The Bet

My friend Cristina and I were just sitting around watching porn. It's something we do for fun now and then. Believe it or not, it has never led to anything. A scene came on where a guy was put in a wig and satin nightgown and fucked by a beautiful blond dominatrix with a strap on. We laughed at what an ugly girl he made and somehow it came up that I had a girlish look to me. She said that I would look much more like a girl in the wig and nightgown than the guy from the movie. I just smiled.

Later that day out of nowhere, she told me that she'd like to test that theory. She wondered if I'd let her dress me up. Though about it for a moment and figured what the hell. It won't hurt anybody. Always been interested in cross dressers but never took the time to try it myself.

It's amazing how quickly she was able to apply my makeup. The hair was the easy part. I've been growing my hair out a little while so a wig really wasn't necessary. It gave me a more real look.

"So, what am I going to wear? I don't think your clothes will fit me."

" I think my sisters clothes might though, one second," she replied as she rummaged through the closet looking through her sisters large quantity of clothing.

"Wait, isn't your sister a stripper? I'm going to be dressed like a skank," I laughed.

"Yeah she is but that's ok. Here try this on," she yelled to me as she tossed clothing my way.

I looked at what she had thrown me. It was a pair of tight black leather pants and a black tank top that said "Slut" across the chest.

The pants were tight but they were suppose to be and the tank fit just right. Cristina just stared at me. I looked into the mirror to get a glimpse of the woman I had become.

"Wow, I look hot. You were definitely right, I do look a lot like a chick."

"Yeah...you really do look...good. I do a good job! I bet you could even fool people in the streets or at the bar," she smiled.

"Maybe, but I don't think I look that much like a girl to fool people," I replied.

"I bet you 50 dollars that you could fool people at the bar into thinking you were a girl. Hell, you might even get picked up by some guy. Want to take that bet?"

I froze. Stared at the mirror for a few seconds before finally saying, "Sure, I could use the cash"

It didn't take long for me to find a nice pair of boots that fit and for us to get down to the nearest bar. The moment I walked in I saw all eyes turn to me. That moment made me think this bet was going to be lost and I couldn't be more right.

Cristina sat down a few seats away so as not to interfere with what I was trying to do. Within the first minute, a tall dark haired man sat down next to me and asked if I wanted a drink, his treat. Figured that was harmless so I agreed. I couldn't believe that this was working, It was starting to turn me on.

I pulled out a cigarette and couldn't find my lighter. I must had forgotten it at home. Luckily the man offered me a light. Exhaling smoke into my lungs, we both smiled.

"Ill be right back, I've got to use the bathroom," I whispered to him as I finished my last inhale of the cigarette.

I couldn't seem to find the bathroom, the halls seemed never ending with too many turns. All of a sudden I felt a hand on my shoulder. I turned around to see the man who bought me the drink.

"Baby, you are looking real good. Getting me excited," he said as he grabbed my hand and rubbed it against his jeans before unzipping and pulling them down. I was a bit shocked and wasn't sure what to do. I told myself, go with the flow. I rubbed his large cock with my hand as he moaned softly.

"Be my little cock sucker honey, suck my big dick. You got sexy lips that are made for sucking."

Closing my eyes, I moved my head forward and let his penis enter my mouth. It was atleast 7 inches. I've watched enough porn to have an idea of what to do. Following what I've seen, I deep throated him. Every time I took him deeper I gagged but he loved it. Every moan he let out made my cock jump, pressing hard against the tight leather that wrapped my lower body..

Without thinking, I started rubbing myself through the leather and the feeling was incredible. He started to fuck my mouth fast and hard. My saliva dripped off his cock and all over my face. His hand grasped my hair, pulling it, to let me know he was in control. I didn't mind at all.

My mascara started to run a bit when he grew bigger as he got closer. He wanted every last inch in my wet mouth and I was trying to give him his wish. Sucked every inch as I rubbed his balls.

I couldn't hold on any longer, and I knew it as my cock exploded inside the leather pants. I felt the warm cum all over. I screamed in ecstasy which drove him to the edge. He shot a huge load of hot semen inside my mouth. It must have been awhile cause it felt like it wouldn't stop. His cum flooded my mouth and dripped out. My lips shined with it as it dripped down my chin and hung until hitting my shirt that appropriately said "Slut."

"Oh baby that was amazing," he barely got out as he panted. Zipped up his pants and walked off. I sat there wondering how I ended up here. I smiled.

Once I finally came out, Cristina followed me out of the bar smiling all the way.

"You definitely lost that bet. You still have cum on your lips!"

All I could do was smile as we walked back to her place.