How to be a Good Son Ch. 02

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Jason learns how to be a good brother.
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Part 2 of the 2 part series

Updated 02/06/2024
Created 01/23/2024
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This story is a continuation of my first story 'How to be a Good Son'. I would recommend you read that first. Here, after some cleanup from the last chapter, Jason learns to be a good brother.

VERY quick synopsis. Jason and Tracy, mother and son, are on a quick business trip in Hawaii. They met another couple, daughter Susan and father Keith, and connected. Last night the women switched rooms for the first time.

Woke up with Susan in my arms. She was looking at me, smiling.

"Well, it's about time. I didn't want to wake you, but I really need to go."

Susan got up and walked to the bathroom. Naked, of course, after last night's antics. It struck me that it was like watching a statue from a museum come to life. I could see her dress from last night's dinner party draped over a chair. After a few minutes I heard the shower turned on.

"Jason, I need your help. I can't quite reach the middle of my back."

Now THAT is a good reason to get out of bed, I hurried to her side. After testing the water temp, Susan got in the shower and I followed. We started off washing each other. After all, there was 'some' residue of last night on both of us. I then got into the stream and shampooed, rinsed, then let Susan get in the water to do her longer hair. I took a couple minutes to rinse. Standing behind Susan, I wrapped my arms around her waist, then moved hands up to her breasts. Everything was slippery and warm. Susan leaned back into my chest. It didn't take long for me to be fully hard, fully excited. Susan could feel the attention on her behind. She reached around and positioned me lower, between her legs.

Susan, also being tall, was the perfect height for this. I started moving, back and forth along her pussy, with Susan getting into the motion. Eventually she reached between her legs and positioned me against her opening and pushed back. I slid in easily, Susan was already wet. I held her tighter. We were slow and easy, not frantic like the first time the night before. A steady connection, enjoying the moment. Over time the rhythm sped up, and eventually I could feel Susan shutter, and let out a satisfied moan. I kept the motion going and had my own orgasm a couple minutes later.

We got out and toweled off. My phone went off, a call from Tracy.

"Morning Jason. Hey, last night you said you wanted to meet for breakfast at 10:00. Well, it's 9:00, and I'm having a little issue getting ready. Seems you have all my clothes and makeup in your room. I didn't want to barge into you, but I think Susan and I need to swap, at least for this morning".

"OK, give us 10 minutes and come on up."

"Susan, I think you have to go. Tracy's coming up in 10."

"So, you screw my brains out all night then kick me out in the morning. I see how this goes."

"Well, you could stay and explain what evils you did to her favorite son all last night. That would be interesting, especially if we're still naked."

"OK, getting dressed, I see her point. I'll leave, and see you back at breakfast. I really don't want to wear my dress from last night, people might get the wrong idea. Can I borrow a t-shirt and some shorts?"

"You mean people will get the correct idea. Anyway sure, t-shirt and shorts coming up."

The shorts fit Susan OK, if a little loose. Just have to cinch up the belt. The t-shirt is one Jason just bought at the gift shop. Unfortunately, or fortunately as the case may be, Susan was not wearing a bra with her dress last night, and she currently fit VERY well in Jason's t-shirt. Something about seeing Susan in a too-tight t-shirt, braless, was more erotic than seeing her naked. Yet another mental image from this trip Jason wanted to keep. In fact he got his phone and took a couple quick pics of Susan, showing all her assets.

Susan gathered up her clothes from last night and headed for the door, barefoot. A quick kiss and she was gone. A couple minutes later Tracy knocked and Jason let her in.

*****

Susan and Keith had decided before the trip to extend the stay a couple days. They saw Jason and Tracy off at the airport shuttle stop at the hotel. The trip back had a quick stop in Honolulu, then an 8 hour flight back home. Plus a 5 hour time difference. The flight from Honolulu left at midnight, getting them home early Sunday afternoon. The intention was to sleep as much as possible on the flight. Jason had a window seat, with Tracy next to him, with a woman in the aisle. They put down the arm rest between them, with Jason backed up against the window and Tracy laying against him. This gave Jason more leg room. It was a little chilly on the plane so they draped a blanket over themselves.

At this point they were not talking much, other people were trying to sleep. The position was a little convoluted, but they managed to get relatively comfortable. Tracy closed her eyes, using Jason's shoulder as a pillow. After Tracy settled down, Jason was surprised to find his hand positioned over one of Tracy's breast. He gave a little squeeze. Tracy opened her eyes for a couple seconds, looking directly at Jason, then closed them again, a smile forming.

Jason thoughts were swirling, as they usually did.

It feels really nice being this close to Tracy, comfortable. I have a new relationship with Susan, excited to see where that will go. Am I cheating on Susan, holding mom like this? Or is the relationship with mom something different than with Susan, can exist along side? Just what is my relationship to mom? How does she feel about me, as something more than a son? Well, play it out, see where things go. But no lying, to anyone. Well, maybe to Karen. THAT truth would just make everything even more, complicated.

The plane landed and after retrieving luggage, and a good bye kiss, they went their separate ways. Normally at the end of a vacation you feel happy about the trip, but a little sad that it's over. This time, for both Tracy and Jason, there was that, plus the anticipation for the relationships just forming.

*****

Susan did make it back to work by that Thursday. They had lunch in the office cafeteria and decided to do dinner that night, where it would be easier to talk.

"Wonderful trip. I didn't want a bunch of people to overhear us at work, this works much better. By the way, I checked out the community college. In June they have a scuba certification class. I'm thinking about going, I would love to go diving more places, go deeper and stuff. Plus the exotic places you get to go. Beach life might just be for me."

"Agreed, I might just tag along. I really liked the scuba too. Jason, I know there's no ban on employees dating at work, but I really don't want 'us' to be common knowledge, at least for now. Not that I don't want to keep going. Everything happened so fast in Hawaii, I almost feel like I need to take a step back and get to know you. No matter what happens I want to keep you as a friend. That, in my dating experience, just about never happens. Eventually someone does something to the other, tempers flare, and the relationship ends. Very sad, actually. So, can we just date for a while? I'm not saying we will not 'get together', I'm just not ready for you to move in with me. I mean I've only known you, been with you, for what, 3 days?"

"Yep, I get that. Vacations can be like that, or so I'm told. People let loose a little more, things happen. If everyone knows we're a couple, it just gets more complicated. Especially if we don't make it. So, Susan, are you available, say Saturday night?"

"Let me check my social calendar. Yep, looks like I can squeeze you in. I'll let you figure out the details."

"So what do you think about my mom and Keith?"

"They seemed to have fun, a good connection. Biggest issue I see is dad lives a half hour from me, in the wrong direction for your mom. If they want to keep it going, it'll be long distance."

"After dating a younger woman for years, will your dad think mom is too old?"

"Actually we talked about that. I think dad is done with younger women. Course, your mom kind of looks like a younger woman anyway. I don't see that as an issue. That's not something we can fix or do anything about anyway. Up to them to figure out."

"What about the other elephant in the room. Are you OK dating a younger man?"

"4 years difference? I think I can handle that."

"Just to let you know, I've always had a thing for older woman. Just saying."

"We get to see each other every day at work, and date when we like. I'd also like to stay tight with mom. I've been going home for a weekend about every 3 ore 4 weeks. I'd like to keep to that schedule, depending on if your dad is visiting, of course."

"When I saw you two diving, it looked like two honeymooners. It was so obvious you were in-love. Then you let me know she was actually your mom, that surprised me. You intimated you are a little closer than a normal mother and son, that depending on the definition you are in-love. I also saw how you reacted to dad and your mom dancing. Happiness, not jealousy. You really do want the best for each other. I've been thinking about this, I don't want to get between you two. Whatever you have going on, I don't need to know about. Everybody has baggage in their past. What I DON'T want for us is to lie to each other, ever. What I'm saying is there are things you don't need to know about me, my past, and probably things in your past I don't need to know. Whatever relationship you had with your mother, have with your mother, is not a threat to me. And I don't need to know any details, if you choose not to tell me. We both ended up in Hawaii, sleeping with a parent, for god sake."

"Wow. Now that's the way to start a relationship. Get it all out there from the start. And I really agree about the no lying part. Course, I may not ALWAYS volunteer the full details. But if you ever ask me a direct question, expect the truth back. One more good thing about being with you. If you ever ask me how you look, in anything, I have no reason to not tell you the truth. Fabulous."

Three weeks later.

"'Mom, time for a visit. Are you free this weekend?"

"Actually I am. So Susan is not keeping you busy enough? Need some home cooking? And is she doing your laundry now?"

"Finally, no lectures about finding a woman. Susan is actually going to spend some family time with her dad this weekend. All good."

Next night, Jason got to Tracy's.

"Mom, where do you want me to put my bag?"

"Well now, that's a loaded question. I guess my room, don't see any reason to change, for now."

"I was hoping you would say that. Seems like every time we are together lately it's a new normal, new rules."

Over dinner.

"OK mom, time for the low-down on you and Susan's dad. I've been trying not to pester you too much, but I'm here now. Details? Have you been together much? Susan said he was out of town last weekend. Is your house out-of-town?"

"Yes, Keith was here last weekend, and we had a good time. We're still getting to know each other. He calls a lot, but last weekend was the first time we could reconnect in person. I'm really starting to like him. The distance is good and bad. Good that we can slow down things, bad that he's not here."

"So when you say slow down, does that mean he put his bag in the guest room?"

"No. After the last two days in Hawaii, any guest room stuff is out the window. We're just enjoying each other, seeing how things play out. Not making any plans. How are you and Susan doing?"

"Great. We get to see each other every day at lunch. And she also wanted to back off a little. So we are kind of dating at the moment, but definitely exclusively. Not that we don't SEE a lot of each other. We only live about 10 minutes apart, so that's convenient. Mom, does Keith talk about Susan at all? Did you ever get a vibe that there might be something between them, more than fatherly? I know we have no room to talk in that regard."

"Well, they do seem close. Hard to tell. Do you know something?"

"We had a 'we need to talk' conversation, but in a good way. Susan just wanted to clear the air before our relationship. She is really big on having no lies between us, which I agree with. She said we both probably have secrets in our past, better left there, that the other might not need to know about. Then she talked about you and I. Our relationship. Whatever we have going is not a threat to her, and she is OK with, and does not need to know any details about. Most women would feel threatened, could feel threatened, about a close mother and son relationship. But if she had the same deal with her dad, would she be more understanding about us? And we had another conversation at the luau that was, interesting. Talking about the difference between love and being in-love. We both agreed that, depending on definition, we could not rule out being in-love with our parent. I know you have thought about this, I know I have. Just what is our relationship, currently?"

"Well, you found Susan, but here you are back home, right on schedule. And I found Keith, but I'm always happy you're here. So Susan suspects something between us, but is OK with it. Makes me wonder if Keith is like minded. Our current relationship? I would say, in development. Things are happening, changing, so fast. In the past I had a set of barriers between us, keep us on the level, as it were. Mothers and sons are not supposed to be more than intimate, we both need to find someone else, what happens if Karen finds out. One by one the barriers are coming down. There is nobody left to feel guilty to, ashamed to. One detail about last August I never told you about. You said you were sad we were not more connected that night. After I woke up that morning, remembered what had happened, I went out to the kitchen. I found the calling card you left me. I was going to throw the cigarette pack away, then on a whim I took one out and lit up. It was mostly a way to connect with you, even after you left. Kind of like people used to light up in bed after the fact. I thought a lot about that night these past few months. Playing the game, pretending we didn't know. Part of me was hoping you would push the issue, make love to me again. But, as always, you were the good son, and I was trying to be the good mother. And what happened in Hawaii was payback, so that was OK. Well, OK in my mind anyway. So that leaves us here, now. Like I said, we'll see what develops."

As is customary, Friday night was movie night. After dinner Jason and Tracy assumed 'the position' on the couch, beer and wine close by, and started a movie. Jason laying back, Tracy curled up on his chest. Both just felt, right. Jason's arm wrapped around Tracy.

15 minutes into the movie Tracy's hand started to wander. Idly stroking across Jason's chest. Eventually her hand happened across a nipple. Little strokes, back and forth. Not lost on Jason. Encouraged, Jason started some wandering of his own, landing on one of Tracy's breast. Tracy looked up at Jason, moved up the couch and kissed him. Slow and long. Then more kisses.

"Jason, I was thinking. If we ever decide to be 'more than intimate' again, can you call me Tracy? While it's going on? Like in Hawaii. Mom just doesn't seem, appropriate."

"Sure mom."

After a few more kisses, a little more wandering hands, a little more thinking.

"Tracy, I'm thinking I'm about ready for bed."

"Sounds like a fine idea." Whatever barriers were left between Tracy and Jason were now gone. "Can you give me a couple minutes to get ready? I'll call you in."

Tracy had thought about this possibility, this moment. She knew her and Jason had enjoyed their previous encounters, but that he needed to stay connected with her. What better way to connect and interact than to play games. Role playing games, if possible. And she wanted to connect with the previous sessions, bring them forward, but altered. Jason really seemed to enjoy being under her wrap on the beach. And Tracy had really enjoyed her time with her toy and Jason.

Tracy took off her jeans, and blouse and bra, leaving her panties. Then put on a tight short-sleeve sweater top and a long flowing, pleated skirt. Then she called Jason in.

Tracy commanded "Take you clothes off. Now."

Jason stripped. They were now standing, looking at each other.

"Down on your knees."

Jason knelt in front of Tracy.

"Do you like my panties?"

"Yes Tracy."

"How do you know? Can you see them?"

"No Tracy".

"Do you want to see them?"

"Yes Tracy."

"I'm going to show you my panties. In fact, I want you to take off my panties. Would that be fun?"

"Yes Tracy."

"Do nice boys touch girls panties?"

"No Tracy, nice boys don't touch panties."

"Well then, how are you going to take the off?"

"I don't know Tracy."

Tracy moved in closer to Jason. She lifted her skirt and Jason moved in, up against Tracy. She let the skirt go, trapping Jason under. Memories of Hawaii came back to him. The intoxicating smell of Tracy.

"Jason, take off my panties. Remember no hands."

Jason maneuvered up to Tracy's waist. On one hip, he used his tongue to get under the panties waistband, then could use his teeth to pull the panties down, 2 inches on one side. Then the other side, 4 inches down. Jason worked, back and forth, till at about her knees the panties loosened and fell to the floor. Jason then moved back to her pussy, using tongue where he could reach.

"Jason, stop that. I didn't say you could do that. Who gives the orders here?"

Tracy stepped back from the kneeling Jason.

"You do Tracy."

"Good boy. Now get up and lay in bed, on your back, head on the pillow."

Jason did as requested. Tracy got on the bed, on her hands and knees and maneuvered her pussy over Jason's face, spreading out the skirt all around, again trapping Jason. The lights were still on in the room, and enough light shown thru the material that Jason could see what was coming.

She then lowered herself onto Jason's mouth. Gently. Jason couldn't really move much, so Tracy did. Moving her pussy back and forth, up and down, in and out. Whatever felt good. Jason assisted as well, extending his tongue as far as he could. Then she stopped. Jason was liking this more and more. More aspects of their last meeting, but different. Why did she stop?

"Jason, that is a very little penis."

"That's my tongue Tracy."

"I see. Then where is your penis?"

"It's behind you Tracy."

Tracy turns. "Very nice Jason. You really are a big boy. Are you a good boy or a bad boy with your penis?"

"I'm a bad boy Tracy."

"That's what Tracy wanted to hear."

Tracy, still on her hands and knees, moved back down the bed. She positioned herself over Jason's, at the moment, very erect member. She again spread the skirt around herself as far as it would go, covering Jason's lower chest and upper legs. Starring intently at Jason, she slowly lowered herself. Eventually resting on Jason's crotch, and her ankles. She moved her hands to Jason's chest, starting a slow, long rhythm. Every time she moved up, and out, the skirt would tent around Jason. When she moved down, inside, the skirt would lay flat.

Jason had always had a thing for seeing women in skirts and dresses. Something about the feminine aspects. The being exposed, not knowing what was underneath but, from the right angle, could be seen. A game between man and woman. He thinking about what she might be hiding, was she wearing panties, what they would look like, hoping to catch a fleeting glimpse. She doing everything she can to hide herself. Crossing legs, holding the hem in a wind, being oh so careful sitting or standing, getting into a car. Sometimes letting him get a glimpse, on purpose. Seeing Tracy on him. Him in her. All hidden by the skirt, but knowing, at this moment, exactly what she is hiding. The tight sweater, with no bra, added to the experience. Jason could see the true shape of her breasts, and they would jiggle every time she went up and down. Hidden and exposed at the same time. Yes, this was working for Jason. He would not, could not last long.