Sherrie's New Job

The first of the month was almost here and once again I didn't have the rent money. My landlord had been letting me slide because he knew I was out of work and having trouble finding a job. But I knew this was the last straw and would be evicted if I wasn't able to pay this month. Life hadn't been easy the last year. Part-time jobs through a temp agency were about all that I could find and they weren't lasting long enough for me to make any money.

Two weeks ago, I was having lunch with my friend Ali and happened to mention my struggles. Now she was calling me with a proposal that I was having a hard time wrapping my mind around.

"I've been doing this since late last year. Six or seven times now. The money is great! How much you make is kind of up to you. It just depends on your comfort level with the situation." Ali told me over the phone. "There's this group of high rolling business guys who get together about once a month at the Ritz in Chicago and have a party. They hire four or five girls to come in and help liven things up."

"What do you mean, 'liven things up'?" I asked, even though I pretty much knew what she was saying.

"Well Sherrie, like I said, it really kind of depends on your comfort level, but the friendlier you are to them the more money you can make. The first time I went, I was pretty overwhelmed, so I ended up spending most of the night walking around in my bra and panties. I did give a couple of guys lap dances and the last hour or so I took my top off. I made $500 that night."

"$500 isn't going to pay the rent!" I said.

"Well each time I've gone I've gotten more and more comfortable being around these men with my clothes off, and at the last party I made $4000!"

"$4000!!?? Are you kidding? What did you do for $4000?"

"These guys seem to have an unlimited amount of cash, and they really start throwing it around when the entertainment value goes up. I think you can use your imagination, but the wilder the better and there seems to be no end to the money."

My head was spinning at the proposal. I had never even considered stripping for money, let alone hooking!

"Sherrie, these guys are really nice. They treat all the girls with respect and don't force anything on you unless you allow it. You would fit in well with the other girls and the guys would absolutely love you!"

My heart was beating in my throat, but the thought of being able to fix my money problems quickly won out. "Okay I guess it wouldn't hurt to try it out, but if I don't want to continue we leave. Deal?"

"Deal!" Ali promised. "We can drive up to Chicago together on Friday afternoon. I'll pick you up at 3:00pm. The guys like short skirts, heals and tight tops. You should also wear your sexiest bra and thong!" she said as she hung up.

The week passed quickly as my mind raced through a million scenarios of what was going to happen. I was scared, but must admit that my juices were flowing all week and I masturbated several times to mind blowing orgasms.

Ali picked me up at the appointed time and we drove to Chicago. She continued to offer her encouragement and tell me how much the others were going to like me, but I had terrible nerves and almost backed out just as we pulled into the drive of the Ritz. As the valet opened our doors, Ali came around and grabbed me by the arm and playfully ushered me into the lobby.

We went straight to a bank of elevators and Ali pushed 'PH'.

"These guys have the penthouse?!" was all I could say as the elevator shot skyward. As we stepped out we were greeted by two very well-dressed men who appeared to be in their mid to late forties or maybe even 50s. Both were handsome and obviously worked out regularly.

"Ali!" they both echoed as they took turns giving her a hug and a kiss on the cheek. "And you have a friend" one of them said.

"This is Sherrie. She's a little nervous, so maybe you guys can help by getting her a drink."

"Absolutely! Welcome Sherrie. Please come with me." Brad said as he offered his arm and escorted me into the suite. Upon entering, most of the rest of the guests repeated their salutations to Ali, while she gave me a group introduction, which was greeted by many more friendly welcomes.

I must say, it seemed like I was among a group of friends instead of a bunch of strangers. Even the other girls took the time to come over to give me a hug and introduce themselves. Maybe this wouldn't be so bad after all I thought to myself as Brad handed me a drink, which I quickly drained to ease my nerves.

I caught Ali for a private moment then asked, "So what do we do now?"

"Don't worry, the guys will take the lead. Remember, you don't have to do anything you don't feel comfortable doing, but I will warn you right now that the guys are very straight forward and will be very blatant in their requests. That's how it works. Just have fun!"

As Ali walked away to join a couple of the guys near the bar, I noticed one of the other girls, Jenny, was already bare chested and Mike was behind her kissing her neck and pinching her nipples.

I must have been staring because I didn't hear Brad come up from behind and whisper into my ear, "That could be you and me if you'd like."

Startled, I turned to face him and said, "Think I could have another drink?"

He led me over to the bar and fixed me another stiff one, which I again promptly drained. The alcohol gave me a quick buzz and allowed my nerves to settle a bit.

"May I have the honor of a dance?" Brad politely asked. "Why of course dear sir!" I answered feeling more at ease.

As we danced, Brad held me tightly against his hard body. I remembered Ali's words about the money flowing when the 'entertainment value' goes up. With that, I melted to Brad's body and straddled one of his legs. I could feel his cock hardening against my thigh as he slowly ground into me. To my amazement, I was getting wet and was enjoying the physical contact.

Then I looked over Brad's shoulder and almost feinted. Ali was now topless, leaning against the bar with her skirt flipped up onto her back, while one of the guys kneeled behind her slowly licking her pussy!

Brad noticed too and said "I love eating pussy myself. Would you mind?"

The moment of truth was upon me. My mouth opened, but nothing would come out. Brad guided me onto a couch and fell to his knees in front of me. I could only gaze at him with disbelieving eyes as he gently raised my knees onto his shoulders, pulled my g-string to the side, and slowly licked my inner thighs. His tongue quickly made its way to my wetness and entered my pussy. Tasting my juices, he moaned his approval. As soon as his tongue hit my clit, I saw stars. My legs instinctively clamped around his head, pulling his face fully into my cunt. My orgasm erupted immediately as I bucked and rode his face for several seconds. It was the most intense orgasm I had ever experienced and I milked it for as long as I could. Then I realized that everyone in the room was now watching us. As it ended, the room erupted in applause and cheering!

Embarrassed, but trying not to look too awkward, I let go of Brad's head and lowered my legs, while pulling my skirt back down.

Ali yelled across the room "Girl! You are going to fit right in!" which was greeted by another round of cheering.

Brad reached into his pocket and pulled out five brand new $100 bills and lovingly slipped them into the string of my thong. "You're a beautiful lady Sherrie. Thank you for allowing me the honor of tasting your sweetness."

As Brad walked away, Jerrod sat down next to me. By the looks of the tent in his pants, he had been turned on by the previous show. "Sherrie, I'd love for you to suck my cock." At this point I almost felt like I owed someone something, so I slowly lowered my head toward his lap and he quickly unbuckled his pants and pushed them to his knees, releasing a very hard cock that sprang straight up. I reached out with my left hand and gently grasped it at the base and slowly stroked up and down the full length. Jerrod's cock head grew bigger with each stroke as I lowered my mouth and began tonguing the underside of the helmet. This caused him to get even harder as my stroking picked up and I took more of his head into my mouth. I was now on the sofa on my knees with my ass sticking up, although I was unaware of my position, my pussy was surely visible from behind under my very short skirt. It wasn't lost on Brad, because as I was giving full attention to Jerrod's throbbing prick, I felt my g-string being moved to the side and felt a blunt object rubbing up and down my still wet pussy.

I took my mouth off Jerrod's cock just long enough to glance over my shoulder and see Brad slowly easing a large rubber dildo into my pussy. Holy shit! What was I doing! I thought about breaking it off, but I froze as the head of the dildo pushed into my cunt.

"Oooohhh!" was all I could say as Jerrod pulled my top and bra off my body with one quick yank. I redirected my attention to Jerrod's cock. My pumping and sucking had picked up steam. Brad was now working the dildo in and out while twisting it up against my clit. At the same time, he reached under me and began squeezing my tits and pinching my nipples. Brad began matching the rhythm I had going on Jerrod's cock and before long we were both pumping as fast as we could. My orgasm slammed into me just as he sank the dildo to its full length, flipped on the vibrator and held it fully in my hole and against my clit. I exploded as I grabbed the base of Jerrod's cock with both hands and began milking massive shots of cum from his prick. I sucked and sucked every drop of his goo, emptying his balls completely down my throat as Brad eased the dildo out of my hole inch by inch while keeping the vibration directed to my clit, which continued to spasm uncontrollably.

As I finally collapsed back onto the couch, both Jerrod and Brad kissed me on the cheek and each peeled off seven $100 bills and gently tucked them into my g-string.

Ali came over and helped me to my feet, then led me into the bathroom where she handed me a tooth brush. As I brushed and gargled some mouthwash, Ali brushed out my hair and touched up my make-up.

"The guys like us to stay fresh" she said as she pointed to a row of drawers. "Pick one and keep your money in there. No one will bother it." As I pulled the $100 bills from my g-string I asked, "Is it always this crazy?"

"You haven't seen anything yet! Just enjoy and make some money!"

As we walked back into the suite, I stopped in my tracks as I saw Jenny and one of the other girls, Marla, on the round ottoman locked in a 69. The guys were going crazy as the girls worked their tongues in and out of each other's pussy. Ronnie and Pete both had their cocks out and stoking them, while Brad eased onto the ottoman directly behind Jenny with his balls hanging down near Marla's face. He eased his cock head against Jenny's pussy. Marla gave way enough to allow his prick to slide in. She then continued licking Jenny's clit and the shaft of Brad's cock. Brad began sliding his cock in and out of Jen's pussy, which caused her to moan and double down on Marla's twat making her squeal in pleasure. Soon they were all going at it in a frenzy of fucking and sucking until both girls writhed in orgasm, shrieking loudly. Suddenly, Brad withdrew his prick from Jen's pussy, pointed it straight down at Marla's face and began shooting ropes of hot white cum into her mouth. She allowed him to empty his load as she continued to cum from Jen's attack on her clit. Once Brad finished cumming, Marla put her mouth back onto Jen's pussy and squirted Brad's entire load into her hole.

Ronnie and Pete had now moved in front of Jen. Pete put his prick in her mouth as Ronnie positioned the head of his cock against Marla's twat and entered her. Both men began pounding away in their chosen openings. Within seconds, each were groaning in unison as they too blasted shot after shot of jism into the girls.

I was mesmerized, but then noticed that Jerrod had Ali bent over the couch and was giving her a good fucking from behind. He had her by the hips and was lifting her feet completely off the floor as he hammered her pussy while never taking his eyes off the action on the ottoman. Jerrod was really turned on and he obviously wasn't going to last long. His balls were slapping against Ali's ass as he let out a deep groan and started shooting his load deep into her hole.

I can't explain how I felt at that moment, but I was well aware of my pussy juices running down the inside of my thighs. Apparently, this wasn't lost on James, who stepped in behind me, then gently bent me to the floor until I was on my hands and knees. He wasted no time flipping my skirt up and pulling my g-string to the side. The head of his cock was huge. He slowly worked it into my pussy. Once it was inside, he merely leaned forward as inch after inch of his giant cock disappeared into my wet hole. Soon he was buried to the hilt and held it there for several seconds while I adjusted to his massive size. I'd never had a cock this size in me. He was easily 10 inches long and at least 4 inches around. I was stretched to my limits, but wet enough to take it.

All the other action had subsided as we now became the main attraction. Everyone took up a position to best watch us as James slowly withdrew his manhood before slowly re-entering me inch by inch. As he pulled out, his cock sawed across my clit, sending shock waves through my body. As he re-inserted, the friction doubled making me pant with pleasure.

"Fuck her man!" one of the other guys said. "Give her that meat!"

Needing no further encouragement, James leaned onto my back, reaching around and grabbing both my tits, he pinched my nipples and squeezed my tits, pulling me back against him with each thrust. His knees were now off the floor as he dug his feet into the carpet for leverage and began slamming his giant cock into my hole.

I was totally overcome with pleasure as I started screaming, "Fuck my pussy! Fuck my pussy! Your cock feels soooooo good! It's so fucking big! Fuck my cunt!"

Just as I was about to hit orgasm, James pulled out and laid back on the floor. His huge prick sticking straight up. I immediately felt empty and needing filled. Without hesitating, I literally jumped onto him and sank down onto his cock. Wasting no time, I began riding his prick like a woman possessed. Humping up and down and screaming with pleasure as I banged my way to orgasm. "Aaaaahhhhh!! My pussy! My pussy is cumming on your big cock!! Cum in my hole! Shoot me full!" I screamed as I continued to hammer away on his pole. "I'm cumming!" James screamed, as his first blast nearly lifted me off his dick. I spun off his cock just in time to see the second load launch three feet in the air. I grabbed his prick and pumped him as another rope of jis shot skyward. I then lowered my mouth onto his still erupting cock and sucked the final few shots down my throat, milking him until he was spent.

As I swallowed the last of James' cum, I thought things were over for a while, but at that very moment, I felt a set of hands on my shoulders directing me to my back on the floor. Apparently, Jake wanted his turn, because he immediately placed my legs over his shoulders and sank his cock into my pussy. Wasting no time, he unceremoniously started banging my pussy for all he was worth. Slapping his balls against my ass as he fucked me like I've never been fucked before! "Do you like my cock in your pussy? You want me to fuck you good?" he asked as he slammed into me.

"Yes! Yes! I love getting fucked by your prick! Give it to me! Fuck me harrrrrddd!" I screamed as my orgasm shook my body. Jake was far from done, he continued to pound my pussy for several more minutes. Then, without warning, he pulled out and rolled me over onto my stomach. Using the juices that were running out of my pussy, he inserted two wet fingers into my asshole and slowly circled them around. "No! I can't take it there!" I pleaded. But Jake didn't hesitate as he replaced his fingers with the head of his cock and pushed it into my bum.

"Oh shit!" was all I could manage as his cock, coated in my own juices, slowly disappeared into my asshole. Once he was buried to the hilt, he reached around and started fingering my pussy. I quickly let go of all resistance as Jake began pumping in and out while grinding his hips into me as he bottomed out. His rhythm picked up and soon he was slamming my ass as hard as he had my pussy. His fingers worked their magic on my clit as my orgasm brought stars to my eyes. "Fuck!! I'm cummmmmmiiingggg!!" I screamed as he slammed me several more times before letting out a deep groan and unleashing a torrid of sperm into my virgin asshole. I could feel the hotness of his load deep inside me as he emptied his balls while collapsing onto my back.

"Now that was a great fuck!" he proclaimed as the rest of the gang cheered and clapped for the show.