You need to know your place

Q About a month ago, I got drunk and slept with my friend’s
girlfriend. (He’s 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, 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. 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, 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 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 (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 anyone. She is a free and
autonomous individual; her affections are hers to award and hers to
rescind. And as it’s the lady who would be doing the dumping here, FIM,
you wouldn’t be crushing your second-tier friend with a pre-winter
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, that you
look good in the shower, et cetera, but you are only evidence that her
relationship isn’t long for this world, FIM, you are 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 sooner
rather than later—but the relationship was doomed before you
drunkenly banged the (shitfaced) lady.

In other words: You’re just a symptom, FIM, don’t flatter yourself
by imagining 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 makeout sessions while her
fiance watched, and I am 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 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

A Well 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 given you his
hypothetical OK 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—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
hypothetical becoming a reality—a potentially relationship-ending
conversation.

But before you can be honest with the boyfriend, TWAT, you need to
be honest with yourself. Repeat after me: “Honey, remember that couple,
my 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 awhile 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

AA 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 most gay people have straight sex 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.

This article appears in Oct 1-7, 2009.