Gay Counseling

Not exactly a part of the sugar world, but I kind of give counseling sessions to bi-curious/confused crossdressers from time to time.  Mario came over to my place 2 days ago.  He quickly changed into a cute red top with flower pattern and a short denim skirt he brought.  I handed him a blond wig and a pair of red heels he keeps in my place (he can't take them home because crossdressing is a secret from everybody).  He was even wearing panties he had bought from me.  My apartment is the only safe place where he can be himself- a woman.  He is still very shy so he always wants me to initiate the conversation, ask him questions, or discuss his hopes, future plans and possibilities.  By answering my questions, he learns and understands more about himself.  My questions are like: "What do you fantasize about when you masturbate?" "What do you want to do to another man?"  "Do you want to give another man oral sex?  Do you also want to receive oral sex from another man?"  Etc.  It's actually kinda boring for me, so I suggested we go out to a gay club since it was Saturday night.  We tried a different gay club near the place we went to last time.  Just like the last time, the place was totally empty even though it was Saturday.  But music was really great so we danced for a couple of hours and we actually had a good time.  He had always told that he wasn't a dancer and he didn't know how to dance, but he was quite a dancer that night!  I guess he had to be pushed because he was super shy.  While we were there, he took a call from his daughter (She would have never guessed where her daddy was!!).  He used to be married and has three children.  Only recently he is coming out of the closet! 
He drove me home and thanked me for my time.  He handed me his wallet and told me to take some money.  I took out the same amount I usually get from him and gave him back his wallet.  We will try a major gay club with a better crowd next time so he can finally socialize with other gay men.  That is the next step for him; just talk to other gay men as a gay man.  Then one day he will have his first gay sexual encounter.

I'm still not talking to N.  It's been 5 days.  He knows I'm upset, but he doesn't know that I'm actually considering ending it.  I feel lonely and really want a real boyfriend more than ever.  I miss dating guys my age too.  Maybe I will go out with my girlfriends this weekend and meet some hot young boys.