So, I finally decided to embrace my inner sissy last week. Not full time, but as an active part of my post-divorce sex life. I have dressed and sucked about a dozen of times over the last several years...just testing the waters so to speak. But I decided to expand my sissy wardrobe and be more active in hooking up with guys.
So of course, my first experience ends up being my worst so far. After exchanging emails all week with a guy coming to town, I go to his hotel on Wednesday night. Hyatt Regency which is TOTALLY hot. Felt like a high class call girl going to service a guy at the nicest hotel in the area. Starts very well, he seems to like my outfit and the room has just enough to see things, but not show my non-passable face. He has a nice up-curved cock that goes a bit to his right. Cool. He's standing and I am on my knees and we are both having a great time. It feels like he is going to cum, then he stops. Things go down hill from there. After working on him for a half hour, I suggest he try fucking my face and watching porn over my head. For 15 mins he is doing this, but he is going very slow and basically just shoving his cock back behind the gag point of my throat. I am sure he has not intention of ever cuming and just want to abuse my throat. So for the first time I gave up. Then he says, "OK, it's probably not you, I came earlier". WTF! He picks the night and time saying he will be really loaded by then, THEN he blows his load and doesn't tell me! No way I was going back on Friday morning after that. Jerk!
After feeling I made a mistake in my new sex life, I get an email from a local guy who is horny (dah, why else would a guy contact me LOL). So I agree to meet him in a parking lot in his town and follow him to his place since he does not want to give out address (I don't blame guys for that). I won't get into a play by play, but that date made me feel much better. Far from the perfect guy - not very vocal and too laid back. But he had the perfect cock for my mouth. I wanted so bad. In addition to the perfect thickness and length, he had a very pronounced urethra (tube that the cum flows through). My mouth felt made for his cock. What stands out most is how my lips and tongue felt his urethra pump his cum into the back of my throat. since it was past my taste buds, I really did not get a chance to taste it much, but I LOVED feeling his muscles and tube flexing as he fill my mouth with his cum. I hope he invites me again!