sex diaries

The Woman Sleeping With One Colleague While Pursuing Another

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Woman Sleeping With One Colleague While Pursuing Another: Female, retail manager, Crown Heights, 30, heteroflexible, single.


7 a.m. So begins another hectic week at the office. The only spot of entertainment is a sexy text message from Mr. White, a colleague. He wants to see me later. He would go down in history as the hottest guy I’ve ever slept with, if indeed, I’d ever slept with him. He has a great body, perfect dreadlocks, tattoos, and a sexy French accent … yet I’m not super attracted to him. I think it’s because I’m still having drama with my ex-fiance, and hung up on Mr. Pink. I sext back and forth with Mr. White, to no avail.
3:10 p.m. I decide to give Mr. White the brushoff. Besides, I have a date with Mr. Blue, a tall, very cute Jewish physician, tomorrow. He’s my primary rebound fling. I ask my boss if I can come in later because I expect to be up late. She smiles and says, “sure thing.” I love my boss.


6:55 p.m. I’m horny as hell but I’m careful not to masturbate. Instead, I tidy up a little, take a shower, get gussied up and knit while I wait for Mr. Blue.
9 p.m. Mr. Blue rings my doorbell right on time. His punctuality makes me even hornier. I hang up his motorcycle jacket and show him around. We chat endlessly while we drink scotch. I drink mine neat. He likes his on the rocks.
1:45 a.m. “I’m ready to kiss you,” Mr. Blue says suddenly, much the same way he did on our first date. His awkwardness is endearing. We go to my bedroom and my jeans quickly come off. I’m on my bed, legs splayed, with Mr. Blue kneeling in front of me. Suddenly I feel like I’m at the gynecologist having a pap smear. I relax and enjoy feeling his fingers stroking me, then his tongue. He gets on the bed and then clothes start flying everywhere. He pulls me on top of him and we start having sex. Before long before he flips me over. I’m wetter than I’ve been in a long time.
2:15 a.m. He stops. Just like that. A weird conversation ensues, followed by a biology lesson. He’s clearly freaked out by something but I can’t figure out what. “We’re stopping?” I ask, trying to get to the point and hoping I don’t sound annoyed. He answers yes. WTF? This has never happened to me before. I don’t know how to react. What’s the female version of blue balls? Whatever it is, I surely have it now.
2:30 a.m. I offer to let Mr. Blue stay the night but he gets dressed and flies out of my apartment like a bat out of hell. I stay up, feeling weird. When I can’t sleep, I whip out my Hitachi Magic Wand vibrator and two minutes later, I’m rolling over on my side and a minute after that, I’m fast asleep.


3:15 p.m. I’m still pretty upset about the swift exit of Mr. Blue. I decide that he simply must have come prematurely and was too embarrassed to say so. I feel loads better now. I get to thinking about Mr. Pink. They say the best way to get over someone is to get under someone else. I think this is true.
8 p.m. At work, I log onto to my computer and stay on longer than I should hoping that Mr. Pink, who works at a different branch, will log onto our inter-office IM. He doesn’t.
9 p.m. I run into Mr. Brown, another colleague. He’s been trying to sleep with me for years, and today he asks pointedly when I’m going to let him “tear that ass up.” It seems he finally caught me on the right day! After last night, I’m so frustrated I tell him to come over later. As soon as I say it, I start to have second thoughts, but I don’t renege.
1:18 a.m. Mr. Brown arrives. We sit, chat, and drink some scotch. Well, I drink mine. He lets all the ice melt in his, ruining a perfectly good glass of whiskey.
1:38 a.m. We go to my bedroom. Mr. Brown plays with my breasts. Then we get naked and he spanks me a little. He really likes receiving oral and I really like giving it, so I do for a while. He puts on a condom and I get on top of him. His penis is huge, but he’s so skinny; I must outweigh him by forty or fifty pounds. He’s deceptively strong, though, and tosses me around like a rag doll.
3:30 a.m. With my head hanging off the bed, Mr. Brown stands over me and comes on my breasts, with a little on my chin. After cleaning up, we both settle in for a nap.
5 a.m. Mr. Brown leaves and I sleep like a baby, grateful to finally have had good sex.


7:20 p.m. Again I spend a good chunk of my work day looking for Mr. Pink on interoffice IM, but he doesn’t show.
10 p.m. Mr. Brown passes me in a corridor and we exchange knowing smiles. I tell myself it was a one-time thing. I’m grateful that he’s not acting weird. It looks like no harm is done to our professional relationship or our friendship. It feels like I’ve won a victory.
1:10 a.m. When I get home, I whip out my Hitachi again and think about Mr. Pink the whole time. I come in two minutes flat.


3 p.m. Another late shift. I spend most of it wondering why I haven’t heard from Mr. Pink.
8:33 p.m. Mr. Pink finally logs on. My heart immediately starts beating faster. I curse Mr. Pink for having that effect on me. We haven’t seen each other in a few months. He is maddeningly elusive. I’m starting to suspect that I’m a little bit in love with him. I wait a few minutes to see if he’ll start the conversation.
8:36 p.m. Hey you, I type. Hey baby, he responds. Baby. Stupid, practically meaningless word, but I want to do a backflip when he uses it in reference to me. He asks how my love life is, and I tell him it’s nonexistent. He says he’s bored sexually and it’s frustrating. Then you should come home with me, I type. He says he has plans. Same old story. I roll my eyes at the computer but then he asks me what time I work the next day. I’m off. He says he might have to pay me a visit. I’m wary. We’ve made three sex dates over the past couple of months, all of which he cancelled last minute for stupid and obviously false reasons. Are you serious this time, I type. Yes. Give me directions to your house. I give him very detailed directions and then I don’t hear from him for a few minutes so I assume he’s writing them down. Then: got it … see you in the morning.


10 a.m. I’m excited. And horny. I put on lacy underwear and perfume, but then throw on jeans and a hoodie because I believe in having balance. And then I force myself to sit still. It’s difficult. In my head, I go over all the fun things I want to do to Mr. Pink.
10:30 a.m. I push my brunch date back to 2 p.m.
11 a.m. The air is thick with the sound of my doorbell not ringing. I check my BlackBerry for the umpteenth time. No cancellation text or e-mail. He’s probably just running late.
12 p.m. My doorbell is still not ringing.
12:30 p.m. Again, no doorbell. I check to see if my doorbell has suddenly stopped working.
2 p.m. The doorbell finally rings. But it’s not Mr. Pink. It’s my friend and she’s starving. We bake biscuits from scratch and make scrambled eggs. We drink passion fruit mimosas and then light up a couple of Cohibas. For awhile, I do a very good job of forgetting that Mr. Pink has made a fool of me yet again. What’s worse is that this does not stop me from wanting him at all. If anything, it only makes my desire for him stronger.
5 p.m. My friend leaves and I immediately reach for my Hitachi. I make myself come two times in a row. Still, I’m not satisfied.
9:30 p.m. I text Mr. Brown and tell him to come over for another round. He responds quickly and says he’s on his way.
11:55 p.m. Mr. Brown arrives and he wastes another glass of my good scotch. I make a mental note to never offer him scotch again. He does bring weed, but I don’t feel like getting high. I tell him to feel free to smoke but I won’t be having any. I’m better in bed when I’m sober. He palms my ass for a minute, and that leads to me giving him head again. He likes it very much but I’d really just like to get to the sex part already.
12:55 a.m. Mr. Brown gets on top of me and we start having sex. He stops after exactly four strokes. Then I hear him go “Uh-oh.” He’s looking down and has a troubled look on his face. “You’re getting your period,” he says with disgust. I look down. It’s faint but sure enough, the condom is turning pink. I’d cry if I weren’t so busy laughing. He jumps up. “I’m not freaking out,” he says. But clearly he is freaking out. I take the condom off and discard it. Then I go into the bathroom to take care of my period. When I get back, Mr. Brown is wrapped up in my sheets. I lay next to him and close my eyes, wondering when getting off became so complicated.
1:30 a.m. Mr. Brown starts tugging at me. I know he wants me to suck him off but I really don’t feel like it. I want to take some Motrin and go to sleep. When he realizes I’m not going to give him head, he climbs on top of me, squeezes some lube between my large breasts and presses them together with his penis in the middle. He grinds against me, groaning as if it were the real thing. After some time he actually comes and I can’t help but feel proud at being able to get him off with just my tits. He rolls over and falls asleep.
5:15 a.m. Mr. Brown wakes me up and tells me to call him a cab. I don’t think I’ll be inviting him over again.


10:20 a.m. When I log on at work, I half expect to see some kind of sorry explanation from Mr. Pink but I don’t even get that much. I’m pissed and forbid myself from contacting him ever again.
7 p.m. At my place with work friends. There is a tall, very cute Polish man, who I’ll call Mr. Blonde, a friend of a friend, sitting on my couch. He’s 25 but likes to pretend he’s 29, and I steal glances at him.
8:45 p.m. I learn that Mr. Blonde is on the rebound, like me. I pour Mr. Blonde some scotch and he does not let the ice melt in it. Actually, he drinks it all in one long swig. I like him already.
10:15 p.m. Three of us are sitting around my dining room table smoking the cigars that Mr. Blonde brought over. Mr. Blonde also works for the same company I do, thankfully at a different location.
11:03 p.m. There are only two people left at my place, Mr. Blonde and the friend that brought him. We’re on my couch and her feet are in Mr. Blonde’s lap. My arms are curled around his and my head is on his shoulder. The booze has us all feeling lovey-dovey so I pour some more. Mr. Blonde and I are holding hands. There’s no pressure, no drama, just pure drunken, I’m-on-the-rebound-and-I-need-to-be-held affection.
12:35 a.m. I tell Mr. Blonde and friend that they can stay over if they want. Mr. Blonde asks where he’ll sleep and I tell him he’ll sleep in the bed next to me … and my friend. My bed is big enough for three. Mr. Blonde nestles between us. He spoons me for a couple of minutes and then he spoons her. This doesn’t make me feel weird in the least. I drape my arm over Mr. Blonde’s firm midsection and fall asleep like that. In the morning, I realize that though there was absolutely no sex involved, yet it was the most satisfying encounter I’ve had all week. I seriously contemplate being celibate.

TOTALS: One full act of intercourse; two unfinished acts of intercourse; one spanking; one act of oral sex (receiving); three acts of oral sex (giving); one cancelled sex date; four masturbation sessions; one boob thrusting; one impromptu cuddle party and one bottle of single malt scotch (emptied).

The Woman Sleeping With One Colleague While Pursuing Another