Jillian's Naked Mile


All sorts of thoughts ran through my head. I had some fear invade my thoughts for the first time. What if? What if? I arrived at the pub so quickly that I didn't really have time to think those thoughts all the way through. It was no use anyway, I was committed. All these months of my games had led to this anyway, this type of night was inevitable. I looked at the line of cars parked at the bar. It was far more crowded than I'd figured. I saw a tall guy getting out of a red pickup and head in. I recognized him as Josh, he was a friend of my next door neighbor, Bob's. He was a frequent visitor to his barbeques.

I walked in uneasily. It was loud, smoky and full. Men noticed me right away. I was the tart in the revealing dress. My were boobs hanging out invitingly and there was more than a hint of backside than one could reasonably expect in a bar like that. I glanced at the pool table. It was packed, as I'd planned. Now though, I was starting to regret my decision to put it there. It's one thing to plan it with the heat of the thoughts overwhelming you, it's another to have to do it, in the cold light of a barroom.

Suddenly, a man appeared on my right and offered to buy me a drink. It was Josh. I smiled to myself that he worked that quickly. I eagerly accepted. He'd seen me across the fence numerous times, though never like this. I knew I'd need some liquid encouragement, for sure. I downed it while making small talk with him. He was clearly only interested in my chest, as he never looked me in the eye once. All the while I was planning how in the world I could get on the floor with all those people around and grope for the key. The first thought was to just do it. After my second drink, to just walk over, nudge someone aside. Just get on my knees and do it, and walk out. I figured that maybe the shock alone would stun them long enough. Luckily, I came up with a better idea. Josh had noticed my lack of attention to him and excused himself to walk over to the pool table area. I cursed myself under my breath for not at least flirting him up for the other drink. Any other night, in my current state of horniness, I'd have no doubt allowed him to see everything he'd been ogling and let him stick his hard cock in me out in the parking lot. I was that horny. I was going to get off soon but I needed to focus. I still needed to get that second drink, though, and time was a factor. One, Greg clearly had his usual schedule, I did not want to mess that up. Two, the two Sams were at her parents, as usual for a sunday, but always arrived home at about 10pm. So, I had to do it all before time constraints limited me.

I was starting to get frantic for that second drink. I almost cheated and ordered one for myself when I remember I'd left everything in the car, for that very purpose. I decided to be more outward about my flirting and I turned to a lonely man at the bar and gave him a good show of my cleavage while talking to him. Finally, he got the hint and bought me the drink. I barely had time to thank him before I finished the drink, slammed in on the bar and walked over to the pool table area towards Josh.

I could feel the eyes on me as I moved, it was intoxicating, yet nerve wracking. I put some change on the table, indicating my desire to play. I was well down the stacks of quarters, I knew I wasn't going to wait to actually play. I used it as an excuse to get in close. It was between games and I purposely starting chatting up Josh who was still clearly interested in what I was (wasn't) wearing. Since he was tall he could look directly down my dress. He was getting a spectacular show. I used his advances to begin my act. They were just about to rack the balls and break for the next game when I started my 'bit'. I frantically called out for no one to move, I'd dropped a contact lens. This led to several guys dropping to the floor on their hands and knees in search. I joined them. I knew what this would mean, I'd planned it, and I only wished I'd had the guts to look back to see their faces. But, there I was, on my knees, my skirt had to be halfway up my ass, at least. I could feel it in the air. My french cut panties had to be showing. I had to act like I didn't, but I knew they were looking, all of them. I could feel Josh, on his knees, behind me. He had to have the best look, from just a foot or two away from my exposed cheeks. I feigned for the men to look elsewhere while I looked under the table. I used that opportunity to peel the key away from it's hiding place. It was only then I dared a glance behind me, from under the table. Guys were elbowing each other in the ribs. I could hear them say things under their breath. I was tingling by now. I stood up abruptly, saying I'd found the lens. I pretended to put it back in my eye. I thanked the men for helping and I walked back into the main part of the bar. I saw the disappointment in Josh's face when I started to walk away. I then slipped quickly out the door. Part one was accomplished.

I stood out at my car with a smile. I knew I was crazy, I knew this game was going to be out of control nuts but I couldn't help myself, I was giddy now. My pussy felt like it was fluttering. This had only been the easy part. I was about to seal my fate for good for the night. I'd parked way back, behind the bar, where only employees park. I took my bag of goodies out and got right to work. First, I took off the dress and the panties. I was going to shove them in the bag when I had another spontaneous nasty thought. I figured, why not. I took the dress and the panties and walked to the corner of the bar, nude. I glanced around the corner, the coast was clear. I ran over to the red pickup truck and quickly tossed the dress into Josh's open window. As an afterthought, I hung my panties from his antenna. I ran back to my car. NOW I was going to have to hurry. I quickly put the ankle cuffs on. I opened the driver's side window just a smidgeon. I locked the car doors and removed the remote from the ring (my car won't lock all the doors from the inside.) Then, with reluctance, I put my handcuffs on. I briefly hesitated, before I clicked them shut behind me. I had a moment of panic. I actually pushed the remote to open the doors again. I got back inside the car. I was breathing heavily now. My ankles were still cuffed, I was still naked, and the handcuffs were still cuffed to one wrist. It was now or never. If I waited any longer my plans could be ruined. I could always do it another night. My pussy was on fire. I thought, fuck it, I got out of the car this time without hesitation. I locked the doors, slipped the remote into the car through the crack I'd left in the window and put the handcuffs behind my back and clicked them. That was that. I was now cuffed and naked with only my plans, wicked as they were, able to get me home safely.

I wasn't completely crazy (well, that's subjective). I'd actually planned it better than just being bound and naked and making myself walk in front of everyone on the street. There actually is a path from the alley behind the bar which leads to a park. I had to take this path to the park, go through the park, which led to my street, a half dozen blocks from my house. I began my walk. Almost immediately I regretted adding the cable which attached the leg cuffs. It was hard enough to walk with the high heels, adding the limited range of motion made it hard, very hard indeed. I could only shuffle, and even then, I nearly tripped every other step until I sort of got used to it. I didn't want to fall, I couldn't brace myself, my hands were behind me. I really hadn't thought that part out well enough. I should've cuffed them in front of me, at least for now. It was quiet enough in the alley and then the path. I really didn't know what I'd do if there was a drunk or bum hanging out back there. I shuddered at the thought, though strangely, it heated my pussy up another level. Fleeting thoughts would flash in my brain that maybe I wanted that, maybe I should come back someday when there are guys back there, that sort of thing. I was wondering why this stuff drives me crazy like this. I had enough troubles to worry about on this night, however, and my focus came back.

I was at the park now. I had to cross a reasonably busy street to get to it. I waited for the opportunity. As cars passed I kept thinking of my running clock, I couldn't wait long but I also couldn't just rush out with dozens of cars going by. Finally I saw an opening. I dashed/shuffled/jumped the best I could across the street. I wasn't quite to the treeline when I heard a car horn. I'd been seen. I hustled into the brush, and scraped myself on some branches. I crouched there, panting heavily. I waited. There was no one following. I gingerly extracted myself from the bushes and resumed my shuffling gait. I had a few hundred yards in the park then I exited it on my street. I still had blocks and blocks to go.

I began shuffling again. I stayed on the sidewalk. The streetlights weren't frequent and were placed at intervals between houses, not directly at them. I passed a house where I knew a cute guy lived. I'd walked past this house many times, hoping to get his attention. He was a pilot of some kind, and totally ripped. I'd have included him in my plans somehow, if I knew anything about him or his schedule, alas, I knew that would have to wait for another night. I more than secretly wished he was looking out his window then. I thought I saw him through his blinds. I ducked down. Maybe he'd notice me, my tits bouncing with my unsteady gait. I walked back in the other direction. I was under the street light now. God , I was horny, I couldn't believe I was messing with my detailed plan like this in trying to get myself fucked. I sauntered back toward the right direction, my sexy ass naked to the wind. I didn't see any movement. I tried again, down and back. It was no good. I had to move on. The hum in my pussy was growing. I resolved that I would absolutely punish it later, because of all of this teasing and abstaining.

A few cars passed and I ducked out of the way in plenty of time as they did. I got across the last cross street to my block but still had to wait what I considered too long. I could see Greg's house. I was exhausted from all the effort of the walk. I made a note to never try the hobbling effect again. I still had some physical activity left. I hoped I had enough strength.

I made it to Greg's. I figured it was after his dinner time, and hoped that it was still before his den time. As I approached I could see that his den light was dark. I shuffled along the fence line. His dog Sally approached.

I thought, "Fuck, what's she doing in the backyard?" I had to shush her from making too much noise. I was on the other side of the fence and my hands were behind me, it made that difficult. Still, I had wanted it hard and it certainly was. The plan was this: I left the two envelopes of pictures hidden. I'd drop off the first ones, the revealing but milder ones on his front porch. I'd ring the doorbell then shuffle the hell out of there to the backyard. Then, I had to hope he jerks off to them. While he was doing that I had to drop the second envelope on the front walk, the one he'll have to go on when he takes Sally for her walk. Then, I had to go back to the backyard and get the key and keep an eye on Greg's progress, so to speak. I had to hurry and get the ankle cuffs off, then race to the front where the pictures were and scoop them up before he finds them and sees me like that. Oh, I'm embarrassed to admit but in the car, on my way to the bar I was thinking how that the pictures alone wouldn't be embarrassing enough. So, I wrote a note and I included it among the racy pictures in envelope B. It was written like a coupon. It said, "This entitles the bearer to choose one of the pictures and have me in the manner of said picture" Then I wrote in parentheses, "You won't have to jerk off next time." I even left my email. Greg would be able to choose which position he wanted me in, cuffed and naked. Now that would be humiliating. He was in his 40's pudgy and balding, and by the looks of it, hadn't had a woman in years...if ever. I think that satisfied my desire for it to be risky and embarrassing if caught.

There was a pressing problem though, the time. I had taken too long at the bar, was kept too long waiting for traffic, then delayed myself with my slow back and forth walk for the cute neighbor.

I crept along the fence line. I found the packet I left by the fence. I opened it and took out the first envelope of pictures I'd taken of me. These were the sexy but safer ones. I made sure this was the right group of photos, I didn't want to make that mistake. Because of the time pressure, I had to make it go quicker. I figured I had but a half hour or less to get to Sam's and wash his car. I took the pictures out of both of the envelopes and laid them carefully in two piles. I wanted him to have at least one really sexy one in order to 'guarantee' him jerking off quickly to it. It was a struggle with my hands behind me but I managed it. I took a random one from the X rated pile and put it with the safer ones. I didn't have time nor the inclination to put them back in the envelopes, I had to hurry. I took the safer pictures and I shuffled quickly back to his front gate with them. I managed to get the gate open by backing up to it, I knew I'd better leave it open for my quick retreat. I hopped up to his front door. I dropped the pictures and rang his doorbell. I scurried like mad around the side of his house, through the gate to his backyard. This was where the ankle cuff key was. I heard the door open, a momentary silence, then the door shut again. I had the urge to go back and see if the pictures were still there but there was no need, the light went on in the den. I was on my knees facing his window. His den was in the basement, it was one of those bi- level houses. I knew he couldn't see me, it was pitch black behind me and his den was illuminated only by a desk lamp. I saw him fan out the pictures, a smile came across his face.

Suddenly, Sally came from around the corner and knocked me over. I couldn't stop her without my hands. She was all over me, nosing me, licking at me.

I thought, "Fuck, why is she outside?"

I had to placate her though, I didn't want Greg to notice. I did my best to comfort her but with my hands behind me my pats at her head made access to my behind too inviting. I almost ruined my whole plan right there and nearly screamed when I felt her cold nose press hard on my ass. The more I fought her, the more she wriggled. I looked in the window and saw Greg with his dick out, it was hard, he was stroking it. I knew I had to hurry and Sally was all over me. I'd buried the key next to the birdhouse, right outside his den window, purposely. I began to dig for it. I spend half the time digging, half the time pushing her away from my privates. I was so wet now, I'm sure Sally surely noticed it too. I dug furiously for the key while fighting Sally off. I could only laugh at how this had to look, me, naked and cuffed peering in a window with a guy jerking off and a dog's nose in my business. I finally got the key. Greg was working his hand more feverishly, I noticed he'd put one picture separate from the others. I knew which type. I rolled over onto my side, this limited Sally's intrusions. It was still no easy task but I managed to get the key in the lock. My face was just feet from the window now as I watched Greg shoot his cum all over his stomach to my pictures. I don't know why but at that moment I could feel my pussy get extra creamy. I had it, the key was open! I tossed the ankle cuffs over the fence for retrieval later, I kind of liked them for this type of play.

I locked the back gate on Sally and I raced to the front less encumbered than before, though I still had the heels on. I bent down to pick up the risky pictures. It was then I cursed my choice of not using the envelope. I tried picking them up by kneeling down and bending back but I kept dropping some, remember, I still had to carry my house key in my hand the whole time. I certainly didn't want to drop that. Sally saw me struggling and started barking madly. This no doubt is what brought Greg to the door. I saw the light come on, I made one last stab for the pictures, I got them....then dropped one or two...I think. The door was opening. I raced out the front gate and into the darkness. I found a dark patch of trees and huddled there gasping and chuckling to myself.

"Ok, so I dropped a picture or two," I thought, "what the hell, he already saw me in the other bondage one." I couldn't see anyone follow me and I saw his light go off again in the distance. Now I really had to rush. I eschewed the safer, darker route and walked across the street and down the sidewalk towards Sam's house. No one appeared to be out or in their windows anyway. I made it to his driveway. His prized car was under its safe car blanket. I quickly peeled it off. I went to the old stack of two by fours and such which lined the outer part of his driveway, they were always remodeling something over there. Behind the back one I pulled out what I needed, my netbook and a bucket of soapy water. I reached in for my prize.

"Shit, it's ice fucking cold!" I muttered to myself. At the bottom, I'd left the handcuff key. This time I easily managed the cuffs and I had them off. I left them cuffed to one wrist, no way was I giving these up. I quickly set up the netbook with the built in webcam. I had it set up on the concrete wall, about waist high. Once I was ready I turned on the webcam and pushed record.

I looked directly into the camera, bent over, my tits hanging down gloriously for him and I said, "would it look something like this?" I smiled, recalling what he'd said about me before. I took sponge out of the icy water and splashed it on my tits. I gasped at its frigidness but I tried not to let on. I then rubbed my tits all over the hood. I was careful not to use my hands on the car, only for the sponge. I repeated this all over the car. I even used my tits on his tires...the grazing across the rubber drove my already sensitive and now rock hard nipples crazy. I made sure I mugged for the camera throughout and repositioned it when necessary. I still had to be fast though. Then, I got the garden hose and rinsed it off, all the while playing suggestively with the hose as I did. I rubbed it into my pussy lustily, I even pretended like I was licking it like a cock. I finally doused my whole body with water, the chill invigorated me but did nothing to cool the flames building in me.

I thought of drying it off with one of his precious microfiber towels but I thought, "Fuck it, he's not paying me for this." I shut off the webcam. Then, I got on my aol account and sent the video to his email, also at aol. It was part of my plan. I could always unsend it, aol allows it when you send mail between its members. However, I'd need to get to either the netbook or my home pc before Sam comes home and opens his email or else I get the humiliation of him having that video forever, and what it might mean. I shuddered.

I hung up the garden hose and dug up the next key I needed, right under their flower pot. It was the key to our group mailboxes, the whole block's were in a group, on a post, just steps down the street from Sam. I hustled to the boxes, no longer encumbered by either set of cuffs. I opened the mailbox and slid the netbook in, it's slender, and the mailboxes are tall, tall enough for business sized envelopes. I took a deep breath and committed myself once more. I placed the key to the mailbox in with the netbook, my only spare key was at Bob's, my last task. Then, I put in my house key and closed it shut. Finally, laid the handcuff key on the ground behind the boxes, I had to be able to get them off to open the mailbox later. I now had to complete my last task before Sam got home. That could be minutes from now, though he might not go right to his email. Knowing that he's a hard charging salesman type and all, I was pretty sure it would be the first thing he did.

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byLaceAndHumiliation© 9 comments/ 148942 views/ 67 favorites

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