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!

And remember, the names and such have been changed in this version to protect the slutty. Only Princess Lilly appears as herself. But she truly has no concept of shame.

Thanks to my friend Ken for proofreading!

Session Date:

10. April 2021

This Story Released:

16. April 2021

Date Night

Introduction:

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 20-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 20-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.

Paige is my 19-year-old house-slave and slave-whore. It's a role she definitely loves. She lives with me, too. In a kennel, in the playroom. Like Sophie, she came to me during her final year of high school, just after her 18th birthday. Paige does most of the chores around the house, which leaves Sophie free to cater more closely to me. Paige is also my whore. Whenever I need a female body to torment one of my toys, it's Paige's body I use. And Paige definitely doesn't mind it.

Paige is rather lean girl. She stands about 5'6" tall, but weighs only 112 pounds. It gives her a slightly stickish figure, with only the gentlest of feminine curves to her waist and hips. But she does have a pair of rather perky, and slightly pointy, 34-B breasts with wide nipples. She has honey brown hair that's long and curly with green eyes.

I believe in taking good care of my slaves. Including their education. Sophie is now a sophomore at Bishop State College where she's studying to become a vet technician. Paige, a year behind her in school, is beginning her freshman year at Bishop. Before they became mine, both girls were mediocre students, and neither had the grades to get into a four-year university. Now they're straight-A students. I wouldn't accept anything less. Both should easily be able to transfer to USA for their last two years of college and earn degrees that would allow them to actually get a decent job. They might not need to work while they're mine, but I want them to have their education and options down the line.

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.

I get all of my toys through networking. It's almost always either one of the women in our circle who has a toy she doesn't want and offers to point it at another who is interested. Or sometimes one of my toys tells someone, who tells someone, and so on until someone asks my toy to introduce someone to me. Rarely it's someone I don't play with, but who knows what I'm into, who asks me to meet someone. I get plenty of emails inquiring about meeting me, and while I will email and maybe chat with a sub online, I haven't yet met any. I won't rule it out, but meeting online is risky enough that someone would have to convince me before I'd think about it. A girl's gotta be careful!

Most of my stories are from the months I spend in Mobile. I very seldom publish any of the few stories from my time in Russia. That's because Putin's Russia isn't as enlightened as America. Homosexuality is a crime there. And the courts there would deem anything between two women to qualify. However, it's a crime that's not so often prosecuted. Usually no one really cares if it's kept discrete. So while I have been known to play there as well, I've very care who I'll play with. Only those toys that come to me with the most trusted of referrals are considered. And I keep the stories private. I'm definitely not going to advertise what I've done there.

I have dual citizenship. That's a benefit the Russian government bestowed upon me because my father was a junior diplomat at the time. Sophie goes with me to Russia. She, obviously, is an American citizen. She only speaks about five words of Russian, too. But she never leaves my side. And she does wear her collar, much to the dismay of the TSA screeners. That shiny padlock holding it around her neck is not a friend to their scanners. Paige, however, doesn't get to take the trips. I usually leave her with my mom, who enjoys the free house maid she uses Paige as. And, as a Domme, my mom is well versed in the proper care that Paige might need.

Chapter One - All Dressed Up

Here it is, my birthday, and I'm out doing a favor for my friend Colette. Then again, the favor involves one of her toys, and I always enjoy playing with new toys. Plus, Colette did give me an adorable book bag, something every college student gets plenty of use out of, for my birthday. It's a very soft leather. And it's the prettiest shade of pastel green, with a girly white lace trim! I absolutely love it! It even has my initials embroidered on it.

Colette's a soccer mom, and full-time housewife, so she doesn't have so much time to play. She met me for lunch Thursday and surprised me with my present a few days earlier. Then she called me this morning and asked what I was planning to do for my birthday. I told her I hadn't planned anything. I'm sure there's a party or five around campus tonight, it is a Saturday and that's plenty enough of an excuse for a party on campus. I know I'd be welcome at any party, too. I kind of have a reputation for partying rarely, but very heartily. And for bringing amusing party favors with me. Usually on a leash.

Colette told me about Jerry, a 39-year-old married man who is one of her toys. A very naughty toy, too! Colette made time for him last weekend. Like the naughty boy that he is, he got himself in trouble.

Jerry's wife, Claire, likes to watch his sessions with Colette. Since Colette always keeps her clothes on, like me, she doesn't mind if a wife watches everything. The wife isn't going to see anything more than her husband's humiliation. He might be deeply embarrassed and ashamed by that. But Colette won't be. So Colette doesn't mind.

I didn't get all of the details, but I got enough of them. Colette had him sitting in a chair with his knees spread wide and his hands resting palms up on his mid-thighs. Oh, and with a vibrator in his bottom, vibrating away eagerly. She was scolding him for being too horny. Since a scolding is a light punishment, he was required to keep his cock from getting hard during the scolding. He managed to behave for about two minutes. After that, his cock was sticking up rock hard.

His punishment was something that I would have handed down. Until his next session with Colette, every night he was required to masturbate for a full fifteen minutes. Without cumming. He was to invite his wife to watch him play with himself. Then, if Claire wished to, she could text Colette and ask for him if he could have permission to cum. She didn't tell them, but I'm sure they knew anyway, that permission would rarely be granted.

Claire wasn't required to watch him, but he was required to invite her to watch. Nor was she required to masturbate his cock for him. He wasn't allowed to ask her for that, either. Not even a hint. But she was allowed to masturbate him, instead of making him do it himself, no more often than every other time. And then, only if she first tied his hands behind his back. It was her choice. If he so much as dropped a single hint that he preferred her to do it for him, from then on he would be doing it himself.

Colette didn't want to leave Claire untended for the duration of his punishment, so she also decreed that Claire was allowed full use of his mouth. Whenever, and for however long, she wished. She attached only one condition. After using her husband, Claire was to ensure that Jerry didn't touch his cock for a full hour after his erection faded. And if he got hard again during that hour, the time started over once he was soft again. And Colette explained that she was very strict in her definition of "touch." any kind of contact at all counted. Even just an accidental brushing. Anything. Absolutely no touching his cock at all. Not with his hands or anything else. But he is allowed to dress. As long as he dressed without touching his cock.

He managed to last all the way until Thursday. In those short few days, Colette hadn't yet felt that he deserved release. Duh! I mean, it was only a few days, and he was so naughty! What was he thinking? He begged her for relief. He even begged until he cried. Even after Colette said no! He cried about how horny he was and how badly he needed relief. See what a bad boy he was?

Colette was planning to visit him again soon and administer a special punishment for his misbehavior. But one of her kids isn't feeling well. She has four kids, so there's usually something distracting her from her amusements.

She doesn't think Jerry will behave much longer. He's been crying and pleading for his relief too... obnoxiously. He needs a reminder of his place. Sooner, not later.

Colette tells me a little about Jerry. He joined the Navy right out of high school, serving his country for eight years and deferring college. But then he graduated with his BS at 30. He finished law school at 34. He passed the bar. Then he went to work for District Attorney's office. Where he was assigned to prosecute Juveniles. His caseload is mostly 16 to 18 year-olds charged with what Colette calls "felony stupidity." She means things like joyriding and smoking a little weed in public, or selling the occasional joint to a friend. In other words, not exactly the next Al Capone.

He and his wife Claire have two small kids. She's 35. They met in law school, where she was two years ahead of him. Now she's in private practice.

I can't help but laugh hard when Colette names the firm she's with. Naturally, Colette has to ask me what's so funny about it, they have a reputation for high-quality work and are definitely not the ambulance chasers you see on TV. So I tell Colette. I have a toy named Roxanne who is an attorney from California. Roxanne's firm does only one thing, class-action suits, the bigger the better. They have one that's working its way through the courts here in Mobile. Courts that feature juries that are notoriously anti-big-business, and thus award much larger verdicts than average. I'm sure Roxanne and company took that into account when they picked where they filed the suit. Since Roxanne, and everyone else in her firm, isn't an attorney in Alabama, they needed "local counsel" to put his name on the papers. And provide local office space on the infrequent occasions that it was needed. Claire doesn't have anything to do with that case. But one of the partners in her firm does. I don't know if Claire has met Roxanne or not, but I know Roxanne has spent a number of days working out of the same offices. Given the limited number of female attorneys in that firm, or most firms, I'd bet they've talked a few times. Then again, maybe not. Roxanne is a gigantic bitch. The kind of bitch most people avoid rather than get their head snapped off by her. Then kind that I get unbearably hot by humbling and putting on her knees. Whether Claire has spoken to Roxanne or not, I know that Roxanne is never going to mention anything about her time with me.

Colette thought that I would be perfect to fill in for her and administer Jerry's punishment. And to teach him a lesson he'd never forget. She thought it would not be lost on Jerry how young I am. I'm 21, as of today. I look like a college girl. Or one of the girls who Jerry usually prosecutes. Or hires to babysit the kids. Like me, Colette loves role reversals of any kind.

I ask Colette what she has in mind for him. She tells me that she doesn't care. She trusts me. And she knows that whatever punishment I come up for him, it's going to make an amusing story. Whether I write the story, or just tell her, it's going to be amusing.

I ask if there are any limits. There often are with married couples, especially couples where only one of them plays. It's like they've made a compromise. He can play, but he can only go so far. Colette tells me that there aren't. Claire knew that he was a submissive and needed his play when they started seeing each other. She accepted that it would be a part of their life.

Colette tells me that Claire always wants to watch. In Claire's words, she wants to "share the experience" with her husband. She's been perfectly willing to join in as long as nothing was done to her. She hasn't minded taking instructions, such as to stroke Jerry's cock slowly, from Colette, either.

Colette tells me that Claire is very outgoing. Until her clothes come off. Then Claire is very shy. She hates taking her clothes off in front of anyone. Maybe even her husband. She's just that shy about her body. So far, she's been willing to wear a robe and flash her body to Jerry, but Claire has always tried to make sure Colette didn't see much if anything. She doesn't mind being touched, though. As long as her clothes are still on. Nor does she care about giving Jerry a blow job in front of Colette, as long as Claire keeps her clothes on. She'll even talk about sex openly with Colette.

Colette also tells me that Saturdays are their "date night." they hire a sitter to take the kids out somewhere from five to nine. That way, the kids can have fun, and they can, too. Without worrying about the kids interrupting. Their usual routine is dinner out, maybe a restaurant or a club with some music, then home early for a little private time before the sitter returns the kids.

It gives me a four-hour window. Colette assures me that they won't mind if I take over their date night. And that's exactly what I decide to do. I bring Sophie, my 20-year-old live-in slave-girl with me. We park down the street, like little spies, and just watch the house. According to Colette, they both drive Mercedes. Thus, I assume, the Ford minivan, a somewhat older model, in their driveway isn't theirs. And thus it's the sitter's. In about ten minutes, my assumptions are proven true. I see the sitter, a 20-something woman, leading the kids out and helping the little guys up into the van. I watch her back out and pull away.

I pull into the driveway, taking the place the sitter just vacated. I walk up to the door, Sophie following behind me. Sophie carries the duffle bag with my toys in it. She carries my purse as well. She carries everything except my favorite crop, and I'm only holding that because I suspect I might need it almost as soon as the door opens. That means that Sophie has my phone as well so that she can answer it for me if anyone calls. I prefer not to be interrupted during my fun unless it's important. So, as we're walking to Jerry's door, Sophie is sending Colette a text for me. It tells Colette that I am ready to begin.

I knock on the door. As I expected, it's Claire who answers the door. I see a rather surprised-looking Jerry on the phone, coming up quickly behind Claire. I know that he's talking to Colette. The text was Colette's signal. She called Jerry and right now she's telling him what a naughty boy he's been. And she's telling him that she is sending someone to "remind him what obedience is" for her since it's inconvenient for her to do so personally. He is to obey me.

I hear Jerry saying a very fast, and polite, "yes, Mistress," a couple of times as he's hurrying to the door. Then, the phone still in his hand, he freezes when he sees me. Claire was just asking if she could help me. As I'd hoped, I didn't have time to answer her. Instead, I just say, "go on, fuck stick, tell your wife what you were just told. Now."