Anal On The Road

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!"