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Instead of working, he spent those minutes contemplating the best place to open the mystery package. If there was anything he had learned from his previous play weekend with Allison it was that her creativity and deviousness were not to be taken lightly. The idea of any of his coworkers figuring out exactly what he was up to if it was something kinky was the last thing he wanted.
Most of the bathrooms that were close to his department were in common areas and had several stalls. If he had his way he would rather not have anybody else even remotely near him when he opened this package up. It was then that he remembered there was a small personal bathroom in the adjacent professional building that was attached to the parking garage. Hardly anybody knew it was there, let alone used it. It would be a bit of a walk, but the added privacy would be more than worth it.
When it was time he grabbed the package and began to make his way across the drive and to the professional building. He took the two flights of stairs down to the basement and was happy to find that the bathroom he was thinking of was unoccupied. In fact, he hadn't encountered anybody that he knew on his way there, which was good since he didn't feel like much like talking. As soon as the door closed he locked it and whipped out his cell phone, utilizing the wifi to send a quick text.
"Mistress, I'm in the bathroom alone with the package now," his fingers glided over the letters. His stomach began to do flips in anticipation; he saw that she was typing a response.
"Go ahead and open the box."
Without a seconds hesitation he pulled out his work keys and dug at the seam of the packing tape. Inside was a manila envelope. Underneath it was a piece of paper and another box. He looked at the picture and read the label, 'Roll Play Medium", it appeared to be a butt plug of some sort. Flipping the piece of paper over, he saw that it had instructions on it.
**
slaveboy,
1. Get this plug in your ass. It will remain in place until I tell you it is ok to take it out. It will serve as a constant reminder that your ass belongs to me. I've included some samples of lube; you better hope it's enough.
**
Quickly he foraged around the bottom of the box and found a couple stray packets of lubrication. This was the first time he had ever done anything like this at work and the entire thing made him nervous. How in the hell was he going to get this thing in without being able to lie down? At least he had had the sense to seek out a private bathroom so there weren't any strangers coming and going.
His cock was already hard at the prospect of sliding that toy up his ass as he ripped open the box and pried it out of the plastic insert. It was about four inches long and smelled like silicone. The base was flared but pliable, not hard rubber like the butt plug set that they had at home. Most importantly, when it dropped out of the packaging and into his hand, he could feel a weight rolling and jiggling around inside of the toy. It must have been intended for enhancing his pleasure, but personally he doubted it would do much.
Setting the toy on the counter by the sink, he opened one of the lube packets and began to apply it generously on the tip of the plug, smearing it around and trying his best to disperse it without making a mess. He propped one leg on the counter by the sink, and held his button down shirt out of the way with one hand. With his other hand he slowly began to work the tip back and forth against his opening.
Taking a deep breath he applied steady, even pressure. The toy began opening him up and he took his time, not wanting to hurt himself. It took the better part of ten minutes, but eventually he felt the toy disappear inside of him, his cheeks squeezing around the narrowed portion, with the base still outside of him. It was more comfortable than most of the anal toys that he had tried.
As he turned to go back to her instructions he felt the subtle rolling of the ball deep inside him. It brought his attention back to the fullness in his ass, but it was a mild tease at best. He wanted to stroke his cock so badly; it stood straight out in front of him, fully erect. Taking a couple of steps he realized that the toy would be hard to ignore, every movement caused the weighted ball to tumble and roll, stirring his arousal. He had to clench his cheeks tight to keep the lubed toy from sliding out of him.
He glanced back down at the contents of the box and grabbed the envelope. Near the opening it contained more instructions.
**
2. Open up the manila envelope and see the second surprise that I have in store for you. You are going to need it if you don't want to lose your new toy.
**
Curious, he ripped the end of the manila envelope and peered inside. To his shock he saw a pair of satin, pink, thong panties. As he unfolded them he saw they had a small black bow adorning them. His stomach churned. Wearing panties was never something that he had fantasized about or even thought about. There was no way he could do this, it was just wrong.
Yet as he handled the delicate and soft fabric he couldn't help but imagine what it would feel like cradling his cock. The thought of being forced to wear them made him harder than ever. It wasn't like anybody would ever know about this or that it meant that he liked dressing like a girl. Fuck, he thought to himself, they had only been playing for three hours and she had him so turned on that he couldn't believe he was actually considering doing this. Deep in contemplation about what to do, he saw his phone light up out of the corner of his eye.
"What seems to be the holdup slaveboy?"
It was then that he wondered if he had gotten himself in over his head. Clearly she knew that she had gotten into his headspace and was pushing his limits. He held the thong up tentatively, and it looked like it might fit him, which was no small feat since he was 6'2" and about 220 lbs. He wasn't in bad shape, but he was hardly a fitness nut either.
What the hell, he finally decided; this wasn't anything that would legitimately harm him. He carefully removed his pants and boxers so as not to lose the toy buried in his ass, and slowly began to pull the satin material up his legs. It was every bit as sensual and soft as he imagined it would be. He pulled the material up to his waist. The thong portion rested nicely, holding the butt plug in place. He even managed to fit his cock in the front, though it strained at the fabric, rubbing against the silky material. There was a spot of precum that had leaked onto the material from how constrained and aroused he was.
With the thong in place he could relax and the toy stayed in place, the weight inside bounced as he saw a piece of paper in the envelope.
**
3. Take a picture and send it to me, that way I know you can follow directions.
**
Reluctantly he reached for his cell phone and took a picture of himself from the front, his cock still stretching the soft pink fabric and the black bow highlighting his bulge. Something about seeing that picture made it more real for him. He sent it to her and began packing his boxers, her directions, and the packaging for the butt plug back into the plain brown box. There was no way he was going to leave it in the trashcan for someone else to find.
"Looking sexy slaveboy," she texted him, "but let's see the back."
It made him feel incredibly feminine and submissive trying to figure out the proper angle to take a selfie of his ass in the mirror. Finally he got a decent shot that allowed her to see the fabric stretched over the toy and running snugly up his ass. Once he finally got one and sent it to her he realized that there were only a few minutes left of his lunch break.
He exited the bathroom and decided his best course of action was to ditch the box in his car on the way back to his office. There was a stairwell close by that led back up to the level he was parked at in the garage. Walking up the steps made the weight in the plug jiggle and it drew his attention to the uniqueness of the sensation. Between that and the soft fabric of the panties, his cock was desperate for attention.
Making his way to the car he passed several groups of strangers and a few random employees he had never seen before. He couldn't help but think that everyone he came into contact with knew his secret. Silently he debated whether it was better to avoid eye contact or to greet people in hopes of distracting them from scrutinizing him further. Glancing down he realized that his pants were loose enough that it was very difficult to notice the bulge unless you were staring right at it, which most people wouldn't do. With this reassurance he hurried along, dropping off all of the packaging in the trunk of his car and making it back to his desk with two minutes to spare.
He wondered what all of this had to do with her plan of getting pregnant exactly. If anything, not having room for his testicles to breathe would decrease his fertility he thought to himself.
"I zoomed in on that pic and I can see you have that plug in your ass, I have to ask, how is it?" she texted him.
"It's subtle but nice," he replied, wondering if this softer side was a chance for him to broach the subject. "I'm just curious Mistress, how exactly is making me wear panties going to help you get pregnant?" He reread it after he sent it and it sounded more assertive than he meant for it to sound.
"Rule 2 slaveboy...it's all about ramping up your arousal. Face it; you're thinking about cumming a lot more now than you were when you left the house this morning. Judging by the wet spot you made in them, you rather like being forced to be a pantyboy, don't you?"
Reading her text it took him a second to think of what to say. The idea of it would normally be emasculating and repulsing, but he was so turned on and engaged in her game that to say it didn't have him buzzing would be a lie. It was complicated set of emotions and desires to be sure.
"Yes Mistress," he relented, hoping the discussion was over.
"Yes Mistress, what?"
"Yes Mistress, it turns me on when you make me wear panties and do dirty things for you in public," he replied. Saying it made it so, and as he typed it he felt himself twitch against the soft fabric. The dull ache of unfulfilled arousal was beginning to take up residence in his balls.
"Good, because if you question something straight from the contract again, your balls will pay the price," she replied. Reading the words made his cock twitch in his pants once more.
Remembering their weekend getaway, he knew she meant business. She had tied him down and abused his balls thoroughly on that occasion. He decided it was best not to respond and instead tried to focus on getting some work done, which was now infinitely harder.
*****
The rest of the afternoon passed with little conversation between them and he surmised she must be as busy trying to get things done as he was. When he was just sitting there it was possible for him to forget his predicament for stretches of time and his arousal would ebb, but whenever he needed to get up and move around to complete a task, it would set the toy and his arousal simultaneously back into motion.
Interestingly enough as the day wore on and his sexual tension grew, the once subtle sensation of the ball rolling around in the butt plug had grown more intense. Now he felt every motion as if it were crashimg into his prostate with even the simplest of adjustments. It gave him a tingling chill of electric pleasure.
"Pick me up at 7. You're taking me to dinner," she texted him with twenty minutes left in his shift.
"What shall I wear?' he replied, unsure of just how fancy of a place she had in mind.
"A button down and tie should do nicely, and of course don't you dare think of changing out of your panties. :)"
"Of course Mistress, I will be parked out front of your office at 7 sharp."
The drive back to their house was an eventful one as the toy buried inside rolled and shook as he made his way through rush hour traffic. It was almost 5:45 pm by the time he pulled into his driveway. He hurried inside and rummaged through his closet grabbing a fresh shirt and tie from his closet and set them out.
In the bathroom he began to strip down and saw the pink panties covering his member. By this time his balls had begun to ache from his unfulfilled arousal and he wanted nothing more than to stroke himself to release. Resisting the urge, he jumped in the shower, turning the water several degrees cooler in an attempt to distract himself. He left the plug in because he didn't want to deal with the hassle of putting it back in afterwards and was certain that the silicone was waterproof.
After his shower he quickly got dressed and ran some gel through his hair. He was running out of time to get downtown and pick Allison up. Thankfully, some of the traffic had dissipated and he found himself pulling to the curb with five minutes to spare. He began fiddling with the radio while waiting for her to get out of work.
The sun was setting behind the office buildings and its bright orange glow made it hard to discern the darkened silhouettes milling about the sidewalks. There was one that emerged from the building and headed towards him, but he was unable to tell if it was her until she was a mere fifteen feet away.
Making it more difficult was the way that she was dressed. She wore a gray, knee length pencil skirt and a white dress blouse. Completing the ensemble were black pantyhose and black peep toe pumps with a modest heel, perhaps 3 inches, he couldn't be certain. Normally she wore dress pants and a nice shirt, but nothing this elaborate to work. As she opened the door directly behind the driver's seat, he realized that he hadn't blinked since she came into view.
"Good evening slaveboy," she said as she sat down.
"Good evening Mistress," he replied as if from a half waking dream. He could feel himself begin to strain against the soft panties his cock was still imprisoned in.
"Adriano's slaveboy, let's get a move on, I'm hungry," she said coolly. Putting the car in drive he looked up at the rearview mirror and their eyes met briefly. Her smoky eye shadow caught his glance and he lingered a little longer than he should have. The subtle smile on her face told him she was enjoying every minute of this.
Adriano's was a fairly nice Italian restaurant on the other side of town; it was about a twenty minute drive. He wasn't exactly sure how to get there from here, but there was no way he was going to break out the GPS on his phone at a moment like this. For a few minutes they rode in silence.
"How has your day been slaveboy?"
"Work sucked, but at least I had a pleasant distraction," he admitted with a grin.
"Me too," she said as she sunk down further in the seat. "Are you wearing your pink panties like a good little boy?" she asked seductively.
"Yes Mistress," he replied, the apprehensiveness about the idea that plagued him earlier now replaced with arousal.
"...and is that toy buried in your ass?" she asked as she spread out more in the back seat. He could swear that he smelled the sweet musk of her pussy.
"Yes Mistress," he replied as the car lurched to a stop at a red light and he could feel the ball rolling around deep inside him.
"Mmm...good," he heard her purr. He turned his neck in an attempt to see what exactly she was up to, but he hadn't even so much as caught a glimpse before she reprimanded him. "Keep your eyes on the road slaveboy!"
There was no doubt that he had seen her hand down her skirt pleasuring herself in the backseat. It was now completely dark out as the sun had finished its descent, and given her position there was very little chance anybody else could see.
"Bossing you around and owning your cock all day has made me...rather wet..." she said and he could hear her wetness as she slid one of her fingers inside, "...and unlike you, I can cum whenever I want to." The sound caused his heart to pound and he could feel a drop of precum soak into the panties. How he wished he could bury himself deep inside of her. He could feel his balls aching.
Paying attention to the road and navigating to the restaurant were the only distractions he had from how bad he wanted release. In the backseat, Allison continued to touch herself and made sure to have a very audible orgasm, just another way of teasing him, and it worked. She just smiled as she caught him staring into the mirror, trying to catch a glimpse of her.
"Open up," she said and he could feel her fingers brush past his lips. She slid them into his mouth and he tasted her musky sweet wetness.
"Mmm...fuck..." he whispered under his breath. Her taste and smell always drove him wild and right now his arousal was already in overdrive. It took a moment for him to snap back to reality and, thankful to be at their destination, found a parking spot near the restaurant. Once he got out he turned to look and noticed that Allison was still in the car. After a few seconds he opened her door and extended his hand to help her out of the car.
"Good, you are beginning to understand that you are to treat me like a queen from now on," she said, standing and stepping close to him.
"Yes Mistress."
She leaned in as if to whisper to him and instead he felt her hand lightly caress his erection through his slacks. With her other hand she grabbed his tie and pulled his mouth to her lips, kissing him deep and long. A soft moan escaped her lips as she did and he swallowed it down deep into his arousal as the kiss continued to linger and she swirled a single finger against the imprint of the head of his cock. After several seconds the sound of approaching people brought him back.
"You've been very good so far," she purred and grabbed his hand, leading him into the restaurant.
He walked behind her admiring the way that the heels made her ass sway when she walked. It was quite the sight and something he didn't often get to take in. It was rhythmic and intoxicating. He looked up just in time to see that they were approaching the door. Stepping aside quickly he grabbed it and opened it, letting her pass in front of him before following her to the maitre d.
They were led to a large booth around the corner and near the back of the restaurant. Even though it was beginning to get late, there was still quite the dinner crowd talking and drinking and enjoying their meal at a slow pace. He wasn't surprised, this restaurant always managed to do well for itself. Allison motioned for him to take a seat and to his surprise she slid into the booth next to him.
It was rather spacious and there was more than enough room for the both of them. They glanced at their menus for a few moments before their waiter appeared.
"What can I bring you to drink?" he asked.
"We'll take two glasses of the house red," she replied for them before he had a chance to answer.
"Should we really be drinking if you...ah...want to have a baby?" he asked hesitantly, unsure whether it was an appropriate question.
"It's all about balance and moderation," she said as she turned to look into his eyes, "...and besides, that's none of your concern is it, slaveboy?" she said as she firmly grasped for his balls under the table. The strain of constant arousal throughout the day had taken his toll and to say he had blue balls was an understatement. She probably hadn't grabbed him as hard as it felt like, but he couldn't help but groan softly. Looking around the restaurant not a person was the wiser.
"Yes Mistress," he winced as she cradled his balls more gently now.
"I see you're arousal has made you a bit achey," she said with a devious smile. He nodded in response. A minute later she stopped just in the nick of time as their waiter approached and handed each of them a tall glass of ruby colored wine. Allison swilled the glass before taking a sip, savoring the moment. He raised his glass to his lips and sampled it himself, it was sweet with a distinct fruity note to it, but had a definite alcohol taste on the back end. Not overly complex, but cheap, enjoyable, and very drinkable.
