Date Night

I put two fingers to the top of his shaft, pressing on it lightly and feeling the tube inside. I can feel the blood starting to flow. I can feel how much it wants to stiffen up. I'm sure he's doing everything in his power to keep it soft. He won't last long. I run my gloved fingers lightly along its length. Then I get to the tip of it.

I give the spongy, soft head of his cock a little squish. That's the part of his cock that will never get rock hard. It's also the part with the most nerves in it. It's soft. I can feel the faint tremor sweep over his body as I play with the head of his cock. I keep it in my hand, lightly kneading the sponginess.

"When is the last time this penis ejaculated?" I ask him in a very detached and professional tone. It's my nurse's voice. I can guess that Jerry has always had some fantasy about a naughty nurse. Most guys have. I just haven't told him that I'm a nurse yet. But I am using proper terms, instead of more common terms, when I talk to him. Like I'd do if he were a patient. I'm not sure if he's picking up on that or not. But he will soon.

"I came when Mistress was here and allowed me to masturbate. That was last Saturday night, Miss Rodgers." Jerry tells me.

"Why don't I believe that? Oh, yeah, because you're such a naughty boy! Well, luckily for me, I happen to be a nurse. I think I'll just check this tiny penis for myself and see if it's been ejaculating or not. You wouldn't be lying to me, would you, fuck stick?"

"No, Ma'am!" Jerry says very firmly. It tells me that he hasn't cum since Saturday night. He's sure of that.

"Not even one tiny little drop?"

"No, Ma'am!" He again insists.

I hold my hand out to Sophie, palm up. "Slave, give me the urethral dilator." Then I look up at Jerry's face. It's already scrunching up, even as his eyes go wide in fear. The look on his face is half horror, half nervousness. As if he hasn't a clue what I'm going to do, but doubts that it's going to be fun.

Sophie puts it in my hand. I can see Jerry's eyes staring at the hideous-looking implement with erupting fear. It's an actual medical instrument. But it looks like something invented by the Spanish Inquisition for persuading the more adamant heretics to repent. It's surgical steel and shines brightly. It has two blades, about six inches long, but narrow at just under ¼". The blades are curved slightly, leaving only their edges touching as they wait, now closed. It has a handle on it like a sprayer would, two grips that are meant to be squeezed together. Now its blades are closed, making them into a small metal tube a little narrower than a pencil. The very tips of those blades glisten brightly with the tiny dollop of lubricant that Sophie put on them for me.

I can see the tremors flowing over Jerry's body grow stronger as he imagines what I might do with that tool. I'm sure he's praying it's not going to live up to its name.

I wrap my hand around his cock, getting a snug grip on it just behind the head. I hold his semi-soft cock firmly, pulling it out a little away from his pubes to stretch his shaft straight.

And then I put the tips of its blades to the small opening at the very tip of his cock. They're just barely larger than the hole is. But the head of his cock, and his urethra, are rubber and easily stretched. I just wiggle the tip of it slightly, and that works it into the hole. It barely has to stretch him at all.

Jerry stares down at his cock, seeing the shiny steel tool ready to push into his shaft. His face looks like he's about to cry from just the thought of it.

I push. The blades slide rather easily into his cock. But there's nothing there to resist them. Just the rubbery soft tube they're sliding into.

"OW!" Jerry screeches out. His voice has been moderately on the deep side. Rather manly. But now it's high-pitched and very girly. And it rings of pure panic. Well, with some discomfort laced in. I know it hurt, but just a little. It's no worse than a needle stick. But there's the panic factor. Jerry's watching the pencil-thick shaft pushed a good six inches into his cock. That, the mere idea of it, is unbearable for guys. Far worse than the actual discomfort of it.

I push all of those blades into his cock. The instant they start pushing in, and Jerry screeches, I feel his cock swelling in my hand. It's not a slow stiffening. It's like an explosive stiffening. As if it's jumping to full hardness in an instant. And it does. It's as hard as steel by the time I have the blade inserted, and that's about one second.

It doesn't make a difference if his cock is soft or hard for me. Or for him. The thick tube that actually gets hard doesn't surround his urethra. It leaves the rubbery tube to run along the underside of his shaft.

"I didn't say you could whine like a little girl, fuck stick. Now shut up and behave while I see for myself how naughty you've been. Unless you'd prefer that I spank you and then we can try this again."

"I'm sorry, Ma'am!" Jerry urgently pleads. "I'll behave!" I can hear the panic in his voice as if doing this again is the very last thing that he wants. That alone makes me think I should do it again!

"How can you say that? You're being naughty! I didn't give you permission to have an erection, did I? You're not having sex. You're getting your penis checked by a nurse!" I use a rather mocking and disapproving voice.

"I'm sorry, Ma'am! I'm trying!"

"Oh, well. It's your penis I'm going to dilate. I don't care if it's soft and stretchy or hard. I won't feel it!" I giggle. And then I squeeze the handles. The blades start spreading apart.

"EEEE!" Jerry screeches. It doesn't hurt. He can feel his tube being stretched, but that's it. It's no different than stretching his mouth wide open. The unpleasant part is putting the dilator in. And taking it out. But that doesn't make him any less nervous about it. I don't think my words helped him any, either. My bad... NOT.

I stretch him wide maybe close to a full centimeter, which is a good bit. Especially for the urethra. Then I let the handles lock in place, holding the blades apart.

Jerry stands quivering, his eyes locked on his cock. His face is nervous. I just calmly ask Sophie to hand me a penlight. Then I squat down, holding his cock in front of my eyes. The steel blades ensure his cock stays straight. Not that they have to, it's stiff enough on its own. And that tells me more about him. He is liking this, and the little bit of pain is turning him on, not off.

I shine the light straight into his cock, between the steel blades. There's really not that much to see. Inside, it's just pink. The soft, loose walls of his tube stretched wide open, letting me see all the way to the muscle of his bladder. The nerves lining that tube, and the tiny little strands of fur inside it, are far too small to be seen. It looks like a pink tunnel with soft walls.

But I can see a few tiny drops of cum deep inside his tube. Almost all the way back. It's right where his prostate surrounds his urethra. Right, where his body makes that creamy cum. I knew I would find a few little specks of it. I would be concerned if I didn't. They're always there, at least in a healthy man.

None of which means I won't use them to humiliate Jerry. I never claimed to be fair! "You filthy... boy! You lied to me! I can see the semen in your penis, care to tell me how that got there if you weren't ejaculating? Don't bother, I'm a nurse. I know that's the only way they get there!" I sigh heavily.

"Slave, my camera," I say with an exasperated voice. Sophie quickly hands me my phone, the camera app already open. And the flash turned on. She has it set for an extreme close-up, too. She knows what I want. I point the lens down the length of his tube, tilting it slightly until I can see those whitish little droplets on the screen. I take a picture. I hand the camera back to Sophie.

"Send that to his Mistress. It's proof of fuck stick's disobedience." Sophie sends it.

I need one hand to hold the handle of the spreader. But I don't need to hold his hard cock. The steel blades will keep that from moving. I put my free hand to his balls, gently cupping them. I give them a few little squeezes, more teasing him than anything. But it is enough for me to feel how firm those orbs are. And how big. I tease them for about half of minute before releasing them.

I hold my free hand out to Sophie, telling her to put a drop of lubricant on my finger. She does. It's a stingy drop. I guess Sophie doesn't feel that Jerry deserves anything more than the bare minimum for his comfort. Then again, Sophie strongly disapproves of disobedient slaves.

I hold my glistening finger, letting Jerry see it. "Now stand really still while I check that naughty prostate!" I tell him. I tell him in the most enthusiastic, and taunting, voice that I can manage.

Standing straight up is not the easiest position for me to get to his asshole. It's even harder for me like this. I have to stay in front of him. I'm still holding his cock stretched wide open. I'm already squatting down, so I reach up under his balls to get my finger to his bottom. I push my finger between the bottom edges of his firm cheeks, feeling the inside edges against my finger as it stretches his crack slightly.

And then I feel the tight ring of his asshole under the tip of my finger. His is tight, and it's cinched to its full tightness now. His feels slightly bigger than Claire's did. I would guess that his entire asshole, the ring of muscle, wouldn't be any wider than a penny. So it's not too big. But I can feel his funneling inward moderately. More so than Claire's. And, as the tip of my finger first touches it, I can feel that its opening isn't perfectly round, but will look more like a tiny line. But as my finger presses against his ring, it shifts into roundness quickly. Almost before I feel the rubbery firmness of his muscle against my finger.

I stop. I hold my finger just like that. I move my head aside so that I'm not looking down his cock. I tell Sophie to get my camera again, and I wait as she does. I don't have a third hand, as much as I wish I did. So I have Sophie kneel down and aim the camera, now set for video, down his cock.

Now I push gently with my finger, feeling the firmness of his ring. For an instant, it tries to resist. Then it quickly softens and allows my finger to begin easing into his bottom. Penetrating him this way, it's not long before the tip of my finger feels the walls of his rectum. His asshole is snug, but it's around my finger between the first and second knuckles. That's because he's standing, not bent over. This way, there's a little bend at the bottom of his rectum. It helps him to control his bowels.

Luckily the rectum is rather rubbery, loose, and soft. It feels like poking against a loose rubber band. One that pulled only taut enough that it's not sagging. I use my finger to push down, the pad of my finger pressing straight towards his balls. Just not quite deep enough to be above his balls.

I can feel the hard shaft of his cock, right where it's anchored to his body. That swollen stiffness is unmistakable. And, with a faint pressure, I can feel the hard gland of his prostate just behind the hardness.

I start stroking my finger very lightly over the top of his gland. "Hmm... this prostate is rather hard..." I pronounce in my clinical voice.

It doesn't take Jerry long at all. In about three seconds I can hear his breathing deepening. And picking up its pace. I can hear a faint moaning creeping into those breaths, too. And then I notice the quivering. He's been quivering since I first took hold of his cock. But now those quivers are steadily crispening up. They're turning more into needy shivers. Or a hungry trembling. His purring breaths grow louder, too.

I keep going, massaging his prostate for close to half of a minute. It's simple biology. The prostate surrounds his urethra just behind the hard shaft of his cock. The very same nerves that run along his cock run through, or at least over, his prostate. My finger is stroking those nerves just as effectively as if I were stroking the shaft of his cock. Except that I'm not touching his cock. I guess technically I'm only touching his rectum. It's actually the backside of his rectum that's stroking his prostate.

I take my finger out of his asshole. Jerry grunts lightly as I pull it free. Then he sighs with equal parts relief and frustration. After a week without an orgasm, I have no doubt he's ready for one. And I have no doubt that I was pushing him right towards it. I could already feel a few little twitches starting in his cock.

Then I take my light and look right down his cock again. I have no doubt what I'm going to see. I know what I was doing to him. And I know how his body would react to it. Just as I expect, I can see several larger and fresh drops of his cum welling up in the base of his cock. I know Sophie has a nice video of them slowly oozing into his tube, too. I'll use that to degrade him later.

"You pervert!" I scold him with as much disgust as I can muster in my voice. "Here I am, nice enough to give you a complimentary prostate exam, and what are you doing? You're cumming! I didn't even give you permission for an erection, let alone to cum! Now I have to wash your filthy cum off my dilator! You are in so much trouble, fuck stick!"

"I'm sorry, Miss Rodgers!" Jerry very pleadingly blurts out, his voice almost desperate.

"On that, we agree. You are sorry. You're a sorry excuse for a fuck stick! Clearly, you can't be trusted not to cum all over me while you get your spanking for cumming during your prostate exam." I sigh, quickly. "Slave, give me a cock stopper."

"OH YES, Mistress!" Sophie giggles. Her voice sounds very excited, too. As if she thinks cock stoppers should be standard equipment on males.

She puts one in my hand. These are something I made up. They're disposable, too. They're made of tiny little rubber stoppers, like corks. Each one has a hole drilled through it, and a little plastic stick in it. The stoppers I bought online, they're for narrow test tubes. The sticks are just coffee stirrers they sell at Wal-Mart for like a buck. The sticks are glued firmly into those holes. Shaped just like a cork, one end of the stopper is slightly narrower than the other. The stick extends from the wider end.

Sophie didn't bother with any lubricant on it. There's no reason for it, not with his cock already stretched wide open. I just put the stopper between the blades of the spreader and push. Jerry groans a little, feeling the stopper scraping along the inside of his tube at the top and bottom where his tube is stretched between the blades. I push it all the way past the blades, stopping it just before his prostate. Just before where those little droplets are starting to well up.

Then I close the spreader and pull the blades out of his cock. Jerry screeches like a girl again. But it's over in less than a second. It lets his tube close back up fully. Except now there is a black plastic straw sticking right out from the tip of his very hard, lightly twitching, cock. It sticks out about two inches. And on its end, there's a bright, neon pink, little flag dangling. That's just a ¼" wide strip of ribbon. It has "Remove Before Orgasm" printed on it. Just like the orange flags on the pitot covers of airplanes that say "remove before flight." those were my inspiration for this pink flag.

With the stopper inserted and still, Jerry barely feels it all. It doesn't hurt. It's not even uncomfortable. It's just enough for him to know it's there. I'm sure he's wondering what it's going to be like with the stopper inside his cock. And imagining that it's going to hurt coming out. Which it will. I didn't design it with his comfort in mind. More the opposite.

I stand back up. I still have to look up to look him in the eyes. But it lets me see that Jerry is lost. That this is nothing like Colette has done with him before. That he doesn't know what's coming. And that's making it hard for him to behave. He's too antsy. And judging by the twitching stiffness of his cock, too excited now. It's one of the reasons why we swap toys once in a while. It gives the toy a little variety. Like now, where for Jerry this might as well be his first time again.

"You will be paddled five strokes for cumming without my permission. You will be a very good little boy for your spanking. Now, go fetch me a chair, and don't waste any more of my time, fuck stick. Ten!" I start counting.

"Yes, Miss Rodgers!" Jerry blurts out very quickly. He takes one very tentative and cautious step. I'm sure that's because he's never had anything sticking out of his cock before, and doesn't know what it's going to be like to move with it there. He discovers that he doesn't feel it any differently. Not even with his cock bouncing around as he moves. Then he almost starts running to go fetch the chair.

I can see it on his face. A spanking is nothing new for him. He doesn't mind that. Nor is the paddle going to be new for him. Colette has worn more than one paddle out in these last years. I'm sure some of that wear came from Jerry's bottom. But going over the knees of a very young, and very petite woman will be especially humiliating for him. Like a child spanking the parent would be. And I know he's wondering what that stick in cock is going to do for him.

He brings me the chair. I've only counted down to four. He sets the chair out for me. Then he waits, patiently, as I slowly take my seat. And open my knees, giving him a lap to lie over. He might have wondered how he'd be paddled. If I would have him bend over the chair or something. I'm sure some part of him wonders how such a small girl is going to turn a big man over her knees.

I reach out and grab hold of his balls. I squish lightly, just firm enough for him to feel me gripping them and know they're mine now. I tell him to come around to my side. I don't wait for him to move. I use his balls for a leash and guide him around to where I want him. Like any man, he quickly follows his balls without hesitation. I tell him to get down to his knees and use his balls to pull him down.

Jerry is very quickly on his knees at my side. No way is he going to risk me pulling down any harder on his balls. He almost drops to those knees.

I grab hold of the back of his neck. I'd prefer his hair, but his hair isn't long enough to use for a leash. I pull him forward, bringing his shoulders down as he leans over my thighs. He's tall enough that even on his knees, as I bring him forward, his cock lies on the top of my thigh. I pull him forward until my thigh is flush and snug against the bend of his waist. Then I push him down, spreading my thigh until it's about under his nipples. It leaves his knees brushing on the floor. Touching it, but not on it enough to support his weight. And it leaves his hands on the floor in front of him. But it has his weight on my thighs. I don't mind. The chair is doing all the work. It's under my thighs. I can just feel his weight squishing down on them.

I have Sophie hand me the paddle I've brought. I don't like to carry too many of them around with me, so I picked my favorite one. Even though it's black! It's made of two pieces of hard leather, with a very thin sheet of spring steel between them. The flexible metal just makes sure it holds its shape. Almost as if it were wooden. It's about 18" long and about 4" wide, but only about ¼" thick. Not counting the wooden handle.

I lie the firm leather against Jerry's equally firm globes. Thankfully there's only a light coat of hair on them. Enough to make them look manly without making them look simian. "This is for cumming without permission," I tell him exactly why he's being spanked.

Then I raise the paddle up high. And I put almost all of my strength into it as I swing it downward. It's a little more than I usually put into it, but not that much more. Unauthorized orgasms are a very bad sin. They deserve a harsh punishment. I snap the paddle down hard, landing it squarely atop the fronts of his cheeks.