A Summer of New Experiences Ch. 03

Story Info
Timmy and Jeannie's experiences continue and a trip to Aspen.
9.1k words
4.68
22.4k
23

Part 3 of the 4 part series

Updated 06/08/2023
Created 12/23/2017
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Editor's note: this story contains scenes of gay male sexual content.

Author's Note: Another long pause between updates and I apologize. I'm trying to focus on finishing some stories. Please let me know what you think of this one. Some m/m bisexual content ahead. Consider yourselves warned.

-nosebone

The next morning, I was having the most amazing dream. Jeannie and I were in bed with Katie, naked. We kissed and touched, teasing one another. The girls were stroking my cock. My fingers roamed over their breasts and pussies. It was all just so perfect....

"Wake up, lover boy," Jeannie whispered to me.

"Huh, what," I asked as I woke up.

"That must have been some dream you were having," she said.

As I looked around, I realized not all of it was a dream. Jeannie's small hands were wrapped around my throbbing cock and she was stroking it lightly. I saw she was naked and her hair was wet from the shower.

"Yeah, it was," I admitted.

"You woke me up by rubbing this big, damn thing against me," she smiled.

"I'm sorry," I grinned.

"It's okay," she said. "What were you dreaming about?"

She listened as I explained.

"That might not be just a dream for long, you know," she said.

"I hope not," I said. I realized she'd taken my briefs off.

"I have a little bit of time before we're leaving to go shopping, if you're interested in breakfast," she said slyly.

"Let me brush my teeth, then," I smiled. When I returned to Leslie's room, Jeannie was laying back on the bed, her legs spread. She was lightly touching herself.

"I might just stand here and watch this," I laughed.

"No, you will not. Get over here," she said, biting her lip. "I'm ready, I got so horny playing with you."

"You did, huh," I asked as I knelt between her spread thighs.

"Yeah, this 'taking things slow' is hard, Timmy."

"I agree," I said.

"I, uh, was sucking on you while you were sleeping," she said.

"What? I was getting my first blow job and I wasn't even awake?"

"Haha, yeah. I thought either you were really tired or I wasn't doing a very good job," she laughed.

"I was tired," I said. I leaned down and kissed her sweet pussy lips. I took a deep breath, inhaling her arousal. I looked up and saw her watching as I ran my tongue over her wet folds. She took my head gently in her hands as I savored her taste. I hoped there'd many more chances to do this the rest of the summer. How would Katie taste, I wondered? Would there be that much difference? I couldn't wait to find out.

"God, Timmy, it feels so good. I want to learn to make you feel the way you're making me feel right now," Jeannie cooed.

"Mmmmhmmm," I moaned, my mouth and tongue never leaving her. Her wetness continued to flow and I relished it.

"Oh, that's really nice. Yeah. Right there," she moaned. My tongue circled her hard, little clit, as she writhed on the bed. I loved pleasuring her and imagined things going further. I couldn't believe she'd been sucking me and I hadn't been awake!!!

"Timmy, get up here on the bed with me. I want to try something I saw in one of Billy's magazines."

I did as she requested. I quickly figured it out what she had planned as she rolled over on her hands and knees. She straddled my face as I laid back.

"What do you think," she asked.

"I love it," I replied as I resumed licking her wet sex. Her soft hand gripped my cock and I felt her warm, wet mouth engulf the head.

"Mmmm," I groaned. It was hard to believe I'd slept through that, as good as it felt. Her mouth explored my cock tentatively, much like I had with her brother. It still felt amazing, coupled with the pleasure I was giving her. I circled my tongue around her clit again and felt her grip my cock tighter. Her lips moved faster on my cock, driving me wild.

"Mmmhmmm," I heard her moan. She ground against my face insistently, seeking her release. I wanted to make her cum again so bad. I was getting really close myself as she'd found a rhythm that drove me crazy. Her hips moved erratically and I struggled to keep my tongue and mouth on her. I grabbed her firm little ass cheeks to maintain control of her, as I increased my pressure on her clit. She tensed up, and her mouth left my cock.

"Oh, Timmy. Yes, yes," she wailed. I hoped no one was downstairs that could hear her! My continued licking took her to the edge and beyond. I felt the tension in her body release and she moaned.

"Uhhh, wow," she said as she collapsed on top of me. Her hand continued lightly stroking my cock and I felt her moving. She turned around and straddled my thighs, before resuming her stroking my cock. I was so turned on and hoped she'd finish sucking me. Finally, I asked her to.

"Sorry, Timmy. My jaw hurts. You're really big," she lamented.

"I know. I wished I could have gotten off."

"I know, but I have a better idea," she offered. She moved forward and her wet pussy slid along the underside of my cock. It wasn't as good as her hot mouth, but to my overexcited cock it was the stimulus I needed. She ground her pussy back and forth, smearing her juices and our combined saliva. I was soon lubed up nicely, and she glided over me easily. Her movement was taking her from the head almost back down to my balls. She leaned down and kissed me passionately. Her movement changed the angle of her body and on her next backstroke, my hard cock slipped in her wet pussy. We both gasped in surprise.

"Jeannie, I'm inside you. Get off of me," I said. I scarcely believed the words had come out of my mouth, but she'd asked me to help her take things slow. Her only response was to continue sliding back on my cock.

"Jeannie, baby. What are you doing?"

"What I wanted to do since last night," she replied.

"Are you sure?"

"Yes. Very sure," she replied. Her hips moved slowly working her tight wetness back and forth on my cock. The pleasure was so intense.

"I'm not wearing a condom!"

"I've been on the pill for 5 years. I think we're safe."

"Are you sure," I asked.

"Would you quit asking that? We're already doing it, let's enjoy it," she snapped.

I shook my head as I watched my sexy cousin work herself up and down on my hard cock. It had just happened. I'd tried to stop her, but she'd insisted. We were making love!! I couldn't believe how good it felt, with her warm wetness sliding up and down on me. My hands roamed over her tight young body, feeling her soft, smooth skin. She shivered when my palms grazed over her hard nipples.

"That's really good Timmy. Keep doing that."

"This is amazing, Jeannie. I love you," I replied.

"I love you, too. We'll have the rest of the summer to enjoy this now."

"Yes. We do," I agreed.

The tempo of her hips increased. She was finding her groove as she rode me. I learned that day there was nothing in the world as wonderful as a sexy woman on top of you, riding your cock. Nothing like it.

"Timmy, I think I'm getting close again! Are you," she asked. She looked at me intently.

"Yeah, I am. I've been trying really hard not to. I don't want this to end!!"

"I know. Oh, it's so good and feels so right with you. Oh, Timmy. Oh," she moaned.

"Mmmm, Jeannie. Ah, god. Yes," I gasped as I came inside her.

She leaned forward and collapsed against me. I put my arms around her and held her small frame. We kissed softly and then with more vigor. God, that had been so good, but there was still that nagging thought in my mind.

"You're sure that was okay," I asked.

"Yeah, of course. Do you not think so," she asked in reply.

"I just know what you said last night," I answered.

"I know, but what if we waited any longer? We wouldn't know how wonderful that was."

"That's true," I admitted.

"I can't wait to do it again. We'll always be one another's first," she smiled.

"Yes, we will. I'm glad you were mine."

"Me too. That's what I always wanted. I knew it would be special with you," Jeannie said.

"Yeah," I smiled before we kissed.

"I wish Katie had waited," Jeannie said.

"Oh?"

"Yeah, she went all the way with that guy she was dating after prom," she explained. "She said it wasn't good and really awkward. She hasn't spoken to him since."

"I'm sorry for her," I said.

"Me too, but we can show her how good it is though," Jeannie smiled.

"Yes I hope we can," I agreed.

We were still laying there kissing, when the bedroom door swung open.

"Holy shit," Jeff exclaimed.

"Jeff!! Get the fuck out of here," Jeannie screamed at him. She was scrambling to get the bedsheet pulled over her naked body. Jeff looked back and forth between Jeannie and me. He had a big grin on his face. Finally, he turned and walked out, closing the door behind him.

"Jesus," she groaned. "That was pretty annoying."

"Thank god it was Jeff, and not Granny or Pops."

"That's true. Oh, hell. I need to get to ready," she leaned down and kissed me. "I guess if he asks..."

"He will," I smiled.

"Okay, it was pretty obvious."

I nodded, still smiling at her.

"I love you," she said.

"I love you, too sweetie."

She walked to Leslie's bathroom to finish getting ready. I decided to go take a shower myself. It was just then 8 o'clock. I walked into the bedroom I usually slept in and found Jeff waiting for me. He was smiling and shaking his head.

"Damn, dude. Did you two really...," he asked.

"Yeah. We did."

"Man, that's fucking awesome," he replied.

"Yeah it was."

"Well now that you've gotten laid for the day, Pops wants us to fly up to Aspen with him. He wants to make sure Leslie hasn't torn the place down during one of her parties," Jeff laughed. "He told me to grab some clothes as he wants us to maybe stay a day or two to do some work around the place. He's gotta fly back this afternoon because he and Granny have another banquet tonight."

"Sure, no problem. It's the least we can do for him. Let me grab a quick shower," I said.

After my shower, I got dressed and packed a bag with a few changes of clothes. Fortunately, I had an extra swimsuit so I'd be able to take advantage of the pool and hot tub in Aspen and have to pack my wet suit from the previous night. Jeff told me his bag was downstairs and we headed out. I told him I forgot to grab my wallet as he headed downstairs.

I snuck back into Leslie's room and saw Jeannie standing there in just her bra and panties. I walked over and hugged her. I explained our plans and we exchanged a few more delicious kisses.

"Well damn. I hate that, but you two should go help Pops. We all know Leslie isn't going to," Jeannie sighed.

"I know," I agreed.

"Try not to think about me too much," she smiled devilishly.

"Haha, I'll try not to, baby," I replied.

"I love you."

"I love you too. Bye," I replied.

I met Jeff and Pops downstairs and we headed to the airport. This was always a great experience for Jeff and me, getting to go someplace with Pops in the jet. He was a man that should have had his chips called in a hundred times, but he'd never wavered from being the West Texas cowboy his dad always wanted him to be. We knew we'd get treated to some of his old war stories. Additionally, there were a lot of life lessons thrown in there that I'm ashamed to admit I didn't fully appreciate them until after Pops was gone. I learned them though, often while flying on that Lear Jet.

Pops had called ahead and the plane was already out of the hangar. Being a man that survived countless air battles over France and Germany, he was a cautious one. We walked around the plane several times until he was satisfied. He slipped the guy that had pulled the plane out a $100 bill and we boarded. We were rolling down the taxiway within a minute of getting on board. I loved this kind of flying so much better than flying commercial. Jeff and I slipped on our headsets and listened to Pops talk to the tower. We paused briefly at the end of the runway as Pops brought the engines to full power. I always loved the way the Lear jet felt rolling down the runway. It was so much different than the 727's and MD-11's I was used to flying. In seemingly an instant, we were airborne and Pops began his climb out. He angled the plane to the northwest and we were on our way.

After we crossed the Red River into Oklahoma, Jeff asked Pops about flying over Germany.

"The thing of it was, when I first got over there the Me-109's and FW-190's came in from the tail. That was until we started whipping them pretty good. Then they started attacking from the front and we lost a lot of planes that way," Pops explained.

"What did you guys do," I asked.

"They put guns in the nose of the plane. It helped, but the fighters were always a problem," he explained.

"Gosh, I can only imagine," I said.

"I'll tell you boys, the fighters were bad, but what always puckered my asshole up was that anti-aircraft artillery. I still wake up in the middle of the night in a cold sweat from dreaming about that goddamn flak. We'd be over the target and planes would just blow up. No chance for the crew to bail out. It was a goddamned scary time," he said.

Jeff and I nodded somberly. Soon after, we landed in Aspen. Pops pulled the plane up to his private hangar. Scotty, the airport maintenance guy, pulled in just as we hopped down the ladder.

"Greetings, gents," he said. We shook hands all around.

"Just top her off, Scotty. We're going up to the house and make sure it's still standing. I'm going leave Jeff and Tim here for a few days to do some maintenance," Pops said.

"Leslie is here again this summer," Scotty asked. He was shaking his head and laughing.

"You're goddamn right, she is. One day, I'm going to have to tell her mama that the tit's ran dry," Pops replied.

Jeff and I looked at one another, smiling. Just before we'd landed, Pops was bitching about Leslie and the "shenanigan" she called college.

"You boys take the jeep and head to the house. I'm going to the hardware store to get a few things," Pops said.

"Okay, Pops," I said. Jeff and I hopped in the jeep and started towards the house. Naturally, the conversation of choice was around my morning.

"How was it," he asked.

"It was really great," I replied as I drove. "I mean I've never felt anything like it."

"I bet."

"She blew me, but when we started having sex it was really amazing."

"Man, I bet so. I mean you blowing me was awesome, I can't wait to find out what pussy is like!"

"You don't mind do you? She's your sister," I said.

"No, I don't mind. I mean she's fucking hot, but she's still my sister," he replied.

"Yeah, she is."

"Now, Katie on the other hand," he laughed.

"Yeah, I know. She's really hot, too."

"Or what about Leslie. Schwing," he said as his hips raised out of the bucket seat. It was from a popular comedy show and we'd laughed about it for years.

"Yeah, Leslie," I agreed with a smile.

We pulled up in front of the house and to our surprise, only Leslie's Porsche was in the driveway. We'd joked there would probably be a half-dozen cars in the driveway from the previous night. I grabbed the spare key from under the large flower pot and unlocked the door.

"Leslie," I called. We started looking around and soon returned to the living area and shrugged at one another. I started walking to the glass back door when I saw her. I stopped in my tracks. She was laying on the back deck in a lounge chair. She was wearing sunglasses and nothing else. Jeff walked up beside me and stopped when he saw her. We looked at one another and both mouthed "wow".

We stood there watching her and she started moving. She got up from the chair and faced away from us. She stretched and put on her flip flops as we stood there in total silence watching her. Her dark hair was much shorter than I remembered from the previous summer. She walked to the outdoor shower and I stared longingly as she stepped in it. We both seem to hold our breath as she slowly washed the suntan oil from her body. Jeannie's body was magnificent, but Leslie... I could only imagine what she looked like in that little orange bikini Jeannie had been in the night before.

She took her time and finally shut off the water. As she dried, Jeff and I looked at one another again.

"Man, we should sneak out and come back in, or she'll know we were watching her," Jeff suggested.

"Yeah, you're probably right," I agreed. We turned as she disappeared from sight. We were just opening the front door when we heard her come out from the kitchen.

"Where are you little pervs going," she asked. She had her towel over one shoulder and was still as naked as she could be.

Jeff and I both tried to talk, but neither of us could find the words.

"Uh huh, I see. I heard you two walk in and start perving me. Where's Daddy," she asked.

"He's at the hardware store," Jeff replied.

"Am I in trouble," Leslie asked coyly.

"Maybe, a little bit," I smiled.

"Great," she said as she rolled her eyes. "Lecture time, again. What good is having money, if you can't enjoy it a little."

As she talked, I couldn't take my eyes off her. Her tan breasts were full and ripe. It was obvious from her even tan, she routinely took full advantage of the private back deck and pool. My eyes trailed down to her womanhood. It was delightfully bare.

"You've been in college a long time," Jeff snickered.

"What do you know about it? You haven't even started. You don't know how much fun you'll have in Austin!!"

"Yeah, so I hear. Are you going to get dressed before Pops gets here," Jeff asked.

"Have you two little pervs got an eyeful, yet," she asked.

"Well...," I said admiring her luscious body.

"Timmy, you were always the sweet one. Not like this wise ass. Jill would freak the fuck out if she knew you were looking at me like that," Leslie said.

"What would she think about you standing there showing me," I asked.

"You have a point. I better get dressed so I can get a lecture. I'm glad I picked up the beer cans already," she said as she walked to her bedroom. Jeff and I bolted out the front door as soon as she was out of sight.

"Holy shit. Can you believe that just happened," he asked.

"Hell no, I can't believe she just stood there naked in front of us," I smiled.

"I think I just got a year's worth of jerk-off fantasies," he laughed.

"Yeah, me too," I replied.

We stood around for a bit and finally saw Pops rolling up the mountain road in his Blazer. He was pretty peculiar about things. He drove that old van around every day in Dallas, but he had the Blazer and the Jeep sitting at Aspen that may have had 10,000 miles on them. Things like that always made my Dad laugh.

"There's some paint in the back. There's brushes and rollers in the shed. I want you boys to paint the back deck," Pops instructed.

"Yes sir," Jeff and I replied.

"I'm gonna go talk to your aunt," he said shaking his head.

We'd just come out from the shed when Pops and Leslie walked out of the house onto the deck. I looked at Jeff and we smiled at one another. Leslie had her arm around Pops and they were laughing. He could tell us he was going to read her the riot act, but Leslie had him wrapped around her little finger. She walked back inside and Pops walked over to where we were at.

"You boys have everything you need," he asked.

"Yes sir. I think so," I replied.

"Okay. Y'all just take it easy up here. No need in burning out any bearings. Get this done and if I think of anything else, I'll let you know," he said.

"Yes sir. We will," Jeff said.

"Oh, I almost forgot," he said as he reached into his wallet. He handed both of us some bills. "You might want a little walking around money."

"Thanks, Pops, but I've got money," I said trying to give it back to him.

"Forget about it. Call it your wages for painting," he laughed. He turned to walk back in the house. "I'll holler at y'all tomorrow."