Train the Trainerbyeroslit©
"The instructor for your new hire training will be Tori," Tom said. "She's our newest trainer, but everybody seems to like her; especially the guys."
Scott looked at his new boss to make sure his grin implied what he thought it did.
"She's really cute, but kind of shy for being a trainer," Tom added.
"How old is she?" Scott asked.
"Twenty five or twenty six. I think this is her second full time job out of college."
Scott thought back to five years earlier when he would have been the same age as Tori. He understood her feelings of insecurity in a corporate setting at such a young age. He'd been lucky and worked his way up through the field of product design and development until he felt somewhat secure. Maybe he could offer some words of encouragement for her.
And maybe she was single, like himself. Maybe...training wouldn't be so boring after all.
Tori looked at her calendar and opened the appointments for her new hire training the next two days.
"Damn. Just one guy," she said to herself.
She hated one-on-one training the most when she didn't already know the student. If he didn't talk, didn't participate, the day seemed to drag on forever. She always felt self-conscious in those settings and she knew it came across in her presentations.
She looked at the appointment details. Scott Daley. Product D/D. So he'd be a nerd on top of it all.
"Great. Maybe I can call in sick," she thought.
Tori showed up for work the next day, as always, and made her way to the tiny, isolated training room. It bothered her that the company put so little importance on training that the only space they provided was a window-less converted storage room in the deep recesses of an otherwise nearly empty floor of the company's annex. Tori convinced herself on day one that she would change the firm's attitude about training. For now, she used what they gave her.
She arrived at 8 AM for her 9 AM training with Scott. The agenda included a history of the company, the computer applications he would be using, safety rules and regulations, and assorted stuff she could teach in her sleep. Most of the hour was spent filling the refreshment tray, getting ice, and stocking up on coffee.
Scott was in the parking lot at 8:45, but it took him ten minutes to actually find the training room, roaming up and down hallways like a freshman in high school. When he finally found it, he knocked softly on the open door and entered.
Tori had previously trained secretaries, janitors, vice presidents and accountants for the company. She used to make up mental images of the men in her classes before they showed up. They would always be young, handsome guys with athletic bodies. The reality was never as good as her dreams.
Then she saw Scott.
He was young and handsome with an athletic body and she stood frozen in the center of the room as she stared.
"Hi," he said. "Are you Tori?"
"Uh, yeah. Hi."
In those few seconds, Scott determined he might be looking at the sexiest woman he'd ever seen. Beautiful dark blonde hair framed a gorgeous face that looked much younger than she really was. A delicate blouse clung to her body just enough to reveal ample breasts and a small waist. Dress slacks highlighted her long, lean legs.
"I'm Scott. Hope I'm not late."
"Not at all," Tori said, extending a hand to take his. "Come on in."
"At least we shouldn't have to worry too much about being interrupted," Scott said. "They hid you very well."
Tori laughed nervously. "It's part of the on-boarding process. See if you can find the training room."
"I'm glad I did," he said, catching Tori's eye as she looked back over her shoulder while leading him toward the snack table.
"This is the best we could do as far as food for you. And some juice, pop, and coffee. Help yourself."
Scott eyed the choices. "Thanks. Maybe later in the morning."
"That's fine," Tori said. "It will be here all day."
He'd now seen her from every angle and was no less convinced she was a beauty. The blouse hung open sufficiently to hint at her cleavage and he tried not to stare. If his schedule was correct, he'd have all day to take in her attractiveness.
"So, am I going to be the only one?" Scott asked.
"Yep. You get my personal attention for two days."
His eyes widened with interest. "Does that make for a better or worse class?"
Tori shrugged. "Depends. I'll try not to bore you."
She brushed the hair away from the side of her face. Scott was finding every move she made to be sensuous.
"I'm sure you won't."
"Ready to get started?" Tori asked.
"Let's do it."
Scott chose a seat near the front of the room, on the center aisle. It was a simple computer station with a comfortable chair and plenty of leg room. When Tori asked him to tell her a little about himself, he stuck to the basic educational background and work experiences. She asked about hobbies and he replied honestly with references to sports and traveling.
All he learned about her was that she graduated three years earlier and loved her job. Scott selected to hold off on more probing questions until later in the day. With that, Tori dove straight into her prepared material.
There was nothing she was saying that impeded Scott from paying attention only to the way she moved. Tori drifted with ease from one side of the giant whiteboard to the other, providing her student with a panorama of front, back and side views. Light from the overhead projector flashed on her blouse as she walked through it, casting all new shadows around her curves.
Her voice was steady, belying the anxiety she always felt at the beginning of a new session. Scott seemed quiet and she dreaded a potential two days of pure lecture and little interaction. But about one hour into the class, he began inquiring about available computer programs and how the company did certain things. The rest of the morning breezed by quickly.
When it was time to break for lunch, Tori made it clear without actually stating it that they would not be eating together. Scott didn't push it and came back at one o'clock for the continuation of the training. But, he had decided it was time to liven things up.
His first comment, when she asked if he was ready to start, was: "Do you ever come into this room just to get away? I mean, it's so out of the way and secluded."
Tori shrugged with the same tilt of the head Scott was getting used to from her. "Sometimes. I don't always feel all that safe coming back here by myself."
"It would be a great place to bring your boyfriend," Scott said with a straight face.
"If I had one," Tori replied with equal seriousness.
Scott grinned. "Girlfriend?"
"No!" Tori snapped back, much to Scott's delight.
"So, tell me," Scott said before an elongated pause. "You teach the same thing every week. Over and over. You could do it blindfolded. Do you ever let your mind wander. Maybe think about what the guys in your class would look like naked?"
"Scott!" After allowing her surprise to show, Tori added, "I'm not sure I've ever had anybody that good looking."
"Oh, c'mon. There had to have been at least one dude you thought about. Maybe when you got home, by yourself..."
"Stop it," she demanded playfully. "And no doubt you've done it with instructors, right?"
"Of course," Scott answered immediately. "I mean, there's only so much attention I can pay to how Outlook works. So I think about her on a beach in the Caribbean, laying on a towel. Maybe it's a topless beach. Or she's in the cabin of a cruise ship changing into a summery dress for dinner."
Tori couldn't believe he was delving so closely into how her own mind worked. Naturally, she had done the same thing with guys in the class. Before the day was done, she was likely to do it with Scott and somehow he knew.
"Well, I can't say I do the same," she said.
"I think you're lying. You're an attractive, single, young woman and I assume you have the same fantasies as the rest of us," Scott told her. "Tell me what you thought about with the best looking guy you've ever had in a class."
Scott smiled. "Did you start with his shirt or his pants?"
Tori feigned disgust at the line of questioning, but inside her heart was pounding and she refused to acknowledge the feeling between her legs. Suddenly, the room seemed even smaller than it was and she was cut off from the outside world, trapped with Scott. Like a prisoner, she felt helpless. Her mind was blank.
The words were out of her mouth before she even realized it. A strange sense of excitement overwhelmed her.
"Was he muscular. Do you like that?" Scott asked.
"He doesn't need to be. I like muscular arms," Tori explained.
Tori could feel the flush on her face. "I think about what he's wearing under his pants."
"Do you prefer briefs or boxers?" Scott said with seemingly authentic interest.
Tori giggled and considered ending the whole discussion. Instead, she answered, "Briefs."
"And do you take them off him or have him do it?"
"Scott, I think it's time we get back to our training," Tori said.
"Tori, we have plenty of time for that. I just want to get to understand you better. Find out what goes through that pretty head," Scott said.
"For some reason I'm not sure I want to know the same about you."
Her look conveyed true apprehension, but Scott wasn't concerned.
"I think you do."
They stared at each other for a long, long moment. The silence was deafening.
"Go ahead," Tori finally said in a near whisper.
Scott leaned forward and made sure he had her full attention. "I think about you in that blouse, wondering what type of bra you wear. And does it hook in the front or back. Then I wonder what it holds; what your breasts look like."
He saw the astonishment on her face. But Tori didn't speak, despite the body language that displayed her discomfort. Scott believed, but couldn't prove the fact, that the young instructor was turned on by his little speech.
"I think about what your panties might look like or what color they are. And I wonder how much of your cute ass they cover. I picture you in your bra and panties, slowly removing them for me so I can see you naked. Then I wait for your instructions."
Tori stared at him as if in a trance even after he was done speaking. She put a hand out to lean against the instructor's podium and Scott smiled. Tori said, "Well. I'm sorry I asked."
Scott laughed. "No you're not. I just convinced you that you're normal after all. We all do it, Tori. But how many times have you acted upon it?"
"What do you mean?" she asked.
"How many times have you approached a guy in your class and tried to answer the questions you had about him?" Scott said. "How many times have you found out if he wore briefs or boxers?"
"It's not...I mean...it wouldn't be...," Tori stammered.
"Does your bra hook in the front or back, Tori?"
Scott saw her hand shake as she shifted positions. Her eyes avoided his.
"Well?" he inquired.
Tori was gazing down at her shoes with a bewildered look on her face.
"Show me. Unhook it," Scott said. "You can do it through your blouse, can't you?"
Now she looked at him the way a scared child would look at an adult. As if in slow motion, her right hand moved behind her back and fumbled for the hook. Scott watched her movements until, finally, the hand returned to her side.
He stood up and approached her. Scott circled around her and Tori watched every step he took. He stopped when he was behind her, Tori still looking back over her shoulder. Scott put his hand in the center of her back where the bra would have connected.
He slid the fabric of the blouse back and forth until he could tell the bra was unhooked. He pressed his fingers against her body and lightly rubbed, separating the bra straps a little bit more. Tori was looking straight ahead again and Scott sensed the tension in her back.
"You're missing out on life, Tori, if you keep suppressing all the good things you like to do. There's absolutely nothing wrong with fantasizing. It won't hurt you," Scott told her.
He was all but massaging her back, spreading out his fingers and stroking a wider area.
"You have the right to wonder what's inside a guy's pants. Take it upon yourself to find out," he said.
They stood for a moment, the only sound breaking the silence being the silky sound of Tori's blouse sliding back and forth.
"Do it," Scott said, hoping she knew what he meant.
Soon, her hand was sliding backwards until it hit his pants. A slight shifting put it squarely on his crotch. She stopped at the feel of his semi-erection under her fingers.
"It's OK, Tori."
She barely heard his words, and started to slide her palm up and down.
"What's your guess? Briefs or boxers?"
"Very good," Scott said with a wide grin.
His hand started gliding down her back, all the way to the top of her pants. At the same time, Tori's fingers tightened their grip on Scott's cock. Scott let his hand continue past her waist and onto the top of her ass. He felt Tori inch forward slightly, but not enough to escape him.
"What's your guess?" Tori said.
He suspected she was referring to her panties. He searched out the outline of them through her pants and massaged her ass tenderly.
"Conservative. Simple. Not as small as I'd prefer."
Tori tried desperately to restrain her giggle, but it got out.
"You're awful," she replied.
"Then why are you squeezing my cock?"
With that, she pulled away quickly and turned to face him. She was redder than ever and more beautiful than Scott could imagine.
"We need to finish training," she said.
"Kiss me first."
Tori couldn't have stopped herself if she tried. She moved to him and they embraced, started a deep, long kiss with tongues fighting for space and a few moans added for good measure. His cock pressed against her throbbing pussy and he felt her breasts against his chest.
When it was over, Tori took a deep breath and turned away. Scott grabbed her arm, but not in a threatening manner.
"Tori, I want you to do something else."
"Do you own a dress?"
"Wear it tomorrow. No bra. No panties. I want you to teach in the morning like that. After lunch we'll talk about how you feel. Can you do that?"
Scott felt the muscles in her arm twitching from nervousness. Again, she didn't answer; just nodded.
He watched her fasten her bra as he sat down.
Tori was never as happy to get home as she was that night. Two different times she nearly crashed while deep in thought about what had occurred at work. She remembered the sensation of Scott's hardening cock in her hand, and his fingers on her back and ass. She remembered how her bra loosened around her breasts and the erotic feeling of being even slightly undressed for him.
Under any other circumstances, she would have ran to her bedroom, stripped, and masturbated until she came with loud moans of pleasure. But she couldn't. She had to wait for tomorrow, when she would teach him in a dress with nothing on underneath. Her horniness would increase by the hour until after lunch. And then...what? What then?
She didn't know. But she wanted to find out.
The dress she chose for the next day was not, of course, what she would typically think of wearing to work. It was fairly short, body-hugging, and low cut. She hoped Scott liked it, and that none of her bosses showed up. But she knew they wouldn't and right now Scott was more important, anyway. Never, in her short career, did she ever want to go to work as much as she did at that moment.
After a fitful night of sleep, Tori showered and slid on the dress, feeling sinfully naked as she drove to work. She imagined every person in every car she passed staring at her, knowing she had no underwear on. She tugged on the hem of the dress at every stop light and made sure nobody was in sight when she exited the car in the parking lot. For once, she was glad her building was empty.
At five minutes to nine, Scott entered the training room. He greeted Tori and smiled his approval at her dress. Nothing was said about it and training started as if nothing was different. The few times Tori leaned in to assist Scott with something on his computer, she saw his eyes travel to her breasts. Minute by minute, she was getting more excited and finding it more difficult to concentrate on the lessons.
Around eleven, Tori turned from the whiteboard to find Scott slowly stroking an obvious erection through his pants.
"Scott, how am I supposed to teach with you doing that?" she said.
"You're supposed to be doing the same thing as me. Wondering what we'd be doing right now if we were naked," he answered.
"Who says I haven't been?"
He laughed. "Then you have more self-restraint than me."
"Not much," she admitted. "Now let's do the last exercise before lunch."
Mercifully, lunch time arrived and they agreed to meet back in the room at one. Tori couldn't eat and Scott had trouble controlling his erection at the restaurant he went to. As he re-entered the training room, he knew his agony would soon be over. Tori waited for him anxiously by his desk.
"How was lunch?" he asked.
"Too long," she said. "How about you?"
"I thought about you."
"Oh no," Tori said with a grin.
"Yes, it made me hard. And I considered all the options. I came to one conclusion," Scott said.
"You haven't fulfilled that one, big fantasy yet, Tori. All those times you thought about teaching a class of guys while naked. Now you have a chance."
He was seated and looking up at her cute face. She played with her hair in nervous, little movements. She looked away.
"I don't know, Scott."
"Do it, Tori. You'll regret it if you don't," he said. "Go lock the door and come back. Please, Tori."
She walked slowly to the classroom door and turned the lock in the door knob. Tori stood for an instant before starting back. She wasn't sure her legs would support her.
Tori stood next to Scott's desk.
"Take off your dress, Tori."
In the face of all of her doubt and fear, Tori was excited by the opportunity to live out one of the darkest fantasies she had. Scott was right; she'd regret it if she didn't. Teaching in the dress without a bra or panties had been a thrill. Being nude in front of him was something she could only dream about before yesterday.
Scott watched attentively as the young instructor reached behind her neck for the top of the dress' zipper. He heard it open and Tori lightly held the dress in place for a few seconds. Then the straps were lowered from her shoulders and, inch by inch, her body was revealed from the neck down.
His first glance at her firm, full breasts caused his cock to twitch with anticipation. Her flat stomach and tiny waist were flawless. As the dress sank lower, he got his first look at her pussy. Tori's legs were close enough together to only give him a hint of the neatly trimmed hair and pink lips, but as the dress fell to the floor and she kicked it off, the youthful perfection came into view.
She stood straight and did not move, her face clearly showing the anxiety she felt inside. Scott inspected her from head to toe.
"Turn around, Tori."
"God, Scott. I can barely move I'm so nervous," Tori said.
Scott smiled. "You're doing fine."
Tori made the half turn he wanted and stood stiffer than before. With her legs tightly together, her small, tight ass was even more beautiful and inviting. Scott fought the urge to rub his cock, knowing the best was yet to come.
"Beautiful," he said. "Now teach me the next lesson."
Tori turned back around, awkwardly crossing her arms in front of her.
"I'll make it a short one," she said with a tone of defiance.