Ryley’s list included just five items. He expected more but was relieved to find that she wasn’t asking for too much. That would make obtaining her desires much easier. Dr. Connor loaded his online shopping cart with two boxes of protective face masks, four bottles of surgical lube, a box of medical tape, a couple of metal syringes, and a speculum. Before he could overthink it, he checked out and closed out of his browser. Ryley’s supplies would come in the day before he was expected back in her playroom.
It had only been three days since his last encounter with Ryley, and while he was used to getting off much less than twice a week, his balls were aching for release. The chastity device pushed uncomfortably against his zipper, always reminding him of its presence. He felt like everyone could see the bulge it created in his scrubs and tried to stay seated as much as possible while at the clinic.
Two nights before, Sunday night, he had sent a short text to Ryley. He simply stated that she was on his mind. The app notified him that it had been read, but he got no reply. He couldn’t stop thinking about her slender, elegant fingers – three knuckles deep in his ass. He could feel his cock pushing against the cage and decided that he needed a distraction.
Taking an early lunch, Dr. Connor drove up to the canyon and climbed over the railing. He had been coming here since he was a teenager and the view gave him peace of mind that he couldn’t find elsewhere. Taking a deep breath, he centered his thoughts on his practice and tried to keep his focus there. Despite his years of meditation and his steel-like control over his mind, his thoughts kept wandering back to Ryley.
What is she up to? Does she have other clients? Why does she need him to order her medical supplies? Is he the first doctor she has ever blackmailed? Is he the only doctor she is currently blackmailing? How did she make him so weak?
He could feel his cock really straining against his cage again. Sighing, he pushed himself off the ground and paced up and down the cliff’s edge. Lost deep in thought, desperately trying to keep the sexual desires at bay, he didn’t hear his phone going off in the car. He spent an hour out on the edge, trying to calm his thoughts and bring himself back to reality.
After an hour of failing, he climbed back over the railing and into his car. He drove back to the office before even thinking about his phone. When he checked it he had two messages from Ryley. He held his breath as he opened them, surprised that she had thought of his at all.
Have you ordered my items yet?
Please do not contact me first. Ever.
His excitement was quickly diminished by her apparent annoyance, but he typed out a reply anyway. He stated that he had ordered her items and they will be here in time for their next “date” and that he understood not to contact her first. He tucked his phone into the pocket of his scrubs and went about his day.
When Dr. Connor got home Friday, a package was waiting on his front porch. He quickly put it in the trunk of his car and went inside the house. He had spent all week in an almost constant state of arousal. Saturday could not get here quickly enough, it was only fifteen hours away, but it felt like light-years.
Connor made himself dinner and flipped through TV channels for a few hours before heading off to bed. There wasn’t anything good on, dinner tasted bland, and the anticipation for the following morning was causing him to feel nauseous. He tossed and turned all night, and when he did sleep, he dreamed of being strapped to a table with a dildo in his ass. He woke up more than once with his cock straining against the chastity device, desperate for release.
Saturday morning he was up at 5 am, making coffee and pacing around the kitchen. Despite his lack of sleep, he was wide awake. When the coffee was done, he downed the entire pot within an hour. Leaving him with another hour and a half before he was due at Ryleys. With too much energy, he headed off to the gym. He figured that he could at least get in a workout and that would make the time fly by.
Before he knew it it was 7:45 am and he was drying off from a heavy workout. He was sure that the cock cage was visible the entire time he was lifting weights and was thankful that the gym was empty that early on a Saturday morning. Once he was fully dressed again, Connor left the gym and headed towards Ryleys.
It was a short drive and he arrived with just a few minutes left before his appointment with her. He unloaded the package before knocking on her door and then waited patiently for her to answer.
Ryley answered wearing a robe, her hair was up in a messy bun, but her makeup was impeccable. The sight of her took his breath away and the blood rushed to his groin. He stifled a groan and greeted her.
“Good morning Dr. Connor,” Ryley crooned. She offered him a smile and he noticed a slight commotion behind her. She invited him in and he noticed a naked man making breakfast in the kitchen. “Don’t pay any attention to Philip. I called him over last night and we fell asleep.” She laughed, a knowing look in her eyes.
Connor hadn’t considered that she had lovers or even that she had sex! He just assumed that she teased men and pleased herself. Jealousy welled up inside of him. What made him so undeserving of her caring touch? Why was he just a toy while she slept in the arms of Philip? He pushed the thoughts aside. He had agreed to this arrangement. He knew he could have any woman he wanted, but he got something from his relationship with Ryley that he wouldn’t get elsewhere. While he completely wanted to participate in these things, he felt like he was made to submit and that excited him more than any relationship he had ever been in.
“You can set the box over there,” Ryley’s voice interrupted his thoughts. She was sitting on the love seat, pointing at the entrance to the hallway. “I wanted to talk to you about something this morning.” She continued as he unloaded his burden and sat across from her on the couch. Her legs were parted a bit and Connor could see up her supple, waxed lips. He forced himself to look up from her vagina and into her eyes, a devious grin sat on her lips.
Once he was settled she produced a sheet of paper and began, “Since you have agreed to supply me with medical supplies, and came through on my first order, I would like to discuss the legal side of this before we have another session.” Connor squirmed on the couch. “This is a contract that states you give consent for any activities that we explore together, there is a place to list hard limits that I will agree not to cross. It also states that you will provide me with anything I ask in exchange for weekly,” she paused and that devious grin returned “play dates. Do you agree to these terms?” She handed the paper over to him and encouraged him to read it.
The contract stated exactly what she had just explained, and as far as he could tell there were no loopholes or fine print that would cause him problems in the future. Ryley handed him a pen and he wrote out his hard limits and signed the paper, without saying a word. He handed it back to her and she asked if he had any questions.
He thought for a moment before stating, “I suppose we should settle on a weekly budget.”
“That was outlined in the paperwork.” Ryley stated, before briefly glancing over the paper, then huffing, and saying, “I suppose it wasn’t. I will require bank statements from the last six months. I will not require any items this upcoming week, so you are off the hook for that. But next Saturday I expect those bank statements. I will work out a budget for you and then we can discuss a weekly maximum spending level.”
He hadn’t expected her to be so forthcoming and business-like. He had waited this entire week for her to play with him and so far all they had done was chat about legal stuff. While his dick was calm, his mind was racing, knowing that her playroom was only a couple of yards away. He glanced down the hallway and suppressed a sigh.
Ryley noticed and stood up. “Are you ready?” She asked. Connor stood up, retrieved the box of requested equipment, and followed her to the playroom. It looked exactly as it had last week – expect there were new instruments on the table. Ryley instructed Connor to open the box and she stored the items in her various cabinets and shelves. Expect the speculum, she placed the speculum on the table beside the restraint bed. While she did this, Dr. Connor undressed and arranged himself onto the table.
This time Ryley instructed Connor on how to strap his legs into the stirrups and then she slightly worked on restraining the rest of his body. While she tightened each strap and ran her nails down his muscles, he could hear Philip rummaging around in the kitchen. Knowing that someone who had pleased his mistress could hear his moans made him even more anxious.
Ryley finished restraining Dr. Connor and continued running her nails across his body. Giggling as goosebumps rose across his flesh. She made her way to his groin and teased his cock between the bars of his cage. She laughed as he strained against his restraints, his cock filling with blood. She reached behind her and retrieved a key from the table, unlocking his cock, he moaned as it sprang free. He wasn’t aware that he could be so hard and so desperate.
Using just her nails, Ryley gently ran them down his cock. Dr. Connor knew that Philip could hear him groan as he attempted to arch his back, silently begging for more. She did this a few more times before completely enveloping his cock in her hand. Slowly, agonizingly, stroking his cock until he was covered in precum. Without her saying so, he knew that cumming without her permission would result in punishment.
His cock ached for release, his lip was throbbing from him digging his teeth into it, trying to keep control over his orgasm. Connor almost lost it when he felt Ryley’s tongue run up the length of his member. He never expected her to use his mouth and a pathetic “please” escaped his lips without him realizing it.
He could hear the musical sound of her laughter, but it felt like she was far away. Everything was echoing and dimmed. He was on the brink of the strongest orgasm he had ever had in his life. His entire body prayed for release. The restraints left imprints on his arms and legs as he pushed against them.
“Do you want to cum?” Ryley’s voice came from somewhere in the distance.
“Yes, Mistress Ryley,” his own voice sounded foreign and feeble to his ears. He had never been so hopeless for release in his life.
Ryley continued to stroke Connor’s cock, not gracing him again with her tongue or mouth. “Count the strokes, you can come when I get to 10,” she instructed, gently. She continued slowly pumping his cock as he counted, each number sounding more helpless than the last.
Before the number ten was even past his lips his cock erupted. Sticky, hot, white cum shot up to his lips. He could taste the salty semen on his tongue, and his eyes rolled back into his head. His cock shot out six strings before it resorted to merely twitching under Ryley’s hand. She continued stroking as he came and he moaned louder than he had ever in his lifetime.
Even though he had just finished, and his cock was tender, Ryley continued to stroke him. He tried to scramble away from her, but his restraints held him firmly in place.
“I want you to count to 20 this time. And when you get there, I want you to cum again,” Ryley sounded closer this time, but he was having trouble focusing on her instructions. He gasped as two slender fingers found their way into his ass and began kneading his prostate. It wasn’t the rough play session he had fantasized about, but he was grateful for the release. He began counting again and was surprised to find himself nearing orgasm again.
This time his stream was weaker and he only twitched a bit before it was over. Ryley quit stroking him when his cock went still in her hand and tossed a wet wipe onto his chest. She undid his top restraints and instructed him to clean himself off. He did so before she allowed him to undo his legs.
When Connor tried to get up off the table he found that his legs were weak and he had trouble standing. He leaned against the table, closed his eyes and took a moment to collect himself and allow blood to redistribute itself throughout his body before trying again. When he lifted his head, Ryley was no longer in the room.
Dr. Connor dressed and wandered through the house. He found Philip had set the table with three plates, but that Ryley was nowhere to be found. Philip explained that she was in the shower and that Connor was expected to stay for breakfast.
He arranged himself at the table while Philip brought a platter of eggs, bacon, gravy and biscuits, and various fruits into the dining room. As Philip finished placing the food on the table, Ryley emerged from another room. Her hair was still in a messy bun, but she was dressed in yoga pants and a form-fitting racerback tank top. Her nipples strained against the fabric and Connor had to drag his eyes up to meet hers.
“I thought you could use some nutrients after our last play date,” she winked at Connor before turning her attention to the food. The three of them made their plates in silence before Ryley spoke again. “Our sessions won’t always end like that, even if you do please me. This week I’m going to leave you out of chastity, but you are only to touch yourself when I instruct you to. When I do send you instructions you are to stop what you’re doing, unless you’re with a patient of course, and follow them immediately.”
With the fork halfway to his mouth, Connor froze. He hadn’t expected her to impede on his weekly life – besides the chastity and little to no communication. While he did think about her often while they were apart, he had no idea it would affect him much outside of her playroom. Ryley cleared her throat and Connor had to blink rapidly a few times before he was able to reply.
“Yes, mistress,” was all he could muster. Ryley smiled and they finished breakfast like old friends. Talking about work, books, and other non-sexual topics. No matter how hard he tried to concentrate on the topics at hand, Connor’s mind kept going back to the fact that she would be in contact with him this week. She could control his cock and orgasms outside of her playroom. This week was going to be even more difficult.
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