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Managing Expectations

We stand next to each other in the hallway of the apartment I found on AirBnB. Water dripping from our clothes. Your hair a wet tangled mess. Drops of water dripping down your face. I can see your nipples, hardened from the cold, poke through wet layers of clothing. I want too warm them, caress them, bite them. We have talked about such acts over the phone and in texts for months.

It's strange, this build up, all the anticipation and the shared fantasies finally meeting reality. There haven't been many limits to the stuff we shared, our cyber relationship is well beyond the point of self-consciousness, hesitation and insecurities.

I've seen every wrinkle and mole on your body. I've seen you use all sorts of things to excite yourself and get yourself off. I've been invited to see you at your most vulnerable, your eyes staring vacantly into the camera lens, your body slack after an orgasm.

And in turn I've shared myself with you - you've seen and you've heard, and if my sperm could have traveled the internet you would have tasted me as well.

But still, I am standing here glancing at your stiff nipples through your clothing, with a feeling that I am invading your privacy. And I wonder, as I've been doing for hours, how to cross that line. What is the magic word or action that can transform us from amicable strangers hanging out for the first time to that coupling couple that we've already been for months in our fantasies.

I arrived to JFK earlier in the week, on assignment to a New York client. Two days of hard and rewarding work later, I texted you. Done with the assignment I had an afternoon and a night in NYC on my hands. We hadn't made any plans. I'd told you of the possibility of a meet-up. But my work being notoriously unpredictable, I wasn't in any position to make a solid date. Being the accommodating and agreeable cyber girlfriend, you had accepted this and told me you would be on standby if I could make time.

My text read: "Meet me in Battery Park 1pm, don't be late, no panties."

I had been thinking about that no panty rule ever since. Right this minute, I was fixated on it. My gaze moving down from your breasts to your hips. You simultaneously turning to check your soaked features in a mirror, thereby giving me a nice view of your wet skirt clinging to your shapely tush. It would be so easy to slide my hand under the skirt and in between your thighs, finding my way to your smoothly shaven lips and the little tuft of hair above them.

I didn't need to see them. I had seen them up close. I'd seen them glistening from your wetness, puffy from your excitement, stretched out around bulging objects I'd asked you to use as substitute for my cock... But I needed to feel them. Sliding under my fingers. I needed to taste them. Sticking my wet fingers in my mouth. I needed to play with them. Pulling hard on that tuft of hair.

If I could only find a way for us to transit from clothed near-strangers to nude lovers in the real world, not only in our shared fantasies.


I was sitting on one of the benches looking out over the Hudson, having a coffee and a smoke as I waited for you. Staring out at Ellis Island, I thought about my grandfather arriving here in the 20's. The sun was still shining, reflections glittering in the waves, but dark clouds were moving in from the Atlantic. I didn't need to check my phone to know the time. The seconds were beating with my pulse. A countdown running. I had been trying to decide earlier what I would prefer. You being on time or you giving me the opportunity to punish you by being late. (A thought that made way for all sorts of enticing imaginations, you tied up on the poster bed in the apartment I was renting, me searching around for some practical utensil to use on your posterior.)

Half a minute before one o'clock, I let my gaze leave the river and the cloudy horizon and scanned the promenade. I immediately caught sight of you, walking quickly, meandering through the crowd on the walkway. I could see that you had been in a hurry getting ready. Your light summer clothing not really the best choice, considering the storm warnings on the weather channel I had seen earlier.

I savored the chance to look at you without you knowing. Heels clattering on the walkway, ankle socks and your legs bare, your knee length skirt moving with the sea breeze. Up top a white, slightly gauzy blouse and a short smart dress jacket made me wonder about your underwear choice. Probably a white or at least light bra, since anything colourful would shine right through that blouse. Sunglasses and the hair gathered in with a wide ribbon, wide enough to use as a blindfold if the need arose. A rather small shoulder bag for a possible overnight stay completed the ensemble.

To sum up my impression in the seconds before you caught sight of me: No panty rule might be adhered to. Skirt a good sign in that case. Clearly a rushed departure managing to find a sitter and getting here on time, through cutting corners. Possibly no make-up, sunglasses covering the eyes. Almost no luggage, maybe indicating you were only expecting a couple of hours of touring the city?

In short, over-analyzing the complex reality of this meeting, I had already decided to doubt instead of taking charge.


Half an hour later we were sitting in a diner having lunch, totally engrossed in a conversation comparing the worldview and treatment of the human condition in cinematic and novelized SF.

Which made the visit to a large bookstore on Prince Street, browsing the bookshelves and having a cup of coffee, a logical next stop. (In a bookstore there are plenty of opportunities for close contact, peering over your shoulder, standing really close, wondering if you are as horny as I am.)

Later in the afternoon, we stood hand in hand at MoMA, laughing at a totally outrageous temporary exhibit. The hand holding felt like a huge step at the time - braving the possibility of a snub, catching your hand while walking into the museum. (All the while thinking of that soft grip, caressing me, those fingers pinching me, those nails scratching me.)

Next up, we were visiting the Apple store on Fifth Avenue, because that's what you do as a visitor from Europe if you happen to be partaking in the cult of Apple, right? (Associating Apple with my iPhone, starts me thinking about all the nude art you've made and sent me, glancing sideways at your now open jacket, the sheer blouse and the white bra strap showing at your shoulder. Wanting to rip it all off and get my hands on your nude body finally.)

The storm, totally forgotten, struck with excellent timing. Torrential rain pouring on top of us as we walked in Central Park. At first we were just happily laughing at nature. Getting soaked can be fun if you're in the right mood. And also, with the weather warnings, and the dark gathering clouds, fits of giggles arose from the fact that we were both totally unprepared. No umbrella, not even a decent jacket. (The sheer blouse, slowly becoming a see through blouse. The white bra shining through like a beacon. My mouth watering from the need to bite down on your breasts, to lick and suck those nipples.)


Off and on during the enjoyable afternoon, I had contemplated ways to invite you back to my AirBnB apartment on the Upper West Side. With you not bringing an overnight bag it felt presumptuous to assume you were spending the night. You hadn't told me anything of your arrangements with the kids. I realize now I was overthinking this, but at the time I didn't get what really ought to have been evident.

The rain. The giggles. The apartment only a few blocks away. I know an opening when I see one. I managed to stop giggling long enough to squeak out, "Hey, actually my apartment is only a few streets over. How about getting out of this rain?"

And we ran. Leaving the park and finding our way a few streets uptown, arriving at the building. Out of breath from running we spent the elevator ride in silence, catching our breath. And seconds later we were standing there in the hallway. Your eyes wide taking in the view of Central Park and the designer furniture in the living room. The coolest thing with AirBnB is that for a couple of days you can afford to live like a millionaire.

And moments later, me checking out your backside while you are busy in front of the mirror running your fingers through your wet hair, trying to get the wild curls into some sort of order. I realize, this is it, that fate has given me the opening I couldn't make for myself. We're alone finally. And we need to get out of our wet clothes. Not only from the deep seated need to have you nude in my arms finally, but for the very practical reason that we need to get dry, and warm.

I catch your eye in the mirror and start undressing, shrugging my soaked jacket off and slowly unbuttoning my shirt as I command you, "Strip!" I do not even stop to check that you obey.

I walk into the bathroom, shedding my shirt and start the bath water running - hot and steamy. I slide my jeans and boxers down, leaving them in a wet pile on the floor as you slowly enter the bathroom. Upper body nude, eyes downcast, you start to wiggle out of your wet skirt. I stare at your lower abdomen as you reveal your pantyless state to me.

Your eyes are fixated on my dick. Licking your lips. I can feel myself harden. I know you only have one thought in your mind right now. To try to swallow my slowly hardening cock whole. I am not having any of that. Not yet, you have to earn it. You have to be disciplined for your total lack of initiative these last few hours. But first you need to get warm.

"Get in the bath!"

Blissfully I lose myself in your body. Warm soapy water helping my fingers explore all the things that have been eyes-only until now. I caress lightly, I knead, I pinch and I scratch from your toes to the top of your head. All the time keeping my hands off the places you want me to touch most. I tug at the hair you've saved for me in your armpits, soaping them up, rinsing them off. I pinch the underside of your breast avoiding contact with the nipples that seem to scream for my attention in their erect state. I massage the insides of your thighs, my fingers so close to your cunt that I can feel the heat it is emanating.

When I've satisfied my need to touch you, I decide it is your turn.

"I want you to cleanse me in return. I want you prostrate, kneeling in front of me. I'll allow you to touch any part of my body that pleases you ... except my cock."

I can see the disappointment in your eyes as you soap up your hands. I close my eyes and lean into your touch, relishing in it.

When you're done rinsing the soap off my body, I grab a towel and walk out into the apartment, putting on some music. I grab two glasses of water in the kitchen and we meet up in the living room. I hand you the water and ask you why you've wrapped yourself in the towel. Seeing my disappointment you let it slide off of you before taking a long drink. You smile and ask me if this is better. Instead of giving you an answer I walk over and sit down on the sofa, all the while watching you intently.

You're just standing there in the middle of the floor, gloriously nude, and a bit hesitant. You're trying to guess what I expect from you and I am happy to keep you guessing. I drink my water slowly all the while looking at you, cherishing the calm anticipation of what is to come.

"I expected more of you", I tell you. "I expected you to manage our expectations of this meeting better. We've spent hours together. I am well-mannered, but my patience is not unlimited. Where I come from it is up to the female to make it clear that sex is in the works. I've been waiting... but now I ask bluntly. Do you wanna fuck?"

"Yes, of course!"

"It's yes sir."

"Yes, sir, of course I want to fuck you."

"Since when?"

"Since the moment I laid eyes on you, sir."

"So why haven´t you told me or shown me of this sexual interest?"

"I didn't want to come off as slutty."

"Slutty, sir!"

"I didn't want to come of as slutty, sir."

"But you are a slut, right?"

"Yes sir! I am a slut."

"In what way? Tell me."

"Sir, I came wearing no panties, and all afternoon, especially when you've come close I've been so horny, creaming myself, trying to stay concentrated on our conversation, but all the while feeling my thighs get wetter, all the while thinking about your cock, and if you would let me play with it."

"And do you think I will let you?"

"I hoped sir, but now I am resigning myself to the fact that I made you disappointed in me. Please let me make it up to you, sir."

"We'll see, little one. But first we need to take care of your discipline. Let's see: One, hiding your sluttishness. Two, wrapping your nudity in a towel. Three, forgetting to address me correctly - twice..."


"Did I address you? Ask you anything? Give you leave to speak?"

"No sir."

"So shut up and let me think!"


"Here's the deal. Search the apartment. Find something for me to tie you up with and something I can use for disciplining you. Make sure it is something that appropriate for your misdemeanor, or I will get my belt instead. You've got five minutes until I want you on the bed, ready to be punished."

While you bustle around to finish your assignment I find myself another glass of water. Sipping it I exchange the low key music too something with a bit more energy. I visit the bathroom, taking a leak. Watching myself in the mirror I wonder what part is me and what part is a role I am playing. What do I do out of my own urges and needs, and what do I do to play out a fantasy I know you've been feeding for months? The man looking back from the mirror has no answer, but I decide that I need to go see what I can find out about myself in that poster bed where you are waiting.

When I enter the bedroom I find you stretched out on your back, a pile of ties and my leather belt beside you on the bed. I consider turning you over on your stomach to focus on your beautiful backside, but decide against it. If you've chosen this side, you've chosen this side. I slowly tie you up, until your hands and feet are bound to the bedposts with the ties you collected. Tied up, spreadeagled. Your eyes follow me as I leave the room to go through your shoulder bag. I delight in finding exactly what I need in there. Nipple clamps, your broad hair ribbon and lube.

"You really are a slut," I tell you as I return. "Look what I found in your bag."

I blindfold you with the ribbon. Put the lube on the nightstand. And try to decide between the clamps and the belt. The belt it is. I climb up on the bed, the belt folded in my hand and start gently slapping your stomach with it. Slow leisurely pats turning into harder slaps. I listen to the sound of the belt meeting your skin, and in between the strokes, your quick light breathing.

I let up to see your reaction. And smile when I see you squirm for more.

"What do you need, slut?"

"I need to be punished for not managing your expectations, sir."

Crack, the first hard slap from the belt lands on your right breast, closely missing the nipple. Crack, the second lands on your other breast and is almost drowned out by your high pitched moaning. Crack, crack, crack ... the following slaps lands on your stomach and your thighs, leaving red bands that slowly fade.

"That's five."

Holding the belt in my right hand, my left hand is free to caress the red marks I've made. Following your thigh I gently cup your pubis, your small tuft of hair tickling my hand, my fingers exploring your dripping folds. You're slick, open and when my fingers find their way to your clit I can hear a low sigh and feel a shudder pass through your entire body.

Crack, crack, crack... Three hard strikes from the belt in quick succession on the inside of your thigh makes you squirm again. But the ties do not give you much leeway. Three slaps in much the same place leaves a bright red mark. I push my fingers deep inside you while you squirm, one, two, three times. My wrist putting pressure on your clit. The quivering is a tell. You're on the threshold. A flick of my wrist and I can make you come. It's a powerful feeling. But I am not done.

I move the left hand out of the way and aim very carefully. The belt moving in a controlled trajectory and landing with a light smack right on top of your wet and puffy folds. The sound you make is somewhere between a sigh, a scream, and a groan. I strike again, hitting the same spot slightly harder. This time I can hear a distinct splash from all the wetness gathered in your folds right before your anguished sob. I look at your face and can see tears slipping out from under the blindfold.

"That's ten!" I say with some finality. "Do you think you can remember how to be a good slut now?"

"I think so, sir?"

"Think, huh, you only think... I guess that means you need a little bit more discipline before I can trust you with my cock."

I let go of the belt and pick up the nipple clamps. I remain still and silent while trying to figure out how to work them. I listen to your breathing slowly go back to normal. I can see your tensed up body relaxing. I let you wait and wonder in silence a while before I open the cap on the lube and start dripping it on your areolas. I use my thumbs to massage them, spreading the lube, caressing your nipples. Watching them harden and stand out even more. I attach the clamps and slowly tighten them on your nipples watching your face for signs of pain. You bite your lip, as your breathing becomes shallow and quick again.

I sit back, taking in the scene. The red bands on your thighs and stomach. The puddle on the comforter between your spread out thighs. Your breasts and the nipple clamps shuddering with every breath you take. The ribbon blindfolding you now slightly damp from tears. You shudder, and I guess it is from anticipation of what will come next. I am confident it is from pleasure, trusting my own judgement, but also aware of the fact that you've not even been close to uttering your safeword.

I get up and leave the room. I need to control myself. My cock is surprisingly hard and I long to just thrust it into your mouth, your cunt, your ass to quickly find my release. But that's not how I want this to play out. I want you to beg for it. I want to withhold it from you. And I know you're stubborn, a tough cookie to crack.

I busy myself with making coffee while my hardon subsides. Still horny but under control I walk to the window sipping my coffee. I look down on the traffic on Central Park West, savouring the moment, the anticipation. When the coffee is gone I go to the bathroom, rummaging through my toilet bag for the condoms I bought earlier anticipating this need.


I find you in much the same state as I left you when I return to the bedroom. Shallow quick breathing, squirming, trying to get purchase to rub your thighs together and failing. The knots on the ties have hardened from your jerking. I decide they have to go and that I can't be bothered loosening the knots. While fetching a pair of scissors in the kitchen, I find a couple of small metallic weights; just ornaments really, but I think I know a use for them. Back at the bed I attach the weights to the nipple clamps and quickly cut away the ties.

"Turn around, it is time for your backside to get some attention," I order you, picking up the belt from where I left it earlier. You roll over on your stomach, carefully not to upset the arrangement of clamps and weights on your nipples.

"Hands and knees, butt in the air, slut! I've been wanting to take a closer look at that piece of glorious ass for ages."

You quickly acquiesce to my wishes getting up on all fours. I watch the pendulum movement of the weights hanging from your nipples. You groan supposedly from the pain. But I can see you are moving your shoulders and torso to keep the movement going, relishing that pain. I stop in my tracks. Taking a moment to reflect on the weirdness of the human nervous system, of the wiring of our pleasure and pain centers, of the human condition.
"So, I've measured up your need for discipline while I was having coffee. We're ten strokes short. I also realized you do not know what is best for you, so I took it upon myself to decide that it is your backside that needs my attention. However, I'll let the slut decide one thing for herself. Do you want me to start on the left or the right buttock, slut?"

"Sir, just do it already. Please."

Seeing you are too overwhelmed from the sensations in your nipples to make any kind of decision, I just go with it. Hitting a lot harder now, since the backside can take a lot more punishment than breasts and thighs. Crack, crack, crack, crack, CRACK. Five lashes with the belt on the left buttock, the fifth one maybe too hard even. I have a hard time following your reaction. Your face hidden from view. Your breathing and other sounds drowned out by my own harsh breathing. I realize that I am at the verge of what I can put myself through. You can take much more pain than I can take to dole out. The realization comes with mixed feelings. Relief that I am not a monster and sadness that I might not be enough of a beast to satisfy you.

I take charge of myself, realizing I need to finish this. The five final cracks echo in the room. And I am done. I breathe through my nose eyes closed. Listening to your whimpering into the cushions. My cock is hard again. It amazes me that disgust and excitement can reside in the same moment in time.

You're still on all fours, reddened backside up in the air. Sitting on the bed behind you I examine the area between your legs closely. If possible, you're even wetter than before. I push three of my fingers into your opening with a squelching sound. Your clitoris is an angry, red protruding knob. I can't resist spreading some of your juices over it and you shake from the touch. Following your folds upwards my fingers rest on your back opening. The muscle is quivering. We've been talking about this. I know you are afraid of my size. I know you've had both good and bad experiences with anal.

I realize that there is a difference between theory and practice. That in theory this is something we should talk about, build up to, build trust, use massive amounts of lube, spend time preparing and relaxing... There have been books or at least treaties written on this. But that's theory. In practice we come to a point when we just take command of the situation or go with the flow. Sometimes a bit of both.

While thinking this I've kept the pressure of my fingers, slick from your juices, on your quivering muscle, massaging it slowly. Without my intent they slip inside one after the other. Your whimper is irresistible. I push my fingers deeper listening to your throaty groans. I let up listening to you sucking in air. You are so ready to be taken.

Quickly before I can change my mind, quickly before you second guess yourself and stop being this compliant, I grab a condom. I get it out of its wrapper and onto my erect cock in record time. I kneel behind you and slide my dick in between your thighs, soaking the outside of the condom with the juices running through your folds. The head of my cock brushes against your clit and you sigh, quivering. I wonder if you have any idea what is going to happen next.

Then I move my cock up to your waiting back opening and push it in slowly. Your high-pitched whimper makes me stop with only the head inside. We're both perfectly still in a perfect movement. I can't remember if I've ever been this excited before. Your muscles grabbing onto my cock as if their life depended on it. I put my hands on your hips, a strong firm grip, to keep you in place, and I push.

All the way inside you...

I'd heard moans, groans, whimpers, whines and sighs from you. The scream that you exhale now is best described as a wail. If it weren't for the fact that I can feel the contractions of your orgasm both with my hands on your hips, with my hips resting on your buttocks and squeezing my cock inside you, I would have taken it for an anguished wail. Obviously it wasn't, at least not all together.

Riding your orgasm and extending it I start moving inside you. As I gather momentum, and as your hips start moving, cramming my dick into you, I reach my own climax. It hits me like a freight train.


When I come to I have no idea how much time has passed. A second, a minute, an hour... I am prone on my side with your bum nestled into me. My cock has abandoned you, flaccidly resting on my thigh. I am holding you, breathing in your warmth and your perfect smell. I hear tinkling and rustling movements as you get rid of the weights and the clamps. I wonder if this is when we blissfully fall asleep together.

Suddenly you turn around, look me in the eye, and say, "That was amazing. But I think it's my turn now. Do you have any more ties lying around? I am going to get that cock of yours inside my mouth even if it means I have to tie you down."

expectations   managing  

Jan 7, 2018 in anal