Kenny Pays His Debt to Society -- Part 11


by Jason A. Andresen

"You're familiar with the plug already, right Wilkes?" Rivers said as he returned the _d_i_l_d_o_ to the plastic bag and pulled out a large butt plug.

"Yes, Guard Rivers," Wilkes answered. And he was quite familiar with it. He had seen it inserted up his former roommate's butt on several occasions. He, himself, had experienced it only once.

Kenny had never seen such a device. It was like the _d_i_l_d_o_ Rivers had just forced up his butt in many ways but with a narrow 'neck' near the base which itself was flared. Rivers set the plug on the desk standing upright, resting on its wide base. It didn't take Kenny long to imagine why it was shaped like it was. The main portion of the plug fit up through the anus and up into the rectum. It was about the size of a _d_i_l_d_o_, may one and a half inches in diameter flaring out from the tip. Unlike a _d_i_l_d_o_, however, these was a narrow neck near the base. When inserted, the neck rested in the anal collar with the anus tightly closed around it. The flared base prevented the entire plug from being pulled up into the rectum. The narrow neck required that it be expelled by "_s_h_i_t_ting" it out -- usually requiring some effort.

As he had with the _d_i_l_d_o_, Rivers opend a sealed rubber and unrolled it over the plug, leaving only the base uncovered. "I'll paddle you with this in place in payment for your smart-ass remark earlier, Wilkes," Rivers said as he held the plus by its base. "Too bad these rubbers are pre-lubricated. I'd like to pound this up your asshole without any help from lubricant, Wilkes. You got a smart-ass mouth, you know. We'll just see how samrt you feel in a few minutes, though. Not too smart I'll bet. You sure won't look smart with this sticking out of you butt." Ashton chuckled as he listened to Rivers.

"Just take your pants down and assume the position on you bunk." Rivers said. Wilkes lowered his underwear quickly and started to turn. He wasn't fast enough; Aston saw his partial erection.

"Well, well, Wilkes," Ashton said. "Hold it a second. Turn back around so Guard Rivers can see." Wilkes slowly turned. "What have we here? You all excited about this, Wilkes?"

"I think I'm seeing a hard-on," Rivers said. "But I can't be sure. Is that the Wilkes version of a hard-on on, Wilkes?"

"No, Guard Rivers," Wilkes said turning red.

"You mean you walk around all day like that? No, can't be. I've seen you in the showers and the locker room, Wilkes. You usually got a much smaller peter than that. So that must be a Wilkes hard-on. Sort-of in between a Wiles 'softy' and a normal hard-on." Wilkes was trying hard not to let this get to him.

"Or," Ashton said, "maybe it's what's left of a normal hard-on. In which case that means Wilkes here had a hard-on while watchin' his roomie here get his plump butt switched. Is that the case Wilkes?" Wilkes didn't have a chance to answer.

"Or," Rivers said, "it means he's in the process of gettin' a normal hard-on thinking about the plug about to be shoved up his butt. Is that it Wilkes?" Wilkes said nothing.

"Well, Wilkes," Ashton said, "which is it? You comin' from or goin' to a hard-on?" Wilkes still said nothing. It was a lose-lose situation for him no matter how he answered.

"We could have roomie Bronson turn around, drop his pants, maybe even bend over and show his butt. Then we could see if that Wilkes-style hard-on gets any bigger," Rivers suggested.

"Or we could just shove the plug up Wilkes' butt and see what happens." Ashton said. "I say we just shove the plug up his butt."

"On the bed, Wilkes," Rivers said, smiling. Rob Wilkes knew well the position Rivers expected him to assume and he assumed it without further instruction. He knew stalling was something newbies did -- out of embarrassment or fear. Wilkes was neither embarrassed nor fearful. He was resentful and in a hurry. He wanted this over with. Rivers, in this instance, accommodated him by getting down to the business of plugging Wilkes ass. He presented the narrowed tip of the plug to Wilkes' anus and immediately began pushing. Wilkes knew enough to push back, relaxing his asshole to let the plug pass more easily up through his restricted anus and into his rectum. He loudly sucked air in through his teeth as he felt the pain of his anus being stretched wide to accomdate the widest portion of the plug. Rivers stopped pushing at this point to have the pain last a little longer. Wilkes' eyes were shut tightly as though he were closing out the pain as well as the light of the room.

"Don't want to make any noise, huh?" Rivers asked as he twisted the plug a little. Wilkes cried out, but softly.

"Awwllll."

"Trying to impress your roomie or me Wilkes," Rivers said. He shoved the plug home in a single push.

Wilkes felt his asshole close down around the narrow neck and the base of the plug drawn up tightly against the area surrounding his anus. The body of the plug filled his rectim causing him toi feel the need to _s_h_i_t_. He ignored this feeling and now mentally prepared for the switch which he saw Rivers pick up off the desk. Rivers couldn't resist playing with the plug a little before he began the switching proper. He pressed the based hard up against Wilkes' butt and even twisted it back and forth slightly.

"Nice tight fit," Rivers said. "Like it was made for ya, Wilkes." Kenny watched with fascination and, yes, a sense of admiration for what Wilkes must be feeling.

"How many?" Ashton said to Rivers.

"Up to Wilkes," Rivers answered. "Do you want ten medium ones or six hard ones, Wilkes? Your choice." Wilkes knew the difference.

"Ten medium, Gurad Rivers." Less than a second later, Rivers landed the first switch on Wilkes butt. To Kenny it looked like a hard one but he was as yet inexperienced with the switch, especially looking-on while another got it. There followed two more switches in rapid succession. Unlike the paddle the pain of the switch is immediate and pause between blows for the pain to register is not necessary.

"Oh _s_h_i_t_, _s_h_i_t_, _s_h_i_t_," Wilkes said, but not loudly. Rivers paused a few seconds to study Wilkes' face then two more. Wilkes said nothing but threw his head back.

"Bet your asshole is really squeezin' that plug ain't it Wilkes," Rivers said as he tapped the protruding base of the plug. He reached forward with his free hand and rubbed Wilkes' anus where it clamped down tight on the neck of the plug. Then three evenly spaced switches, two across his middle butt the last down low. Wilkes lowered his head and yelled. His cry was muffled by the mattress. Rivers gave him no time to recover before the next, another one down low, almost on his legs.

"Surprise, Wilkes," Rivers said. "Only nine. A present for you. Especially since one of those a few back was harder than a medium. I just got carried away watchin' you squirm, I guess." Rivers put the switch on the desk.

"Okay, Wilkes," Rivers said holding the base of the plug. "Give it to me." Kenny watched as Wilkes took a deep breath and pushed hard. The plug slowly emerged from his rectum, through his anus and then almost squirted into Rivers' waiting hands. Wiles loudly exhaled. Rivers quickly stripped the rubber off the plug and tossed it on the floor. Wilkes remaining in his position, his balls, the red marks from the switch his butt and his anus in full view.

Ashton quickly put the _d_i_l_d_o_ in the bag along with the box of latex examining gloves and the tube of lubricant. Rivers went to the room's wash basin and quickly washed and dried his hands. Ashton picked up the plastic bag and clipboard, Rivers the switch and paddle. They both walked to the door which was standing partially open. Kenny remained staring at his roommate's behind, legs and the soles of his feet.

"You can get up now, Wilkes," Ashton said as he and Rivers took one last look and turned to leave the room.


More stories byJason A. Andresen