A Sissy's Date Night

He has a slightly rounded face. I just can't tell if the rounding is so much natural, or if it's a couple of extra pounds rounding out sharper features. He has short hair. It's dark brown and neatly combed. I can see a pair of blue eyes. They're not the most brilliant, or glowing, of eyes, but they are definitely blue. Beneath that is a modest nose that's slightly wide, and well rounded. And then, there's his mouth. It's just on the wider side of average, but mostly straight, and framed with a pair of light purple-tinted lips.

And then the weight starts to show. His shoulders are defined, but the extra pounds round out their features. His chest, and his stomach beneath, are not what I'd call flat. They're more rounded, like a tree trunk. A trunk that noticeably hangs loose. Its skin is loose, but it also hangs down, not quite a full "roll" of fat, but enough of a start on one.

Thankfully his stomach doesn't hang down nearly far enough to offer any coverage of his cock. That would definitely have surpassed the "fat" line. Instead, it only sags to about his waistline. I could see that his pants were underneath the little overhang, not atop of it.

It leaves his cock fully exposed for my inspection. Now, it's mostly hard. Not quite its stiffest, but certainly hard and well on its way to steely hard. It stands out from a nest of deep brown tangles, not quite straight yet, but standing up and drooping down only a fraction of an inch from straight. Beneath that cock, hang a pair of decently-sized balls, loose in a wrinkly sack.

I'm sizing James up as if he were a piece of meat at my butcher's. And I'm making a show of doing it. A very big show of checking out everything. Not just his private areas, although I'm taking great care to make sure he knows I'm sizing those up, but also the parts of him that he should be the most ashamed of, like his loose, sagging, stomach.

So I take a moment to size up his bottom, too. That's about the most unshapely part of him. His cheeks have swollen to the point where they've lost most of their roundness, instead taking on a loose, hanging, and free look. But they've yet to grow so wide as to expand out past his hips. At the bottom, they sag only slightly, a bit of flab hanging down along their bottom edge, growing slightly as it flows inward to his crack. His crack is obviously closed. Those cheeks are too plump for it to hang open. It's going to be deep, too. He definitely needs a few laps around the equator's worth of mileage on a treadmill. It's the softness of them that I don't care for. I like my cheeks toned and squishably soft. This is the bottom of a man who spends a good part of his life sitting on it.

But he's not so large that his arms and legs really show it. His arms barely at all, only at the tops, where they look to be more loose. It's about the same with his legs. I can see a couple of extra pounds atop his thighs, especially at the insides, where it makes them look rather loose.

I have Sophie fetch me a few things. I leave James standing in front of his seated wife. It has her eyes almost level with his cock. A cock that's only about a foot from her eyes, maybe a little more, but not much. I just wait for Sophie to bring me what I've asked for. Asked for in a way that James won't know what she's fetching.

Once Sophie is back, I start by looping a long, thick, plastic tie strap around his neck and securing it. But I leave plenty of slack in it, turning into an impromptu collar. Then I take hold of his wrists and bring them up behind his neck. I click a pair of handcuffs on his wrists, slipping their chain through the tie strap. It will ensure that his hands stay up at his neck. No matter what he wants.

Then I gag him. I use a standard ball gag with one tiny modification to it. I've added a little plastic flange, like a tongue depressor, that stands out behind the large ball a couple of inches. It's not quite enough to choke him, but as I wiggle the ball into place just beyond his teeth, I hear him start choking lightly for an instant before it settles. The ball fills his mouth, squishing its sides against everything beyond his teeth, and leaving his teeth to show. It holds his mouth open at its full wideness. If his jaw would allow it, the squishy ball would have it stretched even wider. The little plastic tab lies against his tongue, curving gently at its tip, and presses his tongue hard down. It ensures his tongue won't be moving a bit. Once I have the gag's strap cinched snug around his head, I blindfold him.

None of that seems to come as much of a surprise to him. Maybe Andrea warned him that he might be tied. More likely he's seen plenty of porn online. While most of it is ridiculous, some of it is real enough, or close enough. Close enough for him to have guessed that blindfolds, gags, ropes, chains, and handcuffs typically come along with the whips and crops. Either way, he wasn't surprised or shocked.

And now, he's incapable of doing much on his own. Like objecting to anything. He won't be making a sound unless you count a simple primal grunt. That's all he'll manage with his tongue immobilized. Nor is he going anywhere. Not in an unfamiliar apartment while unable to see. And nor will he be doing anything that requires hands. His are utterly useless to him where I have them bound.

"You are here to learn to appreciate womanhood, sissy. So that's what you will do. However, before your lesson, you must be properly cleaned up and groomed. Us ladies care about our appearance, and we put a lot of work into looking nice for our men. Or in Jennifer's case, for her worthless sack of flab.

"Obviously you haven't a clue how to properly groom that wimpy, soft, sissy's body. At least I hope not, since you haven't. I will have my slave do it all for you. You will behave for my slave-girl. Let me make this clear, you do not want her to call me."

I snap my fingers. "slave. Come." Sophie hurries over and drops to her knees. "Groom this sissy bitch."

"Yes, Mistress. Thank you for entrusting this ridiculous sissy to me, Mistress. I won't disappoint you, Mistress!" She grins as she promises me. I know one thing Jennifer doesn't. Why Sophie is grinning. She just loves to play with cocks, and I've just given her one to amuse herself with. I know she'll take full advantage of the opportunity, too. But if I hadn't wanted her to, I would have told her not to.

Sophie rises to her feet. She's a small girl, like me. Just not quite as small. She has just over an inch on me. But she is lean and her body has a very curvy feminine shape to it. I know James likes her shape. I saw him checking it out the instant he saw it. Then again, the tight stretchy dress she's wearing so immodestly flaunts her body. And her pert breasts.

She takes one hand and wraps it around the shaft of his cock. As her slender fingers are closing around it, his cock snaps to full hardness. It lets me see that his cock isn't that great. It's about 6" long, maybe less, but at least close to six inches. It's not big, but at least it's on the right side of "average." But not by much. It's moderately thick, though. Thick enough to make up for its shortness. I'm just guessing that it might be somewhere approaching 1 ¾" thick. He's circumcised, which leaves the light purple-tinged head of his cock exposed. It seems to have an almost triangular shape, but obviously with its tip well rounded. What it doesn't have is the "bell shape" of a real man. That ridge where his cock head swells out past the edge of his shaft. On this cock, the head more seems to just suddenly change color at a little wrinkle and become the shaft without standing out wider or past the edges of his shaft.

"Sissy bitch..." Sophie coos in a very sugary and equally taunting voice. Plus Sophie has a pretty strong accent of the deep south, far more than I do, and that gives her girly voice and little sultriness. "come with me, and I'll groom you like such a pretty little bitch!"

Sophie doesn't wait for an answer. She doesn't need one. She heads for the bathroom. And she keeps her snug grip on his cock, using it for a leash. As men always do, James quickly springs into action and follows his cock. I love leading men around by their dicks. If the giggling smirk on Sophie's face is any kind of clue, so does she. Using her "leash" she leads him away.

And then, once James has followed Sophie as far as the hallway, Jennifer giggles. "I've always wanted to do that!"

"What's stopping you?" I answer, "it's better than a real leash. Men always follow their dick." It gets me a fresh giggle from Jennifer.

Chapter 02: Cleaned Up And Out

Sophie takes James to the bathroom. I have two in the apartment, one off of my bedroom that's only for me (and my BFFs), and one off the hall for everyone else from guests to slaves to whores, and even sissies. This one is just a basic, average, apartment bathroom with a tub/shower combination. But that's not the first place Sophie takes him.

While Jennifer and I chat some more on the sofa, and I finally give Jennifer the first hint about James' lesson tonight, Sophie pushes James down, sitting him on the toilet. Since he's unable to do anything for himself right now because of the cuffs and bindings, she takes the moment to position his cock. Or would, except that rock-hard shaft refuses to do anything except stick straight out.

I can hear her scold him in her sternest voice, "stop being such a horny little pecker! My Mistress didn't give you permission for a stiffie, not even one that little! Now make that thingie soft before I have to beg my Mistress to come whip it soft!" It still takes him a couple of minutes, but it sounds like eventually his cock softens up enough that she can aim the tip of it down. I hear her telling him that he has to pee now. Has to. It's not a choice. And a minute later I hear her telling him that pooping now isn't a choice either. Mistress demands that her bitches be clean, inside and out, and he's going to clean himself out for me.

I ignore it. Jennifer can't seem to. She comments to me. "Gawd, you're going to make him just so obedient, aren't you? I mean, toilet on command?"

I giggle. "Well, I know I usually try to go before a date. That way I don't have to leave him sitting there while I make a trip."

"Yeah, I used to, too. When I was still dating, that is. Like an eternity ago."

"There you go! He's going on a date, isn't he? You want him to really know what it's like to be a girl, I figure he should be doing all the things girls do to get ready for our dates. And trust me, I know little sissies like him. They always try to weasel their way out of everything. But not here. Oh, no."

A couple of minutes later Sophie hurries out to me and kneels as she waits for permission to speak. When I allow her, she tells me "I'm so incredibly sorry, Mistress! I'm trying! But that stupid little bitch in there just refuses to clean out his bottom for you, Mistress!"

"Very well, slave. Fetch me a yellow one, number 12, with an 8 tip." I tell her sweetly, "I'll take care of it and teach the fat slob to be an obedient fat slob."

"Thank you, Mistress!" Sophie squeals excitedly. Then she hops to her feet and scurries off.

I get up as well. Jennifer asks me, a slightly wary note in her voice as it sinks in just how deeply she's gotten James into this, "What are you going to do to him?"

"I am going to teach him that obedience isn't a choice here. That when I say to do something, he's going to do it, whether he wants to or not. And if he tries to be a naughty, disobedient, bitch, I won't care. He'll still end up being obedient. Just less comfortably than if he behaved his jiggly butt." I'm smirking wide, and it's my evil smirk. I think Jennifer catches it. She asks if she's allowed to come along. I tell her "of course you are! This will be quite a show!" She looks suddenly uncomfortable as she rises to her feet. And follows me to the bathroom, a slight hesitancy in her steps.

By the time I get there, Sophie's there already and waiting for me. What I asked for is sitting on the counter beside the sink. A twelve-ounce syringe-style enema, preloaded with the yellow fluid (mineral oil with a couple of drops of food coloring). It has an eight-inch long, pencil-thick, pre-lubricated tip already attached to it. It looks huge. The clear syringe is the same size as a can of soda, and just as full.

Beside the counter, James sits on the toilet, dumbly oblivious to what's going on. And to what Sophie has brought in.

Jennifer, however, freezes in her steps as she sees what I've ordered up. And knows what's about to happen to James. Something she definitely did not consider might be on the menu tonight. Oops. I had warned her that everything G-d created was a possibility. I'm sure He created the enema. Maybe right from the start. For all I know, Eve used to use a good enema to keep Adam in line!

I don't waste my time. Nor do I bother with any niceties for James. I just reach down and grab a big (OK, small, but only because my hands are so small) handful of cock and balls. "On your feet, bitch!" I snap in a cold, stern, and disapproving voice. I don't wait for James to get his bulk moving. I pull up, and I pull hard. James cries out a grunt that's as much shock as it is pain. He about jumps up to his feet, too.

I glance in the bowl. It leaves me no question what he's done and what he hasn't. "Didn't my very polite and obedient slave tell you to empty that bottom, sissy?" He can't answer. He can only grunt and nod his head. "Never mind, she's obedient, of course, she did.

"But you are disobedient since you didn't." I release my vise grip on his balls. He exhales with relief. I grab his head, shifting my hand up just as quickly as I can. Then I pull his head forward and down, half pushing him, half throwing him, down to lean over the counter with his face in the sink. "Don't say I didn't warn your sissy butt, bitch."

I use one hand to shove his loose cheeks apart. Way apart. They're big enough, and loose enough, that they jiggle as I shove them apart. I wonder how Jennifer can stand this guy. I'd never let him touch me.

It completely bares his asshole. There's a faintly pink wrinkle, a single line, that begins in the fur on his sack and runs straight up. Around the bottom edge of those big cheeks, that little line runs into a slightly-purple, and irregular, swatch of skin. There are a few strays hairs on his cheeks, but not many. A couple of more in his deep crack, but they're all a little ways away from his asshole. That's fairly large. But it's also tight, or at the very least, tightly closed now. It looks almost like a little line, maybe a quarter of an inch long. All around it, the darker flesh steadily wrinkles up into little lines that all flow into that tiny slit. But I don't see a defined ring of muscle, as I'd prefer to. His asshole looks more as if the darker, wrinkle flesh, simple turns inward and caves in. Obviously, there is a ring of muscle, but the extra pounds on his cheeks are enough to conceal it.

I put the greasy tip of the enema syringe against the little slit. James immediately cringes. He flinches. He groans something long, very desperate and pleading, that the gag ensures no one has a clue as to what he's trying to beg. He tries to stand up. I shove his shoulders back down, pushing them firmly against the counter with a faint crash. He wiggles his bottom, jiggling his cheeks as if trying to move his asshole away from the tip.

I shove. And this time I'm not especially gentle about it. I just shove every bit of the eight-inch long tube right through his asshole. Almost as soon as the very tip of it presses into the valley of his ring, James grunts out another desperate-sounding plea for mercy, in the form on a primal grunt. I can see his asshole tense uptight, squeezing hard against the narrow tube as if that's going to stop it!

I don't stop until the base of the syringe is flush against the valley of his crack. Then I start steadily pushing the plunger. The liquid immediately begins filling his rectum with its icy coldness.

James cries out loudly and urgently. He's not still, either. He tries to stand up again, and I shove him back down a little harder. He tries to get his bottom away from me. He doesn't. After a couple of seconds, and not much more than a couple of ounces, I see his hands gripping hard onto the back of his neck - the only thing they can reach. A second later I see his toes curl up, too. And his body gets stiff. He tries once more to grunt out a plea for me to stop.

He gets about half of the enema before he grunts out with the discomfort of being filled to his limit. A limit he's not even close to yet. He tries to shift his hips to the side, to step tot he side, away from me and stand. I don't let him. I keep him pinned in place, leaning over the counter, and getting his bottom pumped full.

Around the halfway mark, James really starts to fuss about it. His grunts turn strained, showing his discomfort. His squirming grows hard, too. But I can keep him pinned in place. And I do. I don't stop until James has every drop of the fluid inside his bottom. Then I yank the entire length of the tube out with a single, fast, sharp pull. His asshole cinches impossibly tight the instant the tube is out of it. And now I can make out the faint lines of his ring of muscle, as both, he strains to clench tight, and the fullness in his bowels pushes hard against the inside of his asshole, puckering it out slightly.

I grab James should and pull him to stand up. He cries out a very deep and pained grunt as I force him to keep moving despite the sudden cramp he feels, low in his gut, right where his pubes meet his waistline. I shove him back against the wall. With a single hand against his chest, right between his nipples, I hold his back against the wall.

"Now would you like to be a good sissy and go potty for my slave-girl?"

He nods yes vigorously enough that I could imagine his head flying off his shoulders. He must want me to know just how badly he would like to behave now. I can even see a little wetness at the corners of his eyes as if he's about to prove his sissy-hood and cry like the bitch he is.

There's no reason to waste a good enema. Since I've already gone through the trouble of filling his bottom, he might as well get the full benefit of its cleansing. "slave, this bitch will wait the full five minutes. It can just stand there where I put it. If it has an accident, come get me so I can teach it just how much more its fat bottom can really hold. With the help of a cork, that is."

Sophie giggles a very girly giggle. "Yes, Mistress." And she glances at her watch. I already know that Sophie will time him to the second. He won't get even that much leeway from her.

I leave them standing there. Jennifer decides to follow me back to the living room. "You're going to make him wait... like that?" She asks with as much discomfort as questioning in her voice. I tell her that I am because that's how long it takes for it to have the full cleansing effect. And since I had to administer it, he's getting the full treatment. "Of course, if he'd obeyed my slave, he wouldn't be suffering right now. Hopefully, he'll learn that I don't care how uncomfortable he is. He will do what he's told. Or I will make him. You have to admit, that enema is going to make him do what he was told. No matter how little he'd like to. The discomfort of it will only remind him that obedience is the better path here."

Sophie makes him wait. And when she finally returns him to the toilet, I can hear the explosive jet of water spewing from him all the way out here. By the little cringe I get, it seems like Jennifer can hear it as well.

Chapter 03: Dress Up

It's an hour later before Sophie leads James back out to the living room. By now he's not only used the toilet but has been thoroughly "cleaned up." His teeth are brushed and flossed. He's been put in the shower. His face has been shaven. His body has been rendered totally hairless from the shoulders down.