Sailing with Samantha


"Damn!" I said. Sam giggled -- she seemed to think it was fun.

"I've got to get those sails down." I told Sam. I quickly got the engine started. "Take the wheel and point into the wind and hold her there."

I grabbed my shorts, quickly pulled them up without even bothering to zip, then I jumped up on top of the cabin and got both sails secured. When I returned to the cockpit, Sam was standing there steering -- still naked. She was amazingly beautiful.

"Don't you want to get dressed?"


"Why Not?"

"I want to do it again."

I felt my cock stirring once more. So, I locked the wheel amidships -- with the engine turning at low speed, it would keep us heading out into the Gulf, and away from traffic, without the wind affecting our course.

Sam came around from behind the wheel and pulled my shorts down. She knelt and took my soft but growing member in her mouth; she swirled her tongue around and over the head. As she started pumping her mouth up and down my shaft I became fully hard again.

She removed my cock and said, "Oh John ... I never felt a man's penis grow in my mouth before. That's so ... so ... special. I love it!"

"You've sucked cock before?"

"Yeah. That's one way you keep boys out of your panties." She said with a naughty grin. "I want to taste your cum, John. That's one thing I've never done. I never let a boy squirt in my mouth but I really want you to so I can taste it and swallow every drop. OK?"

All I could think to say was "sure."

As we motored slowly away from shore, she gave me the most exquisite blow job and I did finally erupt in her mouth. A little bit of cum dribbled down her chin and some fell onto her chest, but to her credit, Sam did swallow most of it. When I was done she kept pumping my cock with both hands. I never thought I had it in me to climax twice inside an hour and still maintain an erection; but that was the effect Sam had on me that day.

"Wow. I love the taste and the feel of it hitting the back of my throat. Each squirt ... and having my mouth full of you warm cum. It was beautiful."

She wiped the bit of cum from her chin and licked her fingers. "Yum!"

Then she pushed me down onto the cockpit seat and straddled me and grabbed my still hard meat and shoved it up inside herself.

She rocked back and forth and lifted her hips over and over for what seemed like another hour; though I am sure it couldn't have been so long. She had more orgasms -- I've never encountered a woman like Sam who was so easily pushed over the edge. She was just amazing. And she was so vocal telling me how it felt having me inside her and how it made her tingle and feel dizzy. Finally, after who knows how many more climaxes, she sort of slid over to one side and curled up on the cockpit cushion without saying a word and was asleep. I had not cum again -- gee whiz, wonder why ... could it be I'm an old man? I'm certainly not a kid anymore but Sam sure made me feel like one again that Sunday afternoon.

I pulled on my shorts one more time and cranked the engine up to full speed and turned the boat back towards the marina. It took well over an hour before we were heading back into the marina's breakwater. On the way back, I went below and found the pair of cut offs and Sam's tank top were she had left them when she had changed into her bikini. I managed to get these on her while she slept so she wouldn't be lying on deck naked when we got back to the dock. She sort of half woke up while I dressed her, but then drifted off again.

I pulled the boat into my slip and tied her up. Then I gently shook Sam awake.

"It's time to go, hun."

She looked up at me bleary eyed. "Huh?"

"You've been sleeping. We're back at the marina." As I said this, she wrapped her arms around my head and kissed me again. I had to push her away; there were people around who knew me and Karen and they would wonder what I was doing with a young girl passionately kissing me.

"Not here!" I said.

We packed up our stuff and took everything to my car. As I was pulling out of the marina parking area, Sam got on her cell.

"Hi mom its me. Oh Mom, we had such a great time ... I got to sail the boat! It was fantastic. Oh ... no. Uncle John is dropping me at Cynthia's ... she called while we were sailing and wants me to go over and spent the night at her place. It'll be the last chance I get to see her before I go to school. Is that OK? Sure. Yeah, I'll call in the morning ... yeah, I'm sure she can give me a ride home so you won't have to be late for work. Bye. Love you too."

I asked Sam where Cynthia lived so I could drop her.

"I'm not going to Cynthia's."

"Huh?" I said, confused.

"You said Aunt Karen wasn't getting back from Boston until Tuesday, right?"


"I want to sleep with you tonight. I want you to make love to me again and then fall asleep in your arms."

"Sam ..."

"Please?" She begged.

So that's what we did. We went to bed right after dinner and I fucked Samantha for another hour or two. She wanted me to fuck her in every conceivable position. She told me that her previous two experiences with her boyfriend had both been missionary. Sam said it had been nice her first two times, but she wanted to learn everything; experience everything -- she was insatiable.

When we did finally manage to go to sleep we were "spooned" - my front pressed to her back - and my cock was still inside her. I remember just ever so slowly moving in and out of her. The next thing I knew, it was morning, and I awoke with Sam's mouth on my hard cock. Before I could get the sleep out of my eyes she was astride me and riding me like a bronco rider. She called her mom on her cell while I was still inside her, for heaven's sake!

"Mom. Yeah, still at Cynthia's. Listen, she wants to drive over to the mountains and go hiking. Yeah, I know ... I'll work on packing tonight when I get home. Probably late ... I don't know ... we'll be fine, honest ... no, she's lending me some of her cloths ... I tried on a pair of her hiking boots and they fit fine. Geez Mom, I'm not a kid any more ... well, the cell phone isn't going work up there, you know that. You've been up there before. Yes ... see you tonight. Late. I love you too ... bye."

All the time she talked she was grinding away with my stiff dick deep inside her. After her call, she just grinned a very sly grin.

"You're something else, Sam." And then I came inside her for the first time that second day. She lifted her hips off my cock and reached underneath to retrieve my cum as it dripped from her pussy.

"Hmmm ... so yummy." She said, licking her fingers. She repeated this several times, kissing me once in between to share the taste of the pussy juice / cum cocktail with me. I had to admit, it tasted pretty good.

We spent most of Monday in bed. We showered and fucked in the shower. We had lunch and she wanted me to fuck her on the kitchen table -- so I did. I came three more times that day and by ten o'clock that evening I could barely walk. My pubic bone above my cock was sore from pounding Sam so much of the day. How she could take it, and still want more, was beyond me.

I drove her home late that night. She made me drop her at the corner so her mom wouldn't see my car. She kissed me passionately, one last time.

"Thank you John."

"For what?"

"For teaching me what it is to be a woman."

I opened my mouth and was desperately trying to think of something appropriate to say, but Sam didn't wait.

"I want to go sailing with you again next summer ... just you and me again. OK?" And then she jumped out of the car and was gone.

Sailing with Sam never happened again. The following year I heard from my kids, who stayed in touch with Samantha, that she had signed on for a "semester at sea" program -- she was double majoring in marine biology and oceanography.

But I'll never forget sailing with Sam ... for as long as I live.

Report Story

byjoan658© 6 comments/ 162964 views/ 54 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

2 Pages:12

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartcpt_ken, Putsin and 52 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (6 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (6)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: