Advice on telling someone

[Spades88]

Hey all, first post here (Though, have been visiting the forums regularly for quite a while now), and have had a dilemma as of late which caused me to seek advice, since the community here always seemed very welcoming and helpful I'm also not entirely sure if this would be the correct place to post this, but it seemed the most suitable, so apologies in advance if I'm wrong!

Anyway. I suppose some backstory would help! I'm a younger guy (early 20s), I'm heterosexual (Though, I've always seen sexual orientation to be more of a scale than a few definitive choices...) and have had a... bit of a thing for crossdressing for quite a while now! Not sure how it started, I'll be honest, I don't really remember, though I'm pretty sure it started with high heels
It has always been a strictly private thing for me. As of late, it's been becoming a bit more public (I'd very occasionally wear tights underneath clothes - particularly if I have no clean socks ), and have actually been out fully dressed in the early hours of the morning... When it's dark, and no one's out. Other than that, I've never had any intention to take it public at all. For me, crossdressing is about comfort. I find the clothes to be oddly comfortable, and much more fun to wear and experiment with than male clothing. That's not to say I don't get any... Arousal? From wearing them, but that's not the primary reason for me, I suppose.

I've also got a close friend (I've known him for over 10 years), that I'm unsure of his sexual orientation, though he's said before that he has found me attractive, despite knowing that I'm not into guys. He's also previously stated that he's into "shemales" (... I don't know what the accepted term is to be honest, so I'm simply going to quote him. Please don't take offence if the term is in any way offensive).
Before I proceed I should probably clear up that I understand that there's a difference between a crossdresser and a "shemale", or at least, I'd consider there to be one (I'd describe myself as a closet crossdresser, though not a closet shemale).

Now, my question is, does anyone have any thoughts as to whether experimenting together would be a bad idea, considering that we're close friends and that he's likely interested in me (though this would be purely experimental and fun, hopefully, as opposed to a relationship type deal)?
And if anyone has been in a similar-ish situation to this and it worked out, would you possibly have any advice on how to go about raising the idea?

Thanks!
I realise I tend to ramble when on forums. I don't know how, I think I construct my sentences in a very long winded fashion, and probably go into details that aren't particularly important

[bound_jenny]

I think your main concern should be the effect, on the medium to long term, this would have on your friendship. In the case that your friend would accept your "coming out", and accept some kind of interaction, would he be satisfied with just the "experimental and fun" aspect, or would he want to go further into a "relationship type deal"? Am I correct in assuming that you resist the latter in favor of the former? If so, how would your friend react to you politely declining a deeper relationship?

That's where it gets really, really complicated - everyone is different and it's extremely difficult to predict how they will react in a given situation. Your friend might graciously accept your limits, or be offended and you may lose him as a friend.

I would say start by admitting your crossdressing activities, in the proper context, of course (not just blurting it out spontaneously when talking about the ball game), and leaving it at that for the moment. Let the information sink in, and if he's interested in anything else, let him be the one to step forward (you have already done such a step by admitting you crossdress, so let him take one on his own) - but don't provoke it, let it come by itself. Anything forced is likely to fail miserably.

Basically, be careful.

And don't worry about rambling. Going into details helps people understand better with more information to process. I won't complain - I can be quite the blabbermouth myself (post count submitted as evidence ).

Jenny.

[lj]

If the friend has already indicated he finds the OP attractive, and has confessed a liking for she-males, then the OP shouldn't expect a bad reaction to "outing" his own cross-dressing. As Jenny says, there's a time and place, but it shouldn't be hard to find the opportunity.

If the friend hasn't indicated a clear sexuality, there is a need to be a bit cautious jumping to conclusions. Quite a few people find a member of the same sex attractive in some way but have no sexual interest in them. However, the interest in "she-males" does suggest a willingness to have a more than a purely friendship-based relationship with a man, although there may be no desire to actually develop one. I can speak from a bit of personal experience.

I used to cross-dress, particularly at play-parties, and became friends with a male Dom and his transgendered (M to F ) partner. Judging by his various photos on FetLife etc it is clear he has a preference for Cross-dressers/TV/TG. I had several play sessions with him and his partner, mainly electro-play, which was his speciality and something I was interested in experiencing. There was never any sexual contact, I had made that clear before we played, and he never behaved in any way incorrectly, so it was a good experience all round. So there's no reason, on that basis, that the OP and his friend cannot set up a similar agreement. That is all down to negotiation and consent.

On the subject of definition, again speaking from experience, a cross-dresser can be entirely hetero-sexual, homosexual or any shade in between. My understanding of the term "she-male" is a man who wants to play the role of a female as closely as possible, but without being transgendered - which I understand to be a psychological condition - no, not crazy !!!! but finding their mental perception of themselves not fitting into the physical body - rather than a chosen role to play. If anyone else would like to improve or add to that, please do.

[ponylady]

guess my mod-colleges said it all.

only have to add: after you have thought about at length go with your feeling; it's usually correct.

[Spades88]

Jenny pretty much hit the nail on the head as far as my concerns go. My main worry is that, should he "accept", then in the future our friendship be compromised by what happened, if for whatever reason the situation have to end. Though this extends further to the point at which I worry that, while he may not be bothered initially by the absence of intent for a deeper relationship on my part, and accept anyway, that he may in the future grow to change his mind.
Oddly enough (for me, at least... I tend to be quite a sceptical person) privacy isn't a concern for me - I trust him to respect privacy with regards to what I tell him/what happens.

I, for the most part, have planned out how to approach it - my rules, so to speak, as well as how to raise it in conversation (it's unlikely it'll just pop up - it would have to be out of the blue, yet obviously not at a time which it would seem completely inappropriate).

As lj has said, I shouldn't jump to conclusions regarding any sexual interest - I have no definitive proof, though there is certainly sufficient evidence to cause reasonable suspicion - I've even had other, more distant friends tell me they believe him to be interested. Though maybe the inclusion of this is somewhat irrelevant

Ultimately, I know he's quite an easy going, rational person. If, as Jenny stated, I had to politely decline a deeper relationship, I don't expect it would offend him. I don't believe it to be within his character to be offended by such a thing (particularly since, in the past, I've had to do something somewhat along the same lines).

I may be making a big fuss, as it seems this whole reply was my way of saying I should go for it, though it being the first time I bring it up remotely publicly, combined with fear that it may ruin a close friendship, is making it hard for me to accept any of my own arguments

[bound_jenny]

When you express your thoughts like that to someone else (even if it's us pervs... ), it forces you to formalize your thoughts and make them coherent enough for people to understand what you're explaining - so you're basically making yourself understand what you're feeling just as much as - or more than - the people you're expressing yourself to. It makes you sort things out in your head.

That's in contrast to the unholy mess in my brain...

Jenny.

[lj]

That's in contrast to the unholy mess in my brain...

Jenny.

you just need a good whipping

[bound_jenny]

That's in contrast to the unholy mess in my brain...

Jenny.

you just need a good whipping

You forget that I'm the one holding the whip...

Jenny.

[CheerfullyInsane]

When you express your thoughts like that to someone else (even if it's us pervs... ), it forces you to formalize your thoughts and make them coherent enough for people to understand what you're explaining - so you're basically making yourself understand what you're feeling just as much as - or more than - the people you're expressing yourself to. It makes you sort things out in your head.

That's in contrast to the unholy mess in my brain...

Jenny.

True enough.
The expressing of thoughts that is, not the unholy mess.
Although that may be true as well, I suppose.

One thing to add to the discussion is that whatever the outcome of the conversation might be, the relationship will change in one way or the other.
Not necessarily a bad thing, but something to be aware of. The risk-assesment I leave for those who actually know the people in question.
Not that I'm trying to scare anyone off, just saying.

You forget that I'm the one holding the whip...

Jenny.

Which would only make it easier.
Autonomous punishment, as it were.

[bound_jenny]

Do the math:

Unholy mess in brain + whip in hand = big trouble for anyone in whipping range.

But be warned - that algorithm might just overflow.

Jenny.