A Sissy's Date Night

And Sophie has put makeup on him. Expertly. A little cover-up to smooth out his face. A little powder. A little mascara. Pastel green eyeliner. "Slut red" lipstick. She's even tweezed his eyelashes and plucked his eyebrows.

Jennifer gasps when she finally sees what I've done to him. Despite his size, he now has a decidedly feminine aura to him. Well, as much as Sophie could do with makeup and some Nair. There's nothing I can do about the way he carries himself. At least it's not ultra-manly like a linebacker or something. But there's no flow or gentle wave to his walk either.

"Oh my Gawd!" Jennifer gasps. "he almost even looks like a woman!"

I laugh. "Hey, the best way to learn to appreciate women is to be a woman! Now he gets to be a woman for a couple of hours. After this experience, he won't be nearly such a pig!"

I send Sophie to fetch the clothes that I ordered for him. He does have a date tonight. He might not know that yet, but he's the only one. And just wait until he sees the surprise I've got for him!

Sophie giggles loud and long as she hurries off to fetch the box. I didn't buy him anything expensive, even though Jennifer actually paid for it. I just clicked up a few little things on Amazon. But even though Jennifer paid for it, she hasn't seen what I've chosen for him. Now that I see his size, a tiny part of me wishes I'd picked something else. A very tiny part. The rest of me is going to enjoy the added humiliation of this outfit.

Once Sophie is back, I start getting him dressed in the same order that a woman would dress for a date. Or at least that I would. But I leave his hands bound, and I leave him gagged. It'll work better this way. HE won't be able to object.

Sophie brings out the first item. A pair of sheer, see-through black panties. They're in his gargantuan (for a woman) size, but they're still tiny. They have a little triangle of a fabric that's silky soft but almost looks like window screen on the front. It will barely cover his pubes. They're not much bigger in the back, the triangle of identical fabric back there won't cover more than half of his cheeks. And they're cut low on his hips, with narrow little bands of a stretchy ribbon for their sides.

Sophie pulls them up on him. The first thing I notice is how the back of them leaves a little more of his globes bared than I'd anticipated. I count that as a plus. It covers his crack fully, but at the bottom, not much more before angling up to the waistband. A waistband that's at least a full inch, maybe more, lower than the top of his crack.

I peek around front. From there I can see the sack of his balls straining the fabric and filling it, puffing it out. His cock, now as stiff as a steel rod, stands up straight, the waistband of the panties holding it against his stomach. About two inches up from the base of his shaft. The rest of that stiff cock sticks out over the waistband.

"Oh this not going to do!" I squeal. I take hold of his shaft and pull it so it's standing out straight from him. It pushes the waistband of those panties down. I hold it tightly, giving it a good squeeze. "Didn't I tell you about having inappropriate thoughts? I didn't give you permission for an erection, so why is there one in my hand?"

I use my other hand to pinch the head of his cock. And I pinch it hard. James grunts and squeals into the gag. "No erections without permission, sissy. Stop being such a bad little bitch." After about three seconds, not nearly enough time for him to do anything, I release his shaft but keep my pinching grip on his head. I give his cock a firm, but not too hard, of a swat with my crop. "Erections are bad, sissy!" I count to five. I swat it again and scold him exactly the same.

By the fifth swat, his cock is nicely pink. But it's also floppy and soft, as hard as a wet noodle. I'd bet this is as soft as it gets. And it's shrunken. Now it's under four inches long, maybe closer to three inches than four. And no more than an inch thick. I hang onto it, keeping my pinch on its head.

"Obviously I can't trust a sissy like you to behave!" I scold him, "so I'll just make sure that useless little cock behaves itself!" I put a little excitement into my voice. "Slave, a Chinese tube, now."

Neither James nor Jennifer has a clue what I've sent Sophie for. But both suddenly look more than a little nervous when they hear Sophie excited giggling and her squealing "Oh, YES! Mistress!" OK, James looks to be far more nervous than Jennifer. It makes sense. Whatever I have in mind, James is going to suffer it. The worst Jennifer will have to endure is hearing how awful it was later.

Sophie returns with the device I asked for. It's just a little tube, made exactly like those little paper tubes we called "Chinese handcuffs" in grade school. Except its not paper, it's made of thin plastic strips, covered with a soft fabric, and interlaced. This tube is about five inches long, which makes it longer than his soft cock. And it's about an inch wide, but it's also almost fully relaxed now. And it has a long string attached to the tip of one end.

I start at the end that doesn't have the string on it. I put that right to the tip of his cock. Only then do I release my pinch on his sensitive head. And I quickly start shoving the narrow tube over his cock. It takes some shoving, too. His cock is just about as thick as the opening of the tube. But his cock is soft, and thus easily squished to a narrower width. Easily squished about any way I want, too.

I had Sophie leave James's blindfold off. Otherwise, the fabric of it would have just ruined his makeup! But it also lets him finally see. He watches as I stuff his cock into the little tube, his eyes wide, his face scrunched up as unhappily as it's ever been. I even hear a little moan of nervousness and revulsion through his gag.

Jennifer watches, too. After a few seconds, I see a little smirk on her face as she realizes how that tube is going to work. It's just not big enough to accommodate his stiff cock. As his cock tries to swell up, it will just strain harder and harder against the unyielding tube.

But that's not the worst of it for James. As soon as I have the tube all the way over his cock, Sophie hands me a long and narrow plastic tie strap, like a three-foot-long zip tie. I cinch that snug around his waist. Then I thread the string under it. It's a fairly heavy string. Heavy enough that there's no chance of it breaking.

I pull the string tight. As I do, I position the tube, and his soft cock inside, to lie flush against his pubes. It pulls his cock flat against his sack. And then it pulls his sack flat against his body, pushing one ball to either side of the tube. The tip of the tube stops just before it would enter the crack of his bottom from the very bottom. But the string doesn't. It goes right up his crack the same as a g-string would. One I have his cock pulled flat and tucked up underneath his pubes, pinning his balls up too, I tie the string off.

Then I pull his panties back up. Now they look like panties on a girl. And sit almost the same! At least the same as they would on a woman with a puffy pussy mound. But panties take that into account. "That is so much better!" I squeal happily.

James is not happy. I'm sure he can already feel the tube squishing around his cock. I don't know if he's figured it out yet or not. But that tube isn't widening. Nor is going anywhere. His cock is going to stay right where I left it, tucked up under him, squeezed fully, and even curled. No amount of blood is going to swell that cock to stiffness now. Instead, whenever it tries to get hard, it's just going to strain against the tube and become painful for James. The pain will remind his cock that it doesn't want to be hard.

Next Sophie puts a pair of slightly dark tan nylons on him. And follow those up with a garter belt that matches his panties.

Sophie comes out of the box with a matching bra. It has the same sheer see-through cups. Or what it passes as cups. They're more just lace-fringed triangles of fabric. I've chosen to make him a C-cup. It's a reasonable size, and not too big of a size, with a band of 44. Most actual females with a 44" band would have much bigger breasts than a mere C-cup. They'd be loose, but they'd be big. James's breasts aren't going to be loose. That's because his are little bags of saline with a thin covering of foam. But the strapless bra does its job. It pulls those pseudo-mounds up and pushes them together into a nice pair of pert breasts with a full, but lace-covered, cleavage between them. I had to find a bra like this, one that covered the insides of his mounds but was also skimpy. Since his mounds are prosthetic, it's not like I could let them show. But I wanted him to have the full experience. To know what it feels like to have guys trying to peek down that cleavage.

Next Sophie has a slip for him. One with a high hemline at the bottom.

And then, there's his dress. It's a dark hunter green. It's silky and shiny, too. It's strapless, hence the need for a strapless push-up bra. That lets Sophie put it on him without unlocking his hands. She just pulls it up over him. It is not a dress that flatters an ample figure. I wondered why they'd even make a dress like this in a size this big. Surely no woman is so tawdry as to wear it! It snugly hugs his body. Its bottom hemline is only a couple of scant inches beneath the lowest point of his bottom. On top, it snuggles him all the way to his breasts. It has a little dip for his cleavage, but not much of one. It hugs him tightly.

It's a dress a girl with a figure would wear on a date. Not a girl with a figure like his. I like the high hemline of its skirt. He is so going to learn a few womanly tricks from that hemline. Like to squat instead of bending over and poking his bottom out for the world to gawk at. I'm sure he'll learn to appreciate how much trouble these tight, sexy, dresses are, too. How that skirt is going to be constantly creeping up his thighs and forcing him to fix it.

I have a pair of four-inch-heeled pumps for him to wear, too. They're high heels, but pumps are much easier to walk in, and I don't want him tripping over his own feet tonight. Besides, pumps do have a "fuck-me" aura to them.

I even accessorized the outfit for him. I found a pair of white earrings for him to wear. They're clip-on. And they are big bimbo hoops. And I have a white purse to go with it. To make sure he carries his purse as a woman would, I've put a few things in it he won't want to lose. Like his driver's license and other IDs. No money. No phone. But a couple of spare tampons, and the tube of lipstick for touch-ups. Even though I know he's not going to touch it up.

Now that he's dressed up for his date, I have Sophie take him to the little hard stool beside my desk. And sit him there. Where he sits, bound and gagged, while us actual ladies completely ignore him.

The knock on my door comes exactly at 6:00 pm. Sophie answers it, and after making sure it's the person I'm expecting, shows him in. I haven't met him before. All I know about him is that his name is Rory. He's a junior at Florida State University. And his BFF is good friends with my BFF #2 (Reagan's) boyfriend. I care that he's from somewhere else. I care that he male. And willing to help out. And that's about all I care about. It's why I asked Reagan if she knew anyone. FSU is over 100 miles from here! (I still can't believe she went there, just because her boyfriend did! She could be here at USA with us!)

I introduce myself to him. Jennifer sits with a surprised look on her face. Then she eyes him over rather appreciatively. She must be assuming that Rory will be my date tonight. He's cute enough. He's tall, around 6'0". He's lean and it looks like he is decently muscular. Reagan told me that he "played sports." I didn't even guess what she meant by that. He's no linebacker, but he definitely looks athletic. He tells me that he's on the volleyball team. Not exactly the football team (not that I'd call the Seminoles a football team anyway), but he's still cute.

Reagan told me that he was "a prankster." I can see that in him almost immediately. She also told me that he's bisexual, a total "man-slut" and even after she told him what I wanted, he was willing. He thought it would be"hilarious." Fine by me.

Rory has a slightly "shabby" look to him. His hair is dark and wavy, cut neither long nor short, but bushy as it hangs almost to his shoulders. He has brown eyes. But he is cleanly shaven. And I catch a whiff of some aftershave or cologne, something with a "beach-y" scent. He's dressed nicely for his date, by college standards. He has clean jeans on, with a pull-over short-sleeved shirt. And sneakers instead of flip-flops. He's very well-tanned, too. He looks like he belongs on a beach. But maybe the entire volleyball team looks like him. It is kind of a beach sport.

I guide Rory over to where James is sitting. "Rory, this is Jessica." Now that James looks like a woman, I figured he needed a new name to go with the new look. "Jessica will be your date tonight."

Jennifer's eyes about pop out of her head in surprise. I've told her that James was going on a date tonight, I just never mention that he was going to be the girl on the date. Apparently, she must have assumed James would be paired with a woman! Now how would he ever learn about being a woman like that?

James shirks back, a look of horror sweeping over his face as it dawns on him that he's about to go on a date with another man. And much worse, that I've just turned him into a girl for it!

I tap James on his hip with my crop. The light sting of its swat is enough to get his attention. I sternly tell him "say hello to your date, Jessica, and be polite like a proper girl."

James sits there for a second. Then he stutters badly, his voice breaking, as he finally says "hello, Sir, it's nice to meet you..." The shamed muteness of his voice, and the look on his face that he's anything but pleased.

"Hey, Jessica..." Rory smiles at him. "You look seriously sweet tonight." He smiles. It makes James cringe even more as he thinks that this young man might actually think he does look decent as a girl.

I'm sure James thinks he looks ridiculous. But he doesn't. Sophie has done her usual excellent job. James looks like a woman, albeit a fairly heavy one. One would have to look very closely to see that "she" is a he. Up until it comes to the way James carries himself. There's still too much masculinity in the way he moves. Not so much he couldn't pass for a masculine lesbian, but too much for a girly girl. And then, there's his voice. But there's not much I can do about that.

"I thought we could grab a bite..." Rory is still smiling as he offers James his hand. "There's an awesome place around here that's got a live band, dancing, and I'm told edible food. I hear you like country music, which is what they've got tonight." I picked the place. Mostly because it's one of the places around here where they know me. And they don't mind... whatever, as long as everyone behaves. They don't mind same-gender dates. They don't mind when I bring Sophie in on her leash. They don't mind much. And I know the bartender. I've warned him what I sending tonight. He just laughed hard and assured me there next time I come in, there's going to be another picture over the bar.

James very reluctantly takes Rory's hand and allows himself to nudged up to his feet. He stars at Jennifer with the most pleading look on his face, as if begging her to end this lesson. I'm sure he'd love to assure her that he's learned his lesson. But he doesn't. He doesn't have much time to. Rory is fairly quick to lead James over to the door.

"Remember, Rory, Jessica has a 10:00 pm curfew."

"Sure. I'll have her back." He winks at me. Then he starts to lead James out. James tries to pull his hand away, but Rory hangs onto it. James ends up following Rory. And hanging his head down, trying not to be seen.

Once he's gone, Jennifer tells me she'd never thought I'd make James go out with a man. "That has got to be so humiliating for him!"

"And come curfew, Jessica will understand things from the woman's point of view!"

"Oh, yeah! He's gonna do that. Rory is kinda cute, too..."

"He is. I'm sure Jessica is about to discover that Rory is also bisexual." I smirk widely.

Jennifer blanches and glares at me with disbelief. "Oh, Lordy, James is gonna die when he figures that out!"

"Aw... I wanted it to be a realistic date for her!"

Chapter 04: A Happy Ending

Jennifer and I decide to go out for supper. Then, I see another look of horrified shock on her face when I send Sophie to fetch her leash. I clip the leash to Sophie's collar. Jennifer can't stand it another second. She asks "are you seriously going to make her go out on a leash, like a dog?"

"Of course not!" I tell her firmly, but with a little giggle in my voice. "I'm taking her out leashed like a slave! My dog never gets leashed! Lilly... where are you, sweetheart?"

Lilly comes trotting out of my bedroom. Slowly and lazily. She's a four-year-old pit bull. And she suffers from Breed Dysphoria - she's a toy poodle trapped in a pit bull's body. Despite her breed's reputation, Lilly is the most gentle dog I've ever met. She's mostly black, but with a good bit of white to her fur, especially on her face. And she is adorable! She's my "foster dog." She actually belongs to an elderly man two floors down, but he spends a lot of time in the hospital, and when he does, Lilly comes to my realm. Lately, she's been spending almost all of her time here. I suspect, sooner rather than later, it will be all of her time.

She trots out and sits right next to Sophie. She just glances at Jennifer, the unknown lowly human in the house. Then, Lilly swats the kneeling Sophie on her thigh. It's a decent swat, for a dog. Sophie gets the hint. "Yes, my Princess," Sophie humbly answers. Then she pets Lilly. And Lilly smiles. I think. It definitely looks like a smile.

"Does she bite?" Jennifer asks with a touch of wariness in her voice.

"Only hamburgers," I reassure her. "But she is very demanding about getting attention from people. Luckily she has Sophie well trained to pet her on command."

"I see that." Now there's a bit of giggle in Jennifer's voice.

We head for another of the little places along Dauphin Street where I live. It's a quieter place, one that serves good food and foregoes the music, dancing, and partying. And it's another of the places where I'm known. Another of the places where they're used to the leashed Sophie. Nor do they question anything when I get two meals to go, a grilled chicken breast for Paige (whom I never take out anywhere - she's too skanky!) and a hamburger for Lilly. Plus they know me so well they know the hamburger is for Lilly. They add an extra patty to it for her. Lilly will like that. And it won't ruin her appetite. She'll still eat the fries and veggies that come with, too. In fact, she'll eat anything except for dog food. But I've never tried to give her dog food. Lilly eats what everyone else does at my house. And loves it. She'll even come to the table and eat off a styrofoam plate without making a mess. I know, I spoil her!

When we return home, Lilly is waiting at the table for her supper. Sophie serves it to Lilly, just as if Lilly were a person. Except that she sets Lilly plate on the floor instead of the table. Then Sophie takes Paige's plate to her.

Jennifer and I just chat to pass the time while James is out on his date with Rory. As time goes by, Jennifer slowly changes her mind. She decides that James is getting a very good lesson. She only wonders how the date is going. We agree that it can't be going too badly, or Rory would have brought James back early. And Jennifer decides that maybe after spending an evening in heels, James will stop trying to get her to wear stilettos for him. Those are not comfy!