The Adjustment - Rupert and Tamera

Chapter 8

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Tamera and Rupert lay on the bed enjoying the afterglow. Tamera could have an orgasm when she performed blowjobs on Rupert. She just had several and was soaking wet. Her new panties were wet. Rupert had put his robe back on before he laid down. Tamera had only taken her high heels off to lay down.

She broke the silence and said. "We still have one more thing to do tonight. It's time for your upgrade."

Rupert knew it was coming. After what Tamera had just done for him he knew he was as relaxed as he could be. Tamera got off the bed and went into the master closet. She opened a drawer and pulled out the box. The lube and medical gloves were in there too. She went to the bathroom, filled a large cup with hot water and put the lube in to heat up. She came back into the bedroom. We will give that about ten minutes. Rupert said nothing. He was back in submissive mode. Do as she says, time. Tamera laid back down beside Rupert.

Enough time passed and Tamera went to the bathroom and retrieved the glove, the box and the warmed lube. "Ok ass boy, let's do this. You've had an amazing blowjob and I don't want to take anything from that. But this is necessary to get that ass ready, properly trained."

Rupert wondered what that meant. So far he understood it was just ass plugs. What else could she be talking about? Rupert stood up.

"Want me in the corner?" Rupert asked.

"Not necessary. You can lay over the end of bed and I'll raise your ass up. That should help you relax and take this big boy. Actually it's not much bigger, the trainer is one inch circumference and this one is one inch and a half diameter. It's also about a half inch longer. Has a longer run time too. I understand your ass will know it though. But you will get use to it just as you did with the trainer. Lay over the bed ass-boy."

Rupert positioned over the foot of the bed. Tamera pushed apart his legs. She had the bed remote in her hand and lifted him up.  Rupert had been in this position before many times when he got spanked weekly. Usually it was the last round and on his bare ass.

"There, relaxed? Address me properly." Tamera said.

"Yes mamn." Rupert nervously responded.

Tamera squirted the lube on her glove. She spread the warm paste over his hole. She reloaded her fingers with a generous amount of goo this time. She piled it on his anus, then pressed as much as she could inside. Using two fingers she pushed and twisted as deep as she could.

"We gonna need a lot of this the instructions say."

That didn't help Rupert relax. He anticipated a much fuller feeling than the trainer. The other plug was uncomfortable, this one sounded a lot worse. It's 50% bigger, he thought. And a longer run time. Rupert moaned when Tamera applied a third application.

"We gonna need a another tube of this by next week. Maybe I can find a better applicator."

Tamera let Rupert relax a bit before she opened the box and pulled out the larger plug. "It don't look THAT much bigger. I think you can handle it, you are a good ass-boy." Tamera patted his ass. "Here we go. Couple deep breaths." Tamera was in her Dom mode and expected Rupert to be in his Sub mode. "It's time for you to ask me properly and with respect to ass-train you, boy." Tamera giggled after she said it. Tamera placed the plug at his entrance and rested it there, waiting on Rupert to ask for it.

"Please mamn, put the new big wonderful toy in my ass so I may be properly trained to be the best ass-boy possible. I am your ass slave to please you."

"You are getting good at putting it on thick. I like it. Total submission. Good boy."

Tamera pressed the tip of the plug on his anus, pushed more and slipped it completely in. Rupert moaned and forced his head into a pillow. "Raise your head boy. Show how brave you are." Rupert raised his head and looked forward. His back arched a little. "I love that pose boy. You look so submissive. I like it." Tamera tugged a bit on the handle, twisted a little and made it settle in. "Now, I'll get my phone. Let's see what this baby can do." Tamera just seemed to giddy. "I found a web site that has dozens of new patterns. I've got six more downloaded. Let's try them all!" Tamera was excited. Rupert not so much.

Rupert laid still waiting for permission to get up. He needed underwear too. Tamera took off her rubber glove, wiped her hands and put the lube and tin box back in the drawer in the master closet. She got Rupert some underwear and tossed them on the bed. She wet a towel in the bathroom and came back to wipe the excess lube around Rupert ass.

When she finished she said, "Lets go to the living room and start a movie. Put those underwear on and come with me."

Rupert slid off the bed. The new plug did feel much larger and filled him up a lot more. Two hours of this was going to be a challenge. And she hadn't even turned it on yet! Rupert carefully pulled up his underwear. He had a soft erection too.

"Almost recovered, huh?" Tamera noticed the partial erection. "Maybe we can have round two later, after the ass-training of course." Tamera snickered and left the room.

Rupert followed Tamera to the TV room. He sat down gently in his recliner. He leaned forward in the chair, letting the butt plug settle in his ass. Slowly he leaned back and lifted the foot rest. He pushed into the back of the chair and looked over at Tamera. She was smiling with a broad grin on her face, watching him settle in.

"You ok babe?" She knew he wasn't but still enjoyed his struggle. She knew he would lie to her and not complain. It would do no good either. In her Dom mode she never had mercy. She would get what she always wanted anyway. Control and submission. She would accept nothing less except full corporation from Rupert. "I'm ok. I want to please you." He was far from ok.

Tamera searched her saved movie list.  It was not going to matter to Rupert what she picked.  His level of attention to the movie would be near zero once she cranked that thing up in his ass.  If the trainer shook his guts, this damn thing could shake his entire body.  Tamera picked a movie.  A drama bank heist plot. Rupert liked those but he likely would have to rewatch it another time.  If there ever was a time where he didn't have something stuffed in his butt. 

It was day four in a row of being violated in the ass.  Tamera didn't exactly say how long this training would last.  She didn't even offer the ultimate goal of ass training either.  She did once say that in two weeks he would be glad his ass was trained.  Good grief he thought, what happens after two weeks?