I was floored by what Tracy had said to me. “Because, the male Jesse is no more for the time being, it is womanly Jessie that needs to go.” It seemed that my love just told me that I had to meet up with my male friends tonight. My mind was going a mile a minute. I already fooled my friends once. But can I do it again? If I do, what is going to happen? What will I let happen? My stomach felt like butterflies. I was getting a little nervous.

“Are you saying that you want me to dress up and meet them again?” I asked Tracy.

“Hun, you made and lost the bet. They are expecting you to fulfill your payment. Don’t forget, last night you technically did. But none of your friends know that because you never gave yourself up.”

“But babe, I really want to be with you, and only you,” I replied.

“And you are. But you need to fulfill your payment. The sooner you fulfill it, the sooner we can live our lives together.”

Tracy’s logic made sense. I do need to pay up on my lost bet. The only way to do so is to meet my friends as Jessie, have them pick me up, and then give up my secret. Although I didn’t want to do it, it had to happen. My same conflicted thoughts of enjoying dressing up and feeling feminine were welling up inside. I couldn’t wait to dress-up for tonight, yet I wanted to make love with my love Tracy.

My thoughts were interrupted with, “Come on dear, we need to get you ready.”

************************

It was ten-o’clock and we were back in line at Club 54. Tracy was all smiles as we waited for our turn. The bouncer from last night walked by us and immediately recognized me. “Hello sexy, I remember you and your friend from last night. Please come with me.”

As we walked past the line, several women gave us sneers, dirty looks, and called us all sorts of caddy names. The bouncer continued to escort us to the entrance. “Have fun ladies!” With a smile and a wink, he turned and left to card patrons going in.

When we entered into the night club, I immediately spotted my male friends. I turned to Tracy and said, “I can’t do this again.”

Tracy replied with, “Why not Hun?”

“Because, I’m…”

Tracy finished my sentence, “You’re afraid that you’ll like it and you’ll lose me.”

I nodded affirmative.

“You will never lose me hun. We are in this together. I will support whatever needs you have. I love you for who you are, and will support you until from now until forever.” Tracy kissed me passionately.

Heads turned as the two of us were locked in a passionate kiss. Fireworks were going off in my head and my girly heart skipped several beats. We both forgot the world around us as we continued to kiss each other. I was so in love with her, and could not imagine life without her. Right now I wanted to take her home with me, and make out girl on gurl. I looked at her with loving eyes. She saw the love within and started to kiss me again, when suddenly, “Ladies! So glad to see you here again!” It was Adam that approached us. “Mark and John will be so glad to see you here again. Come join us?”

Tracy looked at me and nodded. She grabbed my hand and led me to where my other friends were located. Once we got to their table, Adam said, “Guys! Guess who showed up tonight!”

Mark looked at me and said, “Hi there sexy! So glad you came back. I take it you really liked the Mark experience and wanted a second round.”

The Mark’s sly little smile and comment almost made me walk away. Tracy saw my unease and quickly put her hand on my arm for reassurance. I looked at Tracy with hesitation showing all over my face. When she started stroking my arm, my hesitation slowly started to resolve. I sat down next to Tracy and then John started hitting on Tracy. I looked at him as the self centered pig that he was. Then it dawned on me, I have only been dressing up as a woman for 36 hours and I’m already noticing how poorly my friends treat women. We were all just pieces of ass for them to conquer. It really put into perspective what my friends where really about. I started to realize that I really don’t want to hang around men that have no appreciation for a woman. I wanted to be treated with respect and feel a man’s comforting body. Wait, did I really just think that? I did.

After several drinks, I was starting to loosen up. I took turns dancing with my male friends. For some reason, they kept placing their hands on my hips and ground into my backside. At first, I didn’t want that attention, but after several drinks and having let lose, I started to get somewhat hot from their hands on my hips. Eventually, I started grinding my rear end into my friend’s crotches. I felt a great thrill knowing that I am fooling my friends into thinking I am a woman and not one of their friends. I also loved the fact that grinding my ass into their crotch was getting them all hot and bothered. I seriously wanted to give them a major case of blue balls for all of their crudeness.

All too soon, it was midnight. I was really enjoying myself with my friends. Sexual innuendos were flying all over the place, and my friends couldn’t keep their hands off of me. Even though I was feeling no pain, I still was aware of their hands and I made sure they weren’t getting to close to my boy clitty. Finally I saw Mark whisper to my other friends. They all smiled and nodded.

Mark looked at me and said, “Come on babe! Let’s go back to my place. You’ve made quite an impression on my friends. They want to continue the party.”

For some reason, I went with Mark.

*************************************************

The drive to Mark’s house was, shall we say, eventful. On the way there, Adam started rubbing my fake breasts thinking he was arousing me. He kept commented on how real and beautiful my breasts were, and that he couldn’t wait to suck on my nipples. A small little laugh escaped my lips. If he only knew they were all silicone and fake as fake could be. I humored Adam with several moans and asking him to keep playing with them. What shocked me is that Adam unzipped his pants, grabbed my hand, and placed it inside his opened pants.

Adam whispered into my ear, “Stroke it baby. You know you want it.”

It was like someone flipped a switch in me. I went from not wanting to go to Mark’s house for another round, to wanting a nice hard cock in my hands. I quickly took his hard cock out of his pants and started stroking this marvelous piece of male.

“Mmmmm, baby. That’s it. Now I want you to lick off that drop of lip gloss at the end of it.”

I immediately lowered my mouth to his beautifully hard piece of meat. I couldn’t believe in just under a day that I was going to have fun with another one of my male friends. I thought, two down and four more to go.

This moment made me realize one thing. It was no longer about proving to my friends that I can pick up a guy while dressed. It was about conquest. I was turning the tables on my friends. My new self administered goal was to have video of each of my conquests, and I was going to enjoy every moment of it.

We pulled into Mark’s house and one thing struck me. Where was Tracy? I quickly excused myself and texted her. A reply came back that she ended up sick and couldn’t find me, so she went home. The last text was about having fun and enjoying myself. A pang of guilt came across my conscience. My love was not with me. But then again, it also spared my agony of watching one of my friends having his way with my love.

We went downstairs to shoot some pool and have a couple of drinks. I quickly whipped out Tracy’s camcorder and started filming our games of pool. During the games of pool, I purposely showed my friends some cleavage, leg, and ass. Finally Scott piped up, “Let’s put a little wager on this. Winner gets to choose what the loser has to do to him.”

I quickly agreed as I knew I could beat them. What I didn’t catch was what the loser has to do with him. Yes him. Did that mean they knew about me? Or was something more sinister going to happen? Either way, I was bound and determined that I would win. Then I can have complete control of the night and turn the tables on my friends.

The first game was me against Scott. Several times while I was shooting, one of my friends would squeeze my ass which caused me to miss my target. I was soundly defeated by my friend. He gave a little smirk. As Scott unzipped his pants, he said, “Alright Jessie. I want you to give me some head.” He quickly took his cock out and pushed me onto my knees. It was like two magnetic opposites. I quickly engulfed his cock into my mouth. It seemed in no time that I had him on edge.

“Alright babe, that’s enough.” Scott said as he pulled his saliva covered cock out of my mouth. I felt saddened that he pulled it away, but I also knew this was just the start.

The next game was against Adam. Just like the first game, the boys kept messing with me and I lost soundly. “Alright Jessie, I want to tie you up and fuck you.”

Oh no, the quandary. If I let it go, then I am caught. I had to think fast. Then I remembered last night. “I can’t let you fuck me. It is my time of the month. But, if you wish, you can take my ass.”

As Mark grabbed the camcorder and aimed it toward me, he shouted out, “See! I told you that she would let you have her ass! She’s such a nice little slut!”

Adam pulled my panties aside and stuck his cock right next to my boy pussy entrance. I moaned at the feel of his nice hard cock slide back and forth against my cheeks. I lifted and lowered my hips several times so his cock was sliding between them. I felt a cool liquid dribble down my crack and into my boy pussy. Adam moaned by the stimulation of my boy pussy.

“Ok you little bitch, it is time to feel my nice hard cock inside of you.”

Adam aimed his cock at my pussy and thrusted it into me. I yelped in pain by the sudden intrusion of his cock. Several tears came from my eyes and down my cheeks as Adam started to slide in and out of me.

Adam said to our friends, “Damn! She’s got a tight ass! So fuckable.”

The comment made me cringe to the point that my boy pussy muscles clinched up. Pain returned to my pussy as Adam continued his thrusting into me. I yelled out, “Ouch! That hurts really bad!” Just then, tears started forming.

Even with how crude Mark was earlier, it was ironic that after he saw the tears well up in my eyes, and the look of pain in my face, he asked Adam to stop. At first, Adam continued to thrust into me. When another plea to stop came out of my mouth, Mark grabbed Adam’s shoulders and told him to stop. When Adam finally stopped thrusting, I turned to Mark and leaned over to kiss him.

After we kissed passionately, I whispered to Mark, “Thank you sweetie. I want to enjoy tonight by being treated like a woman, and not be taken forcefully.” Oh crap! I just did it again. I almost gave it up before I was ready.

Mark replied, “Babe, we want you to enjoy tonight as well.” He slapped my ass and continued, “I want to enjoy your ass many more times.”

The third game was against Mark. I lost that one hands down without any help from Scott or Adam. After all, Mark was a very good pool player. He reached over to snuggle me into him and started kissing me passionately. Suddenly, he lifted me off of the ground on sat me on the pool table. From there he pushed me back so I would be laying on my back. He proceeded to lift my legs and then adjust me so my sexy ass was at the edge of the table. Then he lined up his cock and stuck it into my boy pussy. Oh how good it felt to have his cock inside of me. This drove me so crazy with lust that I couldn’t help but to ask him to fuck me like a good slut. After ten minutes of pumping inside me, he suddenly shouted “Oh Fuck! I’m cumming!” With one final thrust, his cock spurted shot after shot into my pussy. After a couple of minutes, he pulled out of me.

“Ok you hot little piece of ass, it is my turn.”

Scott took Mark’s place and thrusted deep inside of me right away. I was going crazy because his cock had a nice arch that rubbed my prostrate the right way. On top of that, Scott was slightly thicker than Mark so the sensations of his pumping felt really good.

“Oh god, you are a nice piece of ass. I’m going to fuck you so good that you won’t even want Adam here to do it to you.”

I wrapped my legs around his back and said, “Ohh baby. Your cock feels so good inside of me. I want you to shoot your load in me. Make me your little cum slut.”

Mark smiled and said, “Oh shit! This is too good to be true. I have to call the rest of the gang.”

Mark dialed the phone, “Ross! Hey it’s Mark. Come on over! We have a really hot babe here that is on fire. She wants to be banged!”

After he got off with Ross, he called up Steve. “Steve! Mark here. Hey come on over. We have this really hot gal that wants to get gangbanged… Yes. Ok. See you shortly.”

Mark looked at Scott, John, and Adam. “Good news. Ross and Steve are coming over! Now all I have to do is get a hold of Jesse, and all of us will have had this hot little slut in the same night.”

He picked up the phone and dialed my number. Even though Scott was getting me close to orgasm, I started to freak out. Scott sensed it and caressed my face. “Relax babe, enjoy this. Trust me, you’re going to enjoy the load that I will give you.”

Scott had no clue why I was freaking out. It wasn’t that he had me on the verge of orgasm. Oh no. I loved every second of his cock going in and out of me. The feelings inside of me were nothing that I’ve ever felt in my life. I knew this would be my biggest orgasm ever.

So why was I freaking out? It was my phone, it was in my purse, and it wasn’t on vibrate.