Memorable for the Wrong Reasons

I also covered a large territory and was out of town overnight quite a bit. After we broke up, or should I say she dumped me, she started dating my buddy Tim almost right away. He worked in engineering so he made good money, possibly better than me, and it was a steady paycheck.

Knowing Cheryl's shopping habits, always wanting to go to nice restaurants and so on, I could see that she was nothing but a gold digging bitch, and left me for someone with a bigger wallet. While that made sense, they had gotten together so quickly, and I had been out of town a lot. Maybe she'd been having an affair. I wouldn't think that Tim would do that to a friend, but she was pretty hot and I'd never known him to turn down a piece of ass.

I had to pull off to the side of the road because I was so upset. There was a sign for a trail that simply read, Quiet Walkway. I got out of my car and started to walk the path back into the woods to clear my head.

All I could think about was that a friend of mine might have been fucking my girlfriend when I'd been out of town. Fucking her with a cock that was about twice as long as mine. Damn! Even if penis size wasn't really important to her, after experiencing something that huge she probably barely felt me inside her.

The trail was just a loop less than a mile long, and by the time I was back at my car I realized there was no proof Cheryl had an affair with Tim when we were together. I was better off not having that high maintenance bitch in my life. Furthermore, I was glad I had cum on her new cowgirl boots. Sure, I had cleaned up the mess so she would never know, but there was satisfaction knowing how pissed she'd be if she found out.

After my car had struggled back up Ski Mountain Road to the chalet, I saw the parking area was empty. They had gone to dinner, just as Tim said they would. I was hungry as well.

There was plenty of food in the fridge, some of which had been abandoned by Scotty, Renee, and John, when they departed early. I put a potato in the microwave, corn on the cob in a pot on the stove, and a steak on the gas grill that was on the deck outside the living room. I'd also picked up a twelve pack of beer on my way back and had put a few of those away by the time I was done eating.

Thinking it was best to move my things into the room downstairs before Cheryl and Tim got back, I went upstairs. My duffel bag, which I had packed earlier this morning, was sitting on the floor outside the door to what had been my room. That door was closed, and when I checked I found they had clicked the privacy lock, and exited through the connecting bathroom.

My electric razor and toothbrush, which I had left in the bathroom, were sitting on top of the duffel bag. The message was clear, I was out. I was about to head back down the stairs, but I had to take one last look in my former bedroom, simply because I was thorough and always made one final sweep before leaving a hotel, or in this case a chalet.

The small room with the bunk beds felt like a lonely place. Probably used by kids most of the time. No one that slept in here got laid. Sex was for the adults in the next room.

I hadn't forgotten anything in that room but in the bathroom I noticed that a bottle of my shampoo was still on the edge of the tub. Best to abandon that. If I packed it up and Cheryl and Tim somehow missed it tomorrow morning, they would know I had passed through their room and likely get mad.

On my way out of the adjoining bedroom, I noticed that they also had their bags packed. The stack of Cheryl's shopping conquests had been somewhat reorganized, and there was even a pile of pamphlets for local attractions to one side, which who knows, she might put in a scrapbook.

The thought came to my mind that it would be nice to smell some of her dirty panties. Earlier in the week her dirty clothes had been scattered all over the floor on her side of the bed. Everything was packed now though, and I wasn't about to go pawing through her suitcase.

There was however a pair of her shoes, just under the bed on her side. A pair of black leather flats. I'm more a fan of high heels, but those flats were cut low on the sides and showed off her sexy feet pretty well, including a hint of toe cleavage. About as sexy as a pair of flats can get. Cheryl had worn those just about every day of the week. I knew they would smell strongly of her sweaty bare feet, and I was right.

Kneeling beside the big four poster bed, I clutched one of Cheryl's flats in my hands. The black leather was soft and had many scuff marks. Holding it up to my nose and breathing in deeply, the smell of old leather soaked with the sweat from her sexy foot was almost overpowering.

I gave the insole a long, slow lick, and tasted the salt from Cheryl's dried sweat. I licked the inside of her shoe repeatedly, only pausing occasionally to savor the aroma some more, until the flavor of her sweat was gone.

Picking the other shoe off the floor, I intended to give it the same treatment, but first I unzipped my jeans and released my cock, which was rock solid erect. Deeply inhaling and tasting the second shoe, I slipped the first one over the tip of my penis, jamming the tip into the toe box and rubbing it in the confines of the soft leather.

Sweating and shuddering with arousal, before long I erupted. I groaned loudly as I felt myself spewing one hot burst of cum after another into her shoe. Breathing heavily, I set one shoe down so I could steady myself against the edge of the bed.

Slowly I withdrew my now softening penis from Cheryl's flat. The tip was glistening with cum, and a long thin drip clung to the insole as I pulled out. I had masturbated with women's shoes before, but this time had been the most intense experience ever.

The thought crossed my mind to leave my cum in the toe of her shoe, and take off before she got out of bed in the morning. Who knows what shoes Cheryl was wearing tonight, but it was unlikely that she would change into these when she got back from her dinner with Tim.

I could imagine her reaction, slipping her bare foot into her shoe, her toes oozing into a puddle of cold and drying cum. In a sense I would get the last laugh, but I wouldn't be there to enjoy the moment so I cleaned up my mess instead. There was plenty of time and after giving her flats one last inspection and setting them exactly where I remembered them, I went down to the kitchen to grab a fresh beer from the fridge.

Later I was soaking in the hot tub on the patio outside the lower level. I hadn't packed a swimsuit so I'd just got in naked. Darkness was falling and the view of the forest under the stars was amazing, despite the lights of the town below.

Although I wasn't into all the tourist crap down in Gatlinburg and Pigeon Forge, I could see it being a nice place to bring a girlfriend. We wouldn't come with a big group of people though. Just the two of us in one of the smaller rental chalets. Some chick that liked to hike in the National Park by day, then go into town for a romantic dinner at night.

There was a chaise lounge near the hot tub. The back rest was reclined nearly flat. On a romantic vacation I could imagine just spending a day at the chalet, with my lady sunbathing on a lounge like that one.

I envisioned a young woman with large breasts and curvy hips. Long flowing brunette hair. Wearing a string bikini made with a gold lame' fabric that gleamed in the sun. She would also be wearing some strappy wooden sandals with high heels, just because she knew they turned me on. I would rub the suntan lotion on her body, slowly, and seductively.

With the surrounding trees and our chalet being on the steep mountainside, there would be total privacy. I would get on my knees beside her, clench the bikini string above one of her hips between my teeth, and slowly pull to release the knot.

Then I would peel back the shiny gold triangle of her bikini bottoms to reveal her dark patch of neatly trimmed pubic hair. I may have even trimmed that for her earlier on our vacation. She would willingly spread her legs, hooking one spike heeled foot around my shoulders.

When I went down on her, she would already be moist and fragrant with arousal, and I would gently lick her until she came, her sweaty oiled body shuddering with pleasure in the sunlight.

As I fantasized, I adjusted my position so that one of the hot tub's jets swirled the warm water around my crotch, as I lightly stroked my erection with my fingertips.

I envisioned another scene with the same girl, on the same private patio, on a warm rainy afternoon. I would be lying naked on the chaise lounge, the foam padding wet and cool on my skin.

My woman would be wearing a shiny black vinyl rain jacket, and nothing else but a pair of glossy black rain boots. The front of her jacket would be unsnapped to expose her wonderful breasts. She would be straddling me, aggressively riding my hard cock.

The rain would be pelting on our bodies and making a popping sound on her vinyl jacket. My hands would encircle her waist, wet with rain, and reach down to squeeze her sexy ass as she brought me nearer to orgasm.

I suddenly stood up and moved to the side of the hot tub. A burst of cum arced into the darkened shrubbery beside the patio, followed by a second shot. I leaned over the side of the hot tub and slowly milked the rest of my cum out of my softening erection, breathing heavily and completely satisfied.

It was some hours later when Cheryl and Tim got back to the chalet. I had been watching the satellite TV system and had dozed off. She was wearing a nice blue mini dress that showed off her body. It would have looked killer with a pair of stiletto heels, but she wore these unflattering sandals with low blocky heels. It was no surprise that she was carrying a few shopping bags.

"Stop drooling, pervert," was all she said as they both headed straight upstairs.

My first thought was to go to bed. Having drank a few beers this evening, not to mention having masturbated several times as well, sleep should come easily. However, I felt well rested at the moment, so I decided to stay up a while longer.

I'd thought that Cheryl and Tim would have turned in soon, but I heard them upstairs talking, with her bursting into occasional fits of laughter. I was taken by surprise when I heard their bedroom door open and Cheryl call down to me.

"Hey, Chris. You freaking pervert! You want to come up and watch us?"

I turned around and looked up at the loft. She was wearing some white lingerie, leaning over the railing to show off her modest cleavage. One foot was thrust partially out through the spindles of the railing. She was wearing the silver cowgirl boots, and rocking that one foot slowly and seductively.

"Come on," I said. "I know you're bullshitting me."

"No, man. It's true," I heard Tim call from the open bedroom door.

"We'll let you watch," she said. "But only on my terms."

Of course, there had to be a catch. I was pretty sure they were joking, but she looked so fucking hot. I couldn't help but ask what the terms were.

"First, you need to strip buck-ass naked. I'll explain the rest once you get up here. You've got one minute before I'm locking the door and you lose your chance," she called over her shoulder as she walked back into their bedroom.

Now I may be a pervert, but I'm not that gullible. I knew they were setting me up for something. Maybe just slam the door in my face and laugh, just as I got to the top of the stairs.

It also occurred to me that maybe somehow she found out I had masturbated with her shoes and those new boots she was wearing. I could get up to their room naked, where Tim was lying in wait to kick my ass.

Time was running out and my curiosity got the better of me. I'm sure I looked like a fool, quickly pulling off my clothes and running naked up the stairs. I stopped in the open doorway to their bedroom.

Tim was lying back on the bed, wearing only his boxer shorts. Cheryl was standing near the foot of the bed, one hand on her hip, the other brandishing one of her black leather flats.

"You're a naughty boy!" she said. A wave of panic washed over my body. She had somehow figured out that I had cum in her shoe. "Naughty boys get spanked," she continued. "If you want to watch, I'm going to give you a spanking first." She slapped the smooth leather sole of her shoe in palm of her other hand for emphasis.

She was wearing a bustier made of gleaming white satin, trimmed with soft white lace. It had garter straps that hung loosely from her waist as she wasn't wearing stockings. The matching panties were probably a thong. It was an odd look combined with the silver cowgirl boots, but she was hot enough to pull it off.

"When you watch us, you won't be allowed to play with yourself," she further explained the terms. "You're going to be cuffed to that chair."

With her shoe, she pointed at a wooden chair near the corner of the room where her shopping bags and stuff were stacked. A pair of handcuffs was lying on the seat. Cheap handcuffs, the kind that might have been bought at a souvenir shop in town, with fake pink fur on the bracelets.

"When we're finished," she continued. "I'm not going to let you run downstairs to do your wanking or yanking. You're going to stay in that chair for a while until you cool off. Understand?"

I cast a quick glance at Tim, who was still relaxing on the bed, as if to ask him if this was for real.

"Dude, it's whatever she wants," was all he said. Then Cheryl told me I had ten seconds to make up my mind and started counting them down.

This was crazy. Something that would only happen in some bullshit erotic story that someone with nothing better to do would make up and post on the internet. Yet, there I stood, naked, and starting to get hard, my ex-girlfriend looking so fucking hot all dressed up for a romp in the sack.

"Okay," was all I said, the word almost croaking in my dry mouth.

When we had been together, I had told Cheryl of a dominatrix fantasy of mine. I had wanted to buy her some thigh high boots and a leather outfit, but she thought that was stupid. She was however willing to spank me with a ping pong paddle on a few occasions.

While that had been some hot foreplay, she never swatted me as hard as I would have liked. I suppose she loved me at the time and didn't want to hurt me. Therefore, I wasn't afraid of her spanking me with her shoe, and willingly bent over and grabbed the foot rail of the bed as I was told.

Her boot heels clomped on the wooden floor as she walked around behind me, and placed a hand on one of my shoulders as if to hold me in place.

The thin leather sole of her shoe slapped loudly on my bare ass, and hurt much more than I expected. The swats landed firmly on one of my butt cheeks and then the other, alternating in the predictable way she had spanked me with the paddle.

"You're a bad little boy," she scolded, as she swatted my ass even harder. She was taking the dominatrix role that I had always wanted. Perhaps not the same boots or paddle I had fantasized about, but sexy boots none the less, and the spanking hurt just right. Her confidence in the role excited me as well, and my penis was swollen with arousal. However, the spanking was lasting longer than expected, and tears were welling up in my eyes.

"I've had enough," I told her. Cheryl immediately stopped spanking me.

"Come on, you wimp. I know you like to be spanked," Cheryl said, and pulled me upright. "Look at that little boner of yours!" she squealed. "See, I told you he liked to be spanked," she said to Tim.

I hesitantly looked up at Tim, still lounging on the bed in front of me. He had a grin on his face and a large tent pole in his boxers, clearly aroused at watching his girlfriend spank my ass.

"You'll have enough, when I say you've had enough," Cheryl told me in a stern tone, waving her shoe in my face. She told me that if I didn't let her spank me some more, I couldn't watch them make love, and she would cuff me to a chair downstairs. "I don't want you listening outside the door or playing with that little weenie of yours."

Tim was laughing at me as Cheryl taunted me some more. Again she gave me ten seconds to decide if I would take more spanking, and immediately started the countdown.

Although it seemed she was none the wiser, the punishment was fitting the crime. Spanking me with her shoe that I had gotten off in earlier that evening, not to mention wearing the boots I had masturbated with earlier in the day.

There was no telling how much longer she planned on spanking me, but hoping that taking this short break would somehow make it easier to endure, I bent over submissively and held onto the foot rail of the bed once more.

Cheryl wasted no time and started spanking my ass once again. There was nothing playful or teasing about it. I was being punished. Even though I started to grunt and then yelp at every swat of her shoe, I told myself that I deserved it. After all I had spied on them, looked through their bedroom and masturbated with a pair of her boots and shoes.

For all I knew they would kick me out of their bedroom after the spanking. The promise of getting to watch them fuck having been a lie, and that would be my punishment and I would have to accept it. I gripped the rail with white knuckles, flinching as every swat of her shoe landed squarely on my ass.

"I think he's had enough, babe," I finally heard Tim say. The spanking stopped. If not for him she might have gone all night.

Cheryl grabbed me by one of my ears and led me towards the chair in the corner. I cooperated, not daring to resist her. She sat me down hard, the bare wooden seat painful on my sore ass. She fumbled behind me with the handcuffs, and I realized Cheryl had looped the chain through a rung on the back of the chair. I was not only cuffed with my hands behind my back, but also secured to the chair.

"Stop crying, little boy," Cheryl told me as the last of my tears from the spanking rolled down my cheeks. "Now watch and maybe you'll learn something."

She strutted over to the bed in an exaggerated runway walk, hips swiveling, sexy ass provocatively displayed by her thong panties, loose garter straps swaying. Cheryl leaned over and started kissing Tim, their tongues intertwining.

Cheryl took Tim by the hand and led him around to the foot of the bed, and they were only about five feet away from my chair. She wrapped her arms tightly around him. Tim was over a foot taller than her, and he leaned down to kiss her passionately. Cheryl kicked one leg back like you see on old movies, her silver cowgirl boot dangling in the air.

As they made out, she reached down to fondle the large package in Tim's boxers. He'd been hard for some time now and was no doubt ready to fuck her. Cheryl reached one hand in his shorts and pulled out his cock.

Then she knelt in front of him and slowly pulled his boxer shorts down around his ankles, keeping her mouth just inches from the end of his penis. Seeing his hard cock in the bright lighting of the bedroom, it looked even larger than it had last night. It had to be at least ten inches long and certainly thicker than mine. Standing firm and pointing up at a forty-five degree angle.

"You see that?" Cheryl asked, turning to face me. "That's a real man's penis." Cheryl playfully eased in and lightly kissed the tip of his cock. Her lips were shiny with lip gloss, and she wrapped them around the head of his penis, cheeks going concave as she gave him a few teasing suckles.

Tim gasped lightly, placed his hand behind her head, and tried to force himself into her mouth, but Cheryl wasn't done taunting me. Turning to face me once again, lightly stroking his cock, she asked,

"How long is Tim's penis? It must be twice as long as yours. Come on, look at yours and then look at his," she laughed.