A/N: I highly recommend reading the first part of this story titled "The Weekend Getaway - Friday" so that you can be informed of the situations, scenarios, and characters featured in this chapter. Feedback and ideas are much welcomed and thank you for reading!
*****
It was shortly after seven on Saturday morning and the first rays of sunlight had begun to filter through the blinds. Brian had been laying there awake for almost an hour now after having given up on getting any more sleep. It was a night of tossing and turning. His wife Allison lay next to him, soundly asleep and ignorant of his struggles.
She had surprised him with this little vacation and its subsequent eroticism. She had teased him mercilessly in order to test his mettle the night before and wouldn't allow him to cum. Despite his assurances that he wouldn't violate her trust and ruin their little game, she had forced him to sleep in some sort of bondage shorts. They were made out of leather and strapped down fairly tightly around his waist and legs and of course locked. On the front was a small pouch where his cock rested and could easily be accessed, but it too was secured with a small lock, the key to which was secured to a necklace she always wore.
The shorts weren't altogether uncomfortable unless he began to get hard, which unfortunately had been an ongoing problem throughout the night. Just as soon as he would lay his head down on the pillow and calm his mind enough to drift off to sleep, it would begin to wander and reflect on all of the sexy things that had transpired just hours earlier and dream of all the possibilities yet to come. Soon enough he would wake up, his half erect cock straining uncomfortably against the tight shorts and unable to grow anymore, only to repeat the cycle and try once more to fall asleep. He was a prisoner of his own teased mind.
He turned towards his wife and wrapped his arm around her in an embrace. There was a small part of him that hoped that this gesture might stir her from her sleep. With one hand he lightly ran it up and down her back caressing her softly and was delighted to see that her eyes had opened slightly.
"Good morning, slaveboy," she said stifling a yawn.
"Good morning."
"How was your night?"
"Honestly...terrible,"
"Why do you say that?" she turned her head slightly so she could catch a glimpse of him. "We've got this comfy king size bed, a beautiful room, the sound of the waves..."
"Easy for you to say, you're not the one being woken every half hour because you're uncomfortable," he said disdainfully.
"Was it hard for you to stay asleep?" she asked with a big smile, her eyes fully open now. She slid one of her soft pedicured soles up and down his leg suggestively. Between that and the feel of her soft silky pajamas against his chest he could feel his cock beginning to stir yet again. He could feel her hand make its way to his crotch, trying to cop a feel through the heavy leather shorts.
"That's an understatement," he replied.
"Well that's just too bad...because slaveboys like you can't be trusted not to cum." she said with a taunting air in her voice. She continued to torment him with her feet for a few minutes before moving her body back further on the bed so that her shapely round ass rested against his crotch. She rocked her hips subtly, grinding against him. "I can feel your cock straining against those shorts...I bet you wish it was free don't you?"
"Yes."
"Yes what?"
"Yes Mistress," he added after a few seconds of waiting. She was fully awake now and sat up on the side of the bed.
"I'm willing to unlock you, but you better not touch that cock of yours without my permission and you better do as I say..." she said as she played with the key around her neck waiting for his response, "...that is if you want to be allowed to cum."
"Yes Mistress, I understand." he replied. She removed the key from around her neck and unlocked the shorts, pulling them off of him. His cock sprang out at once and began to stiffen, glad to be free from its confines and able to breathe once more. There was nothing he wanted more than to reach down and stroke it, but he knew better. She was watching him, seeing what he would do, he could tell she was very much still testing him.
*****
A few hours had passed and he still wasn't sure what to expect from Allison other than more teasing. Breakfast was delivered via room service shortly after they woke up and consisted of homemade waffles, fresh cut fruit, bacon and coffee. They ate it together on their balcony and watched the sun finish rising. Afterwards they took a shower together. She made him take his time and wash every inch of her body, a task which made his cock stand at attention the whole time. She found this amusing and proceeded to stroke his cock from time to time, claiming it was only fair since he got to touch her.
After their shower and before they got dressed for the day, she had told him that she had another surprise for him. He sat down on the bed while she rummaged through her duffle bag looking for something and emerged a minute later holding a large metallic object. One end had what looked like to be a cock ring on it, and the other looked like some sort of rounded butt plug. It wasn't too large, but he wasn't entirely sure what to make of it.
"What is that?" he asked apprehensively.
"It's what is going to help me keep you in line today on our little adventure," she replied as she picked up a bottle of lube and joined him on the bed. She carefully fed his cock and balls through the cock ring portion of the device. It was cold from having been in the bag on the floor all night, but the way it wrapped around his balls and squeezed his member felt good. She squirted a generous portion of lube onto the other part of the toy and looked up at him. "Do you want me to put it in your ass, or would you like to do the honors?"
"I'll do it," he replied. He wasn't exactly a stranger to having toys in his ass and enjoyed the sensation of having his prostate played with, but it felt better to at least be in control of easing the toy in himself. He felt the cold metal toy press against his opening, and with a bit of steady pressure it slowly worked its way in and disappeared. It wasn't uncomfortable at all and he could hardly feel it in him when he sat back down on the bed.
"All set? Good, why don't you go ahead and get dressed then?" she prompted and he looked over to see that she had laid out a pair of shorts and a t-shirt on the bed for him. When he stood up and walked around he could feel the subtle movements of the toy in his ass and it felt good, much better than when he had been sitting still. Whenever there was movement of his cock or balls he could feel it translate into small movements and vibrations deep inside him against his prostate.
"That's kind of nice," he said as he pulled the t-shirt over his head.
"I thought you might like it," she said as she finished securing her hair in a ponytail and began to get dressed. She donned a casual looking blue sundress that came down a little ways past her knees and grabbed a pair of simple ballet flats out of her bag. "It has a few more surprises," she added as she picked up her phone off the dresser.
"Oh?"
"I'm glad you asked," she said as she tapped the screen. He felt the faintest vibrating sensation begin in his ass near his prostate and work its way up to the base of his cock. She could tell that she had his attention because he stopped tying his shoes and looked up at her immediately. She tapped her phone again and the intensity of the vibrations grew stronger, "do you like that slave boy?"
"Damn..." he uttered, "I've never felt anything like it." It was the truth, the sensation was precise and subtle, but definitely hitting his prostate and resonating through his balls and out to the base of his cock, which was getting harder by the second. It was a very different feeling and he wasn't certain he could ever cum from it, but it was intense all the same.
"That's just the beginning..." she smirked as she turned it up a few more notches and the vibration grew vastly more intense. He was looking at her eyes, but from his vacant stare she could tell that he was lost in the sensation. She tapped her phone once more and the constant vibration instead changed to a rhythmic pulsing sensation that ran through him sequentially. It was almost as if she was milking him.
"Jesus...oh God..." he stammered letting out a sigh. Losing his balance he backed into the bed, using it to stabilize himself before sitting down on it. His breathing started to hasten along with the intense pleasure deep inside him.
"Now, now slaveboy, let's not get too worked up just yet," she teased and pressed another button. The moment she did, he jumped as a sharp painful sensation ripped through the entire region of his genitals, as if it came from inside him.
"What the fuck was that?!" he said startled.
"Watch your language boy toy," she mock scolded him and repeated the painful jolt. He winced and looked at her, still waiting for an answer. "This is what is going to help me make sure you follow the rules, it works via electrical stimulation, there are settings for pleasure and settings for punishment, which is what you just observed."
He was dumbfounded. He never knew such a thing existed. They exited their room and made their way to the car. With each step the toy made its presence known to him and drew his attention back to his pressing need for relief. As they walked past the front desk he felt his heart leap into his throat, worried that somehow the receptionist would know what they were up to or was somehow aware of his current predicament. His fears were eased when she uneventfully wished them a good day and they made their way to the car.
Walking around the car he unlocked it and took the driver seat. As soon as he sat down he felt the painful sting of punishment once more and looked up to see Allison still standing on the other side of the car. She motioned with her hand for him to come join her.
"Don't forget your manners slaveboy," she scolded him as he got out and walked around to open her car door for her. "That's better," she said with a smile as she sat down and he once again took his seat and started the engine. This was going to be a long day he thought to himself.