Too Much of a Good Thing

‘Looking for a rideshare to San Fran. Can leave any time. Will split gas and tolls.’

I posted it the old-fashioned way, with a thumbtack on an old-fashioned bulletin board, because I’m an old-fashioned kind of guy.

Within a week, I got a response. Alyssa was driving across the country and wanted company. She sent me an email with a barrage of questions, some of which were pretty personal, and a lot of which seemed totally irrelevant; and she asked me to include a picture with my answers. I filled out her questionnaire and sent her a photo of myself; a couple hours later she said I’d do. She told me she was planning on taking her time, staying off the major roads as much as possible, making the coast-to-coast journey in a week or ten days or so. That was fine by me. She sounded cute. I figured I’d just hit the jackpot.

I met her on 8th avenue, over by the Port Authority, my overstuffed backpack slung over my shoulder. She was driving a little brown Honda that looked like it had seen better days.

“Get in” she said, and grinned, showing off two rows of perfect, sharp little teeth. She had frizzy brown hair, speckled with grey, freckles on her cheeks, and little crow’s feet in the corners or her eyes that showed whenever she smiled.

I got in. Alyssa must have stood a full head shorter than me, but she radiated a ferocious energy, like a pretty wolverine. I wouldn’t have wanted to tangle with her. All her features seemed to be sharp and pointy, and her slate blue eyes flashed dangerously in the morning sunlight. She was older than me, it’s hard to say how much, I’m lousy at that; at least ten years, maybe more. I sat down in the passenger seat next to her and buckled up as she pulled out into traffic.

There wasn’t much small talk as she deftly maneuvered the little car through the crowded corridors of midtown; traffic was heavy. As we inched our way toward the entrance to the Lincoln Tunnel, she placed her right hand lightly but decisively on my thigh. Inside my jeans, my cock snapped rigidly to attention.

Well. This was certainly going to be an interesting car trip.

By the time we emerged into New Jersey, Alyssa had fished my dick out of my pants, and was happily playing with my cock, petting it like a playful puppy.

“Why don’t you take off your jeans, Boy-O?” she said, “They’re only getting in the way.”

I was happy to comply, kicking off my pants and my underwear, sitting nude from the waist down as we sped along the Jersey Turnpike, my cock pointing eagerly up like a flagpole.

“Much better,” Alyssa said, and smiled sweetly. She set the cruise control at 65, and got down to the serious business of jerking me off, her thumb and forefinger wrapped around my erection, stroking constantly, sometimes fast and sometimes slow; sometimes squeezing me tight and sometimes barely touching my aching flesh.

“Let me know before you come.” she told me, and after fifteen or twenty minutes of exquisite torture, I yelped out that I was about to blow.

“Here, take the wheel!” she commanded, and before I could protest, she had dropped her head into my lap, opened up her thin red lips, and swallowed the top half of my cock whole, cupping my balls tightly with one  hand while she deftly jerked me off with the other.

I managed to keep the car on the road, though I swerved like a drunk all over three lanes of traffic as I came, lifting my ass up off the seat and pumping what seemed like gallon after gallon of semen into her incessantly sucking, insatiable mouth. She stayed with me all the way through, swallowing every drop of my come and leaving my dick wet, soft, and tired.

Finally she came back up for air, taking the steering wheel back from my shaking hands.

“Mmmm. Oh yeah Boy-O, that was delicious. I’ll never get tired of that stuff! No, leave your pants off. I like you better that way. I’m married, by the way. I hope that isn’t a problem for you.”

I hadn’t noticed the gold ring on her finger before. It wasn’t a problem for me.

She chose an exit, seemingly at random, and we pulled off the interstate and onto the rolling back roads of Pennsylvania farm country. As we drove, she toyed idly with my dick, which slowly rose back into a state of erect excitement.

“Not bad, not bad at all.” she said, “Why don’t we stop right here?”

We pulled off at a wide place in the road next to a farmer’s fields. Brown cows watched us incuriously as we got out of the car and stretched our legs. I sat on the trunk and Alyssa bent over and started giving me an expert blowjob.

“Don’t hold back,” she said, “we’ve got plenty more driving to do. Would this help?” She pulled up her top and unsnapped her bra, exposing a pert pair of smallish, lightly freckled breasts with pink, pointy nipples. They jiggled nicely every time she moved.

A semi-truck blew by and honked his horn appreciatively. Alyssa buried her face in my crotch, swallowing most of my dick, bobbing up and down on me and swirling her tongue round and around my shaft, licking the ridges of my head and slurping at the underside. It didn’t take me too long before I was humping back at her pretty face, fucking her mouth, coming once again, moaning and shouting out loud in the warm open air, filling her mouth with my semen.

We got back on the road, making our way along lazy country roads, sometimes making wrong turns and having to backtrack; but generally heading south and west. Alyssa had me strip nude in the passenger seat next to her. She said I looked cute that way. She let me put a t-shirt on when we stopped for gas, and I got fully dressed when we stopped for lunch at a greasy-spoon diner in the middle of nowhere. She didn’t ask me to pay for either the gas or the food, and I didn’t offer.

She played with my cock and balls from time to time as we drove. It seemed to amuse her no end to make me hard and then to watch me wilt all over again.

Our first day’s drive ended at a hotel somewhere outside of Parkersburg. It was a way nicer hotel than I would have picked, but then again, I hadn’t paid for any of the gas or tolls, and Alyssa had bought me lunch. I half-expected her to get a room for the both of us, but she got her own room, and I ponied up the credit card and got a room for myself. We got our stuff our of Alyssa’s decrepit Honda, and then we went our separate ways.

I took a very hot shower and ordered a pizza and sat on my bed, watching stupid tv and feeling kind of numb. It had been quite a day, a lot of driving, and a lot of stimulations, and I felt a little bit shell-shocked.

There was a knock on my door. It was Alyssa, in a blue denim dress. She sat on the edge of the bed, and I gave her a foot massage for the better part of an hour while she chatted with her husband on the phone. That’s a long time to rub someone’s feet, and my hands started to get tired, but every time I started to think about quitting, Alyssa gave me a sharp look that made me change my mind and got me right back on task.

Every now and then, as I massaged her petite feet, I’d catch a glimpse of her skimpy green panties up her skirt. Toward the end of the conversation, she hiked up her dress, and slid her fingers up underneath her panties. Inside my pants, my cock was straining hard.

Finally, she hung up the phone. “Why are you not naked yet?” she asked.

I hurriedly got undressed as she pulled off her blue dress and stripped out of her bra and panties. She had a lovely, taut little body, with a mostly flat tummy, curvaceous hips, and short but thick, almost stubby thighs. Her breasts seemed perfect for her frame, small and pert; and her pussy was crowned with a neat little triangle of dark, curly hair. She lay back on the bed, spreading her legs wide, opening her pussy with two fingers. The inner lips were delicate-looking, small, pink, and wet.

“Saddle up, Cowboy!”

Feeling kind of awkward, I rolled on a condom and climbed on top of her, slipping my erection straight up her eagerly salivating hole.

She was shockingly hot inside, tight, wet, and slippery. Her pussy felt amazing on my cock. Right away she grabbed my ass with both hands and pulled me deeper inside.

“Fuck me! Fuck me hard, Boy-O! Harder!”

I complied, fucking her little pussy with a vengeance, as hard and as deep as I was able. She loved it, bucking back against every stroke, her hands on my ass cheeks pulling me insistently deeper, hissing encouragement through clenched teeth. In other circumstances, I would have had to fight to not come right away; but since I had already gotten off twice already that day (three times if you counted my late night/early morning masturbation session), I was in no danger of shooting off early.

“Harder! Faster! Harder, damn you, harder!” She was writhing underneath me, squirming and wiggling, arching her back and lolling her neck from side to side, every muscle in her face clenched. I knew she was right on the edge. Breathing hard, my heart pounding inside my chest, I complied, fucking her with everything I had, until my muscles were quivering and sweat was running down my face.

When she came, it was a beautiful sight. She threw her head back, and her whole chest flushed mottled red. I could feel her pussy spasmodically squeezing my cock, her abdomen shook as every muscle clenched and relaxed, and she screamed loud enough to let everyone in that hotel know exactly how good her orgasm felt.

I was glowing. I felt like I had just run a 10k, and fast. I fucked her a little more, but we were both pretty exhausted, so I ended up pulling out and removing the condom and jerking off into her open mouth, which she seemed to appreciate.

Then she got dressed and went back to her own room, leaving me to my tv and my congealing pizza. I crashed out hard, and didn’t dream.

We hit the road the next morning, nice and early, right after breakfast. Alyssa was all smiley and cheerful and chipper. The character of the land had changed, we were in distinctly Midwestern territory now, driving past farmland that seemed to go on for miles, interspersed with colonies of McMansions, sprouting up like toadstools.

“Come on Boy-O,” Alyssa said, “You know how I like to see you. Nude and lewd. Lose the clothes.”

I dutifully stripped, and Alyssa reached right over and started squeezing my dick.

“Are you serious?” I asked, “Again? Already?”

She raised an arch eyebrow at me. “You’re not complaining are you Boy-O? ‘Cause you can always get out and start walking.”

I wasn’t complaining. And soon enough my dick was bobbing merrily up and down, hard as a dry stick, and I was squirming in the seat as her hand pumped up and down.

She had me take the wheel while she blew me for a while, but thought her mouth was talented, and it felt glorious, she wasn’t able to make me come that way. So she pulled the car off onto the shoulder and had me get out and stand behind the door as she knelt in front of me, licking my balls and working her tongue up between my butt cheeks as she jerked me off. It took a little while, but she knew what she was doing, and the orgasm was well worth the wait. Her hand was a blur, and her tongue was brushing up against my asshole, and I finally came, spattering semen into her waiting palm. She licked it all up, like a hungry cat, and we resumed our drive.

After lunch, in the parking lot of some small-town diner, she climbed into the back seat and pulled down her pants. She told me to jerk off onto her pussy while she masturbated, and I did, crouched in front of her crotch, pumping my own cock hard and fast as she fingered her pink little clit. I kept having visions of a small-town sheriff tapping on the window, and that motivated me to get off as quickly as I could. Seeing my pearly-white come splashing on her pouting pussy lips seemed to set her off, and she came with a long, drawn-out yawning groan and a satisfied smirk.

Another hotel, once again outside of my price range, but since I wasn’t paying for gas, I figured it kind of equaled out. I rubbed her shoulders while she talked to her husband on the phone, and then she went down on me. Nothing happened. I was kind of mortified; I wasn’t used to getting anything like this much attention, but still, I had always been up and ready for any action that came my way.

Alyssa didn’t appear to be too concerned. If anything, she seemed mildly annoyed, as if her car had developed a minor mechanical problem that would necessitate an unplanned stop. New wiper blades, for instance.

She had me lay on my back on the hotel bed, and licked my body all over, starting with my neck, pausing at my nipples, and working her way down from there. My dick stayed stubbornly soft as she licked it like a big wet noodle. She nudged my thighs apart, licking and sucking my balls exquisitely, and then pushed my knees back and started licking my ass, dragging her tongue up and down my crack, pressing her tongue against my anus.

It felt amazing, and I started to feel a tell-tale tingling in my cock. She was fingering her pussy as she licked my asshole, and it was almost too sexy for words. Then, without so much as a by-your-leave, she slipped a wet finger straight up my ass.

I yelped, and she giggled. It didn’t hurt. It felt weird. She was moving her finger around in there, making little beckoning motions. If it wasn’t exactly pleasurable, it certainly wasn’t unpleasant either. And my cock responded right away, rising tall and stiff, like a circus tent pole.

She withdrew her invading finger, leaving me feeling tingly and hollow; tossed me a condom, and climbed on board for the ride. She bounced up and down on my dick, grinding her pubes against mine until she came. Then she clambered off, removed the condom, and told me to masturbate into her mouth. I dutifully did as I was told, but I just couldn’t bring myself off. I whacked off until my toes curled and my ass cramped, but I couldn’t quite push myself past the threshold. Eventually she left me there in the hotel room, hard, sore, and frustrated.

We were worming our way into the American Heartland, long stretches of two-lane back road winding through industrial-sized fields of soy, wheat, and corn. I sat naked next to her as she drove, leaning back in the seat and enjoying my morning hand/blow job. Once again, I came in her mouth, and once again she slurped it all up and wrung me out like a damp sponge.

It was a frustrating day of driving; construction, wrong turns, backtracking, and pokey local traffic. Several times I offered to take a turn behind the wheel, but Alyssa curtly turned me down.

“It’s my damn car, and I’ll do the driving, thank you. Your job, Boy-O, is to sit there and look good.”

So I did. She played with my dick on and off all day, sometimes even handing me the wheel and having me steer for a while she sucked on me for a few miles, but never bringing me to orgasm, or anywhere even close. At one point we pulled off the road, and she had me fuck her face, holding the back of her head and jamming my cock down her throat until she choked and coughed, but I still couldn’t come, which seemed to annoy her.

We seemed to have ended up in the absolute middle of nowheresville. It was one giant strip mall, with plenty of Wallmarts, used car dealerships, and hot-tub outlets, but not a decent hotel to be found. It was getting dark before Alyssa finally settled on a dingy-looking Motel 6. She may not have been thrilled about the place, but I wasn’t complaining. This joint was much more in line with my own personal budget.

After checking in, we each made our own separate way over to the bar that shared a parking lot with our motel. I took a corner table and ordered a beer and started reading one of the books I had brought along, a Jack Kerouac road-trip novel. It was the first time I had so much as opened a book the whole journey.

As I sipped my beer, I observed Alyssa in action over at the bar, chatting up one of the locals. The object of her flirtation was a heavy-set blonde guy in a grey suit, who looked like he might sell tractor tires for a living. I felt an odd mixture of jealousy and relief as I watched her put the moves on him. She was, of course, free to do as she pleased; and frankly I could use the break.

It was after midnight when Alyssa rapped on my door. She smelled of whiskey and cigarette smoke, and her curly mop of hair was wayward and disheveled. She pushed her way into the room, rubbing her body against mine.

“He had a pretty big dick,” she said, “but he had no idea how to use it. Oaf. Pretty useless. He lasted all of about thirty seconds. I didn’t even get to taste a single drop.” She added petulantly.

Alyssa shrugged off her floral summer dress, which cascaded into a heap around her ankles. She wasn’t wearing anything underneath. She lay down on her back on my bed and spread her legs wide apart, and I got down between her thick, stumpy thighs and started licking her pussy.

She was very wet, salty and musky and delicious. Her pussy was freshly fucked, relaxed and open and squishy. I really enjoyed going down on her, dragging my tongue up and down her vulva, nibbling at her lips, flicking my tongue at her erect little clit. She seemed to enjoy it too, rubbing back against my face and making appreciative noises; but all too soon she pulled away from me.

“Thank you, that was nice,” she said, “But I really need to feel you inside me. Not my pussy; it’s too tender right now. Fuck my ass.”

It was not an invitation I’d ever received before, though it was something I’d always wanted to try. She rolled over and got on her hands and knees on the bed, her rump thrust lewdly up in the air.

“Do you have any lube?” I asked dumbly, my cock sticking straight out from my crotch like the bowsprit of a sailing ship.

“Use spit,” Alyssa told me, “That’ll work, if you use a lot of it.”

I stuck my face between her pretty ass-cheeks and started licking.

Her asshole was a tiny little button, crinkled and tight. I teased it with the tip of my tongue, eliciting a throaty sigh and a groan. She tasted clean and earthy. I lapped at her ass with the flat of my tongue, spreading spit all over back there as she fingered herself. Her juice mixed with my saliva, and I drilled my tongue up into her anus. I was getting really into it when she interrupted me.

“That should do it, Boy-O. Fuck my ass now.”

I repositioned myself and took careful aim. I wasn’t sure how my dick was going to fit into that teensy little hole. I pressed the bulbous red head of my cock against her tiny asshole, and carefully nudged forward. Amazingly, she opened right up and accepted my dick. The head of my cock slid right up inside her and she grunted.

She was tight, insanely tight. It was like trying to fuck a clenched fist. Her sphincter muscles formed a ring, squeezing my shaft as my dick invaded her ass, slipping gradually deeper and deeper up her butt.

“Don’t… be… so… uh… fucking gentle!” she growled at me through clenched teeth, wiggling her ass and pressing back hard against me.

I started fucking her ass in earnest, abandoning myself to the pleasure of it, casting off all restraint. She grunted with each thrust as if she were getting punched in the gut. Her fingers were squishing loudly between her legs as she masturbated furiously.

I wasn’t going to be able to last much longer, and I started fucking her ass hard and deep, howling out loud, and she joined me, baying like a she-wolf. She came, her entire body going rigid underneath me, and that set me off. I slammed into her one last time, my cock twitching and pumping hot sticky semen straight up her butt. Then I collapsed on top of her, and we lay there for a while, breathing hard, our hot, sweaty flesh pressed together, my soft, leaking cock captured by her ass.

“Thanks,” she said at last, “I needed that.”

She extracted herself and pulled on her sundress, and left me lying there, a tired and sweaty-sticky heap.

I slept hard that night.

Alyssa woke me up early the next morning, looking to take advantage of my morning wood. She climbed naked into bed with me, and had me straddle her chest and rub my dick between her tits while she masturbated. It felt nice, and it looked incredibly sexy, my hard cock sliding up and down between her perky, freckled tits, while she craned her neck down for a lick or two, her fingers busily strumming between her legs.

Then, without warning, she jammed a finger (or two!) up my asshole, all the way up to the knuckles. I jumped and yelped, and suddenly I was coming, squirting all over her chest and neck and tits. It actually hurt when I came, as if Alyssa was making lemonade, and I was an used-up lemon that she was wringing every last drop of juice from.

She laughed merrily and wiped up my splattered semen with her finger and licked her finger clean, and we got dressed and had breakfast and hit the road.

She played with my cock in the car, but I stayed persistently soft, even when she took me in her mouth and sucked on me like a strand of spaghetti, swirling her tongue all around the crown, and even reaching underneath me and tickling my asshole.

“Are we going to have to put you on the little blue pills?” she asked crossly.

My dick was tender and a little raw from all the fucking and sucking, and my balls ached, a deep-down worn-out ache.

“Can we just give it a little rest?” I asked, “I’m not a dildo. I’m not your own personal sex toy.”

She swerved to the side of the road, stomping on the brakes hard enough to make as skid a little on the gravel shoulder.

“Was that a complaint? Are you complaining, Boy-O?”

Without a word, I gathered up my clothes and took my backpack and climbed out of the car, feeling her slate-blue eyes burning into my flesh like James Bond lasers. As soon as I was out, she slammed the Honda into drive and pulled away with squealing tires, disappearing after a few seconds over a low hill up ahead, the sound of her engine slowy fading away.

Feeling shaky and rattly, like a dried-out husk blowing in the wind, I got dressed a few steps into the field, surrounded by a dense forest of cornstalks that loomed taller than me. Stepping back onto the side of the road, I shouldered my backpack and started to walk.


1 Comment »

  1. ElsieFanny said

    Thank you hon for another great story. A believable story about a guy who has too much sex for his own taste is impressive. What is so much better is the way that you switch around the married guy who is using the sweet young thing for his own pleasure without any care for her feelings into the same relationship with the genders reversed.

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