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Anal On The Road

Category: Anal Sex
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I watched her out of the corner of my eye as her homely face wrinkled and crinkled at the printout in her hand. She looked back and forth from her itinerary, to her wrist watch, and back again. She was clearly not pleased.

“Problems?” I asked from seat 22A.

“I think I’m going to miss my connection!” she said from seat 22B.

I could sympathize. Air travel, with which I am more than slightly familiar these days, has been particularly harrowing of late, and I’ve missed more than my fair share of connections myself. I tried to commiserate with her. “We took off over an hour late. I’ll probably miss my own connection, you know. On the plus side, Charlotte is a fairly nice airport to be stuck in, even if you are there for the night. Comfortable chairs to sleep in, and free wireless.”

“For the night!” she shrieked, not at all mollified. “Do you really think it will come to that?”

“You never know. I always like to plan for the worst,” I told her. I looked her up and down. She really did have quite a homely face, with lumpy lips, a receding chin, and a slightly mottled complexion. But other than that, she was a nicely shaped woman. Her breasts were well proportioned, and strained her rib-knit sweater most pleasantly. Her legs were long and lean, and ended in some nice tall black boots. But if I were to fuck her, I thought lewdly, it would have to be doggie-style. “Best not to get yourself worked up unnecessarily. What will be will be, you know.”

We chatted of trivialities for the rest of the flight. I’ve learned to be nice to all women, even ugly ones. For one thing, they often have good-looking friends. And for another thing, on lonely business trips, they are better than nothing at all. Her name was Heather, and she was connecting in Charlotte for a flight to Atlanta. She did have a nice, deep, sexy voice. I figured that in the dark, fucking her pussy and listening to her deep voice moaning, she’d probably be alright. She was attending a research conference. I was connecting to Richmond for a sales call. Given the lateness of our departure, it was unlikely that either of us would be checking into our intended hotels tonight, but more likely sleeping in the terminal at Charlotte, or in an airport motel if we got lucky.

We finally landed, and Heather and I raced for the terminal to check the flight monitors. As we jogged up the jetway in single file, I couldn’t help but notice the erotic wiggle of her well-formed ass. Her cheeks pounded out a perfect figure-eight in time with her long, booted strides. Homely face or not, she sure had a nice pooper! Naturally, both of our connecting flights were long gone. We walked together to the customer service kiosk to see what we could salvage of the situation. Since it was already after 11 pm, there were no more flights out for the night. We both got booked on early morning flights to our destinations, but neither of us was particularly pleased with the situation. They gave us each hotel vouchers, though. At least we wouldn’t have to sleep on airport benches.

“Do you know of any good restaurants around here?” Heather asked me.

“Not really. But we should probably go to the hotel and get a room before they are all taken. We can always call for room service.”

We grabbed a cab to the nearest hotel, in order to be close by for our early morning flights. We arrived to find a long line of stranded passengers at the front desk, all wanting rooms. By the time we got to the front of the line, the desk clerk shook his head sadly.

“We only have one room left,” he said. “But it is a junior suite, with a king size bed and a fold-out couch.”

“I’ll take the couch,” I told Heather. “You can trust me. I’m a perfect gentleman.”

“A perfect gentleman?” she chided. “That doesn’t sound like much fun.”

I wasn’t sure what she meant by that; just a flippant remark by a weary road warrior? Or a flirtatious come-on? If she’d been a beautiful babe, I’d have been more likely to hope it was a come-on. Given the circumstances, I suspended judgment. Either way, we took the room and checked in.

Too tired to search for a restaurant, we ordered room service. I ordered a sirloin burger, extra rare, and fries. She ordered a salad, chicken wings, and a baked potato. We also helped ourselves generously to the mini-bar, red wine for her and vodka for me. Within an hour we were feeling much better. In fact, we were old pals, laughing and joking about life on the road and the incompetence of the airline industry. She was a good conversationalist, and I found myself liking her. I was almost glad that she was so homely. Sometimes it’s nice to have a woman friend who is just a friend!

Finally ready to turn in, I opened up the fold-out couch. Since our checked luggage was still entombed somewhere within the bowels of the airport, we had nothing to sleep in but our underwear. I stripped down to my boxers, and she to her bra and panties. I curled up on the fold-out, and wished Heather a good-night.

Instead of saying goodnight back, she stated bluntly, “I saw you staring at my ass in the airport, you know.”

“You could see that? You must have eyes in the back of your head,” I said. Women. They can always surprise you!

“Maybe,” she said. “So have you always been an ass man?”

“No, not really. But yours… it really moves nicely when you walk. I’ve never seen an ass wiggle quite like that,” I told her, in all honesty. It did have some very nice moves. I remembered that gyrating figure-eight and my cock stirred slightly in my boxers.

“I am rather proud of it. In fact, I think it is my best feature. It’s also my most talented feature.”

“Oh??” I wasn’t sure what she meant by that. But I had a hunch I was about to find out.

“Have you ever fucked a woman in the ass?” she asked. She’d had just enough wine to ask such a blunt question, and I’d had just enough vodka to answer it.

“Well, once or twice, when they requested it,” I told her. Personally, I’ve never really seen the point in fucking a chick in the ass, not when there is a perfectly serviceable pussy just an inch away. Still, when the subject of discussion turns to sex, I’m always willing to listen. “What did you have in mind?”

“Well…,” she looked me in the eye. “Personally, anal sex is my all-time favorite. I think I have more nerve endings in my anus than I have in my pussy, and I’ve devoted myself to developing my butt-fucking skills. And the way you were admiring my ass, well, I figured maybe you would be interested.”

I looked her up and down. She wasn’t kidding. Sitting on the bed in her skivvies, her homely face showed me a resolutely earnest expression, and I sensed both a profound trust in me, and a deep, unfilled need. This chick wanted some action, and wasn’t going to be denied. She certainly wasn’t going to be denied by me, anyway.

“I’m game,” I told her. I’ve never been one to turn down meaningless anonymous sex, especially when on the road and missing my sweet sexy girlfriend back home. The business travel life is lonely enough without being picky about who you bed down with. “Talk to me.”

“Well, first of all, forget about that silly fold-out couch and come join me on the bed.”

I made short work of hopping to the bed, shedding my boxers on the way. She unhooked her bra as I watched, and tossed it onto a nearby chair. Then she stood up, turned to face away from me, and theatrically slid her panties down to her ankles, her glorious ass flashing its vertical smile towards me. Moments later we were rolling naked on the bed, arms and legs wrapped around each other, tongues jousting in each others’ mouths, and pressing our bodies close. Her body was nice and warm and soft, and nestled and rubbed against my own in all the right places. Her soft flesh felt marvelous against my own as we kissed deeply. But I kept my eyes closed so I wouldn’t have to see her homely face. It wasn’t long before my cock responded to the stimulation, and was sticking out like a diving board.

She gently stroked my throbbing cock as we rolled in each others’ embrace. “This is nice,” she said, her soft fingers sliding up and down my shaft. “Are you ready for some serious action? I really want you to slide this cock into my asshole. I’d like that a lot.”

“Your whim is my command, darling,” I told her. And I meant it. Although I’ve never been a butt-fucking kind of guy, her tender nature and her wonderful kisses made me want to please her. Besides, a hole is a hole, and my cock had worked up a load that needed to be released somewhere soon.

She rummaged around in her carry-on bag and pulled out a bottle of Astro-Glide. She held it up to the light, and we both watched the viscous liquid settling in the bottle.

“You travel with Astro-Glide?” I asked her. “Now that IS being prepared!”

“I prefer to call it ‘Asshole Glide’,” she laughed, and squeezed a long bead onto the top of my cock. Her soft hands began slathering it all over my shaft, up and down, then around the head, and getting me completely lubed up. She added a second long bead and continued her ministrations. It felt marvelous. I forced myself to watch her face instead of her sexy hands on my tool so that I wouldn’t cum right then and there. Finally she let go and handed me the bottle. “Get my butthole good and slick with it, will you? Then you can start me off with a finger or two.”

She squirmed up onto the bed, her shapely body executing all sorts of lovely motions as she assumed an all-fours position, her lovely caboose in the air and spread open for my inspection. I admired the round shapeliness of her buttocks, the firmness of her cheeks, and the milky whiteness of her soft skin. I knelt behind her and drizzled a long thin train of the lube into her crack. I watched as it dripped slowly from her tailbone down toward her brown pucker, reflecting the light of the ceiling lamp and focusing my attention on her nether orifice.

As I watched the sticky liquid surrounding her butt-eye, I tentatively reached out one finger, and traced it up and down her anal crease. I felt her body shudder slightly each time my fingertip crossed her brown puckered anus. I caressed her pretty little starfish over and over, and enjoyed the feeling of power as it made her shudder with pleasure with each stroke. She really was sensitive there. After several back and forth trips, I finally, gently, slid my fingertip inside her golden depths. I pressed shallowly and gently at first, of course, but then gradually deeper and more forcefully. She let out a series of low moans, deeper and stronger as I penetrated her dark rosebud more and more intensely. Finally, I plunged my finger in straight, first to one knuckle, then two. Her moans became more guttural and more intense. I shoved my finger in to the third knuckle, and began a beckoning motion with my fingertip. Her body began to shudder, and her moans intensified further still. Finally, I pressed my finger in to the hilt, and added a rotational motion to the beckoning gesture. She whipped her head back and forth, and her moans intensified to the level of a low scream.

“Two fingers!” she shouted, and pushed her buttocks back against my hand. I added a second finger, and beckoned and rotated for all I was worth. Her thrashing intensified still further. I sawed and twisted and beckoned, and marveled at how her body responded to the stimulation. She bucked and moaned and shuddered, but eventually she needed more. “Enough fingers!” she shouted at me over her shoulder. “Fuck me, damn it! Fuck me with your fucking cock!”

That was enough for me. I climbed onto the bed and knee-walked up to her shapely derriere. Her anus was twitching and oozing, fairly begging for my tool. My throbbing cock was jutting out like a number nine re-bar, and I grasped it in my hand and pressed it up between her cheeks, my flaring head directly against her raw, needful bunghole. As I slowly pushed it against that brown bull’s-eye, I drizzled more lube from the bottle into the heart of the action. I pressed, gently at first, then harder, until the rim of my cock-head cleared her sphincter and I heard myself enter her nether regions with a distinct “pop!” She emitted a shriek, but if it was of pain or pleasure, I could not tell.

Once the head of my cock was inside her, the going became much easier. I was surprised at the ease of action, as my cock slid back and forth as easily as a piston in a cylinder in a high-performance sports car engine, her bowels holding it in a snug, slippery embrace. I began pumping her ass with wild abandon, just like I would a wonton and well-lubed pussy. However, her ass pumped back with much more talent than I’ve ever experienced from any vagina. For one thing, she was able to clench her butthole tight around my shaft, much like a fist might choke up on a baseball bat. She would clench me tightly on my in-stroke, then loosen up on my out-stroke, and then tighten again on my next in-stroke. The effect was like that of a never-ending penetration, like I was fucking an infinitely-deep pussy. Several minutes of that, and my cock was stimulated in ways it had never before felt. The clenching also helped contain the pressure of my blood in the shaft, and I felt bigger and harder than I had ever felt before.

But that wasn’t the end of her talents. Next, her butt cheeks themselves began to get into the act; while her butthole was squeezing on the middle of my shaft, the muscles of her cheeks began closing and clenching on the base. It felt like two large, soft pillows, gently cradling and loving my cock shaft. Between the bite of her anus and the nibbling of her cheeks, my cock had never before felt so coddled and loved. I began swinging from my hips, probing the depths of her colon, and feeling the beginnings of a powerful orgasm start to well up deep in my loins. On each thrust, I also felt the firm softness and warmth of her butt cheeks on my thighs, adding yet another dimension to the stimulations. I could easily have reached an awesome climax this way, but she wasn’t done surprising me yet. She began swiveling from the hips, moving in a circular, gyrating motion, a figure-eight combined with an up-and-down and a back-and-forth, all in time with the anus-clenching and buttocks-nibbling. I fought to maintain control, as I wanted to enjoy this marvelous symphony of sensations for as long as possible.

The last straw was when she reached her hand down between her own legs and began stroking my dangling nutsack. Her fingertips, wet with the juice from her own pussy, twirled and caressed over the sensitive folds of my scrotum. I found out later that at the same time, she had her thumb on her clit, which of course only made her bucking, twisting pelvic motions all the more intense. All of these sensations were more than I could stand: her clenching, almost prehensile anus, her firm, warm butt cheeks, her gyrating hips, and her delicately stroking fingers. Oh my!

As I felt my orgasm reaching the level of inevitability, I realized that all this stimulation was not strictly for my benefit; that for each action that stimulated my tortured cock, there was an equal and opposite reaction acting on her sensitive, highly trained anus. She screamed as an orgasmic shudder wracked her entire body, and her shuddering, twitching motions were just enough to send me over the edge. We came together, our bodies vibrating and spasming as one, my cock pumping spurt after spurt of cum deep into her colon. She collapsed onto her belly in a swoon, and I flopped onto her back, completely spent.

We lay there for awhile like a short stack of pancakes, both gasping and breathing and drinking in the afterglow of our orgasms. The blood was pounding in my ears, and my cock was only slowly softening in her glorious ass. My mind was reeling; I felt that I needed to take some time and reevaluate my entire opinion about anal sex. Maybe a perfectly good pussy an inch away ISN’T a reason not to fuck a beautiful, tight, sucking and clenching asshole? Who knew?

Finally, putting these thoughts out of my head for now, to be considered at a later date, possibly over a martini at some hotel bar on a more lonely road trip, I rolled off of her, extracting my shriveling tool from her brown love tunnel. She flipped over onto her back, and raised herself up on her elbows, flipping her hair out of her eyes and breathing deeply. “Well,” she said, “that was a really great butt-fucking! Are you sure you are new at this?” I assured her that I was. She looked me piercingly in the eyes, so much so that I almost became nervous, and asked her what she was thinking about.

“Oh, not much,” she said. “Just come here and hold me awhile.” We curled up in a spooning position, my arms around her waist, my quiescent cock just millimeters away from the orifice that had brought it so much joy only moments before.

My eyes fluttered open, and I realized that I’d been dozing. I was lying on my back, and she was looking down at me, still with that piecing look in her eyes. She was also slowly stroking my cock, which had sprung back to life. “Well?” she asked me, mysteriously.

“Well, what?”

“Well, are you ready for the flip-side? So far you’ve only experienced half of the pleasures of anal sex.”

“Huh?” I said, not knowing what she meant by that. Or, more truthfully, not wanting to know what she meant. But I did know, in my heart.

“You know what I’m talking about,” she said conspiratorially. She winked at me, her homely face taking on a wise and knowing mien. “You didn’t think you’d enjoy poking me in the butt, but you did. Maybe you’d like receiving it too, more than you’d expect.”

Automatically, my face registered shock at her suggestion. But, I have to admit, my revulsion was nowhere near as complete as I would have expected it to be. Truth be told, I’ve had my share of digital prostate exams, and I’m not talking about computer-aided, here! And secretly, when the doctor plunges his finger deep into my asshole, and probes around my prostate, I’ve always kind of enjoyed the full, warm feelings that I experienced in my deepest, darkest areas. Although I always maintained, even to myself, that it was something I merely endured, there was no denying, in my heart of hearts, that there was a certain amount of pleasure involved, and even a certain amount of curiosity about how much more pleasure there was yet to be realized. And here I was, in a hotel room in Charlotte, North Carolina, with a woman whose last name I didn’t even know. What better or more anonymous venue for exploring these secret and forbidden passions?

“Oh… Kay,” I heard myself saying, against my better judgment. “How exactly do we do this?” My cock was twitching again, and my sexual instincts and curiosity were overruling years of conditioning.

Her homely face smiled, and her eyes twinkled. Suddenly she wasn’t nearly as homely as she had been before, but almost beautiful in the joy that showed on her face. She reached again into her carry-on bag, and pulled out a large, purple, jelly dildo. My eyes turned into saucers!

“I call this one the Widow-Maker,” she said. It was as long as a Louisville Slugger and as thick as a bottle of Grey Goose, and made of a wiggly purple translucent substance. It scared the shit out of me! “I’ve had lots of fun with it.”

“You can’t be serious!” I cried. “That would split me in two!”

“Oh, I wouldn’t use this one on a virgin like you,” she said. “I just wanted you to know what you might work up to some day. I have a much smaller one, too.” She reached back into the bag and pulled out a shorter, thinner dildo, but still of the same wiggly, translucent purple rubbery material. Although the shaft looked much more benign that the Widow-Maker, it still sported a large, flared, mushroom-shaped head that looked like it could cause problems for a virgin asshole such as my own. The shaft was highly textured, with many ridges and rivulets along its length. I could only imagine what they would feel like on the sensitive nerve-endings of my butthole. At the opposite end of the shaft there was a small, hook-shaped projection, like a crooked finger. “I call this one Little Jimmy,” she said.

As I was staring at Little Jimmy, and wondering if I dared take him up my poop-chute, she was once again rummaging in her bag. Eventually she pulled out a black leather thong, which she began strapping around her waist and crotch. The thong had an opening in the front, which Little Jimmy fit into perfectly. As she was plugging Little Jimmy into the opening, I saw how the small hook-shaped projection fit perfectly against her clitoris. Apparently she was going to enjoy the experience at least as much as I was. Probably a lot more, I thought uneasily.

“Okay, it’s go time,” she said. She handed me the bottle of “Asshole Glide.” “You might as well lube him up good,” she said. “You are going to wish you had, if you don’t.” I poured the lube over the wobbly purple cock that was jutting proudly from her crotch, and rubbed it in well, jacking the artificial cock as if my life depended on it. For all I knew, it did.

She grabbed me by the hips and manhandled me into a new position, standing on the floor, facing the bed. She bent me over at the waist, with my elbows and forehead on the bed, and my butthole winking at the ceiling. I expected her to stand behind me and pierce me with the purple pud, but instead she knelt on the floor and began to stroke my butt-cheeks with her gentle fingers.

“Such nice cheeks,” she crooned, stroking and rubbing. “Let’s get them ready for some fun, first of all.” Her fingers stroked up and down the backs of my thighs, the fronts of my thighs, and all over my cheeks. They stroked in gentle circles, in long linear traces, and in little dancing tickles. She even reached between my legs and stroked my shaft and massaged my balls. Then she began stroking my butt crack, up and down, probing and massaging, getting my glutes well relaxed. Finally, her gentle fingers flicked across my bunghole, gently at first, and then more firmly. She drizzled some of the lube on me, and worked it in with her fingers. First one finger, then two, invaded my virgin asshole, but only to a knuckle or two. Then, to my surprise, she removed her fingers, and began to probe my puckered rosebud with her tongue! She worked her talented tongue all over and around my hole, massaging it and relaxing it, and opening it up for future fun. She spread my cheeks with her hands and pressed her mouth and face deep into my crack. Eventually, my hole was completely moistened with copious amounts of both saliva and lube, Only then did she get to her feet, and press the flaring tip of the purple dildo against my virgin bunghole.

She placed her hands on my hips, and gently pried my butt cheeks apart like she was splitting a dinner roll. “This might hurt a bit at first,” she said, “but once the head enters you, I promise it will be nothing but pleasure.” I gritted my teeth and silently asked myself how I got into this predicament, and wondered if I could survive a leap naked out of the window and down to the parking lot. I felt the cone-shaped mushroom of the purple cock-head press against my shit-hole. At first it felt interesting, and then slightly pleasurable as the beginning of it began to stretch my sphincter. Then, as it penetrated slightly deeper, the pleasure turned to a stretching feeling, and then a pulling feeling, and finally to an intense burning sensation. My brown-eyed orifice was stretched beyond the limits of pleasure, or so I thought, and still the conical cock-head continued to invade me. The burning sensation turned to a tearing sensation, and then a searing, screaming, excruciatingly painful sensation, as the full radius of the mushroom forced itself into my complaining, screaming asshole. Tears welled up in my eyes and sparks obscured my vision. Then, finally, mercifully, it was in! My brown anus ring collapsed around the wrinkled, textured shaft, and held it tight, the conical head deep inside my Hershey highway. I panted in relief, savoring the receding of the pain.

She held still, knowing that I had crossed a threshold. As my breathing slowly returned to normal, she gently stroked my buttocks with her hands and fingertips, and whispered encouraging words into my ears. “You’re doing great, honey. The worst is over. The head is in. It’s all good from here on out, I promise you.”

When I was back to normal and ready for more, she sensed it and began to stroke. She was very gentle, and moved back and forth by only fractions of an inch, at first. Then she gradually built up momentum. The ridges on the shaft began to do their job, stimulating the sensitive nerve endings of my virginal butthole. Stroke after stroke, more and more jolts of electricity spread from my chocolate chakra and stimulated the pleasure receptors of my body. I never knew my sphincter was so sensitive, or that it could feel so much pleasure.

The sphincter sensations alone would probably have given me a mind-blowing orgasm in time, if that was all that she let me receive. But it wasn’t long before a new sensation assaulted me: she gradually increased her stroke length until the flaring mushroom-shaped head of the dildo was bumping into my prostate glad, deep within the bowels of my abdomen.

The prostate is a very sensitive part of the male anatomy, rarely stimulated during heterosexual experiences. But when the soft, rubbery head of Little Jimmy pressed against my gland, it released the kind of pleasure that I had never before known. While the stretching and shredding of the textured shaft on my sphincter gave me shuddering, exciting waves of pleasure, the prostate stimulation provided a deep, slow, growling wave of warm ecstasy that started in my gonads, and flowed up my torso like a wave of heat, gradually reaching my lungs, my heart, my neck and my face. The combination of the butthole stimulation and the prostate massage was almost more than I could take.

But that wasn’t all. She was the consummate pro, and soon added the third leg of the triple whammy: she reached her slim soft hand around my hip and gripped the shaft of my cock with it. Her soft palm wrapped around my shaft and began jacking me back and forth, all in time with the thrusting of the purple dildo in my tortured asshole. Her hand went back and forth, up and down, periodically sliding over the ultra-sensitive skin of my still-lubed cock-head, and sliding around my nut-sack like she was polishing a bowling ball.

This was just too much. The combination of her butthole stroking, her prostate massaging, her cock-shaft sliding, and her scrotum tickling had me completely on edge and flipping like a fish on a line. My pelvis spasmed. My jaws clenched. My knees knocked. My eyes rolled back in their sockets. The blood pounded in my ears and my eyes watered like I had swallowed a pound of wasabi. I felt a small thermonuclear device reach critical mass deep inside my colon, and then explode with the rush of a thousand detonating hand grenades. The rippling shock wave traveled from my sphincter to my scrotum, and turned my body inside-out. My entire being became one quivering mass of uncontrollable pleasure. I thought I would explode, and I did. I heard a scream, and realized it was my own, as I spewed wave after wave of cum onto the bed. I collapsed in exhaustion onto the mattress, and she kindly followed me down, the quivering purple dildo safely and securely tucked into my formerly-virginal asshole. I must have passed out. We slept.

The hotel wake-up call jolted us out of a sound sleep. We were on the bed in a spooning position, but she was the “big spoon” and still had Little Jimmy strapped to her hips. My asshole felt like I had just shit a set of steak knives, but still, I didn’t regret the experience. We both looked at the clock, thinking the same thing.

“Well?” she asked. “Do we have time for one more round?”

My flight was a half hour earlier than hers. I did some quick mental arithmetic. If I skip taking a shower, shave in the cab, and sprint through the terminal to my gate, I could probably afford a quick one. “You’re on,” I said. “But this time, I’ll take the top.”

She smiled at me, and I noticed that somehow her face wasn’t homely in the least anymore. She tossed me the bottle of lube and said, “Giddyap!”

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