Sex and the Single Sidecar

My buddy Art had retired early, at sixty, and I'd taken one of the buyouts from the East Coast daily newspaper I'd written for, as its third absentee owners "cut fat" — then cut muscle, then bone.

Art had forked out big bucks to have a gorgeous '65 Triumph Bonneville restored, with its chrome lustrous and shiny new gold-and-cream paint. I'd done some of the work myself on a BMW R60/2 of the same vintage, but soon realized I was in over my head and turned over part of my retirement to a professional to have it brought to like-new condition mechanically, adding new red leather on the sidecar seat and pinstriping on the fresh glossy black paint.

So after a long, cold winter of California dreaming and a summer of planning, interrupted by odd jobs, we were a couple of geezers on a tear, looking for our lost sugar and salt on the open road.

With chambray under our leathers, vintage denim beneath our chaps and bandanas under our brain buckets, we headed west from Philly on the Pennsylvania Turnpike. I should mention our third musketeer: Lucky, Art's Jack Russell, wearing goggles and a red bandana round his neck, rode majestically in the sidecar.

On the warm September afternoon we luxuriated in the pike's sweeping curves between Appalachian mountain vistas already tinged with flashes of fall reds, oranges and rusts. The plan was to head west to Columbus, then to St. Louis and pick up old Route 66. Yep, we're boomers, and grew up with that TV show burned into our brains.

We were swaggering proof that there's only a few decades between cool and fool.

By Wheeling, West Virginia, the romance was done for the day. Our butts hurt. We found a dog-friendly motel and gratefully creaked off the bikes.

Lucky was overjoyed — our couple of coffee breaks must've seemed few and far between for a pooch so dedicated to reading his pee-mail at every stop. Leaping from the sidecar at the motel, he took himself for a royal romp through the empty lot out back, rolling in the dust, snapping at grasshoppers and jumping just for the hell of it.

We grabbed an unmemorable bite at a nearby greasy spoon and turned in, pretty well oblivious to the lumpy beds and musty room. The pup curled up on the only easy chair and was snoring in seconds.

In the morning we sluiced off in the mildewed shower, fed the dog and prepared to hit the road. The girl serving coffee gave us a wink — well, she was a "girl" to us, more like a MILF in her forties and that after a good night's sleep — and we grinned. Maybe there was hope for us yet.

"At least we can say we got Lucky today," Art joked as we straddled the bikes, the Jack Russell jumped aboard and we fired up and wheeled west.

That afternoon we decided to give our bodies a rest and called an early halt in Columbus.

We found a slightly better motel where the young woman behind the desk took a shine to Lucky, and turned the "No Pets" sign on the counter face down. Her shift was over in a few minutes, and she knocked on the door to our room and asked if she could take the dog for a romp; she lived near by and thought her Mom would think he was cute.

Art and I fell onto the twin beds, and were down for the count moments later: ah, the luxury of an afternoon nap after a day winding through the mountains on two (or three) wheels!

A while later there was a knock on the door and a short bark. Lucky was back.

We opened the door, looked down and saw his inquisitive nose and furiously wagging tail. Then a pair of slightly dusty spike heels on very shapely legs. Our reaction must've been comical: our eyes moved in unison up the legs, up and up to a navy miniskirt, revealing silky scarlet blouse, long neck and big grin.

"Hi, I'm Kris. My daughter said I could bring Lucky back to you two fellers. She thought I'd like to meet you."

We'd fallen asleep in our chaps, and her glance went boldly from face to face to crotch to crotch — and back.

"Yes, ma'am," we croaked in unison.

A petite redhead of maybe fifty, Kris obviously took care of herself and spent time at the gym or jogging. She was a knockout: flashing eyes, pert nose, stylishly short hair, gentle curves with a hint of lace at her bosom, tight skirt outlining two handfuls of lovely round ass, long legs to die for.

She leaned provocatively against the doorway. "You must be hungry. There's a place a couple of miles from here with good home cooking. Does that sidecar hold girls, or just dogs?"

Didn't take us long to brush our teeth and hair and settle Lucky in the room, and out we went. She took off one shoe, stepped one leg into the sidecar and settled her bottom, stretching the other leg toward me to take off its stiletto. The navy skirt stretched obligingly and I got a instant hard-on from the slow-motion flash of dark red silk panties stretched tight between puffy lips covered with a down of trimmed, rust-colored hair.

She chortled merrily as I readjusted my bits so as not to wreck myself when I got on the bike, then she eyed Art's chaps as he swung his leg across the Triumph.

Kris's taste in food was more sophisticated than her taste in bike-riding geezers. The meal was wonderful: home cooking, sure. As you might find it in Provence or Tuscany. The freshest of everything. Buttery but light. Perfectly matched wines. Afterward, espresso that was fragrant perfection in a demitasse.

I hadn't expected this kind of luxury in Columbus, and was in no hurry for the meal to end. But finally it had to. Art and I split the check, but Kris slapped down a third of the cash. No way, she said. We cleared out throats to argue. She pouted, looked at our chagrined faces, and laughed.

The maitre d' picked up the cash, with a handsome tip, and Kris laughed, low and throaty. "Take me home. You'll pay up there."

She climbed into the sidecar, handing me her heels. I was sorry the parking lot was dark.

A few twists and turns, and our rumbling bikes pulled into a secluded driveway in front of an old frame house with a porch light glowing through the mist. It felt a bit like the setting for a Faulkner novel, and I briefly imagined this might turning into a Southern Gothic misadventure.

But inside all was bright pastels, a modern kitchen and comfortable, fashionable furniture. Art asked about her daughter, and she said she spent most nights with a boyfriend a few houses down the road.

"Make yourselves comfortable, boys, while I fix us a nightcap."

We'd doffed our leather jackets and boots by the time Kris got back carrying a silver tray with Scotch, bourbon, ice and a soda siphon. Glasses were filled and clinked, sips were taken.

"Now that I've broken the ice, so to speak, those chaps have got to be mighty constricting," she said, standing between us. "First, would y'all help me out here?"

She was reaching around to the small zipper at the back of her blouse. A gentleman couldn't say no, so I lowered it for her.

"Thanks. That's so much better."

The blouse fell away. Underneath was a darker red, lacy camisole.

"Now, Art, this one please." She backed toward him, he pulled the zipper. The navy skirt fell to the floor.

She stood in her heels, clad in dark red silk — hard nipples jutting from her small, perfect breasts, and a softness at her mound hinting at a trimmed bush.

"I see we need to get those chaps off, fellas. Can yah do it yerselves or do you need my help?"

My mouth was too dry to answer, so she dropped to her knees on the broadloom, unlaced my chaps, loosened them, then unbuckled my belt and pulled down my jeans as well.

My raging hard-on tented my Jockeys. She smiled.

"Art, you better keep up," she laughed. He obliged as fast as he could.

She pulled my underwear down to my thighs, circled her long, elegant fingers around my cock and kissed the head warmly.

"Over here, Art. You're missing out," she cooed.

He stepped out of his pants and stood in front of me. With a cock in each hand she pulled us together and slid her tongue languidly from one to another across the most sensitive spot right underneath the head, looking up coquettishly. Just when I thought I couldn't hold on any longer and was about to spurt three weeks of cum over her face, she left us in midair, stood up and strolled to the sideboard.

Holding a Susan B. Anthony between thumb and forefinger, she arched an eyebrow. "Heads or tails?"

"Tails," I said. Art nodded. "Heads."

She stood in front of Art, back to me, and raised her arms. "Heads: Take it off. Enjoy."

She turned slightly as he obliged, so I got to watch the camisole rising slowly up her belly, gradually exposing her breasts. There was a slight tug and a little snap as the last stretchy silk jumped over her long, hard nipples. I nearly came right then.

One step and she was facing me. "On your knees, Mr. Tails. And go slow."

I slid the lacy dark red panties down her buttocks and saw Art's thick dick jump to attention. I held my breath as I lowered the front.

My cock throbbed almost painfully between my legs as her lovingly manicured rust-colored bush hove into view at eye level. I moved as slowly as I could, breathing in her fragrance and savoring the sound of silk sliding over tight flesh. When I reached mid-thigh, she held up her hand. She took a step back and moved her feet apart, stretching the maroon silk and exposing her hard clitoris, which was nearly as prominent as her nipples.

"Well, I guess I can't call y'all 'boys' anymore," she drawled, as the three of us stood there in a triangle with our underwear to our knees and erectile tissues in full glory. "Time t' come along an' go all the way!"

Her bedroom was feminine but not frilly: king-sized bed, handmade windowpane quilt, tasteful curtains and dressers. She whisked away the quilt and sat on the dark red sheet, pulling off her panties. "Y'all think yah can get it up more than once? I have the thought your first time's gonna be quick."

We nodded, pretty well mute, as she lay back with her heels on the sheet, showing off her glorious pussy. My body'd been hijacked by the one-eyed trouser snake, and I followed it to kneel between her legs.

Oh. My. God. That's one enthusiastic woman, I thought as I slipped in. I plunged and rammed and thrust and reamed, and could see Art jerking his dick enthusiastically as my balls slapped her perfect ass and ...

"You stop that!" Art stopped in mid-pull. "Take your hand away from that cock!"

Kris was nothing if not clear with her orders.

"Now you. Slow down." Okay, I got it. She grinned and gripped my hips, setting up a deep rhythm of penetration ... withdrawal ... penetration ... withdrawal.

The slow grind was hotter, if possible, than my jack-rabbit fucking, and moments later I loaded her pussy with my pent-up penis-juice.

Gently, she rolled me off and welcomed Art to her version of heaven: "Hi angel, come to Cloud Nine."

I watched his thick dick moving slowly, mesmerized as its prominent head pulled gouts of my semen out of her with each stroke till suddenly his balls jerked three times and his load joined mine.

"Ahhhhh." She rubbed her clitoris between her first and middle fingers, our mingled sperm lubricating her as she masturbated with her magnificent legs lifted in some Pilates vee. She watched us to see how long her show would take to raise the recently dead, and smiled happily when it had the desired effect.

"Hungry, gentlemen?" We took turns licking that eager clitoris as her chest heaved with gasps and murmurs until suddenly I felt my ears crushed in the vise of her thighs and she cried "Yes! Yes-yes-yes-yes-yes-yes. YES!" and a salty flood bathed my tongue.

By now Art and I were painfully hard once more, but Kris got up and returned with full glasses. A few sips of bourbon and soda revived us, as she caught her breath with Scotch. Leaning against the dresser, she signalled Art to lie down on his back. A tube of lube appeared, and she massaged a generous handful on my rock-hard penis.

She leaned over Art, kissed him tenderly and straddled him. Reaching behind her, she wrapped her long fingers around his erection, lifted it and slid back, burying him to the balls in one smooth motion. He groaned with pleasure.

"Stay still now, honey." She beckoned to me, and then pointed to her tiny, puckered rosebud of an asshole.

Now I'm not huge, but not tiny either, and that looked impossibly tight. I didn't want to hurt her.

"Don't be shy. I'm not a virgin there either," she said with her sexy, throaty laugh.

Art moved his legs apart and I knelt between his knees, putting the head of my cock at her tiny opening. I hesitated ...

"Don't be a ninny," she said. "Here, squeeze my nipples between your fingers."

She arched her back so her fragrant hair was in my nose. My hands grabbed her small, tight boobs and her hard nipples stuck out between my fingers. I squeezed. She reached behind me, grabbed my ass ... and stuck her nails in, hard.

"Ooof!" I wasn't expecting that. Reflexively I pushed forward and the head of my cock popped her Friday night cherry, merry as you please. Her ass was tight but the lube did its job and a couple of strokes had me all the way in.

It was the first time I'd had my cock in a woman who had another cock in her, and I guessed it was new to Art as well. She coached us first to stay still, to feel the wonder of three pulses beating together, then to move to each other's rhythm: one in, one out, till she got closer to her orgasm and breathed, heavily, "Okay, bang me both together now ... in, and again ... in, and again ... in ... in ... in ... NOW! Yes-yes-yes-yes-yes-yes. Cum now! YESSSSS!" And in a melee of gasping, thrusting, shuddering spasms, Art and I blew our loads into our multiorgasmic goddess's orifices.

Eventually we softened, and as we each slipped out Kris uttered a wistful little "Oh!" and stretched on the slippery, soaked sheets.

We cuddled for a while, then Art got dressed and left to take Lucky for a walk. I stayed for a while, chatting about everything and nothing — food, work, the open road, my life and hers — and finally, with an almost chaste goodnight kiss, she watched from her porch as I fired up the R60, and blew me a kiss when I kicked it in gear.

As I rode back to the motel, I wondered if this would turn out to be the most memorable night of the trip. I couldn't imagine anything that would top it.

The next few days were uneventful. We took it easy — we were both winded after that night with Kris. We didn't talk much, both pondering our own thoughts about what had happened. Frankly, the only one whose mood didn't dip was the irrepressible Lucky.

We stopped late one afternoon near Tulsa, Oklahoma. There were spectacular clouds in the big plains sky and a little diner and a motel, and we decided to grab a coffee and some photos as the sun set over the sandbars in the Arkansas River.

We checked into the motel, promising the gloomy, lank-haired, pimply young man behind the counter that Lucky wouldn't be a problem. With a half-hour till sunset, we went to the almost-empty diner in search of coffee.

The young waitress standing with her back to us at the counter was slim, with tanned arms and legs under the shapeless yellow restaurant-issue jumper. Her light brown hair, sun-streaked with gold and shiny from morning-and-night brushing, came half-way down her back. She stood like a young filly in the golden late-afternoon light.

We called her over to the booth.

I noticed her white teeth and lop-sided smile, the way her hair fell across one eye. My blood pressure rose dangerously: she reminded me of my first flame, the girl I loved and lost right after college. She'd been nineteen and I was a ripe old twenty-two; she gave me her virginity and I gave her my heart on a platter. When she dumped me a year later I was devastated, never really got over it.

She took our order, loped over to the counter, filled two cups from the coffee machine and brought them over with a smile. "Do you want anything with that?"

God, she even sounded like that girl! Same perfume, too. My heart was fluttering in my throat and I could feel I was blushing under my windburn. Art eyed me appraisingly.

"Bit young, don't you think," he said after she went back to the counter. "I'm not thinking that!" I said. He raised an eyebrow. "You never know when a chick may have a Daddy complex." He laughed. "Or more like a Grandpa thing, in your case."

I snorted.

But when she handed me the check she'd written on the back: "I'm off in an hour. You're in the room with the bikes outside, right?"

My hand was trembling as I handed her a couple of small bills. She made eye contact. Yes, I mouthed silently.

I took some digital photos of the sunset, but they didn't do the sky or scenery justice. And they weren't sharp. I should've used a tripod I guess. Didn't realize I was shaking that much.

Leaving Art out by the river, I went back to the room, feeling like an old fool. I couldn't tell you whether I hoped more that she would come ... or that she wouldn't. It was really too spooky how much she resembled that girl from so long ago.

Just when I heaved a sigh of relief that she wasn't going to show up, there was a hesitant knock on the door. I opened it and she slipped in.

She'd changed out of the baggy waitress uniform into what looked to me like date-night duds: A soft gray blouse, dark pencil skirt, knee socks, stylish but sensible shoes. She wore a rakishly tilted beret and a light tan trench coat unbuttoned with its belt loosely tied in front against the chill of nighttime on the plains.

She tossed the beret and trench on the chair, and leaned against the wall, arms crossed.

"I'm not doing this for money, you know. If you try — I'll be insulted ... In case you're wondering."

I nodded; my vocal chords seemed to be paralyzed.

She walked up to me, threw her arms around my neck and brushed my lips with hers. That perfume! That touch! I nearly swooned.

Just then there was a double knock and a pause. Art stuck his head in the room and said Lucky had gone AWOL and he was going to look for him. He thought it would take a while. "Oh hi," he added, as if he'd only then noticed the girl clinging to me.

The lock clicked shut. Her kiss deepened, as our tongues tasted each other and electricity crackled through the air.

She shrugged out of the blouse, lips still touching mine. Kissed my nose and wriggled the skirt down over her hips. Daintily lifting one leg at a time, she shed the knee socks, leaving her dressed in a plain, dove-gray slip.

I slipped the spaghetti straps off her shoulders and slid the silky fabric down off her perfect, conical breasts as she lay back with a sigh. Her pink nipples were asking for attention and I flicked each in turn with my tongue, then nuzzled my face between them as I licked my way down her sternum toward her waist, gradually sliding the slip up her legs. Obligingly, she lifted her ass so the silk became a crumpled belt around her waist.

I kissed her belly button and flicked my tongue around it, rewarded with a girlish giggle and "Oooh, that tickles!" then inhaled deeply as my lips slid lower.

She lifted her hips and slipped her thong down her legs and kicked it away. Millimeter by millimeter I kissed my way through the dark, sparse hair covering her mound. Catching her tiny, erect clitoris with my lower lip, I kissed it deeply and massaged it with my tongue.

She moaned softly.

My tongue slipped between her labia and tasted her saltiness. As I licked around and around and up and down she arched her back, raising herself off the sheet and whispering "Yes ... please ... please ... please ... yes."

I pushed myself up slowly, gently, till my thighs were under her parted knees, and reached down and put my hand around my turgid cock. I looked down. My fist was clamped around the base. My erection protruded another fist-width to its broad, dark-red head. Veins stood out as I ever so gently guided the shiny head between her rosy lips, just below the pink clitoris standing out between her dark hairs.