It was all his fault.
All he had to do was pick a female from his phone contacts and have them call his Mistress. He missed the deadline and in turn his Mistress used his email account to send a message to his doctor asking her to see him due to his concerns over locking himself in chastity and practicing orgasm denial for extended periods of time. Although covered by patient privacy, she was his family doctor for most of his life and would have to endure the prospect that she knew of his kinky secret.
In a state of panic he asked an ex-girlfriend to call his Mistress. They had dated in college and he remembered her being really good in bed and very open minded, but eventually he broke up with her for being too clingy and controlling. However, that was years ago and she seemed to have matured since then. He had, coincidentally, run into her a couple of months ago and they had seen each other on and off since. Lunch, dinner or maybe a movie, but nothing more.
That was until he asked her for help. She told him that he owed him big time. He reluctantly agreed, knowing that now, two women had him trapped. She thought it was funny that he placed himself in such predicament and jokingly let him know it. Her request was not, he thought, so funny. She wanted him to clean her house once a week for the next six months to which he agreed.
Then she added the caveat that he needed to do it naked. When he began to waffle, she asked him what his Mistress would think if he reneged on his end of their bargain. She chuckled at the prospect of having him clean up for her and seeing what a chastity cage looked like.
To make matters worse his Mistress had one more punishment for him. For the next six weeks he was to blindfold himself and wait for her naked. She would then handcuff him, unlock him, clean him, wait for him to go soft and then lock him back up. All without speaking to him. It was maddening. Now more than wanting to cum, he just wanted to be teased. Her ignoring him was more than she could bear.
Twenty-six weeks. A full six months. He was going mad. He had not see or heard his Mistress speak for over six weeks. She would simply contact him via text messages. His cock ached for release, for her touch, for anything. He didn't know if he could go on. His frustration now gave way to desperation. He was on the verge of breaking down.
He talked to his ex-girlfriend about it. She told him he was silly for getting into such a predicament, but he had either end it or see it through. Shit or get of the pot she would tell him. Just don't whine about it.
They had become more and more of a platonic couple the more he went over to her place to fulfill his debt to her. She had become quite comfortable with him being around her. Having taken to walking around in her panties when he was there and slowly starting to have him helping with other chores such as running errands or going shopping for her. He began to think she was playing games with him, taking advantage of his situation, but he dismissed this as crazy thoughts of a sex starved submissive.
In the absence of his Mistress he was growing fonder of her and began getting aroused just at the thought of going over to her place and see her. He began to think that it was a mistake to break up with her.
Out of nowhere, he received a message from his Mistress on his way over to do his weekly cleaning. He almost drove off the road as he read the message. He thought about it as he drove to her house. He decided that his girlfriend needed to see the message for herself. He just didn't know what to do anymore. He couldn't think straight. She would help, she has before.
She read the message as he got undressed. "Umph. She's got a point. This would definitely prove your devotion and your commitment to your key holder." She put the phone down. "Have you done anything like this before?"
"NO! Never. I mean my doctor told me it would it help, but I mean really!"
"Well, It seems and no pun intended, she got you by the balls. I mean if you stand your ground you could lose your job. I'm not sure your boss would appreciate you letting her in on your little secret." She could clearly see he was gripped by fear and indecicion. "Look, I'll help you do this, but if I do this I'll need to revise our arrangement."
"Yes, of course. Fine." He was blindly over zealous. His Mistress was ready to cost him his job. A great job as a matter of fact. She told him that she were to help then she would like to extend his obligation another six months. She also wanted him to service her orally at least twice a week for that time. He prided himself on his pussy eating skills and eagerly jumped at the chance to prove it. He was to clean the house and she went out to get the things they would need to accomplish his task.
She returned a while later and he was just finishing his chores. After she had him shower; she had him fix them a couple of drinks and join her in the living room. "Kneel." she commanded as he put the drinks down.
She slipped off her skirt and stepped towards him. Her crotch almost on his nose. "Sniff it. Do you remember how good it tasted?" He took in her scent and moaned as he nodded yes. His cock stirred in its cage.
She inched towards him, the dampness of her panties tickled his nose. "Use your tongue." He stuck it out and pressed it against the fabric. She cooed softly as he worked it around. Soon her hands were winding their way through his hair. His mouth was now pressed against her as he sucked and licked her through her panties.
"Take them off." she hissed. "With your teeth." By now he was dripping pre-cum on the floor beneath him and his neglected member ached for release. As he slowly worked them down, her well groomed crotch revealed itself. An arrow of hair pointing directly to her moist mound caused a painful swelling in his cage. She pulled him by the hair into her as she fell back onto the couch.
Lustfully he dove right in. Her scent filing his nostrils. She bucked and moaned as he worked his tongue between the folds of flesh. She pushed her feet into his back and her hands pulled at his hair as she was driven closer and closer to climax. He moved in for the kill and her shriek pierced the air as she was seized by her orgasm.
"Wow. I'd forgotten how good you were." She sat up after a few minutes, resting, catching her breath. "Now let's get you ready. Turn around." Hesitantly, he spun around on all fours. She giggled at the slick puddle on the floor. "Is there anything left? Well, lets find out. OK. Face down, ass up."
She hung a small cup off of his chastity device. A wave of embarrassment and humiliation swept over him as he felt the cool lube slide down his ass crack. Without warning she slid a finger into him. His ass puckered tight around it. Her invasion was just an attempt to lube him completely. "How's it feel, Honey?"
"OK, I guess." He jumped though when she brushed over his prostate.
"Jackpot." she said whimsically.
She withdrew her finger and readied a prostate massager. Slightly angled and bulbous with a handle and an arm to stimulate from the exterior as well. Gently placing it on his ass she pushed it in. She smiled as she watched it slowly disappear. He gasped as it hit its mark. "Are you OK?"
"Yeah, all things considered." She began alternating between moving it in and out and rocking it back and forth, judging his reactions for the best technique. His cock futilely stiffened in its confines. He wondered if if was supposed to be getting aroused by this. "Oh, yes. Tweets. Please." was a barely audible hiss that escaped him. He hadn't even realized what he'd said or that he'd started rocking back and forth.
She was surprised also at his response. 'Tweets' was his pet name for her when they had dated. "You can do it, Honey." She whispered back. "Fill up the cup. Relax and fill it up."
He bit his lip as he felt the pressure of an orgasm build inside him. 'Almost there.' he thought. Like the pressure of a shaken bottle of soda, he just needed to pull the tab. "Please, oh, please." He pushed back harder. "Almost!" he grunted. "There!" He started panting. He tried to will himself over the edge.
It was hopeless. He wanted to scream. "Please. Let me cum. Please!" He collapsed to his elbows and his head hit the floor.
""All done." She pulled out the probe from him and took the cup off his cage. "My, my, look at what you did!"
He turned to see the cup was almost full of a milky white fluid. His fluid. His cum! She took off the wires that held it to his cage and screwed on the cap. "Here you go." She held out the cup. "You should clean up and get going."
He did as she asked and soon he was on the road. Headed towards his Mistress.