Q About a month ago, I got drunk and slept with my friend’s girlfriend. (He’s not my best friend, more of a second-tier friend.) We both swore never to tell anyone and left it at that. Only problem is, we’ve been hanging out a lot lately and sending private messages to each other multiple times a day, but nothing physical. It’s progressed to the point that our mutual friends are starting to notice that there’s something going on between the lady and me. And frankly, if someone I was dating were doing what she’s doing, I’d consider it cheating.
Things came to a head a few nights ago when we ended up skinny-dipping and then showering together. We are obviously infatuated. We had a long talk about what to do: we’re really into each other, but there are issues. For starters, she’d have to break up with her boyfriend, something she would do in theory, but there are housing issues (she lives with him) and friendship issues (her best friend is his best friend’s lady). Furthermore, I’m scared not only of getting beat to hell by her man but of getting shunned by all of my friends for stealing another man’s girl.
Everything is interconnected in the most fucked-up ways possible. I’m wondering if there’s any way out of this with the desired result for everyone: the lady and I together, friends understanding of the situation, and her boyfriend not totally destroyed. I still like her boyfriend as a friend and a guy, and I don’t want to crush him with a prewinter breakup (it gets real lonely here in the winter). —Fucked in Madison
A As “the lady” is not a wallet, a car, or a crusty old come sock, FIM, you can’t “steal her” from a second-tier friend or anyone else. She is a free and autonomous individual; her affections are hers to award and hers to rescind. And as it’s the lady who’d be doing the dumping here, FIM, you wouldn’t be crushing your second-tier friend with a prewinter breakup, she would.
Let’s not overestimate your importance in the little lady’s drama, FIM. I’m sure you’re a lovely person, you’re a great fuck, and that you look good in the shower, etc, but you are only evidence that her relationship isn’t long for this world, FIM, not the reason it isn’t. This breakup was in the cards before you and that fateful drunken night. Your appearance on the scene may have given her an incentive to end a relationship that needed to end—and end it sooner rather than later—but the relationship was doomed before you drunkenly banged the lady.
In other words: you’re just a symptom, FIM. Don’t flatter yourself by imagining that you’re the disease.
That said, FIM, her friends and future ex-boyfriend may very well blame you when the breakup comes. The only way to avoid looking bad/culpable/responsible in their eyes—and get the girl without the beating—is to inform the lady that you’re into her and want to be with her, but that you can’t see her until she’s free and clear. No more hanging out, no more texting, no more skinny-dipping, no more showering together until she’s officially single and available.
Q Two of my closest friends, a straight couple, recently got engaged. As an engagement present, my female friend would like to include me in their sex life, potentially for just one evening or perhaps for longer. She and I have had a few make-out sessions while her fiance watched, and I’m somewhat turned on by the idea of taking our escapades further. But there’s a catch: I’m currently seeing someone who says he doesn’t consider fantasizing about this “cheating” but would probably be uncomfortable if I actually did this for my friends. Should I tell my friends I can’t go any further out of respect for his feelings, or tell him that the situation is no longer hypothetical and risk making him uncomfortable, or help my friends out on the condition that it only happens once and not tell him at all? —Toying With a Third
AWell, aren’t you the selfless little people pleaser, TWAT. You’re willing to sleep with this couple—maybe once, maybe weekly—even though you’re only “somewhat turned on by the idea.” But if you “did this for [your] friends”—if you condescended to help them out—what do you tell the man you’re currently seeing? You could tell him the truth, of course, which would be the right thing, the responsible thing, the ethical thing—but that might make him uncomfortable, poor dear. So you hesitate. Oh, not out of selfish desire to avoid an awkward conversation, of course, just out of an overabundance of concern for his feelings.
Sorry, TWAT: since your boyfriend has already told you that he’s not comfortable with your having a threesome, there’s no way to justify making an engagement present of yourself without informing him in advance. And let’s be honest, shall we? Your reluctance to inform the boyfriend isn’t about a selfless desire to spare his feelings, but your cowardly desire to avoid an awkward conversation and—if he balks at this—a potentially relationship-ending conversation.
Once you’re honest with yourself, TWAT, you can be honest with the boyfriend. Repeat after me: “Honey, remember that couple, my insanely hot friends? They’ve asked me to have a three-way with them, and I want to so bad my ovaries are throbbing—that cool with you?”
Q I’m a GGG 30-year-old straight male who was quite pleased with your response a while back to a woman who asked if her husband was gay since he enjoyed some stereotypically gay things. You told her that enjoying “gay” things doesn’t make a person gay. If a guy likes to get fucked in the ass by a dude, then he might be gay, you said. I’ve never been attracted to men, but I have always been ridiculed by friends and girlfriends for liking “gay” things, so much so that I began to wonder if I might be gay. Reading your advice was just the confidence boost I needed.
But then I let a girlfriend “experiment” on my ass. What started out as a kink with her finger has turned into a full-blown fetish with her dildo (non-penis-shaped). I wondered if this might be a sign, so I tried masturbating to some gay porn. Not for me. I still don’t have any desire to be with a man sexually, Dan, but I love having my ass pounded. Does that tip the scales toward homo? —Doing Rear Entry Weekly
A No homo, DREW. Once again: if a man and a woman are doing it—whatever it is—it’s a heterosexual sex act. It doesn’t matter who’s on top, who’s wearing the lingerie, who’s being penetrated, or whether the dildo is penis-shaped or Glenn Beck–shaped. If a girl is doing it with/to a boy, it’s heterosexual sex. Gay people can have heterosexual sex, of course, and plenty of gay people do before coming out. (Gay guys have straight sex in high school like straight guys have gay sex in prison: under duress.)
But the relevant question, DREW, isn’t “How gay is this ass-fucking experiment?” but “What’s going through my mind during this ass-fucking experiment?”
When I fucked girls, I secretly wished/pretended they were boys. So worry about what’s going on in your head, DREW, and not what’s going on in your ass.