A Shared Lesson

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.

Session Date:

6. February 2021

This Story Released:

25. February 2021

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 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 01: Unwrapping My Presents

When I play with more than one toy, I like to mix up the ages of the toys. To put a young woman with a middle-aged man, or a young man with a middle-aged woman. Or a young woman with a middle-aged woman, a young man with an older man. It's a partner they never would have imagined choosing for themselves. It keeps the toys a little bit off balance.

I've been lucky in finding toys. It seems that there are any number of middle-aged toys, of both genders, who find it enticing to play with a much younger Domme. Younger toys seem to be more interested in serving someone their own age, someone who might understand them better in their minds.

So far, I've kept one 18-year-old high school senior in my toy box. Last year it was Paige. This year it's Joey. I don't have a rule, or a limit, of one. It's just worked out that way.

But every year I get a number of other high school students asking me if I'd consider playing with them as well. I guess it's from sending my toys to school with their collars on. That nicely advertises their status as my slave. I also require my slaves, the ones privileged to wear my collar, to always answer every question they're asked honestly, although there are some exceptional questions they're allowed to respond by saying they won't answer. It has my slave telling everyone that she's my slave. There's no way schoolgirls won't ask a million questions when a classmate shows up wearing a collar!

They come to me in different ways. Some find one of my email addresses somewhere and just message me. Most find a mutual friend of my slave to introduce them and then quietly send me a message through my slave. A few others some other way, such as through one of my other friends. No matter how they come to me, the first thing I do is check to make sure the person is over 18. I never take their word for it, either. And if I can't independently verify their age, I don't respond to them. That's one of my firm, never bending rules.

When I do answer them, I usually give them one chance to catch my interest, and that's not so easy to do. But if they manage, I usually tell them that their parents have to contact me, and when they do, they'd better know what's going on. I'm sure it makes for an uncomfortable conversation. What teenager wants to tell her parents anything about her sex life? More so when there's some kink to it. It nicely weeds out most of the ones who are more playing around than serious.

That's how Gretchen came to me. She doesn't go to the same high school Joey does, but they both have a mutual friend. Gretchen finagled an introduction to Joey, then dropped enough hints until Joey finally, and with my permission, gave her my email. Gretchen said all the right things. And she's pretty enough, meaning most guys would gladly be seen in public with her. None of which sets her out from the herd, albeit a fairly small herd.

When I told Gretchen that, since she lived in her mother's house, her mother would have to contact me, it was a couple of days before she did. a couple of days during which I utterly ignored Gretchen, not even acknowledging that I'd gotten the emails she sent me. Finally, Tracy, Gretchen's mother emailed me. That one I answered.

It didn't take me long to get a good picture of both of them. Gretchen sounded slightly insecure and slightly shy. But her interest sounded honest. As if she wanted to serve someone, not just play around and earn herself a reputation as a fun girl. Tracy came across as a rather average middle-aged single mom. By day she's a receptionist at a health club. Not the best paying of jobs, but enough for her to keep Gretchen eating. She seems to have an average social life, dating, but not especially serious with her boyfriend.

For Gretchen's first session I required Tracy to "deliver" Gretchen to my apartment. I didn't exactly tell Tracy what that would involve lest she slips up and warns Gretchen. Tracy was only slightly reluctant when she agreed. And more reluctant when she got here and found out what "deliver" meant to me. It meant that as soon as they arrived, Tracy was asked to remove Gretchen's clothes for her, not to allow Gretchen to do it herself. Once Gretchen was nude, Tracy had to bind Gretchen's hands behind her, then walk her across the room to me. And then Tracy was sent away, taking Gretchen's clothes with her.

A few hours later, after Gretchen had learned her lesson of the day, Tracy was allowed to come fetch her. When Tracy returned, Gretchen served us both coffee while I told Tracy the very basics of what Gretchen had learned. I did that to humiliate Gretchen. What teenager wants to kneel and serve coffee while her sexuality and body are openly discussed, and she's excluded from the conversation? Then Tracy was allowed to dress Gretchen in fresh clothes she'd been told to bring, and take Gretchen home.

The second time Tracy delivered Gretchen, I arranged it so that Tracy would arrive just before Gretchen finished her lesson. When Tracy arrived, Gretchen was finishing up with a nice, and rather graphically enjoyable supervised masturbation. Tracy, by my design, walked in on it. She got to see Gretchen standing up, masturbating, while I stood over Gretchen with a crop to ensure Gretchen masturbated my way. Such as by standing still as she did it. Any infraction, no matter how minor, was met with a swat of my crop. It also allowed Tracy to see the intense orgasm Gretchen had. And that nicely humiliated Gretchen.

After that session, I got a few emails from Tracy that I'm sure Gretchen still doesn't know about. At first, Tracy just asked a few questions about the supervised masturbation. They were mostly about the rules Gretchen had to obey, and the techniques she was required to use. Then Tracy started asking more interesting questions, such as if the supervised masturbation usually produced such a powerful orgasm.

After a few days of those emails, I decided to send Tracy a summons of her own. I told her that she was to be at my apartment at 4:30, a half-hour after she got off work, and "all her questions would be fully answered." When Tracy arrived, I met her at the door and told her in a rather firm voice, that it was time for her to learn the joys of supervised masturbation. She wasn't to say a single word, or she'd find herself over my knees with a sore bottom before she could even blink. She was to give her clothes to my slave.

I wasn't sure what Tracy would do. I'm not sure Tracy was, either. It took her a few long seconds to decide. But she stripped. And then, she masturbated, with full supervision. But that's all I asked her to do. Once she came, and it was a strong climax, I had Sophie return her clothes and sent her on her way. Gretchen never knew it happened.

After that, Tracy kept emailing me, begging me to never let her boyfriend, Jeff, find out about it. Or anything else. Jeff doesn't even know that Gretchen is serving me, and Tracy definitely wanted it to stay that way. She was afraid of how Jeff would react.

When Tracy delivered Gretchen for the next session, I didn't let on that Tracy had been here without Gretchen. I kept that our little secret. I just kept Gretchen for a long session. And taught her a few tricks between using her for my amusement.

Tracy still thinks Jeff is ignorant of me. He's not. I decided to track him down. It was easy. Tracy had told me enough about him that all I had to do was show up at the car dealership he worked for and introduce myself. At first, Jeff was shocked. That didn't last long. Then he was slightly interested and amused. I'm sure he has some nice images in his mind of Tracy doing some very kinky things - with him.

I asked Jeff, directly, if he wanted me to leave Tracy alone. I didn't get a straight answer from him. So I ask him if he'd care to have some participation, not necessarily playing himself. Maybe just seeing something. Maybe joining in, such as providing a cock for one of Tracy's lessons. He said he'd be open to that. And he said he'd keep this meeting a secret between us. I believed him.

Today is supposed to be Gretchen's fourth session with me. By now she's learned all of the basics that a good slave should know. Now I can start with the more intense teases. The ones that will be more amusing to me.

It's a Saturday evening. I'm Jewish and fairly observant, so I do keep the Sabbath. It ends at sundown Saturday, so I always schedule my Saturday sessions for after sundown. That's not too late this time of year. As always, it's Tracy knocking on the door, Gretchen waiting demurely at her side. I send Sophie, my live-in slave-girl, to answer the door and show them both in.

By now, Tracy has come to expect being told to undress Gretchen and bind her daughter's hands for the session. Whatever the session might have in store for Gretchen. Tracy will hand her nude and bound daughter over to me to use, without having a clue how Gretchen will be used.

Gretchen has come to expect it as well. And to accept it. But she still doesn't like standing there still and silent as her mother takes the clothes off of her. It does nicely remind Gretchen that her body isn't hers to hide. It's mine to flaunt, when, where, and how, I wish. That I will decide when, and how, Gretchen's clothes come off. And that Gretchen has no say in it. Nor do I care how she would prefer it done. Her place is to accept whatever I say.

Gretchen is a fairly petite woman. She's 5'2" tall and 112 pounds. I know. I've fully measured her body, just as I do with any toy that going to be hanging around in my toybox.

Gretchen is also a rather plain girl. She's pretty enough, in that girl-next-door way. To me, she looks like a typical girl, not a cheerleader or beauty queen. But she does have a certain sultriness to the way she looks. It's kind of a "librarian" look. Not really nerdy, though. More... bookish and reserved.

She has dark blond hair that's mostly straight as it hangs down to the middle of her shoulder blades. Her hair has just a touch of body to it. Mostly it's fine, almost silky, with a very slight wave to it. It frames a face that I wouldn't call either rounded or ovalish, but somewhere in between the two. Its face with defined features, but also with soft, gently rounding, lines to it. She has pretty green eyes, behind "frameless" glasses with long, oval-shaped lenses that have straight edges to them with rounded tops and bottoms. She has a slightly long and wide nose with soft lines and no crisp angles to it. And she has a mouth that's moderately wide, framed with a pair of light pink lips. Lips that are full, plump, and delicately soft.

For today, Gretchen has dressed casually, as if she were going to school. It's an outfit I'm sure she's worn to school countless times before. She has on a pink button-down sweater with long sleeves. she has on relaxed-fitting faded jeans. She has on sneakers. I'll presume she has socks, a bra, and panties on underneath.

Tracy kneels down and starts by taking Gretchen's shoes and socks off. She always does, leaving Gretchen as much modesty as she can for as long as she can. I think most mothers would. It leaves Gretchen's small feet bare. Sophie gives Tracy a brown paper grocery bag to put Gretchen's clothes in. Tracy doesn't bother folding them up neatly. By now she's learned that these clothes will be going straight into the wash anyway. When Tracy returns, she'll have to bring fresh clothes for Gretchen. Even fresh shoes. If Tracy tries to bring anything that Gretchen has on now, I'll take it and Gretchen won't get it back. It will go to the shelter for abused women, a favorite charity of mine, and one that can always use donations of nice things.