Learning Legaleez Pt. 06

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A 27-year-old dot com CEO falls for his forty something attorney.

A spark is noticed during their first meeting. Later that day, they meet again in the attorney's office when everyone has already gone home.

The CEO makes his move and manages to get the MILF attorney naked.

After a short but wild session in the attorney's office, they head out for dinner and then spend a sex-heavy evening together before they fall asleep.

After a morning sex session, they decide to spend their weekend together on Mike's boat.

Mike and Jill just finished their happy hour with Jill sitting in Mikes lap, fucking slowly while enjoying a G&T.

Jill and Mike are now about to head into harbor for a lakeside dinner.

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"I'm thinking we go below and clean-up before I take you to dinner," I proposed, "are you going to let me dress for dinner, or do you want me to go naked?"

"Where are we going?" Jill asked with a smirk, not answering his question regarding clothing.

"It's a place called Gianni's. It's right on the water so we can dock and walk in. It's an Italian steak house," I replied, "They frown on public nudity."

"Sounds nice. I'll let you wear clothes, but no underwear." Jill replied, again looking at my cock.

"How gracious of you," I joked, "as soon as I'm showered, we can pull anchor and get underway."

We both cleaned up and dressed for dinner. I wore a pair of golf shorts and a golf shirt. I was worried about the imprint of my junk being too obvious for a public venue. But Jill made the rules and I followed. Since I was ready, I went back to the cockpit, pulled up the anchor and started a slow cruise in to harbor.

A few minutes later, Jill emerged from the cuddy below wearing a yellow sun dress. The contrast of the yellow dress against her dark hair and tan skin was absolutely striking. I couldn't help letting my eyes wander all over her as she emerged.

"What?" she asked, noticing my visual interrogation, "is my hair funny or something?"

"I've just never seen a woman look so good," I said, smiling, "you look incredible, Jill."

"You're just saying that because I let you see what's underneath," Jill smirked, "I think you think I'm easy."

"I'm the guy standing here with no underwear by your command, and you're easy?" I scoffed.

"No, you're a pushover," Jill chided, "that's different."

We motored across the bay at a leisurely pace making our way to the harbor. We pulled into an open slip and secured our lines. As we were preparing to disembark, Jill leaned in to kiss me, she reached between us and started stroking my pants through my golf shorts. The lightweight fabric felt good against my shaft and I started to get erect.

"I wouldn't want you to walk into dinner with a bulge in your shorts," Jill moaned, "people might think I'm too hot for you and you can't control yourself."

"Well, they'd be right about you being too hot for me," I laughed, "but maybe they'll just think my pants always look like this."

"Don't flatter yourself," Jill teased, "I don't think anybody will notice, it's not like your Tommy Lee or something."

"Get off my boat," I said, in jest, as I helped Jill step onto the dock.

As we walked down the dock toward the restaurant, I was self-conscious about what might be showing below the belt. As the maître d' walked us to our table, I noticed a few glances by some of the woman already seated at their tables. Fortunately, most people were looking at Jill.

We enjoyed dinner and a few cocktails and then made our way back to my boat. The dock kid helped us clear the lines, I tipped him, and we were on our way out into the moonlit bay.

"Clothes," Jill said, holding out her hand.

"What? So, I'm gonna be naked again?" I asked.

"Well, I can't fellate you with your clothes on, but hey, you're call," Jill turned as if to walk away.

"Wait!" I said, pulling my shirt over my head and then quickly stepping out of my shorts.

Jill took my clothes and headed down the stairs into the cuddy. I assumed she was putting my clothes away and changing out of her dress into something more comfortable for the evening. I monitored our course as we headed to a secluded cove.

When she emerged from the cuddy, she was as naked as I was. She sat in the cockpit next to me and watched me watching the horizon.

"How long until we anchor?" Jill asked quietly, "I'm gonna need that mouth of yours again."

"Wait a minute," I protested, "I just took my clothes off because you offered your mouth to me."

"I did; however, I never stipulated a time," Jill laughed, "you're so imprecise with language."

"We have about 10 minutes until we anchor," I indicated, "that oughta give you plenty of time."

"I want to take my time and savor it," Jill said as she took my cock in her hand, "oh, but I forgot, you never last very long, do you."

"Ouch!" I said, feigning insult, "you really have a low opinion of my staying power."

"Staying power doesn't matter when you get hard again in 30 seconds like you do," Jill laughed.

Jill waited patiently while I found our spot on the leeward side of an island. Once I dropped anchor and made sure our mooring lights were on, we were set for the night. I looked around the cove and was pleased to confirm that we were the only boat moored here this evening. The location was nice and private, and the island blocked almost all the evening breeze.

"The anchor is set," I said, "why don't we head below deck for the evening."

We entered the air-conditioned cabin below deck and I turned to close and lock the companionway.

"So, we'll be safe here until morning?" Jill asked, "do we need to worry about pirates or sea monsters?"

"Don't worry about that," I smiled, "you have me to defend your honor."

"Oh, the guy who lets me force him to strip naked is going to protect me?" Jill laughed, "I hope you're packin' more than what I can see from here."

I picked Jill up in my arms and carried her to the bed. We kissed as I lowered her onto the soft duvet that covered the queen-sized bed. Neither of us noticed the low hum of the generator and air-conditioner, or the slight rocking of the boat as we got comfortable in the center of the bed. My 8-inch cock was again at full staff driven by the constant arousal that this woman created.

It didn't take long before I had to taste her again. I was working my way down on her when she decided to roll on top of me and rotate into sixty-nine. Jill's ass and pussy were just above my face as my hands caressed her thighs and ass. I couldn't wait to spend the rest of the evening with this woman seeing how much pleasure we could impose upon each other.

I felt my hard cock enter Jill's warm, wet mouth and I moaned with delight as I lifted my head to get a taste of her perfectly manicured crotch above me. As she took her time running her tongue across my frenulum and glans, I ran my tongue between the folds of her labia and flickered my tongue softly across her clit. I loved my view from this perspective, it was like I was enveloped in sheer carnal beauty. I don't know why, but I couldn't get enough of this woman.

"God, Jill, you taste so fucking good," I said from below, as I took long licks from her clit all the way up her ass crack.

I could feel my cock starting to enter Jill's throat as she took more and more of me. I loved this position, but I often found it hard to concentrate when we were both doing our best to get the other to orgasm first. Jill knew I had a hair trigger, and she didn't seem to mind my lack of endurance as long as I was ready to go again in a few minutes.

I was almost certain that Jill knew the effect she had on me. She was confident enough to know that she was the ultimate phenotype of the type of woman I desire. A striking brunette with steely blue eyes and a fit body matched with a wicked smart mind and a sharp tongue that could deliver humor or humiliation in the blink of an eye.

Soon, I could feel myself going past the point of no return. My tongue was lightly flickering on Jill's clit as fast as I could make it go. Jill sensed I was close and pulled off me, sitting up so that I could focus on her orgasm first. As she sat up, the two beautiful, tanned orbs of her ass enveloped my face. It was sublime.

"That's it skipper, use that tongue to get me again," Jill moaned from above me.

"Fuck, you've got a talented mouth," she moaned, as she rode my face making sure she got exactly what she wanted.

"I haven't cum this many times in a weekend since the last time I was on a rich kid's boat," she continued.

"Eat me, Mike, I love it when you eat me," Jill whispered at a level I could just barely hear, "you're fuckin' perfect."

Jill's hands were still wrapped around my cock, but I felt them move onto my thighs to support her weight. I knew that this meant she was getting close, so I stayed focused on her clit and sucked it into my mouth to stimulate it even further.

"Oh my God," Jill moaned, as I could feel her spasm.

Jill writhed on my face for a few seconds and then her spasms grew even stronger. I knew that I had delivered a powerful orgasm and I wanted it to continue. I took long licks across her pussy and up the crease of her ass as Jill's orgasm peaked. Then, I rolled her over and flipped myself into position so I could finally enter her and start fucking.

Jill's expression was priceless as I started hammering away, extending her orgasm into extra innings. I was fucking her like a stallion, taking long, rapid strokes at full depth. Our bodies were making slapping noises as I continued to fuck my attorney into oblivion. Jill was lying back helpless as I delivered my sexual onslaught. Somehow, I was able to delay my own orgasm enough to deliver an epic fuck.

Jill's looked up at me, her face frozen in an expression of surprise maybe even disbelief. I reached my forearms under her thighs and pulled her hips up into my loins. I was sitting up on my knees driving my cock with abandon into my 40-something victim. Her only recourse was to lie back and spasm as her orgasms came in waves.

I watched my cock working like a piston into Jills shaved cunt. I couldn't remember another time when I was this hard or this engorged. Jill's moans increased in volume and pitch as I delivered my shaft all the way to her cervix. Jill's arms were over her head as her body flopped and I hammered away like a fiend. The sensation of completely ravishing this woman started to overwhelm me. It was as if I was watching the action from outside my own body. But it was my body, it was my cock going deep inside this beautiful woman, and I was starting to feel a release building in my balls.

All I could do was moan as my orgasm arrived. I felt my balls contract and my cock started throbbing as I came hard. I tried to keep thrusting as I shot my load, but my orgasm was too strong. I fell forward onto Jill's body and tried to hold myself up while my cock continued firing rounds. It was like I had two or three orgasms all at once, my body was rocked by the sensations.

Jill and I lay there silently for a minute, the only sounds were the hum of the generator and the flow of our breath. We were still joined at our hips as I lifted my head to look into her eyes. Jill was wearing a satisfied smile that I hadn't seen before, I liked it a lot. I smiled back at her and kissed her softly on the lips. I pulled her into my arms, then lifted her up and carried her to the shower while I was still inside her.

"I think we both need a shower before bed," I said as we crowded into the master head, "the water might be a little chilly, I'm not running the water heater."

Jill and I entered the tiny shower together, washing off the sex and sweat from our day together. I was still intoxicated from what I had just experienced, my mind running on thinking that we still had the entire night and all day tomorrow together. We quickly showered and stepped out to dry off. Jill had still not said anything since we had finished on the bed, it was unlike her not to make a smart-ass remark at my expense.

"Is everything OK?" I asked as I carried her back to bed.

"You can't just bludgeon an old woman with that big tool of yours and just expect me to be OK," Jill answered in a tone that concerned me, "she might start to get ideas about a future together."

"Yeah, like how about all day tomorrow, and then next weekend?" I replied, smiling at her as we both lay on the bed, "I've never felt this way about anyone before, Jill."

"I have no idea how I feel about you, but I want the use of your mouth and cock on a regular basis," Jill laughed, "besides, you can't have feelings for me, you're barely old enough to drive this boat."

"Speaking of boats," I said, "I'm going to go up and check everything before we settle in for the night."

"Oh, we're settling in, are we?" Jill replied, "I was just getting started."

I shook my head and walked up the companionway, unlocked the door and slid it open so I could enter the cockpit. I grabbed a flashlight and walked up on the bow to check the anchor. I confirmed the anchor was holding and made my way back to the cockpit to check the gauges for temperature and fuel. All looked as it should. As I was sitting in the cockpit, Jill emerged through the companionway with a cocktail in both hands.

"What's this?" I asked as she handed me the lowball.

"It's a rum and coke, baby," Jill said, "you've got a swanky variety of Cuban rums down there just waiting to be defiled with good old American sugar water."

"Cuba Libre!" I toasted, as I took a sip, "this is absolutely perfect."

"It is nice having you captive on this boat," Jill said as she looked off into the dark horizon, "you seem so much more relaxed, and you haven't even looked at your phone since we left port."

"I love it out here on the water," I explained, "it's like we're in another world even though we are just a mile or so away from shore."

"This must go over well with the bimbos you bring out here," Jill said sarcastically.

"You're the first bimbo I've invited out for a weekend," I said looking back at Jill, "I'm serious."

"Is that so," Jill replied, "well then, consider me flattered."

We sat in the moonlight quietly sipping our rum and cokes. It was a perfect ending to a perfect day. I didn't want the time we had left to pass too quickly.

To Be Continued...