Kaye's Trip to the Islands

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

"I think that means we will take it," I smiled at the clerk. "With one condition, however, it doesn't leave here unless it is on the neck of a beautiful woman."

"I agree completely," the clerk smiled at both of us.

Kaye just stood there with the necklace in her hand looking down at it, with tears now streaming down her face.

"All right," I turned to Kaye. "Let me pay for this and we'll get it all hooked on."

I paid the clerk and she showed me how to clasp it so it wouldn't accidentally come apart. I spun Kaye around and had a look at her new apparel. "Yup, I liked it before but it definitely looks better this way."

Kaye stepped over and gave me a hug. She was trembling but when I put my arms around her she stopped and burrowed into my arms. The clerk smiled at us and handed me the empty box. I put it in the bag with the underwear and then shuffled Kaye out the door.

"So, am I forgiven for buying you the non-sexy sleeping attire?" I asked.

"Yes," Kaye admitted, "but I'm still going to model them for you. Oh, hey wait. We are going back to that clothing store."

Kaye grabbed my hand and dragged me back to the clothing store. The clerk instantly recognized us. "I would like to buy this man a pair of red flannel underwear," she stated.

The clerk asked me my size and then produced a package of underwear. Kaye insisted on paying for it and then smiled at me. "We are going to have a pajama party."

The afternoon really was miserable. It was really hot and humid, the streets were crowded, the flies were everywhere and the smell was sickening. Kaye said this was the best day of her life but she was ready to go back to the boat and get away from the crowds.

At about 6:00PM a front blew in and the temperature dropped from 90F to 50F in about 45 minutes. Perfect night for a pajama party she winked at me. "Well, if I have to go to a pajama party then you have to cook supper," I said.

"So I have to cook supper and throw a pajama party?" she looked at me.

"Sure if you want to look at it the wrong way." I paused for a moment. "Okay I'll help with supper. We can have my SPAM surprise," I said excitedly opening the cupboard door and reaching in.

"Stop!", Kaye shouted. "Drop it and step away from the SPAM. I have a spoon and I'm not afraid to use it," she said pointing it at me. "You were right, I should cook supper. Besides, it will increase the odds that we are both alive to attend the pajama party." Then she smiled, "don't ever use the words SPAM and surprise in the same sentence."

I stepped away from the kitchen and decided it would be better if I just assisted. Kaye fixed a garden salad and two steaming bowls of chili - a perfect cold evening supper. I took care of the dishes and Kaye handed me the underwear we had purchased earlier.

"Here, put these on. Time for us to see each other in our underwear." She seemed way to excited for an evening of sitting around and talking.

When I returned, the TV was playing a fireplace app and it was crackling appropriately. Kaye was nowhere to be seen. Then I heard her shower go on, then off, then a hair drier and it went off. Several minutes later Kaye emerged.

"Oh my god," my jaw dropped. Her blond hair was draped over her shoulders and was perfectly brushed. It contrasted perfectly with the red flannel. The sleeves were a little long but that just added to the soft feminine glow of the woman standing there. She was wearing the gold sailboat necklace which hung perfectly on her and against the red flannel. Her blue eyes radiated and she carried a white bed pillow.

"Veux-tu coucher avec moi?" She whispered the french we had learned in class together.

I was paralyzed by the beauty of the goddess that stood before me.

She walked up to me and put her hand on my chest and looked into my eyes. "oui?"

I was about to speak when I got a whiff of apple. That was the trigger for me. I lost all self control and pulled Kaye and I onto the couch and then rolled Kaye on top of me. I had completely underestimated the sensuality of a totally naked woman wearing flannel. I touched and rubbed as I hugged her. I kissed her as I explored with my hands. Everywhere was soft and warm and perfect.

We made out like school kids. I got lost in Kaye. There was no boat, no lake, nothing except Kaye and how she made me feel and how much I wanted her.

I slowly came back to my senses and eased my grip on Kaye. I looked up at Kaye. "If we ever sleep together, promise me you will wear boys red flannel pajamas."

"Oh, you like them do you?" She looked down my pajama clad body and noticed the tent in my pants. "Oh, I see you do." She licked her lips and moved her hand toward it. I thought she was going to touch it but at the last minute placed her hand on my stomach and rolled completely on top of me making sure it was between her legs.

"Euchre?" I announced.

"What? What are you talking about?" she asked.

"Euchre, it's the card game you play at parties," I said reaching back and grabbing a deck of cards.

"What? We are doing cards?" Kaye seemed confused but decided to go along. I needed something to distract me from the wonderful softness of her body. Cards seemed like a reasonable choice.

We really did have fun. Kaye can be amazingly competitive and as such can really celebrate when she wins and can be devastated when she loses. However, she realized it was all in good fun and made funny faces at me when I was about to win.

At 2:00AM she came over and gave me a hug. The next thing I remember, it was 8:30AM and Kaye was on top of me sleeping like an angel. I wrapped my hands around her and I melted. I was filled with emotions of love, happiness, content. I felt amazingly protective toward this woman. I wanted to make sure I was giving her the same emotions of love and happiness that she was giving me.

I needed to explore this feminine beauty. I pulled her top up slightly at her waist and slid my hands underneath and along her back, skin on skin. I slid my hands up and down her back. There was no friction only the silky smoothness of her perfect skin. I went up and down and back and forth until I knew every inch. Kaye let out a soft moan and a few minutes later she let out a louder one and she moved slightly and I stopped.

"Oh please don't stop. It feels wonderful," Kaye mumbled.

I continued gliding my hand across her back. I knew I was getting more pleasure than I was giving but I don't think Kaye knew. She kept moaning and purring with every stroke of my hand. This continued for a few more minutes when Kaye suddenly arched up, reached down, pulled her top off, threw it on the floor and laid back down and wrapped her arms around me.

I continued as if nothing happened. However, now I had access to her shoulders, arms and neck.

My hands continued as my area of exploration got larger and larger. Kaye moaned as I slid along her shoulders and neck. I returned to her back and slid under her pants.

"Yes, oh god yes. Anywhere you want. I love it." she whispered in my ear.

As I slid my hands around her ass, she began to thrust her hips into mine and moan "yes" each time.

I realized I might have gone to far and we were heading in a place we weren't ready to go.

"Hey, you know what the best part of sleeping with you is? It's waking up with you," and I kissed her on the cheek.

"Oh dam-it, I wish I had said that. Now I have to think of something even sweeter to say," she said.

She laid her head back on my chest. "Oh, I need coffee. I also need a shower. I can't believe how wet you made me."

"Oh dam-it, I wish I had said that," I said.

"Nice try but NO!" She said, getting up and grabbing her top off the floor. "While I'm in the shower, make us some breakfast."

"SPAM and eggs coming up," I shouted.

She stopped and turned back toward me. There they were, the constant objects of my high school lust and masturbation. I could not have imagined more perfect tits. "If you touch that can of SPAM, instead of sleeping with me, you'll be sleeping with da fishes." She tried her best godfather accent.

I decided eggs and bacon was the way to go this morning, which I prepared while Kaye was taking a shower. She did something a little curious and left the shower door open. I wasn't sure if she felt safe with me or she thought we had shared an intimacy that allowed a certain latitude in one's personal space. Confessing I had burned breakfast because I was perving the first mate was not something I wanted on my rap sheet - so I focused on breakfast and didn't have a very good view into the shower.

We decided at breakfast that we should leave right away and head to Beaver Island. She also asked if there was some place she could store her necklace when she wasn't wearing it. I pointed her to the ships safe and told her the combination.

She returned a few minutes later and sat quietly. "I'm ready to go when ever you are," she smiled at me.

"Okay, you're driving," I smiled back at her. "I'll take my shower while we are underway."

We went up to the cockpit. "The first thing you are going to want to do is start the engine so that it is up to temperature when you need it. Then tell today's first mate to get his ass up there and uncleat the bow and spring lines. Coil them up and put them away." I instructed today's captain.

I did as I was told and then singled up the stern line and stepped back on the boat.

"Now place the transmission in reverse and slowly back the boat out of the slip. If the boat starts going sideways I'll jump in and help but don't panic."

She did exactly as I had instructed and the boat backed perfectly out of the slip. I coiled the stern line and went back and stood by today's captain.

"Now put the transmission in neutral and lower the throttle. Excellent. It is okay to let the boat drift backward, you have room. Okay, now move the transmission to forward, turn the wheel all the way to port, that's called hard to port, and then give it some throttle." I instructed her on every maneuver which she carried out perfectly.

The boat slowly moved forward and turned to port. When it was aligned perfectly between the rows of boats, Kaye straightened the wheel and the boat moved out of the marina and into the harbor.

We had a few minutes and there were no boats in the harbor so we stopped and I showed Kaye the interesting phenomenon called prop-walk and the use of the bow thruster. Kaye loved the bow thruster but was fascinated with prop-walk. She kept backing up the boat with different speeds trying to understand exactly what it would do and how she could use it to her advantage.

The trip over to Beaver Island took exactly 24 hours. Going under the Mackinaw bridge is always a treat and the rest of the trip was fairly routine. I took the midnight shift like we did on the trip up to Mackinaw Island and Kaye took the early morning shift. At 8:00 AM she spotted land and came and woke me up.

I contacted the marina on the VHF and got our slip assignment. Then I went to the locker and grabbed the fenders and tied them onto the lifelines. Kaye started the engine and I helped her furl in the main and jib sails.

When we got closer to the slip I noticed a young man waiting for us.

"Okay captain, the boat is yours," Kaye said.

"What? No, your shift doesn't end until 11:00. Don't abandon your post," I smiled at her.

"But what if I...?" She started.

"Just take it nice and slow. I'm going to hand the marina worker the bow line and then come back to you and help if I'm needed," I reassured her.

We were coming in at a weird angle and I thought for a second I was going to have to run back to the helm and help out. However, at the last second Kaye hit the bow thruster and the boat turned suddenly and we were precisely lined up with the slip. The boat slowed and started into the slip.

I quickly handed the young man the bow line and whispered, "we have a rookie captain so don't be afraid to use the cleat if you need to."

I quickly ran back to Kaye to see if she needed help. She had just shifted into neutral, letting the momentum of the boat carry it into the slip. When it was a foot from where she wanted it, she kicked it into reverse and gave it a touch of throttle. The boat came to an instant stop.

The marina worker quickly cleated the spring and stern lines and then turned to Kaye. "Nice job pulling into the slip captain, these winds and currents can be tricky. When you get a minute please stop by the office and check in."

Kaye was all smiles as she turned off the engine and stepped off the boat. She gave me a hug and whispered, "thanks for trusting me with your boat. You're a sweetheart."

I hugged her back. "Trust well earned."

We just wandered around the little town and checked out the stores and shops. It was a quiet little town that had the required t-shirt shops and gift stores for the occasional visitor that either came by ferry, commuter plane or personal boat.

I bought Kaye a small stuffed beaver. It was fun watching Kaye turn red every time I made some comment about how I liked her beaver. By the end of the day it was wearing thin so I ended it by grabbing her beaver, giving her beaver a kiss and hoped I could play with it again tonight. She flipped me the finger and I knew we were done with the beaver jokes.

We had a wonderful supper on the boat and afterward the long watch last night and the lack of sleep forced me to head to bed early. I stripped down to my underwear, pulled back the covers and laid down. About 5 minutes later there was a soft knock on the door despite the fact I had left it open.

Kaye was dressed in a pair of her red flannels, carrying her beaver and a pillow. "I heard you might want to play with my beaver and I wasn't sure which one." She turned back the covers on the other side of the bed and crawled in.

She wrapped her arms around me and realized I was only wearing my boxers. "I think I came dressed a little to formal."

"Well, any time you want to get a little more comfortable it is fine with me." I said.

"I might just take you up on it," she said. Then she realized the stuffed beaver was sitting on my stomach and she lifted the covers so she could see it. "You stay away from the wood, that is my job." She spoke to the stuffed animal. She then lowered the covers and laid her head on my chest.

I'm ashamed to say but the next thing I remember I was laying on my side and it was 7:30 AM according to the clock on my dresser. I felt this wonderful sensation on my backside. I felt down at my boxers and my cock was hanging out. Then I felt behind me and all I felt was warm soft skin. Kaye had removed all her clothes and was spooning me.

Wake her or not, I had to do front to front contact. I rolled over and pulled Kaye toward me. I love the feel of tits on my chest and I got instantly hard. Kaye moaned slightly and started to wrap her arms around me but stopped midway. She reached down to my boxers and hooked her fingers into the waistband. "Lift your hip so I can finally get these fucking things off you."

I complied and the boxers went to my ankles. I thought for a second and grabbed her wrist. I brought her fingers to my nose. "Uh Oh. We've been a bad girl last night haven't we Kaye?" as I distinctly smelled the sweet scent of her sex on her fingers.

"Well... you were there... and it was there... and I couldn't sleep. I got horny. I love you, okay? I've got all these emotions swirling around in my head. It was only a foot away and then it was 6 inches away and then it was in my hand. I came really hard but I love you so much and all I want to do is make you happy. I crave it so bad, I hurt."

"Hey, it's okay," I smiled at her. "Remember the other night when we slept together. I woke up and found you on top of me. I realized then how much you mean to me. I had tears streaming out of my eyes as I realized how much I want to protect you and take away every bit of pain in your life. I can't imagine my life now without you. I just want to make you happy, I love you too."

We kissed deeply. "Does this mean you are going to make love to me?" Kaye asked when we separated.

"Who's your best friend?" I asked.

"You are," her eyes misting over.

"Well friend, it is time to take our friendship to a new level."

Kaye rolled over on her back, spread her legs and pointed to where she wanted my cock. "Be my friend. I love you," she whispered.

I positioned myself above her.

"I want it inside me so bad," Kay looked at my cock lustfully. She grabbed a hold of my cock and pointed it at her pussy. Then she lifted her legs and wrapped them around my back and pushed me inside her.

I moaned in delight and Kaye screamed, "oh fuck, yes!" as I bottomed out in her pussy. I began pushing in and out of Kaye's amazing pussy. She lasted about two minutes and she screamed in ecstasy as her first orgasm ripped through her.

I was hoping to last a lot longer but the second Kaye let out a scream I got an image from my past - I was picking up text books and looking up at a two beautiful legs and a white pantie clad pussy. That did it for me and I pushed into her as hard and deep as I could and I shot out 35 years of lust, passion, desire, regret, and a dozen other emotions deep into the pussy of the goddess I had desired since high school.

Part 2

I was amazed at how good I felt. I love sex but this was nothing like I have ever experienced. It was more spiritual than physical. All I wanted to do was hug and caress her and enjoy the wonderful afterglow of the bond we had just created.

We just laid there, wrapped in each others arms and legs. There were no words. We just looked into each others eyes and occasionally kissed. Her face burned into my memory, seeing the beautiful Kaye content, happy and smiling was the most amazing sight in the world. I could have looked at her forever. Time stood still.

"God you are beautiful," I whispered.

She hugged me tighter and began running her hand along my back. I kissed her lightly and Kaye kissed me back harder, pushing her tongue into my mouth.

I returned the favor and began rubbing her back. I realized then that my cock was hard again so I flipped Kaye onto her back, spread her legs and rolled between them. In a sudden thrust I pushed my cock into her well lubricated pussy and bottom out, pushing into her as far as I could.

I gave her a couple of slow deep thrusts and Kaye started thrusting up into me urging me to go faster.

"Shhh, no. I'm in control now," I warned her with a quiet whisper.

I continued with my slow deep thrusts. Kaye had a blank stare on her face and was panting heavily. When it looked like she was close to a climax, I slowed even more. When it looked like her urge to cum had passed I sped up again. I continued to play Kaye - bringing her up and down. I was getting a feel for what she needed and what she liked.

I was making her crazy. She started wiggling and flopping her head back and forth. She was panting, moaning and randomly saying words like fuck me, harder, I'm close.

I was now going so slow that even the slightest movement was making her crazy. I tried desperately to keep her on the edge. I was doing really well, speeding up, slowing down, going deep or shallow. The reality was I was having trouble controlling myself also. I was watching this gorgeous angel in ecstasy from my cock. I wanted to make her happy and give her what she needed but I realized the longer we waited the bigger the payoff and it would be something she would always remember.

She was becoming delirious and I wanted to cum with her. I too was approaching the point of no return. I gave her 3 fast long deep strokes and she let out a scream. Her pussy gave a sudden spasm and that was it for me. I pushed into her as Kaye howled, twitched and screamed. I dumped what seemed like a gallon of ball juice into her sweet pussy.