Wheels of Fortune: The Ride of My Life - Cover

Wheels of Fortune: The Ride of My Life

by Shakes Peer2B

Copyright© 2004 by Shakes Peer2B

Erotica Sex Story: I cycle for exercise. Sometimes my rides turn into an adventure. This is the story of one of those rides!

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft   mt/Fa   Fa/ft   Reluctant   Light Bond   Anal Sex   Sex Toys   Bestiality   Caution   .

© Copyright 2004

This is the first in what I envision as being another episodic set of stories, rather than a series, much like the House in the Woods set. Each story will have different characters, different perspectives, but very little to interconnect them other than the setting and main character.

This was actually going to be my very first story published, then the idea for HIW-Bethany came along, and this got dropped and never picked up again, until now. It's changed considerably from my original idea, so I hope you like it.


I'm what's loosely classified as a cycling 'enthusiast' - someone who rides a bicycle more than 25 times a year. I don't belong to a club, and I'm not training for the Tour de France, but I do own a reasonably nice road bike (bought after riding my mountain bike off-road resulted in one too many injuries!).

I don't go to great lengths to find different routes to ride. For me, the riding is kind of a meditation. It helps clear my mind and keeps my body in reasonably fit condition. I abhor riding in groups or even with another person, simply because it takes too much concentration to keep from hitting them, keeping them aware of what I'm doing so they don't hit me, trying to carry on a conversation when I've barely got breath to keep my legs pumping, etc.

Mostly, I start from my house and take one of five or six different loops that eventually bring me back home after doing anywhere from 20 to 60 miles. I enjoy it, and hate when the weather or some personal obligation keeps me from a scheduled ride.

Occasionally, one of my rides turns into an adventure. This is the story of one such ride.

The little computer on my handlebars said I had gone a little over 17 miles, and I was pedaling easily on a relatively flat stretch of road, when I became aware of a 'thrub, thrub, thrub' sort of noise just behind my right leg. I started braking easily and looked back toward the source of the noise. I had just identified the black balloon protruding from my rear tire as inner tube, when it gave a sort of disappointing 'PLAK!' sound, and the rear tire went flat!

I really had no trouble getting the bike stopped, even though I expected a good deal of instability. I guess those really narrow tires have hidden benefits!

I unclipped my shoes from the pedals and stepped down.

When I got the wheel off and inspected it, to my disgust, the kevlar tread tire I had counted on to protect my tubes from going flat had simply opened up along about six inches of sidewall and let the tube out! I had a spare tube and the tools to change the tube but nothing that would boot a sidewall tear that long, and no spare tire!

Dreading a 17 mile walk in cycling shoes, I crossed the road and headed back in the direction I had come. I hadn't gone far when a pickup pulled up alongside.

The driver, a pleasant looking young woman in her thirties, leaned across the passenger seat and asked, "Need a lift?"

"You're a life-saver!" I said, lifting my bike into the bed and climbing into the cab.

"Nice shorts!" she said throatily, eyeing my lycra clad ass as I parked it on her seat.

A few years ago, you wouldn't have caught me dead in public in spandex or any other kind of form-fitting wear. Thanks to all that riding, though, I actually don't look half bad in it these days!

"Thanks!" I said, giving her an appreciative grin.

"Where do you need to go?"

I told her where I lived and she said, "Sure, I'll take you over there. Mind if I stop at the house and take care of something? Might take half an hour or so."

I shrugged. If I had completed my ride it would have taken longer than that, and she was doing me a favor.

"Suit yourself!" I said, unstrapping my helmet and running a hand through my sweaty hair.

She stuck out a hand and said "I'm Nancy! Nancy Simpson!"

"Oh, Ted Marks!" I shook her hand lightly, mindful that my grip often has other men wincing, but needn't have bothered, she had a good, strong grip, "Very pleased to meet you! I really wasn't looking forward to that long walk in these shoes!"

Nancy pulled the truck into a long driveway between immaculate white fences. The house must have been a quarter mile or more from the main road, and in the pastures on each side were a number of miniature horses. If you've never seen them, they're smaller than Shetland or Welsh ponies - perhaps a little larger than a Great Dane, though thicker of body. A couple of them were chasing each other around the pasture. Most of the rest were grazing contentedly at the lush grass.

"Yours?" I asked, poking a thumb at the scene outside the window.

Nancy nodded, saying, "Yeah. Mine and my partner's. She should be home. I'll introduce you."

'She?' Hmmmm. Well, it WAS California!

She parked the truck in front of the house and invited me in.

"Karen!" She called as we entered "Karen?"

Someone, presumably Karen, flew through the air and wrapped all four arms and legs around Nancy, engaging her in a passionate kiss, her pale, petite blonde frame in stark contrast to Nancy's rangy, dark haired, olive skinned body.

Nancy returned the kiss for a few seconds then peeled her partner off of her, saying, "Karen, may I introduce you to Ted Marks. Ted, my partner, Karen."

Karen gave me a predatory once over and cooed, "Ooooh and all wrapped up in spandex! How delicious!"

She extended a delicate hand and in a sultry voice said, "I'm VERY pleased to meet you!"

Karen was wearing a man's shirt that came to just below her ass, and apparently nothing else. I couldn't help but notice that it rode up to expose part of her hairless vee, as her hand came up to be shaken.

"Uh, very nice to meet you, as well, Karen." I said nervously, hoping Nancy wasn't getting too pissed about her partner coming on to me like that.

Nancy, though, laughed and said, "Come on, Karen, let him catch his breath before you jump his bones!"

Karen turned back to Nancy and in a hard voice said, "Aren't you forgetting something, slut!"

Suddenly, the world tilted and my perspective skewed as Nancy, on hands and knees, meekly crawled across the intervening space and buried her face between Karen's thighs. She kissed Karen's shaven mound fervently before looking worshipfully up at her partner and begging, "May I lick it, Mistress Karen, please?"

"Well," Karen said wickedly, "Since you've brought me such a lovely present, I suppose one taste won't hurt!"

The petite blonde, obviously in complete control of the larger woman, spread her legs and shuddered as Nancy's tongue swiped at her bare pussy.

"That's enough slut!" Karen commanded, "Get in the bedroom and get naked! I want you on your back and spread by the time I get there!"

Nancy crawled down a hallway, and when Karen turned back to me, she seemed a different person than the one who had just terrorized poor Nancy!

Slinking up to me, she gently caressed the outline of my growing erection through the stretch material of my cycling shorts.

"Ooooh! You're a big one!" she purred, "Tell me Ted, would you like to fuck my little slut?"

Well, opportunities like that don't come along all that often for a guy my age, and I wasn't about turn it down, not when opportunity was not only knocking, but bashing the door down!

I thought my head would fall off from nodding so hard!

"And," she cooed, biting my nipple through the material of my jersey, "would you like ME to fuck you, too?"

Duh! Would I like to have one of my favorite fantasies come true?!

"I'd like that very much!" I said, though it took a couple of tries to get my dry mouth to work.

"Well, then," she hooked an arm through mine and led me down the same hallway Nancy had taken, "Why don't we go see if the slut's ready for us!"

We entered a large bedroom to find Nancy absolutely naked, the rings in her nipples and clit glinting in the subdued lighting from the blinds, lying spread-eagle in the center of a king-sized bed.

She waited silently as Karen stripped me of my cycling togs, oohing and ahhing over the toned muscles underneath, especially my legs.

"I've promised Ted that he can fuck you slut!" Karen addressed the supine girl, "And I want you to fuck him back! Make sure he enjoys it, or I'll whip you within an inch of your life!"

"B-but Mistress!" Nancy cried, almost in tears, "He's a man!"

Karen sharply slapped the sensitive flesh of Nancy's inner thigh, saying, "He's the man I gave permission to fuck you, slut! And I'm ordering you to make it good for him! Is that clear!"

"Y-yes Mistress!" Nancy blubbered, "I just thought I was bringing him home for you!"

"That was sweet of you dear," Karen said, caressing the side of Nancy's face, "but you know how generous I am, and I want to share him with you!"

The wicked blonde came back to me, gently stroking my bobbing erection, "You've got a nice, big one there, boy. I want to hear her scream, ok? Balls deep on the first stroke, or so help me I'll cut 'em off for you!"

It wasn't 'til I was aiming my rampant shaft at the pink opening that I realized Karen had coated it with some kind of lubricant.

Generally, I'm a gentle lover. I know how big I am and I try to take my time and let my partners get accustomed to my size. About half of them never take the whole thing!

This situation, though, and Karen's threats, overcame my personal preferences, and, praying that it wouldn't hurt her too badly, I drove full depth in one massive thrust! To my relief, Nancy must have been accustomed to large penetrations, because she accepted me much more easily than I expected, though nobody takes something that size, that quickly, without SOME pain!

"Good boy!" Karen said, when Nancy's scream had died to a whimper, "Now, slut, wrap your arms and legs around him and show him how much you're enjoying your first heterosexual fuck!"

Reluctantly, Nancy complied, as I flexed my pole inside her, trying to make room for what was to come!

"Well, what are you waiting for, boy!" Karen cooed, caressing my butt, then smacking it, HARD, "Fuck the shit out of her!"

I did as ordered. I pulled all the way out to my glans, then slammed back in! Each thrust brought a cry from Nancy's throat, though after a while, the nature of those cries changed from pain to lust!

The nature of Karen's caresses on my butt changed, too! I felt a greasy finger slide deep into my ass and almost came right there! Thankfully, or not, even with the split saddle, I still lose a measure of sensation in my nether regions after sitting on the bike for a while. It was just enough to keep me from finishing right then! I hated to think what Karen's reaction might have been had I lost it so soon!

Not having been given any other instructions, I continued to fuck Nancy, whose arms and legs tightened around me, urging me deeper. All too soon, the finger departed, leaving me feeling strangely empty.

I felt the bed sag as Karen climbed up behind me, and something hard and slippery nestled into the greasy depression of my anal ring.

Karen leaned over my back, digging her rigid nipples into my shoulder blades and whispered sexily, "Ok, boy, here's your dream come true! I'm going to fuck you while you fuck Nancy!"

Just about that time I finally figured out that what was poking at my asshole must have been Karen's strap-on and I started struggling to get away! No dice! Nancy's arms and legs tightened around me even more, and she covered my mouth with hers, absorbing my scream in a passionate kiss as Karen entered me the same way she made me enter Nancy!

I hadn't been in the saddle THAT long! God Damn! That HURT! My poor, abused hole couldn't decide whether to clamp down or open up! Every time it closed against the invader, searing pain shot up my nerves, screaming 'DON'T DO THAT!' to my brain, but my brain just knew this thing wasn't good to allow into my body, so it kept sending back 'DANGER WILL ROBINSON! INTRUDER ALERT! DEFENSIVE POSITIONS!'. The result was that my poor confused ass sort of vibrated around the plastic, shooting pulses of gradually diminishing pain throughout my body!

By the time the pain subsided enough for me to become aware of some of my surroundings again, Karen was snuggled tightly up against my back.

I shook my head, saying "Well, shit! If you'd just TOLD me what you had in mind, I'd have gone along willingly... !"

 
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