Preface (skip to good part if you hate reading):

It had been a year of a sissy adventures, and I was traveling this past week and have been on and off grindr for a little while but never really met anyone. The predicament of not being attracted to men but the thought of enjoying cock/toys was a bit overwhelming to my curiosity. Being in a large enough city I started conveniently met up with a girl (trans) I had actually talk to in a different location, that had moved across the state ironically enough.

GOOD PART:

We met up and went to a well known "goth" bar, we kissed a few times there, and went back to where I was staying and hooked up. We started playing, but she was very small and had been on hormones for a while therefore I don't consider it a "real" cock. I let her fuck me for a little while and it did feel good but almost just peaked my curiosity more than anything. I then fucked her, sucked her, and jerked her until she came. I did not cum, but it felt good enough to make me want a "real" cock.

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Day 2:

I was lucky enough to see a very pretty transwoman wanting to "top a fatass" I figured it was spam but took my shot anyways. Turns out she was real. 4 miles away and had missed her cruise so was staying in a airbnb. We exchanged pictures, and I decided I would go pick her up. The entire process was extremely nerve racking, but I knew I needed to go through with it to finish my exploration of if I really would like a real cock or not. I saw her pictures and she had a real (black) cock about 5.5/6" and very thick. When we got to my place she lead the way by just getting straight into it and taking her clothes off in the room. I followed and sucked her for a bit, she bent me over and I struggled so bad trying to put the condom on it was embarrassing, I was surprised she was able to stay hard as long as she did with me fucking it up. We eventually got it in, and started slow, but then she forced it a bit in me and anyone who has had it knows the feeling, I felt ripped open and had to back off for a minute or so.

She apologized, I settled down and then put her on her back and road her. She asked to fuck me raw and I said no. She was cool about it and didn't push the issue. I road it and got warmed up before she turned me doggy. While she was fucking me doggy it was 3/4 minutes of pain/pleasure mix def more pleasure once I settled into it, then 3/4 minutes of pure pleasure where I thought maybe I was going to cum (not touching myself/limp). I remember thinking at one point "this feels so good I need another 2-3 minutes and I think I will cum" and about that time I think I was having an orgasm and she ended up cumming and slowly stopping. I still didn't "cum" but felt extremely satisfied but also stayed horny into the next day when I had to cum.

Overall: Positive experience, no regrets, felt really really good and definitely want to do it more, my main issue is not being attracted to men. Ideally I can find a transwoman to actually build something with and have a regular play partner or more.