Lessons On The Water

The summer after my sophomore year in college, I got a job working on boats at a local yacht club. On weekends, I often was asked to crew during the one-design PHRF races. So people knew I was a pretty good sailor and knew my way around boats.

One day I was finishing ups job cleaning and oiling the teak on a sailboat, when one of the launch guys came down and asked me if I would be up for giving some lessons to one of the members on their 40 sloop.  I love sailing, and love to make a little extra beer money so readily agreed.  Great he said, Alison will be down in about half an hour.

That gave me a little time to clean myself up, so I went up and took a shower in the clubhouse.  Half an hour later this late 40's woman shows up and introduces herself as Alison.    Alison is a pretty, in shape from what can only be from playing a lot of tennis and golf. She smiles a smile that lights up my day and asks me if I am set to go. Sure, I say.  I am always ready to sail.  We go down to the dock and get a ride out on the launch to her boat.

Since it's her husband's boat, she sort of knows the layout and tells me so. We get the sail ties off and everything set then fire up the engine and motor out of the anchorage. Once we have the mainsail rated and the jib set we head out of the harbor to the bay.  It becomes clear early on that Alison's husband is one of those guys who yells a lot as he sails - barking orders to others and not really helping to teach others.  Alison says so. 

As we are sailing, Alison starts to ask me some questions to get know me. Where do I go to college, what am I interested in doing after I graduate, and what I do for fun.  I tell her I am working to help pay tuition and to hopefully get a better car than the shitbox I currently have.  

So all you do is work, she says.  

Yeah mostly.

Don't you have a girlfriend?   

I tell her that my girlfriend broke up with me after spring break to start going out with a guy on the baseball team.

Oh that's terrible, Alison says. And this is where the conversation turned. So what do you do?

I work and I sometimes go out with some friends and have beers.

No, Alison says - what do you DO?    Oh your blushing. You can tell me, I know. I have two sons and I know.

I stammer that I sometimes take care of myself.  While I am embarrassed by this, I am also getting an erection talking about it.

It's Ok - she tells me. I understand you need to masturbate to take care of your urges.

Yes, that's it I say.

Well, no need to be embarrassed. I need to take care of my needs too. My husband is either traveling for work, or off playing golf. He never seems to have the time for me. So yes, Tim, I masturbate too.

Tim, I see that this conversation has gotten you a bit worked up.  We are far enough off shore that we can "skinny sail"  like skinny dipping, but  sail naked. Alison starts to pull her shirt off and then unclasps her bra and tosses them down below. Come on Tim, shed those shorts and t shirt.  

As I pull my shirt off and then peel my shorts off, Alison stands up and pulls down her shorts and panties.  She has an amazing body. Her tits had a little sag to them, but are sexy and gorgeous in my eyes. Her nipples are scrunched up and hard. Clearly, the sea breeze is affecting them. She trimmed her pussy hair so that it was not a big triangle of hair but more like a wide mohawk of dark hair.  I could see her outer labia quite well as well as a fairly engorged and (much larger than my recent girlfriend's ) clit.

My God Tim, I see our conversation has really excited you. Just look at your hard cock.

My cock was throbbing with my heartbeat.   

Why would your girlfriend give up that hard cock? It's beautiful.

So you really just take care of yourself these days ? She asked.

Yes, I assure you, Alison, that's my sex life.

Show me. Show me how you masturbate. My husband has always been very shy about it, and while I once in a while could hear my sons masturbating, I never saw them.  Show me how you make yourself cum.

OK- but we'll need to put the boat on autopilot first. 

Fuck,  touching myself in front of this pretty naked woman, out in the open was heaven.   Alison spread her thighs to show me her womanhood. As I slowly stroked my hard cock, I could see how wet she was. As I touched myself she moaned a little as she watched and she started to finger her pussy, running her finger over her slit and teasing her clit. 

I had never seen a woman masturbating in person. My girlfriend always denied she masturbated.   It was the absolute sexiest experience I had had to date.   

UH Uh UH I'm cumming she moaned as her hand gained speed.  This put me over the edge -   Me toooooo. I shot my cum across the cockpit, and some landed on her feet as she reached her orgasm.   FUUUUCK she sighed. That was awesome.

I'm going to need some more lessons this summer.   

Alison and I met many more times and did avlot more before the summer was over.  More to come.