The subject line says most of it, but let me give you some
background...

About a month ago, me and a long time friend, Jane, started dating.
I'd been pursuing her off and on for years, with mixed results, and
she finally made up her mind. We're college students. Jane's parents
are first generation immigrants who basically taught her, "Never drink
alcohol. Don't date until you're 25 and ready to get married. All
forms of sexuality are sinful." She came to college believing all of
it. Then, half way through freshman year, she suddenly switched from
being a non-drinker to a heavy drinker, but kept it secret from her
parents. The same sort of thing happened with us dating: She's very
affectionate when it's just us and a few close friends, but I'm not
allowed to hold her hand in public for fear that her parents might
find out she's dating. Similarly, with sexuality, she’s been slowly
becoming more comfortable with it, but she has a lot a issues with
feeling guilty about it.

Anyway, one of her close female friends is bisexual, and another (who
I'll call Sally) claims to be "curious". Now Jane has decided that she
herself may also be bisexual. (She's been hinting at it off and on for
years.) In one conversation a week ago, we "joked" about having a
threesome with Sally. Last night she started had a "hypothetical"
conversation about whether it would be a good idea for a couple to
have a threesome with another woman. I suggested that it might work
best if they found someone who neither of them knew, to avoid jealousy
issues. That seemed ok with her. Later on, she wanted to know if,
hypothetically, it would be cheating for a woman (while in a
relationship with a man) to "make out" with another woman. (My
response - YES, IT WOULD)

So my dilemma is, as a male, this whole threesome thing is very
tempting, but it seems very risky. I get along well with Sally, and
she's attractive, so it'd be fun to kiss her, but she's mainly friends
with Jane, and I'm afraid that it might turn into Jane cheating on me.
The alternative would be using some of Jane's other connections to
find someone who neither of us know very well. But that seems risky
too.

**My actual question** : So, I'm pretty sure the wise, intelligent
thing to do would be to turn down the whole threesome concept unless
Jane absolutely insists upon it, but I'm foolish and easily tempted,
so what I'd like is to get your opinion on what the probable
consequences would be of involving a third party in our relationship,
and, if we chose to, what the best way to go about it would be.

Hi Phish!

What a dilemma!  I know more than a few men who would fall all over
themselves to have this "problem", and would be quick to tell you how
dumb you are for not just grabbing the idea and running with it.  My
husband included.

They're idiots.  Yes, my husband too.  Him especially.  ;)

You're absolutely right to be concerned!! A menage a trois is a
complicated thing - not just the "mechanics" of it, but the intimate
interaction of three human beings with all of the emotional baggage
and preconceptions that come with these creatures.  Sure, a threesome
might *sound* terrific, and maybe the imagery is really sensual and
appealing, but are you really ready to bring a third into your
relationship, with all of the potential for emotional fallout that
entails?

Pull up a piece of cyberspace, and let's figure this out.  I'm going
to tackle this from the personal perspective, and give you a list of
articles dealing with the subject at the end, OK?  Good.

In any healthy relationship, it isn't what society wants, or what a
partner's parents want, or what *anyone* outside the couple wants that
matters.  It's what the *two of you want* and are comfortable with.  I
don't think I can stress this enough!  Before you even *think* about
adding a third person to your relationship - *even if it's only once!*
- it's vitally important that the two of you are comfortable and
secure in *your own* relationship first.  If the two of you don't have
a rock-solid bond and perfect trust, the results of bringing a third
party in can be devastating - jealousy, broken trust, suspicion,
anger, resentment, fear of sexually transmitted diseases, fear of
ultimate betrayal (one partner leaving the other for the third)...

Phish, I've looked at the information you've given, and I really think
that (right now) giving a threesome a shot is a bad idea.  You have
other, bigger piscine life forms to fry first.

First, you and Jane need to discuss your relationship.  You need to
have The Big Talk.  You know the one - where you stand now, how you
feel about each other, where you think your relationship is headed,
where you *want* your relationship to go.  You're obviously worried
that you're going to lose Jane, and Jane is clearly not comfortable
with your relationship yet.

What?  You burn the sheets up just fine, so of course she's
comfortable?  Uh-uh.  She's not.  I warned you I'd look at this from
personal perspective!  I used to be a conservative Christian, and like
Jane, wouldn't hold my boyfriend's hand in public for fear it would
upset people (though in my case, it was fellow parishoners and God,
not my family, that I worried about).  That was a long time ago - I'm
a liberal pagan now, but still remember what it was like to be afraid
to acknowledge a relationship publicly.  It's *hard* and *scary* to
try break away from ingrained guilt and conservative values,
especially if you suspect that your sexuality might be considered
"alternative".

So talk.  Talk the night away, talk until your lips fall off, then
talk some more.  It's incredibly important that you're both on the
same page when it comes to what you want from your relationship. 
You'll both need to come to terms with her possible bi-sexuality and
discuss how you're going to handle that, and lay ground rules for your
relationship.  Are you worried that she'll eventually leave you for a
woman?  It sounds like you are, so *talk* to her about it.

Next, be patient.  Don't rush things.  Take your time *together* and
explore what you *both* find pleasing.  Let *Jane* bring up the topic
of a threesome, and don't push her.  She may be all talk, just wanting
to express a fantasy - obviously one you have as well.  Fantasizing
together is healthy and helps you both explore the sexual side of your
relationship.  The more comfortable you both are, the more secure you
are in your relationship, the more likely you'll each be to want to
explore your fantasies together.

Keep in mind that most threesome fantasies never get past the
"hypothetical" phase.  (Sorry!)

So what if Jane *does* insist on it?  This is where things get tricky.

You say that if Jane makes out with another woman while she's involved
with you, that's "cheating".  But if she makes out with another woman
while you're in the room, it's OK?  Or do your expectations of a
threesome only include both women pleasuring you, but not each other?

Most men don't think about this aspect (hence the "I wish *I* had that
kind of dilemma!" reaction).  But y'all should.  A threesome isn't all
about the boy, it's all about *all three* of you!  If you're looking
at it with the "WhooHoo!  Me and two hot babes!  YeeHa!" goggles on,
you might be in for a horribly rude and emotionally painful awakening
the morning after.  If you think that they should cater only to you,
and not touch each other, drop this idea now.  It doesn't work that
way, and you'll only have two angry women and a truckload of regret
when it's all done.

(Seriously.  If you don't share well, Just Don't Go There.)

Likewise, if Jane isn't thoroughly pleased with the idea of you
kissing (among other things) another woman, is she going to be OK with
it as long as she's in the room?  Or are her expectations of the
experience that you and Sally enjoy her, but not each other?  (Again,
it's all about *all three* of you!)

And then there's Sally.  What about Sally?  What does *she* expect
from it?  Is she going to be selfish and expect that you and Jane pay
attention only to her desires and not each other, or is she all about
sharing the love?

Truth be told, most humans are very sexually selfish.  They want every
encounter to be all about them and their desires and *maybe* their
partner's desires. It doesn't take much to make someone feel insecure,
inadequate or unloved, and coping with these feelings is hard enough
in a twosome.  Now think about how hard it is with three!

Are your feelings going to be hurt if Jane and Sally really dig each
other and abandon you for a few minutes to enjoy each other?  Is Jane
going to be angry if she thinks that Sally is paying more attention to
you than to her?  Are both girls going to want to go Lorena on you if
you decide that you don't want them to enjoy each other, but only
focus on you?  What about STDs?  Have you all been tested?  What sort
of protection do you intend to use?  And who's responsible for
purchasing the condoms, lube and dental dams?

Sounds tangled, doesn't it?  It should.  It is.  If you both agree to
go ahead with this (after your own relationship is solid), you and
Jane need to sit down again and discuss ALL of this.  In DETAIL.  Once
you've got all of this straight between you, continue on:

-- How do you choose who to invite?  Are you really going to be
comfortable with someone you don't really know?  Ask yourself and
answer honestly - are you willing to let a stranger see you at your
most vulnerable?  Most people aren't, so you should stick with someone
you not only both find attractive and desireable, but also someone you
both trust.  Once you've decided, there is the small matter of finding
out if she's willing.  Once you find her and plan the encounter (you
should allow time to get comfortable with each other), there's a whole
lot more talking to do:

-- Who is bringing what protection?  Lube?  Toys, if that's your
preference?  If any of you does not want to use protection, Don't Go
There.  Call it off.  You owe it to yourselves to be safe.

-- What's going to happen?  In detail.  Who is going to touch whom
where and for how long?  With what?  And what's the third person doing
in the meantime?  While you should definitely have some say in the
matter, it's important that you let the ladies work things out between
themselves as to what is acceptable and what isn't. Boundaries should
be absolutely understood and respected.

-- What if one of you changes your mind?  What if you decide that you
don't want a threesome after all?  Do you leave Jane and Sally alone
to finish?  If Jane feels she's in over her head, does she leave you
and Sally alone?  Or does everything stop, and you send Sally on her
way?  If you walk away and leave Jane and Sally to their own devices,
are you going to be angry, jealous and resentful about it later?  What
if Jane is the one who changes her mind?  If things don't work out, is
Sally going to feel guilty?

-- What's going to happen after?  Will you continue to include your
third, or is this a one time only thing?  Is it OK for either of you
to...play...with your third when the other partner isn't present?  Or
are you going to try to maintain a "just friends" relationship with
the third?

Trust me, if this can't be decided upon peacefully *before* the
clothes come off, it certainly won't happen peacefully *after* they
do, and *nobody* is going to be happy.

-- After your tryst, leave the ladies to talk it over together, alone.
 Then you and Jane need to talk together, alone.  Was it interesting?
Was it enjoyable? Would you like to repeat it?  Don't put off
discussing it - you may find yourselves engaged in a screaming match
instead.

Ooh, this probably sounds like a lot of work, doesn't it?  It *is* a
lot of work - you're dealing with the dynamic of a relationship, and
that dynamic being changed by a third person involved in your most
intimate interactions.  Keeping all of the pieces in place is hard
work.  If you both can handle the effect it will have on your
relationship, terrific!  Have a wonderful time!

If either of you feels that you can't manage that, a threesome is not
for you:

"If you don't feel secure and/or sure, the best advice is: don't do
it."

Menage a troi
[ link omitted due to explicit content on the pages ]

Before you think any more about the subject, perhaps you should engage
in a bit of reading:

"Ask Dr. Tracy" 10/24/99 Advice Column
http://www.loveadvice.com/Columns/COL_2799.HTM

My Man Wants a Threesome
http://magazines.ivillage.com/cosmopolitan/experts/agony/qas/0,,413027_329789,00.html

Requestline
http://www.requestline.com/archive/nov98/cruz/botleft.html

Go Ask Alice: Menage a trois?
http://www.goaskalice.columbia.edu/2184.html

Ask the Fat Broad:  So You Say You Wanna Have Two Girlfriends?
http://www.scarletletters.com/current/atfb_threequest.shtml

Is Threesome Cheating?
http://www.ivillagehealth.com/experts/emotional/qas/0,,242102_1308,00.html

Are Threesomes Healthy
http://www.virtualvoyage.com/soapbox/client2/sep93.htm

he wants a threesome
http://www.askmen.com/love/drzimmer/58_love_answers.html

Good luck!

--Missy

You can find lots of information - some sources more explicit than
others - by searching on [ "menage a trois" advice ] and [ threesome
advice ]

All our friends are to be valued and we like them despite their faults.

First, let me say you got an answer that was worth way more than you
paid for it.  It was well researched, well written, and most
importantly, right.  The only critique I would have is that it was not
strong enough.  So, with that in mind, let me sum up my comment:

DON'T!!!

Now for the long version...  I'm a guy who has the same fantasies
about a threesome as every other guy.  Lesbianism is a huge turn-on
for me.  So, here's a guy's point of view (albeit a slightly older
viewpoint).  You are very wise for your age in that you recognize what
the right answer is, and that you understand your own humanity.

Now, if your girlfriend has issues with holding hands in public, the
idea of a threesome is way, way off in the future for you.  You both
need to get to the point where sexuality and the many variations of it
(mainstream and otherwise) are not something to be whispered about. 
When you can openly, in public, discuss topics like your favorite
sexual positions, or when you can talk to both your parents about how
often you should try to conceive without blushing, then maybe you can
consider this.  If you have issues with "cheating" you're definitely
not ready for this.

There is a mildly amusing and somewhat superficial movie about this
subject called "The Sex Monster" with (iirc) Mariel Hemmingway.  Might
be worth renting.

Consider this -- what if your girlfriend comes to you and says, "I
really want to have a threesome!"  You respond "Yeah!" and she says
"Great!  I met this really cute guy named Ted who is really sweet and
intelligent, and I'd love to watch you two together!"  Ready for that?
 If not, you're not looking at all this correctly.  Are you even ready
to see her being pleasured by another man?  Is that what you had in
mind?  Rent a movie called "Unfaithfully Yours" with Dudley Moore. 
Pay attention to the difference between what he envisions in his head
and what really happens.  Missy is quite right in that the way it
works out is not what you or I might fantasize about.

Our society is really rather screwed up when it comes to sex, ranging
from the extreme taboos (like your girlfriend grew up with) to the
extreme embracing of sex (as in the 70's and on the internet).  This
means that there is always more to it -- there are very few for whom
sex is just an enjoyable pasttime, the same as rock climbing or seeing
a movie.  Would you be upset if your girlfriend went to see a movie
with someone else?  Would she be upset if you did?  Same as if you
slept with someone else?  There's a difference there.  Until there
isn't, this is not a simple subject.

This means that the social implications are huge.  What if someone
talks and all your friends find out about your threesome?  What about
coworkers?  What happens when your parents find out?  (They will,
trust me.)  Are you prepared to accept the fact that people you care
about may no longer be interested in associating with you?  Are you
ready to have your friends ask you when they can have a shot at your
girlfriend?  (In many people's minds, any non-standard sexual activity
either makes you an outcast or makes you easy.)

Consider this:  Having a child is a huge strain on a relationship --
the staying up all night, getting vomitted on, having to go to the
park instead of a concert, watching Sesame Street instead of South
Park, etc.  It's even more of a strain when the child has health
problems.  There's the added stress of worrying about the kid,
spending nights in the emergency room, medical bills, etc.  Any
relationship is like having a regular kid -- you have arguments,
disagree about things, but you work it out, mostly.  Adding any sort
of non-mainstream activity puts that much more stress into the
equation.  (This is true whether its something like a threesome, or
owning a 40-year old Land Rover, or collecting Donald Duck stuff, or
whatever.)  You want to minimize the strain on your relationship
whereever possible.  Unless a threesome is truly important to you,
it's not worth the problems.  (And it probably won't be as good as you
think anyway.)

So, again, to summarize, DON'T!!!

Talk about it, fantasize about it, play games between the two of you. 
Talk about sexuality, your fantasies, what turns you on and off. 
Consider all extremes such as bondage, domination, homosexuality (for
you as well as her), and when you can consider these without any
qualms, without giggling or being grossed out, then maybe you are
ready to begin experimenting with such things.  You may decide you're
both not interested in some of these, but if you can't consider all of
them, you shouldn't consider any of them.  Check out a TV and Radio
show called "Talk Sex with Sue" (or the prior version, the "Sunday
Night Sex Show").  There's a website for the new one at
talksexwithsue.com (iirc).  Sue Johannsen(sp?) has been a sex educator
for probably as long as your parents have been alive.  She discusses
pretty much anything sexual the same way most women her age talk about
quilting or baking.  When you can be as open as she is, you may be
ready.  Don't worry, there's plenty of time.

One more comment -- your girlfriend may simply be bi-curious because
she has not been exposed to it previously, or she may actually be
homosexual and just didn't know it (or never considered it as a
possibility.)  If she really is gay, better to find out sooner than
later -- you don't want to get married, have a kid, buy a house, and
have her leave you for another woman.  Talk about it, and if she is
truly interested in exploring it, suggest she gets counselling to help
her find out what she wants and to deal with it in the context of her
background.

Anyway, good luck, and congratulations on having the wisdom at such a
tender age to see that this may not be a good idea!  Your girlfriend
is truly lucky!