Dreams Do Come True!

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Crossdresser dream.
1.3k words
4.06
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A couple of years ago I finally got the nerve to rent a room in San Francisco South of Market and spend a night going out crossdressed. I searched the Internet and bought everything I would need, dress, wig, make up, perfume, heels, and all kinds of other things.

I was so nervous when the afternoon finally came to check in and I spent about five hours getting ready, totally shaving smooth from head to toe, and finally when I felt I looked good enough, I walked out onto the street after the sun had gone down.

Going out in public for the first time was everything I dreamed it would be. I felt so at home being dressed like a woman in public. It wasn't even sexual, just totally fulfilling.

I walked the few blocks to the Cat Club which I had read likes crossdressers to come in. I stayed until closing after drinking a lot of cranberry vodkas and dancing. Everyone was really friendly and a lot of girls and guys talked to me. The girls seemed to enjoy me the most.

While I was at the bar a big stud started chatting me up and pushing close to me. He pulled me close to him and my heart started beating so hard but I went with it. It was the first time I had ever nestled up close to a big man and I felt so happy.

Suddenly he reached up under my dress and fondled my sissy clit and ass. I got rockhard instantly and absolutely melted. I would have let him do anything to me. I had on pink panties that said "sissy" on them with a little pink bow and he just pushed those aside and put his big rough hand on me underneath them.

I was so disappointed when he said he could not come back to my room and had to work in the morning. I finally left the club at closing disappointed I had not gotten picked up. I was pretty liquored and beyond horny. I was hoping a car would stop and a man would pick me up but nothing happened.

I got back to my hotel room very frustrated and told myself fuck it, I'm going to get a cock if it's the last thing I do and I stripped everything off except just my short dress and wig and heels, smoked a joint, and went back out on the street.

The cold air against my shaved bare legs and up my skirt felt really exciting for some reason. I stood on a street corner as cars drove by and was checked out by a lot of men who drove by. Some teenagers drove by and laughed at me and called me names and I didn't even care, it only made me feel like an even cheaper sissy whore.

I was so nervous that the police would drive by and arrest me. After about 20 minutes I noticed a big black guy across the street walking down the sidewalk looking at me. He slowed down and then stood in a doorway watching me.

My heart was just about beating out of my chest but there was no way I was going to run back to my hotel room in fear. He walked down the street a little and stopped again and looked and then worked his way over to my side of the street and slowly made his way to me and then finally he was standing right by me.

He asked me what I was doing out so late and said a sexy little white thing like you could get hurt. I said I just wanted to get some fresh air and he asked if I would like to hang out and I said I would and he asked if I had a place to go and I said I had a room right around the corner so he said let's go there.

As we were walking to the room he had his arm around my waist and I was beyond excited. He suddenly stopped and pushed me against the side of a building and begin French kissing me, shoving his tongue down my throat and I absolutely melted.

I felt myself swallowing his spit and I knew from that point on there was no return to any sense of heterosexuality. He fondled my rock hard sissy clit and bitch ass through my dress and I would have had sex with him right there if he had gone further but he suddenly away said he was going to turn me into a real girl.

In the elevator he continued to make me suck on his tongue and feel me up through my dress, saying that he was going to fuck my white bitch ass. The rest is almost a blur.

When we entered my hotel room he immediately threw me on the bed. He told me to keep my mouth shut while he took my thigh high nylons off a chair and tied my wrists to the bed posts. He stripped naked and I saw he had a gorgeous body, very muscular.

Fortunately his cock was not too big because I knew he was going to fuck my virgin ass with it. Rather than kiss me or anything he just walked over and stuck his cock in front of my face and told me to suck it.

He kept slapping my face and ass while I sucked it and calling me names. I could not believe that I had a naked black man having sex with me.

He fondled my tits so roughly and sucked on them so hard that they were bruised and sore for days and every time I touched them for the next week the soreness made me horny again and made me think about him.

He sucked really hard on me all over my body and left marks all over. I had some oil next to the bed and he put some all over his cock after he made me suck it for what seemed an hour.

He put me on my back and just shoved it in me and it hurt at first but then it became the most pleasurable thing I've ever felt. I threw my arms back and was literally laughing with joy while he fucked me.

I was finally a girl and it was the best feeling I've ever had in my entire life. The sounds he made were so hot and he kept calling me all kinds of bad names.

He kept sucking on my neck and left all kinds of marks all over it.

Finally, I could tell he was going to cum and I felt his cock starting to shoot in my ass and he pulled out halfway through and shot sperm all up my body from my ass to my face and shoved his cock in my mouth while he finished cumming, laughing and saying "You're a real bitch now, you sissy whore".

I had never swallowed a man's cum before. I kept thinking to myself that there was no more denying now that I was a gay sissy crossdressing whore for life.

He immediately got dressed, just leaving me on the bed covered in cum and as he was about to leave he saw my wallet on the table and reached in and took my drivers license and all my cash and walked over to me and grabbed my hair and spit on my face and called me a white sissy whore who got what she deserved and said I would never know when he would find me again now that he had my address.

I have lived in so much fear of him finding me yet it's all I can think about. I want him back so bad. I would wear a wedding dress and ring for him and do anything he would make me do.

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KathyXXKathyXXabout 1 year ago

Enjoyed the story, it brought memories.

SabrinaGLangtonSabrinaGLangtonabout 1 year ago

Sounds like you were having fun. I was into it until the penultimate paragraph, ha, but it's your story, not mine. Thanks for sharing...

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