Pretty Baby Ch. 02

I sighed with passion, gazing upon my favorite cock in the whole world. Gingerly, as if I was afraid to break the thing, I took it in my hands and lightly stroked it. I caressed his smooth balls, ran my hands along his upper thighs. My mouth watered in anticipation.

"Go ahead, Alyssa," he said in an impassioned voice, gently pushing me down. His cock stiffened and grew quickly under my ministrations, reaching its full length. I slid down his body, kissing him through his shirt, before gratefully taking his wonderful penis in my mouth.

"Ohhh, yes, Alyssa," he sighed, stroking my hair as I bobbed in his lap. "That's a good girl. Suck it nice and soft, baby. Suck it and get your reward."

I moaned and whimpered around his dick, lavishing it with all the attention and skill I had to give. I pushed Ian's delicious cock all the way down my throat, reveling in the feeling of taking him so deep. I held him there as long as I could, letting my esophageal muscles work on him. Ian gasped and massaged my scalp. I was, indeed, his 'good girl.'

When I felt that he was ready to cum, I slipped up and sucked hard on just the head while stroking the slick shaft with my hand. Ian barely grunted when he ejaculated, but I didn't need to hear shouts and cries to know he was enjoying the pleasure of cumming in my mouth. I sucked out every drop of his wonderful cream, nursed his prick as it softened. I kissed and licked it tenderly once he was spent, then sat up, keeping his load in my mouth.

I realized Ian had parked in the lot of a theater not far from my apartment. There were people outside the car, some of them trying to look in through the dark-tinted windows. I looked to Ian, smiling with his cream in my mouth. He produced a linen handkerchief, dabbed my lips.

"Let me see," he said.

Staring into his eyes, I opened my mouth and showed him his own swirling jism. Ian smiled, then gently closed my jaw.

"Don't swallow it, Alyssa," he said. "Not yet."

I just nodded, enjoying how kinky my man was. He tucked his penis away and zipped up, then opened the door. He came around and let me out, taking my hand as I stepped from the car. Keeping my lips pursed, Ian's heavenly load sloshing across my tongue, I held his hand as we walked across the parking lot. Eyes were upon us, wondering and curious. I felt immensely proud to be with Ian.

"Drama all right?" he asked me once we got to the window.

"Mm-hmm," I responded, unable to speak.

Ian purchased two tickets for us, then lead me inside to the concessions stand. "Would you like a soda?" he asked.

I just nodded and indicated the Diet Coke dispenser on the fountain.

"Snacks?"

I nodded again, and pointed to a bag of peanut M&Ms. Ian gave me an amused smile. It turned him on, I knew, that I still had his thick semen in my mouth. It turned me on, too. I loved the way it mixed with my saliva and changed in texture.

With our drinks and snacks, Ian and I headed to the theater. We passed dozens of people, and I recognized a few faces from class. They waved and said hello. I could only wave back. They gave me curious looks, checking out Ian. I could tell some of the girls were jealous.

Ian and I sat down and he held me as the previews began. As the theater grew dark, Ian slipped up my skirt and pushed my legs apart. I stiffened, startled at being so exposed. I didn't dare look around to see if anyone was watching. I just kept my eyes on Ian as he stroked my slick lips and the stiff button of my clitoris.

"Spit some of it out, Alyssa," Ian whispered in my ear. "Right on your pubis. Then you can swallow the rest."

I quivered at the kinky thought, and rolled up, positioning my face right above my pussy. I pushed out some of the fluid in my mouth, watching a long, thick glob of cum, glimmering in the light from the screen, ooze down toward my pussy. It broke about halfway down and splattered right on my clit. I swallowed the rest with a sigh, breathing out. I leaned back against Ian, keeping my legs spread for him.

"Oh, God, Ian," I sighed.

"You're a delightful woman, Alyssa," said Ian. "Go on, rub it in."

Eagerly, I massaged my pussy, smearing in Ian's cum, making my lips and pubic mound shine. My little strip of hair was dark and matted by the time I was done. My lips were puffy, my clitoris swollen and protruding. Ian moved my hand away, replacing it with his own.

All throughout the movie, Ian kept his hand on my pussy, stroking my lips, rubbing my clit, keeping my arousal constantly heightened. Now and then, people would pass in the aisle and do a double-take, seeing me with my legs so wantonly spread and an older man fingering me. They gasped and blushed. Their reactions turned me on even more.

I have no idea what the movie was about. I remember a few scenes, but the most important scene of all was happening between my legs. Ian finally made me cum after more than an hour of sweet torture, and I bit into his arm, muffling my gasps and moans as I spurted all over his hand. He kissed me lovingly, then lifted his hand and bade me to suck all my own cream off his fingers. I did so eagerly, glazing my lips with my fluid. Ian told me to leave them wet.

I never realized just how kinky one man could be, and how readily I accommodated him. I was conscious of the fact that I was the mistress, the 'other woman,' but that didn't stop me from being madly in love with this man. Anything he wanted me to do, I would, and I told him so.

"Do you mean that, Alyssa?" he asked as we headed back to his car.

I squeezed his hand. "Anything, Ian," I insisted. "I'll do anything you want. I love you."

He smiled, a sort of condescending smile, but one that showed he was touched by my proclamation. "Be careful what you say, Alyssa," he said. "Those can be dangerous words."

"But it's how I feel. Maybe I really don't know you that well, but I know I'm in love with you."

"Even though we can never have a life together?"

Strangely enough, his words did not bother me. The idea of never being his wife, never wearing his ring, never having his children, was not distressing. I understood, somehow, that such a relationship would compromise my love. "What matters is right now," I said.

"Indeed," he said.

He took me to a casual bar and grill down the street, and the hostess took us to a secluded booth. People were checking us out, undoubtedly making comments about an obviously older man holding hands and kissing a teenaged girl. I loved the attention, and could tell that it amused Ian as well.

Our waiter was a young man, good-looking and slim, whose eyes roamed over me as he took our order and checked back with us. He kept stealing looks at me now and then as Ian and I talked and ate.

"It seems our waiter is infatuated with you," Ian commented.

I blushed and giggled. "Too bad for him," I said, giving Ian a dreamy look.

"Do you find him attractive?"

I frowned, and shrugged. "I guess so."

Ian's locked on mine. "Give him a blow job."

I stared, shocked at the proposal. "What?"

Ian smiled. "Go on. Go find him, convince him you want to be alone for a few minutes with him. I don't want you to return unless you have something to show me."

I searched Ian's face for signs that he was making a joke. But he wasn't. He was serious. He actually wanted me to give our waiter a blow job! The idea startled me, made me nervous. But I was also turned on. I realized that I would never refuse Ian.

Without a word, I set my napkin on the table and stood. I looked around, spying the waiter standing along the edge of the bar. I approached him casually.

"Looking for the bathroom?" he asked me, his eyes wandering over my breasts and legs.

I fixed him a look. "I need to talk to you about something," I said. "But not where my boyfriend can see."

"Um . . . sure," he said, and lead me around the bar toward an alcove. It was actually a secluded table, presently unoccupied, as were the three or four tables around it. I figured I could sit in that booth and not be seen at all, especially if my waiter was standing in front of me.

"Let me guess," said the waiter as I stepped into the alcove. He followed behind. "It's his birthday, right? Or, this is like a late Valentine's—"

"Do you like blow jobs?" I asked him, standing close and staring into his face.

That startled him. "Wh-what?"

"Blow jobs," I repeated, and slipped my hand under his apron, finding a soft bulge in his black work pants. It began growing as I massaged it.

"Jesus!" he muttered, looking around frantically. "What are you, crazy?"

"Yeah," I said with a smile. "Cock-crazy."

"H-hey, look," he stammered, trying to push my hands away. "If this is some kind of joke, if you're just fucking with me to make your old dude boyfriend jealous—"

"Well, he didn't say anything about fucking," I said, lifting his apron and tugging on his zipper. "He just told me to give you a blow job."

"He . . . he told you?" asked the waiter incredulously, no longer trying to stop me. I got his zipper down and slipped my hand in his pants, finding a semi-hard penis hidden in his boxers.

I giggled playfully and pulled out his cock. "It was his idea," I said, and sunk down onto the bench. His dick was fairly big, not as long as Ian's, but just as thick. It dripped pre-cum as I stroked it with both hands.

"Oh, man, I can't believe this," moaned my waiter. "Okay, if you're gonna do it, do it qui-ahhhh . . . ."

He trailed off with a sigh as I wrapped my lips around his throbbing pole and began sucking. I didn't have time for finesse, so I just sucked hard and sure with the intention of making him cum in my mouth. I bobbed on the first few inches and stroked the base with my hands, squeezing and urging on his orgasm.

It didn't take long. I knew how to get any guy off, and how to do it quick. The waiter held his apron up with one hand, placing his other hand on my head. He shivered with pleasure, trying to stay quiet, and only let out sharp, faint grunts when his cock twitched and pulsed, spitting its hot salty cream all over my tongue.

I massaged his cock with my lips to get every last drop, then slurped my mouth off him and slipped his spent penis back in his pants. The waiter shuddered with aftershocks, petting my hair. He gave me a goofy grin as I stood.

"God damn, you're good at that, baby," he said gratefully.

I smiled. "Mm-hm," I agreed, then abruptly left him, heading back through the restaurant. I felt self-conscious, wondering if anyone else in the restaurant had seen what I had done. In a way, I almost hoped they had.

I returned to Ian, and sat down across from him once more. He looked to me expectantly.

"Do you have something to show me?"

I glanced around, knowing that the waiter and a couple of his buddies were looking my way. I caught them staring at me in disbelief as my waiter described what I had just done. I looked back to Ian, smiling, and opened my mouth.

Ian chuckled upon seeing the puddle of semen on my tongue. "Good girl," he said. "You can swallow it now."

I closed my mouth, sucked down the bittersweet juice and licked my lips. I felt naughty and kinky, with the impression that I had proved something to Ian. I had given a blow job in public and brought back my reward to show Ian like a devoted kitten. "So, you said you wanted to talk to me about something?" I asked, sipping my Diet Coke. My lips were sticky around my straw.

Ian studied my face a moment. "How would you like to make a thousand dollars a day?"

I blinked. "Who do I have to fuck?" I asked rhetorically.

He pursed his lips a moment. "Whoever has the money to pay," he said.

I blinked again. "W-wait a minute," I said. "You're serious?"

"Are you?"

I breathed out, looking down at my half-finished hamburger. "Y-you want me to . . . have sex with other men," I said. "For money."

"Oh, come now, Alyssa," Ian said in a patronizing tone. "How much different would it be from what you were doing? And, let's not forget how you lost your virginity in the first place."

I took in a shuddering breath. "This is different," I said.

"Is it?"

I lifted my eyes, finally looking at him. "A thousand dollars a day?"

Ian nodded. "You pick the days," he said. "As few or as many a week as you like. You will be picked up by my service, taken to meet your client, and the service will pick you up again when you are ready."

The idea was both intimidating and arousing, I had to admit. And Ian did have a point. I had been sucking cock for money and gifts for months already. Why would it be such a difficult leap to move on to fucking for money? I had already done it once, after all.

A thousand dollars a day!

"Who are the men?" I asked Ian.

He smiled, knowing he had me now. "Business associates, mostly. Most will be men away from home, and often, they will be married. But that doesn't seem to bother you."

A thought entered my mind. "Is this why you wanted me in the first place?" I asked. "To make me your personal hooker?"

His eyes hardened a little. "A thousand dollars a day, Alyssa."

I looked away, feeling that I had been manipulated, used. But how could I really blame Ian for his idea? He had paid twenty-five thousand dollars, after all, for the privilege of fucking me, of taking my virginity. And I had given it to him gift-wrapped in a little blonde box.

So, why not do it, Alyssa? the little devil in my head asked me. Sure beats chugging down cum for shoes and CDs . . . .

"You don't have to give me your answer right away," he said. He touched my hand, making me look at his face. He was smiling in that comforting, 'trust me' way again. I managed to smile back.

"So, what would you like to do now?" he asked casually, as if we had just finished talking about our favorite TV shows. "The night's still young."

I didn't say anything. I just gave him a little smile and stood, and headed slowly for the front door. He followed quickly behind.

***

I moaned and grunted beneath him, laying on my stomach with my legs parted wide, each pounding thrust Ian made inside me forcing air from my lungs. Beads of sweat dripped down my forehead; Ian had been fucking me hard for nearly an hour straight, in every position we could think of. His stamina amazed me.

Hammering into me, Ian leaned over and sucked the nape of my neck, making me squirm. I felt my cheeks shake as he smacked his hips repeatedly against me. "Are you on birth control, Alyssa?" he asked.

"Yes! I! Am! Uhn!"

Ian pushed up on his arms, thrust home hard and trembled. "Good," he grunted, and I felt the flood of his semen filling my womb. The warmth of his orgasm flowed through me, making me shudder and sob pleasurably in my fifth or sixth orgasm of the night. Ian's cock twitched a few times, and he stayed inside me as he gently lowered his weight onto my body.

I licked my lips, murmuring in pleasure, slowly regaining my breath. Ian kissed my neck, my temple, my cheek. I just sighed in satisfaction, enjoying the afterglow with him. My pussy spasmed with aftershocks around his slowly-softening penis.

"Alyssa," Ian whispered.

"Mmmm?"

"I adore you."

I smiled. That was the closest Ian would ever come to telling me he loved me, I knew. I found the statement sweet, honest, and comforting. At least I wasn't just his sex toy.

After a while, he finally pulled out of me and got up. I stayed where I was, too comfortable to move. I curled my arms under me and closed my legs. I could smell Ian's cologne in the air, mingled with the scent of sex. It settled around me like a protective blanket. His thick, warm cream slowly dripped out from my pussy. I liked the feeling.

Ian came back and sat down on the bed beside me, running his hand up and down my back. I moaned appreciatively, turned my face to smile up at him. He held two unlit cigarettes in his hand in a silent offer.

I giggled, pushed up on my elbows. The movement forced out more of his fluid. I grimaced slightly as a thick glob of it rolled down over my clitoris to the bedsheets.

"Would you like me to get a washcloth?" he asked as he tucked the cigarette between my lips.

I shook my head as he lit my smoke. "Too late now," I said, still smiling. I breathed out a stream of smoke. Damn. A cigarette really was the best thing after sex.

"My God, Alyssa," he said, revealing more emotion than he ever had. "You are absolutely ravishing. I wish you could see yourself through my eyes right now. I have never seen a woman glow the way you do."

I bit my lip, touched by his words. "I love you, Ian," I whispered.

He looked away, lit his own cigarette. My proclamation bothered him, I knew. Maybe that was why I said it; to get to him, to tilt the balance of power between us a little more in my favor.

"Do you really want me to . . . 'entertain' other men?" I asked him.

He looked back, surrounded by a hazy cloud. "It is just an offer," he said.

I considered my cigarette, pulled on it. "Do you have other girls?" I asked.

He was quiet for a moment, pursing his lips. I got the feeling I had touched a nerve.

I chuckled darkly. "You do, don't you? Well, you're just a regular pimp, aren't you?"

Ian cocked his head. "I own many businesses," he said. "Not all of them are completely legitimate."

I fell silent, smoking my cigarette. So I'm not the only one, I thought, then chided myself. How could you think you ever were, Alyssa? Did you really think you were that special?

Ian reached for the little plastic ashtray I kept on my bedside table, set it on the bed. We were both quiet. He waited for me to speak first.

"Will we be able to keep seeing each other?" I finally asked.

Ian brushed a lock of my hair behind my ear. "Of course."

I smiled.

***

Ian introduced me to an attractive woman named Cleo that following Saturday. I figured she was around thirty years old. She was very stately, with the right mix of elegance and casualness. A couple of inches taller, with long, free-flowing black hair, she was more busty and had slightly bigger hips than me. She didn't have the hard look of a woman who had spent years on her back with hundreds of men, if indeed, she had. But she did have a strong sense of self-confidence.

After lunch with Ian, Cleo took me shopping. Not to trendy shops in the mall, but to some exclusive, elegant places that featured the kinds of clothes I had only seen on Hollywood stars. Cleo was a friendly, outgoing woman and I took to her easily. She had a wicked sense of humor and was very intelligent. She stressed that both traits were necessary for a good 'escort.'

"So that's what we're called these days?" I asked as Cleo and I left her surprisingly humble SUV and headed to the first business we would patronize that day.

She gave me a sly look. "Yes, that's what we're called these days."

I followed Cleo inside the store, gasped as I looked upon the array of clothes. Expensive gowns, shoes, gloves, scarves . . . the place smelled of money and good perfume. An older woman in layers of multi-colored clothing glided toward us. She seemed to know Cleo pretty well.

The woman's name was Anne, and she and Cleo treated me to a crash-course in the wearing of elegant clothes. They stripped me naked, right there in the store, as a few other women shopped. None of them seemed bothered by my nudity. My modesty vanished quickly as I became preoccupied with various articles of clothing. Pretty soon, I was slipping in and out of outfits with casual ease.

I learned a lot about bustiers and evening gowns, garter belts and stockings. I was shown how to walk elegantly, how to balance on stiletto heels, how to conduct myself with 'poise and grace.' Anne and Cleo watched me walk around on a pair of six-inch spiked heels, first in the nude, then in a dress.