On-the-Job “Training” with Linda

The morning was a very efficient, automated blur. The house made everything so simple that you were able to make and eat breakfast, shower, get dressed, and head out the door without ever taking your mind off its singular track; you have a “meeting” with Linda today. The only thing you did differently than normal was to wear some athletic style underwear that would, hopefully, restrain any erections that might spring up in anticipation. Hell, you were semi-hard from the moment you woke up.

The chime and the voice of the company assistant AI finally broke the trance and woke you up when the elevator doors opened on the fifth floor. “Red arrows today for you, Nick. Enjoy your meeting.” You were starting to think that these digital assistants were a little too aware of the goings on around this place, but you weren’t about to let that bother you. Your heart rate increased gradually as you neared a much larger office than yours. Three of the walls were glass with the back one a flat white that had been emblazoned with a massive version of the company’s logo. Suddenly, there was a sinking sensation in your stomach. Linda wasn’t at her desk. Had she decided against all of this? Would the AI still have led you here if that was the case?

As these questions raced through your mind, the door swung open and the assistant voice said, “Come in and have a seat Nick. Linda will be along shortly.” This calmed your nerves only slightly, leaving you in a heightened state as you heard the door swing slowly closed behind you. It seemed that Linda had given the room some instructions to execute upon your arrival, because the lights dimmed just slightly and the glass walls were suddenly opaque, reminding you of your first encounter with your “handler” yesterday. The only available seat right now was the Linda’s chair at her desk. Though wary about taking it, you weren’t about to disobey the instructions so you sat down and looked around the very modern space. It was only a moment before a new voice seemed to come from the walls. Linda’s sultry tone immediately made it clear that there was no pretense of this being purely a “work meeting.”

“Good morning, Nick. Are you ready to be rewarded? Because I’m fully prepared to give you exactly what you earned yesterday…” She sounded so aroused that it was impossible for you not to connect with that same energy. Your cock instantly began pressing against the stretchy fabric of your underwear as you answered, “I’m ready, Linda.” Your mind filled with images of her sexy outfit from yesterday, the inside of her desk drawer from her message, and even some of the possibilities for what might soon come.

“Good… Stand up and take everything off for me, Nick. Everything but your briefs. Leave your clothing on my desk, sit back down, and cross your wrists behind the back of the chair.” Her instructions were clear and clinical. She knew exactly how she wanted you to present yourself to her, and you were quick to oblige. Soon you were nearly naked and displaying a large bulge as you sat in the office chair. Your posture with your arms behind you made the chair lean back slightly so your body felt very exposed in the front. It was only a couple seconds after you had assumed this position that the white wall opened near one corner of the office. There was no indication that a door could have been hidden there, but it opened just the same and Linda stepped into view.

“Holy sh-” you were cut off.

“I don’t recall asking you to speak.” Your much more scantily clad handler stepped around you in her high heels, observing your exposed form just as you did hers. She turned the chair to face sideways in the room, away from her, and you heard the drawer open. Again, your heart increased its pace as you wondered just what she would pull out first. You felt, rather than saw, her first item as it softly wrapped around your wrists. The thin strip of silk made several revolutions around both hands before she looped it between them to tighten it all together and then secure it to the base of the chair. Your arms were stretched straight and your whole body pulled taut as a consequence. Linda came back into view, running a hand from your bare shoulder down your abs and lifting it just before it reached your waistband. “Excellent…”

As she stood before you, Linda’s eyes ate you up and she couldn’t resist licking her lips. “I’m going to give you every bit of pleasure I know you deserve. You did such a good thing for the company yesterday, Nick. Such a good thing for me…” As she spoke, she leaned forward and placed a hand on each of your thighs, forcing them apart slightly as she used them to lower herself to her knees. Her painted nails trailed up the inside of your legs, tickling them and increasing that steady flow of blood between them that only added to your erection. Though her fingertips came close when they felt the material of your briefs, she kept from touching your bulge for now. Up to this point, you had heeded her reminder to remain quiet until she gave you permission to speak.

Linda’s smile was a devilish one as she met your eyes. “You’ve earned this, but I still want you to beg for it. Go ahead, beg me for your reward.”

With no hesitation, you obeyed. “Please may I have my reward now, Linda? Please let me have it. I need it!” You really poured the desperation on thick and punctuated the request by thrusting your hips a little and clenching your pelvic muscles to accentuate your throbbing cock through the thin fabric. You could tell that this pleased Linda when she licked her lips again and grinned. She also pressed her hands down on your thighs to control that thrusting motion.

“So eager… Good boy.” With that admission of her approval, she finally brought her right hand farther up your leg and squeezed your cock through your underwear with a gasp. “Fuuuccckkk Nick…” You kept your hips still, letting the pleasure of her firm hand spread through your body as you let out a gratified moan. Linda started a slow forward and back rubbing motion as she continued to compliment you. “Your cock already feels incredible just like this.” Her off hand rubbed your thigh, and you knew she would use it to shut down any unwanted movement you tried to make. “You don’t know how badly I want to rip these shorts down and ride this dick until it explodes inside me… but that’s not your reward today.”

Another frustrated yet ecstatic moan struggled its way past your lips, but you managed to keep yourself from begging her to do as she suggested. You just focused on the sensations she gave you; on the gorgeous expressions she made while admiring the pulsating heat coming through to her soft hand. At one point, she focused her fingertips right on the underside of your cockhead in its trapped position and your arms involuntarily clenched, the silken cord reminding you of your current helpless state. It occurred to you that you were just as aroused now as you had been with two beautiful women begging you to take control and fuck them, but in a very different way.

“I could make you cum just like this. You know I could.” She let out another gasp as your cock twitched in response to her simple statements. “But I’m not going to, Nick. You deserve more…” Linda used both hands then to pull very slowly at the waistband of your underwear until your cock sprang up into the air to greet her. “Jesus fucking Christ…” She quickly got the briefs down your legs and onto the floor before wrapping both hands around your shaft, more to measure its length than to start stroking. “Excellent was an understatement.” She brought her plump lips forward, almost taking the head between them, but instead spitting onto it and letting it drip down to her waiting fingers. With just a couple repetitions of this and a few strokes she had you completely lubed up and you felt every one of your heartbeats as a throb with your cock in her grip. She was just getting started, but the pleasure was overwhelming and you threw your head back for a moment to moan loudly.

“Oh you love it, don’t you? You love when I reward you for being such a good boy.” Then the long, even, twisting strokes began in earnest. “God this is a fucking gorgeous dick…" Linda lovingly and expertly stroked you with both hands, letting out little noises of her own pleasure and fascination which only added to the overall effect. Despite your usual stamina, it wasn't long at all before you felt those involuntary movements in your hips as you neared the edge.

"Linda, I'm…" Desperation was creeping into your voice as you didn't want the experience to come to such a sudden and early close.

"Shhhh…" She accompanied the noise with an extra long and slow pull down your length with both hands. "You don't have to tell me when you're close Nick, I can feel it and I know exactly what to do. Mmmkay?" Her tone was chiding, but also so confident that it only elicited a moan in response from you. "Good." And then she went right back to it, slowing just enough to make you ride the edge without tipping over it. Every time her hands reached the head, her thumb made a little swipe at your frenulum that drove you wild.

The next time you threw your head back in pleasure her hands left your cock for only a couple seconds, but definitely long enough to cause you to straighten up and look at her. You were greeted with the sight of her top coming off. Her perfect handfuls topped with perky, erect nipples dropped out and she went immediately back to stroking, now causing them to jiggle delightfully whenever she sped up. "Oh your cock really liked that… You can barely take it, huh?"

She was right. Her hands were barely moving on your shaft now and her grip was loose for minimal stimulation. She completely avoided the head, knowing one touch there right now would be the end.

"It's time to decide, Nick. What you've done for me so far could justify me allowing you to orgasm in my mouth to end this 'meeting.' Or…" that devilish grin made a return, "you could give me the pleasure of denying you for now and earn more. 'More' being a much longer and more gratifying visit to my home."

As she explained your choices, you came back down from the edge just slightly, but she brought you right back with a quick flick of her thumb to that sweet spot.

"You choose."