Pretty Baby Ch. 01

I crawled up atop him, straddling his hips, rubbing my pussy against his half-hard dick. It was the closest a penis had ever come to my virgin hole, but I trusted Gary not to take advantage of the situation.

"Thanks, Gary," I said, feeling heady from both the alcohol and semen I had consumed.

He smiled up at me, gently massaging my breasts and tilting his head to kiss and lick them. "You're welcome," he said. "I knew you'd enjoy it."

I breathed out, surrounded, saturated, with the aroma and flavor of sperm, and kissed his forehead. I was still turned on. I could have kept sucking the guys all night, but knew they wouldn't have been able to handle it. Besides that, my jaw was sore.

"I've got something for you," said Gary.

My eyes lit up. "Yeah?"

He chuckled, indicated his jacket hanging off one of the chairs. "Go get it."

I scrambled off him, excited, and rummaged through the jacket. I found a thick white envelope inside, and took it out. I looked to Gary expectantly. He nodded with a smile.

"Goody!" I exclaimed, jumping back atop him, making him grunt and the bed bounce. I opened the envelope, finding a stack of twenties inside. I counted the money quickly, grinning as I realized I held four hundred dollars in my hands. Not bad for three hours' work, I thought. It was more than I made in a week at the restaurant.

"There's something else," he said.

I frowned, and dug into the envelope. Something bulged against the side, and I pulled it out.

A ring. Gold, lined with tiny diamonds, with a blue butterfly centerpiece. I swooned, and my eyes watered. "Oh, Gary," I sighed, dripping tears down my cheeks.

He smiled, smoothing his hands up and down my body. "Call it a friendship ring," he said. "Go ahead, put it on. I think I got the size right."

I slipped the ring down my finger. It fit perfectly. I wiggled my fingers, looking upon the jewelry, then bent over and kissed Gary deeply. He responded immediately, kissing me back, wrapping his arms around me.

My body undulated atop his, and I felt his cock stiffen. Panting and moaning into his mouth, I slid my hand down between us, finding his dick with my fingers. I tilted it up, rubbing the head against my damp labia. Gary groaned.

"Oh, Alyssa," he sighed, grabbing my ass with one hand, the other pushing up through the hair on the back of my head.

"Do it, Gary," I panted. "F-fuck me . . . ."

I arched my back, rolled my hips, feeling my pussy spread open. The head of Gary's stiff prick pushed between my folds, sliding inside . . . .

"Oh, God!" I cried out, my virgin tunnel immediately clamping down on the intruder. I worked it a little, wincing, then sighing as the head popped inside. "Oh, sweet baby Jesus . . . ."

Never had I felt anything like this! Fingers and tongues were one thing, but this was acock! And it was pushing up inside me,penetratingme for the first time, probing deeper and deeper until . . . .

I yelped as I felt the barrier inside me stretched by Gary's penis, and pulled up. I stared down at his face, saw the mirror of my own shock and reluctance.

"You're not ready," he said.

I sighed, and cried again. "Oh, God, I-I'm s-s-sorry . . . ."

But Gary just smiled and slipped out of me. I moaned as my pussy was emptied, his slick cock sliding out and slapping wetly to his abdomen. Gary pulled me down and kissed me again. "It's okay, baby," he whispered. "You'll know when you're ready."

I smiled upon him through my tears. "I'm glad you're my friend, Gary," I said.

"I am, too," he said, and held me close.

***

Every Sunday evening, I 'entertained' Gary's employees, sucking and fisting their dicks until I received mouthful after delicious mouthful of creamy sperm. Maybe they weren't the most attractive men in the world, but they served up generous amounts of cock cream for my hungry mouth, and treated me like a princess on parade.

I would dance naked for them, give lap dances as they groped and fondled me, and masturbate before their eyes as a prelude to a wild round of cocksucking. Some of them licked and fingered me – always being careful, of course, not to tear my hymen – and such men received extra special attention in return.

I always went home satisfied and full, with Gary dropping me off on my doorstep and giving me a sweet kiss good night. We didn't talk about how close we had come to making love for the first time.

The holidays brought an abatement to our blow-bang weekends. I spent Christmas with my parents, and Gary was out of town with his wife and kids, visiting family 'back east.' I satisfied my carnal needs with the usual boys in the mall, but I missed the thrill of having multiple dicks at my disposal. I couldn't wait for Gary to come back.

***

My cell phone rang shrilly on New Year's day, rousing me from an alcoholic stupor. I had gone to a party the night before, hosted by Katie, a girl from work, and had ended up doing at least two, maybe three guys in the bathroom by the time the fireworks started. I barely remembered the blow jobs, clouded as they were by the fog of too much alcohol.

"Hullo," I grumbled.

"Alyssa, it's Gary."

I became awake instantly, even if I was still drunk. "Gary?" I slurred.

He chuckled. "Good party?" he asked.

I clutched my head. "Ffffuck . . . I think I got a hangover."

"You're not the only one."

"Where are you?"

"Still home," he said, referring to 'back east.' "I miss you. You okay?"

I smiled. Gary was so sweet. Even if he was married, he was a better boyfriend than I could hope for. "I'm fine," I said. "I didn't do anything crazy, if that's what you're asking. I'm still cherry . . . I think." I reached down, between my legs, and poked a finger in my hole, feeling around. "Yup. Still cherry."

"That's not why I called," he said. "I just wanted to say 'happy new year.'"

I imagined kissing him. "Gary."

"Yeah?"

"Do you wanna be my first?"

I heard him breathe in. "Is that what you want?"

I sighed. "Well . . . you're kind'a like my boyfriend, right? Even if you are married."

"Alyssa . . . we talked about this."

"No, we didn't."

"Well, not aboutthis, but . . . you know what kind of relationship we have."

"Then why are you calling me at . . . eight-thirty-six on New Year's Day?"

". . . . ."

"Well? Do you or don't you?"

"It's not that simple, Alyssa—"

"Sure it is. Just come over, pop my cherry, it'll hurt a little bit but I'll be okay—"

"And then what?"

I frowned. "What do you mean?"

"You can't fall in love with me, Alyssa."

"I'm not—" I began, then stopped myself. I became defensive. "Oh, right. I forgot. I'm just yourfriend. You're favoritewhore."

"Alyssa . . . ."

"No, hey, it's all right. No big deal, right? You just let me know when you're back in town, so we can set up some more blow bangs. Happy fucking new year." I snapped my phone closed, then fell back into my silk pillows and cried myself back to sleep.

***

I heard the knock at my door a couple of days later, as I was getting ready for work. I was starting to hate my job. I worked too much and didn't have enough time to study. On top of that, I was being teased by guys at work about my New Year's Eve antics.

If only they knew the truth . . . .

I had just gotten out of the shower and answered the door clad in only a towel, my hair wet and slicked back. Something blocked the peep hole of my door, so I couldn't see who was outside. I opened the door anyway.

The first thing I saw was a big bushel of red roses. Then a pint bottle of strawberry vodka. Then Gary's sheepishly smiling face.

I couldn't help but smile back. "Damn it, Gary," I said, and snatched the bottle from his hand. I turned into the apartment, Gary following behind. He closed and latched the door.

"Peace offering?" he said.

I chuckled, and opened my towel, flashing him. "Piece offering?"

He laughed, and went into my kitchen, looking for something to put the roses in. I retied my towel and sat down on the couch, unscrewing the cap on the pint. I sighed at the taste and warmth of the vodka. I looked for my cigarettes, lit one.

Gary came back, the roses sprouting out of one of the big schooner glasses I kept in the cupboard. "Finally buying your own smokes, huh?"

I shrugged. "Well, you haven't been around to bum off of," I said.

He sat down beside me. "Are you mad that I went away for the holidays?" he asked. "You know I have a wife and family."

I sighed. "I know, Gary. And no, I'm not mad at you. I just . . . ." I couldn't figure out what I wanted to say.

He touched my arm, watching me as I drank and smoked. "Do you really want me to be your first?"

I took a deep breath, let it out heavily. I stared at my blank television. "No."

Gary didn't say anything. I got the impression he was a little disappointed. I knew guys were turned on by the idea of taking a virgin, and I guess, since my comment two days before, Gary had been thinking about it.

"I know this girl, in one of my classes," I said as Gary took out his own pack of cigarettes and lit up. "Julie. She's real cute, about my age. Actually, I think she just turned nineteen. Anyway, we're not really that close, but we hang out sometimes in the Quad. I don't know how we got around to it . . . we were talking about guys, I guess . . . but, she started telling me about her first time."

I tapped my cigarette over my new crystal ashtray (courtesy of Manny at the Waterford store and his surprisingly large penis), took another swig from the bottle. Gary was silent as he listened to me. "She didn't, like, go into detail or anything like that, but she was telling me how sweet her boyfriend was at the time, how it hurt at first but then felt so good . . . a couple weeks later, he dumped her. Just like that."

Gary sighed. "Men can be real assholes," he said.

I laughed sharply, tilted the bottle to my lips again. I was starting to feel a little buzz. I still didn't look at Gary, just continued with my monologue: "Ever since then, I've been thinking about it. About what my first time will be like . . . and about what'll happen after."

"And?"

I took a drag of my cigarette, another slug from the bottle. "Every girl I know, the story's always the same. They never stay with the guy who popped them. So, when you think about it, it doesn't really matter who I do it with." I finally looked to Gary. "Right?"

His eyes studied my face a moment. "Do you really think that?"

I nodded. "But you know what's funny?"

"What."

"I don't want it to be you," I said, making Gary frown. I smiled, touched his face. He had a little stubble. "I know that doesn't make sense, but it was something you said."

He nodded in understanding. "About . . . falling in love," he said.

"I really like you, Gary," I said earnestly, the alcohol loosening my inhibitions. "And I just know, if we did it, I'd start feeling . . ." I looked down. "I think I probably would fall in love with you. Even more than I already have."

"Oh, baby," he said tenderly, wrapping his arms around me. I snuggled close to him, breathing in his scent. God, he smelled so good. I closed my eyes, murmuring softly, wanting to just lay down with him and pull off our clothes, feel him pushing inside me. Iwantedthat. But I knew it would be the wrong thing to do.

"I don't know what to say, Alyssa," Gary whispered, petting my hair. "Like I said, I do love you, but we'll never—"

"I know," I said, pulling away. I gave him a little smile, letting him know I wasn't upset.

Gary just nodded, watching me as I drank again. He laughed softly. "Hey, don't go getting drunk."

I smiled mischievously. "Why not? Afraid I'm gonna jump you?"

He chuckled. "Actually, I'm hoping you will."

I laughed, sipped again. 'Casually,' I pulled on my towel and let it fall around my butt, exposing my body. Gary breathed in.

"Damn, Alyssa, you really have an incredible body," he said, looking upon me.

I smiled, spread my legs. "Look. I trimmed." Gary's eyes followed my hands as I touched my pussy. My lips were shaved smooth, and I had just a little strip of nearly invisible blonde pubes above my clitoris.

Gary reached over and touched me, tickling the edges of my pubic hair. "Very nice. No stubble," he commented.

I giggled and cupped his cheek. "Unlike you."

He blushed a little, keeping his hand on my puss. I squirmed a little, encouraging him to finger me. He did, sliding his middle finger slowly inside my tunnel. He kept it there, not moving it, just letting me enjoy the sensation. I bit my lip, closing my eyes a moment as I felt his finger curling a little bit inside me, massaging my snug, wet walls. I took a last pull from my cigarette, then stubbed it out.

"Get my phone, Gary," I said in a soft voice. "It's on the counter."

Gary looked, saw my phone, then smiled back at me. Gently, he eased his finger from inside me and sucked it as he got up. The alcohol was making me buzz, increasing my libido. I took another swig from the bottle.

Gary brought me my cell, and unbuckled his pants as he remained standing beside me. I grinned, hitting the buttons, dialing work.

"Hey, Sandy," I said, making my voice sound scratchy. "It's Alyssa. Can I talk to one of the managers?" I faked a cough.

"Yeah, sure. Hold on a sec."

I listened to bad Muzak as I watched Gary get undressed. He seemed to be a little trimmer around the middle. His penis was hard and shiny as it was revealed. Soon, he stood completely nude before me. I giggled softly when I noticed he had shaved his balls. I reached out and cupped the smooth, hanging orbs with my hand. Gary smiled upon me and petted my hair.

"This is Juan, how can I help you?"

"Juan," I said into the phone, and coughed again. "We got an on-call for tonight?"

"Not feeling well, Alyssa?"

"Not really. I think I'm getting something." I tickled Gary's balls as I spoke. "I think I'm getting it pretty hard."

"Don't worry, sweetie," my manager said. He always called me 'sweetie.' "We've got too many on the floor tonight anyway. You need someone to bring you anything?"

"Nah, I'll be okay," I said, moving my hand up to stroke Gary's cock. A thick, clear bubble formed at the tip. "I've got some juice. I'll make sure to drink it all."

"Well, if you need something, let us know, okay?"

"I will. Thanks, Juan." I snapped my phone closed, and Gary laughed.

"Feeling sick, baby?" asked Gary, pulling my head toward him.

"Uh-huh," I said, parting my lips as I looked up at his face. "I need some medicine. Something thick and sweet to coat my throat."

Gary moaned as I started sucking him. "Mmm, baby, you're gonna get all the medicine you want . . . ."

***

"So, I got an idea," I said half an hour later, as Gary recovered on the couch. I had swallowed most of his cum, but a little had oozed out from the corner of my mouth and dripped down my chin. I didn't bother wiping it away as I lit another cigarette and sipped from the bottle of strawberry vodka. I glanced to the two twenties Gary had left on the table. He was getting a reduced rate these days.

"What's that, babe?" he asked, stroking my naked back.

"Well, I've been thinking about it. About doing it," I said.

"And?"

"And . . . I don't wanna worry about whether or not the guy's gonna stick around. I don't wanna fall in love with him. I want it to be someone I'll probably never see again."

Gary frowned. "You sure about this?"

I nodded as I took another sip of the vodka. "Think about it from my point of view. If I never see the guy again, I won't fall in love with him. I'll just have this wonderful memory of my first time, and that'll be that."

"How are you going to make sure it'll be wonderful?" he asked.

I smiled knowingly. "I'm not.Youare."

Gary frowned. "Huh?"

I shifted on the couch, facing him. "Okay, this is what I'm thinking: You know a lot of men, right?"

He nodded slowly. "Right . . . ."

"And, unless I'm wrong, guys in your field make bank. I mean, you make a lot of money, right?"

Gary shrugged. "I do pretty well," he said.

I smiled slowly, the idea in my head making me excited. "I wanna have an auction."

He blinked. "A what?"

"An auction," I repeated. "Highest bidder gets to pop me."

Gary sat up, staring at me with an alarmed look. "Whoa, Alyssa, hold on a sec—"

"No, I'm serious," I said vehemently. "I wanna do it this way. You let all the guys you work with know that my virginity is for sale, and we'll see who's got the deepest pockets."

Gary didn't seem too thrilled by the idea. "Alyssa, think about this. You can't just . . .sellyour virginity."

"Why not?" I asked in that simple way.

"You just . . . can't. I mean—"

"Look," I said. "Every girl wants her first time to be special. I'm no different. I'm going to remember the first time I have sex for the rest of my life, so I wanna do it right." I started ticking off on my fingers. "I want champagne, roses, a nice hotel suite, a limo ride . . . and dinner. And then I'll do anything the guy wants, all night long."

Gary stared at me, reading my face. "You're serious."

I nodded firmly. "As a heart attack."

He looked dumbfounded. "And . . . you want me to set it up."

"I'll give you twenty-five percent," I said.

Gary looked startled. "Well . . . wouldn't that make me . . . ."

I giggled. "My pimp? Yup."

Gary looked away, taking up his cigarettes. "I don't know."

I snuggled close to him, licked and kissed his ear. "You can be my second," I whispered suggestively.

Gary shuddered. His cock twitched. I reached down and stroked it, caressing his smooth balls with my fingertips.

"I-I'll think about it," he said.

I kissed my way down his body. "You do that," I said, and submerged his dick in my mouth, loving the feeling as it grew hard against my tongue. "Mmmm . . . ."

. . . to be continued . . .