The Windy Pines, My First Summer - Cover

The Windy Pines, My First Summer

Copyright© 2021 by Fanlon

Chapter 20

Coming of Age Story: Chapter 20 - Me, my sister, my mom, and my dad take our first family trip to The Windy Pines. A clothing optional resort/camp owned by my grandparents. One can imagine what would happen to a pair of kids at a resort like this, for the first time. This is a coming-of-age story of a boy who is initially uncomfortable with his nudity, for good reason, but learns that with a specific friend or two, it might not be that bad. Maybe. Winner of 2 Clitoride awards in 2022 and a finalist for a few others.

Caution: This Coming of Age Story contains strong sexual content, including Ma/Fa   mt/ft   mt/Fa   ft/ft   Mult   Teenagers   Consensual   Reluctant   Fiction   Incest   Mother   Son   Brother   Sister   Daughter   Exhibitionism   First   Masturbation   Oral Sex   Petting   Safe Sex   Voyeurism   Big Breasts   Size   Small Breasts   Nudism   Slow  

After a while, I picked myself off the ground after getting an amazing blowjob from Jenny. Both girls had a bounce in their steps as we headed to the pool area. Our exploring wasn’t what I had in mind, but I wasn’t going to complain. I still wanted to see the rest of The Windy Pines camp, but that would have to wait for another day. Sara and Jenny pulled ahead of me as we walked. Both girls were talking quietly and then giggling. They would both occasionally look back at me, and then whisper something else, which would again bring on more giggles.

Instead of asking what they were talking about, I slowly sped up my pace to be closer to the two girls. I was only about a step behind them when I heard Jenny whisper something that made me stop in my tracks. To make matters worse, Sara nodded her head in agreement. “Holy shit,” thought to myself. Sara and Jenny walked another dozen steps before they realized I had stopped.

“Hey, what are you doing?” Sara looked at me and then waved me forward. “Let’s go, come on.”

Jenny gave me a weird but confused look as I just stood there stock still.

“Are you okay Sam?” Jenny asked, concern on her voice.

When I didn’t respond, she hustled back to where I was standing and physically shook me. That brought me out of my stupor.

“What?” I asked, looking at Jenny as she stared at me.

“You were just standing there and not moving. You didn’t even blink. It was kind of scary.”

“Oh, um. Yeah, I mean. I’m fine,” I said, stumbling over my words. “Do you really—” I was going to ask her if she really meant what she said, but I stopped myself.

Her brow creased as she tried to figure out what I was going to ask. Eventually Sara grabbed Jenny’s arm and pulled her along towards the pool. I followed again, my mind still reeling.

Jenny had said she wanted me to take her virginity before we left camp. Holy shit!

I desperately wanted to talk about what they said. It was driving me nuts the rest of the day. I tried to get the girls one on one with me to figure out what they wanted but it never happened. Sara and Jenny were joined at the hip. Not once did they separate and give me an opening. I finally came to the realization that I would have to corner Sara later tonight or tomorrow morning before we headed out to meet Jenny. That was fine, I could wait - for now - but I needed to know.

After dinner, while Sara and I were doing the dishes, I asked, “So, is there anything else we want to do before we go home?” What in the holy shit was that question! I chided myself but Sara’s response caught my attention.

“Well, there isn’t much, I don’t think. I know Jenny and I want to enjoy the rest of our time here.”

“So, nothing major planned?” I asked, trying to get Sara to spill what she knew.

“Nope. Just having fun. That’s it.”

“So, you weren’t planning to try to, umm. You know, uh--,” I started to trip over my words. Sara must have caught my meaning because she had a mortified look on her face.

“How!”

“I heard you two!” I snapped back quickly under the pressure of Sara’s gaze.

“Oh. My. God. You heard us. You did, didn’t you!” I just nodded, feeling guilty. “What did you hear?” Sara said that with a hushed voice, not wanting mom and dad to overhear.

“I heard, well, I heard Jenny say she wanted to lose her virginity with me before the two of us went home.” I watched her eyes get bigger and bigger. “And then I saw you agree with her. Do you want to have sex with me too?” I asked, in a voice as quiet as hers had been.

I took a minute for Sara to respond to me, and when she did it was not at all what I was expecting.

“Yes. Yes, to both, actually. You need to talk to Mom and see about getting some protection.”

“What do you mean?”

“Condoms, duh. If you talk to Mom tomorrow morning, she’ll get you some if you tell her Jenny and you are going to, you know, do it.”

“Condoms for Jenny, but you don’t want to do it then?” I wasn’t quick on the uptake at the moment and Sara rolled her eyes at me.

“Yes, I want to have sex with you. Condoms come in packs larger than just one. So, if she gets you a pack of three, one will be mine.” Sara’s eyes were fierce when she said “mine” and I just nodded as I tried to keep the shock off my face.

The rest of the night was uneventful. Sara and I sat on the porch with Mom and Dad and eventually went to bed. We didn’t talk about sex again. The next morning, I woke up knowing I needed to talk to mom. I still felt weird asking her for condoms. I could masturbate in front of her, but heaven forbid I need a box of condoms. I got out of bed, stretched, and then hurried to the bathroom to relieve myself and go meet Mom, who was already waiting for me.

“Morning Mom,” I said.

“Good morning, Sam.” Mom replied with a smile.

I sat down next to my mom, who was taking a sip of coffee. When I just looked at her, she paused, put her cup down by her lap and asked, “what is it, Sam?”

“I need some condoms.” Mom spit out her coffee in a fine mist.

“You need what? Condoms?” she asked, her eyes searching mine.

I nodded. “You said I could talk to you, and you would try to teach me if I needed anything.”

“Yes. Yes, I did. Can I ask who you are planning on needing condoms for?” Mom managed to keep her voice level and almost clinical.

“Come on Mom, you already know.”

“Jenny.” I nodded sharply. She waited for a breath before she asked, “Your sister?”

I didn’t answer her right away. I looked her in the eyes as she matched my gaze.

I took a deep breath. “Yes,” I said.

“I see. Well, your dad or I will have to go into town then. When do you need them?”

“I don’t know. I just know before we leave to go home.”

My mom looked at me and her motherly posture loosened, and she smiled knowingly at me. I didn’t respond to her. I didn’t know what to say at that moment. It was hard enough to ask for condoms and then tell her that not only did I plan to have sex with Jenny, but my sister Sara as well.

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