BabySitter's Bet

It was quite late when I arrived home with Meghan. Meghan dumped her bag in the spare room and headed towards the kitchen to make some coffee. I don't know why she bothered with a mug. The way she drank the stuff an intravenous drip would be more suitable. While she was doing that I went looking for Cathy, my baby-sitter. My guess was that she'd be in the front room watching the TV.

Cathy was slouched on the couch, feet resting on the coffee table, in that careless style that teenagers have, though you'd think that at eighteen she'd be past that sort of behaviour. I took a moment to check her out. She was a pretty young thing, fit and healthy with a happy disposition. Right now she was wearing a loose top and a short skirt, and the slouching way she was sitting meant far more leg was on display than should have been.

"Feet off the table," I gently suggested as a way of greeting.

"Oh, hi, Mr Roberts," she said with a smile.

She glanced down at her feet and with a very put-upon air swung her legs off the table, one at a time. Doing it, she managed to lift each leg somewhat higher than required, resulting in her panties being flashed at me. It was quite deliberate, too.

She slowly stretched, which caused her breasts to fill that previously loose top, and then she leaned forward, slowly getting to her feet. Her leaning forward returned her top to a state of looseness, and a gaping neckline meant that I had an excellent view of a pair of nice breasts, B+ or C, nicely shaped and unencumbered by anything so inconvenient as a bra.

The smirk on her face said that she knew what she had and she knew that I'd been looking. I had no doubt whatsoever that that had been her precise intention.

"Little girls who tease can find themselves getting into all sorts of trouble," I observed.

"Really? Who could you possibly mean?" she asked, the smirk firmly on her face. "Not me, surely?"

"If the hat hits," I said and she outright laughed.

"Now that's an old piece of slang. Showing your age there, Mr Roberts. Besides what can you do, anyway?"

"Oh, I think I can come up with an appropriate penalty," I said and she laughed again.

"Yeah? What do you suggest? Ground me? Oh, wait, you can't. You're not my father. Stop my pocket money? Don't get any. I actually have a real job these days. Mmm?"

"If push came to shove I could always smack your bottom," I pointed out. "Of course, that could lead to additional penalties."

"What sort of additional penalties?" she asked, and this time it was my turn to smirk.

The message seeped through and she blushed.

"You wouldn't dare," she snapped. "Besides, I could stop you easily enough if you did get any silly ideas."

"Really?"

"Really!"

"Okay, I'll make a deal with you. I'm going to put you across my knee and spank you. If you can really stop me I'll double your pay for the baby-sitting."

"Fine, it's a bet," she said. "I can use the extra money. Amy."

She smiled and waited for Amy to appear.

"We both know what Amy will say," she said. "You might as well start counting my pay now."

"What's going on?" came Meghan's voice.

Cathy didn't even turn around to look. She started right on with her complaint.

"Mr Roberts said he's going to put me across his knee and spank my bare bottom," she complained, stretching the facts as she knew them.

"Really? So you called me in to watch. This'll be fun."

At that Cathy turned around with some haste.

"You're not Amy," she protested.

"No. I'm Meghan, Amy's cousin. Mr Jenkins is at a surgeon's conference for the next two days and as Amy is his protégé she's been requested to go along. Valuable experience for her and I get to play with the kids for a couple of days."

"Oh. Well anyway, you're standing in for Amy so you have to stop him."

"Why's he going to spank you? What did you do?"

"Nothing. He's just going to do it because he's a brute. Tell him he can't."

I caught hold of Cathy's arm, bringing her attention back to me.

"Sometimes when you bet on a sure thing you find that the other person is doing the same. Come along."

I sat on the couch, pulling Cathy across my knee. I flick her skirt up and rested my hand on her bottom.

"Wait a moment," I said. "She said I'd be spanking her bare bottom, didn't she?" I asked Meghan.

"She did. Don't worry. I'll pull her panties down for you."

"Wait," protested Cathy. "You didn't say anything about a bare bottom."

"True. This is entirely your own idea. Consider it part of the additional penalties."

Cathy's panties went down very smoothly, even though she squealed and protested. She also clamped her legs tightly together, trying to hide as much as she could.

"What did you mean by additional penalties?" asked Meghan.

"All I said was that smacking her bottom could lead to additional penalties, and let her imagination supply an answer. A naked bottom was her immediate thought. Me, I'd have suggested taking her top off, as she's not wearing a bra and she seemed rather keen to show what she had under the top."

"No, I wasn't," was Cathy's quick comment while Meghan's was more a thoughtful, "Really? Let's see."

Meghan very quickly and competently helped Cathy take her top off, despite Cathy protesting that this was a bad idea. Bad idea or not, it seemed to me that she didn't exactly struggle against the top's removal.

While Meghan was assisting Cathy get ready my hand was just wandering lightly over her bottom. It drifted here, it drifted there. One finger even slipped into that gap at the top of her legs, probing at the softness there.

"Obviously I don't want to brutalise the girl," I observed. "Half a dozen spanks should suffice, wouldn't you say?"

I addressed the comment to Meghan and she nodded.

"That sounds reasonable, unless she tries to get off your lap and then you'd have to start the count over. You will stay there and count the spanks, won't you?"

Cathy said something rude but I assumed that she was agreeing. I finally delivered the first spank, my hand remaining on her bottom, to rub it lightly. Seeing that the spank had started her breasts swinging I used my free hand to capture them, rubbing them, ignoring Cathy's protest. She seemed to have a fresh protest for everything.

Another couple of firm spanks, including the rubbing of her bottom and the fondling of her breasts and things were progressing nicely. Okay, I'll admit that my rubbing of her bottom might have resulted in my fingers dipping into the gap but I didn't try to force anything. When her legs started drifting apart so that I could rub her a bit more easily it was totally on her.

The final three spanks moved along quite nicely. A firm spank followed by a thoughtful rub, with my hand lingering a bit longer each time. With the sixth spank completed I just naturally left my hand resting where it was comfortable.

After a few moments Cathy found her voice.

"Um, that's six," she pointed out.

"She's right, you know," Meghan chipped in. "Come on, girl, on your feet."

She helped hoist Cathy upright, and I'm not entirely sure how come Cathy's skirt dropped away, leaving her standing there naked. From the startled look on Cathy's face she didn't know either, but the smug look on Meghan's told another story.

"Don't be silly," Meghan reprimanded Cathy when she tried to cover her charms. "It's not as though he hasn't already seen everything."

Speaking smoothly she managed to persuade Cathy to do a complete turnaround, showing off her body to me. Cathy was blushing as she did so but also looking pleased with herself, no doubt patting herself on the back for having the nerve to flaunt herself that way. What she didn't know was that as soon as she was facing away from me I dropped my trousers and shorts, pushing then down around my ankles.

"Okay, now sit on Bryn's lap," Meghan instructed Cathy.

"That's me, by the way," I put in.

"I know that," Cathy snapped, throwing a quick glance over her shoulder.

Meghan was still edging her towards me so that she could sit when what she'd glimpsed must have registered as she threw another longer look at me, her face blushing madly as she found out just how much of me she was seeing.

"Wait a minute," she yelped. "I never agreed to anything like that. No way, no how."

"Oh, stop quibbling," scoffed Meghan. "You knew perfectly well where this was all heading. Now sit."

With that Meghan gave Cathy a firm push on her shoulders, resulting in her moving a little further back, her knees bumping against mine and abruptly buckling, having her plop down onto me.

At least, she would have plopped down if I hadn't taken immediate steps to protect my nearest and dearest. I caught her, propping her up slightly as I steered her into a more appropriate position. That done I let her start to sink downwards.

"Hey, no, stop," Cathy demanded, my cock starting to press up into her passage. Unfortunately for her she was doing the sinking down, not me doing the thrusting up. She was off balance and could do nothing until she gained some traction with her feet, not helped by the fact that my feet seemed to be stopping her gaining that traction. Not deliberately, of course. It was just one of those things.

She slid down onto my cock just as neat as you please, her passage being slick and hot, probably from my earlier attentions. As soon as she was settled into position she turned her head and glared at me.

"You take that out," she demanded.

"If you didn't want it you shouldn't have sat on it," I protested.

She spluttered angrily and I laughed.

"Listen, Cathy, like it or not, you're nicely skewered by my cock and I have no intention of withdrawing. You might as well cut all the nonsense out and just get with the action. It'll probably finish a lot faster that way. Wriggle around and we might be stuck together for half an hour or more. Now be a good girl and bounce."

She called me a few rude and hurtful names but proceeded to bounce. It was quickly evident to me that this wasn't her first ride as she knew just what she was doing. What had surprised me was Meghan leaving as soon as Cathy started bouncing. Now she was back.

"Have a look," she told Cathy, positioning a mirror that was supposed to be hanging in the bathroom. "Now you know what it looks like when he thrusts into you."

I was amused to see that I could see her in the mirror, moving up and down my cock. I was even more amused to see Cathy checking out her performance. Then, to my surprise, she started playing to the mirror. She'd pull up a little and sink back down. She lifted herself I was half out of her and examined what it looked like. Dropping back down so I was full in her she studied the mirror, just rotating slightly and watching. Then she raised herself so high I thought she was going to pop right off and I grabbed her waist to make sure that didn't happen. She laughed and plunged back down onto me.

After this had gone on for a few minutes I decided that enough was enough. My hands tightened around her waist and I started thrusting in somewhat more forcefully, no longer letting her set the pace. She moved with me easily enough and her attention was no longer on the mirror but on me and what I was doing to her.

I drove in harder and faster, sensing her nearing her completion and trying to time things so that she climaxed. She finally did so and I just cut loose, giving my all most energetically.

As soon as Cathy relaxed Meghan was hauling her out of there to get tidied up. I tidied up myself, not that that took much doing. I then counted out Cathy's baby-sitting money, including a nice little bonus.

I saw Cathy take note that her pay included a bonus but she didn't say anything. She just tucked the money into her purse as I escorted her to the door.

"I suppose my having being here means that you won't be having any little adventures with Meghan tonight," she commented slyly.

I gave her an amused look.

"What on earth makes you think that? I fully intend to undress Meghan and have her try out a number of different positions before I finally ride her ragged," I said.

"What? That's not fair."

"It's not?"

"No. She got to see me being fucked. I should be allowed to see her get a cock planted in her. Multiple times if you're trying different positions. That's assuming you can do it a second time tonight and you're not just big-noting yourself."

I shrugged and turned back to the front room, Cathy tagging along.

"Megan, you have a little problem. Cathy insists that it's a case of you watched so she's entitled to watch. She also wants you to have the initial spanking. Any comments?"