A Shemale in New Orleans

New Orleans, Louisiana, May, 2001

As we approached the world famous French Quarter we were instantly excited. Bright lights lit up the street and the atmosphere reminded me of a carnival. People were everywhere! People were carrying giant buckets of booze as they walked the street yelling at women to take off their clothing. It was about 10 PM when we arrived and the party had just begun.

That first night, my buddies and I walked up and down the street consuming alcohol at a nearly lethal rate. We popped into a few strips clubs as we wandered around aimlessly. The girls were good and they were very willing to take you in the back for extras. I had never been one to pay for sex, but some of my friends had no qualms and took various girls up on their offers.

We laughed as we walked through the gay section of the street. Homosexuality was still a bit taboo at the time and we really didn't expect to see people this open in the south. It was a riot. Guys were dancing with guys and girls were dancing with girls. We even saw some of those stereotypical hairy biker dudes all decked out in leather - from head to toe!

We also noticed that there were a few 'special' strip clubs. Men dressed as women, and quite convincingly, would approach men walking on the sidewalk outside and invite them in. These girls were persistent - almost annoying. There were men, dressed as women, dancing in the windows and it all seemed so normal. Like other manly men, we walked by ignoring the calls. Unbeknownst to my friends, I was a bit interested.

When we settled back into our rooms - it was after 3AM - I decided I wasn't really ready to sleep. I was too excited. I left quietly, by myself, and headed back to the circus that was Bourbon Street.

I wanted to see those shemales from a little closer but I was hesitant to get too close. I certainly didn't want to be 'caught' by someone I knew while showing my curiosity. As I walked by one of the clubs I was met by this beautiful lady outside. Before accepting her offer to step inside I took a quick look around, which I realized later was more conspicuous than simply walking in, before I agreed.

After we made our way through the first set of doors I paid a man the $15 cover charge. My new friend held my hand as she walked me to a place along the bar. She sat down next to me, smiled, and asked me where I was from. I lied to her, I'll admit it. I also gave her a fictitious name.

With a double gin and tonic in front of me I watched these girls dance on the stage. If I didn't know where I was I would have had no clue that they were actually men. Gloria, who was still sitting next to me, put her hand on my leg.

My first instinct was to jerk away - and I did. After I took a few deep breaths, she convinced me to relax and returned her hand to my thigh. I watched the shemales strut up and down and the bar and I gave them tips as they passed. They were in all sort of undress but 'spare parts' were hardly noticeable.

After awhile, I could feel Gloria's hair brush my shoulder when she leaned in to whisper in my ear. Okay, she WAS absolutely gorgeous. She wasn't one of those over-the-top shemales made of plastic that you see on TV. She was better looking than a lot of the girls I have hooked up with, but there was one BIG difference. Although I was hesitant, I couldn't help but take her up on her offer for a private show. It would cost me $40, but I would certainly get my closer look.

She walked away to talk to a man who was standing by the back door. I could see her lean in and whisper to him before she looked back at me to smile. She handed him the two twenty dollar bills I had given her and walked back my way. When she was back by my side, she took me by my hand and led me to the back. The man gave me a quick frisk - I assume to look for weapons - before letting me accompany her further.

There were a few rooms in the back. Only one of the rooms was currently occupied. They were not fancy at all. They had the equivalent of a double wide park bench with no padding and plain black walls. Only one single light hung on the wall to my right.

She told me to sit and she sat on my lap.

Gloria: Talk to me baby, what do you want?

Me: I don't know.

G: Yes you do, don't be shy!

She stood up and straddled me - her face toward mine - and she leaned in and kissed me. I couldn't resist; I can admit now that I did kiss her back. I kissed as hard and as passionately as I had ever kissed before.

Her hands were in my lap and she unbuttoned, and unzipped, my pants. Her hands were on me as we kissed and I was as hard. She moved her mouth to my neck, kissing me, before lifting my shirt over my head. She placed her hands on my sides as our make out session continued.

Before long, she slid off of my lap and onto the floor in front of me. She pulled off my pants, and then my boxers, and put them on a small table by the door. I sat naked and aroused.

G: Can I suck your cock baby? Please tell me yes...

M: I don't know. You're a man.

G: I have the mouth of a woman and it will feel so good!

Without asking again, she engulfed my cock. I looked down at her and suddenly it didn't matter. She was right. She did have the mouth of a woman - even better than that! She knew what she was doing because she had felt it herself. She knew how to work me up and then bring me back down. She knew how to make me shake in delight and what it would take to make me cum, but she didn't let me. She couldn't let me cum just yet.

She stood up before me and lifted her skirt. Inside her panties, her cock looked back at me. It was surreal. As odd as it was to see it there in front of me, it was also hot. It was that forbidden hot that you just can't resist. I was tempted. She put her hand on the back of my head and pulled me closer. It was an inch from my face. Then she pulled me closer and I could feel it becoming hard as she rubbed it on my face through her lacy panties.

G: Do you want to make me feel good, baby? I know you do. Put in in your mouth for me. Let me see the other side come out of you. If you do it right, I promise I will make you cum. Please???

I had absolutely nothing to say. I opened my mouth and tasted it through her panties. She screamed out with joy. She freed it from the lace and I took it in my mouth. I gagged on it. I took it deep too fast. It was so big. How could a woman have a bigger dick than me? I don't know, but she did. I let it slide between my lips while I sucked. I was getting the hang of it now. I started to like it. I liked its smell, taste, and smoothness. It was unlike anything that had ever been in my mouth.

No matter how hard I tried, I could not make her cum. She pushed me back on the bench after only a few minutes passed and stroked her cock in front of me. I couldn't help but stroke mine. A little dot of clear white fluid emerged from the tip of her cock and she licked it from the side of her hand. A little more and she fed it to me. It was sweet, I was surprised.

She was back on her knees and it only took seconds for me to cum in her mouth. I had never came so much in my life. It was a fountain of cum and I shook with delight. She stood back up and licked her lips.

G: You taste good baby. Did you have a good time?

M: Yes, I did. Thank you.

G: Your welcome hun. Go ahead and get dressed.

After dressing, we walked past the man in the doorway. I gave her my credit card and she added the 'extra' charge for the special service. She gave me a kiss on my cheek and escorted me back to the street. As I walked toward my hotel I looked back and watched her as she attempted, and finally succeeded, to attract another man.