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Introduction:

What can I say, I love sailing.

I am still not sure how I get myself in to certain situations.
I know that I have a very deviant side to me that lacks a moral compass.
Maybe someday I will have to see someone about that.

Being that it's summer and boating season is upon us, I am a much happier camper.
Even better when days at work become slow and I can sneak away from work to do a little lunchtime sailing.

It happened to be one of those days that contributed to this situation. I am still not sure how I get myself in to certain situations.
I know that I have a very deviant side to me that lacks a moral compass.
Maybe someday I will have to see someone about that.

Being that it's summer and boating season is upon us, I am a much happier camper.
Even better when days at work become slow and I can sneak away from work to do a little lunchtime sailing.

It happened to be one of those days that contributed to this situation.
I woke up at my usual 5:30am feeling pretty good. After getting changed and having a sip of coffee I headed out for my usual morning run.
As I was running along I noticed how beautiful the morning was. The sky was clear and the sun was up doing it bit to warm the air.

When I finished my run and returned home, it was still quiet. My wife and kids were still sleeping off their late night of firefly catching.
I decided to head down to the basement to cool off from my run and check a couple of emails.
There were only a couple pieces of spam in my inbox, so I checked the weather to confirm what a great day it was going to be.
We were expecting 88 degrees with 18 knot winds. “This would be a great day to go sailing” I thought to myself.
Then I did a quick check of work and noted that things were pretty light. I made up my mind on what I was going to do today.
I decided, since I had some time to kill than I would go visit one of the old chat rooms that I used to frequent when I was single.
The room only had one person in it, which I did not recognize so I left.
I still wasn’t ready to start getting ready for work so I decided to drop in to one of the local public chat rooms.

I entered with my usual “Morning everyone!”

I got a couple of hellos back followed by the usual chatter in the rooms of people who are familiar with each other.

“Beautiful morning outside” I continued.

There was a “Yes it is” followed by a “Too bad I have to work” comment.

“True” I continued, “but I think I’m going to play hooky during lunch today and go sailing.”

That got a couple of responses that read “Lucky dog!” and “Sail some for me” and “I want to go!”

I was feeling pretty good about my decision as I watched the conversation scroll along.
There was a guy that asked me what kind of boat I had and where I sailed out of.
I told him I had a 36 foot Beneteau out of Winthrop Harbor.
He told me he had a 41 foot C&C that he raced out to of Belmont but that was too far away for him do any sailing over lunch.
I decided to wind up my chatting and closed out the chat room when I got an Instant Message.

“Are you really going sailing today?” it read.

“That’s the plan” I replied.

“Out of North Point in Winthrop Harbor?” it chimed.

“Yes” I replied, not really sure where this was going.

“Can I come?” The message asked.

I was a little surprised by the request. Very rarely do you get total strangers asking to go sailing online.
I did a quick check of the profile which only left me with a little unrest.
It just said she was female, her name was Amy and she was a student.
Then I had to ask myself, College, High School or Junior High?
I had a feeling I could get myself in to a lot of trouble if I wasn’t careful.
The chime from the IM brought me back to the present.

“Pleeeese, I really want to go” she pleaded.

I decided I would try to dissuade her from going and wrote, “I don’t know, I’m only going to be out for a couple of hours at the most.”

“That would be perfect! So I can go?” was the response.

I shook my head, not believing what I was reading.
I was about to write again when she chimed through again.
I looked over and ready then smiled a little in disbelief.
“Please, I really want to go. I’ll do anything if you let me!” it read.

My mind instantly slipped a notch when I read it. I was pretty sure I was dealing with a teen or just someone playing around.
I decided to play along a little and see where this was going.

“You should be careful saying things like that. You could get yourself in a lot of trouble” I replied.

The reply was a simple smiley face with a wink.

The next chime showed, “So does that mean I can go?”

I sat in front of my computer knowing I should just say no. But my gut told me I could say anything and this person wouldn’t show up.
I figured it was probably some 40 year old guy getting his jollies or something.
I decided I would let fate decide.

“Well, I am planning on casting off lines at 11am” I wrote.

“Cool, I’ll be there at 10:45” was the response.

“I’m Amy btw” followed.

“Bill” was my reply.

What had I just done? Did I really just invite a total stranger to go sailing; most likely a teenage?
Oh, my wife would kill me if she found out!

Then a thought occurred to me.
I quickly wrote back, “How will I recognize you?”

Her response was fairly vague, “I’ll be the cute girl with brown hair in jean shorts, a pink top and a bikini underneath.”

I looked around the room in utter confusion with myself.
My eyes happen to catch the clock and it was time for me to get going.
I sent one last IM to say I had to run.

“Cool, see you then” she sent.

I logged out and shut down the computer, and then I went upstairs to shower and get dressed.

“Nobody’s going to show up” I kept telling myself.

After my shower I put on my jeans and a button up shirt. I figured I would use the shorts and sandals that I leave on the boat for my expedition this afternoon.

With that I kissed my wife and kids goodbye and headed to work.

I got to work a little after 8. As expected there wasn’t a lot going on today. I busied myself with a few tasks and responded to a few emails before I looked up at the clock.

It was barely 10am. I decided that was close enough and grabbed my keys and sunglasses.
I got to the marina about 20 after and decided to give the boat a quick hose down to remove a little dirt and cobwebs from the deck and rigging. It wasn’t that bad since we had just been on it a few days before.

After cleaning things off, I opened the boat and went below to change out of my pants and in to my shorts.
I returned to the cockpit with the cushions and snapped them in to place. Then I removed the sail cover and connected the halyard so everything would be ready to go once I passed the breakwater. I then removed the spring lines and two of the dock lines in preparation to leave. I then went back and started up the diesel to warm it up a little before I headed out. I looked at my clock and saw it was almost a quarter till.

I decided I would head up to the main building to hit the head before I left, just in case my ‘company’ decided to show.
I didn’t see anyone on my short walk up. After I finished I walked out and looked out in to the parking lot and along the sidewalk.

“Just as I thought” I said to myself.

Then I turned around and almost fell over.
Standing on the dock side of the building up against the railing was a very cute little girl looking out over the boats.

She must have been between 14 and 16 (15 I found out later); standing about 5’3 with brown curly hair in a pink top and blue jean shorts.
I was in trouble now, I could feel it!

I walked out the door and she turned around. I first noticed her beautiful brown eyes, cute rounded nose and an almost perfect mouth. I then noticed the tie of her bikini top that help a very sweet set of small but perky breasts.
She stood before me with one hand crooked on to a large beach bag over her shoulder and the other down to her side.
She rocked back and forth slightly as I stood there looking at her.

“Bill?” she questioned, causing me to come back to reality.

“Amy” I questioned.

“Yep, that’s me” she smiled.

“You actually came” I replied.

“I hope it’s OK” she started. “I’ve always wanted to go on a sailboat.”

“It’s fine” I assured her and motioned the way for her to go.

We walked to the slip where my boat was patiently waiting for me.

“Wow, is this yours” she asked?

“Yup” I replied.

“It’s huge!” she continued. “You could like sleep on it and everything.”

“I do that from time to time” I replied.

I helped her on board and she walked back and stood in the middle of the cockpit holding her bag down in front of her.

“You can put that below if you like. Just place it behind the door on your left as you go down so it doesn’t roll around much” I told her.

Amy started to go below when I heard her say “Wow, there’s a kitchen and everything down here!”

I couldn’t help but laugh a little. I also couldn’t help notice her nice lean legs. I noticed that she wasn’t really tan either, but had a little bit a slight pink complexion.

“This is probably a bad idea” I said to myself, “and probably not my last one.”

I removed the aft dock line, leaving only one on the bow to hold us in place.
I was getting ready to go forward when Amy returned to the cockpit.

“Where are you going” she asked?

“Just to get the bow like” I told her.

“Can I help?” she asked.

I thought for a moment and figured if she was here, why not.
I told her to just pull the line up and when it was loose enough to pull it off the cleat and hang in on the hook that was hanging from the dock.
She did exactly as instructed and I slowly pulled us out of the slip and headed for breakwater.
Amy came back and sat on the settee near the wheel and I watched as her head darted from one place to another taking in all the sites.
As I left the protection of the harbor I pointed the boat in to the wind. I asked Amy if she would steer the boat while I set the sails.

“Really?” she said with an excitement in her voice. “What do I need to do?” she asked.

I explained she just needed to keep the boat heading straight in to the wind while I raised the sails.
She looked a little nervous at first but was doing just fine by the time the main was to its peak.
I moved over and started unfurling the headsail until it was almost out then I told Amy to turn the wheel to her right a little.
As the nose moved to port the winds filled the sails and caused the boat to lurch and heel.
The movement of the boat caught Amy off-guard and she stumbled toward the downward side.
I quickly reached over and steady her with my hand on your waist.

“Thanks” she said quickly.

“Sorry, I probably should have warmed you about that.” I replied.

I adjusted our course and sails to a beam reach which would give us a pretty nice ride out and back. I looked down I saw we were skirting along at a nice 6 knots. I shut down the engine and relished in the silence.

I sat down on the part settee by the wheel and Amy sat opposite me. She was still looking around taking in everything. I always delight at taking new people sailing.

“Wow, this is so cool!” Amy started. “Do you do this often?”

“We try to go most weekends” I told her.

Amy continued to amuse herself at exploring the different nooks and knobs in the cockpit.
I asked her if she wanted something to drink and she said, “OK.”
I locked the autopilot on course which caused another fascination with my guest and dropped below to grab to sodas from the icebox.
Once again my mind screamed at me, “What the hell are you doing? This is crazy!”
I calmed myself by just saying, “We’re only going for a short cruise, nothing is going to happen.”
When I returned to the cockpit Amy was sitting on her hands on the settee. I handed her one of the sodas and sat down on my side again.

“Bill?” Amy asked, “Do you think it would be alright if I work my bathing suit?”

Since I couldn’t think of a good reason why she couldn’t I told her to go ahead.
I watched as she removed her top and noted the slight bounce of her young firm breasts behind the small triangular fabric.

Then I watched as she rose up slightly to slide her shorts down. Her shorts were a little tight and I noticed that her bikini bottoms came down a little with them. For a second I almost thought I saw a wisp of pubic hair.
Just the thought of that, along with the sight of this sexy little thing in her bikini started to make things a little stiff for me.
Amy quickly adjusted her bikini and sat back looking at me through her sunglasses.

We chatted for a little bit and I found out she actually lived in Winthrop Harbor. She rode her bike down to the marina this morning to go.
Since her folks worked, she told them she was going to a friend’s house and they would probably go out to lunch or something.
That is also when I found out she had just turned 15 the month prior.

Red flags went up all through my head, only one head was stealing all the blood from the other one.
I sat there having our little conversation admiring her sexy body. I’m sure there were parts of the conversation I missed as my mind played out what she might look sitting there naked.

“Bill? Bill? Is everything OK?” she asked, snapping me once again out of my dream state.

I did a quick shake of my head to clear the cobwebs and told her everything was just fine.
Amy got a big smile on her face and I figured she knew I was looking at her.

“So, was I what you were expecting” she asked me out of the blue.

“What do you mean” I asked in return?

“I mean were you happy with how I looked when you saw me” she responded.

There were a lot of things that ran through my head that I wanted to answer, but I hoped for a polite one.

“I thought you were very beautiful” I told her.

I watched Amy’s face light up with my remark.
I also noticed the time. We had been sailing for nearly an hour. I told Amy to hang on and I turned the boat around and reset the sails for our return trip.

“Do we have to go back so soon?” she asked. The sound of her voice made my heart want to melt.

“Sorry, I only have a short time today, remember” I told her.

She nodded softly back.

As I sat back down and leaned back I saw Amy look up at me with a mischievous little smile.
I watched as Amy took off her glasses and stood up, placing on hand on the pedestal and the other on her hip.
God she looked sexy! Her legs were slightly apart, the sun seemed to simmer from her curls.

“You know” she started, “I said I would do anything if you took me sailing today.”
Her voice was slightly lower, more serious.

I watched as she moved her hand from her hip and moved it along the inner seam of her bikini top.

“That’s OK, there’s really no need for anything” is what my mind said.

What came out of my mouth was, “Really, and what did you have in mind?”

I could feel my cock expanding inside my shorts as she stood there smiling at me.

“Whatever you want” she repeated.

“My last boyfriend told me I gave great head” she continued.

I felt a jolt in my groin at her statement.
Amy cocked her head slightly to the side and said with a smile and a raise of her eyebrow, “You like that idea?”
I couldn’t help but smile back and nod.
Amy looked around, as if to make sure we were all alone. The she grabbed a pillow cushion and put it on the cockpit floor in front of me.
Amy leaned down to me and gave me a small kiss on the lips and then lowered her hands and started to remove my shorts.
Being the gentleman that I am, I helped removed my shorts allowing my erection to bare itself to the sun.
I moved my legs apart more to allow Amy more room. She then knelt down between my legs and took hold of my erect member.
My mind went foggy as I felt her hand wrap around the shaft and slowly start to stroke me.
Then I watched as she leaned down and let her tongue slide along from the base to the tip.
God that felt good!

She then lowered her head and took me in to her mouth. I could feel her tongue playing with me. Her lips were firm and I could feel her sucking me in.
Her boyfriend was right, she give a great blowjob!

She continued to slowly suck and stroke me as we sailed along.
I enjoyed every embrace she gave me with her talented mouth.
While the moans of pleasure were escaping my lips, I moved my hand down and took her hair in a bundle.
My hips moved slightly to match her strokes.

I moved my free hand down inside my legs and slipped my fingers under the bra of her bikini.
I could feel the firm mound inside. Her hardened nipple slipped between my index and middle fingers.
I squeezed them together trapping their prize.
Along with that came a small moan from my young little sucker.

She then used her free hand to pull her bikini top aside, fully exposing her wonderful breast.
The delight of her mouth along with the knowledge of what I was actually doing grew too much for me.

I felt my toes beginning to curl. The sensation scrambled up my legs and through my body.

I felt the rush of fluids as I let out a guttural moan.
Cum erupted from my cock inside Amy’s dainty mouth.
My body twitched in pleasure, two, three, four times.
With each shutter, Amy continued to stroke more and more.
As I finally felt my erection beginning to recede she released it from her lips.

I watched in amazement as she licked her lips then sat back on her heels and smiled back at me.

“How was that?” she smiled.

“Incredible!” I panted.

“Does that mean you want to take me sailing again?” she asked.

“Most definitely” I replied.

I took note of our position and figured we still had a half hour before we would be close to the marina.

“But this trip isn’t over with yet” I said.

I reached down and pulled Amy in to my lap.
Our lips met again and I could still taste a little of the salty flavor on her tongue.

I pulled her in and untied her top, letting it fall to the floor.

Then I placed her down on her back on the settee. I knelt beside her in the cockpit and kissed her.


Then I slowly kissed my way down and enjoyed her wonderful breasts. Her nipples were wonders on my tongue.
I heard the murmurs escape her lips and I let my hand slide along her flat stomach.
As I kissed along to her far nipple, my hand slipped underneath the fabric to her bikini bottom.

I could feel the soft hair underneath and continued down until I felt the wetness of her slit.
As I slid my finger along her wetness Amy moaned and grabbed my hair with her hands.
I knew I wanted to do more for her.

I withdrew my hand and slowly kissed my way down over her stomach.
I pulled the strings on both sides of her bikini bottom. Amy lifted her hips as I slowly pulled the fabric away exposed her small piece of heaven to me.

As I kissed my way down I noticed that her hair was triangular, but it didn’t look as if she had grown enough to actually shave it yet.
I caught her aroma on a breeze and I lowered my tongue to my prize.
Amy opened her legs to me, gripping my hair and pulling me in.
I listened to her moans and groans of pleasure as my tongue and fingers touched, tasted and teased her.
It didn’t take her long before the soft whimpers became broken pants of pleasure.
I delighted as I watched her body tense and felt it shutter.

I continued my assault as Amy tried to hold back the scream that was building inside of her.
Though with one last pressure of my finger within her she tensed and let out a series of sounds, each more passionate than the last.

I felt Amy pushing my head away softly and I knew I had met my goal.
Amy then pulled my head up and raised hers to meet mine.

We kissed as I felt her hands continue to grip and release, still feeling the waves of pleasure flow through her.
When we finally stopped she was still panting heavily.

I looked around and noticed we were getting kind of close to other boaters and the marina.
Reluctantly Amy put back on her bathing suit and clothes.
I too was sad to see her cover that delectable little body.
It seemed like the rest of the voyage flew.

I soon had the dock back at the dock. All was secure, the sails were put away and the engine silenced again.
We collected our things and headed back to the front building.
I offered to give her a ride, but then remembered she had her bike to ride.
She gave me a big hug and thanked me for the ride and “everything”.
She told she would love to go sailing again if I get an afternoon free. Only next time we can finish what was started on this one, if I wanted.

I kind of laughed and just responded with, “Anything to go sailing, huh?”

Amy looked back at me with that devilish grin, “Anything.”

I couldn’t get the grin off my face for the rest of the day.
Work seemed to fly buy. I kept checking the schedule to see I would have another day where I could slip away again.

And, as luck would have it, next Wednesday was going to be such a day.

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