A Sissy's Date Night

I give James a moment. It doesn't ease the stiffness in his cock one bit. I guess maybe he likes having his balls in a vise.

"Jennifer," I saw in a very teasingly sweet voice, "do you know what I really hate about bipedal pigs?" I jerk a thumb in the direction of James so that he'll know I'm talking about him. "I especially can't stand the ones who think about their cock. You know the kind, the ones who get their pleasure, and don't worry one iota about the girl who was enough to join the swine?"

"Oh, yeah!" Jennifer replies with a faint giggle to her voice, "I know just the type..."

"This pig wouldn't be one of those pigs, would it?"

"Not usually..." Jennifer says. Then she pauses for a second and adds, "usually."

"Ah, so he's done it. That qualifies him as a pig in my book. I have a special circle of hell for pigs like that." I grin very widely and turn to Sophie. I tell her to "fetch the skankiest thing around."

She knows what I mean. Paige. Her "name" here is "skanky whore." Thus, she's obviously the skankiest thing around. Sophie heads behind the fabric screen that blocks off a corner of the room. That's where Paige is, locked up in her kennel, nude, and just waiting until I have some use for her body.

A minute later Sophie leads the naked Paige on a leash. Paige is eighteen. She's about average height, 5'4", and lean at 118 pounds. She has long, wavy, dark-blond/light-brown hair. And she has a pair of very perky 34-B breasts with wide light-pink nipples. She looks almost scrawny, but not quite. Not so thin that she doesn't have a very nice curve to her hips and waist. She's definitely pretty.

I doubt there's a 48-year-old man out there who wouldn't look at the naked body of an eighteen-year-old girl if given the chance. Even if his wife was standing there to see him gawking so openly at the youthful pertness of her body. If the guy were overweight, as James is, then ogling her body is as certain as death and taxes.

And that's exactly what James does. The second Paige is out from behind the screen, his eyes lock on her body. They roam, but only up and down her body, checking out everything from her lean legs, up to her shaven pubes, her slightly-point breasts, all the way to her bright smile. She sees him checking her body out and casually bats her eyes at him playfully. She doesn't dare do anything more without me telling her to. But parading her in front of James is enough for Paige to know I wish to flaunt her body for him. And with that sight, there no chance of his cock going soft anytime soon.

I just snap my fingers. "Skanky... show my guest what a couple of gutter whore you are. Play with that cock."

"Yes, my Queen, as you wish, my Queen," Paige says in a very sugary sweet voice. She turns to James and smiles a little wider at him. Then she takes a long moment to lick her lips slowly. She drops to her knees, sitting back on them. It puts James's cock right in front of her eyes, almost the same view James recently had of a cock.

Only I didn't tell Paige to suck it. I told her to play with it. It's one of the "commands" I've taught her. It means for her to do something very specific to his cock.

Paige plants a tiny kiss atop his cock. She does it with her lips opened slightly, sucking the very tip into her lips, and then flicking the tip of her tongue over it. It only lasts a second, but that's plenty for James to moans softly into his gag.

Jennifer watches intently, clearly wondering what I'm going to have this girl do to her husband. And if she wants Paige to do it or not.

Next Paige kisses her way down the side of his cock. She does it leisurely, taking her time and moving her lips only a tiny fraction of an inch with each kiss. She does it from the side, her lips closing around the top and bottom of his shaft while her tongue teases the flesh between her lips. She works her way all the way back to the very root of his shaft like that.

Her lips rise up off his cock. Her fingertips go to it. Paige has long, slender fingers, each topped with a well-manicured inch-long nail that's painted pastel pink. She takes her time with her fingers, too, casually stroking the tips of her fingers up and down the length of his cock.

It's enough already that it has James' cock twitching. Not that it can twitch that much. Just little jumps up and down.

After several slow strokes along his shaft, Paige wraps her fingers around it loosely. With her grip barely touching his skin, she takes three very slow strokes along his entire length. Even his very sensitive head passes through her delicate fingers.

And then, Paige kisses the very tip of the cock again, starting over from the beginning. A pattern she'll repeat endlessly.

It only takes a couple of minutes for James to be moaning rather sweetly, and urgently, into his gag. I see the shudders on his body, as he wants to squirm a little. Or really to do anything to intensify the sensations Paige is giving him. Like thrusting his hips. But he can't. Even the tiniest of motions is enough for his balls to really feel the crushing. He ends up standing very still with only the faintest of quivers sweeping his body. And moaning loudly.

A minute or so later I see the first droplet of his cum as it slowly weeps from the tip of his captive cock. Its stickiness clings to the tip of his head, making it glisten brightly. For a couple of seconds. When Paige kisses the tip of that cock, she also licks it away, leaving only an equally sparkly little bit of saliva on the tip of his shaft.

Paige keeps right on going. She ignores everything. Such as the increasingly pleading tone of James' moans. Or the hastening pace of those little droplets of cum seeping from the tip of his cock. She just goes on teasing his cock.

"Gawd," Jennifer finally says after about ten minutes of it. "That's almost cruel..." But Jennifer is smiling as she says it.

"Yeah, almost as cruel as taking advantage of a woman by getting his pleasure from her body, and ignoring her needs." I grin back. "Now he'll appreciate the importance of considering his partner's desires as well as that little dick's desires."

"How long are you going to leave him like that?"

"Oh, I don't know..." I sigh, but with a good note of taunting in my voice, "until I tire of watching him suffer..." I turn to James, "isn't just so awful when your sex partner thinks only of what she wants, not how badly that tiny dick wants to cum?"

James very eagerly nods yes.

"Ah... too bad I'm a selfish girl. Right now, I'm thinking of how entertaining this is to watch. Maybe eventually I'll think about how badly that dick aches... or maybe not."

The show goes on. The vise ensures that James does nothing but stand there, and stand very still, while Paige plays with his cock. Paige's teasing ensures that he never cums. He just stands there, feeling the sensations of her kissing and stroking his cock, but never gets quite enough to bring him to climax. I'm sure he's figured out by now that he won't be cumming like this. That he is truly at my mercy.

And the show goes on. Every minute that ticks by, it seems like James is suffering just a little more. He moans more pleadingly into his gag. He quivers just a little more. I think his toes even curl under his feet a little tighter. But that's all he can do. It's kind of hard to tell how fast the cum is weeping from the tip of his cock. Paige is keeping it well tongued-clean. And I know that the tender caress of Paige's soft tongue licking that little droplet away is doing one thing only: making him suffer that much more.

Finally, I take James's gag off. His moans are loud now, the gag no longer muting them, and they're begging-urgent. "Does my little sissy want to cum now?"

"YES!" James cries out urgently, "please Miss Rodgers, please let me cum now!"

I sigh... "Well... there's no way my skanky whore is going to do that! At least not for a fat slob with a tiny dick like you... Perhaps if you begged Mrs. Palmer she'd finish you off... or maybe not." I grin. Before James has a chance to beg his wife for release, I turn to Jennifer and tell her "I do have a very nice locking chastity tube you could borrow. It would ensure that he can't even masturbate no matter how hard he tries. Or you could finish it for him. I would care how, and I'm pretty sure he wouldn't either. Your hand would be fine by him. Or, if you're up for some additional entertainment, you have two choices. First, skanky there can go on endlessly. Or, there's that hole in the wall over there. He could finish himself in it." I point to the hole in the wall. It's right at cock height. "trust me, that's worth seeing."

"Mrs. Palmer!" James doesn't give me a chance to change my mind. He immediately starts begging Jennifer for relief. "Please, Mrs. Palmer, please. I am so sorry for taking you, and any woman, for granted! Please, I've learned my lesson, Ma'am. Please, will you please allow me to cum, Mrs. Palmer? I don't care how. ANYTHING, just end this agony. Please, Mrs. Palmer, I'll be your slave for life, just please allow me to cum!"

Jennifer looks at James for a long moment. Then she glances at the hole in the wall. She turns back to James and for a long second, she says nothing. Finally, she asks me, "is the hole really funny to watch?"

"Oh, yes!" I assure her.

"Well, I guess he can use the hole... I'm certainly not doing it for him."

"Your choice. Although it would have been really funny if you did. You know how men just can't help but thrust those hips while they do? Not with their balls in a vise! They make the most amusing squeals. Like little girls when they try!"

I have Sophie unlock his feet. Then, as I loosen the vise to free his balls, I have Sophie return Paige to her kennel.

As soon as James' balls are free of the vise, I grab hold of his hip and nudge him to come along. I walk him straight for the hole. And he comes very eagerly. So much so that I almost have to slow him down.

The hole in the wall is just that, A hole 2 ¼" across. It has 1/8th-inch thick latex flaps, like pussy lips, covering it so he can't see inside. Just past the drywall, there is a 2 ½" thick piece of PVC pipe that's glued to the drywall on both sides of the wall. Inside, it's filled with a soft, dense, squishy foam, almost like memory foam. In the center of the foam, there's a ¾" wide hole. Inside the closet on the other side of the wall, there's a pump that pushes a steady, slow, supply of an oily lubricating jelly into the pipe. That soaks the foam in it. The far wall, inside the closet, is also cut out even with the inside rim of the pipe. There's a 3"wide piece of pipe, only ½" long, glued to the wall. And over that little rim, there's a zip-lock baggie rubber-banded in place.

I have James spread his feet a couple of inches to get his cock lined up straight with the hole. Then I swat his bottom gently with my hand, urging him to move forward. He does, and his cock slips into the hole. I push his bottom forward until his pubes are flush with the drywall.

A standard wall is just under 4 ½" inches thick. That's the 3 ½" width of the stud, plus ½" of drywall on either side of the stud. Or slightly less, since in building supplies, measurements are never what they're advertised. But James has a little over 5 ½" inches of cock. Which leaves an inch, plus a few tiny fractions, sticking out beyond the wall.

To James, it feels like his cock is just sticking out beyond the wall. Into empty air. There's no way he can feel the baggie, or the pipe it's tied onto. It's almost exactly just the purplish head of his cock that sticks out into the baggie.

I put my hands on James' hips. Then I start letting him fuck the hole. My hands, the sharp ridges of my nails biting into his skin, hold him tightly and keep him fucking it slowly.

I motion to Sophie with my head. She gets my meaning. She goes to Jennifer and takes her into the small closet. And now that Jennifer is there, she can see the show. Or rather see James' cock head slowly emerging from the wall, then disappearing back into it, without ever knowing about the baggie that's covering wide around his head. His head steadily emerges and vanishes back into the wall.

"OH MY GAWD!" I hear Jennifer giggling. From the first stroke into the hole, James started moaning very sweet and urgent groans. Groans that make it clear he likes the hole. Jennifer peeks back out of the closet for a second, just to see that James is still so eager I'm having to hold him back so he doesn't finish immediately. I'd let him, but I want Jennifer to enjoy the show for a moment first. I call the view, the view Jennifer has now, a "womb's eye view" of a fucking. Because that's about what she's seeing. At least once she gets down and tries looking into the hole around his cock to see what's in there.

"Where did you get the idea for this?"

"A frat house, where else?" I laugh. "There was a pig there who told a slightly heavy girl that he'd rather fuck a hole in the wall than her. Unfortunately for him, he was just a pledge, and the president is a friend of mine. The short version, he got his wish. And I got an idea..."

It gets a hearty laugh from Jennifer. "I can just imagine all those horny frat boys with a hole in their wall... James, you were in a fraternity, weren't you?" She's grinning.

But it's all we have time for. James cries out long and loud. Jennifer turns her attention back to the head of his cock. She's just in time. She gets to see it spurt the first powerful stream of his cum. A stream that shoots several inches before hitting the baggie and starting to pool just as a second spurt shoots from his reemerging cock head.

It takes James almost a minute to fully cum. I keep him moving the entire time, holding his rhythm steady, his cock plunging in and out through the hole until there's no cum left in it.

Only then do I pull his still-hard cock from the hole. It shines with a thin coat of the oily lubricant. And it stands straight out. I unlock his hands, pulling them to the small of his back. I lightly swat his ample bottom with my crop and warn him to leave his hands where they are until Jennifer gives him permission to move them.

Then I poke my head into the closet. I pull the baggie off the pipe and seal it up with his cum inside of it. Then I hand it to Jennifer. She takes it, a smirk on her face, but she also holds it out away from her body. Before she can ask what she's supposed to do with that, I teasingly tell her "take your trash. I charge a disposal fee for HAZMAT." then after I giggle, I lower my voice and quietly suggest that she make him carry it back to their hotel. And if she's in a playful mood, she might taunt him about the taste of Rory's cum in his mouth. Something like asking him if he thinks Rory squirted as much into his mouth. Or if he wants to see if his tastes as good as Rory's does. It gets a grin from Jennifer.

We all return to the living room. There I have James kneel before Jennifer. And then he learns that his clothes are at Jennifer's mercy. She may give them back to him whenever she wishes. Or not. I send Sophie for a cup of coffee. I smile at Jennifer, and she catches the hint. She tells James to fetch her one, too. Why should "my sweet slave" have to wait on her when he's doing nothing? He goes, slightly unhappily, but quickly. And when he returns he serves her cup just as humbly as Sophie serves mine. He must really want his clothes back.

Jennifer tells him that she could get used to being served like this. He should take notes. She likes to feel special, and this makes her feel special. As in, you are so going to be serving me like this from now on!

After our coffee, Jennifer allows James to dress. As I suggested, she makes him carry his baggie of cum. And she makes him return to the hotel with his makeup on. I even let her take "Jessica's" dress with her. After all, she paid for it. Maybe she can return it. Or maybe she can use it to remind James of his place.

I figure that's the last I'll ever see of James. And the idea doesn't bother me. He's not my type. There's no place for him in my toy box. But then, about a week later, Jennifer calls me and tells me that James would like to return for another lesson. Apparently, he feels that he doesn't fully appreciate womanhood yet.

Jennifer adds, "He just liked it! And that is so weird!"