I did a session last week with longtime lifestyle sub. After the session he said: "pegging just isn't satisfying me, I need be taken like a wanton whore!"

He asked if I'd allow him to include a Transsexual Mistress in our next session. I said: "I'm looking forward to it."

Have you ever been with, or fantasized about a Transsexual Domme.

It is an idea that has come into greater focus of late and I intend to make it a reality in the next year. When I think about it, it puts me in another realm of submissiveness. While i am exploring possibilities, i think a trip to Dallas will provide the opportunity I seek.

Yes, I have crossed that line. I started a topic on Max asking if strapon play leads to being with a transient. Most said no but for me it was a yes.
Most have been extremely attractive. Will be in LA next week and going to see one I have already been with.

It sounds like you are making tremendous strides down the road, in your submissive journey!

Is the real thing significantly better than a dong? Breaking a societal taboo is always exciting, is that a factor?

Since you asked. Just like a dong it depends on size. Everything being equal it does feel better. It is part of a persons body and obviously they can feel the pleasure also.
Also, if you find the right person there is a “reward” at the end.

Who is in Dallas? I will be there in 3 weeks.

There are a couple of TS Dommes in Dallas that advertise on Eros but I wouldn't assume that is on the table.

Thanks. I have seen those ads. There is a website called tsescorts that breaks down their role. Top, versatile, etc.
I don’t think the ones on Eros advertise there.

I sent a message to MsRoseWoods and she encouraged me to post this.

My simple answer is yes. There are two strange stories, especially for an old straight guy.

The first is from the late '90s and I saw an ad for a gorgeous Latina Mistress who began working at the old Arena Blaze dungeon in Midtown Manhattan. Busty, big lips and eyes, great hips... I wanted to serve. Heck, I wanted to devour her. I called Arena a week later and was told abruptly, "She's not here anymore," and hung up. A couple of months later I found out why they were abrupt. A new escort ad appeared with the same picture of someone named "Allanah Starr," the now-famous TS porn star, model and dominatrix.

Fast-forward to the early 2000s. A very voluptous and Amazonian Mistress from SF worked in a Wall Street dungeon for around a year. We hit it off. By the second session she wanted to peg me. I'm not into it but did worship her strap-on orally and she was impressed. She knew I wanted to worship her more intimately, so she said, "The only way I'll allow it if you worship a TS. Pick out one and call me later." Stunned, I did what I was told and found Allanah was still around. I told the Mistress. She said, "Make an appointment, worship her cock, and have her call me as proof." (Selfies were not yet a thing.)

I called Allanah and told her the story. She was pretty skeptical but told me to come in at noon on a Saturday for a half hour session. Allanah was out late Friday night and had just woken up, but had on clear high heels and her breasts just about plunging out of her sheer red bikini top. She led me to her bedroom, which was dimly lit, and sat on the edge of the bed and said, "Show me what you got," or something like that. After I stripped she had me kneel down, she put a condom on her cock and ordered me to worship. I closed my eyes and could only do it a minute or two and then stopped, kinda petrified. Allanah, seeing I froze up, said, "That's okay honey, I'll call your Mistress." I quickly got dressed, got a hug from her, and left.

Allanah did call, according to the Mistress. I never saw Allanah again. I spoke to the Mistress and she said she had to go back to SF, but we'd session when she got back. She never returned to NYC.

Here's the second, shorter story. I began to see female bodybuilders, some of whom are dominant. One was from Europe back in 2003 or so. Dark hair, busty, strong back and shoulders, around my height (6' 1") in heels, athletic but not overly muscular... gorgeous Wonder Woman type. We would see each other once a year until 2009 in NYC and every time the sessions got more and more intimate.

She got into my Amazon/ sub Tarzan role play with some play wrestling, spanking, muscle worship, etc. Finally I thought after some hot emails this was the session we would get intimate. Well, every attempt I made to begin to try and worship her I was stopped. It was erotic but close to a real wrestling match. It was a good session but as I left the hotel she was staying at, saying to myself, "How could I be so wrong?"

Then a light bulb went off in my head.

I called her up to thank her for a wonderful session. I then told her, "You really have some special abilities and are built... differently than any other woman I've ever been with." We talked around the subject further and I finally said, "No matter what your physique is, you're the hottest Amazon I've ever been with." She laughed and said, "You're the first client that ever figured out my secret!"

She was not a transsexual but an intersex or hermaphrodite with the sex organs or physical characteristics of M & F. I saw her two more times after that. (I also found out that she was rather well-endowed.)

If I was younger all of this would have shook me up. But strangely, for this old straight guy, neither experience drove me to question my own sexuality or kept me up at night wondering. I thought of them, still do, as gorgeous Mistresses I served. I'm kinda proud of that.