Learning Legaleez Pt. 03

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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 to spend the weekend together.

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Jill and I talked about many subjects over dinner including sex. She was incredibly interesting with a killer sense of humor. I was on my toes the entire time, trying to keep up with her wit and ensure that I was remaining interesting. It was nice to find such a challenging woman; especially when she filled my mind and heart with lust.

We had finished dinner and we were waiting for the check.

"I'm going to skip dessert, I have something waiting for me at home," I said, trying not to sound like a smart ass.

"So, tell me about this ass fetish you seem to have young man," Jill said looking me directly in the eye, "when did you first realize you were a demented pervert?"

"Fantastic leading question, counselor," I laughed, "it's like asking the defendant 'when did you stop beating your wife'."

"Seriously, I'm trying to understand the way you think," Jill continued, "they say our biggest sex organ is between our ears. Well, at least for most people, I think that swinging thing between your legs is bigger than your brain for sure!"

"Ouch," I said, "Talk about a back handed compliment."

"Why don't I tell you all about it back at your place," I proposed, "maybe while I'm enjoying my dessert."

"Check please," Jill said jokingly, while raising her finger.

Jill Invites Mike In

"I don't know about you sport, but I need a shower after you lost control of yourself in my office," Jill said as she entered her upscale home with Mike in tow.

"I would love to join you," Mike said, as he pulled Jill in for a kiss.

"Alright but I've got my eye on you, no funny stuff until we're out," Jill scolded.

I followed Jill into her large master bedroom, and we threw off our clothes and headed for the ensuite bathroom. Jill had a beautiful home, and the bathroom followed the same standard with granite everywhere and Italian tile on the floors. We stepped into the large steam shower with two shower heads and started to rinse off.

I couldn't take my eyes off Jill as she lathered her body and then rinsed. I was becoming obsessed with her figure; it was almost like it attracted me right down to my DNA. Even after our office tryst ninety minutes ago, I had a raging hard on thinking about having her all to myself for the night and maybe even the entire weekend.

"That big cock of yours must get you in a lot of trouble," Jill said with a smile, as she noticed my hard on, "You should think about putting me on retainer."

"It doesn't usually stay cantilevered out like this," I joked, "It must be something in this water."

"Well then, let's get you out of here, that looks painful, I think you need some relief."

Jill left the shower and quickly dried herself off while I was still rinsing off soap and finishing up. By the time I exited the shower, Jill had already left the bathroom which I found kind of odd. I dried off with the towel she left for me and walked into her master bedroom.

Dessert Is Served

When I entered the room, I saw Jill lying on her stomach with her legs suggestively spread looking at me over her shoulder.

"Now what were you saying about dessert," she whispered, licking her lips.

I couldn't believe my eyes. I tried to play it cool so that I didn't leave all my cards on the table in the first few hours of this relationship. Without saying a word, I dropped my towel and walked over to the bed. I lifted her right foot and gave it a kiss as I bent down to climb into the bed. I lied down between her spread legs and started kissing my way up from her calves, keeping my eye on the prize.

Jill watched over her shoulder as I approached her perfect ass. I started kissing the perfectly shaped globes that where her ass cheeks, then I stopped to admire the perfection. As I looked between the cheeks of Jills ass, I could see both her pink openings just waiting for my tongue.

"Are you going to eat it or sing it a song," Jill said, indicating that I was pausing too long.

I buried my face in her ass and slowly licked from the bottom of her crack all the way to the top.

"That's good baby, slowly from bottom to top before you fuck my ass with that tongue," Jill whispered.

I followed Jill's instructions to the letter, slowly licking her crack but pausing at her pink pucker. My breathing was ragged, my hands were shaking, I was totally aroused as I immersed myself in what some might consider a fetish.

"Rub my g-spot while you lick me baby," Jill guided, "I want to cum with your tongue in my ass."

"Mmm," I moaned, as I slid a finger in her wet pussy and quickly found her g-spot as it expanded under my touch.

Jill was getting into my ass worshipping efforts. She was softly moaning between instructions.

"Do you like it, Mike?" Jill asked, "Does it taste good?"

"It's perfect, Jill," I said, breathing quickly with excitement.

"Put your tongue in, put it in deep," Jill begged as she arched her back to open her ass more.

My pointed tongue entered her tight hole, I could feel the rim of her anus gripping my tongue as I entered and continue to go as deep as I could. I continued to stroke Jill's spongy g-spot; I could tell she was getting close. I built up a rhythm as I fucked her ass with my tongue. I was wild with passion and found myself lost in the moment.

"Eat my ass, Mike," Jill moaned urgently, "make me cum with your tongue in my ass."

As Jill orgasmed, I kept fucking her ass with my tongue and stoking her g-spot below. I was now up on my knees as Jill writhed below me in the throes of another orgasm. The site of Jill climaxing with my tongue in her ass pushed me over the edge and I had my own orgasm.

My cock was spraying cum everywhere, but I didn't care, I had never been this aroused in my life. I kept my face in Jill's ass until she slumped on the bed, and I knew her orgasm had passed.

Jill rolled over and she looked at me as I kissed her pussy while looking back at her. I gave her a couple of long licks until she pushed my head away.

"Are you trying to kill me?" Jill laughed, "I need a break, remember old people have fragile hearts."

"I can't help myself, it's just so damn good!" I said in a low voice.

"Did I hear you cum again, by the way?" Jill sat up to take a better look at my cock.

"You did!" Jill laughed, "You little pervert, does my ass do that to you?"

My face was deep red, and I held my hand over my cock trying to hide the cum still dripping from my softening shaft.

"I told you, your ass is my kryptonite," I said, holding my head low feigning shame.

"Let's rinse off and meet back here for round 2," Jill said, "This old lady isn't done with you yet."

As we rinsed in the shower, I hugged Jill from behind, letting my soft cock slide between her ass cheeks. Jill turned and grabbed my cock as she kissed me. She stroked my cock slowly and held my balls with her other hand. Soon, I could feel another hard on growing.

"Nothing sexier than unlimited stamina," Jill said, as she bit her lip," does it ever last for more than 2 minutes."

"You won't be saying that three hours from now when I'm still making your toes curl," I laughed.

Jill turned off the shower and dropped to her knees in front of me. I watched as she slid my cock into her mouth and started giving me a blow job.

Jill paused, looking up at me and said, "I bet you won't last 2 minutes in my mouth."

"Wait!" I said, as she really got serious. This lady knew what she was doing. Her tongue was stroking just under the tip of my cock on the frenulum. She mixed in long strokes taking my 8-inch cock into her throat a little as she did. Her hands were on my balls pulling and stroking them to ensure they weren't forgotten.

"God, Jill, you're fantastic," I groaned as I could feel a third orgasm building in my balls.

Jill moaned at my approval, looking up to read my facial expressions. The idea of having this brilliant woman kneeling naked in front of me sucking my cock had my mind on fire with arousal. I couldn't hold on any longer, she was just too good.

"I'm cumming," I groaned as I tried to brace myself on the shower wall. I was cumming in Jill's mouth for the second time in three hours. The power of my orgasm surprised us both. Jill swallowed what I gave her and held me in her mouth until she knew I was finished.

"That was definitely less than two minutes," she giggled, while she looked up smiling.

"You must think me a complete amateur," I said pulling her up from her kneeling position.

"Maybe I'm just too hot for you," she whispered, as we stood together naked.

I kissed her and groped her perfect ass another time, then I leaned down and sucked on one of her erect nipples. I cupped her full breast in my hand as I sucked and teased her nipple. As I was still on her nipple, I slid my finger into her wet pussy and started to play with her. Jill held my head in her hands as I sucked her tits and finger fucked her in the shower.

"If you insist on this kind of behavior, I suggest we go lie down in bed," Jill said in a low voice.

We dried off and I carried her to the bed, gently setting her down while I laid down next to her.

I continued kissing her neck on my way back down to her shapely tits. My hand was back between Jill's thighs and her nipple was back in my mouth. Jill relaxed on her back, cradling my head in her arms as I worshipped her tits and played with her pussy.

Jill lifted her knees and spread her legs letting me know that I was having an effect. My fingers were inside her, stroking her g-spot again while my thumb brushed across her clit. I was sneaking my ring finger into her ass fueling my own fetish. I fantasized what it would be like to take Jill in her ass, but I didn't want to push my luck too early.

Jill was moaning quietly as I switched from breast to breast. I was carefully sucking and nibbling on her erect nipples and spending time licking her areola. I felt like an hour passed while I quietly made out with her like a high school kid.

"Oh, Mike," Jill moaned quietly, tilting her head back as she started bucking her hips.

Jill reached down and held my hand in place, indicating that she wanted me to continue while she came. Her legs were shaking as she quietly rolled through her orgasm. My cock was back at full length, and I wanted to give her more. I climbed on top of her and started fucking her while she was mid climax.

"Oh God," she moaned as I took deep strokes into her warm pussy.

"Keep fucking me, Mike, don't stop!" Jill exclaimed, "Fuck me all night long, baby."

"That's exactly what I'm going to do," I growled, "I'm going to give it to you non-stop until Sunday evening."

Jill was hanging on for dear life as I continued my epic fucking. Her arms were clinging to my back and her legs were wrapped around my ass. I felt like I was going to last forever since she had already given me 3 orgasms today. I needed to prove to her I was more than a two-minute man.

Warm fluid sprayed against my pubes as I continued my assault.

"You're making me squirt, baby," Jill said breathlessly, "I've never done that, give me it all."

I rolled us over so Jill could take control. Her mouth was open, her eyes were closed, and she had her palms on my chest for support. I was bucking her from underneath while watching her tits bounce. She was rocking on top of me, rubbing her clit on my pubic bone. I watched her have another orgasm as we continued to fuck with her on top.

Jill started riding hard, sliding back and forth over my cock as she did.

"Cum for me while I cum on your big dick," Jill wailed, "cum for me now, Mike."

I grabbed Jill's hips and slid her back and forth, helping her reach her climax. Watching this beautiful woman pleasuring herself on top of me pushed me over the edge and I reached another climax.

"I'm cumming, Jill!" I whispered urgently as I blew my 4th load of the evening deep inside my new lover.

Jill fell forward on me, and I hugged her as our orgasms dissipated.

"You know I don't do this with all my clients right?" Jill laughed quietly with her head still buried in my chest.

"I should get sued more often," I laughed, "are you tired yet? I think I'm getting some blisters down there."

"Should we try actually sleeping together?" Jill asked.

"Great idea, Grandma," I said as I kissed her on the top of her head.

"Oh, you're going to pay for that first thing in the morning," Jill laughed, as she rolled over to get some sleep.

"Thanks for kissing me back, when I kissed you the first time," I whispered, as I rolled on my side to sleep with my new attorney.

To be continued...