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.
