Ms. LeGrand's Favorite Pt. 03

Todd enjoyed his early days in New York City. It was exciting to be in the heart of such a busy metropolis. The huge crowds of people on the streets on in subway, the wild diversity of culture, the intelligence and attitude of the people he met...it was a long way from Iowa. He found himself a little apartment in Astoria, but he really didn't spend much time there. He put in long hours in his new office -- coming in at 7 or 8 AM, leaving at 8 or 9 PM, with a break to go to the gym (Ms. LeGrand encouraged it), but mostly eating lunch at his desk.

He became close to his fellow assistants Alex and Reece, bonding through their service to Ms. LeGrand and their mutual resentment of Tucker. Todd quickly gained a reputation for hard work and for a slavish devotion to Ms. LeGrand. They would all smile at each other when one would come back from her office rubbing his ass. (Ms. LeGrand believed in "maintenance spankings.")

Todd became a loyal and capable subordinate, learning to anticipate her needs, and doing his work thoroughly. At first, Ms. LeGrand mostly asked him to rub her back and feet. But soon he was stripping and masturbating at her command. Then Ms. LeGrand began calling him in for an "oral briefing," apparently a sign that she was taking a shine to a boy. She would raise her skirt and lean back in her chair. Todd would then kneel before her and pull down her panties. He would push his face deep into her pussy and would tongue-fuck her or suck her clit, depending on her mood. Sometimes he would slide in a finger. He grew proud of her skills of anticipating what would please her and then giving it to her. Before long, her body would start shaking and her hand would push him deeper into her crotch. Her cunt had become his entire world, all he could smell, taste, feel. Finally, she would start moaning and rode his face to one climax after another. When it was over, and she told him to be on his way, Todd wouldn't bother cleaning his face. He wanted the other boys to see what he had done.

Todd realized that his initial observation that LeGrand-Rice was a female-dominant workplace was correct.

Women held almost all the powerful jobs, while most of the men were young and in supporting roles. The executives were constantly joking that the "boys" were hired more for their good looks than for their competence. They felt free to exchange sexist jokes, grab the boys' asses, and engage in crude come-ons ("Mama's clit won't lick itself!") There were salacious competitions among the women over who could bag the most interns, with extra points for scoring a virgin. If a young man wanted to get ahead there, he knew that he had to "give Mama what she wants."

On Friday nights, "the gals" would throw little parties to blow off steam from the week. "Boys" who showed up were often told to "whip it out" so they could be "inspected." As the women got drunker, the young men were told to strip or even to jerk off while they watched. Some of the less experienced boys got pretty drunk easily and would wake up somewhere completely new to them.

Nobody exemplified this "bad girl" culture more than Sarah Walker. Tall, blonde, oozing self-confidence, Sarah demanded attention wherever she went. She was hailed as a "genius," second only to Ms. LeGrand in her talent, which meant that her misbehavior was always excused. If other women talked about their sexual adventures, Sarah would discuss her periods in graphic detail. If other women let their farts rip, she required her male subordinates to accompany her into the washroom. If other women grabbed their boys' asses, Sarah liked to spank them. (And not the tender discipline Ms. LeGrand would dish out. Sarah liked to hear them cry). She would whip out her smartphone and show off pictures of their cocks and reddened asses. Sarah once sexually harassed a gay male employee until he finally gave in and fucked her. She then told the whole office what a hot experience it was for her. Everyone knows that a gay man just needs some good pussy to change teams, right? Boys who spent the night with "Aunt Sarah" were never willing to talk about the experience. But sometimes welts were visible on their backs when they were changing in the gym locker room.

Ms. LeGrand was much too self-controlled to engage in such behavior, and to some extent, her personal assistants enjoyed her protection. She was not above, however, "lending" them out to executives who had performed especially well.

In September, Todd was informed that, for the first time, he would be accompanying Ms. LeGrand on a trip. She was meeting with a big client in the tech world, trying to persuade them to renew. Todd spent several days working on the presentations Ms. LeGrand would make and researching how LeGrand-Rice had helped the client succeed. She told him she was very pleased with his work.

He met Ms. LeGrand at Kennedy Airport early on a Monday morning. She was gracious and professional. She was dressed casually for her, in a matching black blazer and trousers, with a long-sleeve magenta blouse. The two of them went through security and walked to the gate. As they walked, she chatted about the trip. They were staying in one of San Francisco's most high-end hotels, overlooking Union Square. In the morning, they would be making their presentation in one of the hotel's meeting rooms. She was pleased by his hard work on the presentation, but he had to understand that she would be giving it, and that he was not to speak.

Not only had Todd never flown cross-country before, he had certainly never been in first class. He and Ms. LeGrand each had a complimentary class of wine, but she made clear he was not there to get drunk, and they spent most of their time reviewing their presentation. He occasionally started out the window to watch America go by.

Ms. LeGrand teased him, "This is your first time? I'll be gentle with you."

After they arrived in San Francisco, they were met in baggage claim by a limo driver. When they reached the hotel, Todd could not hide how awestruck he felt gazing at the lobby. Once they reached the suite, he was even more beside himself.

They had dinner at a chic restaurant a few blocks away from the hotel. Afterwards, she broke the news to them. They had to get a good night's rest, so no fun for now. He would sleep on a rollaway and she would sleep in the king-size bed. But she promised they would enjoy themselves after the meeting.

The next morning, they met with the executives from the Silicon Valley firm. Her presentation was a triumph, explaining how LeGrand-Rice's consulting had increased their profits. She went on to lay out their vision for the firm's next five years. Whenever one of the executives asked a question, she responded in a firm, confident tone. No one dared challenge her. Todd sat by her, remaining silent as instructed, but passing her the material she needed.

After lunch, they returned to their suite. Almost as soon as they arrived, Ms. LeGrand's phone went off.

She answered her phone. "Yes. Thank you. I look forward to working with you in the future. I'm glad you are happy with our work."

"That was our client. Our contract is being renewed. We've done fine work for them, but also these Silicon Valley boys spend all day with other boys. Which means that a powerful woman can wrap them around her little finger." She smiled and laughed.

"Mr. Stevens, please remove your clothes. All of them."

"Victory spanking."

Ms. LeGrand sat on the couch.

"Get across my lap, boy."

Todd meekly complied.

"I have my own way of celebrating a victory like today's. I hope you enjoy it, too."

Todd knew what was coming. He felt her hand slap his buttocks, again and again. He counted each one until he reached 20. When she was finished, Todd's ass was feeling a familiar burn. "There, there, my beautiful boy. Sit down next to me."

Todd wasn't feeling much like sitting. But he obeyed Ms. LeGrand's command. She stroked his bare shoulders, and then kissed him. This was the first time she had done this and he could tell why she had waited to bestow it as a reward. Her warm lips met his. Their tongues soon intertwined. Their desires for one another raged like a blazing fire.

After a few minutes, Ms. LeGrand broke off the kissing and told him her feet were tired. Todd knew exactly what to do. He fell to his knees and took off her shoes. He kissed, sucked, and squeezed one toe after another. Then he rubbed the tops of her feet, massaged her arches, and rubbed her heels.

"Let's go into the bedroom."

Ms. LeGrand told Todd to unzip her dress. He was nervous, but he managed to help her get out of her outfit. She then told him to unhook her bra. She took her arms out of it and let the bra fall to the floor. He saw that her nipples were hard, Her tits were round, full, and buoyant -- she showed her age somewhat, but not much.

Todd looked agog with his mouth open. Ms. LeGrand smiled.

"Give me a back rub, boy."

She lied on the bed face down, next to the bed..

Todd stood next to her and began rubbing her shoulders. He worked his way down her back, getting increasingly intense in his massage. She groaned.

"Keep it up, boy."

He massaged her ass through her panties.

"Oh, yes."

His hands worked their way up and down her back, gripping and rubbing her over and over.

"Kiss my back, boy."

Todd covered her back with little kisses.

"Now kiss my ass."

Todd gently pulled off her panties, exposing her toned but generous ass.

"My ass is your goddess. Worship her."

Todd ran his tongue over her buttcheeks, following with one sloppy kiss after another. He felt Ms. LeGrand thrust her ass on his face over and other.

"Now it's time for you to show me how you can really please me."

She flipped over and spread her legs. It was a familiar position for Todd, but it had never felt so intimate. His head lay between her legs. His lips met hers as his tongue worked her clit. He slipped a finger in and rubbed the front of her pussy. He inhaled her divine scent and tasted her tangy nectar. As was her wont, she placed her legs on his shoulders and grabbed his head and pushed him deeper into her. She soon groaning over and over. He felt her body trembling and twitching, until he heard her gasping as she came.

"Get on your back, boy. Mama's not done."

Ms. LeGrand straddled Todd's face, pushing her crotch on his face. She then lowered herself until her wet pussy was pressing on his mouth.. Todd began running his tongue on her labia and then up to her clit and then back again. He felt himself enveloped by her sex, used as a tool of her pleasure, with her needs completely overwhelming his will. He held her legs, helping himself get in even deeper. Her hands pushed down on his shoulders, keeping him at her mercy.

Sometimes he could barely breathe, all the time he was enmeshed in her smell and taste. Finally, he felt and heard Ms. LeGrand come.

But t wasn't over.

She lay down and spread her ass and pushed it in his face. "Time for dinner, baby boy."

Todd began running his tongue around Ms. LeGrand's asshole.

"There you go, boy."

He then began darting his tongue in and out. Todd pressed his face deeper into her ass, showing his devotion to her hindquarters. Ms. LeGrand pushed her ass harder on his face, until he could barely breathe. He kept working her beautiful asshole with an almost religious fervor.

She moaned. "Yeah, that's what Mama needs, baby. Eat my ass. Eat my motherfucking ass. Do you love my ass, boy? Tell me."

Todd briefly extricated himself. Gasping, he answered, "I love your ass, Ma'am. I love your gorgeous asshole."

"Good, you should."

Todd went back to work. He realized that he no longer had a will of his own. He just lived to please Her.

Suddenly he felt a burst of a hot air on his face and heard a BRAPPPP.

Ms. LeGrand had farted on his face.

She laughed. "That's what happens when you have asparagus for lunch."

She then dismounted from Todd's face. He was gasping for breath, but his cock was rock hard. Ms. LeGrand smiled at him. She straddled his crotch and then slid onto Todd's penis. She began fucking him enthusiastically. Todd moaned as he felt Ms. LeGrand's pussy gripping his cock.

Todd pushed back up into her. She groaned loudly. She rode him harder, greedily taking his meat. His hands caressed her ass and fondled her tits.

"Fuck! Give me that fucking cock, boy. Give Mama what she wants."

Her pussy was so tight and wet, Todd could barely control himself. The two of them were fucking like animals, joined by pure primal need.

He felt her squeezing him over and over again, until he heard her crying out over and over again. He let himself go, shooting his load deep in her.

Panting, Ms. LeGrand pulled herself off of Todd. She then got off the bed and walked over to the dresser. She pulled out a black cloth bag. Then she took out a harness, a large black dildo, and some lube.

"When in San Francisco..." she said with a laugh.

She put on the harness and stuck in the dildo. She told Todd to get on his hands and knees. He meekly obeyed.

"Let's open up that ass, boy." She squeezed lube onto the index finger of her right hand. With her left hand, she spread his left buttcheek. She pushed her finger into his asshole.

"Just relax, honey. Don't fight it. Mama won't hurt you." She thoroughly lubed up his hole. It felt cold and probing at first, but Todd relaxed and felt more comfortable.

Todd felt Ms. LeGrand's dildo pushing into him. Since he had been penetrated before, he knew he had to relax and open his ass to its new invader. As she pushed deeper into him, he began feeling it rub against his prostate. The feeling grew more and more intense, and he began groaning louder and louder.

"C'mon, boy. Take Mama's cock."

He felt her push in and out. He felt so full, so at her mercy.

"Yeah, that's what I like to hear. Take it like a good bitch. Tell me how you love it."

She swiveled her hips and pushed the dildo deeper into him.

"Fuck me. Fuck me hard. Fuck my ass please."

He groaned in joy. His dick drippled out a little precum and then shot his second load.

"That's a good boy."

Ms. LeGrand pulled out and unstrapped herself. She lied beside him and the two of them held each other.

"Wasn't that a nice time, my beautiful boy?"

"Yes, Ma'am. It was wonderful."

The two of them napped together for about half an hour. They then got out of bed, showered together, dressed, and left the suite.

They ate dinner together at one of Ms. LeGrand's favorite spots in Chinatown. Afterwards, they returned to the hotel and turned in early. They lay together in the king bed, spooning, until they both fell asleep.

They got up early to catch a morning flight back to New York. Todd spent much of the trip dozing on her shoulder.