Pump it on the Highway

It's a long way to go from Manhattan to Boston. Also a long way to cum. Some years ago, never mind how many, I worked in Boston and had a girl in Manhattan. Our relationship went on from mid-teens to 30-something, when I married someone else. I usually had another girl in Boston, sometimes two, but Martha was my sure thing. She was 5'3" and a track star in high school, small tits (but all there) and a gorgeous muscled ass which played a large part in my sex life: the only girl I ever knew who really loved anal, and came that way almost every time. Having Martha so available gave me a regular, healthy series of hardons and cums through my teens and 20s, which may be the reason I still consume all the Viagra (now Cialis) that I can afford every month. Sex is mind, muscle, and satisfying memories, and the sooner you start, the longer you'll go. My years with Martha involved a lot of traveling, and worth every mile. I like cars and usually had a beauty: a red TV with the 19" wires, a '49 Jaguar Mark IV drophead, a '56 Olds 98 convertible, and the best road car of all, a M-B 300S, a short chassis 2+2 softtop good for an honest 130 for an hour on the Maine Turnpike; also a AC Ace, a 2-litre aluminum-bodied Ferrari-red beauty that I raced on Northeastern road courses. . But sometimes I was between wheels, and when this story took place I was riding my thumb. I hitched back from Seattle one summer in college, and had only one bad ride, a middle-aged gentleman who started telling me about showering with athletes in high school, seeing their assholes when they bent to wash their legs, and getting a hardon. (I bailed out: I love most kinky sex, but I'm an unreconstructed hetero, and he clearly had me nominated as his inspiration, after the highschool quarterback.) After a weekend worshipping Martha's definitely female ass in a first-floor apartment on 22rd Street, my drill was to take the A train from 23rd to 185th about midnight and walk down Riverside to the edge of the Hudson under the giant roadway that arched the dark river to Jersey. It was Korea-time, and sailors on the West Side got picked up first, but I never had to wait more than 15 minutes. (The West Side Hiway is gone, a dangerous badly-paved serpent of an elevated roadway down the edge of the Hudson; I remember the crack ocean liners, lit like the Tivoli Gardens, stretching their bows over 10th Avenue, gone now like the hiway, but the massive roadway, lit like a stage set and arching over the dark river to Jersey is still in front of me.) That night it was one ride to Hartford and another who said he was going "near Boston", so I fell asleep. (Hitchhikers' rules: don't talk, don't drive, don't pay for gas, and if the tire blows, walk away and stick your thumb out again.) But crucial to efficient or even safe hitching is where you get off, and I stranded myself on this ride. When I heard the driver say, "I go west from here," I sat up and saw the hitchers's nightmare: an empty four-lane at 4 am on a frozen January and not a light in sight. I knew where I was: Route 2, 40 miles west of Boston. Well, you don't win 'em all; I bailed and found myself standing in a cold wind, wearing a light topcoat and desperate for a piss. As his taillights disappeared over the hill, I checked for oncoming headlights and pumped ship. It felt like a hot gallon; I was sore from Martha's eager squirming, and the cold actually felt pretty good on my raw skin, so I left it out, holding the topcoat over my cock with my left hand like a flasher and thumbing busily when a solitary car would come by heading east. The cold stimulated me: I zipped down further and lifted my balls out to the wind, my cock starting to come to attention. Of course this took my mind back to Martha: we were into anal, and had two active sessions during the weekend. I remembered my cocktip pressing against her asshole, her tight little ring of muscle suddenly loosening and I went inside that soft, warm, endless grainy hole that is so different from a cunt. I've always been an ass man, and the memory of Martha's muscular buttocks and full womanly hips, my hands gripping her little trim waist, my cock forcing deeper into her warm gut, her tight ring of muscle gripping further and further down my cock gave me one great hardon out there on the highway in the dark. I really didn't know if I had another shot in the locker after the weekend workout, but I had to try. Standing there by the roadside in the dark with no lights anywhere in sight, no houses, no gas stations, a moonless night with lots of stars, I had to get off with this boner. Every time it swelled a little more, I thought of Martha's ass, and every time I remembered her ass cheeks pressing back around my cock, it grew some more. I started fisting myself harder, and felt the juice pumping into the bottom of my balls. In the dark, I loosened my belt, opened my trousers, pulled down the elastic of my shorts and let it all hang out. I was beating my meat in the dark with a steady rhythm that promised to bring me off, a powerful erection that tightened my butt cheeks and my asshole. It wasn't a quick one: my weekend with Martha had taken some skin sensitivity and a good portion of juice, but there seemed to be plenty of both left deep in that thick muscle. I thanked the Almighty God of all masturbators for his gifts.. The glow of headlights appeared beyond the hill to the west, and I kept fucking my fingers until the lights came up on me, then wrapped the topcoat around with my left hand, put my right through the slit pocket, and kept fingering that sweet spot where the foreskin connects. I was getting ready to squirt, and the last thing I wanted right then was a ride! The guy shot past, paying no attention, and I got back to the serious business of coming onto the black, empty road. No headlights anywhere! I dropped my pants and shorts, hitched the topcoat around my waist, and stood there naked from ass to ankles, knees bent and apart, jerking off in the cold wind. It felt fantastic! The juice was starting to pump up higher when headlights appeared again in the west. I bent down, pulled up my pants and held the topcoat together. Come on, I thought, don't be a good Samaritan, I'm just another mild-mannered pervert beating off in the dark, keep driving. He did. Dark again everywhere, except his red taillights shrinking towards Boston. My ass had goosebumps from the cold wind and I admired my cock standing out by starlight, two inches beyond my thumb, bigger than I could remember it and thicker too, unless the cold had shrunk my fingers. I picked up the tempo, and felt precum making me slippery. Definitely on the way. I collected thick spit, drooled it into my palm and turned up the beat. I passed the Tantric point, no turning back, and more headlights came, this time from the other direction. It was a divided highway, and his lights weren't shining on me. I was breathing deep, my cock filled to bursting, jacking away fast. I started to come just before the car camed past, one of those shuddering great orgasms that come right up from your asshole and drain your spine, jetting out onto the black highway again and again, a very satisfying finish deep in Martha's ass and squirting out under the stars at the same time. For a long time, I was in that nice afterglow when you could go to sleep on nails or freeze to death, and then I breathed again. Headlights glowed from the west; I bent for my pants and shorts together and got them up and organized enough to wave my thumb.

The driver was going to Boston, right to Beacon Hill. He cranked up the heater and said, "Warm up. I'll tell you when we get near Boston." He was as good as his word. He left me at the door of my red brick apartment building ($55 a month, and clean). I tottered up three flights, stripped and showered. When the hot water hit my cock, damned if it didn't start to erect again, and I soaped up and gave it one more try. The engine turned over real cranky and then caught and we were off. My cream (not so much, but a good effort) squirted and splattered on the wall of the shower stall, and I had to stop my mental massage of Martha's rectum, wrap myself in the coverlet and I was out in seconds. I slept through the alarm clock, jogged over Beacon Hill and through the Common, ignored a hairy eyeball from the assistant city editor, sat at the typewriter and started on a bunch of rewrite stuck under the bail. That night I called Martha, and my luck! she wanted phone sex! I couldn't handle it, and managed to convince her that she had wasted me so the night before that the well had to fill again.

And it was true enough, if not entirely the way she imagined. So she let me have a rain check, and I got to use it two weekends later in the first-floor on 22nd St. I think by then I had a car again.