Learning Legaleez Pt. 07 - Final

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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 spent Saturday relaxing and having sex all over the boat. Then they dressed for dinner at a lakeside restaurant.

After dinner, the motored to the leeward side of an island to anchor for the night. Once anchored, the spent the evening rolling around below deck.

They've now settled in for the evening and are sleeping as the boat rocks on the shallow waves.

*/

Sunday Morning

I was awakened by the sensation of a warm mouth enveloping my hard cock. I opened my groggy eyes and looked down to see Jill's shiny dark hair on the back of her head as she laid on my stomach while she sucked.

I lied there quietly and watched as this beautiful, intelligent woman took me in her mouth. It was such a turn to watch her head bob up and down on my cock as she worked to bring me to orgasm. There was really nothing like being wakened with a blowjob, it was a true sexual delicacy that I was very much enjoying.

Jill was working my balls in her hand while she slowly took my cock deep into her mouth and then pulled back off and teased the head with her tongue. She was taking her time, almost as if she was still a little sleepy. I looked across the cabin at the clock and saw that it was 7 a.m. I wondered how many times we'd have sex today before we arrived back at the Marina at 4 p.m.

Jill was taking a very slow, relaxed pace as she sucked me, it was driving me crazy with anticipation. I didn't know if she realized how aroused I was getting by her slow stimulation, but I was getting close to exploding in her mouth. She just kept the slow, quiet, blowjob going. I wondered if she even knew that I was now awake because I was quietly watching her and enjoying the selfish pleasure she was delivering.

Without saying a word, I felt my orgasm hit and I started pumping my semen into Jill's waiting mouth. Jill swallowed it all and kept sucking me for another minute or two, ensuring that my orgasm was complete, then she pulled off and laid back on the mattress next to me.

"Good morning, Skipper," she said quietly, "I'm gonna go back to sleep for a bit."

While Jill slept, I walked upstairs and opened the companionway into the cockpit. As soon as I did, I felt the change in temperature. It was clearly going to be another warm day on the water. I stepped out into the cockpit and closed the companionway behind me so the air conditioning wouldn't escape, and Jill could sleep in.

I walked back to the mid-deck refrigerator and pulled out a bottle of iced coffee. I poured myself a glass, and sat in the cockpit, naked, enjoying the early morning sun alone on the lake. After a quick look across the horizon, it was clear that we were the only boat on this part of the lake. The weekend boaters hadn't dropped their boats in yet, and those who kept their boats in the marina, were not yet out on the water.

I listened to the sounds of the lake as I sipped my coffee and pondered our course for the rest of the day. I looked down and saw my still swollen cock from the blowjob Jill just delivered and smiled to myself with abundant satisfaction. I couldn't imagine a more perfect weekend.

It would take about ninety minutes to get back to the Marina from the bay we were currently anchored. I thought it might be nice to sail up to a northern harbor about 8 miles away and I could show Jill some of the stately, historical mansions on the water. I'd talk to her about it when she woke up.

Wherever we went, I wanted to make sure we left ample time for sex. I couldn't get enough of this woman, and I didn't want to waste much of the time we had left without at least a few more sessions making each other orgasm. The heat and humidity was already building even though it was only 8 a.m., I knew it might be as hot as 100 degrees today.

I heard the water pump fire up, indicating that Jill must be in the shower. I sat at the helm sipping my coffee waiting for her to emerge from the cabin below. After a few minutes, the companionway door opened, and Jill stepped up from the cabin below wearing her white swimsuit. She looked absolutely stunning.

Without hesitation, she walked over to me and grabbed my flaccid cock with her left hand.

"C'mon skipper," Jill said, "You're needed back at the stern."

I had no choice but to follow, since Jill was literally dragging me to the back of the boat by my cock. Jill took a seat on the long bench at the stern and then pointed to the deck in front of her. I knew what she wanted, and I dropped to my knees between her beautiful tan legs.

The Skipper is at Your Service

In a swift move, she pulled the tie on the side of her bikini bottoms, pulled them off and set them on the bench beside her. She slid her ass forward on the bench and her freshly showered crotch met my face as I was already leaning in.

"Nothing like watching a big-shot CEO, naked, on his knees at the back of his yacht eating my pussy," Jill moaned, as her fingers combed through my hair.

"This never gets old," Jill continued, as I felt her thighs rest on my shoulders and her legs drape down my back, "I might have you do this all day."

Jill tasted fresh and clean from her shower as I serviced her between her legs. She was more aggressive this morning than she had been on the entire trip. I was very turned on by more demanding side of her. I could feel the raging hard-on growing between my legs. I continued to work my tongue all over her lips and clitoris, enjoying my nautical breakfast.

"Let's just stay anchored here all day, Skipper," Jill said in a low voice, "I want you under my command all day. In fact, consider me your Admiral for the rest of the trip."

"Admiral?" I laughed, looking up across her flat, tan stomach, over her bikini clad tits and at her smiling face.

"Yeah, Admiral," she repeated, "I'm a lawyer, I know something about maritime law. While we're at sea, you take your orders from me."

"Yes, Ma'am," I said, as I put my mouth back on her went folds to continue being of service to my beautiful commander.

"As your Admiral, I order you to stay naked and deliver sexual pleasure to me on demand," Jill moaned as she shifted lower on the bench clearly feeling the effects of my oral stimulation.

"Get on your back, Skipper," Jill instructed, "I'm going to board your vessel."

I did as Jill demanded and laid back on the stern deck. I watched as Jill stood from the bench and removed her bikini top. She took a step and placed her feet on either side of my head. The view below was incredible. I looked up her long legs and I could see it all. Shaved pussy, the orbs of her ass, her perfect tits, and her beautiful face.

"Welcome aboard, Admiral," I said, giving her a goofy salute.

"Oh, shut up and make me cum," she replied, as she mounted my face from above.

Within seconds of mounting my face, Jill was grinding away, using me to get herself off. I didn't mind the impersonal nature of her carnal exploits, in fact, I was wildly turned-on. She was already very wet; her pussy was coating my face in her juices. She had her hands in my hair, and she was moving my head around to deliver maximum pleasure. I just let my tongue hang out and let her put it where she wanted it to go. I could feel my tongue stroking across her labia, and occasionally, she pushed me back across her anus. I was getting properly face fucked by this beautiful woman.

"I'm going to need this mouth of yours all day long," Jill moaned, "do you understand."

I could tell that Jill was getting very close. Her legs were shaking, and her breath was starting to get ragged. I reached up to caress her ass, but she pushed my hands away. It was clear she just wanted to use my face to bring herself to orgasm.

"I'm going to cum in your mouth," Jill moaned, as she slid her pussy and ass across my face.

Things Get Out of Control

I felt the splash of her release onto my face as her orgasm hit. She was squirting as her body spasmed with orgasm. My face and hair were getting soaked with her juices. I was completely under her control, and I loved it. I couldn't believe that I was lying naked, on my back in the middle of the bay, getting face fucked by my 40-year-old lawyer.

"Don't stop baby," Jill said in a louder than expected voice, "I'm still cumming!"

I stayed on my back and let Jill use me as her personal sex toy. My face and hair soaked in her juices.

"Oh God, I want more," she said, standing up and turning around so she was now facing my feet.

"Eat my ass, baby," Jill ordered, "give me that tongue, I want more."

I followed her orders and licked the crack of her ass. I didn't hesitate to stick my tongue as far up her ass as I could. I loved having my face buried between her two perfectly tanned ass cheeks. I was tongue-fucking her ass as if my life depended on it.

"That's right, dirty boy," Jill groaned, "fuck my ass with your tongue."

"I can't believe the big, rich, CEO has his tongue in my ass," she continued, "you'll do anything I want won't you, pervert."

I didn't know what had gotten into her, but I loved this new aggressive side of Jill. I reached down and started jacking myself off while she literally sat on my face forcing my tongue into her pink pucker. I was out of my mind with lust. My balls were starting to tighten, telling me I was close to blowing my load.

"Make me cum again, baby," Jill said softly from her perch on my face, "find the spot deep inside."

Jill's dirty talk pushed me over the edge. I started spraying jets of cum high into the air as I writhed underneath her.

"Yeah, baby, I'm not letting you off this boat until we've emptied your balls," Jill seethed, pressing her ass back against my face.

I shot rope after rope of semen into the air. I felt Jill's hand wrap around my cum covered cock and start stroking.

"You're not done yet, Skipper," Jill laughed, "I'm not going to stop until nothing comes out when you spasm with orgasm."

Jill lifted herself off my face and leaned forward, bracing her torso on the bench in front of me.

"Get up here and fuck me," Jill demanded, "make me cum with that big CEO cock."

I wasted no time getting on my knees behind her and shoving my cock into her wet pussy in doggy style position. I quickly scanned the horizon to ensure we weren't going to be arrested for our indecency. The horizon was clear, it was just a little before 9 a.m. on a Sunday morning. Nobody was on the lake, yet.

I was pounding my cock into Jill from behind like a porn star. Even though I had just blown my load, I was ready to go again. If someone was going to tap out of this fuck-a-thon, it wasn't going to be me.

"Yeah harder, baby," Jill commanded, "pound me with that big dick."

I did what Jill ordered, slamming my loins against her ass, shoving my cock deep into her wet pussy. I watched the globes of her ass ripple as my hips crashed into her with each stroke. She looked over her shoulder at me and smiled. I could tell she was enjoying the full-on fuck she was getting.

"Cum again for me baby," Jill said as she looked in my eyes, "I know you can go again. I want to watch you pull out and cum all over my ass."

I didn't know what the hell happened while she slept, but this woman was not the Jill I went to bed with last night. I felt like I was under the spell of an experienced dominatrix. This was quickly becoming the most incredible sex of my young life. I was all in, hammering my cock deep into Jill's pussy with every stroke.

"I'm cumming," I groaned.

"Pull out, I want to watch you cum on my ass!" Jill commanded.

I did as she ordered and pulled out. I jacked my hard cock and started shooting jets of cum all the way up her back as she watched over her shoulder. I shot 6 or 7 streams of cum before my orgasm subsided. Jill watched the entire time, smiling and laughing as I unloaded.

"Wow!" she exclaimed, "put it back in, did I tell you to stop?"

"You're going to kill me," I said, as I lined my cock up with her pussy and drove myself back in.

Jill immediately started rocking back to take my cock deep inside her. It was as if she wanted to make sure she didn't let me stop fucking her for even a second.

"I've made you cum 3 times, big boy," Jill chided, "maybe you could do your best to make me cum again?"

"Oh, you're going to cum again," I growled, slamming my cock into her starting up another fuck session. I felt my balls slapping her underneath and I hoped that they were slapping her clit. Just to make sure, I reached around and started messaging her little love button while I took deep strokes into her cunt.

"Oh my god," Jill cried out, "don't stop no matter what I say."

I watched her body start to shake and spasm, I knew that she was orgasming.

"Ung, Aww, Mmm," Jill groaned, as I continued fucking her through her orgasm.

After another minute, I felt my balls getting ready to burst again.

"Jill, I'm gonna cum again," I shouted, still taking strokes in and out of her pussy.

"Pull out so I can see you cum," she demanded, "I want to see if you're empty yet."

I pulled out at the last moment and shot a much smaller load all over her beautiful ass. Jill watched as I covered her ass cheeks with only three small jets of cum. She reached back and rubbed my cum all over her ass cheeks. Then she did something I honestly couldn't believe.

She scooped up some of the cum I had shot on her back in her right hand. Then she carried on her fingers down to her ass crack. She watched me watching her lube her ass with the cum from her back. I looked down at her and discovered a devious smile on her face.

"I want you in my ass, Skipper," Jill whispered, looking me straight in the eye, "can you do that for me, or did I wear you out?"

All Limits are Broken

Without saying a word, I stroked my cock as hard as I could make it and lined the head of my cock up with Jill's lubed ass pucker. I looked up to see her watching my expression as she gave me what she knew was my ultimate fantasy. She knew that her ass was perfect, and that I had dreamed about having the chance to take her that way since the moment I saw it naked in her office.

"Do it, baby, fuck my ass," she whispered, "I know you've always wanted to."

I watched as the head of my cock slowly disappeared in Jill's ass. I held myself there, with about an inch of my cock in Jill's ass. I wanted to go slowly to ensure I didn't hurt her.

"That's nice baby," Jill encouraged, "keep going."

I pushed another two inches of my cock into her ass. It was so erotic watching her ass expand around my hard cock. I knew I wasn't going to last long, so I kind of rushed my way in further.

"Easy, Skipper," I heard Jill whisper, "remember that thing is 8 inches long."

"Sorry Jill," I apologized, "I'm not going to last long in your ass."

"Don't rush it," Jill said softly, "I'm going to let you keep doing this until I empty you completely."

"Jesus," was all I could say as I slowly pushed my cock further into her beautiful ass.

My hips were finally up against her ass cheeks; I was all the way in her tight ass.

"God you're tight," I moaned in complete satisfaction.

Jill started to rock a little, stroking my cock inside her ass. I was already on a hair trigger. The mental aspect of having this powerful woman submit to me like this had put me right at the edge.

"Jill, I'm already very close," I whispered to her, "I'm not sure I can hang on."

"Go ahead, baby," Jill encouraged, "cum inside me."

I moaned and spasmed as my cock erupted in Jills ass. Jill moaned along with me as she felt my release inside her.

"Don't stop baby," Jill said, "start stroking me, I want to feel what it's like to get fucked in the ass by your big cock."

"Oh my God," I moaned, as I fell forward on her cum covered back and started taking strokes into her ass.

"That's it baby, I'm yours now," Jill moaned, "nobody else gets that ass but you."

I was able to stay inside her and hold enough of an erection to start stroking. This was now the most epic fuck of my life. I had lost track of how many times I had orgasmed. Jill had taken my semen in every one of her sexual orifices, and we were still going.

I increased my pace, starting to fuck her harder. She looked back over her shoulder to read my facial expressions. She could tell that I was in complete sexual bliss. I had only fucked one other woman in the ass, and she was maybe a 6 or 7, on the scale of 1 to 10. Jill was a bona fide 10 plus.

As my pace increased, I noticed Jill stop watching and let her head hang in front of her. She started to moan louder and louder as I took full strokes into her ass. Her moans were almost guttural in nature. I couldn't tell if I was causing pleasure or pain. My endurance had peaked because I had already cum more times than I could count. I was able to last about as long as I ever had inside of her.

"Oh my God!" Jill shouted, "Harder! Don't Stop! You're making me cum!"

I grabbed her shoulders and started fucking like my life depended on it. Loud slapping sounds filled the stern of the boat. I fucked her like a fiend, without a shred of mercy. We were both going to remember this assfuck for the rest of our lives.

Jill moaned as her head shook back and forth, she was clearly in the throes of orgasm. My cock was still pounding hard and strong when I suddenly felt myself release again deep in her bowels.

"Fuck me until you're empty," Jill moaned in a guttural voice, "I want every drop."

I tried to keep thrusting, but my cock was done. I pulled Jill back on top of me as I fell back on the deck. Then I rolled to the side, carefully setting her on the deck next to me in the warm morning sun. My cock was still in her ass, but it quickly slid out breaking our connection.

"That was unbelievable," I whispered in Jill's ear as she lay next to me.

"If you mention a word of this to anyone, I will sue you out of business," Jill whispered back with a smile.

END OF STORY