Meals on Wheels 6- Teaching Ruth’s Granddaughter

She gave my ass a little squeeze as we made our way out. When we got into the car and started on out way back, Ruth turned to me and said:

“So I was wondering if you would do me another favor.”….


…continued

“Well, considering what you asked for last time, this should be interesting.”

Ruth gave a little chuckle and said: “I guess I have been asking quite a bit of you, never mind.”

I got the feeling that Ruth was feeling a bit hurt. “No, I didn’t mean it like that, I was just saying that we keep going further every time we get together.”

“Oh, yes, well I guess that may be the case here, too. My granddaughter comes over quite often, and we visit for a few hours every week. Her mother tends to be very quiet and reserved, so I have ended up being the person Carrie goes to with all her questions and problems. We talk about pretty much everything, and I don’t keep any secrets from her.”

I was a bit curious at this point to see where she was going with this, but I remained quiet and let her continue as I drove.

“A couple weeks back when I dyed my hair, she asked me why I did it in such a bright color. I tried to tip-toe around the subject and just told her that there was a man whose attention I was trying to get. Carrie wouldn’t let it rest at that, and she was asking me if it worked and why the family had not met my new boyfriend. I told her that you were not that kind of boyfriend, but apparently that just raised more questions. I had the birds and the bees talk with her a couple of years ago but apparently her mother has told her that she shouldn’t even be thinking of such things, and she must wait until she is married. So she was a bit confused when I told her that I had a man that I just have sex with. Then she asked me why I didn’t just pretend we were having a serious relationship and show you to the family anyway.”

I pretty much froze when she said that, but luckily she continued;

“Then I told her how old you are and explained that physical relationships can be taboo and break rules that other people wouldn’t be happy about. Then the conversation finally came off of us and Carrie wanted to talk about herself. She told me that she was a virgin and was having second thoughts about what her mother had been telling her. She said that her classmates in high school,…… she just turned eighteen two weeks ago by the way,…. spread gossip all the time and she didn’t feel comfortable with any of the boys she knew. She would tell me about all the sexual things her friends would tell her, and how she desperately wanted to experience those things for herself.”

Now I was back to being curious, and a little turned on.

“She asked me if I thought it was alright for her to have a physical relationship with a guy, and I told her I didn’t see much problem with it as long as she wasn’t jumping into bed with a bunch of different guys, made sure to use a condom AND use birth control. As soon as I told her that, she said she didn’t have any guys in mind, so she asked me if I would share my boyfriend! I was shocked when she said that, and I said there was no way I would set you up with her. She said she didn’t want to date you, she figured you had to be the type of guy I would approve of if I was already with you. I told her it wasn’t right for two women to be treating a man like a time-share, and she turned my earlier comment about taboos around on me. Then she told me she didn’t want to share, she wanted to join in, like on a threesome!”

My head just about exploded at this point. We pulled up to Ruth’s house and I shut off the car. I put my face in my hands and rubbed my eyes as I tried to wake up from this bizarre hallucination I was having. I had just finished servicing the 95 year old mother of my current sex partner, and now she is suggesting that I take a run at the third of four generations of her family.

‘So what do you think?” Ruth asked.

I just sat there for a moment wondering what to do. I think I already knew what I was going to do, but maybe I was just imagining how to go through with it. “What did you have in mind?”

Ruth smiled, “Well I basically just want you to pop her cherry. I want her to enjoy herself, but I want her to learn the basics, along with a few special things. I want her to know how to please a man, and I want you to have a good time, but I was hoping you could do a few favors for her as well. Don’t worry, I will be walking her through it, and I will be participating to make sure you get what you need. I may demonstrate a few things as well. She said as she grinned and opened her door. I’ll go set this up for next week, she’s inside waiting for me.” She said as she pointed to the car parked in front of us.

I watched her go into the house and then I drove off, thinking about next week.

I made my deliveries to her for the next few days. Ruth told me that she wanted to do it on Thursday night, and then we started to chat about different things that she wanted to make happen for Carrie’s magical night. Ruth seemed to be as excited as she would if it was her first time.

Thursday rolled around and I found myself just a little nervous as I made my way up to the front door. I rang the bell and Ruth answered the door.