BabySitter Despondent

As a single father I find I’m stuck at home all too often. Not that I begrudge it, I love my children. They’re a constant joy to me. But it is nice to get out on the occasional night for some me time.

When I do get a rare night out I have a baby-sitter in. Naturally. You can’t leave the little monkeys alone and expect to still have a house when you get back. Kerry is my normal baby-sitter. She’s been coming around for a couple of years now. I expect that she’s going to retire from baby-sitting soon. She’s turned eighteen and has a proper job so the part-time money from sitting will no longer appeal.

When Kerry fronted up for my latest night out she seemed different. Normally she is full of bounce and cheer, but this time she was quieter, almost despondent in her attitude. I thought of trying to jolly her along a bit to see if I could cheer her up but decided to leave well enough alone. It wasn’t really any of my business and as long as she could handle the kids with no problems I should just butt out.

She seemed to cheer up a little when the kids tackled her and shortly after that I kissed the kids goodbye and headed off.

I had an enjoyable time, catching up with a few old friends. It was pushing midnight when I finally got back home. I wandered into the front room and there was Kerry, curled up in a ball in one of the armchairs, sound asleep. There were tear tracks down her cheeks. I sighed and gave her a gentle shake to wake her.

She hopped up pretty smartly, embarrassed to being caught both asleep and crying. I gave her a nice easy smile.

“Want to talk about it?” I asked. “I may not be able to help but I can listen. Sometimes it helps just to be able to talk about it. It might even let you make up your own mind about things.”

She looked at me and tried to smile, shaking her head.

“No, I’m fine,” she said, and the tears were welling up in her eyes again.

I reached out and tugged her towards me, just holding her. She pushed against me for a second, then leant against me, sniffling as she fought back her tears.

All I wanted to do was give her a little comfort, but I wouldn’t have been human if I hadn’t noticed what an attractive armful she made. I rubbed lazy circles on her back while she snuggled against me, seeking a bit of comfort. Then she began to talk.

It was the standard story. She had a boyfriend. He pointed out that she was eighteen, and he was horny, so she should attend to his needs. If she really loved him she would do it. But she wasn’t ready to go that far with him. Upshot was he found someone who would. And denied it, as he wanted her in bed as well.

As she talked I could feel her attitude firming up. Her boyfriend was an asshole and she’d be damned if she was going to let him badger her and walk over her. He could get stuffed and she’d find another boyfriend. Not all men were arrogant assholes.

“Most of us are,” I pointed out, and she gave a muffled snort and thumped me on the chest.

“Why don’t you just try and relax a little,” I suggested. “I’ll rub your back and you can just let all the tensions drain away.”

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I was already rubbing her back lightly and continued to do so. So my administrations might have wandered slightly further afield than her back, but her bottom was soft and running my hands over it was also relaxing.

I don’t really think that it was my fault that her skirt rode up a little. It was a tight skirt, and not very long, and when it dragged against my hands it just seemed to bunch up around her waist. I didn’t take advantage of this by trying to dip inside her panties, but I did continue massaging her back and bottom, and if that meant I was rubbing her through her panties, so what?

After a minute or so Kerry was calming down nicely, just relaxing and letting me rub her back. She was still chatting about her boyfriend, but she seemed to be able to see him quite clearly now, and was reinforcing her own idea that it was time to tell him to take a hike. While she was talking, by some mischance, her panties got hooked on my thumb and pulled away from her slightly. I eased them back into position, taking care not to brush against her mound while doing so. I probably took a little too much care, resulting in her panties finishing up bunched to one side of her pussy, leaving it bare. Not that I was thinking of touching her up her.

Now as I said earlier, Kerry was a very nice armful, and the way I was rubbing her back was proving a bit disconcerting to me. To be blunt I had an erection and it was uncomfortable. To relieve the pressure I unzipped and let it out. I could always zip up again before Kerry noticed.

I guess it was a rather unwise decision on my part. My erection seemed to just rear up between Kerry’s legs and press against her pussy, which I had inadvertently exposed. I didn’t try to push into her. I was supposed to helping her relax, not seduce her.

Kerry tensed slightly when she felt my cock touch her but I was talking softly, telling her to ignore it.

“Don’t worry about it,” I advised her. “It’s not going anywhere. Just relax, let your problems drift away while you continue talking.”

We just stood there, me leaning on the wall and holding her, continuing to gently rub her back as she talked. I wasn’t trying to take her. It was just that my erection was nicely placed and pressing against her slit in just the right place. You can’t really blame me if her lips decided to part slightly so that my erection could ease into her.

It was a slow process. I didn’t really notice it myself until I realised I was pressing against her hymen. I assumed that would be as far as I’d go and was quite surprised when it yielded without a struggle, letting me advance slowly up her passage.

Kerry finally seemed to catch on that something untoward was going on and leaned back a little to look at me, a puzzled look on her face.

“Just ignore it,” I told her. “It’s nothing really. Now, what were you saying?”

She started talking again, but I was aware that my erection was advancing nicely and it wasn’t that long before I was nicely placed inside her. My hands came down to caress and hold the cheeks of her bottom.

Seeing I was in her I decided that I’d just have to make the best of it. With my hands on her bottom, holding her firmly against me, I started gently rocking.

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“Just relax,” I said softly. “Feel the movement and relax in time to it.”

We moved slowly and gently against each other, softly rocking, while I spoke quietly to her, encouraging her to relax and just feel. Her hands were bunched in my shirt as she swayed in unison with me, the magic slowly building.

It’s surprising how long you can go on if you’re not in a hurry. We just stood there, moving softly against each other, the motions going on and on. Kerry had closed her eyes and let her head drop forward against me as she swayed, ignoring everything but this new feeling building up inside her.

The whole thing was bloody murder on my nerves. I wanted to just let rip and totally ravish her body, ripping her top of and feasting on her breasts, while my cock pummelled her into submission. Instead of that I was gently rocking her, building her passions a tiny bit at a time, while trying to keep my own passions subdued.

Kerry was, I was happy to note, breathing harder, making little happy noises as we moved, a touch of urgency creeping into her movements. Slowly but surely I started taking longer thrusts until I was pulling well out and driving firmly back in. Kerry seemed quite happy with the change, pushing urgently to meet me when I drove home.

The change proved too much for Kerry. She started making a funny noise, excitement bubbling forth, and then she climaxed, clinging frantically to me as her body shook, while I relaxed and let myself go.

Afterwards she sagged against me, while I whipped out a handkerchief (happy to find I actually had a clean one) and wiped her pussy and straightened up her panties and skirt. Stuffing the hanky back in my pocket, I held her, hands once more rubbing her back.

I could see the life rising in Kerry, and it wasn’t long before she was back with me, looking very animated.

“What did you do to me?” she asked.

What did I do? Was she kidding? I just screwed her arse off.

“Oh, it’s an old relaxation trick I learnt,” I said airily. “How do you feel?”

She moved a little away from me, apparently no longer needing me to hold and comfort her.

“I feel great,” she said. “And I can see things a lot more clearly, too. My so-called boyfriend is just a selfish pig. If he felt anything for me or had any respect for me he wouldn’t expect me to have sex with him just because he wants me to. I’m going to tell him to take a hike.

Thank you for listening. I really needed someone who would listen while I talked without butting in with silly suggestions. It was my problem and I just needed to be able to talk it out to myself.”

Ten minutes later she was gone, practically dancing to her car. It touches your heart when you can help someone just by listening.

Updated: December 20, 2016 — 7:00 PM

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