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. She had her goblet of wine; I had my generous pour of scotch. “So, what brings you here, sailor?” “Well, I’m a full-time liveaboard, a widower, and I’m just cruising around searching for new adventures. Stopped here to see about getting my boat cleaned up a bit. It’s turned into quite a bachelor pad I’m afraid. What about you? What’s your story?”
We had finished our drinks and she got up to refill them before she responded. “Oh, kinda boring really. Married out of college to an asshole. He seriously abused me physically, sexually and emotionally, so I divorced him. I was working as the receptionist at an investment house when I met Bill. He had been recently widowed and we started talking. One thing led to another and, well, here I am. We alternate between Second Chance and his villa in the south of France.” “Wow! That sounds really exotic. You must be very happy.” “Not really, sailor. Yes, I love the money and the lifestyle. But, between you and me, Bill’s quite a bit older than me. He’s more than twice my age. So, everything’s there except, well, except my love life.”
She was halfway through her second goblet of wine, the bottle nearly drained, and she opened up. “You see, Bill can’t really get it up anymore. I try and try. I’ve tried everything. But there’s only so long you can suck on a limp dick. Only so many times you can do a provocative striptease. Even porn doesn’t work on him. I mean, I’ve had some wild and crazy sex. My abuser ex used to make me do raunchy, nasty, dirty sex things so I’ve been there. In fact, sometimes I want to go back, just for the sex. That part of the abuse I loved. It was the hitting and the emotional shit I couldn’t deal with.”
At this point Bill arrived. He poured himself a drink and joined us. He certainly was much older than Jenny. He looked old and frail. “Howdy neighbor! Welcome aboard Second Chance. How long you here for?” “Not sure just yet. Want to see how things go first.” “I’d sure like to see you stick around for a while sailor. If there’s anything I can do to make that happen just holler. My Jenny here seems to have taken a liking to you. She insisted that we invite you over and was overjoyed when you accepted. Haven’t seen her that excited in some time. She hasn’t made any friends here so maybe she can show you around some. You wouldn’t mind, would you sweetheart?” “It would be my pleasure, honey. Just don’t get all jealous if I spend time with sailor. I’m still married to you, remember?” She held up her left hand showing the huge diamond. “And, darling, if I’m out for an afternoon, we have that maid service that can fix you meals and get you your meds. You OK with that?” “That’s fine, Jenny. I just want you to be happy and enjoy what this city has to offer. Show sailor boy around and don’t worry about me. I’ll be fine.”
Wow. That took an unexpected turn. And even though Jenny was legally married, it was obviously only a marriage on paper. I replied “Thank you, Bill. That’s awfully generous of you but I can’t just commandeer your wife like that. It wouldn’t seem right.” “Nonsense, sailor. She’s bored, I’m too old and you seem available. Show her around, show her a good time. You’d be doing me a great favor.” “Well, I appreciate that, sir. And thank you for having me aboard Second Chance. I’ve enjoyed your hospitality. I think I’ll excuse myself now and go find some dinner.” Jenny piped up, “Oh, I know somewhere you’d just love. Let me take you there. Bill, I’ll have dinner sent to the boat, how’s that?”
Jenny drove us to a quaint French restaurant in her late model convertible Mercedes. Classy. The restaurant was dimly lit and the maître de seated us in a corner booth, romantic candlelight and all. She insisted on sitting right next to me. We ordered drinks and food and as soon as the waiter left, she started toying with my crotch. Fortunately, there was an overhanging tablecloth because she soon had my zipper down and had fished out my cock. She stroked and fondled it until it was erect. She was clever at how she could jack me off without being obvious. Before I could reach climax, our food arrived. Our dinner talk ranged from A to Z, flitting from topic to topic, our minds clearly on something else.
After dinner we left to drive home but she took a different route. She pulled into the Hilton and tossed her keys to the valet. Whoa! Once in our suite she called room service. Not saying a word, she disappeared into the bath. I just sat there trying to imagine how I got there and what was next. Shortly she emerged from the bath in the oversize terry hotel robe. She responded to the knock at the door and handed the bellboy a $50. She wasn’t saying anything, just going through the motions as if she’d done this before. She poured us drinks, handed me mine and said in a low, seductive voice, “follow me sailor.” She nearly glided into the bedroom, turned to me, and planted a big kiss on my mouth. We kissed passionately for a minute, exploring with our tongues. When we broke, she said “Well, sailor. Time to drop those drawers.”
As my pants hit the floor, so did her robe. She had a flawless body, a beauty to behold. “I’m trying to be cool, calm, and collected but I must admit that my pussy is not. Ever since you arrived, she’s been tingling. At the restaurant, fondling your cock, she started twitching and burning. Now she’s on fire, anticipating that your dick will fill her up and quench that yearning.” With that she lay on the bed and spread her legs wide. Her pussy was as flawless as the rest of her body. “Come on, sailor. Come mount me and put that fire out. I’m ready.” I climbed between her legs and she instantly reached down, grabbed my dick, and started rubbing it up and down on her slit. She was primed, it was wet, and she expertly guided it into her pussy. As I leaned forward it slid in easily. “Oh, Christ! Holy fuck that feels good. She’s been craving this for a while. Shit that’s nice. Let me have your cock, all of it. Fuck me, fuck me, please. I so need this. It feels so fucking damn good.” I was slowly stroking her sloppy wet cunt as she was oohing and ahhing. Her pussy was nice to fuck, all swelled up. As I increased the speed, she raised her legs up higher allowing me to wrap my arms around them and get deeper into her twat. “Oh, yes! Yes! Pound that pussy, pound it hard! Your cock feels so fucking good deep in there. Pound me hard till you hit bottom. Pound it! Pound it!”
I did my best and slammed my cock into her sloppy wet cunt. It had opened up now and my dick had no trouble as it easily rammed in and out of her. My balls were slapping against her ass adding to the sounds her dripping wet pussy was making as my stiff rod pumped in and out. It didn’t take long. She was so primed that soon she screamed out “That’s it! That’s it! Oh, fuck YES! FUUUCCCKK YEEESSSS!” Her body jerked, her hips thrust up and she pushed her throbbing cunt up on my dick.
Her ecstasy and enjoyment worked on me too. As she was jerking and thrusting I, too, came long and hard deep inside her, shooting a massive wad. As I leaned back my dick slid out of her gaping pussy and my cum wad started oozing out of her clean-shaven pussy. It dripped down to her tightly puckered asshole covering it with thick creamy cum juice. I wanted to use my cum as lubricant to fuck her ass, but my dick was spent. So, I used it to lube my fingers and started finger fucking her asshole.
This she liked as she raised her legs back up saying “Oh that’s nice, sailor, that’s nice. Get two fingers in. Work ‘em in slowly and gently. After that massive orgasm, just finger fuck my ass gently for now. I’ll let – ooohhh that’s nice – I’ll let you go to town and fuck my ass properly later. But for now – yes, that’s it – slow and gentle. Two fingers, just slide them – oh, yeah, oh yeah.” Disregarding her directions, I quickened the pace. I started finger fucking her tight asshole hard with 2 fingers. Within a minute I was pounding it hard and fast, and she was thrusting her hips again. Without much warning, she screamed out “OHH SSHIIITT” and squirted a big load from her pussy. It made a giant wet spot on the bed.
“You’re going to have to answer to housekeeping for that you know.” “Oh, I doubt it. Bill or one of his companies owns the hotel.” We drove back to the marina, and she gave me a socially acceptable hug as we went to our respective boats.