She's Not a Come Sock 

Breaking up a relationship, helping another, and explaining heterosexual anal penetration.

A month ago I got drunk and slept with my friend's girlfriend. We both swore never to tell anyone. Only problem is, we've been hanging out a lot lately and sending private messages to each other multiple times a day. 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 is 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 are really into each other, but there are issues. For starters, she would 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. I'm wondering if there is 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 pre-winter breakup.

Fucked In Madison

As "the lady" is not a wallet, a car, or a crusty old come sock; 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 rescind. And as it's the lady who would be doing the dumping here, you wouldn't be crushing your friend with a pre-winter breakup, she would. Let's not overestimate your importance in the little lady's drama. I'm sure you're a lovely person, great fuck, etc., but you are only evidence that her relationship isn't long for this world, not the reason it isn't. Your appearance on the scene may have given her an incentive to end a relationship that needed to end, but the relationship was doomed before you drunkenly banged the lady.

That said, her friends and future ex-boyfriend may very well blame you when the breakup comes. The only way to avoid looking culpable 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.

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 fiancé watched, and I am 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 hypothetical situations like this to be "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

Well aren't you the selfless little people-pleaser, TWAT. You're willing to sleep with this couple even though you're only "somewhat turned on by the idea." But if you "did this for [your] friends" 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 — 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 given you his hypothetical okay to get with your friends, 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 a potentially relationship-ending conversation.

But before you can be honest with the boyfriend, TWAT, you're going to need to be honest with yourself. 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?"

I'm a GGG thirty-year-old straight male who was pleased with your response 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

No homo, DREW.

Once again: If a man and a woman are doing it — whatever it is — it's a heterosexual sex act. If a girl is doing it with/to a boy, it's heterosexual sex. But the relevant question 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.

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