Jillian's Naked Mile


I started to cross the street when I got another surprise, it was Greg walking Sally. Oh fuck, how did I not think of that, of course he comes in this direction, I always give him a good titty show when he passes. He was headed towards my house, and Bob's of course, being next to mine. I had to cower in the bushes and watch him pass.

"Fuck, how long is this going to hold me back now," I fretted. I watched as he passed Bob's house, then approached mine. He lingered in front of my house, he let Sally smell all my pretty flowers on the way. I knew what he was wanting, another show. I couldn't give it to him now, I waited. Finally, reluctantly, he kept moving. He hit the end of the street and circled back. I waited breathlessly until he passed out of sight. Then, I raced across the street, nearly breaking the heel on my shoe in the meantime. I made it to Bob's fence and I crept along the edge, I was in my yard, so close to safety it was tantalizing. I couldn't get in, however, without tripping my alarm and having the police show up to arrest the naked girl in the lawn. I had to complete the task, get the other mailbox key, go back, get the netbook and the housekey and get home. When I got to the backyard I nearly blanched. Bob was there all right, but so was his friend Josh, from the bar! They were watching the tv he puts outside.

Then I remembered, "Fuck, that's right, it's not Saturday night like I'd wanted to do it on, it's Sunday night, and there's a Sunday night NFL game on, fuck fuck fuck" I cursed. I got my cellphone from the hiding place by the fence. It was supposed to help me with a distraction, now, it didn't seem likely that would work. I had my plan. The key to the mailbox I'd thrown in his pool. It was the above ground type. He'd invited me to swim in it whenever I wanted. I'd figured that I'd distract him with a call, tell him my car was dead a couple blocks up, to get him out of the backyard. I'd chat him up for a moment, tell him to hold on. I'd then jump in the pool, retrieve the key, get out quickly, get back on the phone, tell him I got the car started so never mind. Then I'd race back to the mailboxes. I have to be honest here. I knew I'd be plenty horny. I had no idea I'd be this horny though, I needed cock and I needed it badly. But, I figured that...you know what...if he catches me and I'm this horny...well....I had pretty much figured this task was about 50-50, half the time I'll make it, half the time he'll catch me and fuck my pussy raw. Either way, I figured it was win-win. Now though, the other man made the phone call distraction near impossible. I was beside myself. Ok, so I've admitted I wouldn't mind Bob catching me, I did not want Greg to, and most certainly not Sam. I was frantic.

Then, I had an idea. I skirted along the back fence two doors down, to Darla's. I knocked on her back door. She opened it with a big smile, seeing me dripping and naked.

"My, you've certainly had a most interesting night so far, from what I could see anyway, " she giggled.

"Darla, I know, and I'm sorry I can't talk, I'm in such a big hurry..." I panted between rushed breaths.

"Why? you are safe now," she said, eyebrow raised.

"Yes...no....soft of," I said haltingly. "I have to do something, and I have to do it fast or..."

"Or what, dearie"? she said with a sly smile.

"Or, well, I'm really going to have to do something or let something happen that I really don't want to."

"But, isn't that what you really desire for yourself? Isn't that why you do those things"?

"Yes, no, kind of," I said, confused by my own hesitance.

"You put yourself in these positions on purpose, you give up control, purposely, no?"

"Well, yes, I love not having total control, the risk, the danger, the exitement," I started to gush, "But I'm afraid that I might have gone too far this time, I really don't want to do some of the things I'd planned if it went wrong."

"So don't," she said concisely.

"You don't understand, they haven't happened yet, but will, if I don't do what I need to in the next, hell, ten minutes or so."

I could see her confusion, I quickly, and I mean quickly laid it all out for her, the keys the mailbox, Sam, Greg, and now Bob.

"Oh my, you have been busier than I thought," she chuckled, "and I thought the only show was the naked car wash, I had my popcorn and my feet up watching that one."

I blushed scarlet. "So will you help me"?

"I'm not sure," she said, her face now serious.

"Why not?" I begged.

"First, I' m not sure you want help. Deep down I think you want...hell, need these things to happen to you. Why would you even have thought of them? Second, I"m not sure how I can help you. And third...." she hesitated, " why should I, if there's nothing in it for me?"

I had to convince her, in a hurry. I threw it all out there. "Ok, look, I need you to call over there and tell them something, anything. Just make it good enough to get me enough time to get in and out of the pool."

"And?" she said with interest.

I sighed, I knew what I had to do. "...and then some time together?" I said hopefully. Like I said, I've had sex with plenty of women before, and she was attractive, in a forties, milf-lesbian kind of way.

"Doing what?" she prodded.

I was at wit's end, "anything you want," I said without reservation.

"Ok," she said, taking control. "Here's what we'll do. I'll call, I'll make it good."

I nodded.

"But, I get some things my way, starting right now, it won't disturb your game."

I agreed, "I said anything, ok, but hurry!"

She smiled, "Come here," as she pulled me to her and kissed me full on the lips. Her hands found my breasts and rolled my nipples through her fingers.

"Fuck," I thought, "It feels so good." I told her I needed to hurry. She told me to wait there.

She left and came back, she had clothespins in her hand.

"Oh fuck," I thought.

"Don't tell me you don't remember saying you loved the feel of these, hon."

I nodded modestly. She put them on me, I gasped. She stood back and admired her handiwork. She then twisted them playfully while I groaned.

"You are going to finish your task with these on, slut," she growled.

"Yes, ma'am," I said softly.

She then grabbed the loose cuff from one wrist. She twirled me around before I could protest and cuffed them on me again, leaving my hands helpless again behind me. I started to protest, "but how am I going to get the key from the pool like this," I moaned.

She laughed, "His pool is only 5 feet deep honey, use your toes." She then pushed me outside naked and cuffed again. "I'll be calling you soon Jillian, I expect you to come when called," she said sternly.

"Yes ma'am," I said defeatedly as I walked back towards Bob's.

I then realized the new problem immediately, I could't climb his fence that way, I'd have to use the gate. I walked towards it and waited for an opening. I could see across the street, Sam's car wasn't home yet. There was still some hope. Then, I saw the two of them go back inside. I found out later she'd asked them to come over and help move a couch. When they passed by I raced into the back yard. I climbed up the pool steps carefully, I still had heels on. Why I insist on being so strict with myself sometimes bothers me but it's what makes it all turn me on so. I slid into the water, again, it was icy. I nearly shrieked. I located the key and felt for it with my toes. I'd have it, then I'd drop it, have it again, then drop it again. My toes were cramping. I had no choice but to continue and I finally managed to get it to stay between my toes. I submerged myself and brought it up to my hands, behind me. I had it! Then I realized another problem. How was I going to get out, I needed the handrails and I had no hands! I had to bob up and down as it was, I'm 5' 2" and the water was 4, 4 1/2 feet where the sides were. I was in a panic, I was in freezing water, naked and from where I was I could see Sam's car headlights pull into his driveway.

"Fuck!" I screamed in my head. I went to the handrailing and I backed up to it, I began to walk myself up that way, backwards, using my arms to push me up. I got to the top and sat on the ledge. I got my legs over the rail, then I just started to slide down the outside of the ladder, getting some rough scratches as I went. The clothespins were still firmly in place, their bouncing sent electrical jolts through my nipples with each bounce. I got to the ground, I took a step, my heel buried in the wet ground, I fell forward into the grass, thank goodness it was a soft landing. I was face down in the grass, on my knees, my hands cuffed behind me and when I looked up I got the shock of my life.

"What the fuck do we have here?" It was Bob and Josh. They were staring at me in wide wonder.

"Oh my god," I started to gush, "I was just.....well you said I could...and I ...." I stammered, I couldn't even find words. He picked up my head by my chin.

"First, are you all right?" He said, somewhat bemused.

I felt my twisted ankle's soreness, but mostly the hurt was pride.

"Yes, yes, I think so," I said.

"Ok, then back to it, what the fuck are you doing?" He said, though not menacingly.

The two of them were staring. I was on my knees, I was sobbing now, my chest was heaving, I noticed the weight of the wet clothespins, the pain was searing me now.

"I was...I was just playing a little game with myself," I managed to choke, between sobs. "I was just...having a little fun."

"I guess so, " laughed Bob. "What is up with the cuffs and the nipple things?"

"I don't know...I just like them sometimes, you know?" I said submissively.

Josh hadn't said a word yet. "Well, I guess I can tell how you ended up naked after all," he smirked. He reached over to the patio table and grabbed my sundress and my french cut panties. "That explains why you are like this, and these were in my truck."

I looked away from the men in shame. I started crying anew.

"Look, you are ok, we're ok," he said, nudging Josh, "Right Josh?"

"Hell yeah, we're ok," laughed Josh.

I winced in pain. "Please let me out of these," I said, referring to my cuffs. They just shrugged, that's right, the key is in the mailbox. "Fuckkkkk," I moaned. "At least take the clamps off, they are hurting something fierce." I stood up and tried to walk but my ankle wouldn't allow it and I found myself on the ground again, even worse, I fell on my chest, the clothespins yanked violently on me when I hit. I screamed out.

"Pleeeeeeeeeeeeease take them off," I sobbed.

Bob looked at me with seriousness. "Sure, no problem, but first, I want to know how you got like this."

I just begged with him, "Please, just take them off, they are too painful and heavy."

"I will, once you tell me, the minute you tell me how you got here, just like this, I'll take them off, not a minute sooner."

I couldn't walk, the pain was unbearable, and they'd caught me doing the most embarrasing thing I'd ever done, what could it hurt? I told them. I lied a little (maybe a lot). I told them about the bar, that part was the truth. Then I told them how I made my way back here, leaving out the parts about Sam and Greg. I just told them about forcing myself to stop here and get the key. That satisfied them for the moment. He released the pins from my battered nipples. I screamed bloody murder. I fell to the ground. It was amazing, so painful, so embarrassing, so humiliating...so...maddeningly exciting.

I laid on the grass, recovering. Josh and Bob just waited me out. My nipples were still on fire, but now it felt like it was spreading all over me, but now it was a warm glow, seemingly connected directly to my pussy.

"I just want to go, " I said. "Help me up."

They did. I wobbled a few more steps then sat down on the deck chair. I took off the shoes finally.

"Do you want us to carry you home?" Bob asked, thoughtfully.

That familiar hum was now deafening, everything had led me here, to this, I was drunk on the thrill, intoxicated on the high. Being naked here, in front of these two rather beautiful young men, cuffed, all of my own choosing was rendering me unable to do the right thing, the sensible thing. All the planning the energy I'd put into all of it was now directly feeding my pussy. I didn't move.

"I said, do you want us to carry you home or can you make it, we'll walk with you," he said, more concerned this time.

"Yes, please," I sighed.

"Is that all you need?" Bob asked, as his eyes penetrated me.

"Sure, I'll walk, but could you do something for me first? Could you put the clothespins back on...I think I can take them again now."

They just looked at each other wide eyed. They both reached for them, each getting one. Each one attached one to a nipple. Another wonderful jolt shot directly to my core.

I fell back to the grass on my knees in front of both of them. I looked up at them and said, "are you sure you don't want something else first"? I said, my head not a couple feet from their crotches.

"Fuckkkk," they both said in unison. "Are you sure about this?" Bob said, all while pulling down his shorts. Josh already had his at his ankles.

"Um hmmm," I mumbled with a mouth full of Josh's thick, wonderful cock. I alternated on their cocks, slowly licking and savoring both of their beautiful dicks. I looked up at them.

I said, 'The clamps are hurting me really badly."

Bob reached for them. I said, "No, promise me you won't take them off until the end, even if I beg," I said sternly.

They both nodded dumbly.

"Seriously, no more dick sucking for you until you promise," I said, withholding my mouth from their cocks.

"Fuck no, we'll not take them off till we've cum in you," Josh gasped.

"Fuck no, not until we're through with your whore ass," Bob grunted, as my mouth engulfed him again. He even twisted the clothespins like a kid's airplane, just to illustrate his point. I nearly sank to the ground. I went back to their cocks, it was a blur. The pain was driving me to make them cum, hard. I don't even remember who filled my mouth first but it tasted like heaven. Then it was the other, I don't even remember the surroundings. I was in a fog. A beautiful, erotic fog. I'd lost the outside world, the adventure I'd planned was lost for the time being. I remember being carried to the patio lounger, placed on my face and then fucked hard from behind.

It was Josh. He said, "I wanted to do this to you when you were on your knees at the bar, your ass right in front of my face."

I said, "I know, I could feel it. Fuck me hard, fuck me like you want to," I moaned. I remember feeling hands raining down on my ass in wonderful spanks. My nipples were being pulled and twisted by the clothespins grotesquely as they were mashed into the cushions. I remember being pulled up roughly with the cuffs, jerking my arms up almost unnaturally. I was bent over the grill, it was still warm, though not hot. I was fucked again, my pussy was being pounded with abandon. This time it was Bob. I was lost. My pussy was on fire, I was sopping. I can't remember the first time I came but I remember the shriek I let out. I remember them cumming in my mouth, my pussy. I even remember one of them trying my ass, but being too spent to complete it. It was only then they took the pins off my nipples. I crumbled with a gasp in an exhausted heap on the grass. Both guys were laying on their patio loungers. No one said a word for the longest time.

I stood up, unsteadily. I picked up the mailbox key. "Don't bother getting up," I joked.

"Just a second," Bob said. He took the clothespins and clamped them on me again. "Just for the walk home," he smiled. I was almost jumping from one foot to the other by now, it was just too much, plus, after I'd cum the direct connection between the pins and my pussy was no longer direct.

I begged him to take them off. Then he said, "Ok, but we both will expect you back each Sunday."

After what I'd just experienced? Was I crazy? (perhaps) I said, "Yes, anything, just take them offfff," I begged.

"Don't forget the cuffs and these," he said, as he twisted off the clothespins, which made me gasp.

"I won't."

They both kissed me goodbye with long deep kisses. Their hands roamed freely over my used body. I broke away finally, reluctantly.

I walked away, I left my heels behind as another souvenir. I'd just reached the driveway of my house when I remembered Sam. "Son of a bitch," I thought. I ran back, nude, to the mailboxes. I opened it quickly and turned on my netbook as I rushed towards home. I was just inside the door, the alarm was now off, I checked my email. The first one was from Sam.

It read, "That has to be the worst car wash in history, what kind of soap was that anyway, it's all streaky. It may even be scratched, I should call the cops to at least write it up. It doesn't even look like you dried it. This is totally unacceptable. I expect you here, Wednesday night at 9 pm sharp to do it right, I'll have to supervise your lazy ass this time. Be dressed as you were. You should expect to also provide some sort of repayment for your ill chosen actions. If you aren't here promptly I have a number of friends at the club who would like to see a naked car wash, I wonder where someone would get a video like that? This isn't a request, it's a demand. I expect a reply."

I was shaking. I sighed in defeat. My hands could barely type out the reply, "Yes, sir, I'll be there promptly at 9pm 'dressed' as I was. I will repay you in any fashion you desire." I then hit send. My stomach churned. My pussy, however, throbbed.

I then noticed the next email, it was from Greg, of all people. I opened it with trepidation.

It read, "Hi Jillian, boy, was I surprised at the pictures, and wow, I must say, you are even hotter naked. I'm also surprised by the offer but I choose this picture and I have some free time on Tuesday. Please respond, so that I know I'm not crazy and just imagining this."

I looked at the attachment. First, it was the picture of me cuffed, hands behind, face down in the carpet, ass high.

"Oh fucking god," I said, my stomach tightening.

The other attachment was the coupon. They'd both fallen out of the pile when I'd tried to gather them up. I was almost sick. Almost trancelike, I typed out a response.

"Ok Greg, Tuesday it is, "I'll be dressed accordingly, is 9 pm ok?" and I hit send.

My front door was open. Darla appeared. "well, that certainly was interesting," she laughed. "I thought you wanted the distraction, why the hell did you come to me if you were going to let them fuck you anyway"? She said jokingly.

"I didn't, I wasn't....I wasn't planning on it, you cuffed me, that made it hard."

"You wanted it hard, right?" She said knowingly.

"Yes..." I said, head lowered. "Still, I tried my best to get out of there..."

"I know you did, hon, and you'd have made it too, if I hadn't sent them back on purpose for some tools," she said with a giggle.

My mouth shot wide open. "Don't look so surprised Jillie, you wanted it, you really did, you can't deny that. I'm a woman too, you don't think I could tell what you needed?"

I nodded softly, "but you don't know what you did," I said, "now I am on the hook....to everybody...including you."

"And isn't that also what you really, truly wanted?" She said cooly.

I started to protest. I stopped. I wasn't even sure of the answer.

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by Anonymous

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by Anonymous12/30/16


As a person who thinks as your character seems to, I thoroughly enjoyed reading about her adventures. One night during the summer a few years ago on a personal dare, I stripped myself naked and lockedmore...

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by Anonymous11/21/16

Your such a fine inventor of sexy fun incounters I wished that I was a nieghbor of yours.

It took me two nights to fully read this story and the ending was so hot, the fact that you got caught and had to surrender yourself to each one of them , I think that the next time you get in the modemore...

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