A young man with adventure on his mind hits the highway — and the jackpot!

All my life, I’ve enjoyed traveling solo, and every once in a while, I’d have a serendipitous sexual encounter. I didn’t plan to have any adventures on my last lengthy road trip, but I did manage to meet two incredible ladies whose memory I’ll forever cherish — one of whom changed my life forever.

Before my last vacation, I’d purchased and restored a 1965 Mustang convertible, cherry red. I considered where to drive it when I thought of Route 66. If you’re old enough, you remember the song. If you’re of a literary bent, you know it’s featured in John Steinbeck’s The Grapes of Wrath; he referred it as “The Mother Road.” It runs from Chicago right up to the ocean in Santa Monica, California and became well known as the westward route during the Dust Bowl years. Today it exists only in bits and patches, made up of many roads. But some enthusiasts have created guides that make it easy to follow the original path in its entirety.

I live in Chicago, so figured it would be ideal for my latest trek. I would eat in no chain restaurants, stay in no chain motels, and hopefully see the “real” America. When driving across the country on an Interstate you often see nothing unless you get off at an exit. On the old Route 66, you’d go through town after town, hamlet after hamlet, village after village. It’s slow, but it’s a lot more interesting.

The wanderlust inspired by the road less traveled has its appeal for sure, but this trip had lustful delights beyond wandering. I left from Grant Park and headed through Illinois, Missouri, Kansas and Oklahoma. Then I hit the Texas panhandle, which is a whole lot of nothing. But I was having a good time, taking pictures of old roadside attractions, abandoned gas stations, mom-and-pop diners, etc.

The only major city along that stretch is Amarillo. My adventure did not occur there, however, but in a little town before it that isn’t even on most maps. The experience was like stepping back into a different time. The town was basically just a crossroads, with a gas station, a diner, a hardware store and a post office. I assumed most people in the area were ranchers or farmers, judging by the mud-splattered pickup trucks parked along the main street. It was getting near sundown. I was hungry and figured I’d get something to eat there and try to make it to Amarillo by nightfall.

I walked into the diner, which was like a movie set. There were a few booths and six stools lining the counter. Baked goods were on display under clear plastic covers. There were specials advertised on the wall, including meatloaf and beef stew. I took a seat on a stool, thinking meatloaf sounded good. I didn’t see the waitress until I noticed she was sitting in a booth, reading a battered paperback copy of Jaws. She glanced up and saw me, flashed a smile and came around the counter. My heart stopped.

She was fair-skinned with an interesting face. Her jaw was prominent, and when she smiled she showed off an adorable gap-toothed grin. Her hair was dyed fuchsia, though her roots were starting to show, but she didn’t appear unkempt. In fact, she seemed rather stylish and exuded a comfortable and confident air. She was definitely someone I wanted to get to know better.

“Howdy,” she twanged before taking my order. She wore one of those classic pink waitress uniforms, like the actresses in that old show Alice, only hers barely contained a pair of lusciously large tits. Her nametag read Ashley, and as I waited for my food I recalled the Ashleys I’d bedded. I was up to five when the only other customers in the place — an elderly couple — paid their check, said good-bye to Ashley and ambled out.

“We close at six, but I don’t want to rush you,” she told me with a friendly smile. She took her time heading over to the front door before flipping the sign there from “Open” to “Closed” and heading back behind the counter.

“Everyone else is gone, but I’ll hang here with you.” Though she quickly added, “But I don’t want to bug if you want peace and quiet. It’s just I always like chatting with visitors. Do you mind?”

Did I mind talking to a beautiful young woman? “Of course not,” I answered honestly.

So as I ate my meatloaf with gravy, cornbread and green beans, I told her about my road trip.

“I lined up my cock with her pussy and jammed myself inside her slippery slit.”

“Chicago?” she said. “I’ve always wanted to go there. It’s on my list.”

Ashley told me she was 22 and had been born in that town, but had big plans for her future and was saving her money for grad school in a city like Chicago.

“I do really like working here, though. It’s not super busy, and it’s fun talking to people who pass through town.”

I asked her if I could have dessert and offered to treat her, as well. She smiled again, and I loved that gap in her teeth. She looked sweet and sexy all at the same time.

Ashely got us each a piece of sweet potato pie, and I asked her if she had ever thought about being a model. “You’re tall, and you’ve got a great look.”

“Nah, that’s not my thing,” she said, taking a bite of her dessert. “Besides, I’m not interested in starving myself. I really like pie.” She flashed me that adorable smile once more and scooped up another forkful.

I finished up, settled the check and left the diner. A few minutes later she came out, locking the door behind her. She saw me sitting in my Mustang and came over.

“Cool car,” she said approvingly. “Listen, you don’t know me from Eve, but could I have a ride? My girlfriend usually picks me up, but she can’t make it.”

She had a look in her eye that suggested this might be the ride of a lifetime, so I pushed open the passenger door. She climbed in and settled back, while I peeled out of the gravel parking lot.

Ashley directed me down some country roads, and I paid careful attention so I’d remember how to get back later. I passed a whole lot of nothing while she chatted about something or other. I wasn’t hearing all of her words; my attention was elsewhere: Her little skirt had ridden so high up her thighs her underwear was exposed. She caught me looking and slipped a hand down her panties before uttering a fake moan.

She laughed when she noticed my cock responded, my erection now a noticeable bulge in my jeans.

“You’re really hot for an older guy,” she said, licking her lips.

I barely had time to feel flattered because she leaned over, unzipped my fly and took out my dick. I tensed up, but I realized there were no other cars on the road. “Make a left at the crossroads,” she said, before adding, “Want some road head?”

I nodded, unable to speak. She rubbed my cock against her lips and cheek. “It’s a big one,” she said, before licking up and down the shaft. Then she took me between her lips and began to suck me. I did my best to keep my eyes on the road and both hands on the wheel. She gripped my balls, which she’d also brought out in the open, and looked up to say, “Make a right after the barn.”

Before long we were at the entrance to a mobile-home park. Ashley tucked my cock back in and sat up. I didn’t expect anything more from her, but when she invited me inside, my heart and cock both did a little dance. I don’t remember much of the first room, other than a large poster of Marilyn Monroe, because she took me by the hand and led me straight to the bedroom.

Ashley sat back on the bed and pulled off her white tennis shoes. She flexed her toes and then parted her bent legs. She pulled aside her panties and began fingering herself. “Let me see that cock again,” she demanded. I pulled off my pants and underwear in record time. She shed her panties and took off her blouse and bra, letting those beautiful melons free. Then she got up on her knees to resume sucking my cock.

“I clutched her shapely hips and drove my dick in and out of her syrupy depths.”

I stood there by the bed, immobile and amazed at the talent of this young woman. When I was ready to bust, she pulled away and asked, “Would you like to fuck me?” Again, I only could nod. She swung around so she was on all fours. I lined up my cock with her dripping pussy and jammed myself inside her slippery slit. She was absolutely soaked, and she took me to the root with one thrust.

Stroking her back and hips, I slowly rocked in and out of her welcoming body. Her velvety pussy felt so good around my shaft. As my pleasure grew, so did my impatience and I picked up the pace. The faster and harder I pounded her, the more animated she became, moaning loudly and repeatedly slamming her body back to meet me. I clutched her shapely hips and drove my dick in and out of her syrupy depths while her cries grew louder and more desperate. Her arousal had reached a fever pitch, and it seemed as if she was on the verge of orgasm. I wanted to take her over the edge, so I snuck a hand beneath her to finger her clit while my cock jetted in and out. I felt her pussy tighten around my shaft before she began bucking wildly and shouting out her pleasure. The climactic spasms of her cunt massaged my cock so perfectly I was nearly swept away with her, but I managed to hold on — just barely.

Once she caught her breath, she pulled away to recline on her back. She parted her thighs in invitation, and I mounted her, once more plunging into her sloppy snatch. She was so very soaked and relaxed, and I was able to pound her as furiously as I needed. I felt out of my mind with lust as she wrapped her legs around me and murmured filthy encouragements in my ear.

Ashley’s dirty words faded into a series of wordless, musical sighs. Her velvety cunt clutched my pistoning shaft in mesmerizing spasms of bliss. I knew I wasn’t going to last much longer and told her so.

“Come in my mouth,” she insisted, pulling away and repositioning herself. She sat up and squeezed my balls with one hand while she yanked my cock with the other. A fountain of jism shot from my shaft into her open mouth, with some dripping down her chin. She laughed and wiped her mouth with the back of her hand.

“Thanks — that was fun, but my boyfriend will be here in about 15 minutes, so you’d better hit the road.”

Boyfriend? In Texas, an open-carry state? I heeded her advice, pulling on my pants before giving her a kiss and hopping into my car.

Happy with my narrow escape and my serendipitous taste of pussy, I drove across New Mexico in the following days with a smile on my face. In Winslow, Arizona, I stopped at Standin’ on the Corner Park, commemorating the Eagles’ song “Take It Easy,” and a day later I was wading in the surf of the Pacific Ocean at Santa Monica. I had made the entire trip but had no idea sexual lightning was about to strike twice.

My plan was to stick around L.A. for a bit before driving back along the Interstate, which would still take three long days. I stayed close to the beach, and one night walked into a dive bar in Venice Beach, longing for a cold beer after a day of swimming and sunning on the sand. It was there I first saw Bella, and my life may never be the same.

She was sitting at a table by herself. Classically beautiful — with strawberry-blonde hair, chocolate-brown eyes and alabaster skin — she looked perfect in the dim light of the tavern. Nothing about her posture suggested she’d be receptive to a come-on, but I took a chance and said hello.

She looked up at me annoyed, but when we made eye contact something about me must’ve pleased her, because she flashed a perfect toothpaste-commercial smile.

“Can I buy you a drink?”

She paused only a second before accepting my offer and introducing herself. We spent a long afternoon discussing our favorite books and music. We were really connecting.

“I was able to pound her as furiously as  I needed. I felt out of my mind with lust.”

The two of us adjourned to the tavern’s outdoor seating area and watched the sunset. We had talked for hours, and I felt like I’d known her all my life. One of the key facts she gave me was that she was between boyfriends. My relationships never last more than a few weeks, so I’m always between them. It seemed only natural that she invited me to have a nightcap at her place, a little bungalow within walking distance of the beach.

It didn’t bother me that our nightcap turned out to be figurative. She had pulled out a bottle of wine, but before she’d poured a drop we were exploring each other’s mouths with our tongues. I don’t think it could be defined as kissing, since lips were only tangentially involved. She had a stud in her tongue; I’d always thought those were stupid, but I have to admit it made kissing much more interesting. My cock was hard, and she grabbed hold of it through my pants, making my erection instantly spring to full mast. She broke our lip-lock to take off her shirt and bra, revealing full breasts topped with baby-pink nipples. The tiny nubs looked so delicate they almost seemed airbrushed on, but my fingers and lips discovered they were very real and very hard.

Bella laid me back on the sofa and unfastened my pants. I helped her worked them off, and they ended up across the room. She started sucking my cock lovingly, as if we had all the time in the world. She even dipped down to spend time licking my balls, which I absolutely loved.

When she needed a bit of a break, she repositioned herself on the couch on all fours. I removed the rest of my clothing and pulled her panties down, leaving her skirt bunched around her waist. I parked my nose in the crack of her ass and dined on her succulent slit. I love eating pussy, and Bella’s was delicious. She appeared to enjoy what I was doing because she was making small, soft moans of pleasure. She was not a screamer or a yeller, but she uttered beautiful little gusts of excitement that I can still hear even to this day.

When my cock couldn’t wait another second, I positioned myself behind her and slowly slid my erection inside. I bucked in and out of her, fucking her at an easy pace that stoked our lust. I especially loved doing her in that position because it left me admiring her awesome ass, which was among her best features.

Bella began rocking back against me, taking control of our pace and increasing the speed. I wrapped one arm around her waist to anchor her, and then used the fingers of my free hand to stimulate her clit. She rammed against me harder, wanting more and more of what I had to give. I did my best to meet her body’s  demands and felt a delirious sense of accomplishment when her orgasm hit and her body shivered beneath me. She only uttered a soft exclamation of joy, but I could feel the orgasmic energy flowing through her slender form.

Bella caught her breath and climbed on top of me, impaling herself on my unflagging erection. As she undulated above me, her tempting breasts hung before my face, and I struggled to lick her nipples as they passed by my mouth. It was like a sexy carnival game — one I never wanted to stop playing.

Bella told me she wanted to taste my cream, so we switched positions again. I sat back against the pillows while she crawled between my spread legs to take my glistening cock in her mouth. She sucked her sweet juices off my shaft and played with my balls until I was bubbling over with satisfaction. I jetted into her mouth, and she moaned as she swallowed down my load.

To my amazement, my erection did not falter. Bella was pleasantly surprised by that development and led me by my cock into her bedroom.

“Would you like to fuck my ass?” she whispered. Well, that’s not a usual thing for a first date, but my cock bobbed up and down affirmatively. We started with her on her hands and knees, as we had been before, only this time my cock was in her snug backdoor. After a while she got on top, sliding up and down on me. I enjoyed watching her asshole enveloping my manhood with each downward thrust.

When I told Bella I was close to coming, she picked up her pace. She slammed her ass down on me like a wild woman, grinding and writhing until she worked every last drop of cream out of my exhausted body. That was the first time in my life that I’d ever felt as if an orgasm has completely decimated me. It was thrilled experience.

I stayed the night with Bella and ended up extending my stay longer than I’d planned. From the beginning we could both tell this relationship was special, and after a couple months, I moved west and we’ve been together ever since.

No more Chicago winters forme — and no more cruising Route 66. I’ve found the pot of gold at the end of a rainbow.

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