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.
