Megan And Jessie 05

I perhaps made a mistake when I made a bet with Jessie. I might have really paid for it more than I was intending.

You see, the other week, I was giving Jessie a bit of crap about a test we had to take. She was insisting she could score better than me.

Now I know I really like everything about Jessie, and would never say something bad about her. Yet I know that I tend to do better at school stuff than her. All through middle and high school I always graded better than her. Heck, it was a miracle when Jessie even actually did any work.

I think she may have just been trying to come up with an excuse for her to improve her grade. She wanted to put something on the line I believe.

She had made a bet with me that whoever got the lower score, would be the other's maid for a day. So the loser essentially would have to do a lot of chores for the other by the sounds of it.

I wasn't really worried much, so I took her up on it, she was insisting after all.

Then when the test grades came in, I was shocked to see how much better she had done.

The problem was, it really only amounted to a B-, and I still scored an A on the test.

Jessie isn't much of a sore loser though, so although not happy she lost, she was happy she did so well still. I was happy for her too. We agreed she would come over to my house during break. My parents would be away, so I figured I could use both a helping hand and the company.

So you may be wondering why I was the one paying for it. Well it's a bit difficult to explain, but I'll do my best from the top.

My alarm rang at my usual wake up time. I made sure to shower and pick out something nice to wear. Even though I would have a personal maid for the day, I still made my bed and made sure my room was clean. Although Jessie had been over hundreds of times in our friendship, I still liked making the best presentation for her. I may not be much, but at least one day, if I get lucky and we get close, I won't scare her away by being a slob.

Soon 9:00 AM rolled around, and I heard the doorbell ring. I was practically surprised, Jessie was rarely so punctual.

I quickly opened the door, but what I saw shocked me. Standing there at the door way was Jessie, and she was absolutely naked!

"What are you doing?!" I asked her quickly. I grabbed her by the arm and pulled her inside and shut the door.

"Sorry Ma'am, I don't understand the question. I am here just as you asked me to be," Jessie explained.

I took a closer look at her once I was sure she was safely inside. I didn't need the neighbors seeing a naked girl at my doorstep.

"That's not what I meant Jess, where are your clothes?" I asked.

"Oh, I didn't bring anything unnecessary Miss Megan. I only brought what was absolutely necessary," Jessie verified.

My mouth hung open. I couldn't believe Jessie would take a silly bet that far. "You didn't really leave all your clothes at home?"

"I brought some things to wear during certain duties today Ma'am. I made sure I was really prepared," Jessie said while holding up a small duffle bag.

"You did not need to bring a special uniform, but you better put it on right away!" I said.

Although I was shocked Jessie would risk driving across town naked for this bet, it wasn't a total shock. Jessie was always like that.

However, when she actually began to open her bag, I was more shocked. Jessie, once naked, is near impossible to get redressed, especially if she didn't have a reason to. Alone in my house, I figured she'd insist staying naked.

I guess I was sort of disappointed. I had been so shocked up until that point, I didn't get the chance to really look much. She was as gorgeous as ever that morning. Her hair was tied up formally, a tad different than her usual style, but it looked really cute on her.

Of course I did get a chance to look at her bare breasts before she got anything on. They were still as firm and round as I remember them. She practically glowed, probably having taken a shower and gotten ready before coming here. She was even cleanly shaven between her legs. It's embarrassing to admit I looked that close though.

Jessie pulled out a relatively small white fabric from her bag. I wasn't sure at first what it was, but she quickly stuck her head in a loop of it, and I realized that it was an apron!

Jessie took some time putting it on. She straightened it out, and began to tie it. She even partially turned her body while she tied it, and I could see her round bottom sticking out, completely exposed.

"Aren't you forgetting something?" I asked, a tad mesmerized.

"Hm? Am I Miss Megan? I would hate if I did," she asked, genuinely confused.

"Your clothes Jessie. You're still pretty much..." I began to say, unable to say the word too loudly, "naked."

"Oh Miss, I am your servant today. It's my job to serve you today," She said. I quickly took in air. Although I was sure she couldn't possibly mean it the way it sounded. I'm sure any other girl who would stay nearly naked for the sake of 'service' would mean it in a different way. Jessie though I think was trying to say that clothes weren't needed, since they wouldn't help her be the maid for the day.

I know it's a bit of a jump in logic, but I have been her friend for over a decade. You sort of start to learn to speak Jessie-ese.

She even got out a small maid's headdress and put it on her head. The white bit of frill and black ribbons looked really cute.

Jessie was now smoothing out her 'uniform' for the day I suppose. The apron was pure white, and looked quiet thin. It seemed to just float atop her beautiful form. As she looked down at herself, inspecting it, she twirled her body. As much as I'm sure she was making sure that the outfit was where it was needed, I was noticing other things.

As she shifted in her spot, the apron shifted across her skin. Up top, the area of her chest that was covered loosely sat and moved around. I could practically see the two spots where her nipples were, the apron being that thin.

Speaking of there not being much material, the apron didn't cover much. I could definitely see some cleavage above. Along her sides, the apron didn't even fully hide her body. You could tell she was naked from the sides of her sticking out. I suppose her slender waist was just barely hidden by the width of the cloth, but you could definitely see her smooth and bare hips sticking out.

So as I was saying, as she swayed about, the front of the apron only held where it was thanks to some ties in the back, swished left and right with ease. Every time, I could swear I saw her bare pelvis, at least from the side.

The apron didn't even reach her mid-thighs also. I suppose normally decency isn't the main job of an apron, but even still I felt it was overly skimpy.

My eyes shot wide as Jessie took hold of the hem of the apron and lift it a bit. Although it was only a couple of inches, I could see all of her bare thighs. She then continued on with a curtsy motion. "Jessie, reporting for duty Ma'am," she said.

I was nearly speechless. From the bare thighs, and now the peek I was getting down the front of the apron, I was astounded. I know I see her naked all the time, I in fact did just a couple of minutes before then. However something about her having something on made it sort of naughtier.

"Um... yeah... you know you don't have to call me that, right?"

"Oh but Miss Megan, someone in a submissive position as myself should always do as her mistress asks. She should never question an order. She should always show absolute respect on top of that. Today I am here to do every one of your needs Miss Megan. I am going to on top of it be as proper as I can be.

"As proper as a half naked made can be, huh?" I thought to myself. I wasn't about to argue with her though, so I just let the matter drop.

"Is there anything you'd like me to do first Ma'am?" Jessie asked, standing up straight again from her curtsey.

"Well, I was thinking we could just sit around and hang out," I explained. I wasn't really planning on her pay off the bet that much. I really was just thinking I'd have her help me clean up a bit later that day.

"No Miss Megan, you must relax yourself, and I will get to work," Jessie said. Even with all the talk of her being the submissive one today, she quickly grabbed my arm and pulled me towards the couch in the living room. She had me sit down in front of the TV. I didn't really know what to do; I was still trying to come to grips with her body in such a tiny outfit still.

"Ok, you sit here. I will prepare you some breakfast since I already have my apron on. You wait right here and I'll get you a drink."

"Thanks..." I muttered as I tried to relax back in my seat. Jessie for a moment turned to go to the kitchen, but quickly whipped right back around. The effect on her apron guaranteed a view of her bare mound.

She didn't' notice my staring thankfully, but then again that's because she quickly knelt over me. Each of her arms was around the sides of my head. Only an inch or two fro my eyes was her chest. Between the crevice of cleavage and the shape of the two round orbs through the thin cotton, I wasn't sure what to look at.

"Tell me when you're comfortable," Jessie asked, her hands manipulating a pillow she had snuck behind my head. Every time she adjusted it, I noticed her breasts would bobble.

My mouth was completely dry. I barely was able to croak out a, "that's fine, it's good." Jessie seemed happy with that, and again headed towards the kitchen.

I let out a sigh. I was telling myself it was too early for me to get so worked up so quickly. Even if I loved my luck for seeing her, it was incredibly stressful too. Yet even with that thought, I still caught myself staring at Jessie as she walked away, the bounce in her step causing her bottom to bob about.

Jessie happily hummed to herself as she looked through my fridge. "Would orange juice be good for you Miss Megan?" She asked. I told her that would be fine.

I turned on the TV, and switched it to the news. I wasn't exactly interested, but I knew I needed to do something. If I wasn't careful, even Jessie would realize I was staring at her. It was hard though. She seemed so naked, yet that apron just barely hid her at times. I don't know why just the tiny teases of nudity were working on me as well as her total brazen nudity might. I don't know why I don't get tired of her body for a second.

Soon Jessie was serving me my juice, and even prepared a bowl of cereal. I wasn't about to have her cook me anything after all, I didn't want her to actually work for me.

After my breakfast, Jessie asked if I needed anything. I wanted to say no, but she seemed really insistent. "Well, if you insist. I guess I'd like to check my email and such. Would you mind getting my laptop?"

Jessie left for my room, leaving me just a moment alone. I eyed her backside again as she left, but let out a larger sigh once she was gone. I was starting to wonder if I should feel a little guilty at all. It seemed wrong to let her parade around like that. I hadn't asked for it, but surely I could get her to wear something.

Jessie returned with my laptop, and set it in front of me. I didn't open it though; I decided I would at least make things right between us. It was wrong of me to just keep her exposed for my fun.

"Jessie..." I said, trying to find the words. Like usual, a lump formed in my throat. Telling such a beauty to get dressed never seemed like the right thing.

"Yes Ma'am?" she asked.

I looked at her at her smiling face, eyes beaming so brightly. "Well... I think you need to dress a bit more decently..." I said.

Her face turned to one of confusion. I instantly felt a bit of guilt. "I mean you're hot! We both know that!" I then immediately kicked myself mentally. I just told her she was hot, and I hadn't meant to do that. "Well I mean, like... well..." I was trying to explain myself away from the compliment, but I could see the look of confusion coming back to her. "No, I'm not saying you're not, I just... I mean you do look good, anyone would want to look at you like that, especially me, well no I mean..."

Jessie was still looking at me. I couldn't believe all that I was saying. I always get like this. It doesn't help that I kept looking down at her body too. "What I mean is you look great and all. You really do. However I would like if you would put more clothes on and be dressed a bit more decently. You know, cover up areas a bit better. You can borrow anything of mine."

I was so relieved when Jessie didn't seem upset. "Thank you very much Ma'am. I will go right away," I then watched as her naked butt walked away again, hopefully for the last time that day so the two of us could have a normal day.

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Megan and Jessie #5 Part 2

By Jappio

I opened my laptop, and began to check around. I told myself I'd end this little game of Jessie's soon, and the two of us could watch a movie or something.

However Jessie returned and I was shocked when I couldn't even tell if there was anything different. I saw the same apron, and a lot of bare skin peeking out from it.

I had to really concentrate, but I saw two black bows at her hips!

Jessie had gotten a hold of something to wear, and it was probably one of the last things I wanted her to find.

Although she was facing me, I instantly knew what she must have had, and I suppose there is a bit of a story I should share about them.

You see, a couple of months back, I was doing some shopping. I was looking at the selection of underwear they had, and well... I'll admit I was thinking about Jessie wearing some of them. However I started to think about me in them. The idea was embarrassing, but I figured if I would think Jessie would be cute in them, maybe I'd get lucky and Jessie would think I looked cute in them too.

So looking at the selection, I settled for a tiny silky pair. My face was red as I made the purchase, and barely thought about it till I was home. Then that night I tried them on in front of the mirror.

I was astounded really. Although they appeared black, I didn't have enough backbone to really look them over in the store. There were portions like the bows that were black. The waistband was solid, although had little frills around it and the leg holes. However most of the fabric was sheer in the front and back. You could see almost my entire butt and even my fur in front. Only a small black patch existed for modesty, and it didn't hide much.

I told myself I couldn't wear something like that in front of anyone, much less Jessie! So I hid them away in my drawer and never gave them a second thought. I didn't even want to return them, it would be too embarrassing.

Now Jessie had found them, and was wearing them!

"Ok Miss Megan, what would you like me to do next? I could start some cleaning if you'd like?"

I wasn't even able to stammer at that point. My face was red from her finding them. I also couldn't help but wonder more how she looked in them. Suddenly the indecent apron was too decent!

"Um... what?" I asked, almost mesmerized trying to picture them in them.

"I could start with some dusting if you'd like Ma'am," she clarified.

"Um... sure yes, that'd be great!" I said, wanting to change the topic.

Jessie headed towards her bag. The whole time I looked at her out of the corner of my eye. As she was to my side, I could see her from head to toe, bare except for the little ribbons on the waistband of those panties. I couldn't believe she was wearing them.

I tried taking a deep breath and sit back. She hadn't put on nearly as much as I had asked. She was still so exposed. Yet I couldn't send her back again. I didn't even want to acknowledge the panties.

However there was little ignoring the panties on my part. As she walked around the room with her newly found feather duster, I got a lot more opportunities to see what she looked like squeezed into them.

Occasionally I'd be lucky when she'd turn or twist suddenly, and I'd be able to see what they looked like in front.

The apron offered no coverage behind her. I could see quite clearly that the garment wasn't her size. They hugged every curve. The sheerness of them meant it was hardly different than when she didn't have them before.

Well I say that, but I did discover I was right when I bought them, that they would look wonderful on her. I don't know, even though they were the wrong size, and I hated that she found them, there was something about them. The little black bows swinging about, the way thing fabric curved about. The way that I could quite tell where her naughty parts started. Had she not been cleanly shaved down there, maybe, but the fact she wasn't meant I could only guess how much of her was actually covered by the little bit of privacy silk. Just picturing all her naughtiness hidden away snuggly was a lot to handle.

Don't get me wrong, I love seeing her naked, but seeing her lingerie and a naughty outfit in general was new to me, and I liked it. I did always say it would be nice if her strips did have a bit more to them then just her outer layer disappearing right away. Then again I guess I'm clearly a pervert, wanting these things from her. I can't help it though. She's so beautiful, and I love everything about her.

Her cleaning was getting her into more and more poses too that I couldn't pass up staring at a bit. I was so lucky she was so dedicated to the bet, and she never faltered from tasks. Yet there are times I couldn't help but stare open mouthed.

For example, at one point she was close to me, cleaning a small table to the side of the couch. She starts out standing right next to me, which is bad enough. Then to get to the far end of the table and over the lip of it, she starts to bend down. She keeps her knees straight, and this just pushes her butt out at me. Just a foot from me, her practically naked bottom is presented up in the air. Heck, even the opaque black patch of the panties was sticking out, and I knew what had to be nestled in there.

"Are you Ok Miss Megan," Jessie asked as she turned to face me. My face had really begun to burn up. There's only so long a girl can go like this, and I still had a lot of hours to go of this 'torture'.

As her cleaning came to an end, I felt a little saved as I heard my phone go off. I had figured some of our other friends might want to hang out during break, and I figured this was maybe that! I could hopefully get Jessie to relax some and kill off some of the sexual tension.

"The Megan estate, may I ask who is calling?" I heard Jessie say. I quickly spied that she had grabbed my phone before I even had a chance to. It was going to be hard to explain why Jessie was answering the phone like that.

"Ma'am, it's for you, a Miss Stacy is calling," she announced. I quickly snatched the phone from her.

"Hi Stacy," I said.

"Hey, what's up with Jessie?" Stacy asked.

"Oh, just some bet," I explained. "I'll tell you more later."

"Later as in, could you come get me? We're pretty bored being back in town with nothing to do. She's going to drive to your place, but I could use a ride, and I'm not really on her way."

The idea didn't sound bad. With others around, I was sure Jessie would loosen up some and we'd be able to have some fun. The bet was turning out to be more work than I intended, and I had won.

"Sure, give me just a moment and I'll come get you guys," I said.

"So, are you going to be leaving for a bit Miss Megan? I would be most happy to go and pick them up for you," Jessie offered. I thought about how she had driven naked here.

"No, no, you don't need to do that. In fact, don't you think it would be best if maybe...?" I tried to think how to put it, I really didn't want to bring up the panties, and also I definitely didn't want to be so blunt about it either. Last thing I wanted to do was make her feel weird or anything.