sex diaries

The Trader Who Will Fly for Sex

Once a week, Daily Intel takes a peek at what your friends and neighbors are doing behind doors left slightly ajar. Today, the Trader Who Will Fly for Sex: 27, male, West Village, straight, single.

9 a.m.: Wake up hung-over and stumble to the bathroom. I took the day off for my mental health, but it doesn’t mean I don’t focus on the markets. I watch them like a hawk both for my personal account, which has taken a sizable hit, and the firm.
11 a.m.: Working from home and in constant communication with my team. Defeating the purpose of taking a day off.
12:30 p.m.: Quick lunch by my lonesome. Overnight bag packed. I dash to JFK. I am on one of my swinging adventures tonight. I have not been in a serious relationship since 2004. I am generally focused on sex and sexual experiences.

2:30 p.m.: Flying to one of our finest flyover states to participate in a MFM threesome. I have Adult Friend Finder to thank.
12:31 p.m.:However, hubby is annoying me. 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 NSA sex. I am well versed in great airport hotels that offer discretion and value.
12:32 p.m.: Hubby keeps annoying me with texts — “she’s so wet for you!” Decide to humor him. After all, he is letting me have sex with his wife.
5 p.m.: Hotel. It is not the regular hotel I use for my encounters — that hotel was booked for a convention. I am annoyed; there is no room service, and I’m in the middle of effing suburbia.
7 p.m.: Downing Coronas at the local Applebee’s.
8 p.m.: Hubby calls. I tell him the Applebee’s is very crowded — with families and teens. A young black man meeting with a white couple raises eyebrows in certain places. It is probably best if we meet at the T.G.I. Friday’s.
8:20 p.m.: They show. Wifey looks like her pics, which is good. Hubby seems a little nervous. I act like I’ve known them forever — him a hearty hand shake, kiss her on the cheeks. We order drinks and talk for a bit. It is all about making sure that all parties are comfortable and relaxed.
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. MILFs. I start fucking her. We are getting verbal (this is part of the fantasy/roleplay) — I am asking her if this was what she wanted — big black cock. 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.
10:02 p.m.: Finish.
11 p.m.: Falf-hearted 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 I enjoyed it, which I did, but I like playing with my regular couples better. I tell them to keep in touch and send me the pics so I can store/post them on my AFF profile. They leave, I crash. I am on the first flight back to NYC in the a.m.

6 a.m.: On first plane back to NYC. I’d give the night before a B+. That said, I needed it. Plus, time away from NYC allows me to relax and reflect.
3 p.m.: Still horny as hell. No prospects. I jack off at home, watch some college football, and exchange e-mails with a few prospects. I have had sex with women off of Craigslist,, AFF, the Dark Cavern, and the old Yahoo groups. The Internet allows me to cut the B.S. and get to the point.
3:15 p.m.: Surfing options. I am REALLY into interracial sex — mainly black guy on white girl. I know that as a former black nerd who likes middle-class white girls, I am at a bit of a competitive disadvantage, but with that said — and I am being honest here — I have significant relational issues with African-American women. My shrink tells me that I am excluding an entire dating pool — and one that will probably give me the sex I seek — but I can’t shake off some of my residual high-school/college issues.
5 p.m.: Gym. This is one of the best times to grab a workout. No eye candy, but people aren’t hogging machines either.
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. I refuse to jump through hoops for flighty NYC chicks.
Midnight: Drinking solo. I have told my shrink that I think I am a misogynist. I like her. She is likely the wielder of the strap-on in her same-sex relationship, but she is empathetic and straight to the point. She tells me I should listen to women more.
12:30 a.m. Go home solo. My thesis is that I am unable to control the environment in a bar, and that results in my low hit rate. When I get a chick one-on-one — either on a date or Internet encounter — my hit rate gets a lot higher because I can control the environment and the “message,” so to speak. But I might be confusing causation with correlation.

Noon: The Lord’s Day. Jack off.
1 p.m.: An AFF couple from New Jersey winked at me again. They are only into bareback play. Now, I have done some stupid things in my sexual odyssey, but I am very careful about bareback sex. Plus, they did not answer my question about STD tests. Her pictures show she is quite enthusiastic about BBC, but I put her on the back burner and jack off again.
9 p.m.: Beers and watch HBO. I don’t like the pseudo-virginal Anna Paquin in True Blood for some reason. I really thought she was smoking hot in Finding Forrester, though.

8 a.m.: At work. My Latina admin comes in. While I do not shit where I eat, I do enjoy the dirty thoughts that come to mind. She is petite — five foot two at the most and around 125 pounds that she wears well, with massive D cups. I am still not sure if they are real or if she had a good doctor. Who cares … she would be fun regardless.
7 p.m.: Gymin’ it again. I love admiring the bodies of these “effortless perfection” style/ex-sorostitute chicks that live in my neighborhood. They hit the gym like clockwork and really work hard at taking care of themselves. However, the realist in me knows that girls like that make you pay the “girlfriend tax.”
11 p.m.: At home and horny again. I usually masturbate once to twice a day. 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. She was hot, smart, and the only woman who has ever made me want to be a better man or been considered as the future mother of my kids. Now my life is one of feast and famine.
6:42 a.m.: Goddammit, I love and hate New York all at the same time.
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, much like my other goals of visiting Brazil and starting my own investment firm in five years.
11 p.m.: Horny before bed. Check out AFF. No prospects of interest. Yuvutu is another good resource for amateur porn. Load it up, let it fly.

7:30 a.m.: Hump Day. Oh well. I am backing up a colleague, so I get to work a little earlier than usual. I am a politics junkie so I spend a lot of time on before working on my morning briefs.
7:15 a.m.: Think about the fact that if Obama were attached to a white woman, he would never have made it this far. Oh well, with all the dirt I have done, politics was always out of the question, plus there’s no money in it.
7:30 p.m.: Drinks at the Pegu Club with S, one of several older women I dated two years ago, since actively focusing on the “MILF” demographic. We generally hang out every few months, catch up over drinks and shoot the breeze. She is one of the rare women I hang out with if I am not sleeping with them — she wants a serious relationship and knows I am not that man. She also isn’t getting any younger and that’s a harsh reality. She just seems to have had bad luck with the guys she has dated.
8:30 p.m.: S is telling me about her nonexistent love life, her career plans, and the lack of chemistry with other 40-year-olds she dates. 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. I was well trained in the art by my ex-girlfriend and I am great at it. She reciprocates.
9:30 p.m. I slap on a condom and start missionary style. She is more verbal than I remember. I notice something. White women of a certain age — in my experience — use “cock” a lot. Younger girls use “dick.” Brothers generally use “dick” except when doing the whole “bbc” thing.
11 p.m. I have three orgasms. This was great, mainly because I went into drinks not expecting anything. Grade: A-.

8 a.m.: Putting my time in at work and thinking about last night. I like dating older women because they are more open in bed and less possessive. And since they are older, flings come with an expiration date. And lastly, 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. I don’t deal with social Kabuki. If they want to get down, they do. If not, they don’t.
4:01 p.m.: Hitting the gym tonight and prepping for a big swinging party tomorrow night.
10:30 p.m.: Early night, as I want to get some rest before hitting the town hard tomorrow. I am horny, again. I fire up the dark cavern (Interracial amateur and meeting site) and Mrpeepers (amateur porn) 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.

TOTALS: Three acts of intercourse; two acts of cunnilingus; two acts of fellatio; six acts of masturbation; one act of flying to another state for NSA threesome; two acts of gym exercising; two acts of ogling the office administrative staff.

The Trader Who Will Fly for Sex