The Punishment of Mary

Wednesday:

Mary awoke feeling slightly better than the day before. She felt a little better rested now that the pain was more of an ache than the sharpness of the previous night.

She did her morning rituals and got dressed for the day. She made herself some breakfast and a coffee as she contemplated what the day would bring. The not knowing was gnawing at her. If she knew what Mr. Brenner had planned it would be easier to prepare herself and handle it, but the uncertainty made it so much worse. Would today be a gentle pleasurable day? Or a pain filled nightmare? The not knowing was tough.

'Nothing for it' she thought. 'I made this bed and now I've gotta see this through. Worrying won't make it any easier'. With this thought in mind she got in her car and went to work.

The day was once again filled with the normal mundane tasks she always did. She still sat a bit gingerly but it wasn't as bad as yesterday. At the end of the workday she once again reported to Mr. Brenner's office.

As before Greg was watching the monitors until the last of the employee's left before indicating Mary should get undressed. After she was naked she got into the position he seemed to enjoy. He smiled at her automatic response.

"Very good slave. You are learning how to please me already." He said.

Greg walked over and once again examined his handiwork. The bruises were beginning to fade slightly but were still very much visible.

"How is your training of your ass going slave?" Greg asked.

"I'm not sure Master. I've been wearing the buttplug as you requested and it feels almost natural Master. I believe it's going well."

"I'm glad to hear it. I'm not going to test it today. I have a different plan. I might decide to do it tomorrow though." He spoke as he removed his pants and sat on a chair in front of his desk.

"Come over here and use your mouth to get me hard." He commanded.

Mary moved to do so. She knelt in front of him and began licking his half hard cock. As it began to harden and lengthen she took the head into her mouth. Using her tongue to tease the shaft she drew his dick further into her mouth. Using all the skill she had before coming here and the few things she had found he liked she tried to bring him up quickly, but once he was hard he pulled her off.

"I know how good you are at blowjobs but that's not what I want today. Today I'm going to put that beautiful bosom to good use." He said.

He grabbed a bottle of lube off his desk that he had placed there earlier. He drizzled lube into her cleavage making sure to get it well into the crack. Replacing the lid, he placed the bottle back on his desk.

"Now I'm going to sit here and you are going to give me a tit fuck. Do a good job and today will be easy. But take too long and I may need to amuse myself in other ways. Make sure to use that talented mouth as well." Greg said with a smile. It wasn't a friendly smile.

"Yes Master." Mary said.

She straightened up while still on her knees and leaned forward so she could wrap her tits around his saliva slick cock. With her saliva and the lube his dick slid fairly easily within her titflesh. She started sliding it up and down while making sure to lick and suck the head whenever it made an appearance out the top. She stroked him with good sure strokes and rhythm. Greg was in heaven. The stroking between her amazing tits and the periodic licks and sucks were driving him wild. He began to feel that familiar pull in his balls and just before he came he pulled back slightly and stroking himself he aimed his load at her face and let loose. She was surprised but took it like a champ. Allowing herself to be covered in his seed and awaiting his next command.

Greg took a moment to regain his composure before telling her, "use your tongue and fingers to clean yourself up."

He watched as she used her fingers to gather up his cum and suck it into her mouth. He thoroughly enjoyed the sight. Mary was used to the taste by now and didn't mind it. When she got most of it off her face Greg told her to clean his dick again. She took his softening member into her mouth and gave it a good tongue bath.

"Alright, looks like times up for today. You did a really good job. You can use the bathroom to clean up again and I'll see you tomorrow. Good night slave." Greg said as he dismissed her.

"Thank you Master." Mary said, knowing he enjoyed her gratitude and wanting to keep him happy.

Mary once again grabbed her clothes and retreated to the bathroom to clean off the remaining cum and get dressed. Then she left and got in her car to head home.

'Today wasn't bad. A little degrading maybe but at least it wasn't painful. Although it sounds like tomorrow may be the day he takes my anal cherry. I'm not looking forward to that. Hopefully wearing this thing in my ass has at least stretched or trained it enough to handle him. I guess I don't have a choice though.' She thought as she drove home.

Mary once again changed into some loose fitting clothes as she got home and made dinner. She took another hot bath to soothe her aches and was feeling better as she got ready for bed. She tried to think happy thoughts as she drifted off to sleep.