Pretty Baby Ch. 02

"Damn."

I turned around to see Katie leaning on the host stand, an impressed smile on her face. "I'm jealous," she said.

I gritted my teeth, looking away.

"No, I'm serious," Katie continued, pushing away from the host stand and approaching me. "He's hot. Even for an older guy. Bet he makes you scream, huh?"

I started to walk past her, then stopped and smirked. I looked over my shoulder at her. "I'll find out Thursday," I said, then continued into the dining room.

"I want details!" she called after me.

***

That Thursday afternoon, after coming home from school, I was nervous. I was more than nervous. I felt fear, anticipation, anxiety and excitement, all at once. I took a shower, wanting to be as clean as possible, but my libido wouldn't let me rest without release, so I masturbated in front of my vanity mirror, madly rubbing my clit until I spurted onto the sink. Then I took another shower.

I tried on various outfits. I wanted to be classy but still a little slutty, and to that end, finally decided on a sheer black dress that hugged my curves and showed off my cleavage. I contemplated going without panties, but decided that would be too slutty. Going braless would be enough.

I found a black silk thong to complement my dress, then rolled up some thigh-high stockings and slipped on my best black heels. God bless Marcus for his taste in shoes, I thought. I piled my hair up atop my head in a loose bun, securing it in place with chopsticks. Light makeup, red lipstick, soft lavender eyeshadow, and I was ready. The final touch was a little spritz of perfume on my neck, wrists, and the backs of my knees.

I stared in the mirror, taking a deep breath and slowly letting it out. Tonight, Alyssa, you're going to become a woman.

The knock at the door startled me. I gathered my composure, wobbled on my four-inch heels to the door. I wasn't used to walking in the things. I checked my little black purse to make sure I had everything I needed: mints, cigarettes, lighter, perfume, compact, lipstick, Handi-Wipes, keys . . . check.

I opened the door, expecting Ian. Instead, it was Miguel.

Miguel, from so many months before, the man whose cock was the first I had ever sucked. He wore a tuxedo and a black chauffeur's hat. His eyes bulged in recognition.

I slowly smiled, feeling a strange sort of sexy confidence. "Hey, baby," I said. "Are you my ride?"

Miguel blinked. "Um . . . u-uh, yeah," he stammered. His eyes dipped, taking in my long legs. He dragged his gaze slowly up my body and smiled. "I'm your driver for the evening. Mr. Holloway sent me to pick you up."

I smiled, meeting his gaze boldly. "Lead the way," I said.

Miguel smirked and headed down the walk from my apartment, toward a long, black limo with dark-tinted windows. He opened the door for me, looking me over.

"Don't get any ideas," I said warningly.

Miguel forced his smile away. "I'd never think of it, ma'am."

***

The privacy window between the front and back lowered once the car started moving. I sat facing the front, and could see Miguel's eyes in the rear-view mirror. He kept checking out my legs, and I suspected he was trying to look up my short skirt. I was glad I had decided to wear panties.

"I, uh, I was told this is a special occasion," Miguel said.

I smiled. Oh, irony! The first man I had ever tasted was now taking me to be with the man who would take my virginity. In a strange way, it was appropriate. If not for Miguel, after all, I would not be in the position I was now.

"It's a very special occasion," I confirmed.

Miguel nodded. "Um . . . anniversary? Birthday?"

I smiled coyly. "Something like that."

Miguel was quiet a moment, his eyes darting back to me now and then as he drove. Finally, he let out a nervous laugh. "Damn, baby, you are hot," he said at last. "I mean, smokin' hot!"

"Keep your eyes on the road, Miguel," I said.

He sighed, and drove in silence for a while.

"Why did you pick me?" I asked at last.

He looked to me in the mirror. "Huh?"

"That day, in the mall," I said. "You and your friend were waiting for me. Why me?"

Miguel looked uncomfortable. "Hey, we was just messing around," he said. "If you'd'a said no, we would'a let you go."

"That wasn't the impression I got."

We stopped at a light. Miguel turned in his seat and looked at me directly. "I ain't never raped no one," he said. "And I never will. Maybe you got that feeling, and if you did, then I apologize. But you gotta admit, once it came down to it, you liked it."

I laughed softly. "Of course I liked it," I said. "Hell, I've been doing it ever since."

Miguel's face registered surprise. He stared at me for a long moment, until a car horn blared behind us.

"Light's green," I said.

Miguel cursed, turned back around, and floored the accelerator. We were both silent for a while as he took the highway toward downtown.

"What you mean by that?" he asked. "What you mean by 'I've been doing it ever since?'"

I hesitated a moment, wondering if I should reveal just what, exactly, Miguel had opened my eyes to. I decided that, even if he never intended to influence me the way he did, he deserved to know.

"Before I met you," I told him. "I had never even seen a man naked before, much less touched . . . or blown one."

"You serious?"

I nodded. "That day, when you dragged me in the men's room and shoved your cock in my mouth," I said, using the rudest words I could think of. "I hated you. You were a crude, selfish piece of shit."

He frowned in the mirror. "Hey, hey—"

"Shut up," I said firmly, and smiled again. But it was the smile of a woman with the upper hand. "I hated you, Miguel, and I always will. But you know what's funny?"

"What's that?" he asked carefully.

I grinned. "I love you for doing it."

He frowned again. "Huh?"

"You have no idea what you started, do you, when you took me into that stall, when you made me taste a dick -- and cum -- for the first time. You don't have the slightest fucking idea, do you?"

"Bitch, you talkin' crazy—"

I glared. "Call me a 'bitch' again and you'll be hobbling home on broken ankles," I said seriously. "Don't fuck with me, Miguel. My man knows a lot of people." I didn't know if that was true, of course, but Miguel did not have to know that.

Miguel fell silent, glancing to me in the mirror, his eyes fierce and proud . . . but ultimately impotent. "Look . . . I'm sorry, okay?" he said. "Is that what you wanna hear?"

I couldn't help but laugh. "I really don't wanna hear anything from you," I said. "I just want you to know that, what you did that day . . . it changed my life forever, and brought me to where I am now. I guess, in a way, I will always be grateful to you. Even if you are a crude piece of shit."

Miguel said nothing, insulted and confused and dumbfounded by my words. He kept looking back to me, but his lips remained pursed until he pulled the limo up before one of the downtown hotels. Above the classic art deco awning was a red banner advertising the steakhouse in the lobby.

"We're here," said Miguel simply, and he stepped out of the limo. I watched him through the dark tinted windows as he walked around to my door. He pulled it open and offered his hand, helping me to my feet. In my heels, I was just a little taller than he.

"Thank you, Miguel," I said.

He didn't look at me. "Ask for Mr. Holloway inside," he said. "The Maitre'D is expecting you."

I touched his face. Despite everything, he was a handsome man. "Thanks, Miguel," I said, then headed up toward the doors of the restaurant.

***

I was nervous again as the doorman showed me inside and introduced me to the Maitre'D. The middle-aged man at the front counter gave me an approving look and smile and lead me through the dimly-lit restaurant toward the back. We passed a crackling fireplace which sent the sweet aroma of mesquite through the air.

The other tables were occupied mainly with couples, the majority middle aged, and I felt eyes upon me as I walked. I was out of place, and it was obvious. A pretty young blonde girl in a JC Penny dress, surrounded by age, Armani and Donna Karan.

But my heart flipped when I saw Ian sitting in the rounded booth, watching my approach. He looked the ultimate continental gentleman in his dark jacket, white shirt, and long white scarf, a snifter of brandy before him, a cigarette smoldering in a glass ashtray.

"Msr. Holloway, Madame," the Maitre'D said, and retreated.

I stared at Ian for a long moment, quivering on my feet. "Tell me this is only what I think it is," I said.

Ian cocked his head, frowning. "What do you mean?"

"This is only about us, right?" I asked. "This doesn't have anything to do with you wanting to take over Gary's company."

Ian smiled, looking amused. "No, it doesn't have anything to do with that," he said. "Although, I do have to thank a couple of his employees for letting me in on this little secret."

I looked down, feeling ashamed again, the wash of Catholic guilt surging over me. Once again, I was just a naughty little girl.

"Have a seat, Alyssa," Ian said, patting the booth beside him. "Come sit next to me."

Meekly, I did so, sliding across the cool seat, inching closer to Ian. I inhaled his manly scent once more. It sent little shocks through my body that gravitated quickly toward my clit. I was as aroused by Ian as I was intimidated.

"Now, tell me," he said. "Why would such a beautiful and intelligent woman such as yourself want to offer her virginity to the highest bidder?"

I shuddered. "It . . . it turned me on," I whispered.

"Hmm," mused Ian. "I suppose I can understand that. But, after all is said and done, don't you think you might regret this?"

I looked up to his face. "I hope not," I said.

Ian reached for his cigarette, tapped off some ash, and sucked on it. I watched his movements, the way his lips wrapped around the filter. Everything he did just made me more and more wet.

"My daughter is your age," he said, breathing out a long cone of smoke. He looked to me. "I wonder if she would do the same thing in your position."

I frowned. Oh, God, please don't let Ian be some kind of sick freak who has fantasies about doing his own daughter!

"But this is about you," he said. "And us. Are you really ready to go through with this?"

I stared at him blankly, unsure of what to say.

His eyes bore into mine. "I will give you one last chance to back out," he said. "You can leave, at any time during this dinner, and I will harbor no ill feelings toward you. You will still get your money, and I will not do anything to your friend. I promise that. But."

He leaned closer, and touched my chin. "If you are still here by the time desert is finished . . . you know what I will expect."

I nodded slowly, mutely. Then, acting on impulse, I reached up and grabbed Ian's head, pulling him down to mash my lips against his. As before, I whimpered and moaned into his mouth, found his tongue. I sucked on it like a little cock, and managed to draw out a moan of his own.

"How's that for an answer?" I asked heatedly, after breaking the kiss.

"I think . . . we should look at the menu," he said.

***

The sexual tension between Ian and I was obvious. It was one thing, I figured, to be on a date and hope for sex at the end of the night. But it was something else altogether to be with a man that I knew would soon be inside me, taking me, making me cry and bleed and sob and scream . . . I was as much nervous as I was horny.

Ian ordered for us both. We had Oysters Rockefeller for an appetizer, a couple of Caesar salads, then grilled sea bass and filet mignon for the main course. All throughout the meal, Ian and I traded little anecdotes about our lives. He talked freely of his wife and daughter, giving me the impression that he felt no guilt whatsoever about our impending intimate union.

We had a slice of Key Lime pie for desert, with Ian and I feeding each other like a newlywed couple. We laughed and giggled, feeling more and more comfortable.

After dinner, I had expected Ian to take me upstairs to a room at the hotel. Instead, he lead me back outside, to the waiting limousine. Miguel opened the door for us, giving me a quick glance before I slipped inside.

Ian raised the privacy screen and turned up some music. Soft jazz. He opened the cabinet and produced a bottle of strawberry vodka. I shouldn't have been surprised. Ian had done his homework.

We mixed cocktails, drank, and talked some more. I nuzzled closer and closer to Ian as the limo rumbled quietly. I could not have cared less if Miguel was driving around in circles. I loved being with Ian, loved the way his strong body felt against mine. I loved hearing him talk, telling me stories of his youth in New York. I realized that Ian was almost three times my age. That just turned me on more.

We started kissing. Not just soft, promising kisses, but serious, 'I want you now' presses of our lips. I did not protest, as our tongues dueled, when Ian pulled up my dress and pressed his fingers against my inner thigh. Indeed, I spread my legs wide, slipping one over his lap and encouraging him on.

I gasped when his fingers rubbed my pussy through my thong, and sighed when he pulled it aside and began slipping his fingers up and down my dewy slit. I moaned and sighed into his mouth, kissing him frenetically as his fingers delved inside me. His thumb pressed against my clit while his index and middle fingers rubbed the roof of my virgin tunnel.

"Oh, God!" I cried, clutching Ian tight and bucking against him. He responded with a low growl and jerked his fingers harder and faster inside me. The pressure he plied to the top of my pubic mound with his thumb was almost painful. But the pleasure . . . oh, it was intense . . . .

I had squirted before in orgasm, but never had I ejaculated like this! My pussy was literally flooded with fluid when I came, and gushed out all over Ian's hand, spurting in a high arc and splashing wetly onto the floor of the limousine. I was astounded, amazed, and uncontrollably turned on. One orgasm turned into two, then three . . . .

My pussy swollen and dripping, my inner thighs wet, I shoved Ian onto his back and practically ripped through his clothes. I grabbed his expensive slacks in my hands and tore them from his hips, exposing his hard cock. It sprang up, hovering above his trimmed black nest of pubic hair. Partially circumcised, the dark foreskin stopped just under the crown of his cock. Ian's was the most impressive penis I had ever seen.

I grabbed his shaft, tilting it toward my face as I settled on my knees. I stared up into his eyes. "I want it," I hissed. I licked up and down the shaft, tasting the sweet, salty flavor of him.

"Do you want to drink from it, little girl?" he asked, petting my hair. His self-confidence was overwhelming.

I lapped softly at the head of his cock, tasting sweet dribbles of pre-cum. "Yes," I said, my voice strained. "Please."

Ian said nothing more. He just pushed my head down and closed his eyes, relishing the sensations I gave him with my experienced lips and tongue. I sucked and pulled, working my mouth back and forth. The head of Ian's cock rubbed against the roof of my mouth, popped in and out of my throat as I took him deep. He was about the same thickness as Gary but almost half again as long. I really had to push down before I felt his pubic hair against my lips.

"Oh! Alyssa!" he cried once I had swallowed him all the way. Encouraged, I bobbed up and down rapidly, literally throat-fucking him, feeling my hair fall free from the chopsticks and dance against my cheeks. I finally had to come up for air, breathing in deep through my nose, sucking hard and wet on Ian's long, stiff penis . . . .

"Uhhnnn," he grunted, slapping his hands to the leather seat, digging in with his fingers. His cock pulsed and throbbed, unleashing a torrent of thick, sweet cream that inundated my tongue and flowed to my tonsils. I moaned at tasting his cum, my ego soaring with the knowledge that I had taken this powerful man and reduced him to a semen-spurting machine.

I sucked to get it all, letting his creamy cum flow back and forth in my mouth as my lips and tongue massaged his softening dick. I kept it in my mouth, sliding my slippery lips up and down while Ian shuddered with aftershocks. Only when Ian told me we were 'here' did I finally pull my mouth off him and swallow.

We took a few moments to arrange our clothes and have another cocktail. The vodka was making me relaxed without detracting from my libido. Miguel opened the door, letting the aroma of cum and pussy drift out. I knew he could smell it, judging by the reaction on his face. He gave me a forlorn look, jealous that what he had once coerced me to do, I had done willingly with Ian.

Ian slipped Miguel a folded bill, and asked him to wait for the night. Miguel looked my way a moment, uncomfortable about the idea, but nevertheless agreed. He got back behind the wheel and drove around the property as Ian took my hand.

We stood before a large, stone-brick house, surrounded and hidden by trees. I could just make out an underlit pool toward that back. The sounds of cicadas and other hidden wildlife echoed from the trees. There was a hand-carved wooden sign by the stone steps that lead to the door. "The Grey House. A Secluded Romantic Hideaway."

Ian gave me a smile, ran his thumb across my lips. I thick white dollop of cum dripped down his digit, and I sucked it quickly into my mouth, staring up into his eyes.

"Come on," he said, and lead me to the front door. I held onto his hand desperately, like a little girl trusting Daddy to take care of her.

There was a middle-aged woman behind a small desk just inside the door. She smiled as Ian approached, and gave me a knowing look. "Mr. Holloway," she said. "Nice to finally meet you."

"Is everything arranged?" he asked.

The woman smiled. "Down to the letter, Mr. Holloway," she said. "Down to the letter."

A skinny, pale-skinned young man appeared, slightly stooped, and offered to show us to our room. We followed him up the stairs, with Ian ahead of me. Glancing back to the front desk of the bed-and-breakfast, I saw the middle-aged woman giving me a wistful smile. She waved with her fingers. I waved back with an awkward smile. How many times, I wondered, has she seen older men bring their young playthings to this house?

The porter opened a round-topped door and showed us into our room. I caught my breath. The scene before me was absolutely beautiful. A big, king-sized bed dominated the room, replete with four posters and a canopy. There was a small fireplace across from the bed, two low-back chairs and a chess table before it, and a French door that lead to the balcony.

Candles were everywhere, scented with vanilla that filled the room. The little flames flickered, casting dancing shadows upon the walls. On the bed, hundreds of rose petals lay, covering the turned-down sheets. Some had fallen to the floor. A crystal vase filled with the same crimson flowers stood on a stand beside the bed, next to a chiller in which lay a bottle of champagne. I felt like crying.

Ian slipped the porter another bill, whispered something in the young man's ear. The porter nodded, glanced to me, then nodded again with a smile before leaving. He closed the door behind him, and Ian turned the latch.

"Ian," I said, my voice shaking with emotion.

He turned and looked upon me. "Yes?"

"Thank you."

Ian just smiled, and took me in his arms. I melted willingly, kissing him with the deep, soulful passion I had been feeling all night. I moaned and sighed and held him close, feeling that I was absolutely and truly in love with this man. His hands roamed over my body, divesting me of my dress and panties with such grace and deftness that I hardly realized I was naked until I felt my clothes in a heap around my ankles.