sex diaries

The Architect With Multiple Secret Boyfriends

Photo-Illustration: James Gallagher

This week, a woman who can’t stop cheating on her boyfriend, even though she isn’t even getting off on it: straight, in a relationship, New York, 39.


8:00 a.m. I always wake up at the same time every morning. But my 28-year-old live-in boyfriend always sleeps in until 10 or 11 a.m., so I try to go back to sleep. I stay in bed in the hopes of morning sex.

10:00 a.m. He wakes up and we have some hot, albeit brief sex, doggy style. We’ve been together for 3 years. He doesn’t like morning sex usually; he hates bad breath and that I’m “not clean.” That makes me feel undesirable, and like I need to be perfect any time we have sex — shaved, showered, decked out in lingerie. We haven’t had sex for a few days, so that’s the only reason he goes for it today. He finishes, I don’t. I almost never do — I’m too neurotic. I’ve always had this problem. I come with a vibrator, or if a partner massages and kisses me while I use it. I masturbate a lot.

4:00 p.m. I’m an architect. I work from home a lot, so my schedule is flexible. I like to take weekends to relax and get recharged for the week. I spend my day reading, hit the gym, and go to the park for a few hours.

11:00 p.m. My secret boyfriend texts me. He’s in town for work. We’ve been carrying on an affair for the last six months even though we’re both in long-term relationships and we live thousands of miles apart. “I just landed. Come sit on my face.” It’s too late — even though my boyfriend isn’t home from work yet, he’ll wonder where I’ve gone this late on a Sunday. I tell secret BF we can meet up tomorrow.

We had an Instagram flirtation for a months and finally met at a conference where he was a keynote speaker. It was an instant attraction. We slept together the day we met. There’s something about him … He’s the bad boy, everything my boyfriend isn’t. He’s also older and more established in his career, at the top of his game, which is insanely sexy to me. As far as my primary boyfriend knows, we are monogamous, so it’s all very sinister.


8:00 a.m. Secret BF texts that he wants to meet up for lunch. His meetings are close to my apartment, and he desperately wants to fuck me in my bed and “claim” his territory. Although I’m a total deviant for carrying on an affair and lying to my boyfriend, with a man who has a girlfriend no less, this is a line I will not cross.

11:00 a.m. I head to a nearby coffee shop to get some work done. Secret BF texts and says he’s ready for lunch: He’s hungry, so he either needs to eat food or my pussy. I suggest a restaurant nearby.

12:00 p.m. We meet for lunch. He makes me so nervous, and I’m not easily intimidated by people. Generally I’m dominant and confident, but with him, I turn to putty. He’s a celebrity in our industry. I watch him eat a bowl of ramen. After he finishes, in the most cavalier way, he says, “bathroom?” He goes first, and I follow, knocking twice. We fuck in the bathroom of the restaurant, but since it’s been months since we’ve last seen each other, it doesn’t last long. He comes in my mouth. I don’t finish.

2:00 p.m. I head back to the coffee shop to do some more work. My mind is racing with mixed emotions. I hate that I’m a cheater but I can’t walk away from the thrill. I also cheated on my ex-husband, but for different reasons — he was super abusive so it was justified in my head. This time, my relationship is stable to a fault.

6:00 p.m. I head home to spend the night with my boyfriend. He has no idea about the cheating, and it kills me that I can do this to him. I read an article by Dan Savage that says you should do what you need to in order to save a mostly happy relationship, even if that means cheating. I don’t know that I entirely agree, but it appeases my guilt somewhat.

10:00 p.m. BDSM guy DMs me on Instagram. He’s a guy I met recently at a wine bar who immediately picked up on my kinky side — I mentioned something about ball gags in my drunken stupor. He’s been in my DMs every day since. I’ve dabbled as an amateur dominatrix for as long as I can remember. I’ve never once had to advertise: These men always pick up on the energy I put out. I do it mostly for fun, but it has its financial perks, too. Sometimes men will give me cash just for meeting me, to set the tone of the relationship. If it’s $500 for a 20-minute coffee, then I’ll know they’re serious. Sometimes it’s gifts — a pair of Louboutins, or I’ll bring them out as my slave for the night and they’ll have to pay for everything. My boyfriend knows about this side of me — he likes the money it brings in. At least it’s one thing I can be honest with him about.  


8:00 a.m. I wake up to get ready to start my day. I put more effort than usual into my appearance with the hopes that I’ll see secret BF again. We text a little, but he doesn’t suggest meeting up today. I’m disappointed, but know that I’ll see him tomorrow, since we made plans to hang out for his last night in town.

4:00 p.m. I head home and am so happy to see my boyfriend. He’s unbelievably sweet, and  only seems to be getting hotter by the year. I wonder why he isn’t enough for me. Why do I have to be such a terrible person and go behind his back? I’ve tried to suggest an open relationship, but he won’t budge — he wants monogamy for the most part. We’ve had a few threesomes here and there, but that was years ago, and our sex life now feels stale and predictable. I guess that’s what happens after you’ve been with someone for a while.

10:00 p.m. My virtual boyfriend from London texts me, checking in. We met on a swingers website over ten years ago, but we’ve never met in person. He’s a super successful chef, and we have an incredible bond. It’s definitely an emotional affair. Where secret BF meets my depraved, raunchy, kinky side, virtual boyfriend meets my emotional needs. We talk on the phone often, and it feels so good. He makes me feel safe, accepted, and loved.


8:00 a.m. I wake up knowing I’m going to see secret BF today. I’m excited.

12:00 p.m. I spend the morning finishing up some work, but most of it is devoted to primping, ensuring that I look hot as fuck. We’ve planned to meet on a rooftop for drinks nearby, but we only have a few hours because he has another dinner later. It bothers me that he can’t spend the entire night with me, but I know he’s here trying to fit in as many meetings as he can, so I take what I can get.

4:00 p.m. We meet up and I can tell he’s turned on just by looking at me. He makes a comment about my outfit. He thinks the way I dress is unusual — I wear a lot of men’s clothing, vintage fur, loud prints, and oversize shirts — but I know it drives him wild. We spend three hours drinking wine, talking, and stealthily meeting in the bathroom to fuck, twice. After the second fuck he finally starts to open up. He tells me that he’s planning to propose to his girlfriend. He says he’s never had what we have with anyone else. His soon-to-be fiancée is kind, but their sex life is unfulfilling. I know I’m developing strong feelings for him, but what can we do? Random meet-ups in random cities is the best we’ve got. It gives me something to look forward to.

9:00 p.m. I go home and shower. I don’t want the smell of him on me or my boyfriend might suspect something. It concerns me how good I’ve become at lying.


9:00 a.m. I find out about a work event I know I should attend; secret BF will be there but I don’t tell him. I don’t want him to think I’m coming just so I can see him, even though that’s  definitely an added bonus, since I know he’s leaving today. I wear a fire outfit, knowing I look effortlessly stunning.

3:00 p.m. I run into secret BF and I can tell he’s excited to see me. He comes over and gives me a hug. We exchange a few pleasantries and chat for awhile. He excuses himself to head to the airport. I know he’ll text me as soon as he leaves the building; and he does. He tells me my outfit is hilarious, and that he’ll miss me. I tell him we should have fucked in the bathroom, and he laughs.

5:00 p.m. I head to a meeting and then call it a day. I decide to walk home even though it’ll take me over an hour. I need to clear my head. My boyfriend is gone for the weekend, headed to cottage country with  his university bros. He’ll be drunk all weekend and incommunicado.


9:00 a.m. I wake up feeling like I’m coming down with something, but insanely horny. My boyfriend is somewhere on a lake with his friends, so I leave him alone. He wouldn’t respond anyway. Secret BF always goes incommunicado for days after we see each other so I decide not to text him, either. Instead, I reach out to my hot 20-year-old French man whom I have virtual sex with now and then. We met on Instagram. Well, we’ve never “met,” we’re just online fuck buddies. We exchange photos and videos; he talks dirty to me in French and it always sends me over the edge. Funny, it’s the only time I have an orgasm this entire week, despite being fucked repeatedly. He’s super hot, and I love that he finds me so sexy even though I’m much older than him.

5:00 p.m. I’ve developed a full-on cold, so I spend all day in bed. I don’t hear from secret BF.


10:00 a.m. Secret BF hasn’t texted in days and I’m getting annoyed. This is what always happens. We spend time together, have incredibly hot sex, and then he goes MIA. It drives me nuts, and every time it happens, I swear to myself that I’m going to end it, and channel my energy into improving my own relationship — you know, spice it up, maybe go to a swingers club, find another couple to fuck. Anything.

12:00 p.m. Like clockwork, after two days of no communication, he texts me. “Hey, I’m engaged.” I respond, “Funny, and you thought to yourself, hey, I should let the woman I’m fucking on the side know.” We have the same conversation we always do: He doesn’t want to complicate things, he doesn’t want heartbreak, he just wants something fun and sexy — the things we can’t get from our partners. I’m getting tired of this back-and-forth. I let him know that I’m not an emotional robot, and I can’t pretend I don’t feel something for him. He admits that he feels something for me too, but that he’s marrying someone else. Fuck! Why do I always self-sabotage with these toxic men who I know are bad for me?

5:00 p.m. My boyfriend comes home from his cottage weekend. He’s hungover as fuck, but damn he’s looking sexy. I’m so happy to see him. We spend the night together and I take in his smell, cuddling him, kissing him, loving him. I know how lucky I am. Why am I doing everything I can to sabotage it?

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The Architect With Multiple Secret Boyfriends