Interesting topic of discussion.  The "friend/clint" lines are so blurry and situational it can be very confusing.  This would seem to apply to both GG/TS.

It has been my experience that meeting a TS outside of the escort world can be tricky.  

For a number of reasons, many t-girls find themselves working in the escort world.  As if being open about being a t-girl to a guy you meet isn't difficult enough, revealing that you are an escort will probably be even harder.  If you meet as an escort and client, there is no need to worry about going down that road in conversation.

There was one time when I ran into a very beautiful girl in Palm Springs who I thought might be a TG or a GG.  Either way, I was interested in her.  As I was talking to her and not making much progress, I found myself wondering how hard it might be for a TG to be open about herself without worrying about repercussions from someone who is not into girls like her.  The only idea I could come up with to let her know that I was ok with meeting a t-girl was to suggest that she looked familiar and I asked if she had ever been to a club in Hollywood called Peanuts.  If she was a GG,, she probably wouldn't have heard of it.  If she was in fact a t-girl, I thought this might be a good subtle way to let her know I was interested in t-girls without coming out and asking or saying anything directly.  In the end, I didn't get much conversation from her at all so it didn't go anywhere.

Anyone have similar experiences they would like to write about or suggestions of how to handle this type of situation?

There have been a handful of girls that I met as a client and we became friendly.  We went to dinner and/or a movie or just hung out, but the relationship never progressed very far.  At least one of the girls was looking for a sugar daddy and that's not something that I'm interested in being.

Having just "crashed" in the above referenced situation, a few observations:

With Christy Delight and I, it started as a business.proposition. But,her close proximity to my then-office location (walking distance) led to casual lunches, then drinks after work, then dinner dates, then weekends together.

Her sunny, light, open personality, her sense of humor, and her great beauty soon had me entranced.

At some point, a relationship developed. We fell in love. She asked me continually if her "escorting" bothered me. She also asked me how I felt about dating a t-girl socially.

I told her that being with HER socially and romantically felt like the most normal and natural thing in the world. I did my utmost
to convince her that I ACCEPTED her...that her
profession and her "t" status were, to me, no
barrier to being in a normal relationship.

In retrospect, I was wrong. I overlooked two issues. First, that escorting requires that there be a certain emotional distance between the client and the provider. Breaching that distance doesn't necessarily harm the client but can be devastating to the provider.  Emotional entanglement can mean that the provider just can't get "into it" to provide sex on demand anymore. Whethter or not that proved true in her case I don't know ..... but, I feel it weighed on her mind.

The second issue, which I think is more specific to the TS world, is one of validation....that a TS woman, can in fact be accepted as female by normal heterosexual men both socially and sexually. To the TS escort, I feel that this may mean that the "civilian" (i.e. non-client) heterosexual male is the "gold" standard ...his presence means acceptance as a woman, and his "civilian" status means no "escorting" issues
to deal with.

Christy and I certainly had our discussions and issues...but, I feel that in the end, not being civilian (being originally a client) meant the relationship was doomed. My personal problems (trying to turn around my business) didn't help. Finally, to preserve the sanity of both of us, I made the choice to pull the plug.

Was I right or wrong? I don't know. Was this whole thing a wise decision? Don't have the answer there either. Were the odds with me on this? Probably Not.  

I would be very interested in hearing any "lessons learned" from anyone else who has a similar experience....

Sory to be so lengthy, but for me it's therapy...

TA

I cannot comment on if what I experienced was doomed or not. Let me begin.
When i first moved to Houston, I met quite a few TGs in the club scenes. Began a combination of friendships and as client to a small few. One night while being involved in the hankypanky side of things,a beautiful young TG walked into the room on her way to the one bedroom apt shared with 2 other TGs. The LEGS caught my attention immediately. By the next weekend I introduced myself to her out in the clubs.She and I hit it off socially and we enjoyed a night of partying.At the evening end, she asked if I was interestdd in a 'date'. I was and I said so. So we began a series of dating that went into months and months. The sex was incredible as was her demeanor for just hanging out and cutting up. We had become friends rather easily. We  called each other and talked alot.One night she called and said she needed a place to stay for a few days. I let her stay with me a week until she could get herself a place. Our arrangement was not of a business one but as a friend helping out a friend. She ended up slipping in the bed with me most every night because she didnt like feeling lonely. This is when the sex became intense beyond a client/provider provider. We actually started kissing and stuff. She confessed to enjoying feeling like my little housewife while there. One of the nights she was there I had just melted in her wonderful sweet ass sans condom and both our feelings just came bursting out. I told her how I felt as did she and we both agreed we had crossed a barrier of some sort. What do we do about it we wondered. We decided to let it continue as it were.Friends,lovers,client,provider. She spent many a night with me from then on and I left her that space when she was in working mode. Th understanding was she could stay in my bed most any night she wished and I could see other providers if I chose to. I chose other providers because she was not a top. She had no problem with this arrangement. Time passes and we all find other love interests. She fell for some guy and became totally involved with him and moved from Houston. Understand that I was much older than her and I knew that we would never become a true romantic commodity with our age gap. We had emotional and sexual needs and mutually helped each other with those needs. I have no regrets other than it didn`t last. Hindsight being 20-20 we both knew it would not. I still consider her a friend and would welcome her back in my life at any level we or she chose.