first time insertion today! (yay!)
 

I posted a long time ago about thinking about having my first experience with a tgirl. Well, I still have not had the guts to go that far yet but I did something else today for the first time ever! I was penetrated by a lady (escort) with a strap-on dildo!

I was really scared, I will admit. The mistress did NOT know what she was doing and was trying to insert it into my anus in such a sloppy manner. But finally I took the dildo from her while she massaged my penis and I inserted it myself into my anus. I got it in about 4-5 inches. It felt really good and I kept doing my butt until she finished me off. I was shaking when I finally came.

My butt does ache a bit now but I do feel it was totally worth it. I wanted a true tgirl but I am just too afraid of diseases. I am so happy that I finally got penetrated even if it was only by a dildo but at the same time I am depressed. I hate paying for any kind of intimacy in the manner that I did. As far as I have experienced, it just is not genuine and therefore not authentic to me. And since I have a girlfriend I don't think I will be able to have meaningful sex with either a tranny or get penetrated with a dom female that really likes me and enjoys penetrating me for me. (if that makes sense...)

And since I have a girlfriend I don't think I will be able to have meaningful sex with either a tranny or get penetrated with a dom female that really likes me and enjoys penetrating me for me. (if that makes sense...)[/QUOTE]

The un - expected price you pay.

Yes, it makes a lot of sense.

@franalexes - Yeah, I just kinda wish it could be real even if only for a while. Guess can't have my cake and eat it too. *sigh*

My anus is still bleeding a little bit every time I defecate but it only aches just a very small amount. I am yearning for another session but I just know it is going to be fake.

Ever since that experience, I really am beginning to understand how women feel when a man only wants them for their bodies and nothing more. It is a very crappy feeling.

On the other hand, though, I feel like I understand better the sacredness of (sexual) intimacy. I have little-to-no desire to masturbate, watch porn, or lust after beautiful strangers that I don't personally know and have a connection with. Just being in that submissive position and being dominated has revealed to my senses quite a lot.

Being taken is a great thing. Loosen up, and be eager for the ride next time. pleasuring your lover should be enough.

You sound like a really nice guy, and your understanding of womens feelings made me feel for you. It it called empathy or something? Anyway, maybe you could introduce the topic in conversation with your girlfriend - perhaps while watching a film with a sex scene? Say you want to experience what it's like from a womans pov? Christmas is coming - maybe Santa could bring a strapon? Just writing this has given me ideas for my own situation. But its a dangerous place to be - what if she laughs at you? Watch Last Tango in Paris - there's a scene where the girl puts her fingers up Brando's back door.
I hope it goes well for you.

Couldn't remember her name - it's Maria Schneider. I just found out she died last year, only 58. That's sad.