Another Day Another Dollar

"Claire! I've got a special assignment for you!"

I walked into my boss' office. Joanne was arranging some papers on her desk. Due to the warm weather outside, she had opened a window, and now the wind was messing up her papers. Finally she placed a large blue jelly dildo on top of them as a paperweight.

"As I was saying," she says. "I've got a special assignment for you. A guy just called. He's arranging a birthday party for his baby brother, and he wants to hire a girl to party with four guys."

"Only one?" I said. "As in a gang bang?"

"You're up for it?" she asked. "It's four times the rate..."

"OK, what the hell," I said. "I'll do it."

"Here's the address," said my boss, and handed me a post-it. "And don't forget to dress up! You're going to a birthday party, you know!"

* * * * * * * * * *

I straightened my polka-dot dress and arranged my hair to fall over my shoulders, and then I rang the doorbell for room number 14. The door opened, and a tall blond guy smiled at me. There was some music in the background. Apparently, they had already started.

"You're from the agency?" he asked.

"That's right," I said. "I'm Claire."

"Come in, Claire!" he said, and made a gesture with his arm.

I walked into the room, and saw 3 guys sitting in armchairs around a table loaded with bottles, snacks, and half-eaten pizzas.

"OK, everybody," said the blond guy. "This is Claire!"

"Hi, Claire!" the guys shouted, grinning at me.

"Hello, boys," I smiled.

"Claire is here to party with us, aren't ya, Claire?" said Blondie.

"I sure am!" I said, and put my handbag on the floor. "So...who are you guys?"

"I'm Mark," said the talkative blonde next to me. "This is my brother Kyle, that's our cousin Robert, and that's our best friend, Alan."

They all shook hands with me, which gave me the opportunity to examine them up close. Kyle was very young, slim and petite and rather boyish. He was as dark as his brother was light. Robert was on the heavy side, and had red hair and glasses. Alan had naughty green eyes, brown hair, and a toned body under his T-shirt. Mark was handsome, like a prince in a fairy tale.

"We're celebrating my brother Kyle's 18th birthday tonight, said Mark.

"Happy birthday, Kyle!" I said, and kissed him.

He raised his eyebrows, but responded willingly when I extended the kiss to be a French one. I could tell that he was inexperienced, but he was awfully cute. He stared at me when I pulled away.

"See, Kyle, this is your birthday present!" said Mark. "We all chipped in. Claire here is gonna take your cherry tonight!"

"What?" said Kyle.

Robert and Alan cheered.

"You... you hired... a..?"

Kyle blushed and stuttered.

"Might as well have it done by a pro," said Mark. "That way, you know it's gonna be good!"

"But..." said Kyle, looking terrified.

"Oh, don't scare the boy!" I said. "We're gonna have fun tonight, aren't we boys?"

"Hell, yeah!" said Alan.

"All night!" said Robert.

"How about we start with something easy?" I said. "A game? Strip poker?"

They were all up for it, and I took out my special deck of cards, the one that featured naked women. The guys whistled and made comments about the cards when I dealt them out. They were good at poker, they really were, but I've been playing this game since I was a kid, and I've had had loads of practice thanks to my job. I controlled the game from start, manipulated it so that within 20 minutes, I was in my underwear, and the guys were in their T-shirts and briefs. Nice and comfortable. Now we could start the real game. I lost another hand on purpose, and took off my bra. Kyle turned red, but didn't look away. I could tell that the others were getting a little... affected, as well. I wasted a nice hand in order to lose the next round, and now I was naked. Judging from Robert's face, he appreciated the fact that I was shaved. You little pervert, I thought.

"Oh, I seem to have lost all my clothes," I said, pouting. "What should I do now?"

"How about... you have to fulfil the winner's wish?" said Alan. "One wish, whatever he wants - but you have to do it?"

"OK," I said. "That sounds like fun."

So we played. And I immediately knew that they were setting Kyle up. Robert had nothing but a pair of fours, Mark had nothing at all, Alan failed to get a straight, and I had a pair of twos. Kyle was a clear winner, with his pairs of tens and aces.

"All right!" said Mark. "OK, then - Claire, you have to do anything Kyle asks you to do!"

"What do you want, Kyle?" I said.

"Ummmm... I don't know..." said Kyle, grinning awkwardly.

The others chanted "blowjob, blowjob!", but I could see that they were only making the poor kid even more embarrassed.

"Hold on!" I said, and hushed the others down. "How about Kyle and I go into the back room, where we can discuss things in private?"'

The guys agreed wholeheartedly, and Kyle looked relieved. He dried his sweaty hands on his T-shirt, and walked ahead of me. Everyone could see that he had a hard-on. I took my handbag and followed him into the bedroom. I closed the door, and sat down on the bed. Kyle stood by the foot of the bed, looking really nervous.

"Come over here," I said. "Sit here with me."

He did as he was told. Good boy.

"So, what do you want?" I asked.

"I don't know," he said.

"Would you like a kiss?" I said, leaning closer.

"Yeah," he said, and so I kissed him.

He was good at that. He even dared to put his arms around me. I slid my hand under his T-shirt and caressed his lean, hairless torso. I took one of his hands and moved it up to my breasts. I made him cup his hand around my left one. He broke our kiss and stared at his hand.

"Do you like it?" I said.

"Yeah," he mumbled.

He moved his hand, and bent down, leaned his head against my chest, and kissed my breast. He kissed it carefully, as if he was touching some religious relic. Then he moved his head a little and kissed my nipple. He licked over it, as if to try the taste of it, then he sucked on it like a baby. I pulled my hand through his dark hair, and held him tenderly with the other arm. I was going to turn this sweet boy into a man. And I was going to go slow. He deserved that. He played with my nipples, experimented with them, tried to see which would make them harden the fastest; the left, that was being sucked, or the right, which was being licked.

"You're a natural," I purred. "You make me feel so good..."

"Really?" he said, and looked at me. "You're not just saying that?"

"Is this proof enough for you?" I said, and led one of his hands down to my pussy. "Do you feel how wet I am?"

"Yeah!" he breathed, and put a finger inside my pussy. "All wet..."

I put my hand over his hard-on, and touched it through his briefs.

"Do you know what I'd like right now?" I whispered. "To give you a blowjob!"

He grinned shyly, and pulled off his briefs and T-shirt.

"Mmmmm..." I said, and kneeled on the floor in front of him. "What a nice dick!"

"Think so?" he laughed, and I could hear the question of every virgin guy in that laugh: "It's not too small, is it?"

"You got a nice, hard, mighty dick," I said. "Let me touch it - ooooh, yeah, it's hard as stone! Come here; let me have a taste of that!"

And I took his average-sized dick in my mouth, made it all wet and slippery, and sucked on it as I bobbed my head up and down, slowly, teasing. Kyle winced, and lay down on the bed. He looked up when I deep-throated him, and he moaned, closed his eyes, and fell back down on the bed. His hands plucked restlessly on the bedspread, and every now and then, he bucked upwards into my mouth, moaning. This cherry was ripe for picking.

"I'm gonna show you a little trick," I said, and picked up my handbag.

He looked at me, curious, as I got a condom out of my bag. I took it out of the wrapper and put it in my mouth, moving my jaws as if it was a chewing-gum. I went back to his crotch, and sucked him some more, then deep-throated him again - and when I came back up for air, the condom was rolled onto his dick, all the way to the root.

"Ta-da!" I smiled.

"Whow!" he said, impressed with my little trick.

I got on the bed, lied back, and parted my legs.

"Come here, stud!" I said. "Let's make a man out of you!"

He laughed nervously, but went down on top of me, and I took his dick and steered it right for him.

"Push it inside me, baby!" I said.

He shoved it into me, and moaned as he got in. He didn't need any more instructions; his male instincts were quite enough. All this shy boy needed was encouragement, and I whispered it into his ear, between breathing and moaning.

"Yeah, that's it, baby! Oh, man, you're good! Yeah, just like that! Aaah, that feels so good! Give it to me, Kyle!"

And he thrust inside me, too caught up in the sweet miracle of getting his first fuck to really think about me. His lips moved fast, his hands squeezed my breasts as if they had been handles, and soon he winced, and tensed up, lying perfectly still in my arms, his face contorted, as he came inside his first woman. The eighteen year old boy had become a man.

We were both startled by applause, and when we looked up, the other three were standing in the doorway, watching us.

"Nice show!" said Mark.

"Get out of here!" said Kyle, blushing.

"Oh, come on, don't be greedy!" said Alan. "You had your fun, now it's our turn!"

They walked into the room, taking off their clothes. Kyle sat up, took the dirty condom off, and left the room to get rid of it. I smiled at the other guys. Robert was indeed chubby, and his dick was thin and not very long. Mark had a curved dick, and Alan was well-endowed.

"Having fun Claire?" said Mark.

"Yes," I said. "And from the look of things, the fun has just started!"

"You better believe it!" said Mark, and sat down.

He frenched me, and put my hand on top of his hard dick. I jerked him off, and Alan got on the bed behind me. He kissed my neck and shoulders, and put his hands on my breasts from behind, played with my nipples. Robert tore my hand away from Mark's lips, and pushed his dick against my lips. I held his dick steady with one hand, sucked it, and jerked Mark off with my other hand. Alan moved his attention from my breasts to my ass, kneading it, his dick hitting my back.

"I like smooth, clean-shaven pussies," said Robert. "Makes it nicer to eat them out. You like being licked, Claire?"

"Uh-huh," I got out, my mouth full of his dick.

"Lie back," said Alan, and gently pulled me down on my back.

Robert pushed my legs further apart, parted my inner lips with his fat fingers, and licked from my pussy up to my clit; put one finger into my pussy and finger fucked me while he sucked on my clit. He may not be all that hot to look at, but man, could he eat a pussy! I moaned, not for show, but for real, and tossed my head back.

"Like that?" said Mark.

"Yes!" I panted. "God, yes!"

Alan straddled my chest, pressed my breasts together, and pushed his cock between them, fucked the cleft between my breasts. Mark felt left out. He moved over to my face, got on all fours over my head, and dipped his dangling cock into my mouth. It probably wasn't very comfortable, but at least he got to fuck my mouth. I relaxed the muscles in my throat, breathed through my nose, and allowed him to push his cock all the way down my throat. Robert moved his finger out of my pussy, and pressed it into my ass. I could feel a little sting, but he was doubling his efforts on my clit at the same time, and I groaned as my orgasm made me shiver.

"You like it in the ass, Claire?" asked Robert.

Mark pulled out, so I could speak properly.

"Why not?" I said. "I do everything."

"Come here," said Alan, and lied down on his back on the bed, pulling me up over his crotch.

"No glove, no love, baby!" I said, and poured my entire condom supply on the bed.

He picked out one of them, got it on quicker than I've ever seen a man do it before, and then lifted me up on his cock. He was so horny he was trembling. I sank down on his big cock, rose up, and sank down.

"No!" said Robert. "You just stand still!"

He got "dressed", too, and I heard him spit. His saliva landed on my anus, and then he pressed his dick inside my ass. I thanked God it was so small. A dick the same size as Alan's would have torn me apart! I stood still, on my hands and knees, and Alan bucked his hips to fuck me from underneath, while Robert fucked my ass. They had to work a little to get synchronized, and then they got the hang of it, and moved in and out of me, filling me up, stretching me up. Alan played with my nipples the whole time, and Robert pinched my ass cheeks, and slapped my ass now and then. He seemed to enjoy causing me a little pain. I looked up at Mark, and licked my lips invitingly.

"Later," he said. "You got a sweet mouth, but I'm waiting for my turn at your pussy!"

"It's a great pussy!" Alan groaned. "Fuck! So tight! So wet!"

"You must like your job, huh, Claire?" said Robert.

"Right now, I LOVE it!" I moaned.

Mark jerked off while he watched Alan and Robert fuck me. I heard quiet footsteps, and knew that Kyle had come back to watch. I wondered what he thought of the scene.

"Fuck, I'm coming!" said Robert, and gave me five hard, fast strokes, before he pulled out, panting.

With him out of my ass, I was free to ride Alan at my own pace. I bounced up and down on him, milked him with my muscles, and pretty soon, he too grunted, and arched up, into me - and then he fell back, all spent.

"Come here!" said Mark, and gestured for me to get on my back.

I got in position while he suited himself up, and then he entered me as well. I looked over his shoulder, and saw Kyle stand in the doorway, jerking off while watching his brother fuck me. He looked like he wanted a second go. Ah, well, I could do that, it was the guy's birthday, after all. Then I forgot all about Kyle, and enjoyed Mark's curved cock, that was just made for hitting a woman's G-spot. I came once, twice, three times, before Mark pulled out, tore the condom off, and shot sperm all over me.

"Time for your milk bath, your highness!" Alan joked.

I laughed. Kyle walked up to the bed, working his meat frenetically, and reached over to pick up a condom.

"Look and see who got himself a new hobby!" Mark laughed.

"I was wondering if... if it would be allright if I..." Kyle stammered.

"What, Kyle?" I said.

"What Robert did," said Kyle.

He had just lost his virginity, and now he wanted his first anal sex. This guy was advancing quickly!

"Sure, Kyle," I said, smiling sweetly. "Come here!"

I got on all four, and Kyle got the condom on, and put his dick against my anus. I jerked backwards, pressing him into my ass. Kyle took hold of my hips, and started pounding me. The others watched, jerking off, but they seemed too tired to actually go again.

"It's much tighter than a pussy!" Kyle said, slightly out of breath. "It's so tight it almost hurts!"

"Come on, Kyle!"

"Give it to her, man!"

"Fuck her ass, Kyle! Make her come!"

The others cheered him on. I moved my hand over my clit, and rubbed it. Kyle fucked my ass, and I slid my fingers over the wet, slippery button. Closer, now... Closer... I moaned a little extra when I came, and Kyle shouted when he came. The others cheered and whistled, and when Kyle pulled out of me, Mark even gave him a high-five.

"So, did you like your birthday present, Kyle?" said Mark.

"Yeah," said Kyle. "It was great. Fucking awesome!"