The Windy Pines, My Fourth Summer, Part Two
Copyright© 2025 by Fanlon
Chapter 23
Coming of Age Sex Story: Chapter 23 - The Conclusion of The Windy Pines Saga Sam's now at Camp without his family. After what happened with Mom right before he left, he's got a lot of thinking to do, and a lot of wondering about what the future holds. Between the other campers and some visiting friends from his parents' youth, it might be a wild summer...
Caution: This Coming of Age Sex Story contains strong sexual content, including Mult Teenagers Consensual Fiction Incest Mother Son Brother Sister Father Daughter Grand Parent Group Sex Swinging Nudism Slow
When we got out of the shower, Sheila insisted on drying me off. I didn’t mind that at all. I think she was a little disappointed that I didn’t get hard again, especially since she took very good care and was quite methodical in how she dried my dick and balls.
Satisfied with her work, she smiled and held her arms and legs out and waited for me to do the same for her. I grinned and she started giggling.
When we were both thoroughly dried, the two of us headed out into the main room of their cabin. We were both surprised and not surprised at what we found, Shawn and Stephanie were going at it on their bed. Stephanie was on her back, knees splayed wide with Shawn on top of her. Stephanie was small enough that Shawn’s body all but hid her, except for where her arms were wrapped around his neck and her legs wrapped around the back of his thighs.
“Let’s let them have their moment,” Sheila said, taking my hand and leading me to the front porch.
“You don’t want to stay and watch?” I asked, a little shocked that she didn’t.
“Oh, I’ve watched those two more times than I can count,” Sheila replied. “I don’t need to watch them every time.”
“That shower was a lot of fun,” Sheila said, smiling as she took a seat next to me on the swing.
“Yeah, it was,” I grinned and nodded emphatically.
“It’s been a while since I got to have fun with someone Shawn’s age other than Shawn.”
“Oh?” I asked, trying not to show how interested I was in that comment.
“It’s not like I could just have my way with any and every boy in town whenever I wanted,” Sheila sighed, leaning back into the porch swing. “Of course, you already know what it’s like,” The genuine smile on Sheila’s face was beautiful and I returned it in kind without thinking. “I bet your house is even wilder than ours. Even if your parents are only half as sex crazed as they were when we grew up, I still can’t imagine how much fun you all have every day.”
From what I had learned so far about Sheila’s family, mine was absolutely, positively, nothing like theirs. Okay, there were some things we had in common, maybe more than some, but there was one massive thing that separated her family from mine. Sex. Full on, mouthwatering, balls draining sex.
“You have that look on your face again, Sam,” Sheila said, looking at me quizzically.
“Huh?”
“You look like you’re off in another world,” Sheila snickered.
“Oh, umm, Sorry?”
“Don’t give me that,” Sheila waved away my words. “What’s really going on?”
I didn’t say anything, just looking at her and the longer that dragged out, the more Sheila’s brow started to furrow.
“Seriously,” Sheila said, this time more seriously. “What’s going on? Did I do something wrong?”
“What? No!” I hurried to answer. “You didn’t do anything wrong. In fact, you did everything just right!” Sheila’s look softened but she was still waiting for some answers. “I, um, we, my family,” I tried to swallow the lump that was rapidly forming in my throat. “You see, we don’t do...”
“You don’t do ... what, exactly?” Sheila asked, her voice suddenly sharp and accusing and then her eyes got really big. “No!” Sheila’s hands flew up to cover her mouth. “No way, I don’t believe you.”
I didn’t know what to say. Was I supposed to just blurt out, “yeah, my parents don’t have sex with us like you and your kids do...” I wasn’t sure about a lot of things in my life, but this one I was absolutely certain wouldn’t garner a good response.
“You’re serious, you and your mom never?”
I shook my head.
“What about your dad and your sister?”
I was pretty sure they weren’t having sex. I would have told Sheila absolutely not, but Mom had explained that Sara and our dad had been having their own fun while Mom and I had our coffee sessions. They could have been, for all I knew, but Sara and I had agreed no more secrets, and it was a pretty damned big secret that she was blowing Dad the whole time and never told me.
“From what I know, nope,” I answered, shrugging.
“Wow, I can’t believe it!” Sheila exclaimed. “You and your sister though...?”
“Yeah,” I nodded. “But now that she’s going to college, I don’t know anymore.”
“Just because she’s going to college doesn’t mean anything.”
“She has a boyfriend she is really serious about,” I explained. “He has no idea that we’re even nudists, let alone ... other things.”
“Ohh, I see,” Sheila nodded, as if she understood fully what I was saying. “I’m sorry, Sam.”
“Yeah, it kind of sucks,” I replied. “But I’m happy for her though, you know?”
“That’s good to hear,” Sheila smiled sympathetically. “It’s always hard when kids grow up and leave our community, so I get it.”
We sat together, enjoying the warmth of the day for a few minutes, neither of us talking.
Sheila started shaking her head and chuckling out of nowhere.
“What?”
“It’s just that...” Sheila paused. “You and your mom never did anything?”
“Well, we did have coffee in the mornings,” I replied.
“Oh!” Sheila leaned forward, suddenly interested, and grinning widely. “I know exactly what coffee in the morning means. Your dad loved his morning coffee with your grandma.”
“That’s what I’ve heard,” I smirked, jokingly.
“If you don’t mind me asking, what happens when you have coffee in the mornings?” Sheila asked. “I mean, obviously you’re not having sex, but you’re doing something though, right?”
“Well,” I suddenly felt incredibly shy and nervous. I hadn’t ever talked about what happened between me and Mom. Sure, Sara knew, but I didn’t have to come right out and tell her. Even then I wasn’t exactly forthcoming. “We just kind of ... took care of ourselves, but together.”
“You masturbated with your mom?”
The way she so casually threw that out there stunned me. I couldn’t bring myself to answer her. Even though she already knew, I just couldn’t get the words to form in my mouth let alone get past my lips. I nodded.
“I am going to go out on a limb and wager you wanted more than just having her watch you jerk off. Am I right?”
My jaw just hung there as I nodded in answer to her question.
“Did you ever try to do more than just masturbate together?” I nodded again, and I could feel the heat rising in my cheeks. There was no way she wasn’t seeing me blush at her questions. “Breathe, Sam. It’s okay,” Sheila smiled, resting her hand on my leg trying to comfort me. “You’re not going to get in trouble and if you want me to keep it between us, we can do that. Okay?”
Hearing that she would keep my secret, I let out a sigh of relief. I trusted her. I just knew she wouldn’t share whatever it was that I told her. With that in the back of my mind, the flood gates opened, and I started telling her everything.
“And then, right before I came to camp, we did it.” I explained, lost in the telling of my story. “It was incredible. It was an accident, and I didn’t mean for it to happen, but once it did, I couldn’t stop.”
“Oh my,” Sheila gasped. “Then what happened?”
“I thought she was going to kill me!” Sheila giggled at that. “But she held me there. Her hands were holding onto me and there was no way I could pull out.”
“She loved it,” Sheila smiled. “Trust me, I know. She was just overwhelmed and the worst thing you could have possibly done right then was pull away. You did the right thing.”
“Really?” I questioned, remembering the look in Mom’s eyes after the fact.
“Mhmm,” Sheila gave me a soft, warm smile.
“If you say so...”
“How about this, since you told me a secret, I’ll tell you one of mine.” Sheila said. “When Shawn was younger, he used to run around the house with an erection all the time. We couldn’t get him to stop playing with his dick back then.” Sheila paused for a moment, smiling. She was obviously remembering those days fondly. “He was always telling me and his sisters that he was the man of the house. The girls just laughed at him and told him ‘Daddy was the man of the house, not you,’ but that didn’t stop him at all.”
“One day, I decided to see just how serious he was and if he really wanted to be the man of the house.”
“What did you do!” I asked, desperately wanting to hear the rest of this story.
“I told his father what I was going to do beforehand, and he laughed, but told me to go for it. So, that night, I found Shawn in the living room watching the television and playing with his dick. I sat right down next to him and watched for a few minutes. He loved it, and still does love it, when people watched him jerk off. So, I was sitting there watching him and asked him, ‘Do you really want to be the man of the house?’”
Sheila had my total, undivided attention and she grinned at me, knowing she had me in the palm of her hands.
“To no one’s surprise, he puffed up his chest and said, ‘Of course I want to be the man of the house.’ So, I told him that the man of the house had certain ... responsibilities.”
“Ooh!” my eyes went wide.
“Ooh’s right!” Sheila snickered. “I looked him right in the eye and asked if he was sure and he nodded. So, then I reached over and wrapped my hand around his dick and started stroking him. He just about lost it the moment I touched him, but I am proud to say he managed to hold off for a bit...” Sheila giggled. “I opened my legs and started rubbing myself in front of him. I didn’t need to; I was already incredibly turned on because I knew what was going to happen. Shawn, though, he had no idea.”
“Was that the first time you two had sex?”
“Mhmm, it sure was, and let me tell you, as a mom, there is nothing in the world like the feeling when your son puts his hard dick inside of you for the first time!”
“Holy shit!” I gasped.
“Exactly. I don’t know how to explain it, it’s just magical. The thing was, it was the first time for me too, so we were in the same boat. When I got him lined up with me and I felt him enter me. It’s like I found something that I had been missing and didn’t even know it. It’s really hard to explain, Sam. When he came inside of me, I was in heaven. God, it felt so good to feel his warm come as he squirted inside of me.” Sheila sighed, her eyes lost focus as she relived the moment. “What I can tell you, without a shadow of a doubt, is that your mom loved it when she felt you inside of her. I know she did.”
“Then why would she tell me we had to stop!” I almost cried.
“Sam, listen to me, okay?” Sheila said, softly. Her hands cupped my cheeks as she pulled me closer to her. “She loved it, and I can promise you she is thinking about that moment every single day, all day long. She won’t ever be able to forget it. Honestly, Sam, it probably just scared her.” The color drained from my face. “No, no! Not in a bad way. In a very, very good way.”
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