Oh god, not again

'No, Jennifer, please. Don't stop.'
'Perhaps if you begged, Julian.'
I didn't even have to think about it. The words came tumbling out.
'Jennifer please, I'm begging you, I'll do anything, just don't stop. Please please please don't stop.'
In the darkness there was no way of knowing if Jennifer was thinking about my request or had gotten up and was preparing to leave.
'Please, Jennifer, anything.'
Hot breath again on my glans. It felt so good. Then I felt her tongue licking from the base all the way to the tip, slowly. Jennifer had always been good at giving oral sex but this was something else entirely. I felt a current running all the way from my loins to my chest, transfixing me. She took me into her mouth and started moving up and down while her hand cupped me and massaged my testes.
'Feels good, doesn't it?', Dr. Strange's tongue was almost in my ear. Her proximity sent a chill down to the base of my spine.
'But it has a price.'
Jennifer's hand was now less gentle. She had stopped her massage and was crushing my testes lightly in her hand. The feeling of her soft tongue wrapping itself around my penis was so exquisite I thought I would come. I moaned softly. The pressure on my testes now became painful but Jennifer kept moving her head up and down, up and down.
'You see, Julian, Ms. Chance now controls both your pleasure and your pain and through those, you. If she wishes she can give you ecstasy, if not, torment.'
Jennifer now had my testes in a vice like grip. It was painful, and getting more so.
'The lesson is obvious really. All you have to do is beg.'
The pain was now almost unendurable.
'Jennifer, please stop. I can't take it anymore. Jennifer. Please. You're hurting me. I'll do whatever you say just please stop. Please. Jennifer.'
Jennifer relaxed her grip. She started rubbing my penis while Dr. Strange pinched my nipples and breathed heavily into my ear. It was no time before I exploded. I had learned my lesson. Jennifer was mistress of both pleasure and pain.

I felt a finger brush my anus and then begin to burrow there, lightly. I felt a thrill of fear somewhere deep in my loins.
'So here's what we're going to do now. I'm going to show you how to put on this strap on and then you are going to fuck your husband. While you're doing that your husband is going to pleasure me orally. As long as I'm satisfied I want you to be gentle, but the moment I feel him slacking off I want you to really pound him. Be merciless. This is his first time being penetrated and therefore the best time to leave a mark, when the experience is still new and he's not ready for it.'
'I understand.'
'Good, so let's just strap it on you.'
'Julian', I could hear her voice whispering in my ear as she ran her fingers through my hair, 'I'm afraid I don't have any lubrication here so this might become rather painful. But I'll give you a chance to lubricate the strap-on yourself.'
'Ms. Chance, come here please.'
I saw my wife walking into my field of view. The strap-on was red and partially transparent. It bore a rather strong resemblance to a fairly large penis. So large, in fact, that I was worried if I could fit it in.
'Now Julian I want you to take that big red cock in your mouth and suck on it like you mean it.'
I didn't know exactly what to do. Jennifer came and stood directly in front of me the strap-on almost touching my lips.
'Go on Julian, you know what to do.'
I felt her hand on the back of my head pushing me forward until my lips touched rubber.
'The more you lubricate it now the less it will hurt later. Come on now, you know you want to.'
Jennifer smiled above me. I felt something push into me from behind. I didn't know what it was but it was slightly painful and made me lurch forward some more. I felt the strap-on in my mouth. I started licking it.
'Open your mouth Julian,' said Dr. Strange in an impatient voice. She jammed my mouth straight onto the rubber cock until I almost choked.
'Now suck it. Suck it like you want it to come in your mouth.'
I sucked it. It was a strange feeling, having an artificial penis in my mouth, feeling all the ridges and realizing that was how Jennifer felt when she gave me head.
'That's a good boy. Move your head up and down.'
I realized that the longer I was going to do this the more time I would have before the next punishment so I decided to do a good job. It was humiliating to be in this position, watched by two women, but I preferred it to the pain that I knew would come after. So I licked the glans slowly and took it into my mouth and sucked it and licked the stem and gradually felt myself getting into the act despite myself.
Dr. Strange's fingers curling into my hair and forcing it away from the strap-on stopped my act.
'That's enough.'
Jennifer and Dr. Strange traded places. Now Jennifer was behind me doing something I couldn't see and Dr. Strange was in front. Dr. Strange released the chain that was holding me bound to the table slightly and I felt Jennifer's cool hands taking me by the pelvis and pulling me back. Dr. Strange took her boots off, pulled her skirt up to her hips and sat on the table right in front of me. Her huge pelvis blocked out the rest of the surroundings. Her nether lips were completely smooth and in a way all the more intimidating for it. I felt Jennifer's strap-on touch my anus and I started forward, which brought my nose into direct contact with Dr. Strange's vagina. I half expected it to smell of a hospital disinfectant of some sort but it was odorless.
'Good. Now lick. Do a good job.'
As my tongue tentatively thrust into her vagina I felt Jennifer penetrate me authoritatively. The strap-on forced my anus wide open and then rammed its way in painfully. The tip was deep inside. I groaned with agony.
'Shhhhhhhh…you're doing well. Don't stop.'
My tongue glided over Dr. Strange's vagina, my saliva mixing with her juices. I heard her breath quicken and pushed my tongue deep into her, then twirled my tongue around her clitoris. Dr. Strange let out a long, low moan of satisfaction, took hold of my hair in one hand and pulled it painfully.
'That's a good boy.'
Dr. Strange's mounting excitement evidently aroused something in Jennifer too because she started pumping in and out of me faster. My saliva must have dried up because each thrust was more painful. I found I could not hold out any longer and let out a cry of pain.
They both stopped. Dr. Strange brought her breath back to normal but I could tell she was angry.
'Julian. I told you to do a good job. Screaming in the middle of oral sex is not doing a good job. If it was anyone's fault that the strap-on was hurting you it was your own. I gave you every chance to lubricate it properly. You're going to have to be punished.'
'Ms. Chance, now I really want you to give him a reason to scream. Julian, you bury your head in my vagina and lick it well otherwise I'm going to become very angry.'
Jennifer roughly took hold of my pelvis in her hands and started pumping in and out of me furiously. I thought it had been painful before but now strap-on tore in and out of me and it was only my fear of Dr. Strange that prevented me from shouting with agony. I squirmed and tried to wriggle into a position that wouldn't be so painful, all to no avail. I stuck my tongue out as far as I could into Dr. Strange's vagina and licked frantically, while desperately ransacking my mind for any technique I could think of which would please her. My efforts incited her passion and she began to thrust her pelvis into my face and moan loudly. Jennifer continued to fuck me, only occasionally stopping to give me a quick spank or push my head deeper into Dr. Strange's pelvis.
Dr. Strange's movements grew more and more frenzied and eventually she reached her crescendo, drenching my face in her juices.
'That was good, Julian, that was very very good.'
She breathed heavily above me.
'I hope your lesson has been learned.'
Slowly, she stood up on the table. From my position I had a good view of her ankles, but that was about it. She was so far above me her voice may as well have come from heaven. So were the drops that spattered over the back of my neck. I'll never know if they were the remains of her juices, or something else.
'I need to talk to you outside Ms. Chance.'
Dr. Strange got off the table and took Jennifer outside. I was left alone, tied to the desk. I was cold and it was very quiet. I reached back with my hands to feel my buttocks. They were warm and smooth and very sensitive. I still keenly felt the aftereffects of the strap-on's invasion of me. I also noticed a peculiar tingling around my hairless crotch, around the area where the chain held my penis in a tight and chilly embrace. I couldn't really call it pain, but it wasn't a pleasant sensation either. Above all I felt alone and exhausted. It was a peculiar feeling, but I longed for the return of my two tormentors. I wanted some company, though I hoped it would not mean more punishment. I wanted some human touch and warmth. I wanted it all to end.
The silence stretched on. I strained my ears and tried to hear any voices outside but all was still. In the continuing emptiness I started to wonder what else Dr. Strange and Jennifer had planned for me. They had been gone for so long I started to think they had abandoned me. Would she really do that? I was her husband after all. I loved her. And I thought she loved me too.
The door opened and I heard two sets of footsteps approaching. Silently, someone covered my eyes with a piece of cloth while the chain was detached from my penis. Then I was pulled back and set on a chair. My hands were tied behind the chair's back.
Again there was a pause of a few moments. I could discern no movement and half-formed images of possible tortures flashed through my mind. Then, through the haze of my thoughts, I felt hot breath on my crotch. It might have been going on for a while, I'm not sure. The cold must have numbed the area. The faint waft of hot air washing over my penis slowly brought it back to life. It felt almost like a caress, like all those times I had lain by Jennifer in our bed after making love when we had embraced and felt our warm skin touch and almost fuse together.
'Julian', Dr. Strange's voice whispered in my ear, 'that's Ms. Chance there. Wouldn't you like for her to touch you?'
I tried to say something, failed, clear my throat and tried again.
'Y-yes. Very much.'
'Why don't you ask her to touch you?'
'Jennifer would you please touch me?'
'Louder, Julian, I don't think she heard you.'
'Jennifer, please touch me.'
I felt Jennifer's warm fingers stroking my cock, sending a gentle thrill up my spine. I felt an erection start to form.
'Julian, is there anything else you'd like Ms. Chance to do?'
I hadn't been thinking until now, lost in the pleasure of Jennifer's touch on my body, but as soon as I heard Dr. Strange I suddenly realized there was something I wanted very urgently.
'Yes.'
'What is it?'
'Jennifer, can you please take me into your mouth?'
Dr. Strange drew a sharp inward breath. Jennifer didn't stop her stroking. By now I was fully erect and I was sure it was one of the most impressive erections I'd ever had. The earlier torture at the hands of Dr. Strange and Jennifer had awakened something deep inside me and I felt I must have Jennifer. I must have her touch me. I wanted to feel her mouth, to hold her, to penetrate her.
'Julian, that's a very impertinent request. I'm not sure what Ms. Chance will think of it. In her place I would of course do nothing of the sort. Indeed, I would punish you for even suggesting it. But Ms. Chance and I are of different disposition. Perhaps she will grant your wish?'
I felt Jennifer's breath grow ever closer to my glans. My breath grew shorter. Then she pulled away and stopped caressing me.

I looked up, straining my neck.
'Julian, until we complete the treatment, you're mine. I want you to know and realize this fact. I won't stop until I think you've changed your behavior for the better.'
She fastened the chain to something under the table so I was stuck in my prone position. I heard her walk over to the cupboard, the sound of her heels echoing throughout the high-ceilinged room, and open it. Then she walked up behind me and paused. The room was cold, and now that I didn't have any clothes on I started feeling it. I felt my muscles grow slightly rigid and slight tremors rocked my body. I wasn't sure if this was purely the result of the cold or had something to do with the fact that Dr. Strange stood behind me and I had a feeling that whatever she planned to do next wouldn't be pleasant for me.
'Jennifer, what's happening?', I asked plaintively, 'I can't believe I'm naked and chained in front of a completely strange woman. What are you doing?'
'Julian', replied Dr. Strange, 'as I said before you are my property now. You will address yourself to me only from now on, and that only when I tell you to. You are not to speak to your wife unless I give permission. I will punish this transgression first, just to start things properly.'
There was a whooshing sound and I felt a sharp sting across my buttocks. The blow was so powerful I was pushed forward slightly across the desk.
'One', said Dr. Strange with a hint of a smile in her voice.
'Two', she said slowly as another blow landed on my buttocks.
'Three'. This was beginning to get very painful. Jennifer had never been so hard in her punishments, something I'd failed to appreciate before.
'Four'. The blows took a long time from start to finish. I guess Dr. Strange believed in wide swings. From the start of the sound of the whip traveling in the air until it landed on my backside I had enough time to develop a dread that had me jump in my place and clench my muscles even before the blow landed.
'Five.' The whip was wide, I felt each blow on every inch of the skin of my buttocks.
'Six.'
'Seven.'
'Eight.'
'Nine.'
'Ten.'
She stopped. I had been just about ready to scream to Jennifer for mercy. I didn't know if the whole thing had been her idea or not or if she had even had an idea of what was coming. But she must have been able to stop the punishment. She was my only hope. I had never felt such pain in a whipping before.
'Now, Julian, I hope we understand each other better now. From now on whenever I tell you to do something I expect your unhesitating obedience. Before we are done you will extend the same attitude to your loving partner. We need one more act of preparation before we can begin the treatment.'
She walked back to the cupboard, slowly. Then she came back. I wondered what more she had in store for me. I felt her apply something that felt like a viscous cream to my buttocks.
'What are you doing?', I asked.
'Hush, now. I don't want to have to repeat your lesson again so soon. You'll find out soon enough.'
She loosened the chain slightly and turned me over. She towered over me, all in black and holding a bright blade in her hand.
'No!!', I screamed, 'Jennifer help me! Don't let her do this!'
'Be silent!', she said and slapped my testicles. The pain was excruciating. I gasped for breath and she took the tip of my penis in her hand and started shaving around it. Through the pain that made my eyes smart and my head buzz I felt relief. She was just going to shave me, not cut it off.
She did an expert job. In several long, sure strokes she had the whole of my penis bare of pubic hair. When she finished Jennifer came forward with some lotion and massaged it into the shaved area. The feeling of her kneading it into and around my penis caused an erection and Jennifer gave me a disapproving glare, as if I was shaming her with this display. While Dr. Strange went to bring something else from the cupboard she cupped my testicles and crushed them slowly. The pain brought back the memory of Dr. Strange slapping them but did nothing to diminish the erection.
Dr. Strange came back and flipped me onto my stomach again. The cream she had applied before had hardened. She started tearing strips of it off my skin. I yelled in surprise at the pain of my hairs being torn out but she paid no heed. When she was done my buttocks were smooth too.
'Now, Ms. Chance, for most men being penetrated is the ultimate demeaning experience. Over the years I've found it to be the most effective tool in my arsenal when it comes to training men to be more obedient.'

Everybody makes mistakes. OK, so maybe this one was different. I knew it was different, that it was much worse than usual. Still, I don't think it was that bad. Did it really merit the punishment? I still don't think so.
Jennifer came home that night quite late. I could tell she was furious. She didn't fly out in a rage. She's not the type. But she was mad. I could read the signs. And really, she had every reason to be. I messed up. Badly. I knew that. Jennifer didn't get mad easily but when she did it wasn't a pleasant experience.
She had started my education a few weeks after our marriage ceremony. I still remember the first time. I'd forgotten to wash the dishes and she'd come back after what had apparently been a long and frustrating day. She took me to the bedroom and gave me a good talking-to. Then she told me to step out of my pants. I was a bit surprised at this turn of events but glad to end the unpleasantness. But Jennifer had a bigger surprise waiting for me. I was expecting sex but Jennifer had other ideas. Just as my penis was starting to become erect she took me across her knees and started spanking me.
Now, don't get me wrong, Jennifer's no bodybuilder. I could've gotten up anytime I'd wanted to. But the fact of the matter is that the shock of the moment mingled with my guilt and Jennifer's overbearing attitude did more to ensure my submissiveness than any amount of physical strength could have had. Afterwards I guess Jennifer felt mollified and even slightly contrite. Perhaps she thought she had gone too far. My buttocks were so sore that even her caresses were painful. So she laid me on the bed, face down, and smeared some cool lotion on my buttocks. It was pleasant, but hardly made up for the long moments of agony and humiliation which had come first. It was days before the pain subsided completely and weeks before I made any more mistakes like that.
Eventually I forgot about the pain. It was only natural. But each time Jennifer caught me out she would take me across her knees and spank me. Sometimes, when I did something really bad she would tie me to the bedposts standing up and whip me with a sharp little crop I didn't even know she had before our marriage.
This time, however, I knew I'd gone to a whole new level. To my surprise she didn't punish me, not right away. That night I had trouble sleeping. Jennifer refused to talk to me and I didn't really know what was coming.
In the morning Jennifer told me we had to go see a counselor. I didn't think it was a good idea but tiredly agreed. A few days passed and things seemed to go back to normal. I thought Jennifer had decided to let the matter drop. I couldn't have been more wrong.
One day I came home from work to find Jennifer waiting. She told me we had an appointment with the counselor. We got into the car and drove. Jennifer was as chatty as usual. I didn't even know why she wanted to go through with this. I'm more of a let-bygones-be-bygones kind of guy, but I know that Jennifer isn't. Still, if she wanted to talk, I could talk. And if she wanted a counselor, well, I wasn't a complete stranger to the world of therapy. I didn't mind.
The counselor's office was not what I expected. There were no books and no sofa. There was one cupboard in a corner that went all the way up to the ceiling and a huge teak desk backed by a plush chair. The counselor was sitting on the chair when we came in. Even sitting down she was an imposing woman. Every inch of her seemed designed to signal severity and dominance. From her shoulder length black hair, through to her large and shapely breasts and down to her long, and yet far from brittle, fingers. It was her eyes, though, which were her most alarming feature. Even behind her thickly framed black glasses it was hard not to notice how blue they were. They weren't deep or penetrating or bright or any of those things which usually make eyes unusual. They were just blue. Intensely so. I'd never seen anything similar and I hope I never will. I couldn't hold her gaze for more than a moment.
'Welcome, Ms. Chance', she said from the depths of her chair, 'it's good to see you again. I see you've brought your husband.'
We stopped in front of the desk. There were no chairs, oddly. Jennifer stood slightly behind me.
'Thank you for seeing us Dr. Strange.'
Dr. Strange smiled a little smile which did nothing to diminish from her commanding aura.
'Well, we have no time to waste. You've already told me of your problems, it's time to begin the treatment. Ms. Chance…', she motioned towards my wife. I felt Jennifer's thumbs in the back of my pants and felt her sliding them all the way down to my ankles.
I was more shocked than I'd ever been in my entire life. Here I was in an office with my pants around my ankles being examined clinically by a woman I'd only met about thirty seconds ago. The worst of it was that it was my wife who was the cause of all this.
'The shirt too', said Dr. Strange. I was limp with mortification. I felt Jennifer slide my shirt over my head. Except for my socks and shoes I was now completely naked.
'Julian, do you know why you're here?', asked Dr. Strange.
I couldn't even shake my head, let alone talk. Dr. Strange ignored my non-reaction.
'You're' here because you've stepped over a line, a boundary. On the one side is behavior I would expect of a loving partner and on the other is the kind which puts the whole relationship in jeopardy. Ms. Chance would like to continue your relationship but I've told her that if your present behavior goes on that will be impossible. Now you are here so that I can put your relationship back on track. First I'm going to treat this latest lapse in your behavior and then I'm going to show Ms. Chance how to keep you in line.'
She stared straight at my penis for a few seconds as if considering her next move. Then she got up, blindingly fast, and attached a chain to the base of my penis. I felt the chill of it enveloping my penis and continuing all the way to the tip.
The chain seemed to be attached to something below the desk, from my position I couldn't tell exactly what. Dr. Strange got up, she was quite a bit taller than me. She gave a quick, hard pull to the chain which forced me to lie down on the table.
'Julian, look at me.'

Mercifully, the wide-eyed one decided to take that moment to turn tail and run. Her companion, with one last regretful look, followed.
My tormentor couldn’t restrain her amusement anymore. Peal after peal of delighted laughter burst forth. I stood helpless, not knowing what to do. Covering my penis with my hands seemed pointless. I couldn’t leave since she still had my pants. I didn’t even know if I wanted to. Like a gambler who keeps losing but keeps upping the ante certain that the next hand will be his to win, I wanted my reward.
Eventually she stopped laughing. Wiping tears from here eyes she noticed my hurt expression.
“Come on, you enjoyed that at least as much as I did. Look, you’re still hard”, she said as she let the tips of her fingers lightly brush my glans. She was right. Not only was I still fully erect but there was now a thin but steady stream of precum which flowed along the shaft.
“Poor you”, she said and stroked my cheek. Then she bent over, lifted my shirt and kissed my nipple, hard. Almost a bite. Then she stuffed my shirt into her bag. I was completely naked now.
“Come on, not long now”, she took my hand again and started walking. Soon we arrived at a corner of the wall. Over the battlements we saw the waves crashing close, almost climbing over the wall.
“And now for the third and final challenge. But first let’s take the butt plug out. Here I’ll help you.”
She reached into her handbag and brought out a small remote control. She pressed a button and I felt the butt plug vibrate violently inside of me. She smiled as she saw I now realized it was she who had made it move earlier. The butt plug/vibrator slipped out and fell into the low grass beside the wall. She stood before me, looking at me, examining me from head to toe. Again I was struck by her beauty. I longed to touch her and feel her skin on mine.
“You want me, I know that, and I want you. But I want you to prove yourself to me. If you succeed in this last challenge you can have me. So let’s start. Look over the wall.”
I turned and looked. The stone was rough against my torso, the front of my thighs and penis. Bending over I looked at the sea. I felt her hand as a light weight on my back.
“What do you see down there?”, she asked softly. I barely heard her over the rumble of the waves.
“The sea.”
“Will you take the last challenge for me?”
I noticed a change in her voice, suddenly not so playful anymore.
“Yes.”
“Here it is.”
Something pressed against my anus again, stretching the walls, slipping inside. At the same time I felt the fabric of her dress against my buttocks and thighs. Her hair brushed my neck.
“I’m going to take you like you want to take me”, she whispered.
She began pumping in and out, slowly at first, then with an increasing tempo. The strap-on filled me completely and every time she slammed into me I felt its tip like a cold spot in my stomach. I felt completely mastered.
Faster and faster she fucked me, harder and more brutal. I started grunting with the pain but that only seemed to encourage her to go faster. The waves came higher, driven by the wind.
“Yes, yes, scream for me now”, she shouted.
I screamed, my voice almost drowned by the roaring of the waves.
“Louder, louder.”
I felt an animal desire. She was possessing me, filling me, taking me. The spray from the waves now landed on my face covering it with brine. Still she drove on. She grabbed my hair and lifted my head from the wall. Panting, she licked my ear.
“Almost there”, she breathed, “almost there”.
She let go of my hair and took me by both sides of my pelvis. Before I’d thought she had been rough but I was mistaken. Using her hands she impaled me on her dildo. She went in deeper than I thought possible, shouting with pleasure and delight. I wasn’t sure if the salt on my cheeks now came from the sea or my tears. I feared every stroke but also welcomed the pain. I wanted her to enjoy me. I started pushing myself onto her with every stroke.
Suddenly she stopped and shuddered. She took several deep, juddering breaths and then collapsed on top of me.
“You...passed.”

“But what if there’s someone else?”
“It’s all part of the challenge. Anyway, don’t be such a baby, it’ll be fun. When was the last time you had an opportunity to walk around naked in a castle?”
I let her slide my pants all the way down. She put them in her bag, took my hand and we started walking.
I’d seen few people on the walls before but I was worried nonetheless. I didn’t relish the prospect of appearing before a couple on a tryst out with only my shirt on. It was one thing to be naked in front of a woman I desired but quite another to be exposed before people I didn’t know. I might even be arrested. On top of it all the butt plug seemed always to be slipping out. I had to clench every muscle to keep it in place but it was almost as if it had a life of its own. Every now and then I was sure it trembled slightly as if trying to escape its prison. I clenched my muscles even harder but that only brought me into closer contact with its cold body. After a while the cold was so intense it was painful.
“You’re so quiet”, she said.
“I’m a bit uncomfortable. The butt plug is very cold.”
“Don’t worry, you’re doing fine and by the looks of it I’d say you were even enjoying yourself”, she said and glanced at my tumescent penis. At the tip a drop of precum twinkled in the moonlight.
“You’re not in any pain are you?”, she inquired solicitously.
“No, I...uh”.
There were soft noises on the path ahead of us.
“There are people there”, I whispered.
“So, you’re not afraid are you?”, she said in an alarmingly loud stage whisper.
“Well, actually I am. I don’t want to be arrested.”
“Hmmm...”, she considered, all the while pulling me closer to the voices. I was beginning to panic. I stopped, too afraid to move on.
“I have an idea”, she said brightly, slapping my penis for emphasis, “the further you go the easier I’ll make the last challenge. I’ll give you a point for every step you take. Every step is worth one percent. So if you take 50 steps it’ll make the last challenge 50% easier! How does that sound? That last challenge could be p-r-e-t-t-y difficult.”
I didn’t like the sound of that. The truth is I had no idea how I’d even managed to get this far. I was aroused, more aroused than ever before. But through the haze of alcohol and testosterone I felt shame and humiliation trying to push through. I was midway through the challenges and I didn’t want to stop now, but I was also aware that my feelings about this moment would be quite different tomorrow. I hesitated. Finally my more immediate needs won over prudence. So I strained my eyes and ears and started inching forward. I didn’t even know how she would translate the difficulty of the challenge to percentage points, but somehow I felt I had no choice but to trust her.
“Come on, you can take bigger steps than that. Those are baby steps!”, she said and demonstrated a step so wide it was almost a split. It also had the effect of hiking up her skirt, revealing a pair of perfect, tanned buttocks separated by a black thong.
“Oops!”, she said bashfully.
“Shhh, please be more quiet”, I begged.
“Sorry”, her eyes twinkled.
I continued my advance. Any moment now I would be revealed, a pervert exposing himself before a couple on a romantic night out. The butt plug gave another quiver and almost slipped out. I reached back with my hand to stop it but she slapped it away.
“Uh-uh, no hands”.
The butt plug was almost out. I could feel it. And when it crashed to the ground so would my hopes of winning the challenge. I bent over quickly, butt high in the air, hoping to let gravity slip it back inside of me. I relaxed my muscles, trying to ease its way back in. Slowly, it slid back in.
Finally, I managed it. With a final twitch it made its way back into its place. I straightened up and saw she was laughing breathlessly, almost unable to keep upright. I grudgingly admitted there was something comic about the whole situation but still felt resentful at the way she enjoyed it so.
But then a movement on the path drew my eye and I realized something worse, much worse, was going to happen to my self esteem. My exertions had made me oblivious to the voices stopping, but now I realized that their owners were standing on the path right in front of me. Two girls, about 17 years old, were standing on the path. One was wide eyed with shock, the other wore a delighted expression on her face. She was staring right at my penis which was twitching slightly under her gaze. I’d never felt so exposed and ashamed my whole life.

I tried not to. I wasn’t even sure why. I wanted to kiss her right then but felt it would ruin the moment. The only way to feel her lips on mine would be to continue with her game, somehow I knew that. She massaged my scrotum slowly. Words tumbled out disjointedly and I tried to pick up where I had left off.
“I...that is they...the empire”, her face was a mask of innocence. I tried bringing up images of ruined castles and dead warriors but all I could see were her red, smiling lips. I couldn't complete one word, let alone a whole sentence. My eyes closed of their own accord, but that only intensified the sensation of her cool fingers on my crotch. I took a deep breath, then another, and somehow managed to calm myself. Barely. Somehow I managed to continue.
“Very good, let’s go straight to the next challenge”, she leaned in and whispered in my ear.
She bent over and with one smooth tug pulled my pants down to my ankles. She made a circle with her finger in the air, instructing me to turn around. I knew I could never have gone along without the aid of the wine, but I felt the blood rushing all through me and a strange sense of freedom from the mortification that I would normally expect to appear in this situation. Of course it helped that I had never felt more aroused in my entire life.
“What are we doing now?”, I asked.
“You’ll see.”
She put one hand between my shoulder blades and the other on my hip and bent me over.
“Now here’s the second challenge. I want you to take a walk with me around the castle wall, all the while holding this inside you.”
I felt something very slippery and uncomfortably cold pushing its way into my anus.
“W-what’s that?”, I asked with my face still close to the ground and my butt in the air.
“A butt-plug of course silly”, she said and slapped my behind playfully.
“Oh, and I don’t think you’ll be needing your pants anymore.”

This was our third meeting. The first time we had passed each other on the steep street. She had smiled at me and I didn’t have time to respond before passing. The second time we sat on the same bus. I told her of the history of the town we were both staying in. Now I was sitting on the castle wall, looking at the lightning playing among the distant clouds and drinking a bottle of cheap wine. I felt a hand on my shoulder. I turned and saw her smile, bright and cheerful.
“hi, here you are again!” she said.
“hi. Climb up and join me?”
“Sure”.
She turned her back to the wall and jumped on, then turned again to face the sea. Behind us the ruins of the castle were quiet. The courtyards had long since turned into wild gardens and where medieval knights once fought only the occasional nocturnal adventurer from the town walked.
“So what are you doing up here?” she asked.
“Nothing special, just sitting. The storm is beautiful.”
Somewhere below a fisherman cast his line and the sound of his radio playing old Turkish ballads intermingled with the whispering of the waves.
We spoke a bit more. The usual traveler chit-chat. Where are you from? Where are you headed? How long on the road?
I’d been attracted to her from the first moment I saw her. It was hard not to be. Besides her perfect figure and classical facial features there was always that cheerful disposition with an undercurrent of naughtiness that I could never stop wondering about. From the way her hand brushed mine occasionally I guessed she at least didn’t object to my presence. Tonight she was wearing a short, black dress that set off her flawless body. Glistening black curls framed her face.
“I have a challenge for you”, she said, her smile turning distinctly mischievous.
“What kind?”
“Well, actually, it’s a series of three challenges. If you pass, I guarantee you the reward will be worth it. Think you’re up to it?” she said as she jumped off the wall. I followed her.
“What kind of challenges are we talking about here?”
“Well, now, that would be telling. Come on, it’ll be fun!”
I thought about it for a second. Normally I’m not much of a thrill seeker but after almost a whole bottle of wine it was easier to let curiosity get the better of me.
“Hmmm...OK. I'll try out your challenge.”
“Ready?”, she didn’t even wait for a reply, “Let’s start. First of all I’ll test your concentration. Remember when you were telling me about Ottoman history?”
I nodded, recalling our bus ride together. I was never quite sure if she had been interested in what I told her or just pretending to, but I couldn’t find a good subject for conversation so I told her about the sultans and warlords and long-dead knights who had warred over the town and fortress which were our temporary home.
“You never finished the story. So tell me the rest of it now and I’ll try to distract you. All you have to do is keep telling me the story”, her face turned mock serious. “But don’t fail because this is only the first challenge.”
I wondered what her plan was. I’m easily distracted even at the best of times, and now I was far from being clear headed. But the promise of a reward did seem tempting.
I started again where I left off on the bus. She looked straight into my eyes and I stuttered slightly but continued. After a few sentences I started getting into the rhythm of it, even enjoying myself. My usually reluctant tongue loosened and I let my voice convey what I knew of the past.
Abruptly my mind was thrown back to the present. I felt a cool hand slipping between my pants and the skin of my stomach, questing for my underpants’ band and then diving inside, cupping me.
“Don’t stop”, she said.