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 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
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).
“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 would be doing the dumping here, FIM, you wouldn’t be
crushing your second-tier friend with a pre-winter breakup,
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, 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.
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 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?
With A Third
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, 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 hypothetical becoming
a reality—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 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?
Rear Entry Weekly
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.
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