A Walk in the Dark

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He is caught on a naked midnight stroll.
2k words
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Part 1 of the 2 part series

Updated 10/28/2022
Created 07/04/2012
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3AM

I'm standing at the edge of an open field, completely naked. The field is very dark, I'm certain that nobody can see me. The only two pieces of clothing I have, sweats and a t-shirt, are attached to the tree in front of me with a wire lock.

*click*

I close the lock before I lose my nerve. I'm now completely vulnerable. The only way to free my clothing without tearing them to the point where they are useless is to get the key to the lock from my house. A bracelet with my house key is the only thing I'm wearing, hardly any protection. I know what I have to do.

Crossing the dark field is going to be the easy part, it's unlikely I'll get caught. Once I've gotten to the other side of the field I have to then walk three blocks through my well lit neighbourhood in order to get to safety. As I contemplate my situation the summer breeze brushes against me. I feel myself getting hard. Oh god, I have made a mistake. I wish I could unlock my clothes and put them back on right now. I should have never locked them up. This was a stupid idea, I'm going to get caught.

I recover from my momentary panic and force myself to take the first step towards the other side of the field. For now, at least, I am able to enjoy the walk, it is nice and warm out, the grass feels nice on my bare feet. Getting more comfortable, I pick up my pace, it is nice to feel so free.

As I walk I see a few lit windows pointing towards the field, I wonder if anyone inside can see me. I assure myself that it is too dark for anybody to see anything and I don't see any faces looking out the windows.

Too soon I reach the edge of the field, the easy part is over, now I have to step out into the light. I stand right by the lamppost, another step and I would be directly in the light. It is not far to my house, I just have to do it. I check to see if anybody is looking. Should I run or walk casually? My erection probably won't be helpful if somebody does see me. I don't know how long I stood there. Maybe if my heart wasn't beating so loudly I would have heard her walking up to me.

"Hi."

I froze.

"You seem to have lost your clothes."

I turn toward the voice, she had been walking along the sidewalk. I'm not sure how I didn't see her before. The street light shines on her, she's standing there in a summer dress. Absolutely beautiful.

"Can you talk?"

"Y-yes.", I clear my throat.

"Why are you naked? Some sort of dare?"

She gave me the perfect excuse for my situation. I should have said, Yes, just a stupid dare that got out of hand, can I borrow something to wear? Instead, "Sort of."

"Did you do this to yourself?"

I feel myself growing red.

"You did didn't you? Is that a key? What's it for?"

I'm not sure why I answered, "It's my house key."

"Hmm, would you like me to lend you something to wear? I'm sure I can let you borrow something if you play a little game with me?"

I was a little scared but this was much better than being discovered by somebody who would take offence to encountering a naked man. I shouldn't have agreed but I did.

"OK."

"Give me the key."

I handed it to her, another mistake, however she didn't know where I lived so she couldn't use it, but I couldn't get home either now.

"Follow me.", with no choice left I was in her hands.

I followed her back away from the sidewalk, into the dark.

After a few steps she turned around.

"On your knees."

There seemed no point is resisting, I lowered myself.

*snap*

For an instant I was bathed in light as the flash of her camera went off.

"As a souvenir. I was coming back from some night photography, you are my most interesting subject tonight."

"Here are the rules of my game: you are going to obey everything I say. You are going to be under my complete control. At any point you may leave and walk home naked, I will give you your key back, however I will not be giving you anything to wear. You want me to give you something to wear right?"

"Yes."

"I see that you are hard. This turns you on doesn't it? I'm curious as to what you would be willing to do for something to wear. Start stroking."

On my knees, in the middle of the field, with this beautiful woman standing over me, I started to stroke my own dick.

"Slowwwly."

"I have a feeling you like having somebody control you."

I continued stroking.

"The most important thing to keep in mind is that you don't come unless I tell you can. Let me know if you feel you are close."

"I should warn you that only you will be touching yourself tonight. You probably won't get see me, and you almost certainly won't be allowed to do anything to me. You should count yourself lucky if I give you permission to bring yourself to an orgasm."

"Stoke a little faster now."

*snap* Another picture.

She reached up her dress and pulled down her panties. She waved them in front of my face.

"If you play my game to my satisfaction I will give you these to wear, then you won't have to walk home completely naked, that seems fair to me."

"Are you enjoying this? I wonder how fast you can stroke your dick. Why don't you show me?"

I began stroking as quickly as I could. This combined with being completely exposed and having this woman telling me what to do meant that I was getting close to an orgasm much quicker than normal.

"How long do you think you can keep this up? Keep stroking as fast as you can. Stop right before you reach the edge."

It didn't take me long. I somehow managed to let go before I pushed myself over the edge.

"How close are you?"

"Really close."

"Hands at your sides."

She took my dick in her hand and started to stroke.

I groaned.

"So if I do this how long before you cum?"

"Seconds."

"How many?"

"5, maybe 10."

She let go.

"Good", she said.

"Rest for a minute."

She used the opportunity to take a few more pictures as I recovered.

"Do you think you can do that again?"

I had gotten really close, "I don't know."

"How many times do you think you can do that for me?"

Oh no, she said times, plural, "Don't know, not many."

"That was just your warm up. Here is the game. I am thinking of a number between 1 and 5. I want you to get to the edge that many times. Continue stroking until you are very close to coming then stop and let go. When you have done the correct number I will stroke you for 10 seconds, if you come in 10 seconds you win my underwear, if you cannot come that means you were not close enough and you will go home just as naked as I found you. So make sure you are no more than 10 seconds away from coming each time you let go. Ready? Go."

I had had time to recover slightly, amazingly my penis had begun to lose a bit of its stiffness. Despite this, it wasn't long till I felt myself getting near and let go. I didn't push myself too close, I figured whatever number she had in mind it probably wasn't one.

"Take a few seconds break."

She didn't give me much time to recover, "All better? Alright go again."

The second and third times took hardly any time at all. As I let go for the forth time since starting the game I realized the number she had picked must be five. I guess this wasn't surprising.

The fifth time I knew what was coming so I made sure to get as close as possible before letting go. As soon as I let go she took hold of my dick, gave me a couple slow stokes and then just held it.

She must have seen the agony in my eyes, I was so close.

"Aww, you were hoping to come? Not tonight. However you have beaten my game so I suppose you deserve some sort of reward, stand up."

She handed me her underwear. I reached out to take them but she hesitated.

"I wonder, would you chose to give up your reward if I gave you permission to give yourself those last few stokes."

I remained silent, I probably would have.

"Of course if I asked you to let me keep these panties you would probably just let me with no complaints, right? I could send you home naked, stiff, and frustrated."

"Please, no.", I still dreaded the thought of having to walk home without anything to wear.

"Why don't you put them on?"

I struggled into them but managed to put them on and partially tuck my hard dick into them.

"You look cute." She took a few more pictures.

She seemed about to hand my key back to me but hesitated again.

"Do you think you could edge one more time?"

Internally I groaned, I had really pushed myself close to the edge in the last one and wasn't sure I could take another.

"Maybe you need another reward. Having you obey my every order so well has made me very wet and I am no longer wearing anything under this dress, maybe I could give you a glimpse of what is under there? One more?"

I nodded.

"Good. I knew you could do it. On your knees again and then pull your new panties down."

Tucking my dick down had made me lose some of my erection, but I regained it quickly. Kneeling on the ground again I started to stroke.

"Same rules as before no coming without permission but bring yourself closer, at most 5 seconds away from the edge this time. I may even let you have an orgasm."

I was sure she wasn't going to but I brought myself back to the edge, backing off a few seconds before I though I needed to, the last time I had nearly gone over the edge without permission. I had a feeling I could still loose the little clothing she had given me if I disobeyed her rules.

I held my breath, recovering, as she held her hand over my shaft for a few seconds. She smiled at me and then gave my penis a firm but gently slap.

"OK, now for your reward."

She lifted her dress up. It the dim light I could see that she gleamed.

"Would you like to lick it?"

I moved forward.

"Stop.", she lowered her dress.

"Not today."

She handed the key back to me.

"Would you like another chance at coming?"

She was going to make me edge again wasn't she.

"Well not tonight, but, if you come here tomorrow at the same time I might decide to show up and maybe I'll let you come. Now enjoy your walk home."

As I started to walk away she called me back.

"Wait. If you do want to get another chance tomorrow you have make me a promise. Can you do that?"

"Yes."

"Promise me that you'll be a good boy and not masturbate between now and then."

Oh god, I was so horny, holding on for another 5 minutes was going to be a challenge.

"I promise."

"Your such an obedient boy, I'm glad I ran into you tonight."

I didn't hesitate this time as I reached the edge of the field. Walking though the neighbourhood still made me nervous but after letting a woman take pictures and order me to jerk off it wasn't so bad. At least my raging erection was somewhat hidden.

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8 Comments
Naked1Naked1almost 11 years ago
HOT

Damn that what hot...more please.

ValensGirlValensGirlover 11 years ago

Fantastic, fantastic. I just love the thought of her giving her her tiny panties to wear. And the edging was sexy too. Very hot.

AnonymousAnonymousalmost 12 years ago

Great beginning, add a few more chapters.

obscuredobscuredalmost 12 years ago

Kinky kinky kinky! Would like to know more about why he set up this dare for himself. If there was some connection to the girl, maybe (did she overhear him planning it?). Love this story.

Rossini12Rossini12almost 12 years ago
Cute story.

Interesting premise... will there be another night? Perhaps some oral tease? I hope so.

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