The Trouble With Babysitting, Part 1

by Thom

My friend Marsha and I hadn't thought for even a minute that we were into girls. But we had just turned 10 recently so we hadn't thought much at all about what we might be in to. Boys at that age are so strange that we mostly went out of our way to avoid them. We did have a crush on teen age boys that we saw in movies but none of the boys who lived around us were any where near cool.

What we were in to though was becoming older so that we could become independent from our embarrassing parents. I thought that if I spent even another whole minute with them, especially in public, I would probably die. We thought that money was the key to being independent and Marsha and I completed a baby sitting certificate course so that we could get baby sitting jobs.

The course was really easy. They taught you how to change a diaper and hold a little baby and when to call 911 if the baby stopped breathing or had drowned in the bath tub because you were stupid and left it there by itself. Those are the things that mothers expect if you are alone with their precious children.

Anyway, after the class, Marsha and I posted our names and phone numbers all around the neighborhood where young mothers might be; like the day care center and grocery store and pretty quickly we got a bite. This woman calls me and says she is Mrs. Windsor and she would like a baby sitter. Well, don't you know I'm thrilled and I say great I'll be there at such and such and that there will be two of us but we won't charge you any more for two than we would for one. We just like to work together.

When we turn up for the job, we find that Mrs. Windsor is pretty far out there. She's dressed like a guy and has really short, spiky hair. I think maybe it's a strange color like you see the punk kids wear but I'm not totally sure because it's kind of way too dark in her house. I can see that she has a bunch of tattoos though on whatever skin I can see on her arms and ankles.

We don't dwell on her too much though because it's the kid we are the most concerned about but she turns out to be lovely. In fact, in contrast to the mother, she is just this really cute, normal looking, blond, curly haired little two year old kid named Molly. She has been fed. She is already in her pajamas. All she needs is a bed time story says her weirdo mother and then she will be out like a light. We couldn't have asked for anything more.

So, Mom is gone, kid is in bed, sawing zzz's and we're not sure what to do next. My friend Marsha suggests that we should poke around in closets and drawers and stuff and look for weird stuff that Mrs. Windsor might have. Marsha says she once found a book about how a man and a woman have sex and make babies when she was staying with her cousin and her cousin's parents weren't at home. She says they had the best laugh about it. So, for the fun of it, we started poking around.

We decide to start in Mom's bedroom because she was so far out there that we thought she would have all kinds of neat stuff in her room that we would like to paw through. It turns out we were pretty much right about that. We started in her closet and found a bunch of strange kind of clothes for a woman. That is they were mostly guy-looking clothes. It was obvious to us that Mrs. Windsor was more into being a guy than a girl.

We next poked into her dresser drawers and we were surprised that we didn't find guy undies. In stead, we found really, really sexy girl panties and bras and teddies and stuff like that. And we found hose and garter belts there too, not one pair of panty hose so if she wore hose it must have always been with garter belts. I was beginning to feel a bit of a tingle between my legs feeling her underwear especially the see through teddies and the hose and garter belts. It was hard for us to imagine Mrs. Windsor in this sexy stuff under her guy clothes.

There was another bedroom in the house that wasn't the little kid's room and not Mrs. Windsor's room so we went there next. Well, I have to tell you that if we were surprised about the stuff we found in Mrs. Windsor's bedroom, we were flabbergasted by what we found in this other room.

First of all the furniture in there was kind of strange. There were a couple of really heavy wooden chairs with stocky legs and arms and thick backs. There was a bed of similar material that had a head board and a foot board with a bare mattress on it, no pillows or blankets or anything that would make it so you could sleep on it. All of the furniture was really marked up like it had had really hard use of some kind. Finally, one wall of the room was virtually covered with a mirror so that you could see yourself no matter where you were even on the bed.

The room had hooks in the ceiling in various spots, some over the bed and some not over the bed and there were some hooks on one of the walls about three quarters of the way from the floor to the ceiling. At the time we thought this was all strange but we didn't make any connections to anything. We just thought this was all some more of Mrs. Windsor's weirdness.

Since there wasn't anything else to explore in the room except for the closet, we went directly to it. Well, the closet was the most amazing place and it fully defined our lives for the next few weeks and our relationship with Mrs. Windsor and her little kid.

I hope you don't think I'm wasting your time by going through an item by item inventory of what we found in there but before I go on with this story, I need to give you the bigger picture and then I can go into the details of how Marsha and I and Mrs. Windsor and the little kid all got involved with all of the stuff Marsha and I found in that closet and the weird furniture and the hooks all over the place that were in that room.

The first thing we encountered were the boots and not far away from them were the gloves. Both were made of the most exquisite leather that Marsha and I had ever touched. The gloves were long. When you put them on, they went beyond your wrists as normal gloves do and reached up your forearm. The boots were calf length and had these amazingly high-spiked heels. I mean they must have been six- or eight-inch spiked heels. When I first saw them, I couldn't imagine how anyone would walk in them. When I put them on way later in this story and did walk in them, it wasn't as hard as I thought it was going to be when I saw them this first night.

There were two other things in the closet, a bureau and a book case. The book case seemed to have a bunch of magazines stacked on it so we went for the bureau. It had four drawers in it. We went from top to bottom. The first drawer had more hose and garter belts in it. But these were different than what we found in the other bedroom. The garter belts were all made of the same kind of leather that the boots and gloves were made of. The hose were all black, mostly of the mesh variety but some sheer.

The second drawer had whips and switches and bridle crops in it. There must have been two dozen items of a variety of sizes.

The third drawer contained metal handcuffs and leather wrist and ankle cuffs and ropes and chains. All things that you might use to make people helpless if you didn't want them moving about too much. The hooks in the wall and ceiling made a little more sense after finding this stuff.

The fourth drawer had a variety of plastic things that mostly resembled guys' dicks. Most of them were attached to pants or belts so that you could wear them and apparently pretend you were a guy and had a hard on. Some of the plastic dicks didn't have pants or belts and some of them had two heads like maybe they could go two places at the same time.

As we went from drawer to drawer we got a sample of each of the things out and lay them on the bed so that we could examine them and try to figure out what was going on here. Then we decided to go for the magazines. Wouldn't you know, they were the secret to everything? The magazines had pictures in them that demonstrated all of the items that we had laid out on the bed from the other drawers.

To begin with, all of the people in the pictures were women. Some women seemed to be in dominating positions over other women who were in subservient positions. Mostly the women in subservient positions were either tied up in one way or another or they were kneeling or leaning over something with their bums in the air or lying on their backs with another woman squatting over their face or maybe sticking one of the plastic things in one of their holes.

Well by this time, Marsha and I are really turned on by all of the sex we've experienced and all of the sexy stuff we've seen and handled and we've started to push our hands into the crotch of our jeans that we are wearing trying to get some relief from it. I can't remember which of us suggested it but we were soon naked, sitting on the bed with all of this stuff around us and pouring through the magazines looking at one amazing scene after another of women doing things to other women that aroused us to no end.

We both lay back on the bed with the bare mattress, picking a magazine or two that interested us and pounded our pussies with our hands until we had come several times and were feeling a bit of relief. But not enough to put it all away and go make pop corn and watch TV.

I know it was Marsha that made the next suggestion. She said she wanted to try some of things that she saw in the magazines and she wondered if I wanted to too or would at least play along. She said she wanted to put on the boots and gloves and hose and garter belts and see how it felt. And probably do some more jigging off. She also said she might like to try some of the restraints and maybe the whips.

Oh, my, I was thinking. This was all quite a bit for me to absorb since we had just come into it all but I was certainly game. By some miraculous turn of events, I was more inclined to be the other player in the magazine pictures, the one doing the spanking or the stuff that the women were doing with the plastic dicks to the women who were tied up or tied down.

We quickly went for the gear in front of us. We both put on a pair of hose and the leather garter belts to hold the hose up. Then we put a pair of boots on and a pair of gloves. We paraded in our outfits in front of the mirrored wall and I think we looked very sexy in them even with our little-girl bodies without any titties and our hairless, little-girl cunnies.

It wasn't long before we were both ready to touch ourselves again particularly with the leather gloves on and when we did it felt really nice. At first we were masturbating ourselves with the gloves but before long we had reached over and were using the gloves on each other.

I was beginning to worry about the time and suggested that we better put all of this stuff away before we get caught by Mrs. Windsor. Marsha though begged me to use some of the restraints on her and one of the whips or riding crops before we put it away.

I have to say that I wasn't opposed to this suggestion and that in fact it excited me a great deal, I was just kind of worried about being caught. But my arousal out distanced my worry and I grabbed some leather cuffs for her wrists and her ankles and told Marsha to kneel down next to the bed. I secured her in the cuffs and grabbed a riding crop and began to slap her bare bottom with it. Marsha immediately said I was way too wimpy with the spanking and that I should hit her harder. I was being turned on beyond belief by spanking her and seeing her bound helpless so I was more than happy to intensify the strength it. A couple more whacks at a more intense level and Marsha was crying and begging me to stop.

I did stop of course because I was really concerned about being caught by Mrs. Windsor with all of her stuff out and Marsha and I dressed in it. We were just barely able to get it all put away and get out of the extra bedroom when we heard Mrs. Windsor coming in the front door. Panting a bit, we were sitting on the sofa when she made it to the living room.

"What, no television girls? What have you been doing with yourselves all of the time I've been at out?"

"Oh, mostly homework," we lied. "We had a bunch tonight."

"Ah, well that's good use of your time. My daughter was cooperative, I assume and stayed asleep after you put her down?"

"Oh, yes," we said, "she was great. We'd be happy to stay with her again if you ever need a babysitter," I said in hopes that she would invite us back.

"I'd like that too," she said. "How does Friday night sound day after tomorrow?"

"Perfect for us," I said. "We'll see you then."