You're The Boss

Eighteen year old Tommy was fresh out of High School when he landed his first full-time employment as a clerk/messenger for a distribution company, eager to finally make some real money.

The job was low-paying for new employees but according to his friend Steve who got him the interview, there was plenty of room for advancement if he worked hard and kept his nose clean.

A tall, thin young man, Tommy was assigned to the stock room, where he filled requisitions and delivered them around the office of 300 employees. Everyone was welcoming and friendly to the newcomer and he got to know most of the employees, if only by face, but they all knew his name.

There was only one person who wasn't very pleasant: Mrs. Flam, the owner/office manager, who inherited the company when her elderly husband passed away. Though short in stature, she cast a huge shadow, never nasty with anyone but not warm, either.

Tommy was intimidated by her, as were most of the employees. She remained in her glass-walled office, rarely communicating with anyone but her personal staff.

In the first month he was on the job, he only spoke to her once. Her secretary ordered supplies and when he delivered them, she was away from her desk. Tom stood there peering through the glass at his employer. He estimated she was in her fifties, attractive with short blonde hair and too much makeup for his liking.

As if sensing she was being watched, Mrs. Flam looked up and saw the young man who she knew had been hired recently. Tommy, for his part, looked away, almost humbled by her gaze. He heard the door open and the clip, clip, clip of her heels. "Can I help you?" she demanded.

Tom felt his face redden as he looked up at her. She was even shorter than he had imagined, wearing what he guessed as four-inch heels. Her shirt was tight to her thighs so her steps were small, too. "Um, I'm sorry, I'm delivering supplies but Betty isn't here. I didn't know what to do with them."

"Well, standing there staring isn't the correct answer now, is it?" When he fumbled for an answer, she cut him off. "Just pile the stuff on her desk. She can sort through it when she gets back."

She pivoted on her heels, all four foot eleven of her and walked away, only to stop and spin around again. "What's your name?"

"Tommy, ah Tom, I work here," he stuttered.

"Yes, I know that." She seemed to almost smile. "Welcome aboard." She turned and was gone, back into her glass fortress.

When he caught his breath and unloaded the supplies, he glanced inside again, gratified that she had almost smiled, but she was busy reading some report and didn't seem to notice him.

For the next two months, he kept thinking about her, how cold and distant she seemed but that one half-smile told him there was a warm person inside the cold exterior. When they made eye-contact after that, which was rare, she would nod acknowledgement and move on, and Tommy found himself fantasizing about her. For a person her size, her figure was curvaceous, with her ass accentuated by the heels and her arched back and head held high. Her breasts seemed to thrust forward, causing the young man to day-dream about breaking down her iciness and releasing the tigress within.

It was a Friday at 4:45 that there was a knock on the stockroom door. It was also payday, so Tom was planning to really enjoy this weekend. He answered and there was Betty, Mrs. Flam's secretary.

"She needs you, now."

He followed her to the glass office and she knocked on the door. Mrs. Flam looked up and waved him in.

"Tom, right? I need you to do something. I have a report that has to be hand-delivered immediately. You will have to wait for a reply, hopefully not too long." She was busy folding and sealing the report, then writing the address down.

"I know you get off at five, and may have plans, but this is very important. Of course, you will be paid over-time for this along with any expenses." She looked up at him. "I hope this won't be too much of an inconvenience."

Tommy thought of what Steve said about opportunities and working hard and knew he couldn't refuse. "Oh, sure, no problem. Then I bring the reply back here?"

She shook her blonde head. "Unfortunately, I have a furniture delivery at home after work that I can't break. Take a taxi to my home. The number is listed on the envelope. I'll reimburse you and pay your cab fare home from my house."

It was an order, but the look in her eye said please. He nodded, took the envelope and left. It took an hour to get there and another hour before the reply was ready. Taxis are rare on a Friday evening and it wasn't until eight o'clock that he arrived at Mrs. Flam's home, a spacious estate in the elite part of town.

After paying the fare, he rapped at the large oak door. In a few minutes, he heard the clip, clip, clip of Mrs. Flam's heels.

"You made it!" she exclaimed in relief. "I called their office and they said you had just left. Please, come in."

He followed her into the lobby with a high, spiral staircase, to a book-lined den. Herr tight ass swayed in perfect timing to her heels clicking and she went to a bar where she grabbed her martini glass and sipped.

"Let me look that over," she said, reaching for the envelope. "I just want to make sure they signed all the appropriate places." She tore it open. "Oh, and fix yourself something while I do this. I'm sure you could use one after your day."

Again, he saw that half-smile, as he obeyed, taking a glass, then ice from the bucket and finally selecting a Scotch that he'd heard of but never could afford. He poured a healthy drink and sipped. Excellent. I could get used to this, he thought.

He watched her as she read and noted that although still in heels and a skirt, the top was different, with a few buttons undone, and he could see freckled cleavage that heaved as she took her breaths. The memories of her fantasies came rushing back as he scanned her face, with green eyes, red lips, and what was beginning to look like a smile.

"You're staring again," she said, matter-of-factly, and he looked away self-consciously.

"Sorry," he replied.

After a bit, Mrs. Flam folded the report and put it aside. "Thank you, Tom. You did me a great service. You spent three hours of your time, but let's put you in for six hours overtime. My way of saying thanks."

"Thank you, Mrs. Flam, you really don't have to."

"Tom, the first rule of business is, 'Never turn down a paycheck.' You deserve this."

She actually smiled this time as she sipped her drink. "I have one more favor to ask."

Tommy stared, wondering what now?

"I'd prefer it didn't get around the office that I had you come to my home. Small-minded people would enjoy starting rumors about the boss-lady. I'm sure many of them think I'm a witch anyway."

"I don't," he blurted out. "I mean, you can be a little scary at first, but that's just because people don't know you."

"Oh?" she answered, eye brow raised. "But you know me?"

When he couldn't find the words, she smiled again. "I'm just teasing. Besides, I have to keep a professional barrier between myself and staff so they don't feel I'm a pushover. Especially the men, who see women as less-qualified."

"I don't see how anybody could think you're not qualified. You've run this business for how long by yourself?"

She thought back to her husband and his illness. All told, she'd run the company for eight years and it had grown under her direction. Harry would have been proud. "You seem to know quite a bit about me, Thomas."

"I'm sorry, I was just curious about you and asked some of the older employees. I didn't mean anything by it."

She looked at him over the rim of her glass, this tall, skinny kid with the shaggy brown hair and trace of a beard. "How old are you?"

"Eighteen, Ma'am."

She laughed. "I have shoes older than you and you seem to see right through me."

Again, he was tongue-tied, and she said, "I wonder..."

"What, Ma'am?"

"I wonder how discreet you are."

"Huh?"

"Tommy, tell me what you think of me, really."

He swallowed hard, knowing that his answer could cost him his job. "I'm not sure what you mean."

She stared up at him and he was intimidated again, but felt as if he were being challenged to be honest. "Okay, here goes." He gulped his Scotch.

"You come across as strict and unfriendly but that's just an act. You're in charge and you know it. That's a real turn-on, a woman who can take control, but you're also very sad, and you shouldn't be. You're pretty and sexy and I'm sure there are a lot of guys that would love to hang out with you but you keep this guard up, like the glass wall that surrounds your office."

She watched him. "Are you finished?"

"Isn't that enough? Do I still have a job?"

"Pretty and sexy, huh? Is that how you see me?" He nodded.

"I don't get called sexy often."

"Maybe not to your face, yeah."

"Do you know how old I am, Tom?"

"I never really thought about it."

"But you still think I'm petty and sexy?"

He nodded again and she moved closer. "How good are you at keeping secrets?"

"If I say I won't tell anybody, I don't, period."

"So, if something should happen here, you wouldn't go back to the company and brag or boast?"

"Of course not," he answered indignantly. She seemed to be making a decision. "And age doesn't matter to you?"

"As a matter of fact, I kind of like it."

She had to reach up to get her hands around his neck and pull him down to her. "Maybe this is the martinis kicking in, but I'm going to take a chance." Her lips parted and he tasted her lips, a mixture of cherries and Vodka. She felt his lips part and his tongue invade her mouth, the Scotch reminding her of Harry. The kiss seemed to last for minutes and Tom's mind was racing. Was this really happening?

His hands went to her butt and pulled it towards him as he quickly became hard. She seemed to sense it as she ground her hips against him, loving how he cupped her ass. The kisses became more breathless as they quickly increased the pace. Tom kissed her neck, inhaling her scent as he neared full erection. His hand went to her breast and she moaned, stepping back and moving towards the leather couch. He followed.

When she laid back, he sat and leaned in, groping her tit as they kissed again. His fingers found the buttons and he easily undid them as she breathed deeply. Her breasts overflowed from the white lace bra and he nestled his head between them, kissing and feeling for the nipple. She groaned when he found it.

He hand was between them, finding his hard cock pressed against her and squeezing the shaft. He shifted positions so she had access and she began struggling one-handed for his belt. They sat up and she got it open with both hands, as Tom lifted his hips and she slid the pants down. His penis strained against his jockeys and she pushed him back, kneeling and reaching in. The cock throbbed in her hand as she pulled it out.

They kissed again and she was down, kissing the tip, then licking his scrotum, all the time working his shaft. When she finally opened wide and he felt the warmth of her mouth wrap around him, he knew he wasn't going to last long.

She gagged on him, then coughed and spit on his shaft, increasing lubrication as she jerked the pole.

Looking down at her, Tommy thought of how he had dreamed of this, never believing it could happen. He didn't want it to end too soon so he pushed her away and she gave him a puzzled look.

"You're gonna make me come," he explained and she smiled.

"That's the whole idea, isn't it?"

She dove back onto it, sucking and slurping, loving the power and control she felt for this young man who found her sexy. She tasted the saltiness of pre-cum and hungrily worked his shaft, feeling his body jerk as he neared the edge.

"Oh, Gawdddd!" he groaned as he unleashed a spurt and she swallowed only to feel the second and third shots deep into her mouth. She gulped again, stunned by how much cum he had. He held her head and she took it all, finally feeling him relax.

He looked down to see her smiling, with his white juices dripping from the corners of her mouth. He was out of breath but managed to pull her up to him and kiss her, his tongue tasting his own sperm.

"Sorry," he whispered as she lay above him, kissing his neck and purring.

"You're young, don't be sorry," she assured him, gently caressing his chest, and teasing his nipples. He fondled her breasts and realized he was getting aroused again. He unhooked her bra and moved her onto her back, finding her nipples hard and pointy, sucking on one, then the other as she enjoyed the attention.

He tried sliding her skirt up but it was too tight. "Wait," she ordered as she stood and undid the skirt, standing in old-fashioned stockings, not pantyhose, with those heels high-lighting the fashion. She wriggled out of her panties and he pulled her to him, kissing her breasts as she stood, then laying her back on the couch and spreading her thighs.

He trailed kisses up her inner thighs as she moaned with delight, finally arriving at her trimmed but thick bush, which he found erotic and animalistic. Her thick clit glistened with her moisture as he waited, letting her anticipation build before finally leaning in and taking the swollen membrane between his lips and licking.

She squealed in delight as he slid a finger, then two, into her wet hole. After several minutes, they were both ready, his cock again fully engorged and her head reeling from the orgasm he had produced, her first in many years.

He positioned himself above her and she grasped his shaft, guiding the head into her opening, oiling it on her juices before he pressed forward, sinking his entire shaft deep inside her.

He paused, giving her time to adjust to him, then began the slow rhythm of long, drawn strokes, in and out, and they stared into each other's eyes. He varied the pace, moving with her hips as she swayed.

She pushed him away and turned around, kneeling, and he followed her lead, approaching from behind, and she felt him deeper than before, hips slapping against her ass.

But she enjoyed the control and moved again, having him lie back and mounting him, so she had the dominant position. Tom didn't mind, watching her rise and fall above him, tweaking her nipples as she stirred her hips. Hands on his chest, she began moaning loudly, rocking faster as he thrust his hips up to meet her.

He felt his balls tighten again as she rolled her head again feeling her own orgasm peeking. He gave a final thrust, holding her up, arched as he came again, just as she screamed in delight. Their bodies spasmed and slumped, both spent and exhausted.

After a bit, she kissed his neck, whispering, "That was amazing."

"Yeah," he agreed, "it was." They kissed again as she rose, slowly steadying herself on those four-inch heels.

"I could use another drink. You?"

He nodded, sitting up and watching her clicking to the bar. He wondered what this would mean going forward when she turned and said, "Are you in a hurry to leave?"

He smiled and shook his head. "You're the boss."