A Friendly Wager
Other Mistress and Charlotte stories for your enjoyment
Kitten With Benefits
Maid’s Day Off
A Beautiful Night
Charlotte’s Opening Day
Best Laid Plans
Charlotte’s Secret Recipe
Charlotte’s Jazzy Halloween
Tina’s Plea Bargain
The Third Wheel
Charlotte’s Summer Vacation
It’s a Gift
Juliet’s Play Date
Little Miss Charlotte
The events and characters in this story are fictitious. Any resemblance to actual events or persons, living or dead, is purely coincidental.
The main characters in this story are a trio of women in a dominant-submissive relationship. It is safe, sane, and consensual as well as kind and loving. But if this type of relationship is not your thing, you may want to skip this story and find something else to read. I have plenty of nice romances that I have written as well.
I’m hoping you’ve had a chance to read some of our other stories. If not, you’ll want to at least read Girl Friday and The Third Wheel to understand how the three of us got to where we are today.
We all have busy lives, but we do our best to keep things interesting. And usually, it’s my two girls making their own mischief that keeps me entertained.
I hope you enjoy our latest story.
Love and hugs,
“Mistress, do we have a tape measure?”
“Good morning to you too, Charlotte.” I stood toweling my hair just outside the bathroom while Charlotte sat on the edge of the bed, staring at me and blinking against the bright light streaming from the doorway behind me. As usual for most mornings, she wasn’t wearing any clothes.
“Sorry, Mistress.” She hoisted herself up and pressed against me a moment, before puckering up and laying a little smooch on my lips. “So do we have one? I sort of promised Juliet something.”
“Honey, Juliet’s in LA.”
Charlotte just stared at me and blinked again.
“There’s one downstairs in the toolbox, baby,” I said.
Charlotte chewed her lip for a moment, apparently deep in thought. “Don’t we have one of those flexible fabric kinds, Mistress?”
“No, but I think there’s a paper one from some furniture store in my office.”
Charlotte smiled and scurried off while I focused on watching her lovely little ass jiggling.
“What are you measuring, baby?” I called, but she was gone.
I got my answer a minute later when Charlotte came bounding back into the bedroom with her perky little tits bouncing pleasantly and the paper tape measure flopping around her neck. She pulled some slack into the end of the tape and then proceeded to wrap it around my hand.
Her eyes turned heavenward for a moment. She appeared to be engaged in some rather challenging mental gymnastics.
“Mistress, how do you figure out the size across a circle if you know how big it is around the outside?”
“You mean getting the diameter from the circumference?”
“I guess so. I was an arts major, Mistress.”
I grinned. “Divide by 3.14.”
Charlotte nodded and then scurried off again, presumably to find the calculator app on her phone this time.
“What are you up to, baby?” I hollered.
Charlotte poked her head around the doorway. “Juliet bet me I couldn’t fit your whole hand inside me. I bet her I could.”
Now it was my turn to stare and blink.
I had fisted Charlotte’s sweet little pussy on more than one occasion. We didn’t do it all the time, but I really didn’t think there was any question as to whether she could accommodate me.
Charlotte tapped at the screen of her phone. “Two and about…” she mumbled. “Two… Two and a little bit.”
“What’s two and a little bit?”
“That’s how big I need to stretch to fit you.”
“I really don’t understand this bet you’ve got going with Juliet, baby. She does know that I’ve had my hand in your pussy before, doesn’t she?”
“Not there, Mistress.” Charlotte turned toward the door and slapped herself on the butt. “Here.”
She bounded off again while I just stood while a shudder ran the entire length of me.
“What do you want for breakfast, Mistress?” she hollered over her shoulder. “Pancakes sound okay?”
I just stood there, mouth agape, and blinked.
Thank goodness it’s Zoe working today, I thought as I strolled into the Scarlet Letter Adult Book and Novelty store. I was trying to look as casual as I could muster, but I think if that Dave guy were behind the counter today, I would have turned on my heel and walked right back out. Not that I’m sure he wasn’t a nice guy, I just didn’t think I could talk to him about what I came in for. It was going to be hard enough asking Zoe.
“Hey, sugar,” she said. “Long time canlı bahis şirketleri no see. How’d that flogger work out for you?”
I smiled. Zoe had a good memory. “It was great. We had to send Juliet in for cosmetic surgery just to get the grin off her face.”
Zoe chuckled. “Anything you want to test drive today, or are you just browsing?”
I let my eyes wander around the store as I tried to get up my nerve. There were a couple other customers, college kids by the looks of them. I leaned in close. “Butt plug,” I whispered.
I pulled out my phone with the calculator app still up and showed it to Zoe. “This big.”
“Cheese and rice, Charlotte. Maybe you want to start smaller and work your way up.” Zoe turned her gaze toward the back of the store and started walking. I followed along.
“We’ve got this nice set of three here.” She plucked a box off the display and handed it to me. “You can work your way up. Still though, the biggest one in there’s only one and three-quarter inches wide. What are you training yourself for?”
“Yeah, you know, like what are you trying to loosen your booty up for? You’re not tryin’ to get a dick up in there are you?”
“What? No,” I said. “Mistress’s hand. Juliet and I have a bet. She says I can’t do it.”
“Okay, good. For a minute there I thought you might ‘ave switched teams on me.” Zoe put her hand on my shoulder and let out another chuckle. “That’d be a shame. Your mistress is a lucky woman, you know that. An adventurous girl like you don’t come around but once in a blue moon.
“Most of the time we just get college guys in here, like those two bozos. Probably tryin’ to talk their girlfriends into doin’ something they ain’t never gonna agree to.”
Zoe cocked her thumb at the only two other customers in the store who were now standing side by side staring intently at something I couldn’t see, and giggling like fools. I tried not to stare.
“Anyway, you’ll want lots of lube whatever you do.” Zoe handed me a bottle. “Just be sure that mistress of yours knows to go slow and make sure you’re really turned on first. Maybe have her use a vibrator on you. We’ve got a few on sale right now, twenty percent off.”
“She will.” I smiled, thinking about the last time I felt Mistress’s fingers curling up inside my pussy. “Go easy that is. She’s a sweetheart.”
Zoe smiled and led me back to the front counter. I slid my credit card across the glass top while she totaled up my purchases.
One set of three graduated-sized one-hundred percent silicone butt plugs, electric blue in color. Perfect for any skill level, the package proclaimed.
One eight-ounce bottle of lube. Specially formulated for easy backdoor entry, it said. I wasn’t sure what that formula was, but the woman on the bottle sure looked like she was enjoying it.
One six-pack of all-natural herbal enemas, another of Zoe’s professional recommendations, and also on sale at twenty percent off. I was beginning to think it was the annual Spring Into Butt Stuff Sale they had going on here.
And finally, one Melo Aphrodite 2, dual motor, USB rechargeable, waterproof vibrator. Not on sale, but seeing as how I saved so much on the rest, I decided I could afford to splurge. Zoe assured me it was among the best available.
“Have fun with it, sugar,” Zoe said as she passed back my credit card and a rather large black plastic sack overflowing with goodies. “And I hope you win that bet.”
“Thanks,” I said, and waved goodbye.
As my heel struck the sidewalk and the warm May breeze hit me in the face, I got a rather devious idea. I wanted to try one of the plugs. Like now. Standing in a shop staring at shelves full of sex toys has that kind of effect on me.
I would have turned around asked Zoe if I could use the bathroom, but I figured I had embarrassed myself in front of her enough for one day. I kept walking.
Maybe I can stop somewhere for lunch and discretely slip in one of the plugs before I leave. Or should I slide it in before I order, so I can feel it stretching me out while I dine? I felt a warm tingle and a wetness running down the inside of me thigh as I weighed my options.
Walking along on auto-pilot, I pulled out my phone intending to text Mistress to see if she’d be willing to meet me somewhere for lunch. Staring back at me was the calculator app displaying two point something.
Looking at that number brought my mind back to the discrete black plastic bag in my hand, and the items it contained—specifically the array of silicone plugs. The largest of the trio, at one point seven five looked pretty imposing, and that was still slimmer than the number staring back at me.
Was I really going to be able to fit Mistress in?
Yes, I was, damn it, I decided and stopped dead in my tracks, right in the middle of the sidewalk.
After a moment of getting my bearings, I found I was standing right outside my favorite Greek restaurant. Serendipity!
I began canlı kaçak iddaa composing my text to Mistress.
C: Mistress. Two words. Avgolemono and soup.
M: Charlotte. Two words. Yes and YES!
I smiled and pushed open the door to the restaurant.
C: Smelling it now, Mistress. Care to join me?
M: Super busy, baby. Carry out OK?
My smile faded just a little bit. I was really hoping to have Mistress sitting down to lunch while I showed her the box of butt plugs with one missing. Watching her eyes undressing me as her brain whirred with the thoughts of where the missing plug was situated would have been just perfect.
I wondered if she could show enough restraint to wait until we got home, or if she would be forced to take me to some secluded place and have me show her just what I’d done with it. I began to imagine her giving it a little tug—not enough to pull it out, but just enough so that it would peek out, stretching me open wider—and then watch it get sucked back in.
Oh, god. My thighs trembled a little.
“Miss?” a woman’s voice snapped me out of my introspection. “Miss, are you ready to order?”
“Um,” I said. “Um, two soup and salad lunch combos. That’s to go. And… and an order of baklava too, please.”
“Be about five minutes,” She said and rang my order through the register.
“Thanks,” I said. “Oh, and which way to the ladies room?”
After fidgeting through a couple stops on the light rail, with lunch on my lap and only the smallest of the plugs lodged in my heinie, I began to discover some enjoyment in the ordeal. The trick, I found, was to shift my posture so that the plug in my back door was maneuvered into pressing against the wall of flesh that separated it from my front door. Well, that, and relax.
Mistress’s vintage Frankie Goes to Hollywood t-shirt kept intruding on my mind’s eye, as I willed my ass to stop trying to expel the intruder pressing up inside me, and instead to relax and enjoy.
Yes, that was the key. Relax. Well, that and maybe the warmth of the soup containers resting on my thighs, as the train bounced and shimmied through a number of additional stops. Pure unadulterated kinky pleasure. I was almost sad when we got to my stop.
“Mistress, I’ve got lunch.”
I set my packages on the breakfast bar—the white paper bag containing soup, salad, and some of the best fresh baked bread I’ve ever sunk my teeth into, and the black plastic sack containing three darker pleasures, but pleasures all the same.
I slipped out of my sundress and laid it over the back of one of the chairs.
“Oh, baby,” Mistress said as she made her way into the kitchen and stuck her nose in the white paper sack. “I could smell that the minute you walked in.” She slipped an arm gently around my waist and kissed me.
“Wait ’til you see what’s for dessert, Mistress.” I let a sly smile cross my lips. Let’s see what gets her attention first. Baklava or Charlotte a la plug.
I made an exaggerated show of sticking my ass out as I reached to the top shelf of the cupboard to fetch two glasses and fill them with water. Was Mistress paying attention? Did she see a little flash of electric blue silicone as I reached and stretched?
“Mmm,” I heard. Though of course it was uttered at the exact moment Mistress pulled out the first container of soup.
“We should eat out of proper bowls, not styrofoam, don’t you think, Mistress?” I made sure to wiggle my ass as I reached into the cupboard.
“Mmm-hmm,” she said, still not acknowledging the toy I held between my cheeks.
Finally, we sat down on stools and we ate our lunch.
“So which one is it, Charlotte?” Mistress blew across another spoonful of soup and brought it to her lips. “Small, medium, or large?”
I nearly dropped my fork. As it was, I managed to only lose a slice of tomato as it landed with a splat back onto the pile of veggies drenched in Greek vinaigrette. “Salad, Mistress?”
“Dessert, baby. What size is dessert? And I don’t mean the baklava.” Mistress grinned and motioned for me to come sit on her lap.
I let out a contented little sigh as I climbed up to settle astride Mistress’s thigh. “The small one. I thought I should ease into it.”
“I do so love your sense of adventure, Charlotte.” Mistress’s breath tickled my neck as she whispered into my ear. “I think we should call Juliet and let her know how the bet is progressing, don’t you? But after lunch.”
I smiled. “Yes, Mistress.”
As we concentrated on finishing our lunch, Mistress ate with her right hand, while she set her left hand to wandering over every inch of me she could reach. On more than one occasion that hand made it to the little t-shaped handle that kept my blue silicone intruder from becoming lost forever inside me.
“Mmm,” I moaned, as I felt myself being stretched and then contracting again.
“Miss Natasha?” I hadn’t expected canlı kaçak bahis her to be calling me at this time of day. Fortunately, my marathon meeting was still on lunch break.
“Juliet, honey.” Her voice seemed breathy and about half an octave lower than usual. Sultry, almost.
“Juliet, I’ve got your girlfriend splayed out on my desk,” she husked. “She looks absolutely delicious. She’s got something she wants to tell you, honey.”
I heard some shuffling and then Miss Charlotte’s voice piped up. “I’m going to win our bet, darling. I’m half way there. I’m going to win, and your ass is going to belong to me.”
Oh gawd, I thought. So that’s what this was about?
Before I left for this business trip I had mentioned something to Miss Charlotte about wanting to try some more anal play, or butt stuff, as she so lovingly called it. I remember grabbing my own ass and spreading my cheeks while I told Miss Charlotte that since I was her girl now, that she could do whatever she wanted with it.
She sort of paused after that, and said something to the effect of she would never dream of asking me to do something that she wouldn’t be willing to do herself. I guess she was willing now—or maybe she was willing all along and just hadn’t thought of it yet. Nah, Miss Charlotte’s the kinkiest girl I know. Well, next to her wife, my Miss Natasha, that is.
“Oh Juliet, you should see this,” Natasha was whispering into the phone. “Charlotte’s little ass is loosening up quite nicely with this new plug she bought.”
Miss Charlotte bought a butt plug? She was seriously going to do this.
“It’s just the small one, but it’s stretching her so nicely.” Miss Natasha was just breathing into the phone now. “So nicely.”
Damn it! Why do I have to be so far away when Miss Charlotte gets this kinky idea into her head? I quickly looked around for a private space—an alcove, a coat closet, anything. I settled on one of the smaller meeting rooms, currently unoccupied.
With one hand on my phone and the other scrounging through my bag for my hands-free headset, I plop myself unceremoniously into the chair farthest from the door and any windows. “Tell me more, Miss Natasha.”
“I do think she’ll win the bet you two have going, honey. Listen.”
I was treated to the sounds of Miss Charlotte’s panting echoing around the room. If I had to guess, I’d say they’d gone hands-free too, except on speaker phone. “Mmm,” Miss Natasha breathed. “Charlotte’s ass is such a lovely distraction from work, Juliet. Would you like to hear about it?”
“Y – yes, Miss Natasha. Yes, please.”
“Mmm, that’s a good girl, Juliet. So polite.” Miss Natasha’s voice seemed to hold a bit of amusement in it, beyond just the raw sexual energy that was crackling through the earpiece. “Charlotte has a lovely ass, Juliet. Wouldn’t you say so?”
I brought up a memory of Charlotte’s heinie in my mind’s eye—slim hips, nice curve. “Yes, Miss Natasha.”
“I know you’ve had your tongue in there, but have you ever seen it stretched? Hmm? I mean really stretched. Let me describe it for you, honey.” Miss Natasha was probably smirking on the other end of the line.
I’m sure she knew this phone call was causing a stirring down below for me. She probably also knew that if it got any worse, I’d have to do something about it. And I know damn well that she knew I was in the middle of a production meeting.
“Charlotte went and bought herself a little present, well three little presents actually. She has the smallest one in right now, and I’m staring directly at it. Well, that and Charlotte’s dripping pussy.” That smirk had entered Miss Natasha’s voice again. “Each time I give the present a tug, she moans, and I swear her kitty gets a little wetter. I’d have to say that I think she likes it, Juliet.”
I said nothing, just shuddered and thought about how much I wanted to have Miss Natasha’s hand down the front of my pants right now as she was imparting this information to me. Instead, I squirmed in my seat and listened intently through the tinny headset.
“I think, honey,” she said. “I think that I’m going to have to dive right in and start licking Charlotte’s sweet little puss, while I play with this plug in her ass. I also think that if I do this… oh, let’s say two or three times a day… well, I’d think that after a while, in Charlotte’s mind, butt play and orgasms will become one in the same.”
I moaned, and began absentmindedly running my palms over the tops of my thighs. I shuddered a little more with each pass of my hands. And with each stroke I felt more of a pull toward the inside and upward. My knees were spread wide in a very undignified position. If anyone walks in right now…
“Juliet, honey? Are you still there?”
“Yes, Miss Natasha.” I forced myself to focus on her voice as the pace of my breathing continued to quicken.
“Juliet, luckily for all of us, I am not traveling this week, but unfortunately you are. I have decided that you are to call me three times a day. You will call me during your morning break, and during your afternoon break. I will describe to you the training that Charlotte’s ass is receiving during that time. You will listen, but are not allowed to touch yourself, is that clear?”