The Babysitter

Author's notes: For people who are wondering why Johnny is included in these stories, it is because this babysitter story was planned long ago.

For those of you wondering if these are the same characters in every story, they are. Even a few who are mentioned only in passing will show up in future stories, and already have.

Having said that, this is not great literature. Read the stories in any order.

For those of you wondering if any of the characters ever caught diseases, they did not. They are all fictional, and exist in a universe where there is no such thing.

In the real world, if you and your wife are swingers, wear a fucking condom. Every. Single. Time. This means you.

* * * * * * * *

After Susan and I divorced, we actually got along better in a lot of ways. Although she was supposed to have Johnny two weekends per month, it usually worked out to just one. She would visit during the week, though, and she stayed in touch with him as he grew, but she left almost all the "parenting" to me.

This was actually a pretty good arrangement for both of us. We never fought over custody, or really anything. In fact, we got along consistently better after the divorce than when we were married. For several years, she would stop by for dinner once or twice a week, help put Johnny to bed, and then give me some kind of quickie sex before leaving.

Susan's blowjobs were always slow and sensual, and ended up being the high point of my sex life for many months. In a way, I was surprised at how well it worked for me. I had decided to concentrate on my job, and on being a good dad, and so I went through several years without dating.

When Johnny was eight, I decided it was about time to start going on the occasional date, and so I started making all the mistakes that everyone else makes. First, I joined one of the dating websites, and started planning to go out with women that I really knew nothing about.

Although I talked with Irena online, we didn't meet in person for more than two weeks. She was about my age, and also divorced, but when she was available, I was busy, and vice-versa. When a Saturday night came available, it turned out that Susan was not available to provide babysitting, so I had to find someone new.

Fortunately, there were some neighbors only a block away with a daughter who had volunteered to provide babysitting just a few weeks ago, and I had actually kept her number. I didn't know much about Claire except that she looked like a high school girl, and her parents were close enough that she could call for back-up if anything went bad.

When I called Claire, she said that her only plans for Saturday night were to watch online movies with her friend, and she would be glad to babysit if her friend could come along. I said this was fine, and told her that she was welcome to use my HBO.

When Saturday night came around, Claire showed up at my door with a guy named Wes, who looked like a college football player. She introduced him as her boyfriend, and said they were both going to school at Westwood, which I think may be a community college.

It was not exactly who I figured she would show up with, and I guess it showed on my face. But both of them assured me that they were just going to play Monopoly with my son, and not do anything (or smoke anything) in my house. They both seemed honest enough, and it wasn't like I had much choice, so I thanked them for showing up on short notice, and left.

The date with Irena was designed for simple but elegant. We were going to a restaurant downtown called 'Atlas', which had been getting rave reviews. It was inside a nice hotel, and in the back of my mind, I harbored a fantasy about getting a room.

The dinner went well at first, but somehow we just didn't hit it off. She seemed to be having a lot of financial problems, and may have been looking for a guy to fix all her problems for her. Although my career was going well, it didn't seem like we had much of a connection, and she kept giving off signals that she was slightly mad at me in some way.

By the end of dinner I figured out that she was disagreeing with me about politics. When we were talking online, I had let it slip who I was supporting in a a local election, and apparently she had already decided not to agree with me about anything else. It was not clear why she had even decided to go out with me, but I chalked it up to experience, and spent the rest of the evening talking about kids, which turned out to be a safe topic.

After dinner, I paid and left a generous tip, even though she had offered to pay her half. I walked her to her car and gave her a friendly kiss goodnight, but I didn't ask her over, (and she didn't offer). In fact, looking back, she didn't even ask if I would call. She promised to send me an e-mail, which is exactly what she did. It was all very cordial.

When I got back to my house, Wes appeared to be gone, and Claire was propped up on the sofa watching 'Game of Thrones'.

"You are back early." She said.

"Yeah, I think the date was technically over before it started." I smiled.

She turned the TV off and turned toward me. She was giving me a playful look, but she was clearly looking me up and down. "She should have given you a BJ just for Atlas."

I laughed. "I have been out of the dating scene for a while. Maybe I should get you to negotiate my next date."

We talked for a little, and she described how Johnny had gone to bed a little late, but he had insisted on staying up to win the Monopoly game. She said Wes had lost on purpose because he was hoping Claire would give him a blowjob for helping out with babysitting chores.

"Fine by me if you guys had some fun." I said, "You guys were nice enough to play Monopoly with an 8-year old. Maybe at least someone got some action tonight." I noticed that they had closed the blinds.

"I am glad you said that," She smiled. She was hinting that she had given Wes a reward, but she didn't say anything else. She just said; "People can be too serious." If she had been looking at me closely enough, she would have been able to tell that I had developed an erection.

She stood up and walked over to me, with a lot more confidence than I expected from someone who seemed maybe 18 years old.

"I have a business proposition for you."

Claire was actually very short, and also thin and hot in the way that only college girls are. Her height and her tiny waist made her look much younger, and I was actually worried at first that she might be underage.

Her hair was kind of a dark blonde, with a strong wave that came down below her shoulders. She was wearing white silk shorts, and a tight blue t-shirt that hugged her figure and showed off her breasts.

Her breasts were about average size, maybe a B cup or a C, but she was wearing what must have been a very expensive bra that held them high in place without looking uncomfortable. She practically radiated sexuality, and she walked like she knew it. Just looking at her, and thinking about what the "business proposition" might be had made my erection more obvious.

I tilted my head a little to indicate that I was listening.

"You need a blowjob," she said, "and I need an extra $100."

This was the best thing she could have possibly said. Honestly, as horny as I was right then, I would have paid a thousand. But she had apparently set the price to match the cost of the restaurant I had just left.

"That sounds like the best offer I have had in a long time."

She walked closer to me. "There are a few rules," she almost whispered.

At that point, I would have agreed to anything, but I listened anyway.

"No hands, and no emotions," she said, looking me right in the eyes.

There had been a brief Summer storm earlier that evening, and I could still hear thunder rumbling in the distance. Other than that, the house was quiet, and she seemed to be waiting for me to provide an answer, or a rejoinder, or something.

"No hands?" I questioned.

"Oh, I will touch you. But you just sit back and enjoy. This is just business. I don't need another boyfriend."

That actually sounded pretty good to me, and I said so. Once I had agreed, she didn't waste time. I had expected her to have me sit on the sofa, (since she had used the phrase "sit back"), but instead she motioned for me to stand, while she sat down.

I stood in front of her, as directed, and she almost immediately unbuckled my belt, and unsnapped my dockers as if it was the most casual thing in the world. I was about to help pull down my underwear, but she took care of it with no hesitation. I am guessing she had some practice, (maybe that same night).

Even though she had the confidence of taking charge, she seemed flushed with the excitement of being a bad girl. It was a sexy combination, and it made me wonder how much she had planned this. I imagined her giving Wes a blowjob in this same position, maybe just a few minutes earlier. For some reason, that made me even more horny.

When she released my dick from my underwear, it was already at full attention, and was aching for relief. She didn't tease me at all, but just casually leaned forward, and took about three or four inches of my dick in her mouth. I realize this sounds really, really sudden, and it was. From the time she mentioned giving me a blowjob to the time she had my dick in her mouth couldn't have been more than a few minutes.

Looking back on it, it is a little weird that she went from zero to blowjob that quickly, but at the time, it felt like a fantasy.

I wanted to reach down and cup her breasts, but I remembered her warning about "no hands". Instead I just watched as she wrapped one hand around my shaft, and started fingering herself with the other. She occasionally looked up in my eyes, but mostly she focused on my dick.

She was jerking herself off with the same tempo as she was jerking my dick. In fact, she must have started off just as excited as me, because she started with a fast pace, and sped up to the point where it was somewhere between "enthusiastic" and "explosive" Even though the lights were on, I didn't have a very good view of her body, so I just stood there, and braced myself so I wouldn't fall.

Claire had been holding my dick lightly with her mouth, and her left hand, but when I told her I couldn't hold back much longer, she increased her grip slightly, and pouted her lips so that she would be ready for my load.

Within a few seconds, my dick erupted, pumping what felt like a gallon of cum into her mouth. She gasped a couple of times as if she was having an orgasm as well, or possibly having trouble swallowing. But she didn't spill any of my cum. Not a drop. Not only did she keep it in her mouth before and after each gasp, but she even kept my dick inside her mouth for a minute or so afterward, so that she could suck out the last of the semen as I relaxed.

When she was done, she simply stood up, gave me a light kiss, and said "I need to go clean up. I will be right back."

It didn't seem to be true, of course. She was not even sweaty, much less dirty. I figured she was just excusing herself so I could get my pants back on and stop standing there like an dirty old man with his dick hanging out.

While she went to the bathroom, I cleaned up my clothes, and got out $200 to give her for the "babysitting". When I gave her the money, she actually tried to give $100 back.

"Nope," I said. "You specifically asked for an 'extra' $100, so this is babysitting money plus the business deal."

"Nice to do business with you, then." She smiled as she pocketed the money.

"Let me drive you home," I offered. "It is late."

She refused to let me drive, but instead insisted on walking. I would not have been comfortable leaving Johnny alone, even asleep, and I think she knew it.

Claire gave me another quick kiss, and grinned: "Sorry I can't invite you over."

I tried to think of something witty to say, but my conversation skills are not exactly my strength.

"Doesn't matter, I had a great date night," I finally said. I hoped it came off as kind of a sarcastic understatement, but I suspect it just came off as "deliberately vague".

She continued smirking: "So let me know next time you need some babysitting. I love playing with little Johnny."

That one at least I had a comeback for. "He enjoyed it too."

"Well, if you decide you want a night out with the guys or something, I am free on Thursday," she hinted.

"That sounds good." I said. "I will call you."

With that, she turned and went outside, but turned back around once and flashed me a smile. The smile reminded me of lightning. It was beautiful and natural, but I got the feeling that if I got too close, I was going to be sorry.

That week actually went really well. Susan had stopped by on Tuesday, but had not given me any action at all, so by Thursday, I was ready for more "babysitting". I called Claire on Wednesday just to make sure she was still available, and she seemed pretty excited by the idea.

When Thursday night rolled around, I had made plans to go out to dinner in case she showed up with Wes. A few hours before, though, she had texted me that she would be driving, and said something that kind of hinted that Wes was not around.

It gave me time to check to see if Susan could take Johnny early, and as luck would have it, Susan was more than willing. "Got a date lined up?" Susan asked?

I admitted that I did.

"Anyone I would like?" Susan was always direct about being attracted to every cute girl in the state.

"Let's try to keep this one separate," I said. Susan knew exactly what I meant by that. Even though we still had plenty of sex, we respected each others boundaries. Susan showed up almost immediately, and picked up Johnny early enough to take him out to dinner and still have play-time left over.

Claire showed up alone, just a few minutes after Susan left, wearing an off-white dress with thin straps that was see-through in a flower pattern near her waist, and again near her thigh. Her hair was down again, and it gave the impression that she had prepared for this evening like it was a date.

"Nice Dress," I said.

"You like it? I bought it with babysitting money."

I doubted a dress like that could be bought anywhere for only $100, but maybe the $200 would have put her in the ballpark.

I told her I had made dinner plans so my car wouldn't be in the driveway.

"Where's Johnny?" she asked.

"His mom picked him up earlier this afternoon."

"Awesome, let's go eat."

So we did. We went out to a restaurant called Ecco that was considered to be one of the best date-night restaurants anywhere. It was surprising that I got a reservation that easily, but maybe Thursday afternoon was not their peak hour.

The conversation went surprisingly well, considering the age difference. I had thought that we would have nothing in common, but she and I shard the same politics, volunteered at some of the same places, and she was even studying the same branch of engineering that I had studied in college.

It was thoroughly enjoyable, and by the time we got back to my car, she was tipsy from just two small glasses of wine. I had kept my hands off her, but it was impossible to keep my eyes off her. She smiled and laughed easily, and radiated the simple enjoyment of having a good time.

As I opened the door to my truck for her, she stood close, leaned in and kissed me. The kiss took me by surprise, and I did't have time to kiss her back. Instead, I just stood there like an idiot trying to figure out if I should go in for a real kiss, or a hug, or just ignore it and close the door for her.

She went ahead and climbed into the truck while I stood there holding the door. She took charge of the conversation (since I clearly was not able) and got right to the point: "I am really horny tonight, can we have sex instead of a blowjob?"

This night just kept getting better. "Sure." I said, trying to act as casual about it as she did.

"You have condoms, right?"

In fact, I did not. I had a vasectomy many years earlier, and Susan usually just gave me blowjobs, so I hardly ever used them. We had to stop on the way home to pick up a box of condoms. As soon as we got back in the car, she casually opened the box, and got out a condom. While I drove, she unbuckled and unzipped my pants, put the condom on my dick, and started rubbing her hand up and down on my shaft.

After less than a mile, she leaned over and took my dick into her mouth, condom and all. She must have known that I would not get off from a BJ while wearing a condom, but I have to say, I was closer than I thought I would be. Instead of jerking my dick with her hand like last time, this time she was actually sucking on it. It felt good, but the view was far and away the best part of the blowjob. While she was playing with my dick, she had puled her panties off, and I had a pretty good view of her pussy, which was cleanly shaved. Her legs were thin, and her pussy lips were so small that they were almost invisible from my point of view. The total effect was so distracting that I kept glancing over to watch her middle finger plunge in and out.

Judging from her pace, and her bad jerking, Claire seemed genuinely close to coming. She had hiked her dress up only a bit, but I could tell that she had stopped penetrating herself, and started rubbing her pussy all over, and really quickly.

She may have actually had an orgasm in the car, but it didn't seem to stop her, or even slow her down much. As she seemed to be switching gears, she suddenly looked up and said, "Pull in here." We were at the apartment complex down the street from my house, but I wasn't about to try to change her mind.

She showed me how to park near the pool in a place that was well away from the other cars. I realize that teenagers must have long figured out all the places they could fuck without being caught, but the danger in this one was real. I wouldn't exactly get fired from my job if I got caught fucking a babysitter, but it wouldn't make me too popular with her parents.

By the time I parked, she was already pulling down my pants. My truck was pretty big, so she had plenty of room to climb over on my side. I lowered the seat to make us less visible, but she didn't see to care. In fact, as she straddled my dick, she sat straight up to give herself a better angle.

Claire closed her eyes as she slowly lowered herself down on my dick. She was already wet, I assume from a combination of her own juices plus the lubrication of the condom. In any case, she was impaled on my dick up to the hilt in a matter of seconds.

Just like the blowjob, she didn't waste any time. Instead of starting off slow, she started off bouncing up and down on my dick, and quickly progressed to a deep grinding motion. Claire didn't speak much, but she did look me directly in the eyes almost the whole time. Instead of talking, she set a faster and faster pace, and started making noises as she approached her orgasm.

Claire closed her eyes and said "Oh, Oh, Oh...". Her face was mostly serious, although she did start giggling one time when she bounced so hard that she bumped her head on the headliner of my truck.

Her pace was so fast that I knew I was going to come pretty quickly, even with the condom on. When I told her I was about to come, she said "you'd better." While I chuckled at that a bit, she increased her pace again, grinding her pussy down on my dick so hard that she had to wrap her legs around me to hold herself in place.

As soon as she started her orgasm, it sent me over the edge, and I started coming pretty hard. To increase the pressure, I reached up, and pushed her tiny shoulders down. This had the desired effect, and she started having such a loud orgasm that I was worried it might attract the police. "Oh Fuck," she yelled out. "Harder, Harder."