The Windy Pines, My Fourth Summer, Part Two
Copyright© 2025 by Fanlon
Chapter 32
Coming of Age Sex Story: Chapter 32 - 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
There was excitement in the cabin that felt almost physical. My heart was racing, and it felt like someone was squeezing my chest. I couldn’t believe what was happening. Michaela had made a ridiculously crazy bet. Shawn was going to get to have anal sex with Michaela if she lost the next hand. What!
I was sure there was more to that story than what I knew already, but whatever that story was, it was more than enough to make Shawn jump to agree and push in his pile of pretzel sticks. Anal sex versus pretzel sticks, holy shit!
My eyes kept racing from person to person as Jeff slowly shuffled the cards for the winner-take-all hand of Texas Hold’em. Shawn, with Stephanie standing right behind him rubbing his shoulders, was all eager smiles as he waited for his dad to deal out the cards. Michaela, however, looked determined and angry.
I did find it curious that Michaela had done something extremely similar to what Stephanie had done at the miniature golf course. Stephanie offered me a blowjob to miss a putt so she and Sheila would win the match against me and Shawn. Michaela did nearly the same exact thing. One thing was for certain though, this family was competitive and hated to lose.
“Who do you think is going to win?” Mom asked me, her voice low enough that only I could hear her. I glanced at her, and she grinned when my eyes met hers for a moment.
“I have no idea,” I replied. “I can’t believe this is actually happening, it’s crazy!”
“I know!” Mom agreed. “I kind of hope Shawn wins.”
“What? Really?”
“Oh yeah,” Mom grinned even wider, nodding slowly. “Sheil’s, come here!”
“Mom, what are you—” I tried to cut her off, but it was too late, Sheila moved like lightning to her friend’s side.
“Exciting isn’t it?” Sheila tried to squat down between me and Mom but there wasn’t enough room. “Scooch over a bit, Sam.” Sheila offered me a smirk. I did and she slipped in and sat on her heels while placing one of her hands on each of mine and my mom’s thighs. “This whole thing escalated pretty quickly, though I’m not all that surprised.”
“Huh?” I muttered, confused.
“Michaela hates to lose, especially at poker,” Sheila answered. “You should have seen her when Jeff let her join his little weekly card game back home. This was a few years ago, but I will tell you what, she had every single one of the guys wrapped around her little finger and then some.”
“Did she do...” Mom left the rest unsaid.
“Yup,” Sheila grinned. “And she won.”
I was so wrapped up in what was going on, I hadn’t even noticed when Sheila put her hand on my leg, and I still hadn’t noticed when her hand slid further and further up until I felt her little finger brush against the edge of my limp, smooth shaft.
I glanced down at her hand, and she noticed me looking. When I looked back up at Sheila, she just winked, and I felt the blood rush so fast to my cock that I was sure it would have broken some sort of land speed record.
That’s when I noticed her other hand at the top of Mom’s thigh and how Mom parted her legs. I don’t know if it was a conscious reaction on Mom’s part, but the end result was the same. Sheila’s hand went between my mom’s legs.
I didn’t know what to do. I wanted to watch Sheila’s hand as she did whatever she was going to do to my mom. I wanted to watch her other hand as she teased my now rock-hard dick, but I really wanted to watch the card game between Shawn and Michaela too!
That’s when I felt Sheila’s fingers go from teasing my length to wrapping themselves around it, and I moaned. I tried to cut it off, keep it silent so no one would notice, but my mom did.
Her head turned and looked down to see her childhood friend’s hand wrapped around my cock. She wasn’t stroking me, just holding me. When I looked up, Mom’s eyes bore into mine and then Sheila must have done something because they fluttered closed for a long moment as her head leaned back. Her face was flushed slightly, and her nipples were hard. She must be receiving the same treatment I was getting.
My breath caught in my throat, my mouth so suddenly dry that I could hardly swallow and then suddenly, Sheila just ... released me. She got up and walked into the kitchen to pour another glass of wine. I felt like something vital and wondrous has just walked away for no reason. I heard what I swore was a whimper from my mother, but she quickly tried to compose herself. No matter how hard she tried though, there was no hiding the physical reactions she had from Sheila’s touch.
My mom was smiling shyly as she pressed her legs together, running her hands down her sides and onto her legs as if she were smoothing out the wrinkles from an invisible outfit.
“Dana, care for another?” Sheila asked, holding up the bottle of wine.
“Uh,” Mom cleared her throat. “Sure, that ... would be wonderful.”
“Alright you two,” Jeff’s voice called out, grabbing everyone’s attention in the room, not just the two players he was talking to. “Since this is the last hand, do you want me to deal all the cards face up?”
“Sure, doesn’t matter to me,” Shawn replied, still brimming with confidence.
“Fine!” Michaela snapped, her brow furrowed as she stared daggers at her brother who didn’t look even remotely fazed.
“Wait! I’m not ready yet.” Sheila cried out, frantically pouring Mom’s glass of wine, and rushing back over to the table.
Jeff sighed, giving the deck one more shuffle for good measure while we waited.
“Okay, deal!” Sheila said, handing my mom her glass and moving around the table to sit next to Jeff. I had kind of hoped she would come back and sit with me and Mom again, but unfortunately, she didn’t.
Jeff dealt the first card to Michaela face up so everyone could see it. A nine of hearts. Michaela only glanced down at it for a blink before her eyes returned their laser focus back on Shawn. Jeff dealt the next card, the ace of spades.
“Yes!” Shawn exclaimed.
“Don’t act like you’ve won already because you got an ace,” Michaela snapped.
Jeff dealt Michaela her second card, the five of diamonds.
“Nine-five,” Shawn grinned. “Not great, Michaela.”
Shawn’s second card was the queen of spades.
“You’re so going to lose,” Shawn jeered.
No one said a word, but the tension was obviously getting to everyone, Jeff included, because none of us could sit still. Except for Michaela. Somehow she seemed ... okay. She just continued to stare across the table at her opponent.
When Jeff turned over the flop, there were gasps from everyone and then excited cheers from Stephanie in support of Shawn. The three cards Jeff laid down were the ace of clubs, the six of spades, and to make matters even worse for Michaela, a queen of hearts. Shawn had two pairs!
Jeff laid down the next card, a seven of clubs. Michaela hadn’t made one pair; she was going to lose. Shawn got up from his seat, no longer able to just sit there and watch what was about to happen. He started rubbing his hands together excitedly and it wasn’t lost on me that he was fully erect.
“Wow,” Mom said, her eyes homed in on Shawn’s groin.
“Mom!” I hissed.
“What?” she asked. “He’s got a nice cock.”
“It’s not like you haven’t seen it before!”
“Oh, I know...” Mom replied, and I rolled my eyes. “Doesn’t mean I don’t like to look, and don’t roll your eyes at me like that.” Mom gave me a side-eyed look. “I like yours better anyway. Don’t go getting all jealous.”
“I’m not jealous,” I hissed, crossing my arms over my chest. I might have been the tiniest bit jealous.
“I like them smooth, and you know that.”
I just sighed and shook my head turning my attention back to the game as Jeff was flipping over the last card. The river was an eight of spades.
“Holy shit!” Michaela jumped up out of her chair, thrusting both her arms over her head in celebration.
“That’s ... that’s...” Shawn was stunned.
It took me a second to realize what had just happened, but when I saw it, I just about fell out of my chair.
“I win!” Michaela started jumping up and down. “I win, I win, I win!”
“Sorry Shawn,” Jeff said as he collected the cards. “I thought you had her.”
“I ... lost ... how?” Shawn suddenly just sat down right there on the floor, slack jawed and his eyes looking vacant. As if what had just happened was too much for him to process.
Somehow Michaela had gotten a straight and won the hand. It was the luckiest, most bonkers ending to a card game I think I had ever seen. Not to mention the stakes that she had put up, which only made it that much more ridiculous.
Michaela was on Cloud Nine and for good reason. She raced around the room yelling how she won, and she gave each and every one of us a huge enthusiastic hug. Everyone except Shawn that is.
It took a while for Michaela to calm down, but she finally managed it with a little suggestive help from Jeff. She was a little over the top about the whole thing. Not that I wouldn’t have acted any differently if I were in her shoes.
“So, what are we going to play next?” Michaela asked, full of energy and excitement.
“Nothing for me,” My mom replied before anyone could suggest anything. “I need to get some sleep. I think I’ve had one too many glasses of wine.”
“But it’s still raining!” Michaela complained, not wanting another player to leave.
“Are you sure, Dana?” Jeff asked.
“Yeah, I should be getting back.”
“Can Sam stay with us tonight?” Stephanie asked, racing over to stand at my side.
“Sure, if that’s okay with your parents.”
“He’s always welcome and we’ll take good care of him,” Sheila announced, answering the question before it needed to be asked. “Breakfast in the morning?”
My mind raced at the implication of her words. I had no doubt Stephanie, and I were going to have a fun evening, but the thought of Sheila being involved added a little extra ... something. The idea of that ‘something’ I liked very, very much.
“Of course, assuming I wake up without a hangover.” Mom smirked and Jeff and Sheila chuckled knowingly.
“Make sure you drink some water when you get back to your cabin,” Jeff said.
“Are you sure you don’t want to stay, Mom?” I asked.
“Oh no,” She answered. “I’ll see you in the morning for breakfast.”
With that, Mom said her goodbyes and headed out into the rain. Thankfully, she didn’t have far to go, and the rain had let up considerably, but that didn’t mean it had stopped by any means. Still, a little rain wasn’t going to stop her.
“Alright, what are we going to play?” Michaela asked again when my mom had left.
“No more cards!” I answered and that got everyone laughing except Shawn, who was still sitting on the floor in a stupor.
“I have an idea,” Sheila said. “How about Truth or Dare?”
“Oh, come on,” Michaela groaned. “Truth or Dare is lame.”
“Why is that?” Jeff asked, his voice accusing.
“We all know each other’s truths,” Michaela replied quickly.
“Sam doesn’t,” Stephanie answered. “Unless you don’t want him to know about your dirty secrets.” That gave Michaela pause, which surprised me. “I think Truth or Dare could be fun!”
The six of us all sat around the table, including Shawn. He was finally starting to come out of his stupor but wasn’t his usual self quite yet.
“Alright, let’s start with the rules!” Stephanie announced, obviously excited to get the game started. “You are only allowed to pick Truth twice. That’s it, no more than that. The rest of the time, it’s all Dares.”
“Oh, come on,” Michaela complained. “Seriously, can’t we play something else? It’s no secret that Stephanie is just looking for a reason to fuck Sam in front of everyone.”
“Do you have another suggestion?” Sheila asked.
“Well, we finally have an equal ratio of guys to girls,” Michaela explained. “What if we played ... Spin the Wheel?”
“We didn’t bring the wheel,” Sheila replied very matter-of-factly.
“I did,” Michaela grinned.
“You what?” Stephanie exclaimed. I couldn’t tell if she was happy or angry about ‘the wheel’ but either way, I wanted to know what it was.
“I’ll be right back!” Michaela jumped up and went to rummage through her bag and pulled out what looked like the spinner from the game Twister. “See, told you!” Michaela cheered, holding it up for everyone to see. Jeff started chuckling as Stephanie’s jaw dropped. The corners of Sheila’s mouth curled up dangerously. “Okay, who is going to get the first spin?”
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