The Windy Pines, My First Summer
Copyright© 2021 by Fanlon
Chapter 29
Coming of Age Story: Chapter 29 - 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
I woke up feeling light on my feet and amazing. There was an obvious bounce in my step as I went to the bathroom first thing when I woke up. I flushed the toilet, washed, and dried my hands and headed out to the porch.
“Good morning, were you just whistling?” Mom asked with a huge smile on her face.
“Was I?” I answered all smiles.
I didn’t even realize I was whistling. Hopefully, I didn’t wake up Dad and Sara. I sat down next to move, angled slightly in her direction, leaned back, and kept my legs slightly apart. I didn’t grab for my cock this morning though, I just lounged next to Mom feeling amazing.
“Aren’t you going to jerk off this morning?” She asked after we had been sitting there silently for a few minutes.
“I am saving it for Jenny later.” I beamed.
Mom just laughed, “I would suggest that you not wait.”
“What, why should I do that?”
“This is going to be your first time, Sam. Your body is going to be overwhelmed and you are going to orgasm really, really quickly.”
“I have heard people talk about their first times before. Some had said they came way too fast, but there were others that said they lasted until they gave the girl an orgasm. I think I will last until Jenny has an orgasm.”
Mom started laughing so hard I thought she was going to fall off of the porch swing. She had tears in her eyes from laughing so hard and her boobs were bouncing all over as her whole body reacted to her laughs.
“Sam, I’m sorry,” She tried to suppress her laughing to talk to me. “I would bet you a lot of money that the boys that said, ‘I made her cum before I did that first time’ are lying and haven’t ever had sex. They most likely have never seen a girl naked in person.”
I didn’t know what to say to that. I could clearly remember one of the cool kids at school bragging about it before summer break. If there was anyone having sex already and would know, it would be that guy.
“Let me ask you this, Sam. How close were you last night when Jenny was sitting on your lap?” I flushed a deep red. “I could see your cock between her legs, Sam. I could see the precum spilling out of your erection.”
“Yeah, I was close Mom. Really close.”
“And you think that won’t happen again right away when you first time you feel the insides of a Jenny?” she paused to gauge my reaction. “You will. You will finish long before she ever does. The first time is not near as good as the second or the third.”
“So, it will help if I come now though?”
“Yes, it will. Trust me. But you will still go too quickly, but this will help a little.”
I nodded and moved my hand around my cock and started to stroke slowly up and down the whole length of my shaft. If this could possibly help me later with Jenny, I was going to slowly build myself up to as big of an orgasm as I could.
“I wanted to talk to you about when you and Jenny do, do it,” Mom said while she watched me masturbate. “What do you know about girls and what happens when they lose their virginity?”
“I know she has a hymen that will break when I first go inside her.”
“Close, but not quite true.” Mom paused with a thoughtful look on her face. “Jenny uses tampons, and I am sure you have fingered her right?”
“Yeah, I have.”
“Then most likely she has already lost her cherry.” I looked at her confused. “That doesn’t mean she isn’t a virgin. She is. But there won’t be much pain like there would be if she still had her hymen. You still need to go really slowly. Fingers are not at all the same as a penis.”
“Okay, I understand.” that was a weight off of my mind. I was worried about it hurting her because she had said that her first time with my cock would be better for her. But from what Mom was saying, that might not be a problem after all.
“Make sure she is really turned on and very wet first. Start with your fingers, okay. If you think you want to, you can even use your tongue. She will love that if you do.”
I had a huge grin on my face when she brought up me possibly licking Jenny’s pussy. Mom looked at me for a second before her eyebrows went up in surprise.
“You’ve already done that, haven’t you?” I nodded with a grin on my face. “Well, do that again before you try to put your dick in her.”
I was getting really close now to orgasming, and the talk of sex was spurring me on.
“I’m going to come, Mom.”
“Go ahead.” Mom shifted a little and her focus was now solely on my cock.
“Ugnn,” I grunted as my balls released my come and it rocketed out of my cock and landed right in front of Mom. It didn’t reach her this time, but it was a near thing.
“That was a big one, that should help some later.” Mom smiled at me. “Go take a shower.”
I got to the bathroom just as Sara was coming out, soaking wet and towel drying her hair.
“Good morning, Sam,” Sara said with a wink.
“Morning.” I answered.
After my shower and a quick breakfast Sara and I did the dishes like we do after every meal. When Dad brought us his plate to us, he told me to meet him on the porch when we are finished cleaning up. I didn’t know what he wanted but I wanted to get whatever it was over with as quickly as possible so I could meet up with Jenny. Sara looked at me and shrugged letting me know she had no idea what that was all about.
“Me and Jenny will hand out for you outside with Mom until you are done talking with Dad.”
“Sounds good, thanks Sara.
When Sara put away that last of the plates she smiled and headed outside to meet Jenny. No doubt she was already here and anxiously waiting for Sara and me to come outside. I dried my hands on the dishtowel and followed a couple steps behind Sara. Dad looked up when he heard Sara open the door and stood up when I stepped outside.
“Come on, Sam.” Dad said and waved for me to follow him.
Jenny was standing there on the steps with a worried look in her eyes as I followed Dad down the steps and started walking away. The two of us only walked a dozen paces before Dad started talking.
“Today is the day huh?” He looked down at me and asked.
“Yeah, it is,” I answered as we walked.
“I am proud of you, Sam.” He wrapped his around over my shoulder and pulled me close in a one-armed hug.
I chuckled and said, “Thanks. I am really nervous.”
“You should be, this is a really bid deal for you. Even more so for Jenny.”
“That’s what Mom told me too.”
“Listen to her, she is a very smart woman. Its one of the main reasons I married her.” Dad smiled big and proud as he said that about Mom.
“I will.”
“Good, you’re a good kid Sam. There are a couple things I wanted to tell you before you headed off with Jenny and your sister.” We both stopped walking. “First, you need to take a blanket with you. I set one out for you by your bag. Secondly, do not forget your condoms. No condom, no sex, period. Do you understand?” I nodded my acceptance.
“Now for the most important part. Always be gentle when you are with a girl. She may ask you to be firmer, rougher, but you need to be gentle first and foremost.” He put both of his hands on my shoulders and looked me in the eye. “Especially when its her first time. Sometimes it hurts the girl and sometimes it doesn’t. You won’t know until you start having sex. Its better to be safe rather than sorry.”
“I think I understand, Dad.”
“I’m sure you do. You also need to show her respect. If Jenny or any other girl tell you no, stop. You don’t push further, you don’t try to convenience them to keep going, you stop, no matter what, okay?” I nodded.
There was a firm, seriousness to his tone that told me I would be in serious trouble if he ever found out I had no listened when a girl told me no. If I wasn’t nervous enough by now, I was almost to the point of panic. Dad saw the chance in my face and chuckled softly.
“You will be fine today. Have fun, you only get to experience it for the first time once. Its going to be incredible and nerve wracking all at the same time. Go slow. That’s the best advice I can give you. I don’t think Jenny will let you go slow but try to if you can.”
Dad ruffled the hair on my head, and we turned and headed back to the cabin where Sara, Jenny, and Mom were waiting for us. When we got back to the cabin, Jenny and Sara were all smiles and Mom had a mischievous grin on her face as well.
“You didn’t try to teach him any of your moves, did you?” Mom asked Dad.
“No, not yet. I will soon though.” Both Mom and Dad busted out laughing after Dad’s comment.
“Your moves don’t work at all. You think they do, but that doesn’t mean I do.” Mom said still laughing.
Dad feigned a shocked look and that made Mom roll her eyes and Dad started laughing.
“You kids get going before I have to show your dad a thing or two.” Mom announced.
“Let’s go before they drag us into it.” Sara said.
“Give me one second.” I said and ran into the cabin to get the condoms and the blanket Dad said he left for me.
When I came back out with the blanket in my arms and the condom box stuck in between the folds Sara smiled and Jenny said, “Aw, you’re so sweet.”
Jenny looked to my parents who were both smiling but didn’t say anything except, “Be back for dinner.” Mom called out as we started walking away. Both the girls were walking a step or two behind me as I led them to the spot, which I thought would be perfect for our first time.
When we got to what I considered to be, our spot, I quickly unfolded the blanket and spread it out in front of the fallen log we had used a few times before. This was as private of a spot as we could find in the camp. Next year, there would be a lot more options but this year, this would be perfect.
All three of us sat on the fallen tree trunk and no one said a word. All three of us appeared to be really nervous and no one wanted to say anything. I sat in between both girls, Jenny on my left and Sara on my right. Both girls were snuggled in tight, and I could feel the softness of their boobs pressed against my arms.
I pulled both of my arms out from between the girls and wrapped them around both of their middles. I pulled them both close and my hands found a boob on each of their chests. Jenny and Sara giggled and slid in closer to me as I pulled them to me. I could feel both of their nipples were very hard in my palms. Jenny turned her head to me and kissed my check sweetly. Sara though, reached up, grabbed my face, and planted an incredibly hot kiss on my lips.
The kiss grew in passion as it continued, both of our tongue probing and exploring the others mouth. When we pulled apart my heart was racing, and Sara’s face and chest were flushes.
“My turn!” Jenny exclaimed and grabbed my face and turned it to hers as she planted a searing kiss on my lips as well.
I was out of breath by the time we pulled apart and if I hadn’t been hard already, I would have been as solid as a steal pipe now. Jenny then surprised me when she got up and then sat down in Sara’s lap. I don’t think Sara was expecting it either but when Jenny’s lips met hers, she fell into Jenny right away and got lost in the deep, passionate kiss. Watching Jenny and my sister make out was amazing. It was far and away the most erotic thing I had ever seen and each time they did it, I just sat there and watched transfixed.
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