Kirk The Charmer

It was late on the first full day that they had been at the cabin and a lot of people had gone to bed. Kirk was sitting in the living room area of the cabin on the main floor watching television and he had seen Debbie and Chad walk down into the basement a little while ago, so it was probably just the three of them that weren’t in their rooms yet. He just wasn’t tired so he figured he would stay up for a while and just watch some television.

After a while, he considered going up to the room that he was in until he heard some footsteps coming down the stairs. He turned toward the stairs and saw that it was Chad’s mom, Hilary walking down.

“Oh, hey Kirk. Having trouble sleeping?” Hilary asked.

“Not really. I just wasn’t tired yet.” Kirk said.

“Yeah, I was just coming down to get some water. Mind if I join you?” Hilary asked.

“Not at all. So, how has your day been?” Kirk asked.

“It was great other than the hangover I had this morning. We probably shouldn’t have drunk so much last night.” Hilary said, chuckling a bit.

“Well, I thought it was fun seeing all of you moms let loose for a while. You don’t get to do that often when we are at home.” Kirk said.

“That’s true. It was a lot of fun while it was going on, that’s for sure.” Hilary said.

“So, you don’t have to answer this if you don’t want to, but I figured I would ask just for the hell of it. Who do you plan on fucking while you are here this week?” Kirk asked.

Hilary gave Kirk a shocked look and then she shook herself out of the shock. “I am a happily married woman, Kirk. I am not cheating on my husband.” Hilary said.

“You can say that now, but I know all of your friends have been fucking us guys for a while now and I know you aren’t that different from all of them.” Kirk said with a smirk.

“Shit, you got me there. To tell you the truth, I don’t know if I will have sex with anyone, but if the situation arises I don’t think I will turn it down.” Hilary said.

“If you were to pick a few guys, who would they be?” Kirk asked.

“Well, this is just hypothetical of course, but I would say that Patrick would be at the top of the list. Got to see what all the hype is about. After that, I would probably say Ben and maybe Ty or Johnny.” Hilary said.

“That’s a good list. I do have to wonder why I am not on that list though.” Kirk asked.

“Maybe I left you off just to see your reaction.” Hilary said, chuckling at her son’s best friend.

“Well, I would be very disappointed if I wasn’t in the running for a shot at you.” Kirk said.

“Oh, would you now?” Hilary asked.

“Very. It would be a shame to not have a chance at someone as beautiful as you are.” Kirk said.

“You wouldn’t rather have sex with someone your own age?” Hilary asked seriously.

“There is plenty of time for that. It’s not everyday that you get a chance at your best friend’s mom. I think the best way to take advantage of that is when you are on a trip when her husband isn’t around.” Kirk said.

“Such a smooth talker. You might be working your way up my list.” Hilary said as she winked at him.

“That’s good to hear. So, to more of a serious subject for now. How is everything going with work? Mom seems to think that everything is going well, but when I come over and hang out with Chad, you look kind of stressed.” Kirk said.

“I am a bit stressed. I am the one putting up most of the money for the newspaper to run smoothly. I don’t need any help with that. I know your mom has to take care of you and as a single parent she doesn’t have the money to spare.” Hilary said.

“What about Mrs. Thompkins?” Kirk asked.

“Oh, Shirley gives me a good amount of money a month to help and pay for things, so that helps out. She gives the same amount that your mom does.” Hilary said.

“So, what's the problem then?” Kirk asked.

“Things just cost more than they used to, so I tried to take on the extra costs myself, but I am going broke trying to do that.” Hilary said.

“I am sure that mom and Mrs. Thompkins would be willing to help out if you asked.” Kirk said.

“I know they would, but I don’t want to let your mom take up some of the slack when she needs the money to put you through college.” Hilary said.

“That’s nice and all, but you can’t be taking all of this on yourself. You will burn yourself out.” Kirk said.

“I have things in the works to make some more money. Don’t worry about me, sweetie.” Hilary said.

“You are my best friend’s mom. It’s hard not to worry about you.” Kirk said.

“That’s sweet, but like I said, I have things in the works.” Hilary said.

“Do you mind me asking what those things are?” Kirk asked.

“You can’t tell anyone, but I have been working on that app that Jenn set up for a few weeks now.” Hilary said.

“You are whoring yourself out for money for the newspaper?” Kirk asked.

“I guess you could say that. I haven't gotten much traffic yet. I got a chance the other day and it was just one of your classmates who wanted a blowjob from a MILF, as he put it.” Hilary said.

“Damn. Never thought I would see the day that you would join an app like that.” Kirk said.

“Don’t be so surprised. When I was in high school I was just as loose as the rest of the moms who are here aside from your mom.” Hilary said.

“I just don’t see that side in you now.” Kirk said.

“Oh, it is always there. I just keep it well hidden most of the time. How do you think that I keep Jimmy so willing to do what I want him to.” Hilary asked, winking at Kirk.

“I guess you let your inner slut out.” Kirk said, smirking back.

“You’re learning. You know, I was thinking about something the other day. We need to get your mom dating someone. She is going to be lonely next year when you are off at college.” Hilary said.

“I have thought about that. I have even mentioned it to her and she always shoots the idea down. I don’t want her to be lonely when I am gone, but I don’t know what to do to get her to start dating though.” Kirk said.

“I think all we can do is just continue to work on her. She might take the idea if we keep working on her together.” Hilary said.

“I can do that. You and all of the other moms need to do the same thing though.” Kirk said.

“We will. If nothing else, we will have her over a lot so that she isn’t by herself all the time.” Hilary said.

“I would appreciate that.” Kirk said as he moved closer to Hilary and pulled her into a one armed hug and then sat back to watch more television with his arm still around Hilary’s shoulders.

“Trying to make a move, are we?” Hilary chuckles from his side.

“What can I say? I was having an emotional talk with a hot woman and I wanted to let her know that I appreciated everything that she was doing for my mom.” Kirk said.

“I would do that for everyone. You know that.” Hilary said.

“I know you would. That’s why you are one of my favorites.” Kirk said.

“So, what do you have planned for tomorrow?” Hilary asked.

“I’m not sure yet. I will decide when I see what all the others plan to do. If they go skiing, I will go as well, if not, I will find something to do here.” Kirk said as his hand started to move lower and he suddenly started squeezing Hilary’s left tit.

“Smooth move, but you are going to have to do more than that to get in my pants.” Hilary said with a smirk.

“Oh yeah. So, it is on the table then?” Kirk asked just to make sure.

“Sure, it is.” Hilary said as she moaned as Kirk started to pinch and roll her nipple between his fingers through her shirt.

“Good to know.” Kirk said as he reached between her legs and started to rub her pussy through her shorts she was wearing.

“You are off to a very good start!” Hilary moaned as she was feeling so much pleasure from what Kirk was doing to her.

“You haven’t seen anything yet.” Kirk said.

“Well, show me what you have then, stud!” Hilary moaned.

“Patience, Aunt Hilary. We are in no hurry here.” Kirk said.

“Speak for yourself!” Hilary moaned as she turned toward Kirk and pulled him into a kiss.

The two of them kissed while Kirk kept his hands running all over Hilary’s body to make sure that he kept her turned on. Kirk never thought that his night would turn into this but he wasn’t going question his luck as he had one of the hottest MILFs in Big Lake wanting to fuck him. He would be an idiot if he did.