He was much older than I, but he had a lot of money. He was very important to his company, and traveled extensively. We were only dating two weeks before he bought me a very expensive diamond necklace. The only real problem was, he didn't perform too well in bed. With all the other benefits, I just decided to deal with it.
We had made plans for the weekend, when at the last minute, he had to fly down south for a big meeting. I begged him to take me with him, and he finally agreed. We flew down, and had a limo take us to the hotel, where he stayed whenever he came here. We walked up to the desk, and the clerk looked at me like I was trash, then spoke to Kevin.
"Good afternoon, sir. We are so glad you are staying with us again," he motioned slightly towards me," I see you've made your own 'arrangements' this time."
"Um, why, yes, no need for anything special this trip. If you could have my bags brought up..."
"Yes, sir, right away." As we walked towards the elevator, I looked back to see the clerk and a few other employees staring at me, whispering and laughing. I knew it would make me look even worse, but I couldn't resist giving them a unique finger gesture just before we boarded the elevator. Kevin didn't even notice.
The room was beautiful. A fully furnished suite, with a hot tub, fireplace, and a gorgeous view of the city. I jumped on the bed, and lay back, looking up at Kevin.
"What 'special arrangements' were they talking about in the lobby?"
"Oh, they were talking about, um, transportation, yeah, that I had my own limo bring us here, instead of them sending someone to get us. That's it."
He sat down with me on the bed, and started unbuttoning my top. He slipped it off my shoulders, and caressed my tits as he kissed my neck. I unfastened my bra, and let it fall free, then I laid back. He moved up on me, and gently kissed and licked my nipples, making them perk up hard. He tugged down on my very short and naughty skirt, to reveal no panties.
His eyes opened wide, he smiled, then lay down on top of me. His fingers pressed into me quickly, I groaned slightly, he always did that, not letting me get wet first. He kissed me deeply, his fingers slipping in and out until I was finally wet, and it felt good. He sat up, I moved to him, and opened his pants. I let his cock out, and gently stroked his shaft. I kissed the tip, letting my tongue wiggle against the slit. My hand went down to his balls; I squeezed them firmly, as I let the head into my mouth.
I sucked his hardening penis while I kept fondling his sack, letting him go deeper into my throat, until I had him all the way. I sucked harder, my lips gliding up and down him, my tongue teasing along as it slid by. He groaned, then held my head firmly, and shot his sperm into my throat.
I closed my eyes, thinking how I was going to get off now, when the phone rang. He had to run off, they were having a last minute meeting before the presentation. He kissed me on the cheek, and told me he'd be back in a few hours. Then he crossed his arms, and looked down sternly at me.
"Kayla. Swallow it, now." I did. Ugh.
I brushed my teeth, and then went into the hot tub. I lay back, and gently played with myself, feeling the warmth of the water, and the warmth of my own pussy.
I brought myself to orgasm 5 times, before I got out, and took a nap. When I woke up, it was dark, and Kevin hadn't returned yet. I watched some cable, but nothing good was on. I looked over some brochures for the area, but that was boring, too. I thought I heard Kevin outside, so I quickly went to the door, still naked, to greet him. I peeked out, but there was no one there. I looked right across the hall, there was a tray on the floor, with some dirty dishes, and a newspaper! Finally, something to do. I looked both way, all clear, and I quickly went out to get the paper. Just as I bent to pick it up, I heard my room door slam shut. Leaving the paper, I tried to open the door, it was definitely locked. Just then, the elevator rang. I looked around, panicking, when I saw the stairway door. I opened the door, and went in the stairwell, and let the door slam. I heard a click, and then I read the sign.
"ATTENTION! No Access to This Floor! Proceed to 1ST Floor Lobby!"
What was I going to do? I sat for a while, shivering, the air was on, and the cement stairs were very cold. Finally, I went down stairs. 16 floors. When I reached the lobby, I noticed a housekeeping cart just outside the door, with a hotel towel on it. I stepped out of the door, and what seemed like fifty, but probably only about ten, people stopped and stared at me. I grabbed the towel, and wrapped it around myself; my face must have been bright red. I went up to the desk. My "friendly" clerk was still there.
"Excuse me, I accidentally locked myself out of my room, could you get me another key to get in again?"
"What? You think I'm stupid? Mr. Helmwithe has been back in his room for the last 45 minutes. If you were locked out, he'd let you in. All you hookers are the same; obviously you did something wrong if he kicked you out with just a towel. I'm not going to waste his time with you, just leave, and we won't call the police." I screamed, yelled, and then begged him to call up to the room, but he wouldn't. He picked up the phone, then two big men came up, picked me up under my arms, and carried me to the door. The clerk called to them.
"Hey, that towel! It's hotel property!" One of them grabbed the towel away, and they literally threw me out the front door naked, into the street. I looked around frantically, trying to cover myself. Men, women, staring, pointing, several even took pictures of me standing there. I ran back in, rushing past all the people in the lobby, up to the desk. I cried, pleaded, and finally, he made an offer. Give him a hand job, and he'd get me clothes, and a cab home. It was disgusting, but I wasn't in a position to argue.
He took me into the back office, and made me take out his cock. I stroked him hard, jerking fast, but not rough, trying to get him off quickly. Then the door opened, three other employees walked in.
"Whoa, what's this? Party time!" Before I could even argue, I was pushed down onto a couch. "Where'd ya get her?"
"She's Mr. Helmwithe's prostitute, she finished early, he's giving us a free bee, we'll send him up something special in thanks, but for now...Gang Bang!"
They held me down, while the first man passed on his hand job, and put his cock down my throat. I had him so hot already, he blew quickly. I gagged, and swallowed weakly, while he pulled out, and splattered more cum on my face.
As he stood up he said, "I'll get the others, I'll be back!"
He left, and the other three took over. One forced his long cock down my throat in one hard thrust, while the other pushed into my barely wet pussy. The third stood over me, stroking himself patiently. In and out, I lay on my back under these two, cocks driving deeper, harder, faster. I didn't even notice after a while, 15 other men came in and were watching.
My mouth, with no warning, suddenly was filled with hot semen, and almost at the same time, cum was spurted up into my now very wet and messy pussy. I tried to gasp out to the word stop, but suddenly I felt like I wanted it. One after the other, one in my mouth, one in my pussy, they all took turns, I was screaming in orgasmic delight, too high to resist them.
I was brought to reality quickly, when I felt a pain like never before. I squirmed, and kicked, but I was quickly pinned down. I tried to scream for help, but I was gagged with a pair of men's underwear. I shook, crying, as my ass was being fingered open. Two, three, rubbing cum on my hole to lubricate me. I felt the head of a cock pushing on me then. I tried to pull away, but it was no use. Deeper, slowly, the thick cock stretched me open, deeper up into my ass.
He made it all the way in, then he pulled back slowly. Without warning, he slammed himself all the way back in! I felt my face drain as I tried to scream, my eyes almost popping out. He rammed up into me, harder, harder, then he held it in, and filled me with his cum.
I had perhaps 5 seconds rest, when another man took me from behind. After several of them came in my ass, I had to go, but they kept on pounding me. After everyone had come in my ass, they let me relieve myself into a pitcher. Then they made me drink three glasses of my own cum laced piss, before I got sick, then passed out.
When I woke up, I was still naked. There was dried cum all over me. I looked around; I realized I was lying in an alley, surrounded by dumpsters. I was nowhere near the hotel. This area was obviously a very poor and bad place to be. I could barely walk, as I went down to the street. It was just getting dark, and I looked up and down the street. Then I saw them. A gang a black guys.
Before I could move, they saw me, too. I ran back into the alley, but I did not get very far. I lay on my back on the grimy ground, squirming as they grabbed at my tits and pussy. One called out "first," and four others pinned down my arms and legs. The rest of them surrounded me, looking down at me grinning like they'd just won the lottery. I was helpless.
Again, one by one, thick, dirty cocks were thrust deep into my sore but still wet pussy. I stopped struggling after about the eighth man, but when they rolled me over, I fought back again.
They took my ass, tightened up since my last time, it hurt even worse. After everyone had taken me, from both sides, my pussy and ass spurting and dripping cum, the whole group of them, maybe thirty or so, stood over me, and filled my mouth and tummy, with their bitter piss, before I heard the sirens. They all took off, leaving me lying there.
Two cops walked up. "Yup, another fuckin' hooker. Get up, whore, time to spend the night in 'girls school' again."
I tried to protest, but they just laughed. I was cuffed, and put in the police car still naked. I was taken to the station, led through the entire building, all the way to the back, completely naked.
The desk sergeant pulled me aside after having allowed me to take a hot shower, "Cooperation is the key here, lady. You could spend a little time here with me and a few boys, or you could spend a month here waiting for a trial."
He unzipped his pants, and I answered him by getting down on my knees, no longer worried about my nakedness.
I sucked off all 8 male officers, when a very large, mean looking policewoman walked up. She opened her pants, she wasn't a clean woman. I said no. The others pulled me to her; they made me lick her awful pussy clean. Then the first man came up again.
"I told you if you cooperated, you'd get off easy. Now you made us have to fight you to get between Greta's legs, and we have to lock you up for the night. We don't supply clothes here, so, since you chose not to wear any, you get to stay that way."
I was taken to the lock up, which consisted of two small cells. Both of them had 4 men in them already, drunks, gangbangers, and troublemakers.
"We got to get all 8 of them in one cell, we got a bitch tonight."
Greta laughed. "No, put her in with them. She's a prostitute, she don't care."
I struggled with the officers as they forced me into the first cell.
Greta came to me. "If this cell doesn't suit you after a few hours, we'll put you in the other for a while." She laughed loudly and evilly, as she locked the doors, and left me there, still naked.
I ended up being raped by the men in both cells. When the ones in my cell were fucked out they held me up to the bars of the cell and let the men fuck me bent over.
The next morning, the big butch cop brought me out, and took me to a private room. There was a simple, but pretty outfit hanging in there. She pointed to the clothes and then took off her pants. She lay back on a desk, her legs over the side, and waited. Slowly, I approached. I got down between her thick thighs, and licked her. She pulled my head to her awful crotch, and held me firmly as I licked her into 4 orgasms. She pushed me to my knees, and squatted over me, her bush right on my mouth. Then she urinated, I pulled back, her hot fluid trickled down my tits, before she grabbed my hair and pulled me back to drink her piss.
"You worthless bitch, you didn't earn those clothes! Go get your pimp, and don't let me catch you on the street again, or I'll SHIT in your mouth next time!"
The head officer ended up giving me the clothes, then he drove me to the hotel where I said my "pimp" was staying. I walked right in, past the clerk, up the elevator, to our room. I knocked on the door, and another woman, wrapped in a blanket, answered the door. I was shocked. I looked down.
"Sorry, wrong room." Then I walked away.
As I was leaving the elevator, I realized I had no money to get back home. Just then, the clerk walked up to me again.
"Hey, if you're finished again, we're having a bachelor party to night, and we need a good hooker. We'll pay you two grand if you'll do the party."
I was ready to slap him, but I stopped myself.
I flew home first class the next day.