Pretty Baby Ch. 01

And then there was Gary.

I had almost forgotten about the sexy older man, the married man with his hunter green Jag who had never gotten off from a blow job before he met me. About two weeks after our first time together, I was home on a Thursday night, having given up my shift to another server at work in order to study for mid-terms. I was doing well in all my classes except Economics, and I was determined to maintain at least a 3.5 GPA.

My cell buzzed in my purse, sitting on the couch in my tiny apartment. I ignored it at first, then got up and grabbed it when it buzzed again a few minutes later. The caller ID window was blank. I frowned, flipped my phone open.

"Hello?"

"Alyssa?"

"Yeah. Who's this?"

"Um . . . it's Gary. You remember me?"

I smiled. "Of course I do," I said. "What's up?"

He laughed. "Well, I am," he said, then checked himself. "Sorry. Th-that was kind of rude."

I giggled. "Not really."

"I'd like to see you again," he said. I heard some muffled sounds of traffic in the background, figured he was driving. "Do you, uh, have some time tonight?"

I thought about it for about half a second. My brain hurt from all the studying. I realized I needed a diversion. And Gary offered a very tasty one. "Sure," I said.

He sighed in relief. "Great! I'm on my way. You wanna tell me what apartment you're in?"

Hmm. . . "I'll meet you at the gate," I said, and hung up quickly. I giggled, and ran into the bedroom, stripping off my baggy house clothes and looking for something tight and revealing. I found a pair of tight grey jogging shorts and a pink halter, and quickly tied my hair into pigtails. Looking like a naughty little girl, I snatched up my keys and a can of Diet Coke from the fridge, then jogged out to meet my guy.

***

Gary was panting and sighing as I nursed his spent dick, licking up the last little bits of cum that seeped out. I kept his load in my mouth as I sat up and grabbed his cigarettes. Lighting one, I inhaled the rich aroma of tobacco and semen, smiling in satisfaction. Only then did I swallow Gary's treat.

Gary just lay back in the driver's seat, making no move to cover up as he relished his afterglow. I snuggled against him, smoking my cigarette, letting him take a drag now and then. His hands lazily stroked my naked back and breasts as I let him kiss and gently suck my puffies.

"Damn, Alyssa, I can't believe how much you turn me on," he murmured. He chuckled. "I mean, it's not just that you're a gorgeous young woman . . . you are eighteen, aren't you?"

I giggled. "Wanna see my license?"

Gary smiled. "Jesus, half my age," he mused. He gave me a look. "You make me feel so young, you know that?"

I smiled back, thinking:don't get too close. "Gary . . . ."

"I know, I know," he said, pulling away to get a better look at me. "I really like the pig tails."

I giggled again, for effect, and shook my head back and forth, making my piggies bounce and sway. Gary laughed, then his face drained slowly, the smile fading.

"Why do you do it?" he asked me.

I pulled on my cigarette, blew smoke. "Do what? Get picked up like this?"

"Well . . . yeah."

I shrugged, "It turns me on," I said.

"Do you really like doing it as much as I think you do?"

I smiled coyly. "That depends. How much do you think I like it?"

He gave me a level gaze. "I think you can't go a day without giving head."

I bit my lip, smoldering my eyes. "You're right."

He took a deep breath, chest rising and falling. "I have a proposition for you," he said.

I regarded Gary suspiciously. "What's that?"

"Well," he said, folding his arms behind his head, obviously enjoying being half-naked in a car with a teenager, his dick hanging out. "I work for a systems analysis company. Basically, we're a bunch of geeks—"

"You don't look like a geek to me," I said, playfully touching his pudge. I kept my hand on his stomach and slowly slid it down.

He chuckled again. "A lot of the guys in my department are," he said. "I mean, some of them have essentially no chance whatsoever of getting laid in their entire lives. It's like that line from 'Real Genius.'"

I frowned. "Huh?"

Gary shook his head. "Never mind. Before your time."

I gave Gary a funny look as I began fondling his floppy penis. It was still wet from my mouth, and slowly responded as I lightly stroked it. "You saying you want me to do your whole department? How many guys are we talking about?"

Gary shrugged. "Around forty."

I gulped. "Wow."

"Not all at once, of course," he said, shifting his hips as his cock started to stiffen again. I smoked my cigarette and pulled on his dick, making it grow in my hand. I liked watching it get thicker and longer.

"See, what I was thinking was maybe a few guys at a time, maybe once a weekend," he said, his breath becoming more labored as I stroked his dick up and down.

"And they'll all pay?" I asked, getting turned on by the idea.

"Oh, trust me, they'll pay . . . ." his words drifted off, eyes fluttering closed as I pinched and massaged the sensitive head of his cock. A thick dribble of fluid oozed out, and I leaned over to lick it away.

An image flashed in my mind, then, garnered from some of the dirty magazines I had seen. An image of me, on my knees, surrounded by stiff, throbbing penises, dripping their sweet fluid onto my tongue. And me holding fistfuls of cash.

I trembled with excitement at the naughty idea. My pussy twitched. I realized I could not have refused Gary's Idea.

"Set it up," I whispered, stretching out to get comfortable. I handed Gary my cig, then nuzzled his balls with my lips while stroking his hard cock. I loved smelling the residue of sticky semen that had soaked into his pubes. The taste of it was sweet on my tongue as I rolled his heavy balls between my lips.

"Oh, shit," moaned Gary, threading his fingers through my hair. "God damn, you're a hot little bitch. Suck my cock, Alyssa. Suck it and eat my cum."

"Mmm . . . ."

***

I didn't hear from Gary again for another few weeks, and put his proposal from my mind. I was getting dick on a daily basis, as it was, satisfying my desire for cum. I figured, when Gary didn't call me back after a few days, that he had either changed his mind about the 'suck-a-thon,' or it didn't fly with his employees, or perhaps his wife had discovered he was stepping out.

But then, a few days after Halloween, Gary called again.

"Sorry I haven't called, babe," he apologized.

"It's okay. Not like we're girlfriend and boyfriend, you know."

"Of course. Been busy?"

"Just doing a lot of homework," I said.

"You're a student, huh? You never told me that."

I giggled. "Hard to talk with my mouth full."

He laughed. "What are you doing this weekend?"

"Working."

". . . oh. You, uh, got regulars on the weekends?"

I rolled my eyes. "No, I have a regular job," I said.

"Oh! Well, um, what's your schedule?"

"I'm off Sunday night."

"Really? That's perfect . . . that could work out."

"For?"

He paused a moment. "Did you forget what we talked about?"

"No, I didn't forget," I said, immediately feeling hot between my legs. "How many?"

"Four."

I breathed out. My pussy was literally dripping. I touched myself as I leaned back in my couch. "Including you?"

"Including me, five."

"Ummm," I whimpered, pulling my panties aside and stroking my slick lips. "How much?"

"Hundred each," he said. "I'll pay for the room and refreshments."

"Room?"

"Yeah. I'll get a motel room for the night. The guys will only stay as long as you want."

"Refreshments?"

He chuckled. "Whatever you want, babe."

"Mmm . . . strawberry vodka," I said, rubbing my clit.

"You got it."

"Gary."

"Yeah, babe?"

"Come over here and fuck my mouth."

". . . . I'll be there in twenty minutes."

"Apartment 1604. Hurry."

"I'm leaving now."

***

Gary shuddered over me, his thighs buried in my arm pits, warm, sweaty balls resting on my chin. He grunted and groaned as his semen surged down my throat, which I automatically swallowed since I had him so deep. He pulled back a little, giving me one last warm spurt of fluid on my tongue. I sucked him for a few minutes afterward, until he softened and pulled out.

He rolled onto his back on my couch, curling his arms around me. I grinned, nuzzling his hairy chest, rolling that last heavy drop of cum on my tongue as I kissed his tiny nipples. I listened to his heartbeat pounding in his chest, gradually growing more calm.

"Don't take this the wrong way, Alyssa," he said, stroking my back and kissing the top of my head. "But I love you."

I lifted my face, staring into his. "What?"

He smiled. "I love being with you," he corrected. "Like I said, you make me feel young. And I know we could never have a serious relationship, but I just want you to know, in a way, I love you."

I smiled fondly, and kissed his lips. "Thanks, Gary," I whispered. "No one's ever said that to me before."

He frowned. "No one?"

I shook my head. "Well, not including my mom and dad."

"I find that hard to believe," he said. "I mean, what about boys you've dated?"

I sat up, looked for Gary's cigarettes. "Never dated," I said.

Gary didn't say anything as I lit up. I turned back to him after blowing out a cloud of smoke, saw the surprised expression on his face.

"What?" I asked rhetorically. "Look, I went to an all-girl high school, and my folks are pretty religious. I wasn't even allowed near boys growing up."

Gary fixed me a wondering look. "Jesus Christ," he breathed. "You're a virgin, aren't you? That's why you didn't want to have sex."

I looked away, feeling a little embarrassed. I suddenly wondered why I had even let Gary into my little apartment, my sanctum.

"Hey," he said soothingly, sitting up and rubbing my back. I sighed, giving in to his touch, and leaned against him. "Hey," he said again. "It's all right. I hope you don't think I'm disappointed."

I sniffled, feeling tears beginning to form in my eyes as my emotions welled up. "I guess it seems kind'a weird, doing this stuff with you, and I've never been popped."

"It's not weird," he said, kissing my temple. "You're an amazing young woman, you know that? When I first met you, I thought you were just another 'working girl,' albeit the most gorgeous one I had ever seen—"

"How many girls have you picked up?" I asked him suddenly.

"A few," he said heavily, sounding ashamed. "I never went out, intending to pick up a . . . a girl, but it just sort of happened."

"You don't have sex with your wife?"

He sighed, and uncurled his arms from me, taking out a cigarette from his pack. "Sometimes," he said, lighting up.

"I'm sorry," I said, wiping my eyes. "I shouldn't—"

"Can I be your friend, Alyssa?" he asked, interrupting me.

I thought for a moment what a strange question that was, but then realized the sort of 'professional' relationship we had. Up until now, Gary had been just a cock, and I was just a mouth. But now, he wanted to be a friend.

I smiled. "Sure."

Gary smiled. "I married Terry fifteen years ago," he said. "We dated all throughout college, got engaged on Christmas eve. She was only the third girl I had been with and I was the second guy she had known.

"We were in love once, and I think we always will be, in a way," he continued. "We've got two kids, a boy, Steven, eleven, and Joyce, nine. I like to think I'm a good father and husband, for the most part. But even at my age, having sex maybe once a month gets frustrating."

"That's why you pick up girls," I said.

He shrugged. "That's why I keep the option open," he clarified. "The first time it happened was about two years ago. She wasn't a girl. Just a woman I met in a bar, almost my age. The quintessential barfly. She was so drunk, she kept calling me 'Bobby.'" He laughed ruefully.

"I felt bad about it, and told my wife. She was mad at first, and I slept on the couch for about a week while she decided whether or not to file for divorce. I told the kids I was sleeping on the couch because I was sick and didn't want to infect mommy. I had to fake a cough the whole time.

"Then Terry decided that she wasn't going to file for divorce, that she understood that I had stepped out because she and I weren't having sex. For about a month, she tried to be more romantic and affectionate. I almost thought that we were getting back to the way we had been before Steve was born. But then it dried up again."

I tapped ash off my cigarette. "So . . . ."

"So . . . I was coming home from work one night, and I saw this young woman on the corner. I circled twice before I picked her up. It was funny. I was so nervous, I couldn't tell her what I wanted. But then she . . . picked up her skirt, grabbed my hand . . . I had to sneak back into the house and wash up so my wife wouldn't know. I think she knew, anyway, though she's never said anything."

I was quiet. I didn't know what to say. On one hand, I could sympathize with him, but on the other, I thought what a bastard he was for cheating on his wife. But it really wasn't my place to say anything. I was the 'other woman,' after all, and a prostitute to boot. I had no grounds for making any kind of moral judgment.

"When I first picked you up," Gary said. "I thought how lucky I was for finding you. You did . . .amazingthings to me, Alyssa. I couldn't stop thinking about you for weeks. I literally ached to be with you again. But with my wife, and kids, my job . . . I never had the time. But now I do. I know we're not going to have a real relationship, Alyssa, but I want to keep seeing you. And I want to be your friend."

I managed a smile. "So why the other guys?" I asked.

Gary grinned. "Just helping out a friend," he said. "I had the feeling, after that first time, that you were one of those rare girls who . . . well, who got off on cum. And I've always wanted to be part of a blow bang."

I laughed, rearing back. "'Blow bang?'" I asked. The term was new to me.

"Yeah," said Gary. "You've never heard of that?"

I bit my lip. "No. I've heard of gang-bangs, but—"

"Well, it's the same thing," said Gary. "Except it's just your mouth. Don't worry, Alyssa; I'll make sure all the guys know that your . . .down belowis off-limits."

I smiled, looking Gary over. I loved watching him smoke. He had a casual flair about it that reminded me of John Travolta in 'Michael.' Looking at him, naked in my living room, and still tasting his cum in my mouth, I was getting turned on again.

I leaned forward, stubbed out my cigarette in the ashtray Gary had made out of a Diet Coke can. Then I eased back and lifted my hips, slipping off the one last article of clothing I wore. Gary watched as I dangled my panties from the tip of a finger and lay back, spreading my legs wide.

"It's not off limits to you," I said. "Just don't go too deep."

Gary moaned in arousal. "Oh, baby," he muttered, then went down, burying his face between my thighs. I grinned and cooed, holding onto the back of his head as my new friend went to work with his tongue.

"Mmm, yeah, baby, eat my pussy . . . oh, yeahhhhh . . . ."

***

I was anxious and nervous the following Sunday. All day long at work, I fidgeted in anticipation of the evening to come. Gary had called me that morning, giving me the address of the motel and the room number, assuring me that he would bring a bottle of strawberry-flavored vodka. He assuaged my fears that some of the guys would want to go too far, saying that they would feel 'blessed enough' to enjoy my mouth.

My nervousness was telling, prompting some of my coworkers to ask me if anything was wrong. I told them that everything was fine, I had just gotten news about a friend who was in the hospital. The lie helped deflect any further questions.

Once I was done with my sidework and other duties, I caught the bus home, showered carefully, and applied fresh makeup. I dressed in a tiny little green skirt I had purchased just for the occasion, and a tight white Oxford shirt. I tied my hair in pigtails again, and seeing myself in the mirror, I decided that I looked like a hot little slut schoolgirl. Every man's fantasy. I grinned.

Perfect.

Gary arrived at seven, and commented on my appearance. He could barely keep his eyes on the road, especially once I lifted my skirt to show him the absence of panties. I knew he wanted to pull over somewhere and let me work on him, but I could also tell he wanted to wait.

By the time we arrived at the motel, I had dripped so much that my little skirt sported a very obvious stain in the back. Not that it mattered; I wasn't going to be wearing it for long, I figured.

The guys were already in the room when we arrived. There were four of them, as Gary had promised. Two were tall and skinny, another was pretty short and a little pudgy, and the fourth was downright fat. But they were all cordial and nice, giving me looks as if they were in the presence of a goddess.

I slugged down a strawberry vodka cocktail, and Gary switched on a music station on the TV. Britney Spears' 'Pretty Baby' was playing. It seemed appropriate. As the guys watched, sitting on the edges of the two beds, I did a little strip-tease for them. I loved the way they stared at my body as it was revealed. They moaned and groaned when I showed them my firm tits and licked my fingers, polishing my puffies until they shined. The fat one, Saul, just about fell off the bed when I dropped my skirt.

I got up on all fours on one of the beds, and all five of them knelt around the end as I masturbated for them. I loved the attention, and spread my snatch open wide to let them get a good look. They made appreciative comments about the appearance of my pussy, never once using rude words like 'cunt.' When I came, spurting all over the bed sheets, they applauded. I actually blushed.

Then they stood and pulled out their cocks. Now it was my turn to swoon.

Gary was a little above average in size, I had come to realize, topping out at about seven inches. The two tall guys were both a little smaller – I found out later that they were brothers – and the short guy was average as well. But Saul . . . .

The fat man had a dick to match his body. Maybe it wasn't too long, but it was easily thicker than my wrist. I wondered if I would even be able to fit the thing in my mouth. But with enough spit and some adjusting, I did, and Saul moaned as I stuffed his beer-can cock as deep as I could take it. He all but passed out when I drank his seed the first time.

I was in heaven, sucking one dick, stroking two others, while various fingers and the occasional tongue diddled my horny snatch. I made the stipulation that the guys could do whatever they wanted, as long as it didn't involve penetration and as long as they got off in my mouth. They all agreed readily.

I gulped down load after load of sweet, thick sperm, even took one on my face before scooping it up with my fingers as the guys watched, and sucking my fingers clean. Gary spent a lot of time licking and sucking and fingering my dripping puss, making sure I came over and over. I rewarded him with a deep-throat blow job that had him literally exploding in my mouth.

The hottest part of the evening was when all five of them surrounded me, beating off and taking turns in my mouth. One by one they shot their loads onto my waiting tongue, until I had all five loads floating heavily in my mouth. One of the guys handed me my compact so I could see the erotic image of all that cum at once. I couldn't even see my tongue, there was so much milky fluid. I had to swallow twice to get it all down, and the guys cheered.

By the time I announced I'd had enough, each of the guys had cum at least three times. My mouth was tired and my tummy was full. I had swallowed so much dick sauce that I actually burped up sperm. I kissed the guys good bye as they left the room, even walked out naked onto the breezeway to wave them off. Saul gave me such a look of gratitude before he left that I was touched. Then I headed back inside, where Gary lay naked and waiting for me.