Monica

Tonight was to be my big night, or Monica's rather. Monica was my alter ego, the girl I dressed up when I wanted to feel sexy and just a little bit naughty. She had never gone out on the town before though and I was very much looking forward to this evening. In fact, even if I were staying in I'd probably still be looking forward to it. You see, Monica had only even shown herself twice before and it wasn't at her best either. In the past her makeup at been minimal and applied amateurishly. Her hair wasn't as nice as it could have been and her wardrobe, while enough to make some heads turn, wasn't a knockout

This time was different though. I had gone all out for Monica spending nearly $200 on makeup, a wig, breast forms and a really sexy outfit: a black miniskirt and matching black halter-top. I also indulged in some sexy lingerie: black stockings with matching garter belt, a pair of black lace panties and a black satin bra. I wasn't sure if anyone else would end up seeing all of this but it sure made me feel a lot sexier.

After laying out my new purchases I drew a hot bubble bath and then soaked in it for about half an hour, letting the bath oils soften my skin. I then got out and shaved my face as close as I could, following up with some facial cream to make it soft to the touch for the men I hoped I would meet tonight. I then started to transform myself from John, your basic all-American guy who loved football and fast cars, into Monica, the sexy tramp who loved to make all the guys stiffen in their jeans. At least that's what I hoped she would do this first evening out on the town. I applied some black mascara first and then some black eyeliner. I then applied some base to cover up any trace of facial hair and followed up with some light rouge on my cheeks. Next I put on some light red lipstick. I looked at myself, herself, in the mirror and could see myself, herself, becoming beautiful right before my eyes. I then combed back my hair and put on my wig. It had been one of my biggest purchases for the evening but after looking at myself with it on I knew it was well worth it. It was my natural hair color, light brown, or pretty close to it, cut to shoulder length, straight but with a slight inward curl at the end. Picture Cameron Diaz in most of her pictures or Catherine Bell, that girl from JAG, but with brown hair of course.

With my face and hair done I next turned to my body, a body I hoped would be feeling at least a couple of pairs of hands on the dance floor if not a bedroom, this evening. I had luckily kept from getting too horny during this process and so was able to rather comfortably and easily push my penis down and in between my legs then hold it tight in that position with the panty-gaff I had purchased especially for this evening. I then slipped on my panties and matching garter belt and stockings. After that I turned to my breasts. I placed them on my chest and then put on the bra. I stared at myself in the mirror once again. I was become rather sexy I thought. Hopefully the men would think so. I then turned my attention back to getting dressed. I slipped on my miniskirt. As it slid up my legs and thighs, now smoothed by the stockings, a slight charge of excitement ran through my body. I hoped that later in the evening I would be feeling the same thing as some man slipped them down my legs. The only thing that was left was my halter-top. I pulled open the neck and slid it over my head. I adjusted my bra underneath the fabric and then gave myself one last look in the mirror to adjust my wig.

Gorgeous. I was sure to turn some heads this evening. I sat down on the bed and slipped on my heels. They weren't too high, just two inches. I already stood just over six feet tall without them and didn't want to tower over too many people. As it was I would already be doing so to some. I took a few practice steps back and forth until I got the hang of walking in the new shoes. The final step was putting on my fingernails, long and light red, the same color as my lipstick. I then grabbed my new purse, which I had also purchased especially for the evening. In it I put my lipstick and compact, a comb, and a lighter and a pack of Marlboro Lights 100s. I didn't smoke except when I dressed up as Monica and the unopened pack felt good in my hands as I slipped it in the purse. I also placed inside my wallet and car keys and a few condoms. As I put these in that same tingle went through my body as I imagined slipping one of them over some man's cock then taking him deep inside me.

When I arrived at the gay club that I had frequented many times before, albeit not as Monica, I felt a little nervous. Of course I was not the only cross-dresser that night and literally thousands had walked through the same door as I was about to but because it was Monica's first time I was a big uneasy. I pulled out my cigarettes, unwrapped the cellophane and opened the box then placed one between my lips. As I fished in my purse for my lighter a man came up to me with a lighter of his own and offered to light my cigarette for me. I cupped his hand in mine and guided the flame toward the tip. As I took my first drag, my head bowed slightly, I stared at him out of the top of my eyes. I hoped he would think this sexy.

"I'm Colin," he said, putting the lighter back in his pocket.

"Monica," I replied in a voice I had been practicing all evening. I was fairly certain he knew I wasn't a genuine female but I still hopped it sounded as feminine as possible.

"Nice to meet you. You come here often?" he asked.

"No, this is my first time."

"Well, maybe I'll see you inside."

"Yea."

I walked up to the door and I paid my cover then walked into the club. Across the room a small group of crossdressers and trannies were gathered. I decided to walk up to them. I wasn't sure if they would accept me into their little clique but I figured it was worth a try.

"Hello," one of them said as I walked up. "I love those shoes."

"Thanks. Hi. I'm Monica."

"Hi Monica. I'm Jessica and this is Stephanie and Nicole," she said introducing me to the other two girls who were standing there. "Have you been to this club before? I've never seen you."

"No. Actually this is my first time out in public."

"Congratulations," the three of them said. "You look good and I saw you walking over here. That was one of the hardest things for me to get the hang of. You do it well."

"Thanks."

As we were talking a man walked by and gave me a look out of the corner of his eye. I stared back and Jessica noticed this.

"Go after him, honey. He's a real hunk and by the look of the bulge in his pants I think he wants you."

"I sure hope so," I said, feeling my heart race just a bit. I left the three "girls" and walked over to the beau. "Hi. I'm Monica."

"James. Wanna dance?"

"Love to."

We made our way out onto the dance floor just as a new song was beginning. It had a real sexy beat and we were soon up against each other, moving to the music. I turned my back to him and ground my ass into his crotch. I could feel the hardness of his manhood rubbing up against me and it made me wet. He grabbed my hips and began dry humping me. I hoped that he would soon be doing it for real as I met each of his thrusts. Any uneasiness that had been inside me earlier had now completely melted away as I freak danced with this hunk of a man.

While we continue to dance another man came up to us. He greeted "my" man and James said hello back.

"How do you like dancing with my boyfriend," said this new treat that stood before me. He was the same build as James and just as sexy.

"Incredibly hot," I moaned, following it with a lick of my lips.

"This is Andy," James told me as he continued to grind his crotch against my ass.

"Hi Andy. I'm Monica."

"I hope you don't plan on stealing him away from me," replied Andy.

"I wouldn't think of it. In fact I'm hoping he'll share me with you," I said, reaching out toward his hips and pulling him in close. I was now sandwiched between two hunky men who were both grinding into me with their growing cocks.

"She's quite a hot little bitch, isn't she," James said to Andy as we all rubbed against each other.

"You have no idea, baby," I interjected as I moved my hands from my side and placed them on James's cock.

"Do you two feel like getting out of here?" asked Andy.

"I'd love to," I moaned.

The two men walked me out of there, one of my arms in each of theirs. I was feeling incredibly lucky to have snagged not one but a couple of sexy men that night. I was also feeling incredibly horny. My mouth was hungry for a couple of big cocks and so was my ass. We walked out to the parking lot and James opened the passenger door of his car for me. Andy got in the backseat. On the way back to their home the car couldn't move fast enough for me. We finally arrived what seemed like hours later but was really only about five minutes. As soon as we were through the front door we were all over each other, tonguing each other's mouths and rubbing our hands all over each other's bodies.

When we had finally made our way into the bedroom I dropped to my knees and began unbuckling Andy's jeans as James looked on, rubbing himself through his jeans. I slid his underwear and jeans down together and greeted my prize with a watering mouth. I bent my head toward his luscious cock and took the head between my lips. As I rolled my tongue around and around it I massaged his ass. I could hear him groan as I began bobbing my head up and down his shaft. As I continued sucking on this beautiful cock I felt another pair of hands on me. James had come over and began caressing my body, from my breasts all the way down to my ass. I was incredibly horny and my ass was craving a cock. I pulled my mouth off of Andy's cock just long enough to moan the words "I need my ass fucked."

The three of us then moved over to the bed and I allowed them to undress me. When they reached my panties and gaff that held my own cock in place I was a bit disappointed. In all the passion I had put out of my mind the fact that I had a cock and now having it spring up between us brought a bit of a frown to my face.

"Impressive," said James as he bent down and took it in his mouth. He obviously wasn't disappointed in the least.

I was so horny that I knew I wouldn't last long, especially with his tight lips wrapped around my cock. I pulled his head off of it and restated my request. He was a bit disappointed to not be sucking anymore but I promised him he'd get the chance before the evening was over.

Andy was now positioned behind me, the head of his cock brushing lightly against my hole, sending jolts of energy though my body. I pulled one of the condoms out of my purse and slid it over his cock. I then slowly guided him in, taking his entire length into my ass. As he began to slowly fuck my hole I concentrated on James. He had slid his crotch up to my mouth and I lowered my mouth down around his tasty member.

We all settled into a nice rhythm, Andy fucking my ass and James fucking my mouth. I moaned and screamed just like the girl I had wanted to be that evening. I had been fucked and I had sucked many cocks before but this time it was better than ever.

James was the first to cum, pumping his hot seed deep in my mouth. I gulped it down like the slut I was and relished the feeling of some of it spilling from my lips. When he had shot the last of his load I sucked him dry and then licked the remainder of his cum from around my mouth, using my fingers to wipe some of it from my chin. The whole while I continued to take Andy's thrusts in my ass. What had started out as a nice, slow rhythm had now become a good hard fuck and it was exactly what I wanted. I moaned like a whore as he went faster and faster. With one final, hard thrust he came as well. The three of us then collapsed in a heap on the bed and began to recover. I reached in my purse and pulled out a cigarette and lit it. As I lay there smoking, my head resting on James' chest, a smile crossed my face as I imagined how sexy I must have looked getting fucked by these two hot men. Monica's first night out had been wildly successful. It definitely wouldn't be her last.