Just came out and need advice

I just recently came out about six months ago and I feel so lost. I know I am a woman trapped in a mans body. I starting crossdressing about ten years ago and last year, at a halloween party, I was dressed in total femme and got drunk. I ended up flirting with this guy at the party and gave him a blow job in the back seat of his car. It felt so good and I enjoyed it. For the first time in my life I really felt like a real woman and I loved it! At first I felt overwhelming feelings of guilt and shame, but as each day passed I couldn't help but relive the experience in my head as I got so turned on by it. It just felt so natural. For the past six months I've been living totally as a woman. I haven't been totally with a man yet. I have only given several blow jobs and one hand job. In other words, I haven't had anal sex yet. I want to so bad, though. I am just afraid that it will hurt. Is there anything that I can do to prepare myself? I have a hot sexy gay friend who wants to be my first and he keeps asking me when I want to get together, but I'm just scared of him because he is really big. My mouth hurts and gets tired when I suck him off. I don't want to disappoint him. I wish I were a little more experienced so that I could please him the way I want to. He even bought me a cute sexy short dress and some very sexy high heel pumps with ankle cuffs for our first night. Please, can anyone help me.

 

"Blinks"
Well put on those pumps and bend over and kiss your ass goodbye...

 

What did you mean by that lilbear? You're scaring me. Is it going to be that bad?

 

Lol don't be mean lilbear.Anyway what he means his just say screw it and get screwed.It won't hurt.