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 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...
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...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).
Fucked In Madison
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 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, 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 ppearance 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?
Toying With A Third
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 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—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?
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. 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
When I fucked girls, I secretly
pretended they were boys. So worry about what’s going on in
your head, DREW, and not what’s going on in your ass.