What A Party Girl You Are, Dean
by: Jennifer Allison

 

It started as a wonderful dream-like weekend. That turned into a nightmare before the first night was over.

It started with my girlfriend Jennifer being asked to house sit for a friend of her family. I was invited to keep her company. I thought this would be a wonderful time to finally get inside Jennifer's panties.

I was a normal sixteen year-old boy with a normal hormonal problem. Jennifer has let me kiss her and I was allowed to do some petting. But everytime my hand wandered down to move up her leg, she stopped me cold. It was so bad, everytime I had a date with Jennifer. I had to go my room and whack myself in frustration when I got home.

Tonight I was not going to take no.

If I had known what I do now I would have never gone within a mile of that house.

 

My seventeen year-old sister Denise dropped me off before she went to work.

Before I could ring the doorbell, Jennifer opened the door and let me in.

For the next hour we watched TV. We even enjoyed a bottle of wine.

Then Jennifer said something I had been waiting to hear.

"Dean why don't you take your drink and head for the bedroom. I will join you when I get everything locked up and get into something more comfortable."

All of a sudden I had an embarrassing woody showing. When I tried to hide it.

Seeing my embarrassment Jennifer said. "Don't worry about it. We'll take care of that problem of yours."

With a smile on my face I entered the bedroom. As I waited for Jennifer I took off all my clothes. So there would be no mistakes about my intentions.

All of sudden my head started to spin. The wine I had been drinking must have gotten to me.

 

When I awoke I found myself spread eagled, and tied to the four posts of the bed.

"I see you are awake, Dean."

As I looked at Jennifer, all I could do was lie there with my mouth open.

Here was my sweet Jennifer dressed like a whore.

Jennifer was wearing a half bra that lifted and spread her breasts. That left her nipples in plain sight. She was wearing a garter belt that had a pair of fish net stockings attached. Her panties were so transparent and lacy. You could see the color of her pubic hair.

"I see you like what I am wearing, I hope so."

"I do, I do!"

"That's good. You are wearing a matching set."

It finally dawned on me, what the strange feelings my body had been sending me since I had awakened. Looking down my chest I could see a pair of falsies inside a half bra. Without looking I could feel the garter belt, stockings and the panties.

"Why did you dress me like this?"

"It is simple. You volunteered to help me with my job tonight. To help me with my job you need to be dressed as you are."

"What kind have job do you have? For me to be dressed like this."

"I am a Hooker. And for tonight so are you."

"You can't be a Hooker."

"Oh yes I am. You can't really tell who is a hooker and who is not."

"Why are you doing this to me?"

"You see Madam Olga, the madam I work for. Had a very special request from some very rich out of town clients. Four of the clients wanted a boy who was still a virgin. Have them dressed like a hooker and then spend a night of heavy sex with them."

"What if I refuse?"

"I wouldn't do that if I were you. While we were getting you all prettied up. We took a whole roll of film of the process. I think the school paper would love to have those pictures don't you. Then there is also the Internet. There is also the punishment if you cause any trouble later on. What do you think would happen if you were pushed out of a van right in front of the school as the crowd was leaving the basketball game tonight, dressed as you are? Also if you think you can say and hurt us later on. One day you could be walking down the street. The next day you could find yourself in the Middle East plying your trade as a She-male whore without a way of coming back to the US.

"I don't have no choice do I?"

"No you don't. But don't feel so bad. There are three other boys suffering the same fate as you are. If you are a good girl I'll even let you get inside my panties tomorrow."

"I am going to release you from the handcuffs now. Don't hurt me in any way or you will be on the next flight to the Middle East."

After spending the next ten minutes learning how walk in three-inch heels. I was allowed out of my room to meet the other girls.

 

I walked very unsteadily into the living room. I could see five others dressed as I was two girls and three boys. What I didn't expect was the voice I heard that I immediately recognized.

"Oh lookie here, my little sister has decided to join the party."

Turning around I found my sister Denise. Dressed as the rest of us were.

"What are you doing here?"

"My job."

"You mean you are a hooker too?"

"Yes I am. I am the one who got your sweet little Jennifer started in the business."

"Why?"

"I like the money. I make more in one night than I would do flipping hamburgers for a month."

"Does mom and dad know?"

"Dad does, he is one of Jennifer's steady clients.

"Come on over and meet the other girls, Deanna."

I didn't need to be introduced to any of the other girls. I knew them already.

There was my best friend John, who everybody was calling Juanita, Billy, who they were calling Billie Jo and Terry, who they were calling Teresa.

The two regular girls were Sue and Betty, Denise's and Jennifer's best friends.

"So what happens now?"

"In a few minutes our guests will arrive. They then will be taken to the locker room where they will strip down to their birthday suits. Then they will come here and make their selections. When you are selected you will go to your assigned rooms. For you new girls it is the room you just left. After that anything the client wants."

"Anything?"

"Anything, there is a jar of KY gel available in the nightstand when you need it."

"What do we need KY gel for?"

"It helps you take his dick when he puts it in your ass."

 

With that a bell rang. Then a door opened allowing eight naked men to enter. The one thing they all had in common was the 8-inch dick, standing at attention.

I asked myself. Which one of these hunks was mine?

What was I thinking, mine.

As the men mingled with us girls they started to pair off. One of the things that I didn't like was what Jennifer was doing. She was standing so close to one of these guys. His dick was rubbing against her. Before long the two of them were heading off to one of the bedrooms.

Then I saw Juanita being lead away.

As I watch this I felt a hand on my arm.

As I turned to face whoever touched my arm. I rubbed against his dick.

I touched someone else's dick other than my own.

As I stared at this guy he just nodded his head towards the bedrooms.

As we walked away I heard my sister say. "Enjoy yourself, Deanna."

As we walked through the bedroom door. We spoke for the first time.

"I hope you are gentle with me, I am still a virgin."

"I am always gentle with a first timer. After I am done you won't be a virgin anywhere."

I knew right there and then I would need the KY gel.

I melted as he took me in his strong arms. As he slipped his tongue into my mouth his hands were wandering all over my body. I could feel his dick rubbing against my legs. Without a second thought I did something I would never thought of doing three hours before. Using my left hand I was cupping his balls. With my right I was doing a jack off on him.

As he broke off the kiss he said. "Hey baby I would rather have a blow job than a hand job any day."

Without hesitation and not thinking what I was doing. I fell to floor and immediately replaced my hand with my mouth.

In the back of my mind I kept saying. Stop this right now. But the rest of me kept saying. I love it. I want to eat this guy's baby seed. Up and down I went. As the pleasure kept building he started to make me go faster by pushing my head up and down. Then all of sudden, he started shooting his cum. I tried to swallow as much as I could, but my mouth couldn't hold it all. Finally it stopped. I then turned to face the mirror in the room. I could see my reflection kneeling in front of a man's dick with cum still dripping from my mouth.

"WOW! Are you sure you haven't done this before? Cause that was the best blow job I ever had."

"Thank you. I hope that you enjoy taking my virgin ass as much." What the Bleep am I saying?

"Don't worry I will. But first I need to get you ready to take my monster."

He then started rearranging the pillows as I watched.

He then instructed me to remove my panties and climb up on the bed and lie there with my butt sticking in the air.

"The KY gel is on the nightstand."

"I won't need that yet."

Then he climbed up behind and started eating my ass. The first touch of tongue sent shivers up my spine. As he continued to eat all I could do was moan. "Please, don't stop, PLEASE!" I screamed. Then he reached around to my dick and proceeded to give me a hand job. I couldn't stop screaming in pleasure. I finally couldn't help myself and shot the biggest load of cum in my life. It traveled so far it hit me in the face. He didn't stop there. He started to finger fuck me one finger at first then a second. Before he could put a third I shot another load. It was even larger than the first one.

I finally collapsed onto to the bed into my own cum.

As my mind whirred around me I heard these words.

"Get up, we are not done yet. We have given each other pleasure. Now it is time to enjoy some pleasure together."

Without hesitation I raised my ass into the air, I grinned in anticipation as I looked back and saw the eight inch hard boner that was about to take away my maidenhood.

"What are you waiting for? Fuck me, like the bitch I am. Take that baby-making machine of yours and put into my manly womb. I only wish it was a real womb so you could fill me up with your baby seed so I could bear your child."

"Your wish is my command."

 

No KY gel was needed since my ass was already lubed up from the eating and finger job.

He teased me by rubbing the head of his dick against my buns

"Come on, put your love pole in my ass, Please." I begged.

"That is what I like a girl who begs to be fucked."

Before he finished what he was saying. I rammed his dick into my waiting ass.

I let out a very loud scream as his dick entered me. For the couple of minutes all I could feel was pain. As the pain subsided the pleasure started. With every push he made, he rubbed against my Prostrate. As I met every push of his with one of my own. I was taking his love pole deeper into my ass. Then I went into 7th Heaven. An orgasm followed by two more, before he filled my ass with his baby seed. Not to be out done, I shot another load onto my bed.

As we rolled over onto our backs exhausted.

"I hope I was worth every cent you paid." I said.

"You are, besides this was the first act. We have all night."

We didn't get much sleep that night. Everytime one of us up to it we did it.

I was even allowed once to take my pleasure of fucking his ass.

Finally we couldn't do it anymore.

I found myself alone when I awoke.

 

Jennifer entered a few minutes later. She was now dressed as she was when I first entered the house yesterday.

"Time to get you cleaned up, Deanna."

She then took me to the bathroom where she proceeded to give me enema to clean out my ass. Then I climbed into a bathtub filled with scented water.

As I reentered my room, hoping to find my old clothes, I was sadly mistaken. What I found was an identical match to what Jennifer wearing.

"Where are my clothes?"

"These are your clothes for today. I did promise you could get inside my panties. That is the pair I was wearing yesterday."

"You said last night, this would be for one night."

"I said helping me would be for one night. Now get dressed we have movies to watch."

"What movies?"

"Good movies, ones I know you'd enjoy."

After I dressed I went into the living room where I found the other three boys dressed as I was. None of the girls were in sight. As I sat down the TV started showing videotape. You can guess what it showed.

At first it showed the four of us as the girls turned us into hookers. Then it showed what took place in the bedrooms later. It even showed me as I looked in the mirror with cum still dripping from my mouth. It also showed when I begged to have my ass fucked.

As the movie stopped an older woman entered with the four girls.

"So you four she-males liked being hookers last night."

The four of us just sat there speechless.

"Starting today the four of you can start working for me. I have quite a few clients who would love to have sex with a boy in drag. Now I have four of them."

"What if we refuse?"

"You don't have a choice unless you want to see that tape spread all over town. So what do you think your friends and family would think when they see that tape."

We had no other choice. We nodded our heads in acceptance.

I never did get Jennifer to go to bed with me.

 

 

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© 2001 by Jennifer Allison. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.