Dating My Son - Cover

Dating My Son

Copyright© 2024 by JennaK

Chapter 4: Third Date

Erotica Sex Story: Chapter 4: Third Date - How far should a mother go to help her son learn the ropes of dating? That is the question I faced. Going on a practice "date" with him seemed like a good idea. I never expected where it would actually lead. Read and find out how far I went.

Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa   Reluctant   Heterosexual   Fiction   Incest   Mother   Son   First   Masturbation  

In the morning Andy was not a shy or self-conscious as the previously week. He looked at me and smiled a knowing smile when he came down for breakfast.

Andy looked more confident, and mature. I was pleased that I had a role in his development. But more than that, I was still glowing from our make-out session the evening before. I smiled back at him.

“And what does my young man want for breakfast today? How about a special batch of pancakes just for you.”

“Sure, ... Mom.” (I think he was going to call me Sue, but changed his mind.)

“Yes, honey, I am Mom during the week, but I am your girlfriend Sue on Saturday night. That is, if you want to date me still.”

“You mean we are going out again?”

“Well, if we do go out on a date again, I think it is only right that you actually call me and ask me out. If I am called and asked nicely, I would certainly consider it.” I smiled when I said that, to let him know I was an easy yes. I expected a call that day.

The little prick waited until Tuesday afternoon to call me for our nex tdate. I was beginning to worry that he chickened out.

I was at work when he called me on my cell phone. He sounded like the nervous 14 year old that he was.

“Sue, this is Andy ... I ... wanted to know if you wanted to go out with me again ... on Saturday ... if that is all right with Dad.” His voicetrailed upwards in a sign of lack of confidence.

“Andy, you don’t have to worry about that. He understands that this is agood education for you. So leave him out of it. It is just Sue and her boyfriend Andy. OK?”

“Ok.”

“So, Andy, when can I expect you to pick me up?”

“How about 8 for a movie again.”

“OK, Andy. See you then.”

So, he did it. He asked a girl out on a date over the phone. His technique could use some improvement, but he accomplished the basic task.

I knew (even if Andy didn’t) what a third date meant on the dating schedule that I adhered to in High School. Third date was feeling up under the bra, and over the panties. But most importantly for Andy was that the girl would stroke off her date to orgasm. I wasn’t sure that I could go that far with my son, but I decided to let the situation flow on the date and decide then.

I didn’t wait until Saturday to jill about the prospect of Andy’s hands on by bare breasts, caressing my nipples and maybe even kissing them. And possibly my hands on Andy’s cock. Even though I was at work, I went to a stall in the restroom and jilled to orgasm thinking of what his hands would feel like under my bra and how good it would feel to push his hands up between my legs. For the rest of the week, I jilled nightly in the bathroom just in anticipation of the date.

On Saturday, as before, Peter met Andy at the front door and said that Sue would be down shortly. He asked Andy where we were going, and Andy described the movie – one of those superhero sequels. They did some guy talk about the powers of various superheroes while I finished my makeup.

I picked out a bulky sweater – all the better for Andy to reach under – and considered not wearing a bra on the date. But I didn’t want Peter to get suspicious if he saw my bouncing boobs as I came down the steps, so I put on a front clasp bra that Andy could easily open without that awkward reach around that would flummox him in exposing my boobs. I wore a modest skirt that was hemmed just above the knee, but had my prettiest panties on under in anticipation that I would be exposing them for Andy to see during our make-out session.

Peter again played the my “Dad” and told Andy to be a gentleman with me and get me home at a reasonable hour. I told “Dad” again not to wait up and I would use my key when we came home. Peter smiled in anticipation of a good wake-up blow job on Sunday morning. A wife does have to keep her man happy while she dates someone else, doesn’t she?

On the way to the movie, Andy didn’t need any direction to place his hand on my exposed leg as we drove. He caressed my leg just under the hem of the skirt – seemingly testing how far up he could go. Later, of course, he would have full access all the way up, but at that point I didn’t let on to where the date was headed. He kept his hand just under the hem, caressing the area between my knees and thighs. He was getting good at that.

We returned home at 11 and I said I had to go the the bathroom. I went up stairs to check on Peter to make sure that he was asleep. I didn’t want him checking on me and finding us with Andy kissing my nipples or me stroking his cock. Fortunately, Peter was asleep as requested. He deserved a good sucking in the morning.

While I was upstairs, I decided to just remove the bra entirely. My nipples stiffened from the sweater rubbing against my nipples as Iwalked down the steps. I was already wet with anticipation of making out with my date.

Andy was on the couch. I fell into his arms. As we began kissing he reached for my breasts and gave me a surprised look when he felt how soft they were without confinement of a bra. I told him he could reach under the sweater and caress them if he wanted. And he sure did want.

Kissing him, our tongues dancing, and his fingers on my nipples was heavenly. My pussy was on fire from the touch of his bare skin on my bare breasts. I wanted my nipples sucked, so I pulled off my sweater and told Andy that he could kiss me there too. The thrill was electric. A direct line from my nipples to my clit as soon as his lips touched my nipple. While he was kissing my breasts, I opened my legs and pushed his hand all the way up to my panties and held his finger there.

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