· 9 min read
The Devoted Assistant - part 2
You return to the office after your meeting and find Jackson waiting for you. You thank him for his help and dismiss him for the evening. As he leaves, you can’t help but feel a sense of satisfaction and power knowing that you have complete control over your relationship.
The next day, you arrive at work and find Jackson already at his desk, preparing for the day ahead. You exchange pleasantries before getting down to business. Throughout the morning, you notice him stealing glances at you, a mixture of admiration and desire in his eyes.
At lunchtime, you decide to test Jackson’s boundaries further. You invite him to join you for lunch at a nearby restaurant, knowing it is a popular spot for business meetings. As you walk into the restaurant, you see several of your male colleagues dining together. You approach their table and introduce yourself, engaging in friendly conversation while Jackson watches from afar.
You can feel his eyes on you as you laugh and flirt with your colleagues, enjoying the attention they are giving you. After a few minutes, you excuse yourself and return to Jackson’s table, where he sits nervously twirling his fork in his hands.
‘How was it?’ he asks quietly, avoiding eye contact. ‘It was fun,’ you reply with a smile. ‘I think I might have some new friends.’ Jackson nods, but you can see the tension building within him. He wants to ask more questions but doesn’t know how to approach the subject without overstepping his boundaries.
As the week progresses, you continue to push Jackson’s limits, engaging in flirtatious conversations with male colleagues and clients, always making sure he is aware of your actions. You can see the conflict within him growing as he struggles to reconcile his desire for you with his need to please you professionally.
One evening, after a particularly stressful day at work, you decide to take Jackson home with you. As you walk into your apartment, you notice the tension in his shoulders and the way he avoids looking directly at you. You know that he is struggling to contain his emotions, torn between his desire for you and his loyalty as your assistant.
You lead him into your bedroom and close the door behind you. ‘Take off your clothes,’ you command softly. Jackson hesitates for a moment before slowly undressing, revealing his slender frame and taut muscles. You can see the outline of his erection pressing against his boxers, and you know that he is aching to touch you.
‘Lie down on the bed,’ you instruct, pointing to your large, comfortable mattress. Jackson obeys, lying on his back with his hands at his sides. You stand at the foot of the bed, admiring his vulnerable form before slowly removing your own clothes, revealing your toned body and perfect breasts.
As you climb onto the bed, straddling Jackson’s waist, you can feel his heart racing beneath you. ‘Do you want me?’ you whisper in his ear. He nods, unable to form words. You smile and lean down to kiss him gently on the lips before sliding your body lower, taking his erection into your mouth.
Jackson moans as you begin to suck him slowly, teasing him with your tongue and lips. You can feel his hands balling into fists at his sides, desperate to touch you but unsure if he has permission. After a few minutes of tormenting him with your mouth, you slide back up his body and position yourself above his erection.
‘Are you ready for me?’ you ask, looking into his eyes. He nods frantically, his breath coming in short gasps. You slowly lower yourself onto him, feeling him fill you completely as he moans with pleasure.
You begin to ride him slowly, your hands on his chest for support as you move up and down his length. Jackson’s eyes are locked on yours, his desire and vulnerability plain to see. As you increase your pace, you can feel his grip on your hips tightening, but he remains still, allowing you to control the pace and depth of your thrusts.
As you near orgasm, you lean forward, pressing your breasts against Jackson’s chest as you grind against him with increasing urgency. You can feel his cock throbbing inside you, and you know that he is close to reaching his own climax.
With a final thrust, you cry out in pleasure as your orgasm washes over you, your body shuddering with the force of your release. Jackson follows soon after, his hips bucking upwards as he empties himself inside you.
As your breathing returns to normal, you roll off Jackson and lie beside him on the bed, your bodies still entwined. You can feel his heartbeat slowing down, and you know that he is content in this moment, completely devoted to you and your desires.
In that instant, you realize that you have found someone who not only accepts your kink but embraces it, allowing you to explore your deepest fantasies without fear of judgment or rejection. As you drift off to sleep, your fingers intertwined with Jackson’s, you know that this is just the beginning of a thrilling new chapter in your life.
‘You look stunning tonight,’ Jackson whispers as he helps you into your coat.
You smile, knowing that his compliment is genuine. You chose this outfit specifically for its ability to draw attention - a tight, red dress that hugs every curve and leaves little to the imagination. The neckline plunges low enough to show off your cleavage, while the hem barely grazes your thighs.
‘Thank you,’ you reply, giving him a sly wink. ‘I thought it might be appropriate for tonight’s event.’
Jackson’s eyes widen slightly as he takes in your appearance. He knows exactly what you’re trying to do - test his boundaries and push the limits of your cuckolding relationship. And judging by the bulge in his pants, he’s more than a little turned on by it.
As you arrive at the work event, you waste no time in making your presence known. You mingle effortlessly with your colleagues, laughing and flirting shamelessly. Every so often, you catch Jackson’s eye from across the room, his gaze fixed on you as he watches your every move.
The first time you feel a hand on your lower back, you know it’s only a matter of time before things escalate. You turn to face one of your male colleagues, his eyes locked on yours as he leans in close.
‘I’ve been thinking about you all day,’ he whispers into your ear.
You smile and playfully bat your eyelashes at him. ‘Is that so?’ you reply, feigning innocence. ‘What exactly have you been thinking about?’
He grins, his hand sliding down to rest on your hip. ‘Oh, I think you know,’ he says suggestively.
You glance over at Jackson, who is watching the exchange intently. His jaw is clenched tightly, and you can see the mixture of arousal and humiliation in his eyes. It’s a heady combination, knowing that you have this kind of power over him.
Later in the evening, you excuse yourself to go to the restroom. As you walk away, you feel a hand brush against yours - it’s Jackson, silently asking if he can join you. You nod slightly and lead him to the ladies’ room, where you enter one of the stalls together.
Once inside, you lock the door behind you and turn to face him. His eyes are wide with anticipation as he watches you hike up your dress, revealing your bare pussy beneath.
‘I want you to touch yourself while I do this,’ you whisper, slipping a finger inside yourself. ‘And don’t you dare cum until I say so.’
Jackson nods, his hand already working at the front of his pants. You can hear his ragged breathing as he watches you pleasure yourself, his eyes filled with desire and submission.
After a few minutes, you pull your finger out and open the stall door. ‘Follow me,’ you say, walking back out into the main area of the event.
You make your way to the bar, where you order a drink and strike up a conversation with an attractive stranger. Jackson stays close by, keeping watch as you flirt shamelessly with the man.
‘I can’t believe I’m doing this with you while my assistant watches,’ you whisper into the man’s ear, your fingers lightly tracing his jawline.
He grins and leans in closer. ‘I’ve always had a thing for women who are a little bit naughty,’ he replies.
Without another word, you grab his hand and lead him to the bathroom. Once inside, you push him up against the wall and kiss him passionately, your hands roaming over his body as you feel his cock harden beneath his pants.
You break away from the kiss long enough to glance at Jackson, who is watching from a distance. His eyes are glued to the two of you, his hand still working furiously at his crotch.
‘I want you to keep going,’ you say, turning back to the man. ‘And don’t stop until I tell you.’
He nods, his breath coming in ragged gasps as he continues to pleasure himself. You return your attention to the man in front of you, kissing him deeply as you reach down to unzip his pants.
After a few minutes, you feel Jackson’s presence behind you. He’s close enough that you can feel his breath on your neck as he watches the two of you. The combination of arousal and humiliation is almost too much for him to bear, but he obeys your command and continues to touch himself.
Finally, you reach down and wrap your hand around the man’s cock, stroking him in time with his own movements. ‘I want to see you cum,’ you whisper into his ear. ‘Right here, right now.’
He groans loudly as he reaches his climax, spilling his seed onto the bathroom floor. You step back, allowing Jackson to come forward and clean up the mess with a handful of paper towels.
As you exit the bathroom, you glance at Jackson one last time. His face is flushed, his eyes filled with a mixture of desire and shame. But most of all, there’s an unmistakable look of devotion in his gaze - a reminder that he will do anything to please you and fulfill your every fantasy.