Training the Intern

Jim looked over at his office clock and saw that it was already almost 5pm. By now, most of his co-workers would have slipped out early. It was not the busy season at the publishing company at which he worked, and people took advantage of the lull where they could.

There was a knock on the doorway of his open door. "I'm leaving now, Jim." It was Maureen, Jim's boss with whom he had a positive but fairly limited relationship. Maureen, who was a few years older than Jim, had worked hard to move up in the company. "Have a nice weekend. And please stop by and see Sheila on your way out. She says she has something to ask you about."

"Sure, Maureen. Have a nice weekend," Jim said, waving as Maureen headed out.

He slowly picked up his sport jacket from the back of his office chair and slipped it on, then began to gather his things to pack in his briefcase before heading home for the weekend. Since his divorce, he was a little less hurried when it came to getting home for the weekend. He had only the empty apartment to get back to, with only take out food and a rented movie to keep him company.

Before he could get out of his office, Sheila popped her head in through the door, smiling, and asked whether he could stop by her desk to help her with something. Jim, always a gentle and well-liked member of the staff returned the friendly smile and said he'd be glad to and would be along in just a moment, not mentioning that he'd already been asked. He finished packing up before turning off his own office lights and, when he saw that the common area outside his office was already deserted, shut the lights there as well before walking down the hall to Sheila's desk in the sales area.

Jim guessed that Sheila was in her mid-30s, several years younger than himself. She was a graceful, attractive woman with short brown hair and a million dollar smile. Jim had thought about asking her to dinner more than once, but ultimately felt it to be still a little too soon since his unpleasant divorce. As he approached her desk, he again noticed her confident smile, artful makeup and tasteful silver loop earrings. As usual, she looked great.

"Hi Jim, thanks for agreeing to come."

"Sure, always glad to help," he said, eyes adjusting to see that they were not alone. Leaning on Sheila's desk, and facing Sheila, was a very attractive young woman with dark hair and eyes and slightly dark skin. Her full lips and large eyes made her look striking, in an exotic way. She was tiny, both in height and weight. Nevertheless, he guessed she was about 19 or 20. He recognized her by sight, but didn't know her name. She was glancing downward, not meeting Jim's eyes.

"This is Malaya, Jim. She's been interning with us here in my group."

Jim smiled and nodded her way, but then noticed that she still hadn't looked up, so he said, "I'm pleased to meet you, Malaya."

Malaya looked up quickly and then back down at the floor, as if she was scared of Jim. Sheila seemed almost to be suppressing a laugh.

Looking over at Sheila again, Jim noticed for the first time that her top was unbuttoned to almost midway down her torso, showing quite a lot of skin. His eyes were fixed there, and he felt the excitement like a spark reaching his groin. He couldn't tell if she was wearing a bra, but assumed she was. Still, it felt like he could almost see far enough to find out. When he looked up, he saw that Sheila had caught him but rather than making any move to cover up or change angles, her confident smile turned a little more flirty.

He looked back at Malaya, only to see her stealing glances at his crotch.

"What was it that you needed?" he asked, more to Sheila than to Malaya. He noticed that his voice was cracking a bit, which caused him some mild embarrassment.

"You've always seemed like such a nice guy, Jim," Sheila said, as she stood up and took a step towards him, "and you've always been gentlemanly and considerate to me and the other ladies at this company. I felt confident that you were the right guy to discretely help Malaya and me. You see, Malaya is engaged and will be married very soon. She's a virgin and has no real experience with men. I promised to help her to get a bit so that the wedding night isn't something she fears. But you have to promise to keep this just among us."

"Oh!" Malaya gasped and covered her face with her hands, clearly embarrassed.

Jim's mind was racing. He was confused and aroused at once. "I'm sorry. What is it you're asking me?"

"Take out your cock, Jim. I've noticed a nice bulge in your pants before, and it looks like you've got a dandy right now. Let us see it. Let Malaya see it and get a good look. She hasn't seen a real man's dick and it's about time she did."

"Me? Are you s-serious? You want to see my dick? Don't you want to take her to a male strip show or something? I'm just an average guy. I'm no stud. And I'm really not a showy kind of guy, Sheila." he said, his face and neck turning suddenly red with embarrassment.

"Jim, unless her husband-to-be is a 6'4" body builder with an abnormally large dick, taking her to a strip show isn't going to accomplish what we want."

Sheila got up out of her chair while she was talking and brought her hand up to Jim's chest, gently stroking as she spoke. "We're hoping to get her over her fear of the unknown by seeing an average sized dick on an average sized man. Surely you can see the wisdom in this."

Jim tried to think, but knew he wasn't really able to keep a clear head. His arousal clouded his judgment, allowing him to ignore the fact that he was in his place of business and, despite the fact that the three of them seemed to be alone, he really couldn't be sure. But two attractive women were giving him the attention that he so badly missed lately. This could be fun, he thought, and somewhere in his swirling thoughts he wondered if this could lead to sex with Sheila.

"Okay," Jim said, pausing to bite his lower lip and take a deep breath, "you can have a look if that's what you want. How do I start?"

Sheila looked over at Malaya, and Jim saw that she was staring at his crotch intently now. Sheila brushed her hand over the front of his pants at the belt line, right above the bulge. "Take it out of your pants so she can see," said Sheila, a bit more firmly, moving her hands back to his chest.

Jim drew another deep breath and then reached down a trembling hand and unzipped his pants. He reached inside his underwear and took his semi-hard dick out through the fly so that about half his circumcised dick was showing.

Malaya drew a quick, audible breath.

"We're going to need a better look than that," said Sheila, dropping her right hand from his chest to his pants and moving her left hand around to the small of his back. She unbuttoned his pants and then, slightly roughly, pushed down his pants and underwear to his knees using both hands.

Jim realized just how exposed he was now. This was crazy. He was feeling a little panic, realizing he was in his place of business in a relatively open area, just minutes after close of business. His nervousness was gaining ground on his arousal, and his dick started to go soft.

Malaya was mesmerized. She stared at his dick but also looked at his face and the range of emotion playing across it.

Malaya then spoke for the first time since Jim arrived. "His penis is beautiful, Sheila. It's changing sizes, though. Why is that happening?"

"Jim is nervous, Malaya. A man's penis swells and stiffens when he's aroused, as I'm sure you know. But most of the time it's small. Right now Jim's nerves are causing his arousal to leave him. But I can teach you how to fix that."

Sheila ran her left hand up inside his shirt, stroking his torso, and moved her right hand to encircle his dick -- something Jim did not really expect. His cock jumped and immediately started to stiffen again. He could see Malaya smile in approval. The younger woman seemed to be finding her self-confidence. Sheila then gestured for Malaya to move closer. The young woman did so, and dropped to her knees, putting her face inches from Jim's now erect dick. Sheila moved her fingers so that only her thumb and index finger surrounded Jim's dick, and then she started to slowly move her hand up and down it's length. Jim responded by moving his hips with her rhythm and letting out a low grunt.

His eyes were closed and his head was swimming. He couldn't believe this was happening. He was excited and nervous, embarrassed and aroused. And the part of him that operated on basic instinct wanted this to turn into sex right now. Jim opened his eyes and reached down to stroke Sheila's hair, but she deftly brushed his hand away. "No touching us, Jim," she said firmly. You're just here to provide Malaya with a little first hand experience to keep her wedding night from being too frightening."

Sheila looked at Malaya then and said, "You need to know what it feels like to hold a man's dick in your hands. It is a feeling of power, one that every woman should understand and know how to use. You control his experience and pace." Sheila then used her full hand to encircle Jim's dick, no longer stroking. She tightened her grasp just a bit and then loosened again. She lowered her left hand and very gently fondled his balls. "Now you try, Malaya."

Sheila reached her right hand through Jim's legs and grabbed a cheek of his ass and squeezed hard. The sudden lack of contact with his stiff dick, plus the squeeze, caused his hips to thrust forward. Malaya took this as her invitation and grabbed Jim's dick with her right hand around the center of the shaft, laying her left hand gently on his right thigh as Sheila withdrew. The feeling of the younger woman's tiny hand was exquisite, made more so by the knowledge that his manhood was her first. He closed his eyes and reveled in this feeling.

As Sheila stepped closer, he could feel her breath on his face and neck. She quickly undid his tie and unbuttoned his shirt, and pushed his undershirt up above his nipples. She then ran her hands over his bare chest, pausing from time to time to pinch his nipples, all while Malaya learned her way with his rock hard dick.

"The tip is getting a little wet and sticky," Malaya said. "Is he having an orgasm, Sheila?"

"Not yet, 'Laya. That's pre-cum, a kind of natural lubricant that can help a man and a woman when it comes to penetration. That is a sign of advanced arousal, so I'd say you must be doing very well for a beginner." Both women laughed a bit at this.

The two women continued this, driving Jim crazy. Whenever Jim felt close to orgasm, Sheila would recognize the signs and signal to Malaya to back off, sometimes helping to slow things down by pressing firmly on the area where Jim's dick projected out from his body. In this way, they continued for what seemed to Jim like hours (though it was really only about 20 minutes) without letting him come. He remained rock hard throughout and felt an odd combination of extreme arousal and extreme frustration.

Suddenly, Jim felt hands on his bare hips gently rubbing up and down. As he turned his attention toward those hands he suddenly realized that they could not belong to Sheila or Malaya. Sheila already had two hands on his chest, and Malaya was at entirely the wrong angle and had at least one hand on him already. Someone had joined this party! Jim's body shook and jerked and he strained to turn his head to look behind him without shaking the other hands loose. To his shock, what he saw was the amused face of his boss, Maureen, at shoulder height with her hands on his hips.

"Looks like fun, ladies, I hope you don't mind some more company," Maureen said.

"We thought you'd never get here," Sheila replied, as she leaned in and took a nip of Jim's belly.

"Maureen, I ... You ..." Jim babbled. He was shocked and didn't know what to say. Maureen was an attractive woman of around fifty, always well dressed and refined. He had never thought of her in a sexual way, but that was changing all at once.

"Relax and enjoy it Jim. Sheila and I wanted to help Malaya and thought you could use a little fun, too. But please understand this is a one-time thing and come Monday we all return to our normal relationship like this never happened." And with that she suddenly pulled the jacket back off his shoulders and held it at the level of his upper arms, holding them in place.

Maureen leaned in and bit his neck at the open collar, and Sheila bit his left nipple, but again they kept him on the very edge and continued this for another 10 minutes or so.

Finally, Maureen reached down and pushed two fingers towards the very edge of Jim's asshole which, as she expected, caused him to thrust his hips forward violently. Malaya had been waiting for this, and used this opportunity to open her mouth allowing half of Jim's hard dick to enter. She sucked and licked hungrily, as Sheila had instructed her, and in short order Jim exploded into her mouth. She was surprised at the volume and the consistency, but was extremely proud of herself and swallowed every drop. Malaya felt that she now had the confidence she needed for her wedding night.

The three women laughed and squeezed Jim before letting him go and walking away and out of the office without saying another word to him. Jim was still shivering from his orgasm, and the unexpected way the events had developed. His clothes were pulled every which way around him. He caught his breath and dropped into Sheila's chair for a moment before pulling himself together.

Quietly, in a dark corner of the open sales area twenty feet away, a young woman in maintenance crew clothing waited for Jim to leave and then shut down the video camera she had been instructed to use to capture the erotic events of the afternoon. Maureen would enjoy that video recording many times in the months and years to come. And so would the young woman with the camera, as she fully intended to make her own copy before turning over the camera and tape to Maureen.