A Sissy's Date Night

Rory brings James home about five minutes before "curfew." It makes me smile as I think about how many boys brought me home about five minutes to curfew when I was still a teenager! It was a sure sign that the date had gone decently well. Otherwise, I'd have walked away long ago. It makes me think that Rory enjoyed his date with James, at least a little, too.

I ask him. "Oh, yeah," he tells me. "Jessica isn't much of a dancer, but we had some awesome conversation. She can actually talk about football. Now if she was only a Seminole's fan."

"Why would anyone want to be a Seminole's fan? Did I miss something? Did they stop scouting the girl scout troops for their recruits?"

"Screw you." Rory laughs, "Go 'Noles."

"You mean Semi-Holes, not Seminoles." I tease back. It gets me the hugest grin from Sophie. She's originally from Ocala, Florida, and she's a die-hard Gators' fan. The arch-enemy of the Seminoles. I, however, am not that big of a football fan. Just Alabama and my beloved USA Jaguars. Thankfully both seldom play the Gators. It will just kill poor Sophie to have to root against her team, and for mine! At least the current COVID-19 outbreak spared Sophie that unpleasantness - USA's game against her Gators was canceled when the SEC went to a conference-only schedule. But I did find the cutest little bra and panty set for Sophie: it's royal blue and fringed in an orange lace. I let her wear that if her Gators are on TV and my teams aren't. She makes the most adorable cheerleader in it!

Jennifer sits quietly on the sofa and watches James with Rory. James looks to be utterly disgusted and humiliated. He is so clearly hoping his date is at an end. Rory doesn't seem to notice. He just goes on as if James had been thrilled with the date. All James wants to do is get away from Rory.

Rory, however, won't have any of that. He's standing close beside James, holding him with an arm sweetly around James' waist. James tries to shirk away, but it does him no good. Rory must have some strength in those arms. He isn't even working to keep the hefty "Jessica" nuzzled at his side.

And then, Rory does what all guys inevitably do at the end of a date. He puts "his moves" on "Jessica." He moves a little quickly. Not so fast, but fast enough that James doesn't see it coming. Rory just swivels his head around and puts his lips to James. Before James knows what's happening, Rory's tongue is slipping into his mouth.

James flinches hard. Very hard. He tries to pull back from Rory's kiss. But Rory keeps his arm around James' waist and holds him tight. Not just still, but pulling James snugly against his body.

With their lips together I don't have much of a view of James' face. But I can see enough of it to know it's scrunched up. And I can see the skin of his cheeks paling. I can see the tension in his muscles, especially at his neck, as he keeps trying to pull away.

James doesn't have a chance. Rory holds him and keeps right on kissing him. It doesn't even seem to matter much that James isn't kissing him back. In other words, Rory is being such a typical guy! I wonder how many girls James has put this same move on. I hope now he really understands how the girl felt when he did.

Jennifer watches. I don't want to disturb the scene, so I don't say anything to her. But I do try to read her face. I don't even have to do that to know that this move has been put on her more than a few times. I think all women have gotten it at some point. It doesn't look like she's too bothered to see James kiss a guy. Nor does it seem to bother her too much that James is so obviously less than willing. Maybe she shares my sense of poetic justice.

When Rory finally releases James, he quickly turns his head away and gags just slightly. Everyone laughs, but we mute it. Then Rory tells James "You are such a hot kisser, girl!" James immediately gags, this time hard.

I slip onto the sofa beside Jennifer. Since she doesn't seem offended by what she's seen so far, I lean over and whisper into her ear. "I want James to really grasp womanhood. Especially the way men so try to take advantage of us after a date. I want him to understand what it's really like to be pressured into something he doesn't really want to do yet. You know James better than anyone. If that were James on a date with a cute girl, what would he want from her?"

"That's easy. Oral. We've been married 20 years and he still tries to get me to do it after taking me out someplace nice. He just loves it so much... I just don't like doing it nearly as much..."

I nod to Rory and point quickly to my mouth. It's enough of a cue for him where to go.

"Wait!" Jennifer suddenly whispers urgently into my ear, "You're not going to make him--" Jennifer stops in mid-sentence when she hears Rory.

"Come on, Jessica... how about a little treat after our date..." Rory says to her.

Jennifer averts her eyes. I guess she's figured out what Rory is going to try and cajole James to do.

James balks. It's clear he's not sure what Rory wants. And just as clear that he's sure, whatever it is, he doesn't want any part of it. He doesn't really say anything. He just sorts of stutters and sputters.

"You know, a little treat for me... Come on, Jessica, I really like you and it would like the perfect ending for our date... if you were just so good to me..."

I think that's when James figures it out. "No way!" He blurts it out urgently and very firmly, his voice riddled with disgust.

I join in, standing up and stepping over beside James. "Come on, Jessica, be a good girl..."

James tries to pull away from Rory and me. I take my crop and swat the backs of his knees with it. It's not a very hard swat, but it surprises him. His knees buckle and he ends up dropping onto his knees right in front of Rory.

"Oh, yeah, Jessica!" Rory says, his voice is suddenly enthusiastic. "That would be so sweet of you, baby!"

James tries to get back to his feet. My little foot, planted firmly on the back of his knee, keeps him down. He tries to squirm away.

Rory puts his hands to the sides of James' head. "Come on, baby...you totally know what guys like, don't you, baby... now you're just teasing me!" He nudges James head forward, towards his crotch.

"You want me to... LIKE A GIRL?" James blurts out desperately. He still tries to pull away from Rory. But we hold him down on his knees.

"You are a girl, Jessica!" I remind him in my mean-girl bully voice.

Rory just unzips his pants and lets his cock jut out. And it definitely juts out. It's even bigger than James'. I'd guess Rory has about seven inches of thick shaft. And right now, it's rock hard.

With James on his knees, Rory's cock point almost perfectly at James' lips. And the tip of his cock is only about an inch or two from those lips. It gives James a view I'm sure he never thought he'd get of a cock. Straight on. Rory's eager cock pointing straight at his face.

I'd never tolerate outright rape, here or anywhere else. But I will gladly pressure a sub to do anything. Even things he thinks he doesn't want to do. Or doesn't want to do. I casually take my foot from James' knee. On cue, Rory holds James' head only lightly. Light enough that James could easily pull away if he tried. Rory strokes the side of James' face affectionately.

"You are such a tease, baby." He tells her in his sweetest voice. I wonder how many girls, and guys, have heard that same voice from him after a date. "Come on, Jessica, stop teasing me and make me the happiest man alive..."

He gently nudges James' head forward. "Jennifer!" James blurts out desperately, his voice now pure panic. "Mrs. Palmer, please! I'm sorry for being a male pig! Please, don't let them make me do this! I'm not a girl! Please!"

Jennifer surprises me. "Why not, Jessica? James always tries to get me to this for him after taking me out. If James wants me to pay for my date on my knees, then Jessica can damn well pay for her date on her knees!" She says it rather firmly, too.

Rory taps the back of James' head. A little tear rolls out of the corner of James' eye and down his cheek. Rory taps the back of his head again, nudging his lips a little closer. Not they're almost touching the tip of Rory's cock.

I reach down to James's jaw. I pinch the corners of his mouth hard, forcing his jaw wide open. Then I take my fingers away. James's mouth stays open, but not quite as wide. In front of his lips, Rory's cock twitches a tiny bit. James's face wrinkles. He closes his eyes. Then, very slowly, as reluctantly as possible, he moves his lips forward.

I'm sure James is wondering how far this will go. I'm sure he's counting on Jennifer, if no one else, to stop it before it gets really bad for him. I don't know about her, but I know neither Rory nor I will.

James plants a very light, and exceptionally quick, closed-mouth kiss atop Rory's shaft. Then he pauses for a second as if he thinks we'll magically decide he's gone far enough and spare him. "Ooh..." Rory purrs, "that so good Jessica, let me have it, baby..."

I tap James again on the back of his head. He gives it another little kiss. I tap him again. This time he opens his lips and takes about a quarter-inch of cock head into his lips. Then he just kneels there with it in his lips for a couple of seconds.

"Quit being a tease, bitch," I scold James, "be a good girl and give Rory a real blow job now." I tap the back of his head.

No one has a hand on James when he finally gets himself moving. He starts inching his head forward. It's the most reluctant blow job I've ever seen, and I've seen more than a few of them.

James moves his head slowly. He takes very little of the cock into his mouth, really no more than the head of it. I don't see his cheeks puckering in, so I doubt he's sucking. And I'm sure he's not even thinking of using his tongue or anything else skillful. He keeps his hands on his thighs, something I suspect is mostly because he doesn't want to be touching another guy if he can avoid it.

I scold him to suck. "After all you guys do call it 'sucking dick,' don't you. So suck, bitch."

A second later I see his cheeks pull in, but very slightly.

Rory purrs a slightly loud "Oh... yeah, baby." a few seconds later he puts his hands to James's head and grips it by James's ears. He starts pulling James forward, steadily making him take more and more of the cock into his mouth.

Its' not long before James is taking about half of Rory's cock into his mouth. It's enough of Rory's big shaft that James has got to be feeling the tip of Rory's cock head against the back of his mouth with every stroke. "That's it, baby, you are dynamite, girl!" Rory encourages her as he releases James' head.

James reluctantly, and slowly, keeps sucking on Rory's cock. I decide that James must have some secret fantasy about doing this. He must. If that were me on my knees... I have teeth, and Rory would now be a eunuch. I don't do anything when I don't want to. I've been pressured by a few guys, but that never got them anywhere with me. Just kicked out and assured it was their last date with me and anyone I know. But few girls have the assertiveness that I do.

He doesn't look happy about it, but James goes on sucking Rory's cock. He must be doing a fair job at it, too. I can see that Rory's cock is staying at its full rock-hardness. And I can see the tanned flesh of his shaft glistening with a fine film of James's saliva. I just try not to think about that flesh got its suntan. Clearly, there isn't a tan line anywhere on Rory's body. Anywhere.

It goes on for about three or four minutes. James sucking Rory's cock as inexpertly as it can be done. As if it's his first time, ever. Which I'm certain it is.

Rory finally grabs hold of James's ears again. At the same moment, Rory's hips start thrusting forward with long, sharp, powerful strokes. Each stroke seems to ram Rory's shaft a little past James's comfort point, making James gag on it as the head of Rory's cock goes too deeply into his mouth. Rory doesn't notice. Steadily his thrusts grow even sharper and more urgent.

It goes on for maybe fifteen seconds. By the end, James' head isn't even moving. It's still, Rory holding it in a vise-tight grip as he rams his cock into James' mouth as if it were a pussy. Or a bottom. I'm just assuming the bisexual Rory is no stranger to either.

Rory grunts a very loud, and satisfied "AH!" He draws it out for a couple of seconds. As he does, the thrusts of his cock soften.

James' face scrunches up hard. He gags and keeps gagging hard. A second later I see the first drops of Rory's white, creamy cum start running from the corners of James' mouth. I guess now he's gotten a good taste of Rory. And knows what a man tastes like for a girl.

Rory goes on his strokes a little gentler, but still fucking James's mouth as he holds it still. It takes him close to a minute to finish his orgasm. Only then does he pull back far enough that his cock slips from James's lips and releases James's head.

James immediately turns his head to the side, gagging hard as he does. He chokes. Then his head falls forward as he coughs out a good-sized puddle of Rory's cum. It doesn't help. No will spitting get that taste out of his mouth. James keeps gagging and spitting.

I grab hold of James by his ears. It seemed to work for Rory, and it's definitely a demeaning way to control a man. I pull him up to his feet.

"You naughty little girl! Didn't mommy teach you any manners? Girls do not spit all over their hostesses' floors. That is just so rude!

"Come along. Since you want to be a rude girl, you'll just have to learn to behave!"

Chapter 05: Relief

Rory excused himself and left after thanking me for introducing him to Jessica. Jessica, Rory assures me, was a very fun date.

I took James back to the playroom. Jennifer came along, too. As soon as we got there, I again cuffed James' hands to the back of his neck. Then I told him it was time for his punishment, that now he was going to learn to respect a woman's home. My home specifically. Then I gagged him again. But once he was gagged, he was greatly relieved as I had Sophie undress him. Fully. I doubt it was his eagerness to be naked in a room full of clothes ladies. But he was definitely eager to be out of his dress. And his panties.

No one has a clue what I'm going to do with James now. Not even Sophie. I haven't told her anything. She probably has a guess, though. I've owned her long enough that she has a pretty good idea of what I might do with a male toy. At least in a general sense. But poor Jennifer is clueless as her husband stands there, nude and bound. Well, almost

I get the vise. Usually, I'd send Sophie for it, and anything else, but this time I do it myself. It's behind James, and I don't want him to have a clue what's coming.

The vise is just that, a fairly typical, and common, vise. It could be in any workshop, except for the few little modifications I've made to it. It's atop a metal post the same size as it's base. The bottom of that post is firmly affixed to a little metal base about four feet square, with wheels.

The vise has a pair of narrow jaws. They're about a half of an inch tall, and four inches wide. They even have little crosshatches on them to grip whatever is in those jaws. And like every vise, those jaws are firmly attached to heavy arms that curve inward as they rise up from the screw handle that tightens the vise. Beneath the jaws, there's nothing but air for several inches, until finally, the tightening screw runs through the arms and the space between them. The curve of the arms left me plenty of empty space between them, the space growing quickly the further from the jaws. To the very bottoms of the jaws, I've attached some metal plates that hang down to just above the screw. Those have a thin layer of foam on the "inside" of them, the sides that face each other. And they're bowled with a curve almost like the long side of an egg. Closing the vise will push the edges of those plates together, but their curve leaves a small little gap in the center.

I roll the vise up behind James. Then I take hold of him by his shoulders and guide him to walk backward. Just before his bottom touches the cold metal of the vise, I snip the string still holding his cock bound up underneath him. It pops up a little, still soft, but no longer held underneath his body. His balls drop free and hang low between his legs, too. I keep him moving backward until he's standing directly over the vise.

The vise's jaws are wide open. I tap James' legs with my crop, commanding him to open his legs to the edges of the platform he's standing on. As soon as he does, I motion for Sophie to come take care of those feet. There are already leg irons bolted to the edges of the platform, one cuff on each side with a few inches of chain. It doesn't take Sophie any time at all to lock one cuff around each of James' ankles. That's all it will take to ensure that he keeps his legs spread wide, which is all that matters.

James's balls dangle down between, and well beyond, the jaws of the vise. At first, he doesn't seem to notice much or even be thinking about what's under him. But once I've closed those jaws enough that he can feel the foam on those curved plates beginning to touch his balls, he flinches so hard he about jumps up. He doesn't go anywhere. The chains keep him fairly still while I keep slowly closing the vise.

At first, it's the soft foam touching the front and back of his sack that James feels. Then, with another crank on the vise, and he can feel the foam beginning to lightly squeeze his balls from both sides. I keep going, but I do pay careful attention to how his balls are hanging in the vise.

James very suddenly becomes very nervous. He squeals a high-girly squeal, unlike anything I've ever heard from him before, into his gag. He trembles. He tries to wiggle, and for the briefest of seconds, he manages to get a little wiggle from his hips. But then, as he moves, he feels the narrowing cups around his sack, as his balls try to pull into an ever-shrinking space. He realizes that the biggest space is the place where his balls already are. And that already the cups are too tightly around them for him to pull his balls out from them.

I close the vise all the way, slowly, letting James feel it slowly squishing harder and harder against his balls. When those jaws are fully closed, the narrow strips of crosshatched jaws are fully closed on the very top of his sack, flush against his shaft and cheeks. But his balls dangle just beyond the closed jaws, into the cups, where they have about ½" of space to hang in. It pushes them firmly together. And it puts some pressure on those soft balls, squishing them very uncomfortably, but not enough to injure them. Another, final, tiny turn on the screw and he really feels the pressure of the shrinking space on his balls, and the bite of the jaws squishing hard across the very top of his sack. Tight enough that he hasn't a chance of moving it.

James does not look happy. In fact, he looks exceedingly uncomfortable. His face scrunched up tight, his eyes squished shut with little tears leaking from their corners, as James groans very pained and desperate "OW!s" He quivers, too, but does it standing very still. At least his hips don't move. He doesn't dare. He's already learned that moving them will do nothing but reduce the space they have. He looks exceptionally nervous, too. I know the vise is tightened just right, too. Every time James makes even the tiniest of moves, he cries out.

I reach down and finally takes the sheath off his cock. It's not hard to do, now that the string is cut. I just have to pull it off from the back, the side at his pubes. The instant I have it off his soft length, I let go of his cock. A fraction of a second later it's sprung up to an incredible hardness, standing straight out from the tops of the vise's jaws.