Last October my girlfriend Kelly and I were drinking wine and playing cribbage on a cold, rainy night. After dating her for six months we usually stayed in on weekends. I consider myself very lucky to be dating her. She is an incredibly beautiful brunette and has a perfect 36C-24-26 figure on her 5'5" frame. I, on the other hand am no Greek god at 5'9,"145 pounds. She says I am good looking and she loves me for being attentive, open minded, and thoughtful. We have great sex; having tried everything a man and a woman can do together. Anyway, after three games each, Kelly recommended we make the tiebreaker interesting. I asked what she wanted to bet. She said that the looser would have to indulge the winner in a sexual fantasy. The possibilities raced through my mind and I quickly agreed. I figured that even if she won, it would be something new.
Kelly won easily so I asked what I would have to do for her. Her big brown eyes gleamed with mischief as she told me about a big Hallowe'en bash downtown that she wanted to go to. She said that she would pick the costumes for both of us. I was a little disappointed, as it seemed pretty tame at the time.
Kelly arranged a room at the hotel where the big Hallowe'en party was being held. That way we could party and not worry about driving home. We arrived in the afternoon with four bottles of champagne, which we got into right away. Kelly had brought several other bags as well. She then drew me a bath and handed me a razor. I was instructed to shave off all of body hair. It was apparent that she wanted me to dress as a woman, which was fine as lots of guys did this for Hallowe'en. I shaved my face extra close. Kelly helped me the tricky spots like my butt crack, armpits, and balls. She made sure my legs were very smooth. At one point she asked, "Not easy being a woman is it?"
When I was done I had a huge hard on. Kelly, seeing it, dropped to her knees and gobbled it into her throat. She sucked me off with abandon and within minutes I let a gusher go into her waiting mouth.