Doug had to go away on business last weekend but gave me the ok to play...woo hoo. But his cousin Lamar called and said he was coming through. Friday night when he got there he seemed so pensive but finally blurted out, "Last weekend was amazing but what I really want to try is being a sissy." I replied, "So you want to dress up like a girl and be fucked like a girl.?" He said "Can you help me?" I said, "Well, I don't have anything you can fit..." He stopped me and said, "I have stuff. I've been dressing at home but I don't know where to meet guys and how to look really girly." I giggled and said, "Well I don't look really girly so the trick is finding guys who like men dressed as girls. Or gurls who like that. What's your name?" He said, "What do you mean?" I said, "From now on you're Alanna. Tonight, Alanna gets her cherry popped." I took Lamar to my room, had him strip and showed him how to prep to be a girl. Got rid of all body hair except a lil landing strip. Showed him some make up tips and boom, Alanna was born. I must say she was hot. Before she put anything on I had her lay on my bed and I got the lube and said, "Now, time to work your new pussy out cause the folsk coming tonight will fuck you good. After lubing that pussy up I slowly worked the tip of my dildo in her butt and slowly fucked her. She squirmed and rolled as she got used to feeling someone other than herself fucking her. After a bit I pulled the dildo out and hovered over her. She looked at me and said, "What are you doing?" I said, "You didn't think someone else was taking your cherry did you lol? Trust me, you want another gurl to be your first. I know how to make it feel special." Then I got between her legs and eased my cock into her pussy. As I did, she moaned, clutched me arms, her eyes rolling back. I pulled back and went back in a lil deeper. Once I got balls deep she gasped and twitched. I slowly picked up the pace and watched her eyes as I stroked her boipussy. She was biting her lip, rolling her head back, gasping and moaning. I must have been hitting her prostate because she began whimpering with her moans. I said, "Do you feel that?" "Yes!" "How's that feel?" "Om my god!! Fuck me. Fuck me." I picked up the pace and was driving my cock into her balls deep. She panted and groaned loudly, squeezed my back, pulling me on top of her and wrapped her legs around me. She began to shake under me and through her moans I hear, "Fuck, fuck, fuck, fuck. Oh fuck, oh fuck, fucccckkkkk!!!" And she shook out of control and I felt warm liquid between us. She had an anal orgasm and came hard and her moans were too much and I lost it inside her. I didn't even warn her, just drove in her deep and held my cock in her as I flooded her virgin pussy. As I did she grabbed my face and began to kiss me crazy, our tongues locked, my cock deep in her. After a few we calmed down and I pulled my cock out and her ass shot my cum back out. She laid there, legs spread, stockings rolled down and said, "This is what I've been missing all these years? I don't think I'll ever want a vagina again LOL." I said, "Nah, occasional pussy is cool, but nothing is like a good cock. And when you got a man you're really into forget about it. But now we gotta clean up because some people are coming over and you're going to be fucked like crazy." She smiled and we took a bath together. More to come. 

I wish I was coming over to take that ass.