It was one of the stranger requests I’d ever taken, and one of the most interesting.I love it when my friends think of me! Let me explain: I went to college and roomed with a guy, Richie, from Chicago. His grand parents were, (and here, I have to swear to God, is the truth) a gypsy, a trapeze artist, a gangster and an Kansas farm girl. Through his gangster grandfather Richie inherited a whore house. He was rather embarrassed about owning it, but the money that he made was unbelievable. It allowed him to attend our ‘prestigious’ ivy league college.
Which brings me to the here and now. I am sitting in a cheap hotel waiting with a friend of mine, for a girl to show up. Richie explained that this particular girl was a ‘newbie’ and although she’d been working for him for a few months, and had gotten into the swing of things, there were a few things she wouldn’t do for the customers. That’s where I came in. In school I had a rep for being able to get any girl I wanted and for knowing how far to push them. He wanted me to ‘expand the horizons’ for this particular girl. I was more than willing. Even for a slut like this. He’d pay me and give me money for the girl. She was not to know it was his idea. All he told her was that we were old college buddies and she was to show us a good time.
There was a knock at the flimsy wooden door. Greg went to the bathroom and quietly pulled the door almost closed. I walked across the seedy green carpet and opened the door. There stood a slim, young girl with long, straight brown hair. She was wearing a leather ultra mini skirt with zippers that ran up each hip from the hem to the waist. She’d tied a button-down shirt up under her breasts, with most of the buttons unbuttoned, giving me a nice view of her tits spilling up and out. On her feet were a pair of 3 inch platform sandals.
Without saying a word I turned and walked back to the lumpy, low sofa and sat down. She came in wobbling slightly on her shoes. Standing in front of me, she timidly asked “Got my money?” She looked a bit nervous and her eyes kept moving around the room.
I pointed to the dresser where $100.00 dollars lay. “You know there are two of us, right?” I asked her, not really expecting a reply. She slowly nodded. As far as she knew, we were going to be taking turns. I licked my lips, she was so young and innocent looking, and I was going to enjoy this so much. I could hardly wait. “My friend Greg will join us soon,” I told her. “Come here”.
She wobbled up closer to me and stood directly in front of me. I took perverse pleasure in opening my legs and leaning back to admire her. Her chest was rising and falling with each shallow breath and her nipples were easy to see straining through the thin white top. My voice came across softly but brooked no argument, “Lace your fingers behind your head, and keep them there". Her hands went up and her young tits pressed harder against her top, threatening to fall out at any minute. The flat skin of her belly went smoothly from the bottom of her shirt under the waistband of her mini and the skirt rose enough to let a peek of red nylon covered crotch peek out. “Turn around,” I ordered almost harshly, and she turned slowly. I watched the firm round globes of her ass come into view and I had to suck in my breath. My ultimate goal! And they were perfect, so far.
I sat forward as she completed her turn and I placed my hands on the inside of her knees encouraging her to open them wider. My eyes held hers as my hands slid up her slim legs and moved closer to her pussy. I could feel the heat coming off of her and I thought I smelled the musk of wet pussy too. Finally, my questing fingers hit silky nylon and I was right she was soaked! I reached out for the zipper on the nearest hip... and the rasp of metal on metal filled the room as I peeled the zip up. Her panties turned out to be a thong and her hips, as smooth as her belly, came into view.
Silently, Greg came out of the bathroom and as my fingers slipped back to her crotch and began to rub her, he pressed himself up behind her. The little whore squeaked and jumped as he made contact, and her hands unlaced and began to come down. “Oh no,” Greg said and quickly grabbed at them and moved them up. He reached under them and in front of her and wrapped his big meaty fingers around her thinly covered tits. He began to tease the already hardened nipples. My questing fingers had pushed her thin thong to the side and I was rubbing her stiffened clit.
“Greg, we are going to have so much fun with this slut. Her pussy is soaked” I managed to blurt out.
She began to moan “Oh god yes, rub my pussy, play with me” she begged and she leaned back against Greg. Her hips were pushing forward trying to get more of my fingers. Greg untied the knot of her blouse and her tits spilled free. Greg latched onto her nipples with his fingers and began to tug and pull at them, as they stiffened up to little buds.
‘MMMMmmmm” she moaned. Grabbing at them, he mashed them together and squeezed them causing her to cry out and arch her back tighter against him, pushing her pelvis closer into my face... Her juices were running over my fingers and lubing them up. Greg released her tits and slid to her side, putting her arm up and around his shoulders. His lips dove down onto her perky hard nipple and he sucked it into his mouth. He gave me a little wink and I drove two pussy slickened fingers into her snatch as he bit down on her nipple.
She let out a little scream of pleasure and began to rock her hips on my fingers. Greg was biting down on her tight peak, nipping and tugging at it and then wrapping his hand around the full globes and lifting and pulling her whole breast closer to his mouth. His other hand was sliding across her back, up and down her spine and teasing the top of her ass crack. I pulled my thrusting fingers from her sopping pussy and moved from the sofa.I quickly stripped off my clothes and made short work of removing the remaining clothing stuck to her, except for those ridiculous high heels. I sat back down again and began to stroke my cock. As I watched as she began to encourage Greg to get her off.
“Come on honey,” she panted, “ Lick my tits. Your friend made my pussy so wet. Do you want to touch me?” Greg placed his hands, one in front and one on her back, and slid them down her body. His fingers in front obviously headed for her pussy the others headed for her ass. His one hand slipped through her small thatch of pubic hair and the other... I was watching her face and I knew as soon as he’d gotten close to her virgin asshole. She began to twitch and shake her derriere as if in an effort to get free. She made a grimace and twisted out of his grip. For now he let her go.
“Oh no you don’t big boy,” she panted “ I’m saving that. But there are other things I will do for you.” And she began to sway and dance around the room. It looked a bit comical as there was no music. Then she reached down and flicked on the television set to a popular music video channel. We both watched for a while as the song crested and waned. We were standing around watching her dance when it suddenly struck me as funny we had a hooker to do with as we pleased and we were watching her dance?badly?
“Come here baby, come and suck my cock” I ordered and just like that she came in front of me and sank to her knees. Her hands went to my thighs, nails gently scraping them open wider. Greg stroked the front of his trousers, his cock making a magnificent bulge there. Her hands slid up my legs and around my 8 inches... she licked her lips as if dick were her favorite meal. Her tongue licked my head as if it were a lollipop and when it was slick with her saliva she pursed her lips and sucked me into her mouth as if I were slipping into her pussy. I watched as inch by inch my cock disappeared. She began to hum or moan I couldn’t tell which, and the vibrations were strumming through my cock. Greg meanwhile was removing his pants as fast as he possibly could. He stood behind her, and reaching down he grabbed a hold of her hips. I placed my hand on the back of her head and kept her talented, wet mouth on my cock as Greg lifted her to a standing position. He pushed her feet wide apart with his feet and his fingers dove into her pussy.
“Oh this little slut is so slick,” he said in amazement. Stepping back he began to pull off his Tee. Our little slut was watching him and I let up on her head so she could get a better view. Greg was down to his boxers and what a tent was rising from the front of them!! Her eyes got as big as saucers when he pulled them off and a fat, bumpy, 12 inch tool slapped against his belly! He stepped over to the door and locked it. I pulled her face back to my throbing tool.
“Do you like what you see, darling?” I asked. Greg has one of the fattest tools I’ve ever seen and he knew what to do with it. “Well, baby? Do you like it?” She could only moan in the affirmative as her mouth was once again wrapped around my cock. I noticed little streams of saliva running from the corners of her mouth down the sides of my tool. “Good. I’m glad you like it, because, baby, we’re gonna slide that tool up your ass!”
She spit my cock out and screeched “Oh no you’re not! That wasn't part of our deal!"
She tried to back away but I quickly wrapped a handful of hair between my fingers and pulled her face to my cock again.
“Oh yeah baby. We are going to stuff that perky little butt of yours and all the crying or pleading you can do will not stop us!” Greg returned to his spot behind our girl and as I muffled her with my dick he began to finger her incredibly wet pussy, paying special attention to her clit. He was pinching and pulling on her delicate little bud and talking up a storm.
“Oh, girl, you should see how your pussy clenches around my fingers. I have two in your pussy now and they are so wet! How about another?” He must have pushed a third finger into her because she began to squeal on my cock. Her ass was shifting and shaking around, but Greg gave her a sharp smack across an ass cheek and she stilled.
Tears slipped out of her eyes as she heard him say “Lube these fingers well kiddo because I am going to slip one into your ass soon.” He winked at me and said “Hold her buddy. She’s gonna shake now.” She indeed did begin to shake and shimmy her butt. I was worried she might hurt me so I threaded another hand into her long brown locks and pulled her head off my raging hard tool.
“ Hold still baby” Greg said, and then he winked at me. “Feel that? That is my finger taking your pussy juice and running it around your little brown ass. Can you feel me? I’m pressing into your hot little hole.... Push back and it will feel better. Or just Let..... me.... in!” I watched her eyes as his fingers slipped past the tight little ring of her ass and if her eyes got big before, they were huge now!
“ Oh please NO!” She begged. She looked at him over her shoulder and then at me “Oh God PLEASE NO!” tears were running down her face and I tried to calm her. “ Honey” I said in a calm voice “ Just close your eyes and let him.” I began to push her back towards the fingers.
“Please, I can’t take it. I’ve never had anyone touch me there. OH GOD Please STOP!” I was trying to make eye contact and calm her when all of a sudden she stopped squealing. Looking back I see Greg’s face buried between her cheeks. I wrapped her hair under her chin and forced her eyes to mine. “Baby, doesn’t that feel good? Can you feel that tongue rimming that adorable little puckered hole you have? Come on baby, suck my cock some more. It’ll be alright,” I said as I guided her head back down to my waiting cock.
Greg stood up and I felt her go still, he wrapped his big fingers around the shaft of his cock and began to run it up and down her by-now gushing slit. “You want this baby, I know you do!” said Greg and he slid the head of his tool to her sopping pussy entrance. She moaned as the head of his thick tool spread her cunt lips wide. Her pussy was stretched as wide and as tight as I thought it would go and he was still pushing in! She began rolling her hips from side to side to try and accommodate the fat intruder burying itself in her.
MMMMMmuuuffffffff, is what I heard, and who knows what she was saying, but Greg now had a hold of her hips and was forcing more and more of his shaft into her pussy. I had her face pushed hard against my curly hairs and was letting her up only to catch her breath. Greg was about half way in when she began to try in earnest to get away. Now she was flailing about with her hands and I caught one, Greg the other. Greg got a hold of both hands and pulled them behind her and used them as leverage to squeeze the remainder of his tool into her. Pulling on her wrists and forcing his dick in deeper and then letting up and pulling out a little.
“Aaahhh, getting better!” Greg practically shouted. “Her pussy is creaming around me. Listen girl, can you hear how sloppy wet your pussy is? Cum is running down to my balls and down your legs.” He reached under her somehow and came up with a finger full of wetness. “This is your cum baby, slick and wet.”
He took his wet digit and poked at her ass again. “Oh she’s going to want this! Look at that ass sucking in my finger,” he said loudly. “Take another finger,” and I can only assume he slipped another finger into her ass. She began to groan and this time I let her up enough to make out her words. “ I going to cum.” she said and then again in a louder voice, “ Oh GOD ... I’M.....GOING..... TO....... CCCUUUUUUMMMMMMMM!” Greg slammed his monster deep into her and the look of pleasure on his face was wild! He quickly withdrew from her pussy leaving his fingers pumping in her ass. She was crying and rocking back on just his fingers and yelling about cumming and how good it felt.
As she began to calm down he pulled his fingers out of her with a little plop and we let her stand up. Greg moved around to the sofa and sat down and we guided the now docile girl to his lap. “I want my cock back in there,” he stated and we guided her around to kneel on the edge of the sofa and straddle his hips. Grasping his shaft at the base, she pushed it towards her sopping hole. I was treated to the wonderful sight of his dick slowly disappearing into her. She put her arms onto his shoulders and began to rock on his cock. I looked at her puckered ass flashing up and down and couldn’t wait any longer. Teasing it with the tip of my finger caused her whole body to stiffen and stop moving.
“ Oh no. Please not my ass” she begged “ Oh God please don’t. I can’t do it. I can’t take a cock up my ass. Oh god, please... no one has ever...No NO”
We both began to reassure her she could, and I replaced my finger with my stiff slick meat. She began bucking and twisting again so Greg grabbed her by the shoulders and jammed her down on his tool and I slapped her ass again.
“Be still” I threatened in her ear and again she stiffened. “This will go easier if you just relax. And it will be even better if you push back a little against me. But, baby, either way I am going to fuck that lovely puckered hole of yours.” The view I had was perfect. I watched as the crown of my cock pushed against her tiny hole. It began to stretch and whiten. Greg had her impaled on him and was doing a great job of holding her still. Holding my tool around the base, I forced more into the tiny hole.
As the head finally slipped in she began to yell “ OH MY GOD! TAKE IT OUT! I CANT DO IT! OH GOD PLEASE STOP!” Greg reached up and slapped her teary face.
“Hush now, we are not going to stop. You can take it, and you will.” Greg had both of his hands wrapped around the hooker’s head and was talking calmly right to her. Then his hands slid down her neck across her chest. His hands circled around the outside of her boobs and then, moving to her nipples he began pinching and pulling at her hardened tips. The momentary pain distracted her from the stretching she was getting from me.
I was now working my shaft into her. My dick was drying out so I leaned forward and spit at her hole, soothing another inch inside. Relentlessly I pushed forwards and finally I was buried to my nuts. I gave Greg the ‘high sign’ and he began sawing in and out of her pussy. As I felt her relax I began to move slowly in her ass. A little back.... a little forward. A little more back a little more forcefully forward. Soon I was rocking in a rhythm with them. Greg begins to pant.... “ I told you, you would like this baby!” He says. He grabs at her face and brings it down close to his. “I’m going to cum in you.” and he slapped her ass for good measure. “Ride my cock. Take me deep inside you! Come on girl!” he yells, then he is bucking and thrusting for all he’s worth. It’s all I can do to stay inside her. Grabbing her shoulders roughly he jams her down on his rampaging cock and begins to pump cum into her pussy. I have buried my dick in her ass and at this point I feel as though I am just along for the ride! Slowly I feel a little room in the girl’s lovely ass and I realize his cock is slipping out of her.
I pulled her, not very gently I’m afraid, to stand on her feet and I forced her head down to the floor. ‘Now it’s just me darling,” I said and I begin to hammer my swollen cock in and out of her spread little asshole I can hear her begging... But I just don’t care anymore. I can feel my own cum rising and I’m sure she can feel my cock swell inside of her. She surprises me by yelling out “FUCK ME, I’m so dirty, I love your cock in my ass. Come on baby! Fuck my ass! Make me cum!”
That blew me over the edge and I began to cum, I pulled back to see great ropy streams of cum are shot from my dick into her gaping hole and onto her back. She reached behind her and rubs the cum around her sore stretched asshole and actually dips a finger into her ass.