A Sissy's Date Night

Author's Note:

Mistress Pepper and Sophie are "anonymized" versions of me and my slave-girl. The real me. All of my stories are (or should I say will be) my memories of a session with a sub. Thus, they are true stories. Only in this version details have been changed to protect the sub. I do live in Mobile about 10 months of the year (the remaining two I spend in Nizhny Novgorod, Russia, where my father is from and lives), and almost all of my subs live in Mobile or a bordering county. I'm originally from Baldwin County, next door to Mobile. I moved across the bay to attend USA. As is/did Mistress Pepper. But I'm not a blond. And you'll most definitely have to guess at my bra size!

I'd also like to thank my online friend "sissy doll" for volunteering his identity to replace the identity of the actual sub who experienced this "Date Night."

*****

Session Date:

18 September, 2020

This Story Released:

06 October, 2020

A Sissy's Date Night

Prologue:

In case this is the first of my stories you've read, there are a few things I've skipped over in this story since there are several other stories I've written about this same sub. I tend to write a story after almost all of my sessions with my toys. But I publish very few of them online.

My name is Pepper Rodgers. I'm a 19-year-old Domme, living downtown Mobile, Alabama. I have a decently well-stocked playroom in the second bedroom of my fourth-floor apartment (most of my neighbors are corporate types who aren't always around, giving me a lot of privacy, even in the halls and elevators). I also have a decently stocked toybox. I prefer my toys to be older than I am, around 30-42 years old. I prefer men for myself, however not for my toybox. When it comes to toys, I find women and couples to be far more amusing. Single men tend to be needier, and often too clingy. But that doesn't mean I don't have a few of them in my toybox. I do. They just don't have the same chances of getting there as couples and single women do.

I'm petite. Actually more "tiny" that petite. I'm 5' 1.75" and 91 pounds. I'm not bony, though, I've curvy, like a small-sized woman. I have blond hair down to my shoulders and blue eyes. Oh, and my chest is the only place I'm not small. I'm a 32-D, and I'm very pert. Which makes me popular with the boys.

I'm also slightly bisexual. I'm attracted to men, not women. I would never choose a female partner for even a date, let alone for sex. But I'm not opposed to masturbating with a female toy. Sophie happens to be my favorite sex toy to pleasure myself with. Her tongue has two big advantages over my vibrator: one, it's very delicate and tender. Two, no matter how much I use it, its batteries never die at the worst possible moment! It's better than fresh bunny batteries, it just keeps going until I want it to stop. And I don't even have to hold it in place!

When I want sex I never use one of my toys. I never allow a toy touch, or even see, all of me. And I never bring a toy to my bedroom. Nor do I chose a woman. I pick a man, usually one I find in a club or cafe, or wherever. I flirt, dance dirty a little and if he meets my standards, I ask if he's interested in a one-time-only, no-names-exchanged, hook-up. I've never been turned down.

I have a few standards for my hook-ups. I never pick a guy I know or even just see around. And I insist on a cock between 7 and 9" long and 1.5" across, plus or minus a small bit. I won't touch a guy who isn't circumcised, either. I hate the way the foreskin feels inside me. I want to feel that fat head. The dirty dancing gives me plenty of time to tease a guy hard and feel for myself what he's got. It's the only way not to be disappointed. Guys always lie about their equipment!

Sophie is my 19-year-old live-in slave-girl. She's slightly petite at 5'4" and 119 pounds. She's pretty, too, with long honey-blond hair, green eyes, and a 34-B chest. Sophie is extremely devoted to me. So devoted, and so happy as my slave, that despite not being attracted to women, she's a virgin with men. She serves and pleasures only me, and those I give her to. And while I use her, even with my male toys, I won't allow any man to touch her pussy or penetrate her bottom. Those are mine. Only mine. I've owned her since she graduated high school, but I've known her longer. Since about two months after her 18th birthday, which was also about two months before she finished high school.

I have three BFFs, (Isabelle, Reagan, and Ellie) none of whom are into my little games. But all of whom occasionally creep into my stories. After all, they are my BFFs so they tend to be around. Luckily they're not offended by anything they happen to see. They're just not eager for me to put on a show on their account.

I also have a circle of five other women friends, all of whom are Dommes as well. Andrea (26), Janelle (35), Colette (39), Diane (43), and Olive (44). we usually get together every couple of weeks for coffee and a little chat about who's doing what to whom lately. We sometimes share, or loan, our toys to each other, but not that often. Sometimes we do a favor for each other, such as providing something different for a toy. Mostly we do what girls do: we gossip.

Chapter 01: The Sissy

I know I'm in trouble the minute my phone rings. It's late morning and I'm between classes. Actually, I'm lounging around on some grass in front of the building my next class is in, sipping an iced tea and scanning over a textbook. Boring! But essential. If I have any hope of medical school after nursing school, I have to keep my GPA up. Those medical schools are just so picky! And I've never "not made the cut" for anything in my life. No way am I starting now. And I'm not going to medical school in Grenada, either.

It's my friend Andrea calling, and that's a big neon billboard of trouble on the horizon. She knows my class schedule. She never calls during the mornings. Besides, if I remember her schedule right, and that an "if" only slightly larger than Texas, she should be working. She's a flight attendant. According to her, flight attendants stay very busy during a flight, too. I know they have on all the flights I've taken.

She tells me that she is indeed "working." She's "high." That's her word. And in this case, it doesn't mean what it does on campus. It means she's at cruising altitude. It means there are people waiting on their minuscule bags of peanuts! Yup, I'm in trouble. Andrea definitely wants a favor.

She does. She doesn't waste much time getting to the point of the call either. Maybe someone is getting insistent for his peanuts? All three of his peanuts, if her airline is anything like Aeroflot, the airline I usually fly to Russia.

She tells me very briefly about her "boss of the day," the aircraft's purser or head flight attendant. By briefly I mean little more than her name is Jennifer, Andrea has known her for a while now, and she a "great gal." Then Andrea asks if she can Jennifer my number. Jennifer is in serious need of a favor, and Andrea doesn't want to do it herself. She says she'd just feel so awkward since she works with Jennifer.

I give Andrea my usual answer, the one Andrea already knew I'd give. She can give Jennifer my number, and I'll talk to her, but no promises that I'll actually do the favor. Not until I'm certain what I'm getting myself into. I think Andrea already knows I'm going to do it. I can hear it in her voice.

Jennifer calls me 90 minutes later, magically catching me during a break in the class. Catching me just as the machine is filling a cheap paper cup with lousy coffee for me, too. But I go ahead and take her call. I figure I might as well find out exactly what she's after. If it doesn't interest me, I can just get rid of her and be done with it.

She's bubbly, to say the least. She's hurried, talking fast, as she tells me that their flight is on the ground in Atlanta now. She has about ten minutes before the next "herd of cattle" board for the run to Cincinnati. If I remember right, that's the time when they're supposed to be cleaning the plane up. Not locked in an airplane restroom calling me. But I'm not her boss, so I don't care. And apparently, the Captain, who is her boss, doesn't either.

She tells me a story about a flight of hers two days ago that was canceled for violations of the no-smoking rule. Apparently, the right-hand engine refused to stop smoking for takeoff. Engines! With no flight that day, she went home. She walked in on her husband and his friends "hanging out." However, all of them, including her husband, seemed to have a rather misogynistic attitude. All they could talk about was how "easy" women have it. Men do all the work in dating, in life, in general. Women are just along for the ride.

They shut up when they saw her. Afterward, he claimed he was just trying to cheer up one of his friends who just found out he was getting a divorce. She doesn't really believe him. Mostly because of a few other things he's said recently.

She wants him to be taught a lesson. She wants him to learn to appreciate a woman's life, and understand that he has things backward. It's us women who have it hard! She half-teasingly told him that she was going to send him to Andrea, who would certainly teach him a lesson he'd never forget. He said he'd go. Which kind of surprised her a little, she had thought that he'd object to it. Seriously object. I suspect there's more to it than that. Like that she told him if he didn't learn his lesson, he would be the next of his friends to get that mid-life divorce. But if there is, she leaves that part out.

She says that Andrea "avidly recommended" me. That Andrea assured her that I could teach him a lesson he'd never forget that would ensure that he truly grasped the intricacies of womanhood. And she would be forever grateful if I was willing to.

I tell her that I could do that. I could make him appreciate womanhood as only a woman does. However, before I agreed to, there are two conditions. First, he must be completely willing to learn his lesson. Second, both of them have to agree that there are no limits to what I may do with him. From the instant he arrives here, he'll belong to me, and I may do, or have done, whatever I fancy with him or his body. And I won't care what he wants, or likes, or detests. Nor will I care what she wants him to do, or would never want him to do. He's mine, not hers, for the duration. And it's going to be a very "in-depth" lesson.

She eagerly agrees and assures me that he will as well. She agrees so eagerly that I wonder if there's more going on than I know about. It wouldn't be the first couple to want to come to me to "spice up" their sex life. But, since she knows Andrea so well, at least with her I think she has a pretty good idea of what she's getting them into. At least in general.

Since it will amuse me, deeply, to teach a man not to take women for granted, I agree to teach the lesson. She assures me that once she's returned home, to Virginia, she'll get both of their schedules and see when she'll be in or near Mobile again. That night she calls me again with some dates, and we agree on one a week and a half later.

That was a week and a half ago. Now it's 4:00 on a Friday afternoon, and just as promised, Jennifer is knocking on my front door. As I always do, I send Sophie, my live-in slave-girl, to answer the door. She shows them in, bringing Jennifer to me on the sofa, and offers her a coffee. She leaves James, her husband, standing along a bare wall and waiting.

I decide that I like Jennifer almost immediately. Like me, she's a very petite woman. She's just a tiny hair taller than me, our eyes actually level, so she has to be 5'2". She's thin, just like me, too. I'd guess somewhere around 110 pounds. And she's even a blond! She has short hair, though, and I'm pretty sure it's a dye job. I can see just the faintest hints of roots. But she's not as busty as I am. In fact, her breasts look to be rather on the small side. Maybe even a dreaded A-cup. But I'd bet she's a 32, just like me! Only she's older. I didn't ask how old she was. Since this is only a "one-off" I really didn't care that much. I'd guess she's somewhere around 50-ish, maybe on the younger side, but if so not by more than a couple of years.

Jennifer and I chat for just a couple of minutes. We say nothing about any lesson, either. Just a little girl chat, and a touch of gossip about Andrea. While we sip coffee and chat, Sophie humbly serving us both the coffee, we all utterly ignore James, leaving him to stand idly against the wall.

Without letting him see it, I keep watch on him out of the corner of an eye. It's enough. After a couple of minutes, I see him start to fidget lightly. It was preordained. NO one can stand still very long without starting to fidget a little. Especially a man such as James, who is so clearly lacking proper discipline in his life! It makes me want to gift Jennifer a nice paddle for him!

Once he starts fidgeting, I wait another minute or two. Then I just crook a finger at him, "come, your worthless little sissy bitch." I point him to stand at a place where he's facing both Jennifer and me. He comes over a slight eagerness and a slight resignation, in his step. But he stands where I point him to.

"You won't need anything for this lesson, sissy," I tell him firmly. "Perhaps if you asked Mrs. Palmer rather politely she might agree to hold your clothes for you. You may ask her. Either way, strip, sissy." I keep my voice rather detached, as if he is insignificant, yet also firm to, hopefully, let him know that I'm not asking him to get naked. I'm telling him he's about to. I didn't say anything, but if he doesn't ask his wife to take his clothes for him, I am so going to make sure some of them get "lost." He shouldn't leave them just lying around my apartment, should he?

He must have caught the message. I strongly suspect that Andrea has given him a little primer. Or rather given Jennifer one to give him. The little things, like that I never ask a sub to do anything. I tell. And that my inner imp likes to come out and cause mischief. Or maybe Andrea just sent him a stern warning to follow my instructions. And take any hints I might give.

"Mrs. Palmer, would you please hold my clothes for me?" He turns and asks Jennifer. It's far from polite. At least by the standards appropriate for a sissy bitch like him.

I don't give Jennifer a chance to answer. I spring to my feet and quickly slap his face. It's not my hardest slap, but it's good enough to sear a tiny pink handprint on his cheek. It won't take but a couple of minutes to fade, but I don't care about that. I just wanted to make sure I really have his attention. His full attention.

It works, too. His head turns quickly to face me, a look of absolute shock on his face. I can see some surprise on Jennifer's face, too. But not nearly as much as I see on his. Hers looks to me to be more the kind of surprise that says she thought his request was polite enough and wonders what he's getting slapped for.

I don't give him a chance to say anything, either. "I said politely, sissy!" I snap without raising my voice. "I didn't even hear 'Ma'am' once! And you're standing! That is so rude of you to stand over Her while you beg Her for a favor. I should just throw those close in the trash where they belong. But I'm so nice, I'll give you one more chance, sissy.

"Get. On. Your. Knees... now try to ask Her politely. Remember, you are nothing here. You are just some stupid sissy bitch here to amuse me. Stop pretending you are an actual person, like Her. People matter. You so do not matter!"

James gets down on his knees. I don't give him the chance to ask her. Instead, I take my crop and swat his knees lightly with it. Very lightly. Just enough to keep his attention focused on me. And maybe enough to get him thinking about how my crop would sting him, should I actually use it on, which it appears I am not just willing, but eager, to do.

"Spread those knees, sissy! Didn't you see my slave-girl spread hers as she knelt? Do you think you're better than a lowly slave-girl? I have news for you. You're not better than a slave. You are lower than a slave. At least that slave-girl is capable of doing something that pleases me, like serving my guests coffee. You can't even get on your knees."

His knees almost fly apart. Another little tap to their insides urges him to spread them even wider. This tap is just slightly harder, still not hard enough to really leave a mark, but enough for him to know the swats are getting harder each time. He doesn't risk a third. She spreads his knees to their widest.

I swat his ankles, just above his shoes, and tell him to get his feet in line with his knees. Then I swat his bottom and tell him to sit back over his heels. A swat on his back, between his shoulder blades, gets his back up straight. "See, sissy, you can kneel like a proper bitch! And it only took me three times as long to teach you a trick as it takes me to teach my dog a new trick! I guess we can see who is smarter, can't we? Now, be humble and ask very politely."

"Miss Palmer, would please be so kind as to hold my clothes for me, Ma'am?" He asks his wife. That, I'll allow. It was so much more humble! She quickly agrees to hang on to them for him.

He rises to his feet and starts taking his clothes off. He doesn't seem too shy about getting undressed, but like any normal male, he saves his boxer shorts for last. When it's time for those to come down, baring every private thing he has, he hesitates slightly. Then he slips them down with a deep breath. He gives her a pile of clothes.

Or tries to. I stop him, scolding him for being a filthy slobbish sissy. I tap his hands with my crop, very lightly, and make him neatly fold everything. Then I have him kneel and offer her the clothes atop his upturned palms. I teach him that his palms are to be flat, even with his nipples, and six inches out from those tiny nubs.

I can already see it on his face and in his body. He's getting exasperated. He's only now realizing that I have a specific way I am going to make him do just everything. That he's not going to have a choice. That I don't care what's comfortable for him. Or uncomfortable. Or humiliating. I only care that he does what I want, exactly how I want. As if he's just a doll in my playhouse. Which is about what he is here. But I can also see the edge of nervousness starting to creep onto his face.

Jennifer takes the neat pile of clothes and sets it on the table in front of her.

He starts to get back up to his feet now that she's taken the clothes from his hands. I swat him atop his head. He stays on his knees. "You haven't been dismissed, sissy," I tell him firmly.

"You're dismissed," Jennifer tells him.

I allow him to stand. As soon as he's on his feet, he stands with his hands together, casually, but also covering his cock. I swat those hands and scold him yet again for not having them at the small of his back. "If I had a dick that tiny, I'd want to hide it too!" I laugh, "But sissies don't have any modesty here! Or privacy. Or shame. Or... well, anything! Only what little I deign to give them, and I haven't given you anything."

He puts his hands behind his back. It leaves his entire naked body on shameless display. For his wife. For me. For my slave. All of whom are dressed. He's the only one naked.

He is definitely not my type. Not even the type that might earn a place in my toybox. But, for a one-off, I guess I can make do. Besides, this is a favor for Andrea's friend, so the normal guidelines go out the window.

He's decently tall, around 5'11". Jennifer warned me that James was a "little overweight." He definitely qualifies. I wouldn't put him at the level of fat, but there's no disputing that he's heavier than he should be. I guess he's close to 250. About 50 pounds more than he should be. About 60 pounds more than I'd allow him to be if he were my property. I'll have to have a little talk with Jennifer. Clearly, she doesn't know what immature creatures sissies are. They need constant supervision! At just everything!