1. First taste of cum for a Crossdresser!


    Date: 11/19/2017, Categories: First Time, Gay, Trans, Author: sxyhispanic26, Source: xHamster

    I had never really been with another man before and I had always thought about it as I dressed up as a slutty girl and played with my little toys to orgasm. I'm a little tall at 5, 9 and with heels a monster! I have an average body, nothing feminine, but not out of shape and a nice big bubble ass. Until that night. I had been sent to Dallas for a business trip and was super excited to dress up in my hotel room and play around! I played around a couple days in my room and just got dressed did my make up and wore my wig playing with my little dildo before passing out exhausted from all the fun! It was one of my last days and I really wanted to go out, but since I am not passable and not fully confident I didn't know what to do. I had a bright idea! I would order something for delivery and let the delivery person see me all dolled up! Well I was very nervous and excited! I had a few drinks to settle my nerves and I got to work on getting all dressed up just perfect! I slipped on some lacy red panties, trying hard to hide my excited bulge! I slipped into my baby blue bra and slipped in my breastforms. I grabbed my sexy red dress, which already had been used this week and had a small cum stain on it from my last orgasm, but it was the sexiest thing I had. I slipped into the red dress that didn't quite reach my knees. I then pulled up some sexy black thigh high stockings. to complete my outfit I slipped on some very tall red pumps that I wobbled in when I walked. I took them off ...
    while I did my make up though, I didn't need to fall over! I went to the mirror and applied my black eye liner and mascara very carefully, I needed everything to be perfect! I added some light green sparkly eye shadow and some powder to my face to make me more soft looking. I added a little pink to my cheeks and finally added some bright red lipstick, smacking my lips together as I tested out kissing, and a quick fake blow job ;). Everything was just about perfect! I went and got my brunette wig and put it on. I was a knock out gorgeous, almost passable girl! I would have definitely been excited to take me home! I took a quick look around and my ass was eating my red lacy panties, just the way i liked it to. I decided I needed to order and couldn't figure out what I wanted! It wasn't about the food, but the delivery person! I wanted to wow them with my sexy features and maybe steal a kiss! I finally decided on a chinese restaurant that delivered straight to my room. I quickly ordered, using my most feminine voice, and then quickly started another drink as I waited for my order. I was definitely feeling a little courageous now with a couple drinks in me. i slipped on my shoes and practiced what I was going to say. When I heard the knock on the door I almost fell over! I quickly straightened out my clothes and cleared my throat for my most feminine voice. I didn't peer through the peep hole, just in case I lost my nerve, I opened the door and there stood a short, white boy about ...
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