Learning Legaleez Pt 05

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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 Saturday together...

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"Hey, did I ever tell you that I had a boat?" Mike said, as he and Jill ate breakfast.

"What kind of boat?" Jill asked, taking a sip of her coffee.

"It's a 37-foot Back Cove. It's kind of an upscale Downeaster," I replied, waiting for any sign of interest from Jill.

"Are you proposing that we spend the day on the water?" Jill, asked, "Does your boat have air conditioning? Because it's going to be over 100 degrees today."

"As a matter of fact..." I started.

"Of course it does!" Jill interrupted, "So you're rich, you're good looking, and you have an air-conditioned yacht. I guess that makes up for the fact that you only last 2 minutes in the sack," Jill laughed.

"Hey, I would last a lot longer if you didn't look the way you do. You have nobody to blame but yourself, Gramma," I countered with a smile.

"So, I bet you want me to spend the weekend out on the water with you wearing just a bikini?" Jill asked with a smirk on her face.

"Do you have a white one?" I asked, trying to keep a straight face.

"Oh, you want to pick the color now too. Everyone knows that white bikinis become transparent when they get wet. But I guess there very little risk of me getting wet around you," Jill smiled.

I reached for my phone and started a call.

"Hey, we're talking here, who are you calling?" Jill asked.

"Monica loves my boat," I said, holding back a smile.

"Monica is probably a 22-year-old blonde with special needs," Jill said, sitting back and crossing her arms, "What are you going to talk about all weekend, puppies and her Instagram account?"

"There is no Monica, I just didn't want to look so desperate," I confessed, "It's a nice boat, I think we'd have a wonderful time.

"I'll pack my white bikini," Jill said, this time her smile was warm and without any sarcasm.

"Awesome!" I exclaimed, jumping up from my chair, "You go pack, and I'll clean up the dishes. Maybe pack some clothes for dinner tonight, I know a place we can dock and enjoy dinner on the water."

Soon we were headed for the marina, packed up and ready for a weekend on the water. We stopped on the way for provisions, we were well stocked for a great voyage. I felt like I was in high school again, running off with a hot upperclassman on my parents' boat. Even though it was now my boat, and the upperclassman was my hot lawyer.

As we walked up to my boat, Jill looked at the name on her hull. Her name was "Summer Wind."

"Summer Wind," Jill commented, "I love that name. If there was a woman's name on the transom, I would never board her."

"It's bad luck to rename a boat," I replied, "When I get a new one, I might name it 'Jill's Bikini'."

"Hey, you haven't even seen my bikini yet," Jill laughed.

"I've seen the tan lines it leaves, and I am already a fan," I smirked.

I opened the transom door and boarded "Summer Wind". I held my hand out to Jill and she boarded leaving the provisions on the dock. I showed her around quickly and then took her below deck to show her the quarters.

"There's a lot of room down here, and a lot of teak," Jill laughed, "I love it."

"...and it's air-conditioned so we can sleep in comfort without worrying about bugs," I bragged.

"You think you're gonna get much sleep, Skipper?" Jill said smiling.

I grabbed Jill and kissed her. The kiss went on and on. My hands were all over her body. I couldn't stop myself from trying to rip her clothes off right there and taking what I wanted.

"Hey, hey!" Jill stopped me, "Let's get unpacked and get out on the water before you start trying to park your submarine in my channel."

"Aye Matey!" I replied, laughing as I headed out to load the provisions. I quickly had our coolers and clothes on board.

"I'll get the engines running so we can start the A/C," I explained, "Maybe you could put away the provisions."

Setting Sail

Soon, we were out on the lake, the twin screws making a low rumble. I was in the cockpit, setting our course when I turned to see Jill coming up from below deck in her tiny white bikini. The top barely covered her c-cups with a tiny triangle over each nipple. The bottoms were just another tiny triangle connected at each corner by a small white string. She was stunning; I felt my mouth drop a little as I took in her beauty.

"This is beyond my imagination," I said as she approached and kissed me.

"This old thing," she laughed, "I don't get to wear it much, Skipper. Have you set our course?"

"I've established our course and our destiny, Jill." I said with a dry smile.

"Our destiny? That's kinda deep Skippy," Jill smiled, "what are your intentions this weekend?"

"My intentions are to show you the lake so you will spend another weekend with me, and maybe many more," I confessed, "what are your intentions, counselor?"

"My intentions are to fuck you on every inch of this boat and ensure that you never forget this weekend for the rest of your life," Jill said casually, as she reached across the cockpit and grabbed my beer to take a sip. "Does this thing have an anchor?"

"Ever see a 40-foot boat do 40 knots?" I asked as I throttled up and headed for the secluded cove I had planned for our afternoon.

Jill grabbed my arm and held on as the bow rose out of the water and the twin screws started to howl. We planed quickly and raced across the lake to our afternoon destination. In 20 minutes, we arrived at the secluded cove surrounded by a steep cliff that dropped to the deep waters below.

The bay was deep enough that it wasn't good for fishing, so we wouldn't be bothered by anglers. It was perfect for swimming on a hot day because the deep waters were colder than the rest of the lake. I walked to the bow to ensure the anchor was set, and returned to the cockpit.

"Sailors are sexy," Jill whispered, as she kissed me when I stepped back into the cockpit.

"It's been almost 3 hours since I've had a taste of you," I whispered back, "I'm jonesing that flavor, any chance you can oblige me?"

"Do you want me to sit on your face, Skipper?" Jill asked, smiling, and stroking my cock through my swim trunks, "I have a better idea."

Jill pulled the string on her bathing suit top letting it fall to the deck below. I watched intently as she reached for the sting on her bottoms and started to pull that tiny string as well. She moved very slowly, knowing that I was watching ever single centimeter the string moved. She gave a final tug and her thong bottoms dropped away as well, exposing her tightly cropped pussy. She was now naked in our secluded but public cove.

Jill walked to the stern of the boat, then she turned and looked at me while she sat on the long, padded bench that ran the entire across the entire beam.

"Drop that suit and get on your knees, Skipper," Jill growled as she looked at me with lust in her eyes.

"Yes Ma'am," I said as I quickly dropped my trunks and let my 8-inch cock spring out and cantilever from my loins.

I walked through the cockpit and across the open stern and knelt in front of Jill's spread legs. I couldn't wait to have my face between her thighs again. My mind was vibrating with arousal as I knelt naked, in public, eating my forty-something lawyers pussy for all the world to see.

"That's right, Skipper, it might be your ship, but you're going to answer to me this weekend," Jill laughed in a tone I hadn't heard before.

This was a new side of Jill I hadn't seen before, her reserved side was gone, she was suddenly wild and provocative. I loved it. I licked softly across the folds of her vulva making sure to reach every nook and cranny. She was getting wet as I pleasured her from my knees below.

"Nice work, now a little higher, focus on the man in the boat, sailor," Jill said, quietly, focusing on her own pleasure.

I did as she instructed, taking a long lick from her taint all the way up to the top of her pussy lips and flicking my tongue rapidly and softly across the little nub that was her clit. Jill held my head as I ate her with abandon, I was wild with lust. The heat of the summer day was making me even more excited. I had the entire weekend with this beautiful, adventurous sex goddess, I couldn't believe it.

Jill slid forward on the seat and lifted her legs up over my shoulders, she pushed my head lower, so my tongue slid across her taint and onto her pink pucker. I sank my tongue inside her and buried my face so my tongue could reach its full depth.

"On your back, baby, Mamma wants to ride," Jill ordered, as she stood up pointing to the deck behind me.

I quickly took the position while I watched Jill turn to face across the transom into the bay. She looked over her shoulder and smiled as she lowered that perfect ass onto my face. I was lost in the experience, my rock-hard cock was pointing to the sky and so was my tongue, except it was buried deeply in Jills sphincter.

"I'm in love with your tongue, Mike," Jill moaned, as she slowly rocked on my face, "Is it available for a relationship?"

"Mm Hmm," I muttered from below her while I reached for my cock to give it a few strokes.

Jill slapped my hand away, "Hey, that's mine!" Jill shouted, "don't you dare touch that!"

God, I loved this woman's aggression. I felt I had met my match. While I had never worried about my stamina in the past, I was starting to wonder if I could keep up. Jill leaned forward and took my cock in her mouth. As she leaned forward, she slid back so I could eat her pussy while she sucked me off.

We were naked, in full 69, in public, on a lake, in the middle of the day. We were less than an hour into our voyage and we were already going at it like we hadn't seen each other in a year. I couldn't get enough of her tasty pussy. Her flavor was exquisite, the muskiness was combined with a sweetness that I simply couldn't stop sampling. I wanted to please this woman and make her yearn for another weekend like this. I was becoming desperate for her sex, I didn't just want it, I needed it.

Jill moaned on top of me as she fellated me while I orally satisfied her both front and back. I knew she was close to climax, and I wanted to taste her sweet juices. My cock was ready to explode, I was doing everything I could to keep from orgasming before Jill did. Jill had me all the way down her throat, and she was using her free hand to pull down on my balls, which kept me from blowing my load too soon.

She was spasming on top of me now, her legs starting to shake, I knew that the first wave of her orgasm was washing over her. I stayed focused on her clit while she came. She started to shake more violently as I brought her to full orgasm. Her sweet juices started to fill my mouth and cover my face as she came.

"Oh gawd, Mike, don't stop," Jill moaned, as she pulled off my cock to enjoy her own orgasm.

I stayed focused on her clit, flicking my tongue, and then pulling it into my mouth to suck on the tiny nub that was now fully erect. I was in absolute bliss as this hot mature woman rode my face without hesitation. She acted like she owned me; I was just her sex toy at this point, and I loved it. I slid a finger into her ass while I sucked on her clit, hoping to extend her rapture into another stage. I was hell bent to be Jill's best sex partner -- someone she could never live without.

Jill's orgasm subsided enough for her to dive back down and throat my throbbing cock. I let her clit slip from my mouth and raised my head so I could bury my face in her ass crack. My tongue was now fucking her ass with abandon. I was like a rabid animal, eating her ass while I fucked her throat. I could only imagine the perverted scene that someone would discover if they floated into our sex cove.

"Jill, I'm gonna cum!" I announced, and within seconds, I started to shoot rope after rope of hot semen into Jill's mouth.

Jill stayed down on me, and swallowed everything I gave her. My legs were twitching as she sucked and sucked. Even after my climax had ended, she sucked relentlessly on my cock. No woman had ever done this to me before. She clearly didn't want to stop. I was becoming very sensitive after blowing my load and this woman was acting like we were back at the beginning of the session. Soon, I found myself ready to cum again. For the first time in my life, I shot a second load into Jill's mouth during one long blow job.

I was seeing stars and I felt like my balls had been totally drained. I was ready to take a rest, pour a cocktail, and enjoy the scenery before our next round. But Jill was not in the same mood. She climbed off me, stood up and looked down at me and my spent cock.

"Does the bow have a sundeck?" Jill asked looking down at my 6'4" naked frame, my spent cock resting on my thigh covered in cum and saliva.

"Yes, do you want to sunbath?" I answered with a question.

"No, I wanna fuck," Jill smiled as she reached down and grabbed me by the cock.

"Get up and fuck me, youngster," Jill demanded, pulling on my flaccid cock.

"Meet me on the bow, Skipper, you might need to bring a life preserver," Jill said as she headed to towards the bow completely naked.

I followed Jill's naked form up to the bow and watched as she took her place on the large sundeck cushions that spanned the center of the bow. Being on the bow was a very exposed place to be. It was certain that if a boat went buy, we would be seen and there would be no question what we were doing.

"Jill, we're pretty exposed up here," I said, cautioning my wild lover about the risk of public coitus.

"You're only going to last 2 minutes; then we can go back to the cockpit," she said, smiling at me taking a seat in the middle of the large cushions, "besides, you're already hard again, so you have to fuck me, or you won't be able to put your suit back on."

Skipper Boards First Mate

I crawled between her legs and kissed her pussy and worked my way up to her face. I stopped at her breasts to pay attention to each nipple before I arrived at her neck and then ultimately at her lips. I felt my cock touch the warm folds of her labia, and I was ready to make my entry. I slid forward and entered Jill for the first time on our voyage. At the pace we were going, I knew there would be many more times before we returned to the marina.

Jill grabbed my ass and pulled me in deep, I could sense she wanted to go hard, so that's what I did. I started pounding away with a fast rhythm that bordered on being a little rough. Jill groaned while she kept her hands on my ass letting me know she wanted more.

"That's it youngster, give me that big cock, fuck me hard," Jill moaned as I took full strokes into her pussy.

I was fucking like a man possessed, I didn't even look up at the horizon to see if anyone had discovered our public display of lust. The sun was high in the sky and the heat was almost oppressive. Both of our bodies were covered in sweat as we fucked like animals on the bow of my boat.

"You are so fuckin' hot, Jill," I said, between breaths, "I love being with you."

"Sweet talk me later, big boy, I need you to make me cum. I'm a Pisces, being on water makes me horny."

I didn't say a word, I just focused on giving her what she needed. If she needed hard and fast, she was going to get hard and fast. I was supporting myself on both arms, rising off her body now so I could focus on taking full strokes into her tight pussy. I was going balls deep on every stroke. Our bodies were making slapping sounds that echoed off the cliff that shadowed the bay.

Since I had just cum twice, I was able to last longer, even though I was more aroused than I could remember ever being before. Jill was watching me above her; she kept her eyes locked on mine as if she was trying to read my thoughts.

"You're unbelievable, Mike," she moaned, "I want to push you to your limit."

Jill's words sent me into another gear, I lifter her into my lap and sat back on my haunches. I tossed her up and down my cock like a rag doll. Jill's facial expression told me that she was getting close. I was manhandling Jill like my own personal fuck toy. Lifting her up and then slamming her down on my engorged cock. I could feel my dick rubbing on the top of her vaginal wall, sliding across her g-spot causing her to moan each time I rubbed against it.

Jill had her arms around my neck, holding on for dear life while I fucked her into oblivion. There was nothing romantic happening here, this was a lust fueled fuck-a-thon. I wasn't going to stop until she begged me.

"Fuck me, keep fucking me!" Jill moaned, as I tossed her up and down my shaft.

I watched her eyes and I continued to manhandle her, I saw them close, and her head leaned back.

"Oh gawd!" Jill cried out, as she started to spasm.

I kept lifting her up and dropping her onto my shaft, impaling her with my dick. I had never fucked anyone like this before. I worried that Jill might judge me differently when she finished her orgasm.

Jill was silent while I kept hammering away, she was shaking, almost convulsing in orgasm. I kept going without losing any intensity. I wanted to give Jill the fuck of her life. I looked across the horizon, looking for innocent parties passing by who might be shocked by the perversion happening on the bow of my boat. Suddenly Jill pulled me close.

"Get on your back, I want to ride you," Jill whispered, as we rolled putting her on top.

The view I now had was incredible. Jill's beautiful face surrounded by her dark hair, her tits swinging as she rode my cock for her pleasure, it was stunning.

"God this is good," she moaned as she rode me through another orgasm.

Sweat was dripping off her nose and body onto mine, as it was nearly 100 degrees on our beautiful summer day. Jill was now getting exactly what she wanted as she slid back and forth, rubbing her clit on my pubic bone while my cock filled her all the way to her cervix.

"I love big dicks," Jill said, like I wasn't even there, "this is such good dick."

Jill was in her own world at this point. I was lying on my back just watching the show. My balls started to tell me that they were ready for release. I knew I wasn't going to last much longer. I lifted my head to take Jill's right breast in my mouth.

"Suck my tits, baby," Jill said, "make me cum again."

I moved over to pay equal attention to her left breast as well. I alternated back and forth as Jill rode out another orgasm. The scene was too much for my cock to bear, I knew I was about to cum.

"Jill, you're making me cum, don't stop!" I growled as I started to shoot my third load of the voyage into Jill's womb.

Jill kept riding me, giving herself another orgasm as she milked my cock dry with her tight cunt. I continued to shoot into her for what seemed like a minute. Jill kept riding me as my cock started to deflate slightly. Slowly she reduced her pace until she fell forward on me, both our bodies covered in sweat. Jill laid on top of me for a few minutes and then slowly lifted her head to kiss me.

"Let's go for a swim, baby boy," she laughed, as she climbed off me and walked to the side of the bow.

Jill sprung over the railing and dove into the dark water below. I watched her resurface and then dove in behind her. The water was refreshing, cooling our bodies after our hot sex. I swam to Jill and wrapper her in an embrace, kissing her as I did.