Ch. 17 – Jenny, My First Second Chance

Chapter 17:

Jenny – My First Second Chance

Life on a boat, as a bachelor, involves a lot of alone time, a lot of solitude. And when in port there’s a huge difference between being on a mooring ball and being at a dock. On a ball you’re isolated, your dinghy is your connection to civilization. A slip at a dock involves neighbors. It’s kinda like – which hole is better: pussy or asshole. They’re both good, just different.

For my next adventure I chose a large marina in a big city, all docks, no mooring field. Not usually my style but I really wanted to get my boat cleaned up. I radioed ahead and was assigned slip 69 on dock O. As I maneuvered into my slip the typical crowd of neighbors appeared to help catch dock lines and check out the new guy and his boat. It was late in the afternoon, almost sundowner time, and before I had finished adjusting my dock lines, I had 3 invitations for cocktails. Wow! Maybe this would turn out better than I thought. Everyone seemed paired up, husband and wife, so I accepted the invite from the couple with the hottest wife. The husband was pretty old; the wife, only in her late 30s, was obviously his trophy wife.

An hour later after sprucing up a bit, I knocked on their boat. It was a large power boat, costing a million or more, clean and well appointed. “Permission to come aboard, Captain?” The admiral stepped out of the salon “Of course! Permission granted.” I climbed the boarding ladder to their spacious aft deck. She stepped right up to me and gave me a big hug, making sure to push her ample breasts hard into me. When she pulled away, she planted a big wet kiss on my lips.

“Welcome aboard Second Chance. Please make yourself comfortable. I’m Jenny, my husband Bill is still napping. He’ll be down shortly. What can I get you from the bar, sailor?” With that I offered her the bottle of wine I had brought as a hostess gift. “Oh, how nice! Beaujolais, my favorite. Thank you. Now, what would you like?” as she motioned toward the wet bar, fully stocked. “I’ll have scotch on the rocks, please.”

As she prepared my drink, I admired Bill’s trophy wife. Pretty typical of the trophy wives I’ve seen. Long bleached blonde hair cascading past her shoulders, large fake breasts, tiny flat stomach flaying out to nicely shaped hips easy to hold onto, and sculpted thighs. She had on a skimpy little outfit. Loose fitting see-through button blouse, no bra of course, and unbuttoned enough to show ample cleavage. She was proud of her $10,000 boob job and wanted everyone to admire them. On the bottom she had on mini-Daisy Dukes, slung very low and cut very high. There wasn’t much fabric there. Lots of makeup, thereby completing the picture of the typical trophy wife. Very attractive specimen, taken as a whole. Not really my type, however….

We settled in on the deck chairs.