Learning Legaleez

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READ THIS SYNOPSIS FIRST!

This is my first mature story. I welcome your comments.

Again, it is loosely based on my experiences with my attorney at the time...

I'm a 27-year-old tech guy in 1999, who left his job to start his own dot com.

Confronted with a legal dispute, I hire a new attorney, Jill Taylor.

I'm instantly smitten by the new attorney and I'm hoping to make this more than a professional relationship.

*/

Legal Emergency

Late that afternoon, there was an incoming call from Jill on my blackberry, and I immediately answered.

"Mike, it's Jill Taylor," Jill said in a serious tone. "I've just received the entire complaint and had time to read it. I hate to ask, but you have time to discuss this yet today?"

"Let's see," I said, looking at my watch, "It's just now 6:00, I could be downtown in about an hour assuming traffic doesn't delay me." I said "Will that work or is that too late?"

"No that will work fine, I've got some work to finish," Jill quickly answered. "When you get here, you'll need to tell security who you're here to meet and they will call me so I can walk you up."

"Alright Jill, see you in an hour," I said, as I packed up my attaché to head out the door.

At 7:35 p.m. I made it to the lobby of the building that housed the Warren and Stern law firm. I told the security guard I was there for Jill then waited for her to escort me up to the 22nd floor. Soon, I was in the elevator with Jill, and we were on our way up to her office.

As we stepped off the elevator, the office was much darker than it was when we met that morning. The sun was low in the sky and the tall buildings around us were blocking much of the evening light. We walked through the dark hallways to Jill's office.

"Are we the only people here?" I asked Jill, "It's only 7:30."

"Well, it is a Friday," Jill laughed a little, "But I guess guys like you work twenty-four by seven."

"Unfortunately, you're not wrong," my voice filled with false self-pity.

"Alright mister all work and no play," Jill chided, "Should we discuss the case?"

"Absolutely," I said, as we both sat where we did this morning.

Jill turned on a small lamp next to her couch so she could better see her notes. The buildings behind her created a wonderful evening view of the skyline. Jill looked just as good as she did this morning, I was happy to be with her again so soon.

Jill and I discussed the legal issues for the better part of an hour, I couldn't believe how quickly the time passed. It was now almost 9 p.m., the evening sky had become blue with darkness. As she collected her notes and rose to walk to her desk, she moved through the shadows to the warm light provided by the lamps on her desk.

I remained in my chair for a moment and stretched.

"This is a great office," I said in a cheerful tone hoping to lighten the subject.

"Why thank you," Jill said, smiling, "It's too bad you didn't get here earlier, you could have said hello to Megan, our receptionist."

"I'm confused, what did Megan want to talk to me about?" I asked, not making a connection.

"Oh, Megan is very sweet, she stopped into my office after you left and asked me if you were single," Jill smirked, "She's about your age and very nice, are you available, Mark? Or should I let her down easily."

I stood to look at Jill. She was leaning against her desk with her hands bracing her body weight. I mimicked her body language and leaned against the chair I had been sitting in.

"There's nobody serious yet, Jill, but I am smitten with someone in my professional life," I said, looking directly into Jill's blue eyes from across the room.

"An office romance, how exciting," Jill said, with a sarcastic smile, "Tell me all about her."

"Actually, I would really like your point of view if you don't mind, do you have a second?" I asked as I took a few steps closer.

"Why not!" Jill answered, "There's nobody in the office here at this hour anyway, and I don't have anywhere else to be. It's not like I'm an old woman who must rush home to feed her cat."

"The woman I have a crush on is a total smoke show and she's scary smart," I said, quietly keeping Jill's eyes in my gaze, "But I'm not sure she likes me."

"What's not to like, you're tall, handsome, and you're worth like forty million bucks on paper," Jill scoffed. "I thought you said she was smart."

"Well, how can I tell if she likes me back?" I asked, sincerely, "I mean it's not like high school, I can't ask her friend to ask her if she likes me. I feel kind of dumb because usually I know these things."

"Well, Mark, I'm older than you, so I've had a few more experiences," Jill explained, "Sometimes you just take a chance and kiss her. If she kisses you back, you know she likes you. If she grabs you by the balls, you know she doesn't; unless she's very kinky."

While Jill was talking, I walked toward her reading her answers carefully. I had already made my mind up that this was happening. I was pretty sure it was going to end well. I had closed the distance with Jill and was now standing in front of her as she leaned against her desk. Jill made no attempt to move, nor did she give me any signal that she didn't want me to move closer.

I leaned in and kissed Jill, she opened her mouth and kissed me back, it was a long, deep kiss that lingered. As we kissed a second time, I felt Jills hand on my cock, she slowly slid her hand up and down my shaft taking the measure of me before her hand went lower and squeezed my balls.

"Oh, this is going to be trouble," I said, smiling at Jill.

"Hey, you started it, Romeo. It's not like I kidnapped you from your cradle," Jill laughed under her breath.

"I'm a baby now, am I?" I said, before I kissed Jill again, grabbing her perfect ass this time.

"Certainly not from the waist down," Jill said, proving to me that she was sizing me up when she groped me.

"I don't feel any panty lines down here, is my lawyer going commando?" I whispered, as I kissed her again while continuing to grope her perfect ass.

Jill turned around facing her desk, I could see the zipper on the back of her black pencil skirt, I dropped to my knees and unzipped her skirt. Jill slid it over her hips and let it fall to the floor around her ankles. Then she bent slightly forward.

I was now face to face with the most perfect ass I'd seen in my life. Jill looked over her shoulder to catch the look in my face as she showed her bare ass to her client.

"Oh fuck, you were going commando," I gasped with ragged breath. "My God, it's perfect."

I pushed my face right into the crease of her ass and started licking, my heart rate was out of control. My fantasy was coming true.

"Hey Jacques Cousteau, it's time to come up before you get the bends," Jill laughed as she pulled on my hair.

"What's with you young guys. Ass is for dessert; you can't just eat it before the main meal," Jill scolded, as she turned to face me. "Now get those clothes off and show me that young stud body I'm charging $800 an hour to glance at from time to time."

I rose to my feet, kicked off my loafers, pulled off my socks, removed my shirt and left them all in a pile on the floor behind me. Then I lowered my slacks and underwear in a single move and stood naked before Jill. My 8" cock was standing tall, up against my stomach, I flexed my abs and arms to improve Jill's view.

"Nope, I changed my mind," Jill said, with a straight face, "I thought you'd be a little bigger."

Before I could react, Jill grabbed my cock and pulled me toward her. We locked in an embrace as we kissed over and over. I undid her blouse and removed her bra to reveal beautiful C-cup breasts that had small triangles over each nipple where Jill's string bikini must rest when she's tanning. This woman was a goddess.

I spent time sucking Jill's nipples as her hand caressed my rock-hard cock. My hands groped her naked ass at the same time. I couldn't get enough. I lowered myself to my knees as Jill sat on her desk. My vision from earlier today was coming true. Jill spread her thighs and lifted them so she could rest them on my shoulders.

"I've been thinking about this all day," I said, as I looked up into Jill's smiling eyes. "This is just perfect."

Jill stroked my hair as she looked back at me, then both of her hands were on my head, and she was pulling me into her spread legs. I could feel her watching me as I started kissing her inner thighs.

"Lick me, Mike," Jill said, "Don't stop until I tell you to, I will help you learn what I like."

Breathless with excitement, I started licking Jill's closely trimmed pussy. Her pubic hair was shaved close with surgical precision to form a tiny landing strip above her clitoris. She was clearly professionally waxed, because everything else was smooth as silk.

Her aroma was intoxicating, I couldn't wait to get my tongue deep inside her opening and taste her completely. I kept my eyes trained on Jill as she watched me worship her with my mouth and tongue. She enjoyed the power she had over me as she gave me instructions how to pleasure her correctly.

"That's it, slowly, bottom to top, yes, stay at the top, now suck my clit into your mouth," Jill whispered her instructions, as I continued to pleasure her.

"Mmmm, you're good, but I will make you better," Jill whispered. "Slower, lighter, all the way down, go in there, go in."

I moaned with lust as she taught me exactly how to eat her pussy. I loved knowing that I was going to bring her to orgasm with my mouth, hopefully more than once. The entire lower half of my face was wet with her juices. I kept watching her watch me eat her, it was such a turn on.

My tongue was as deep as it could go into Jill's pussy, my nose was rubbing against her clit. Jill's hands were stroking the sides of my head as my tongue fucked her wet womanhood.

I slowly slid a finger insider her and traced it along the top wall of her pussy, looking for her g-spot. Jill nodded as I stroked across the area that was starting to swell.

"You're there, youngster, stay on it," Jill whispered, while she watched me intently, "It looks like that tongue of yours isn't very busy."

I leaned in and placed my lips over her swollen clit while I kept stroking her g-spot gently.

"Get me baby," Jill whispered, "Almost there, you're getting me."

My face and chest were flush with arousal as I continued my efforts knowing they were having the desired effect. I had never been this turned on so quickly by any woman.

"Do it baby, make me cum in your mouth, lick me, Mike," Jill whispered, again.

I moaned as Jill held her pussy open to further expose her clit. I'd never been with a woman who was so direct in making sure she got what she wanted. I carefully sucked her clit into my mouth and let my tongue flutter lightly over the head.

As I watched her from below, I could see her eyes were now closed. Jills brownish nipples were fully erect, I reached up to play with them while I sucked her clit. I wanted to bring her to an explosive orgasm.

Suddenly, Jill started to spasm. Her thighs squeezed my head as her ass lifted off her desk, I felt a splash hit my chin as she squirted.

"Don't stop!" Jill begged, as I stayed locked on her clit.

I watched Jill continue to spasm as she laid back on her desk, allowing herself to fully experience her continuing orgasm. I was on fire with passion as I looked up across Jill's flat stomach and ogled her round breasts and extended nipples. I ran my hands over erect nipples trying to create more sensation for my new lawyer that was quickly becoming the best sex partner I'd ever had.

Jill grabbed my hands and held them there while she came in my face again. I lapped up her juices and continued licking all around her open pussy. Jill pulled my hands off her tits and rolled over onto her stomach. With the main course ending, I wanted dessert.

As I moved in to eat her ass, she rolled back over.

"Not yet, moneybags, I've gotta have that cock of yours," Jill said, coyly, "If you want, you can stay with me this weekend and I'll let you have as much dessert as you want."

Standing and grabbing my cock, I rubbed it up and down her soaking wet opening, tapping the head of my cock on her clit.

"I like the way you think, litigator," I said, looking Jill in the eyes, "Would you like me to take the stand?"

"Do you promise to give the whole cock and nothing but the cock," Jill laughed.

"Oh, you're going to get the whole cock, lady," I smirked as I entered her and slid myself deeper.

As I pushed my cock all the way inside her, Jill wrapped her legs around my back and grabbed my ass with both hands. We were locked together, I lifted her off her desk and took her over to the couch. I laid Jill on her back, with me still inside her on top.

I rocked away on top of her, letting my cock slide its full length inside Jills wet sex. I was already very close to orgasm after having my fantasy come true on her desk.

"You're too much for me Jill," I'm not going to last, I said softly, almost apologizing.

"You have to cum in my mouth," Jill demanded, "We can't make a mess in here."

"Oh my God, Jill," I said, pulling out and getting up off the couch.

Jill dropped to her knees and took me deeply into her mouth. I instantly went off, emptying what seemed like a year's worth of cum down her throat. Jill stayed on my throbbing cock until she was certain that my orgasm was over.

"I'm sorry, Jill," I said in an apologetic tone.

"Hey, no need to apologize, I had three orgasms before we started fucking, you did fine," Jill said cheerfully.

"Besides, all I have to do is let you eat my ass, and you'll be hard again in a few minutes," Jill laughed.

"Your ass is my kryptonite," I laughed, "I lose all my strength when I'm around it."

"Well listen, I'd like to stick around and do this all night, but I'm hungry," Jill said, as she started collecting her clothes.

"Why don't you take me to dinner and then spend the weekend with me," Jill propositioned, "You can teach me about the internet, and I can teach you a thing or two about sex."

"What's the internet?" I said with a smirk, "I think your fucked me senseless."

"Wait until I get done with you this weekend, that is if you can keep up with me," Jill laughed.

"Now, grab your clothes, you have to get dressed and buy me dinner before my legal fees bankrupt you," Jill bantered.

I got dressed and headed out with Jill, I guess we were going to have dinner and then spend the weekend together. I was already trying to keep up.

To be continued...