a guy desperately unhappy with his own life. A sex addict trying to replace an emptiness. Get some help!

If I was younger and single I would be all over the Internet sex thing. It is almost like the free love of the sixties has come back, but in a cyber kind of way.

I simply can’t believe this man is in charge of other people’s money. You can see why the market falls while this guy spends his weekends ignoring the markets and surfing the web for porn.

The Trader Who Will Fly for Sex