Questions about a close friend. Please help!

So he likes to have you humiliating him. But you are not his girlfriend. Is that correct? I assume that's so, because otherwise why would you feel it's affecting his personal life.

If you are his girlfriend, all you need to do is support him in this fetish.
If you are not, then what he needs is a woman who's into this sort of thing. There are girls who get off a lot on dressing their males like that and humiliating them.
 
So recently I discovered my friend is turned on by dressing up as a female. This includes wearing makeup, my bras, panties, and dresses. After getting dressed up, he likes being humiliated by me taking pictures of him and blackmailing him with them. In addition to that, he likes getting tied up, blindfolded, gagged, etc. He is very submissive and loves when girls dominant over him. I am concerned for his mental health seeing as how it is effecting his personal life and would greatly accept any advice if you have had experiences with this sort of thing. He hates that he is this way and I am looking for other people like him that he could possibly talk to.
-A Worried Friend

Cross-dressing as part of submission is a pretty common fetish. It doesn't have to be a problem unless he makes it so; when you say it's affecting his personal life, can you be more specific?
 
So recently I discovered my friend is turned on by dressing up as a female. This includes wearing makeup, my bras, panties, and dresses. After getting dressed up, he likes being humiliated by me taking pictures of him and blackmailing him with them. In addition to that, he likes getting tied up, blindfolded, gagged, etc. He is very submissive and loves when girls dominant over him. I am concerned for his mental health seeing as how it is effecting his personal life and would greatly accept any advice if you have had experiences with this sort of thing. He hates that he is this way and I am looking for other people like him that he could possibly talk to.
-A Worried Friend
You are his friend and he confides this to you, so you are a good friend?
May a sissy inquire how it is effecting his personal life? You mention his mental health.
How do you know he hates this way?

You may PM sissy if you would rather mot answer these questions in public.
sissy is a sissy and this makes sissy feel really great, sissy answers to Her (wife) and we are bff if this helps you.
Sissy Salina
 
I'm not his girlfriend. I really appreciate the advice. It's worn on me mentally as well so I feel it would be best for him to find a partner who enjoys doing that with him.
 
This is an Australian site, but some of the info might be useful, at least in showing him that he's not alone: https://gendercentre.org.au/resources/support-resources/cross-dressing

You may be able to find something closer to home by searching on something like "cross-dressing support group" (just be careful of fake groups that are actually fronts for "pray the gay away" type orgs). You could also ask on the LGBT forums here; I think there are several cross-dressers who post there frequently.

If it's gotten to the point of alcohol abuse, it might also be a good idea to look at professional help. The "Kink Aware Professionals" page hosts a list of medical, psych, and legal professionals who are aware of and sympathetic to unconventional sexualities: https://ncsfreedom.org/key-programs/kink-aware-professionals/kap-program-page.html

There are also pro-dommes who'll happily help play out these fantasies, but I think self-acceptance would be a better place to start.

Hope some of that is helpful.
 
Well, if you are not his girlfriend, first and foremost I would stop getting involved in his fetish. You said he likes you humiliating him and take pictures of him and blackmail him - that's too close to actually being his domme, in my opinion. If you are not interested in this sort of a relationship - find a way to drop it.
Especially now that you say it's taking a mental toll on you too.

See, the thing is that while he's getting his kicks out of you, while he's getting his need to be humiliated and blackmailed by a girl fulfilled by you, he's less likely to start actively seeking a girlfriend of his own. So I do think that in the long run you will be doing him a favor by stopping all that.
Just tell him that you started to feel uncomfortable about this, about being a "bad guy", and that you are stopping it. If he's a good friend, he'll understand.

Now for him, the best way would be hookup sites and fetish forums or fetish communities. For example on Milovana I've often seen an Ad about a group of men and women gathering up periodically to share this exact fetish - male crossdressing and humiliation. Everyone invited. He could find something like this locally for himself, meet new people, or even find himself a date like this.

Hook-up sites are good too. Often they will have kinky people looking for kinky partners.

The third variant is to date as normal but come clear early on about your fetishes. I never did it myself, but Matt Williams (rigger from kink.com and insex) likes to tell his story. That he would go on a date, and tell the girl on the very first date that he likes to tie women up. 80% would refuse to date him further after that, but 20% would instead actively seek him out to date him. I don't know how applicable this is, but there's a point of view. I'm personally not comfortable of doing such thing.
 
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