Day and (Second) Date

I don't have her wear any other jewelry, or even earrings; I'm generally not a fan. If someone's on the lookout for shiny things, I want them focused on her neck. I know Mandy will appreciate that too. While Melinda and I are conversing like adults, Mandy will be working herself into a humiliated sissy tizzy, wondering how many people realize that she's not a real woman, and not even a real person.

Ah, right -- a fresh anal plug. It's a smaller one, in a classic shape, but it's clear glass -- very heavy. It won't be stimulating her sissy spot, but she'll be feeling it in another way.

That leaves the makeup. It takes forever, and I'm of no help. There are certain lines neither of us want to cross. I don't want to be good at makeup. I want to be able to compliment it or criticize it once it's finished -- nothing more, nothing less. I down a single shot of bourbon and check Mandy's site while I wait, hoping to see a last-minute comment from an unfamiliar user name. No such luck.

Mandy does a good job of her makeup tonight, and I'm glad. The night's not really about her, or her humiliation. It's a real date. I'm hoping to impress Melinda and get her to come home with me. Unless she's a complete disaster, I'm sure I'll want to fuck her. Mandy's the prop tonight, not Melinda. Still, my sissy does make for a pretty prop. She very well could've been my date tonight, if she weren't a sissy slave who needs to be reminded she's inferior to real women.

"You look very pretty, sissy," I tell her. "I'm sure most people tonight will assume you're our submissive unicorn, and that we'll be double penetrating your pussy and your ass after dinner."

She blushes through her makeup, clearly enjoying the beautifully backhanded compliment. She doesn't quibble over the details -- like, say, all the other three-person sex positions we might choose instead.

"Thank you, Master," she says. "I hope I please your date too."

"You'd better," I say casually. I snap my fingers and head towards the front door.

Oh, I almost forgot: I made Mandy change her panties. She's wearing a lacy, bright-red thong underneath her black-and-silver ensemble. Don't ask me why, but underwear that doesn't match the outerwear is just hotter to me for some reason.

Okay, maybe ask me why: maybe it's because I love the idea that once you've seduced your date, brought her home, and gotten her clothes off, you might be surprised by what you discover underneath.

******

Melinda arrives to the restaurant just about when we do. We only have three minutes to spare, so we skip the formalities and head inside. By then, she's sized both of us up, and I already know that she's willing to have sex with me, provided I don't screw anything up too badly during dinner. That's just how it works for guys like me. Women see us -- especially in a nice suit, at a nice restaurant -- and they make the call. Other guys have to put in weeks or months of effort, only to disappoint the occasional woman they do bring home once they're in the bedroom. My hard work is at the beginning: screening for women who are okay with me owning a sissy. It narrows the dating pool a bit, but not by as much as you'd think. You'd be surprised what suddenly becomes 'intriguing' instead of 'disgusting' when a hot, well-off guy is the one doing it. It helps that Mandy's technically male. It helps a lot.

Melinda's thoughts on Mandy aren't quite so transparent. At a guess, she's impressed -- more so with the master because of the sissy, rather than with the sissy herself. That's as it should be. Just between you and me, saying that Mandy 'passes' is an insulting understatement. If Melinda didn't know the truth, she'd likely be spiraling a bit. Mandy's six years younger than her, and, while Melinda's an 'office nine,' Mandy is a 'sissy fifteen.' I'll spare you the conversion metrics; Mandy wins.

Beyond that, Mandy is obviously in love with me. Her submissive nature doesn't merely radiate; it's music through a loudspeaker. Every man who sees her tonight is going to know that I fuck her any time, any place, and in any way I want. They're going to be green with envy. Most women will know the same, and, well... let's not worry about the spread of reactions. I'd hardly do their 'superior emotional intelligence' justice in a few lines, right?

Melinda's different; that's why we're on a second date. She sees Mandy, and respects the job I've done molding her into a passable sissy slave. Some people are threatened by a potential partner's sex toys. Mature people aren't.

We take our seats, and I set the tone for the meal. When the waitress comes by to push booze, I defer to Melinda. She asks if I have an inkling, and I reply that I'm considering the filet mignon. She orders a bottle of red, and I keep my poker face on. I don't know shit about wine, and I don't pretend to; I just elide my ignorance. 'Red with red' sounds familiar.

The waitress is torn, and I know why. She's supposed to card Mandy -- and, hell, maybe even me and my date - but this restaurant is the kind of place where prickly people are looking for an excuse not to tip. I come to her rescue.

"My business partner," I tell her, nodding towards Mandy, "won't be having any tonight. A bottle of sparkling water as well, please -- and, I hate to trouble you, but could you bring her some lemon slices and a few maraschino cherries? She likes a hint of flavor."

The waitress smiles, and Mandy beams. Nobody gets carded.

The wine and water come out quickly, and we slip into some easy chatter while we sip at them. Melinda's happy to sum up her own career succinctly: sales and marketing for yet another software development firm. Thankfully, it's not in any kind of direct competition with mine; there'd have been paperwork, seriously. We swap stories about subordinates, and make a few wry comments about the painful truth of various corporate stereotypes.

Mandy stays quiet at first. She knows not to speak unless spoken to. Melinda very quickly breaks the ice with her, though. She pushes Mandy on all the financial and technical details of her 'business venture,' constantly dancing around the elephant in the room. Mandy vacillates wildly between confident and flustered; if she's only pretending to let Melinda push her buttons, it's quite the performance. I lean back and enjoy it. Things are going well. Melinda seems more than just tolerant of the sissy dynamic. She understands it. She's having some fun with it. As impressed as I am with her, she's also impressed by Mandy in turn. My sissy's voice and mannerisms are both extremely feminine, and she maintains them even through a decently-long -- and somewhat embarrassing -- interrogation.

If I were a more traditional master, I'd probably punish Mandy later for putting on airs. There are times during her and Melinda's conversation when she sounds not just confident, but genuinely intelligent and knowledgeable. I'm lazy, though, and I did spend an awful lot of time over the past year nudging Mandy away from being a completely masochistic pain-and-humiliation slut. As long as she understands that her every virtue is thanks to me, and then dedicates them all to my service in turn, I'm a happy master.

Still, I wouldn't be a master to a sissy in the first place if I didn't have some fun with the dynamic. While Mandy and Melinda chat, I scan the room. I don't expect to see many stares -- maybe some glances. My date and my sissy are both pretty enough to warrant them, and a few patrons might wonder if I'm really out on a date-date with both at once. I pick out the grossest man I can find with some kind of an eyeline towards Mandy's face. I'm being uncharitable, I know; really, he's just old. He's eating with his wife, I assume. I glance over to their table just often enough so that he senses somebody watching him. I don't let him catch me, but, sure enough, he gets curious.

When Melinda and Mandy hit a natural pause, I lean towards my sissy.

"You have a fan, Mandy," I say in a low voice, though loudly enough so Melinda can hear me too. "Old man with his wife. Your two o'clock. I've caught him staring twice already. He knows your face. He's seen you online. He's trying to put the pieces together."

Mandy just barely suppresses the natural instinct to look. Instead, she hunches over and turns beet red. Melinda's eyes flash. I grin.

"He's probably pretty well off," I say. "Do you want to go over and introduce yourself? See if maybe you can move up in the world?"

"Or at least offer him a selfie or an autograph," Melinda suggests. "Not for free, of course."

"Of course not," I agree. "What do you think? Is tonight the night? Do you want to open up a new revenue stream? Take him into the bathroom, or meet him in his car? It's probably a very nice car -- plenty of room to maneuver. And hey -- he's so old that you'll probably be able to lick his balls and kiss his feet from the same position."

Mandy's shaking in her seat. She purses her lips; it's anything but sexy. She shakes her head. It's desperate at first, but she catches herself quickly and makes it subtler.

"Do you want me to, Master?" she asks. I credit her discipline. She avoided saying 'no' to me when it might've earned her some extra swats.

I lean back. "No, of course not," I say in a normal voice. I wait for her to relax, then give her a wink. "The back end is an outsourced template, but we worked with the subdev directly to make sure it met our needs."

"Hmmm, makes sense," Melinda chimes in, playing along. "It doesn't seem like the business model demands too many custom features, but it's good to have a point of contact regardless. No such thing as bug-free software -- except for my company's, of course."

Mandy corrects her posture and nods along. The mini-game is over. I probably won't play another one, but she'll be waiting for it the rest of the night regardless.

The waitress returns; Melinda orders the salmon. I order the filet mignon for myself, and a grilled chicken salad for Mandy. They don't call it a grilled chicken salad, of course. They dress it up with half a dozen flourishes and give it a fancy name to justify its outrageous price tag. The waitress betrays just a hint of surprise that Mandy doesn't order for herself, but she doesn't look to her for confirmation. Mandy looks down and blushes a little. That's another few dollars on the server's tip, and she'll never know the reason why.

We manage to keep the conversation going until our meals arrive; it's a subtle test, and the two of us pass it together. Second-date silences still aren't comfortable, so they're best avoided. I mention a few books I've read recently, and let Melinda push us towards television and movies. I don't think any less of her for it, but you'd be surprised how negatively some women react to a man who brings up 'low' entertainment unbidden. It's particularly ironic that I'd care, given how much Melinda knows about my main hobby, but that's just the way it is.

As impolite as it is gawk and make comments about one's date during the date itself, I suppose it would be equally impolite not to fill in a few details in the telling. The lull in the conversation while we eat our meals seems as good a time as any.

Melinda's not bad-looking at all. Her short, black hair is professionally styled, and it strikes a nice contrast with her creamy-white skin. Her hazel eyes are deeply set, making her narrow, hawk-like nose seem even longer. Melinda's wisely contoured the natural shadows that her nose casts around her eyes with some makeup; glasses, I think, may have helped as well, but she's not wearing any. She's given her thin lips some extra help with an understated red shade; prior to the main course, I found myself enjoying the sly smiles they made while toying with my sissy. Now that Melinda's eating, I can see her teeth are white and straight - always a good sign. Her glossy, purple fingernails are immaculate, and her soft hands seem deft. Using a fork and knife isn't exactly a challenge, but you can get a sense.

Her dark-teal dress is sleeveless, but the top of it is quite different from Mandy's. It covers more of her shoulders and collarbones while revealing plenty of skin below her neck, terminating with a hint of cleavage. It's mostly straight down her body, without any poofs or ruffles. It also sports an array of wavy black lines that occasionally threaten to become spirals; there's just few enough that you can't call it a pattern. The black lines aren't quite tribal, nor mathematical or musical. They're elegant and understated. The fabric itself hugs her curves, all of which are ampler than Mandy's, but not to any great excess. The dress ends just above the knees; like Mandy, Melinda's eschewed stockings or nylons tonight.

Honestly, my biggest criticism is the color of the dress. It's a common mistake among professional women. They stray from traditional black, white, or red, and often pay the price. It's a nice outfit otherwise. I appreciate the little bit of her creamy C cups it reveals. I don't stare, but I steal more than a few glances.

My second date with Melinda turns out to be a real date, through and through. We're not making 'fuck me' eyes at each other the whole time. We're not desperate to pay the check and race back to my place. It's a really nice restaurant, and my date clearly wants to enjoy it.

Melinda excuses herself to the bathroom after the main course.

"Do whatever she says while you're in there with her," I whisper to Mandy, "unless you're sure I won't like it."

Mandy blushes again. "Yes, Master," she whispers back, then stands and follows Melinda to the bathroom, just like a real woman would.

When the two of them return, I get the distinct impression that Melinda just gave my sissy a concentrated dose of humiliation. I'm happy I sent Mandy along with her. I don't pry; I'm not going to ask a real woman what she did in the ladies' room. I'll definitely ask Mandy later tonight if I haven't already found out.

We order coffee and dessert; I only order a cup of decaf for Mandy, and she silently declines anything else when the waitress inquires. That's a few dollars off the tip for failing to recognize my authority. Melinda and I both have triple espresso shots and criminally-small slices of double-dark-chocolate cake.

I pay for everything, of course. Reality trumps ideology. I don't make a big deal of it; I just slip my card in with the check and let the waitress retrieve it. I leave her a twenty percent tip. It would've been twenty-five or thirty if she'd better heeded the table's dynamic. She was so close.

We step outside into the cool evening air. The restaurant's lights bathe the sidewalk, and make us a part of a perfect upper-middle-class snapshot. Every noise -- diners, passers-by, even cars -- seems dignified and restrained. It's a nice part of a nice city. I take a deep breath and smile to myself. I just had a good date. I have a good life. I own a great sissy.

I radiate easy confidence, satiated contentment, and zero expectations -- and with that, I pass another test.

Melinda holds up her phone. "GPS?" she asks.

I take out mine and shoot her my address. Halfway to my car, I give Mandy's ass a loving squeeze -- hard enough so I can feel the base of her heavy anal plug. She squeaks, and pulls herself closer to my body.

"Good sissy," I whisper to her. She practically shivers from the praise.

She did her part. If she keeps this up, she might even get a treat.

******

When the three of us get inside, I take Melinda's short jacket and hang it up in the foyer closet.

"Panties on or off?" I casually inquire.

It doesn't faze Melinda. She glances towards Mandy, who's already stripping. "On," she says, after a moment's thought. "I've already seen the cage and plug."

Mandy blushes and almost trips herself. Melinda and I trade knowing smiles. Bathroom mystery: solved. I guess they'd had the room to themselves for a few minutes.

I walk towards my date, and she sends all the signals. We loosely embrace, and kiss for the first time. We take it nice and slow. Mandy's bumbling is our only accompaniment. Melinda's a fine kisser, and she seems happy with my efforts. Our tongues dance a bit, but we don't get too aggressive. My hands wander, but only to relatively safe places for now.

"So, what can I offer you?" I ask.

"Your sissy's mouth, I think," she says. "She can undress me, too."

I can't help but smile. "Of course," I say, "though I must insist she be properly collared first. Leash or no leash?"

"No leash," Melinda replies. "It'll only get in the way."

Mandy's down to her day collar and thong. She gets on her knees. I silently seek permission from Melinda to see to my property, and she grants it with a nod. We untangle from each other, and I walk over to remove Mandy's slim, black collar.

"To the bedroom, sissy," I say. I look over at Melinda again.

The alcohol and food have worked some magic on her. She looks and sounds much less like a put-together career woman than she did an hour and a half ago. Frankly, she looks ready for almost anything. "Lead the way, Q," she says.

There's only like three names it could be. Use your imagination.

Melinda walks slightly behind me, and Mandy crawls behind her. We make our way to my sissy's collar collection. It's well-organized on shelves, though her most expensive ones are clasped around the necks of a few faceless busts that also sport our collection of wigs. I motion for Melinda to pick whichever collar she prefers. Hell, if she wants Mandy to wear a wig, I won't object. She only takes a few moments; she appreciates the pageantry, but wants to keep things moving. I feel the same way. She settles on a thick, white one with "sissy baby" written in faux-cursive lowercase pink letters. It sports a pink, heart-shaped padlock in the front, plus the leash link.

I don't offer the Melinda the chance to collar Mandy; we're not there yet. Mandy gets into her standard kneeling position, and I make quick work of it.

"Thank you, Master," Mandy says.

"And how should she refer to you, Melinda?" I ask.

"'Miss' or 'Miss Mel', I think," my date replies. "'Miss Stein' just doesn't work, does it?"

I shake my head, agreeing. "Those darn 's' sounds all lumped together."

She nods, and Mandy gets back down on all fours. We head to the bedroom, only a few feet away.

"You do as Miss Mel says unless you genuinely believe I won't like it," I tell Mandy, echoing the instructions I gave her at the restaurant. It's master-sissy boilerplate.

"Yes, Master," she replies.

With a look, Mel lets me know I can strip down. "Attend me, sissy," she says. Mandy starts with her heels, and works her way up. Mel does her own jewelry, which I place on a nearby dresser before starting on my own clothes. Mandy does the rest for my date. Once her dress is off, I get to see the matching underwear set: lacy, black cheeky panties and a lacy, full-coverage bra. Mandy hesitates, and Melinda gives her the go-ahead. The bra comes off, and her C cup tits spill out. They're not bad. The panties are next, and they expose a wide, thick, black bush.

Melinda silently dares me to say something. I raise my eyebrows and flash her a smile. You'd have to be an idiot to fail a test at this point, but they just keep testing you regardless, don't they?

I'm down to my boxer briefs. Mandy's back on her knees. Melinda gets her attention with a casual tap on her head.

"Go slide those down for me, sissy," she says. "Slowly."

"Yes, Miss Mel," Mandy says. She gets down on all fours again just to crawl three steps. I appreciate the commitment. She gets up on her knees, and gives me a reverent stare. She gives another to my crotch, then does as Melinda bade her, slowly sliding my black underwear down. I keep my eyes on my date. Her eyes find mine, but after a few seconds, they drift down to my crotch. My well-trimmed pubes come into view, and then my cock -- and then even more of my cock, and then one more dose for good measure. Melinda's hazel eyes widen.