Debbie Floats My Boat

DEBBIE FLOATS MY BOAT

By Phynneman

I would like to thank VCWITER17B for his help in reviewing and editing this story.

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This story is mostly true. The location, the boats, and the time frame this takes place are accurate and true. How quickly things happened has been condensed for the sake of storytelling.

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Her name was Debbie. She's a cute blond with short hair. She is also thin. I don't mean model skinny, who look like they have starved themselves, but she was not curvy. She doesn't have a big chest, nor is she flat-chested, but what she does have is a lovely shape for her. She says she is a "B" cup in bra size. I call it a "Perfect handful." Her nipples stand out, just the right size to grasp between fingers or capture with your lips. She had let me play with them on our first dates. I got to play with them anytime I wanted because later, she married me.

We went to high school in Key West, Florida. We lived on different islands up Highway US1, several miles from Key West. I first noticed Debbie in our junior year when we had a class together. Other than her blond hair, I gave her little thought.

It was the last year of the 1960's. Tie-dyed shirts, bell bottoms, free love, hippies, "Hair," and "Aquarius -Let the Sunshine in" were the top songs on the radio. It was also the last few days of high school for us.

In our senior year, we had several classes together. We were both 18, and I began to see her in a different light.

In History class, I would sit behind her, and in English class, she would sit behind me.

Our minds weren't really on class or the lessons, and our teachers knew it and didn't press it too much; as long as we weren't disrupting class, they mostly ignored our daydreaming or note passing.

It was Friday, a half day for seniors; when our three classes were over, seniors got released from school at 12:00.

Our History class was in third period, and English was today's first class. Debbie was sitting behind me in English. The week prior, I had been water skiing, snorkeling, and swimming most of the weekend and had gotten sunburned. Now, dead skin on my back, neck, and the back of my legs had started to peel.

I felt some tugging on my neck, and I turned around. Debbie had started peeling my blistered and dead skin from my neck and then rubbing my neck. "Your skin is nice," she whispered in my ear. It felt good.

I turned back around and let her continue. After class, we both had to rush to our lockers to put away books and grab things we needed for the next class.

The third class was History, the last class for the day. Sitting behind Debbie, I leaned forward and asked if she would like to go out with me. She said, "Sure I would. Do you have a car?" I told her I had a pickup truck. "Meet me after school in the south parking lot. We can go have lunch somewhere if you want."

She told me she would have to call her mom first and tell her she wouldn't be coming home on the bus. There were no cell phones back then. She had to phone from the school's pay phone near the front office.

I had to wave to get her attention when she got to the parking lot. As she walked up, she said, "I must be home before dark. Is that a problem?"

"Shouldn't be. Let's grab some burgers and drinks at the A&W and then go to the beach." I suggested, and she agreed.

The A&W was on the other side of Key West from the high school. The beach was along the A1A side of the island, which was again on the other side of the island from the A&W.

It took little time since if you drive from one end of Key West to the other and catch every stop light red, it will take 15 minutes, less if the lights are green. At the A&W, we got our food and then went to the beach.

I parked on what was known to us as "The bridle path." A dirt road that ran parallel to the beach but separated by some brush. We took our food and walked until we found a secluded spot up from the beach surrounded on three sides by mangroves and brush.

We sat in the grass and sand, eating our french fries and burgers and talking about our classes and teachers. She finished eating first, then asked something no one had ever asked me. "Can you remove your shirt so I can peel your back?"

"Ya, I guess so." I took off my shirt and turned so my back was to her. She started to pick at my skin. She liked to see how big a piece she could remove at one time. It did tickle some, but it actually felt nice.

After she had been at it a while and we were making small talk, she mentioned how, with her fair skin, she would burn very easily and then peel just like me.

"I got sunburned last week when we were on my father's boat. I've also started to peel. I don't understand why, but I like pulling big pieces of skin off. It makes me..." She trailed off from her talking.

She told me, "Turn around and let me do your front." So I turned around. I had little burned skin to peel off, mostly on my shoulders, and she finished quickly. I didn't think first, or I wouldn't have said it, but it just came out. "If you're burned and peeling, can I do your back and...front?"

She giggled and then got quiet. "Yes." She unbuttoned her blouse and pulled it open. She then took it off, folded it, and placed it beside her. I was looking at her pale blue bra and white skin with light brown freckles.

"What's the matter? It covers more than my bikini top. Start with my back." She then turned around. I was looking at her back, and indeed, her skin had just started to blister. I began to rub off small pieces of dead skin from her shoulders.

There wasn't much that would come off, but I liked touching her back, so I continued as if removing dead skin.

She shivered under my touch as I moved further down her back. "Cold?" "No, it just feels good, very good, don't stop." I continued until I got to where her bra was across her back. Even though there wasn't any skin to remove, I moved my hands below it.

"Wait." She said. She then reached behind her and unhooked her bra. She shrugged her shoulders, and making a show of it, she held it to her side and dropped it onto her blouse. She let her arms go to her sides. Even though she had her back to me, I was surprised she didn't use her hands to cover her chest.

"Go ahead and get it all off."

I couldn't help myself. "The dead skin or your clothes?" She took in a deep breath and softly said. "Which do you want off?" I hesitated. "Both would be nice."

She didn't answer me. I continued like I was pulling off little bits of the dead skin from her back. I enjoyed touching her. "That's all," I told her.

She turned around, facing me, and looked at me. She made no move to cover her naked breasts. It took everything I had to stay looking at her face and not stare at her chest.

She looked at me as if studying my face. "Go ahead and look, I don't mind." I did look. Her breasts were not big but firm. They were milky white with light brown areolas and slightly darker nipples.

She had freckles where the sun had not tanned her skin. She was right. Her bra did cover more than her bikini top. She reached up with her hands and cupped each breast. "I know they aren't big. I'm a B cup, and boys like big boobs. I don't have them. I'm more like my mother. I hope they'll get bigger someday, but for now...oh well. They are what they are. But my nipples will stand out really far if you play with them." She took each nipple between her fingers and rolled them around. As she dropped her hands and pushed her chest towards me, she asked, "Want to play with them? Go ahead, I don't mind."

"Are you sure? I don't want to do anything if it makes you uncomfortable." I said, hoping she wasn't just teasing me.

"It's OK. I said you could play with my nipples."

I reached for her chest and felt her soft breasts for the first time. Her's were the first breasts I had ever touched. My fingers crossed her nipples, and just as she said, her nipples stiffened and turned a darker red.

"See, I told you they would stand out. Go on and touch them."

So I did. As I ran my thumbs over them, they did indeed get bigger and harder. Debbie pushed her chest more into my hands. She put her hands over mine. "Squeeze them, my nipples; squeeze them between your fingers."

Again, I did as she asked. She shivered as I played with her nipples between my fingers. "Harder, please do it harder." She begged. So I did.

She closed her eyes and pushed her chest harder into my hands. She then put her fingers over mine. She clamped her fingers down hard over mine. I know it must have hurt, but she started pulling on her nipples and squeezing even more.

She moaned through half-open lips and closed her eyes, then shuddered all over. She pulled my hands away from her nipples.

She looked into my eyes, leaned into my chest, and kissed me. She put so much intensity into it that I was surprised. I did like the feel of her nipples on my chest, so I put my arms around her and pulled her tight into me. She responded by hugging my neck and pushing her tongue between my lips. I had never French kissed before, so I didn't know how to react. After a bit, she pulled away and looked around.

"I've never shown my titties to a boy, much less let one touch me. You're the first one ever. I liked it. Did you?" I told her I did, I very much did. Then I asked her why now and why me? She said she wasn't really sure, but I had always been nice to her; she just wanted to know what it was like to show her small boobs to someone who wouldn't make fun of them as some of the girls did in gym class.

"Why did you let me touch them?"

"I guess after you had looked at them, I owed it to you to let you at least have a feel, and I wondered how different it was to have someone else playing with them besides me." She looked through the mangroves and saw more people on the beach than when we arrived. "We better go." I nodded my agreement and looked down once more at her breast.

"You like looking at them, don't you? You can have one more feel if you like."

I couldn't resist, so I ran my hands over both breasts and her nipples, and again, they started getting hard. Looking at my face, and with a big sigh, she told me, "If you keep doing that, we won't leave here until after my curfew."

We put our clothes back on, picked up our trash, and returned to my truck. I asked on the way back to her house. "Would you like to go fishing on my boat tomorrow? We could pack drinks and lunch and make a day of it."

She smiled at me. "Is that what you want to do, go fishing? Or is this just some way that you think you can get me out of my clothes and look at the boobs of a flat-chested blond girl?" We both laughed.

"I like you and want to spend more time with you, and if you want to show me more of your boobs, I'm not going to stop you."

Debbie laughed and said, "If we go fishing, we better bring back some fish, or we'll be in trouble."

We got to her house, and she leaned over and kissed me several times. I was beginning to get the hang of this tongue gymnastics and liked it.

She got out of my truck and, before closing the door, leaned in and said. "Tomorrow sounds good if my parents don't object. Who knows, you might get lucky besides seeing my boobs, I might let you see everything. Now, before you leave your truck, you better take care of that problem in your pants." She closed the door, turned, and walked to her house. I looked down, and my pants had a big tent sticking up.

I called her that night, and she said she could go. I told her I would pick her up at 9 AM.

I had loaded the family cabin cruiser with all the fishing gear last night and put bait, drinks, and some snacks in the ice chest that morning, so we were ready to go as soon as we got back to my house."

My family's home was on a different island; we also had a house on a canal. To get to where we could fish, I had to navigate through several canals, channels across swallow water, and other channels that wound their way through mangroves. If you want to go to the Atlantic Ocean, you go through the southern channels, or if you go to the northern channels, you will get to the Gulf.

We had three boats in the family. The largest boat was a 24-foot inboard/outboard cabin cruiser with V berths and a toilet, which we used to go fishing in the Atlantic Ocean and out of sight of land. Also, there was a 16-foot inboard jet boat we mainly used for water skiing, and last was my 14-foot runabout with an outboard motor.

I had picked the cabin cruiser today, telling my father it was because it had a toilet onboard, and this would give Debbie some privacy if she needed to use it.

I picked Debbie up promptly at 9. She wore jeans, a loose pull-over wrap, and a T-shirt under the wrap. She also had a big bag and a fishing rod and reel. Then I had to meet her parents.

They wanted to know exactly where we were going. Her dad rolled out a chart of the area, and I had to show him where I planned to go and what I would fish for. Her mother wanted to know how long we would fish. They also asked what type of boat I had. How long had I been around boats. When would we be back? They asked for my home phone number to call my parents if necessary.

Before we left, her mother made her promise to call them as soon as we got back to my house from fishing. Debbie said goodbye and picked up her bag. I put her rod and other things in the back of my truck, and we left.

When we arrived at my house, I had to introduce her to my parents, and they made a big deal about going through the same routine as her parents. Where I was going, when I would be back, etc.... She gave them her parent's phone numbers and where she lived.

Debbie and I got on board the cabin cruiser. I went through the startup routine, untied the boat, and pushed off. I pulled out from our seawall, headed down the canal, and out to the channel that went to the Gulf side.

There was a small step you had to use to sit in the cockpit chairs. They had to be tall enough to see over the cabin roof. The step also provided a place to put your feet while riding.

Navigating the canals and mangrove passages took about an hour to get to where I was heading to fish. Bottom fishing would be better than trolling. Then, I could shut the engine down and put the anchor out.

With it being quiet, we could talk, and I wanted to continue with our exploring from the other day. I was too naive at the time to realize she also wanted to continue with our exploring.

While we were heading out and once away from houses and other boats, Debbie hopped down from her chair. She picked up her bag from the deck. "I'm going to go below and change."

She then went down the three steps into the cabin but didn't close the folding door. With the door open, I could see into the cabin. As she removed her wrap and began to take off her T-shirt, she turned around, facing me; she slowly pulled her shirt over her head. She wasn't wearing anything underneath, and her nice firm white tits and hard nipples were on display. Her aureoles were a light brown, with her nipples in the center. The bouncing from the moving boat also made her breasts bounce. The wind played across her chest and made her nipples erect, and so was I.

She smiled up to me. "Like what you see?" She had to shout to be heard over the engine. I nodded yes.

She looked in her bag and pulled out her red bikini top and bottom; glancing up at me, she smiled as she put her top on, covering up her erect nipples.

She then turned around and pulled her jeans down, exposing her very cute butt clad in pink panties. She wiggled her butt while she took off both her jeans and her panties. She had an adorable white backside. I knew the show was for me cause I didn't think girls would do that if they were by themselves. Taking her bikini bottom in hand, she stepped into them, and, once again, wiggling her butt, she pulled them up around her waist.

She came up out of the cabin and joined me. Turning around in a circle, she asked. "Like it?" I wondered if she meant the bikini or the show she had just put on.

All I said was, "Yeah!"

I was sitting in the captain's chair, which made her head reach the middle of my chest. She smiled up at me, and then we both laughed. She reached up to my face, pulled me down, and kissed me. I kissed her back. We did it some more until one time, I looked up and found I was out of the channel and headed for the shallow flats. I quickly turned the boat and got us back inside deeper waters. Debbie laughed at that.

She went to the ice chest, got us drinks, and handed me one. She started to say something but stopped.

"What?" I wanted to know. She tilted her head and shook it no. "Not now, maybe later when we stop." She answered. But I noticed her eyes were on my crotch, which had a tent showing how hard I was from watching her change her clothes. She got back up into her chair. We drank our sodas and didn't try to talk until we got to our destination.

I chose a spot to anchor the boat behind one of the numerous islands that put us out of sight of other boats that might be headed out into the Gulf.

I shut down the engine and secured the boat with the anchor. Debbie helped me get the fishing tackle out and baited the hooks. She was no stranger to fishing and did not make a face or act "girly" about handling bait. She reminded me that she had been out fishing with her family and brother since she was a little girl.

Once we made a few casts out and set the lines, Debbie turned to me and, catching me completely by surprise, asked me. "Do you masturbate?"

"What? What do you mean?"

She leaned over the side of the boat and washed her hands off from handling the bait. I did the same while trying to get a good look at her bottom in her tight-fitting bikini that showed off her cute butt.

As she stood up, she asked. "Well, don't all boys masturbate? I think they do. My brother does. I can hear him in his bedroom at night when our parents are gone. I can hear slap, slap, slap, and then he moans kind of loud. I can smell it on the towels when I do laundry. So, do you do it?"

She had such an earnest look that I could tell she wasn't trying to be cute or put me on the spot, but she truly wanted to know if boys did that.

"Yeah, sometimes I do. But not very often." I told her. "Do you?" I was just as curious as she was. She answered quickly. "Yes, like you, not very often, but yes, I do."

I wanted to ask how girls do it but didn't because of the look on her face. She looked puzzled.

I was surprised how unexpectedly she started talking about personal sex habits. "You look like you want to ask something else. What is it?"

"Can I see your penis? I've never seen one up close." At first, I was both taken aback and surprised, but why should I not comply? After all, she had seemed very comfortable with getting bare-chested with me and letting me feel her breasts and nipples.

I stood up, unbuckled my belt, and pulled my zipper down. Just as I was getting ready to let my cut-off jeans down, she stopped me by putting her hand over mine. She looked up at me and asked. "Can I do that?" I just nodded.

She slowly took hold of each side of my cut-off jeans and tugged them down. She pulled my jeans down and followed them down until she was bent over. My dick sprang forth once free of my jeans. Debbie just looked at it, bobbing in front of her face. I stood there with my cut-offs pooled around my feet. I stepped out of them and pushed them under the captain's chair. Then I took off my T-shirt. I stood there as she looked at me. Her eyes never left my dick.

Because I was nervous, I wasn't hard but not entirely soft either. Looking up at me, she asked. "Can I touch it?"

"Sure, you can touch it." Boy, did I want her to touch it! I wanted her to do more than touch it, but I had no idea how to ask her. Besides, I didn't think she would want to do the things I had read about in porno books.