The Business Woman and the Lawyer
by mattwatt
Copyright© 2012 by mattwatt
Romantic Sex Story: It began when the two of them agreed to run a local food bank. Each slow step along the way was exciting for them: the business woman and the lawyer.
Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa Spanking Interracial Black Female White Male Oral Sex Anal Sex .
He'd gotten all of his necessary work straightened out and was about twenty minutes early for the Board meeting, where he'd be introduced as the new co- director of the local food bank. It was a cooperative venture that was supported by most of the local churches, as well as some of the government entities.
He also knew, in advance, that his appointment wouldn't be the only announcement that they'd be making that day. He'd discovered almost by accident that they were also appointing a co-director to help him with the job. Her name was Lily Jefferson, a local business woman, and if her reputation was to be believed, quite a successful one.
He met Lily Jefferson in advance only because she called him on the phone and introduced herself to him. He suggested that they meet for a cup of coffee.
"What's your schedule," she asked.
"Oh, I'm flexible today," he said. "Have everything, for once, in order and no extra demands."
"Must be nice!" she said with a twinkle in her voice.
They made arrangements to meet at a local coffee house and get to know each other.
Clifford Aimes was a lawyer, and very successful in his profession. But he was at that point in his life, when he was looking farther ahead, both in terms of his personal life and in terms of his professional life.
After all, he'd been captive, as he thought of it, to the law since he could remember, and during the span of his career thus far, he'd about done it all. He'd spent some time as a public defender; he'd spent some time as a public prosecutor, and was the criminal trial expert at a major law firm. Right out of law school, he partnered with a friend to establish a law firm. It had grown and was a very successful one.
At his 'ripe old age' of 48 it didn't seem to be enough for him anymore. So he was backing off a little from some of the many, many demands of the practice. Of course that was only part of his thinking. Clifford Aimes was really a lonely man. It was like waking up one day, he thought, and realizing that you've taken time for nothing but your one thing: law.
Certainly, it had made him fairly well off, if not down right wealthy but apart from that it hadn't given him the answer to the way he was feeling at his present age.
It was this combination of impetuses, thoughts that got him involved initially in the running of the local food bank. He was first invited to be on the Board of Directors by a friend. He enjoyed doing it, meeting new people and did it for a while. After that, when the current director tendered his resignation, he decided to take some of his free time and do the job himself. He'd certainly made his decision to back off from practice a bit, becoming more of a mentor there, and the food bank seemed to fit in nicely with his new found determination about his life.
It was actually 'co-director' that he became. It was moreover a job with a stipend attached but Clifford simply indicated that he'd rather that the stipend be used for operating costs at the food bank.
He was also impressed with Lily Jefferson, when they met for coffee. He didn't really know what he had expected Lily Jefferson to be like but was surprised at her.
She turned out to be a rather good looking afro-american woman of, as far as Clifford could tell, indeterminate age--(truthfully 33 years). She was fairly tall, at 5'11" in flat shoes, wore her hair cut close to her scalp and though she possessed the legs and butt of a runner, an athlete, was also heavily developed across the breast.
These were the thoughts that went parading across Clifford's mind, as he finally had a chance to meet Lily, at the coffee place. The initial impression left him, at first, a bit speechless.
He stood as she came to his table, apparently able to pick him out of the crowd. She had a kind of amused look on her face, as she said:
"Clifford Aimes, it must be!"
He hesitated a bit, struggling out of the surprise of his initial impression.
"Clifford?" she asked again.
"Sorry," he said, "I'm just surprised by you and I don't even know why."
"But you are Clifford!" she said.
"Guilty!" he said standing and taking the hand that she offered.
"You're looking at me as though you were thinking 'statuesque'!" she said with a broad grin.
Clifford appreciated her immediate humor and answered quickly, with more honesty than he might have used, had he thought much first:
"I was really thinking more like 'beautiful'!" a bit flustered.
She smiled at him and said: "Well, your honesty and gentlemanly response certainly stopped me there!"
"Oops," he said, "Sorry."
"Don't you dare say it!" she quipped at him and sat.
They sat to coffee and really became almost fast friends right away.They spoke to one another about their respective backgrounds. Lily indicated that she had heard of Clifford and his reputation as a lawyer, especially trial lawyer in various circles.
"Yes," he responded, "It was for the longest time all that I did; it was kind of all that I've been. I'm trying to change that a bit."
Then she spoke about her life in business, and the struggle to get to the top, where she currently was. She expressed similar kinds of thoughts about the need to 'branch out' and become almost a different kind of person, one more well rounded.
Their talk took them a while, and Clifford was surprised at how comfortable he felt with her. That wasn't a usual response for him to women. He simply tended to be a reserved kind of individual.
He was also open enough with her that he told her that. Her answer was a kind of tinkling laugh.
"I've got you under my spell!" she said.
"Oh is that it!" he replied, "I knew it was something."
"Business?" she asked softly then.
"Sorry, business it is!" he said.
"You need to stop saying that word," she said, "You're such a treat Clifford and I'm not being fair to you. I'll stop my teasing!"
"Please don't," he said, "I've been so stuffy for so long that the teasing will do me good."
"Teasing it is then!" she said with that award winning laugh again. "And, yes, business."
They talked then about the up-coming task that they were taking on, neither of them having had any real experience at it, and they found quickly that they were able to share ideas and seemed to settle into a rather good working relationship.
After a while, he excused himself and said that he had to get home:
"Wifey will worry?" she said, grinning.
"No," he said simply, "She's been dead for almost ten years."
"Oh," she said, "How stupid of me to make such a remark!"
"Not at all!" he said, "You have no way of knowing. She was flighty, raised by very, very strict parents who left her always feeling inadequate and took her own life in a rash moment."
He stopped then and said: "Now I guess it's my turn to apologize for running on."
She put her hand over his and said: "No, really, but please accept my sympathy."
He smiled and said: "Thank you, such expressions are always well received. But the truth is that I have to get home to Churchill and Roosevelt. They'll be upset with me."
"Churchill and Roosevelt?" she asked, eyes going toward the ceiling.
"The two siamese cats who run my life!" he said.
She cooed: "Oh, I love cats! It's against the lease agreement at the apartment building where I live!"
"You'll have to meet them someday!" he said.
"Oh, I'd love that!" was her answer.
"I really do have to go, though I'd love to invite you to dinner," he said.
"Consider my answer 'yes' and we'll make it another time soon. The great men await you at home," she said with a smile.
"You must think me odd at least," he said with a bit of shame, "To be bound like this to two animals."
"I think you down right dear to be so concerned about them," was her reply. "And I insist on this."
With that, she went to him and pulled him into a substantial hug. It sent a jolt through him and he found himself terribly pleased by it. He ended smiling and gave her a cheek kiss just before leaving her, getting a beautiful grin from her.
They parted, after their brief meeting, as true friends.
The initial meeting, how successful it went and how comfortable it was, was certainly on both of their minds, as they left one another.
Clifford took time that evening to talk to Churchill and Roosevelt about this dynamic woman that he'd met and would be working with.
"She's black," he said to the two of them and hesitated, "I don't know if you say 'black' anymore or 'aftro-american' but she's gorgeous. So, what do I do?"
He was having a late night glass of white wine, as he talked to them. They sat next to him on his couch.
It was Churchill who made the first noise and Clifford shook his head, saying: "Yes, Mr Churchill, I agree, I will just let what happens happen! Thank you for your advice."
Roosevelt chimed in at that point and seemed to be agreeing with the conversation.
Lily, at home that evening, gave herself, during the luxury of a deep bath, time to think about their meeting. She was positively tingly about how it had gone. She too was drinking white wine.
"You just be careful, girl!" she said to herself. The answer that she gave herself was: "But two siamese cats! He can't be all bad!"
She giggled into her wine then and continued her answer: "No, he seemed to be pretty much good!"
Their work/partnership at the agency seemed blessed from the beginning. They dealt with the tension between them, which seemed to be pretty much in the air, when they were together, and they worked well together.
For Clifford it was such a totally different kind of situation than his law practice that it was a treat for him in a number of ways, not the least of which was working closely with Lily, whom, even if he didn't admit to his attraction right away, he came to appreciate for her ability and insights more and more as they worked together through their first month.
But gradually that initial kind of attraction made itself felt, and became a part of their relating. In dealing with his own feelings, Clifford never followed up on his intention to take her to dinner. Their time together, learning how to do what they were doing essentially, was that busy and the possibility never came up again or at least was never mentioned by them.
It was then also that something happened that produced a kind of bond between them.
It was the end of the day, and the end of the month, a busy time at the food bank. They had finally gotten the last of their clients satisfied and were just finishing up some book work.
"Busy day," he said with a small grin.
"Was that," she said, giving him a hug. (Lily was a hugger!)
"Thanks for everything!" he said, and they both realized then that he meant it in a much broader sense than just 'thanks for help here at the food bank'.
Lily smiled a 'you're welcome' and said: "Cliff, I'm meeting some friends for a drink in a bit; care to join us?"
He smiled: "I'd enjoy that! Thank you."
They drove separately but went into the pub, where she indicated the friends would be, together. She introduced him to the group, a mixed group racially, and all apparently friends, and they all indicated that they were happy to meet him and had heard from her about him.
One of them a younger guy named Ray, actually about the youngest one in the group, was a bit different:
"So," he piped up, "Lily brought 'the man'!"
He laughed at his own humor though Lily said: "Say, what, Ray?"
He said it again and then proceeded to continue to make such remarks at Clifford's expense. The initial amount of laughter that had greeted Ray's attempts, half hearted though it was, faded quickly, as Ray continued to needle Clifford. At first, Clifford chose to ignore him but that only prompted the immature bully in Ray, who continued to make his cutting remarks and little jokes.
It was then that Clifford decided that he'd had enough:
"Look, Ray," he said, "I deal in my professional life with all sorts of cretins, fools, half wits and low lifes and I have no intention of spending any of my leisure time with another."
Ray looked shocked and there was a profound silence at the table. Clifford turned then to Lily and said: "Lily, I apologize for speaking that way to someone you consider a friend but I'm leaving now. Thank you for asking me to join you and your friends."
He got up, nodded at the group and began to walk away. Just then Ray came up with a parting shot. It caused Clifford to hesitate and look back just long enough to see Lily get up from her chair and slap Ray's face and stalk away from the table, going in Clifford's direction.
When she got to where Clifford was waiting, she said through clenched teeth: "Please take me out! I will not let that little shit see me cry!"
He smiled at her as though there was no problem at all; gave her his arm and walked out with her.
It was only, when they were finally outside that she gave into the tears that were threatening to come all along.
He held onto her as she sobbed and made her apologies to him about the way that Ray had needled him.
"How long has he been in love with you?" Clifford asked, kind of shocking her.
"In love?" she asked.
"Yes, obviously!" he said.
"Ohh," was her reply, "I never considered it. Thank you for helping me!"
He smiled at her: "Would you consider dinner? I make a very good omelette!"
"Oh, how nice!" she said.
"Roosevelt and Churchill are dying to meet you."
"Oh, yes," she sighed, "The great men!"
"The very same!" he said to her.
They had a quiet and friendly dinner that night. She was simply in love immediately with Churchill and Roosevelt. They were blue point siamese and were very affectionate. They ended up having a very nice dinner. She complimented him on his prowess as a cook and then helped with the clean up. Then afterwards they watched an old tv movie, where she sat with Roosevelt in her lap and Churchill on the couch between them.
"I love them, love them!" she said fervently.
"Well," he answered, "They seem to be of the same mind."
Before she left, she apologized once again for the ill manners of Ray.
"Don't let there be trouble on my account please!" he said.
She looked at him and said softly: "You are such a kind and considerate man."
Then she thought a bit and said: "And there is no 'him' to cause trouble."
"Oh," he said, "Good to hear."
"You okay to get home?" he asked.
"Yep," she said, "Not too drunk, at least not on the wine and if I end up in the slammer or drunk tank, I know a good lawyer."
"That you do!" he said.
"But one thing," she said then.
She went to him for a hug.
Clifford got simply, totally, quickly and completely lost in the feel of her hugged against him. He was reluctant to let her go but wasn't completely sure that they were ready for the kiss.
"You feel so nice" he said, when they broke apart.
"Oh, yes!" she said. "Need to go home and think about that!"
"Yes," he admitted, "Churchill and Roosevelt and I will need to have a talk."
She gave him her tinkling laugh as she walked to her car, waving to him, as she got into the driver's seat.
He stared at her until she was gone.
Lily had just settled into bed, when her phone rang.
"Hello," she said.
"It's me, Clifford," he said.
"Hi!" was her enthusiastic answer.
"I"m so ashamed that I didn't see you home," he said.
"Well, aren't you the lovely, thoughtful one!" she said in response.
There was a silence then and she giggled as she went on: "Bet you just wanted to see me in my jammies!"
He laughed. "Hadn't entered my mind but it is there now and I won't get any sleep!"
She laughed in return and said: "Got you there! I don't wear them!"
"Oh," he groaned. "I'd better say 'good night'."
"Good night, Clifford," she said. "See you at the food bank."
"Yes, at the food bank."
It was a kind of sleepless night for each of them.
Their relationship was well established, and getting better, after the evening of drinks and dinner at his place, and especially after the spectacular hug! She sent him a 'thank you' note, which told him that she loved his beautiful home and was absolutely enamored of his siamese cats.
It certainly gave him something more to think about.
The next step forward in their relationship came a few weeks later. There had been a meeting of the small staff that helped run the food bank, and Clifford was in the office afterwards. Lily came in before going home.
(In the background of what was about to happen was the never faced issue of Lily's collapse into his arms after the debacle with Ray. It impressed her a great deal at the time that Clifford apologized for his behavior and how that behavior must have looked to her. The brief moments of him holding her and consoling her, for what was, to her, a debacle involving her true joy at him being introduced to friends, was never far from her mind. It was one of the reasons that she dressed the way that she did that night for the bit of work that they had to do for the food bank. The rest: that is, the way she acted, was pure chutzpah on her part! Certainly a desire to move their relationship to another kind of level. And since this was the case, she succeeded beyond her wildest designs!)
He looked at her and smiled and said: "You look smashing tonight!"
She was wearing a black cable knit sweater and a pair of very, very tight red capri style pants.
"You like?" she asked with a grin, twirling around for him to look.
He caught the kind of devil may care attitude that she was showing and joined in by asking:
"But tell me, what's the darker black line in your sweater?"
(Stupid question, you think? He admitted as much and was never sure of why he asked precisely that question but was eternally grateful for the result!)
Her eyes twinkled and, as though he'd thrown down a gauntlet for her. She was, if anything, ready for him that night: she grabbed the bottom of her black sweater and pulled it up to her shoulders and said, rather proudly:
"It's my bra!"
He was smitten, 'gob smacked' the English might say, immediately by her showing him her black bra. It seemed to have a profound effect on her and she continued. She turned so that her back was to him and unzipped her red capri pants just a little, enough to show him the waist band of her panty hose and the beginning of her butt crack.
"And no panties!" she said rather proudly.
He stared at her at first for a bit, noting her wide grin and then made his own decision. Without another word, he got up and was kissing her.
"Oh, yes," she groaned into his lips.
Clifford very quickly got lost in the feel of her lips on his, and then the feel of her tongue licking at his lips.
"Wow!" he said.
"Wow, I guess!" was her answer.
He looked at her and kissed her again, and said: "Okay, here's what I want you to do!"
He gave her instructions then, with a plan forming in his mind all the while:
"Go into the ladies' room," he began. "When you're there, first, take off your sweater and then take off your bra. Then take off your pants and then take off your panty hose. When you've done all of that, then put your sweater back on and your pants back on. Bring me the bra and the panty hose."
It was a flat out challenge. Lily recognized it as such, and she was ready for it. All of her personal messages, to and for herself, since the debacle with Ray, that had affected her so much at the time, coalesced at that point, when he was 'telling her what to do.'
In fact, Lily Jefferson was ready for Clifford Aimes right then and there.
She smiled at him and replied by 'reading back' the instructions: "Okay, I go into the ladies'; when there, first, I take off my sweater and then take off my bra, setting it aside. Then I take off my capri's and then take off my pantyhose, setting them aside, and, when I've done that, I put my sweater and capris back on and I come back here to give you my bra and my pantyhose, though I think you'll look funny in them!"
She ended this by giggling and he said to her, with mock severity: "Just go and do what you've been told, exactly the way you've been told."
"Yes, sir," she said with mock obedience and a formal salute.
She went off then to the ladies room, shooting him a great grin over her shoulder and adding an air kiss to the grin.
As soon as she was gone and had disappeared into the ladies' room, he followed and stood outside of the ladies' bathroom door, kind of talking to himself and judging the time sequence for what was happening within. He even made some rudimentary movements to suggest what she might be doing inside of the bathroom.
Finally, he was ready. He slowly and silently opened the bathroom door. He saw her immediately. His timing had, indeed, been perfect. There she stood, just that moment folding the pantyhose and putting them on the bathroom counter. She was totally naked.
She looked up, saw him and made a shocked noise, putting her hand to her mouth in surprise.
He took in the sight first: she was gorgeous, beyond anything that he'd imagined or even hoped. The darkness of her skin was silky and entrancing. Her breasts were indeed large, with correspondingly large, dark, dark brown nipples that were wide and puffed up, as though with desire. Her stomach was a flat plane that led down to the beauty of her curly pubic hair that was bold and luxurious. In the mirror he could see the slopes of her butt cheeks, whose roundness promised a firmness that was beauty itself.
It took a second then to make a comment: "My god, beautiful beyond belief!" he said.
"Ohhhh," she sighed but was shocked by what he did next.
He stepped over and swept up the clothes that she'd put on the bathroom counter, and taking all of her clothes, walked out of the ladies' bathroom, leaving her there naked, and giving her a sly smile, as he went to the door of the ladies'.
Just before he let the door close behind him, he turned and said again: "Beautiful beyond belief!"
The last echo of a word that he heard from her was soft spoken: "Thank you," as he left the ladies' room totally.
He went to his office and waited for her.
She appeared after a very few minutes, which she used to get herself settled and breathing right again. By the time she was at the door of his office, she was, she felt, ready for whatever this entrancing man had in mind. She already made that decision.
He watched the doorway until she actually appeared. She leaned against the doorway on her elbow, her head supported by her hand.
"Pleased that your little scheme worked, white boy?" she asked.
He gave her a huge uncharacteristic grin and said: "Yep!"
She giggled in reply.
"Gonna play?" she asked.
"Yep!" he said again.
"Verbose!" she charged, giggling.
"Yep!" he said a third time.
"How long since you've played?" she wanted to know, turning earnest for a few seconds.
A kind of wind of almost pain passed his face: "Oh, a long, long time," he began to talk about it again: "She--wife--was flighty, depressed by a bad overly strict childhood. She never came truly out of it, thanks to her shitty parents. She committed suicide and life became, after that, work and almost nothing more ... except Churchill and Roosevelt."
"Ah, yes," she said, "Churchill and Roosevelt, the world's greatest cats."
He sighed and she was across the room in a few seconds. She held his head against her stomach and ran her hands through his hair.
"Wonderful man! Wonderful man! Wonderful man!" she cooed to him. "We don't have to play, if it's too painful!"
He looked up at her, regarding her slowly and said, with a faint smile: "But I have a plan!"
"I'm sure that you do!" she said, laughing, "And I want to know what it is! But maybe I can help a bit here."
"How?" he asked.
"Watch!" she said and she strode across the room, looking back at him just before disappearing into the hallway. He followed her.
She waited until he was in the hallway too and knew that he was watching. Then she strode down the lighted hallway, a long one, with her ass cheeks wiggling back and forth.
"Ohhhhhh!" he sighed as he watched, and she threw him a smiling glance over her shoulder.
She turned at the end of the hallway and strode back to him, her large breasts, nipples engorged, swaying back and forth. He was captured.
When she got to where he was, they kissed. It was a pure and simple declaration of passion and more for them.
"Plan?" she asked pleasantly.
He kind of gulped and said: "I'm going to spank you!"
She hooted!
"You really are brave!" she crowed. "I love it! Tell me why!"
"You didn't wear any panties and I love panties!" he said simply.
"Of course," she said, "You're exactly right! Where?"
"Here! Now!" he said forcefully.
She thought for a moment and said: "Today, your way; next time is mine!"
"Granted!" he said in agreement.
He was a bit taken aback by her apparent quick acceptance of what he wanted.
He took her by the hand and led her across the room to where a straight chair was. He sat and she grinned down at him, and then draped herself across his lap, her large, lovely, round ass staring him in the face.
The first thing that he did was to lower his face, and, while she was watching, plant kisses on her up-turned, naked ass.
And then he spanked her!
She fussed but he made sure that it wasn't hard or long. But it certainly had both of them turned on. She eventually slid to her knees and had his bursting erection out in no time, and was sucking on him.
"Mmmmmmmmmmm!" he cooed and leaned his head back. "Love those lips! Love those tits! Love those nipples! Love your ass! Love your pussy bush!" he said, almost babbling.
"Got you, white boy!" she said.
"Oh, you do!" he agreed, just as he began to cum in her mouth. Finally, straining, he rasped: "Gonna..."
"Yes,"' she said quickly and fastened her lips more tightly on his erection, not letting him go, even when he began to spurt and fill her mouth and throat with it.
She grinned up at him, all the while she sucked him until he was totally finished and cleaned off.
She leaned back on her heels then and said: "Need time to think about this now!"
"Yes," he agreed.
"Tomorrow!" she said, "After thinking?"
"Yes," he said, "Then we talk."
He watched carefully as she dressed again.
They kissed before she left, the kisses long and lingering and she said: "I heard you, you know."
"Yes," was his only comment besides another kiss before she left.
He sat there a bit then, before going home.
"Wow!" he said to himself, the dark and the cosmos.
It was late and he had already drifted off to sleep, when the phone woke him.
"Hello," he said.
Her voice, sounding soft, husky-sexy, drawled: "May I please speak to Roosevelt or Churchill?"
He chuckled and answered: "Miss Churchill and Mr Roosevelt have retired for the night and are not to be disturbed, at their own request."
"Drat!" she said.
"My your voice sounds sexy, kind of husky over the phone," he said then.
"Oh," she replied and then she jumped into the conversation that she wanted to have:
"Oh, Clifford, talk to me! This has me in such a swirl; I don't know what to do!"
There was a silence of a few seconds and she went on: "Do you do those kinds of things to people, women often? I mean taking the clothes and spanking."
"Almost never," he admitted, "Except today. Seemed like a good idea."
"I am so swept away here," she said next, "I mean, I just haven't been into physical things that much, not for ages and ages. It seemed fine, no problem for me. I had my work and it's been so successful, enough that I hardly have to work these days at all, and then this! This!" she sighed then.
"You told me what to do and I did it! I'm not very submissive," she reasoned, "Not really but I did it and then you showed up and took my clothes with you and I was dumb founded! AND you spanked me! That's never happened; I mean never!"
"Do I need to apologize?" he asked softly.
"My god no!" she said vehemently, "It was the hottest thing that has ever happened or that I could ever imagine!"
"Good!" he chuckled.
"And now ... now I want it all again; I can't believe that I'm on the phone at 1:30 AM telling a man, you, that I loved being spanked and want it to happen again."
She paused and he let her: "Oh, Clifford, I want it all again and it kind of scares me, and flusters me and all. I'm giggling too! Damn it! I don't giggle."
"Yes, you do!" he said, chuckling himself.
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