Not Just a Hitchhier

Back when I was in college, I worked in a series of restaurants and bars. I had a great time, but it opened some interesting doors in my life that I've decided to share.

One door that I remember fondly reflects how little I knew about the world back then. I was working in a popular restaurant and making great money. I would work late on weekends and make upwards of $200 in tips. The place was only five miles from my off-campus apartment, the staff was a great mix of young and old, and we had some great times hanging out and drinking after the place was closed. On a related note, the management was pretty loose about letting us have a drink or three when the work was done.

I don't remember why I did so well that night, but I left with almost $300 after I tipped out the bartenders and the busboy. I stayed at the bar while everyone cashed out, making sure to draw the blinds and shut off the main lights. When everything was done, though, we were all pretty beat and ready to head out. We all walked to the parking lot together to stay safe, and waved goodbye as we got in and got ready for home. I knew I had to stop for gas, though, because I had left it until the last minute and the tank was on fumes.

After many late-night stops, the clerks at the 24-hour convenience store were all friendly and familiar to me. One of them, Jacqui, ended up being a talented masseuse as well--remind me to tell you how THAT got started! Anyway, I filled my tank, chatted with the clerk while I paid and bought some snacks, and waved as I went back to my car. From there, I made a few turns before the city petered out and the road north to the college stretched out in front of me.

I had just shifted into 3rd and was settling back for the drive when I saw her. She was walking backward up my side of the road, her arm extended and her thumb up. I would have stopped for almost anybody at that time in my life, but as I took my foot off the gas, I grew increasingly happy with my impulsive decision. She was tall and slim, and her jeans showed off her shapely legs. A white crop top left her flat belly exposed, and a leather jacket gaped widely, revealing the swell of firm, high breasts. All of that was capped with an oval face framed by brown, curly hair and a knowing smile. She wasn't beautiful, but she looked smart and sexy and...intriguing as I pulled over onto the side of the road.

By the time she made it to the passenger door, I had the window down.

"Need a ride back to campus?" I asked with my friendliest smile. My assumption was that anyone headed north at that time on night on that road was a college student who got stuck downtown for some reason.

Instead of replying right away, she grinned more broadly and leaned both forearms on the bottom of the window opening. Her top fell forward as she leaned down, revealing an inviting swath of creamy skin and a good view of her cleavage. I tried not to gape too blatantly, but my eyes flicked from her face to the offered swell of her breasts and back again as I waited for a response. She grinned at my perturbed state, knowing full well the effect she was having on me.

"I'm not really hitchhiking," she said in a soft voice.

A car whooshed past us on the road, startling me with the sudden buffet of air. That brought me a moment to consider, though, and I came up with a good reply.

"Oh..." said, thoroughly confused by what she told me.

"Oh," she said teasingly, smiling to take the sting out of it. "So if you want to give me a ride back to campus, that's great, but you have to pay me if anything happens along the way."

"Oh!" I answered, much enlightened.

"So would you like to get a better look at these," she said, nodding down toward her cleavage, "or should I let you go and find another ride home?"

She watched me expectantly, her face calm.

Now, I knew there was prostitution in the city, and I had even seen some wizened-looking crackheads lurking on corners near the projects. This, however, was something else entirely. Even though I had NO idea what I was getting into, I could only answer one question at a time.

"I would LOVE to see more of those!" I croaked, clicking the unlock button after a blind fumble with my left hand.

Her smile returned, and with a quick, graceful step, she opened the door, turned sideways, and slipped into the seat in a few seconds. The door clicked shut quietly and she pulled on her seatbelt. I sat there looking at her, not knowing what to say or do next, but my heart was racing.

"Drive, will you?" she said, nodding toward the empty road in front of us.

"Absolutely!" I told her, shifting into first and checking my mirrors.

As soon as we got back up to speed, she turned sideways to face me, her back against the door and her knees pointed at my side of the compartment. The wind from the open window whipped her hair and her eyes looked huge in the blue glow of the dashboard lights.

"You're not a cop, are you?" she asked evenly.

"No!" I assured her eagerly. Then my mind clicked into gear a tiny bit. "You're not a cop either, are you?" I asked.

"Definitely not," she said firmly. "But here's the deal. A quick visit is $25, half-and-half is $50, and if you want a whole around the world it's $100 for one pop."

I was no innocent when it came to sex, but I had no idea what she was talking about. So I threw myself at the mercy of the court.

"I have NO idea what any of that means, but I definitely want to find out!" I assured her.

She laughed only a moment at my ignorance. Then she returned to a more businesslike tone.

"Do you have $100?" she asked me.

"I do."

"Good," she said. "Then we can have a little party if you want, and I'll do whatever you want to get you off. Does that sound good?"

Her hand reached across the center console and came to rest on the dense black khaki of my waitering pants. Her fingers trailed down the inside corner of my thigh to my knee, then reversed course and followed the same line upward until they brushed along the crease of my hip and the backs of her knuckles grazed my hardening cock.

"That sounds great!" I gasped as she made contact with my package.

Her hand withdrew. "First things first. My name is Jessica," she said briskly, her palm now upward in the universal gesture that says, "pay me" in any language.

Since I was driving, I was sitting on my wallet. I fumbled it out and set it on my lap, then slipped my fingers inside to select the proper bills. Looking back, I'm cringing at how stupid that was, but what did I know about paying a prostitute? I was horny and all the blood had left my brain to swell other, more essential areas.

As I separated the two $50 bills I had from my night's work, Jessica was looking at the rest and grinning. When I placed the two bills on her waiting palm, she smiled brightly.

"Thank you!" she said happily. "That's a lot of money you have there!"

I didn't really know how to answer that, so I nodded dumbly until I thought of an explanation.

"I had a good night at the restaurant," I told her, carefully omitting the name.

"Cool!" she chimed back. "I used to work in a restaurant--it was great!"

"Yeah," I admitted. "It's pretty good work, and the money can be amazing."

Somehow it didn't seem right to ask her about HER job, so I just kept babbling. Fortunately, her hand had returned to my thigh, so I passed the halfway point to campus in a state of blind, ecstatic arousal.

"So...I've been there for almost a year now," I confided. "They money's good, and the staff is really fun to hang out with, and the food is actually good. That makes a big difference!"

Again--I cringe when I think about the nervous, inane chatter I offered her. Fortunately, she was professional enough to ignore it gracefully.

"Do you want to go all the way back to campus, or do you want to find someplace quiet and get started?" she asked gently, a smile tugging at the corner of her mouth.

I stopped babbling. "Someplace quiet sounds like a good idea!" I said fervently.

She glanced up the road and then said "Take the next left!"

I slowed and downshifted when I saw the green flash of a street sign come out of the darkness. Turning left, I didn't recognize the name of the road, so I asked politely, "How far?"

"Just go down to the parking lot," she said, stroking my inner thigh all the while. "No one goes there after dark.

We passed a few widely-spaced houses along the road, most of them dark and quiet against the backdrop of the woods. After a stretch of dark trees, though, I saw a lone street light illuminating the front of a small building. Next to it was a parking lot with a half dozen spaces.

"In there?" I asked hesitantly.

"Yup," she told me. "Just part next to the building so we're kind of in the shadow, and then turn off the car, okay?"

I said "Okay" and did as she directed. The quiet of the area rushed in and filled the car, broken only by the ticking of the engine as it began to cool.

"So let me explain..." Jess began. I turned to face her, my heart pounding.

She unbuckled her seatbelt and let it retract behind her. Then she put her arms back and let the leather jacket slide down to her hands before she tucked it behind her against the door.

"A quick visit means I come over there and give you a blowjob," she said as she looked into my eyes. Her hand found my hard cock and gave it a squeeze. "Half-and-half means I start by giving you a blowjob and then you finish in my pussy, okay?"

I nodded and whispered "Okay!" in return.

"Around the world means you can put dick anywhere you want--in my mouth, in my pussy, or in my ass, but you only get to come one time for a hundred dollars. Got it?"

"Got it!" I answered, my eyes wide.

"So you gave me $100..." she said, leaning forward across the center console, pushing her breasts up to draw my gaze to something concrete. "Why don't I start with a blowjob and we'll see what happens?" A pleased look crossed her face as she made that last suggestion.

All I could do was nod, and her grin widened knowingly, fully aware of the uncertainty inside me.

What the hell? I asked myself. I've had sex before. I've gotten laid in a car, and I've gotten a blowjob from someone I just met. Why am I so turned on and so freaked out?

Because she's a pro! I answered myself internally. You've never had someone tell you that you can fuck every hole if you give her money, moron!

Jess's hand left my cock and her thumb depressed the button on my seatbelt. The strap pulled itself up and back, catching on my left arm before I shifted enough to let it slide past me. She ran her hands flat up my thighs, then, and her thumbs bumped along the rigid underside of my cock. When she reached the top, her fingers deftly opened my belt buckle. I sucked in my belly to help as her fingers worked the button open. Before she proceeded to the zipper, however, she paused and looked up at me again.

"I don't like dealing with zippers," she said. "Let's get these all the way down and out of the way, okay?"

"Okay!" I agreed quickly, leaning back so that one arm rested on the seat back while the other hung onto the top of the steering wheel.

Her deft fingers unzipped me and then hooked the waistband of my khakis. I lifted my hips to help the procedure and she whisked them down to my knees. Intentionally or not, she also dragged my boxers down at the same time and my hard cock snapped back against my belly.

"Mm..." she cooed happily when she saw what she had exposed. "Very nice! I can definitely work with that!"

I grinned idiotically, blindly believing her line. One cool hand came to rest flat on my belly with the edge of her forefinger pushing my cock upright. The other wrapped around the shaft and gave me a few experimental tugs. My cock throbbed and a pulse of precum leaked from the tip. Jess smiled and leaned down toward my lap, but stopped just short of her destination and looked up at me again.

"One pop means you get to cum one time, okay?" she asked.

"Okay!" I muttered, desperate to feel her tongue on me.

"If you want more after that, we'll have to renegotiate a little bit, hon. Are you cool with that?"

"Yes!" I said, still grinning. "That's fine...but please..." I began.

"Please what?" she said, her hand still idly stroking me.

"Please will you take off your top?"

The wicked, knowing smile flashed again.

"Of course!" she replied.

Sitting up and releasing my erection, she crossed her arms in front of her and grabbed the hem of her shirt. With a quick flex of her elbows, it was up and over her head. I watched it go, watched her hair fall back around her face and onto her shoulders. Then my gaze was drawn down to her bare chest, to the smooth, pale skin of her C-cup breasts and the small, dark circles that capped each one. Her nipples crinkled slightly in the cool air, and her hands came up to cup them, pushing them up and together as if offering them to me.

"Do you like my boobs?" she said in a teasing way.

"God, yes! They're beautiful!"

"I thought I saw you looking!" she taunted me.

Her thumbs came up and flicked her nipples gently back and forth while I watched, entranced.

"I like it when you look at them," she said in a softer voice. "It makes me so horny!"

I had no words to reply to that statement. I know now that I was getting played, but at the time, I was completely under her spell and ready to burst already!

"Now..." she said more brusquely, releasing her breasts, "where was I?"

She looked down and wrapped her hands back into position on my cock. This time, though, there was no interruption to her movement and I felt the warm circle of her lips engulf my crown. Sucking gently, she lapped the underside with the tip of her tongue, drawing a wild throb and another spurt of precum that she swallowed eagerly.

My hand fell to her shoulder as she leaned further and took half of my cock in her mouth. The heat was tremendous, and the soft, tight vacuum she created was amazing. I've had a lot of blowjobs since then, but she was the best of my early life and I knew I was in trouble! With a firm grip on the base, she tugged upward as her lips moved up and slid her hand down as she descended. More and more of my cock disappeared into her mouth with each stroke until I could feel myself bumping the back of her throat with each bob. I've never been the kind of guy to push a woman down or fuck her throat if she was unwilling, but my body began to respond to her treatment unconsciously. Each time she went down on me, my core tensed and my ass tightened up, pushing my hips up to meet her.

Jess was an expert for sure. The combination of her lashing tongue, the constant suction, the deft stroking at the base, and the grip of her full lips all along my shaft was a perfect storm of pleasure, and I was helpless to resist it. My head fell back, my eyes closed, and I lost myself in the whirl of sensation she was creating for me. Deep inside, I knew I was about to explode, but I could not imagine pulling her off me--I wanted so desperately to let her drive me over the edge to the natural conclusion of this moment!

As if sensing my inner turmoil, Jess speeded up her attack. I am 100% sure she wanted me to cum quickly and then pay for more fun, but all I felt or thought at the time was the crumbling of my resistance. My core tightened and my breath grew ragged as I thrust up into her mouth again and again. When her fingernails tickled their way through the trimmed hair on my balls, I was done for! My gut spasmed, my testicles bunched up in preparation for surrender, and my shaft thickened.

"Oh, God, Jess--I'm gonna cum!" I moaned wildly, my head pressed against the window.

She hummed to urge me along and sucked just the tip of my cock, stroking me furiously. In seconds, I felt the wave hit me and the first spurt of cum leapt up my shaft and into her waiting mouth. She kept perfectly still, though, swallowing quickly and milking my cock hard, catching my rhythm so that every stroke delivered another wave of cum that she gulped down. My whole being centered around the wild celebration of my cock as I throbbed and throbbed again, giving her all I had. When the pulsing slowed down, she took more of me back into her mouth again, sucking firmly and stroking the thick vein with her thumb to draw out my last few drops.

Finally, my cock began to soften. Jess kept her grip on the base but released me with a pop and looked up at me. When she saw my eyes just starting to open and the vacant gape on my face, she smiled a smug, feminine smile that comes at no other time--the smile of victory and sexual prowess that every man should be lucky enough to see.

Tugging me upright one last time, she planted a soft kiss on the shrinking head of my cock.

"Did you like that, hon?" she asked.

"Steve!" I murmured.

"Did you like that, Steve" she asked again, smiling at my admission.

"That was fucking amazing" I told her, my heart beginning to settle down at last.

"You taste so good!" she murmured sincerely.

I had no answer for that, so I simply caressed her shoulder and then her hair. She let me continue for a moment, but then hit me with that smile again and asked me a question she already knew the answer to.

"Do you want to keep going, Steve?"

I looked down at her for a moment, considering. I knew that meant more money, but God, I never wanted that feeling to stop, and I knew fucking her would be something unbelievable!