Pain & Pleasure III

by FW <sapper888@yahoo.com>

( TO GET THE FLOW OF THIS TALE PARTS I & II SHOULD BE READ FIRST. THEY CAN BE FOUND ON MMSA Stories'S PAGE UNDER THE AUTHOR FW.)

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Josh Wilson and Eliot Seetin sat on Rick Morley's bed, they glanced at each other then Eliot Seetin spoke.

"Last night we were breaking bounds by being out of our dorm, and taking part in a dare game. Our dare was to bring back an item from the senior housing area. As we were passing your window we saw a caning being given to someone. Being curious we crept up to your window to see who was getting a thrashing so late at night.

What we saw was you two enjoying yourselves, we stayed till you finished then returned to our dorm forgetting the dare. We each got one whack of the slipper from the others in our dorm for being chicken and not binging back a trophy."

Josh Wilson continued.

"We have the same feelings after being caned, but due to the lack of privacy of the Junior dorm we cannot continue as you do. So what we were wondering is can we join you in one of your sessions?"

Rick broke the silence

"Do you know why I was caned?"

"No" both juniors replied. Morley was concerned that the full story might have been leaked to the School and that would have been a disaster for his remaining time at the school. Satisfied that the two did not know the complete story he turned to Dutton.

"I think these two have a tremendous nerve coming here and confessing that they have invaded our privacy, under the guise that they would like to join us in our hobby."

Roy Dutton nodded agreement. He moved to the window and firmly closed the drape checking to see that no parts of the window were uncovered.

"We cannot allow a confession of breaking bounds to go unpunished, and I agree with you that they have indeed placed ourselves in a rather delicate position. It is best that they are put to a test."

Looking directly at the two juniors, Dutton put on his Head Boy stance and voice.

"Very well you two, Blazers off, shoes as well, then your trousers. You are each going to get a caning that you will not soon forget. Then we shall see if you want to continue with other pleasures."

Josh and Eliot looked at each other, the same thought passed through each mind, maybe we made a mistake.

"Move." Dutton commanded. Both boys now quickly divested themselves of their clothing as ordered. They now stood only in socks, shirt, and their white briefs. Dutton had gone to the closet and taken out a cane, medium weight, long, it would deliver a scorching sting, a welt that would be the pride of any dorm in the school, but no long time bruising.

"Six apiece, the best I can deliver, then we'll see about the rest." Dutton pointed to Josh.

"Over here." Josh walked over to Dutton who was standing by the table, laying the cane on the table he reached over and slid the boys briefs down to his ankles. The boy's penis was exposed, begining to swell while nestled in a dark tuft of pubic hair.

"Over the table, grip the far side, tightly, now your legs wide apart, come on wider."

Josh was now bent over the table the effect of his wide spread legs was to raise his heels well off the floor, and push his upper body down on the table forcing his head to turn sideways. Dutton took the boys shirt and pushed it up his body. The next move was to order Seetin to stand at the end of the table, and place his hands on his head. This had the effect of raising his shirt and expose the bulge in his briefs. It was moving in an upward direction as he stared down at his friend spead acoss the table. From his position he would be able to see everey stroke as it lashed his friends buttocks. Rick Morley stood directly behind Seetin. The view over the shoulder of the smaller boy was also unobstructed. His eyes were fastened on the firm white globes of Josh's buttocks, and his erection was complete.

Dutton took two steps backward, raised the cane and stepping quickly forward brought it lashing down across the firm white flesh.

From his position on the table Josh was looking directly at the crotch of his friend, and he could see that Eliot was already enjoying an erection, and it was starting to affect him likewise. Then he heard two quick steps, a swoosh of moving air. A heartbeat later he felt the pressure of the cane as it creased his exposed buttocks, in that same heartbeat his bottom seemed to explode into a ball of fire. He jerked forward grinding his erection into the edge of the table causing it to harden even further. He screwed his eyes closed as the vicious sting coursed through his nerve ends.

Eliot and Rick from their vantage point at the end of the table had watched as Dutton brought the cane lashing down onto the buttocks of the other. They watched as the instrument creased the flesh then as it rebounded the fierce red of the welt was exposed. It appeared to be a line of fire across the white buttocks. Josh jerked forward screwing his eyes in pain. The erections of the two watchers strained at their respective clothing.

The second stroke seemed even more powerful as it had the same marking effect on Josh's bottom. The third was lower and landed where the tender flesh formed the crease between leg, and buttock. Josh let out a yelp, and started to raise up.

"Down, and be quiet" Dutton growled then delivered the scorching fourth stroke to the youth bent over the table, Roy Dutton was also sporting an erection of immense proportion. The penultimate stroke caused the penis of the boy being caned to again grind against the table, and try as he might he could not stop the begining of an orgasm, the sting of the final stroke was not the reason that Josh pulled himself against the table sending a stream of his sperm splashing onto the floor beneth the table. This was not unoticed by the other three in the room. Jopsh pulled himself twice more against the table before relaxing with a groan against the table top.

"Get up you are finished for now" Dutton spoke.

Josh stood and the action of his moving the spread legs, and contracting the muscles of his bottom brought a sharp intake of breath to his body. His buttocks were crossed by six very plain bright red stripes.

"Change places"

The scene was repeated as Dutton lowered the briefs of Eliot, this time he had to pull them outward to allow the engorged penis of the boy to free itself from the cloth. He bent him over the table and went through the ritual of spreading the boys legs wide apart. Again the shirt was pushed up to completely expose buttocks soon to be lashed. The caning began as before, this time Josh and Rick watched the stripes explode into view on Eliot's bottom. The third stroke had just burst into view on the white buttocks when . . .

A series of sharp knocks on the study door, as Rick reached for the door, it opened and a head poked into the room. It was Eliots older brother Sam, a senior and Prefect in charge of the dorm the two juniors lived in.

"Oh excuse me, I was just on the way to the shower, got any shampoo? I did not know you two worked on Saturdays" he joked at the two seniors. Looking at the boy on the table he shook his head.

"My baby brother . . . now what have you done?"

"Breaking bounds" Dutton spoke directly to Sam.

Looking at the the table again he said to his brother, " Will you never learn?, you and your constant partner in crime Mr. Wilson. Well this time I will make you both very sore. I have errands to run, I expect you both in my study right after supper."

Taking the offered shampoo he turned to the door, stopping a moment he looked back.

"Be sure to wear something that will slip off your bottoms easily, don't be late" then to Dutton, "Lay it on well Roy he needs it." Then he left the room closing the door behind him. This time Rick locked it, further interuptions could be awkward.

Dutton returned to the matter in hand, and continued the caning with renewed vigour after the short breather.

On the table Eliot had heard the exchange with his brother, and initially was dismayed to be told that further punishment was to be given to Josh and himself, but then it would be several hours, and youth has a way of renewing its hurts in a very short time. He had seen that Josh's position on the table had caused his friend to be rubbed against the table and consequently erupt. As he bent over the table, he made sure that he was far enough away to avoid any contact with the table and his penis. This resulted in his bottom being pushed up and out, making Dutton's task easier as he flogged the supine youth.

The last three strokes of Eliots punishment were indeed scorchers and tears streamed down from his eyes, and sobs were evident.

"Get up" Eliot stood slowly his erection was pulsing, the head of his penis shone in its hardness, he moved his arms as if to touch his throbbing part.

"Hands on your head now" Morley ordered. Eliot obeyed.

Now both boys stood their bottoms red and welt covered, hands on head. Josh was showing the beginning of another erection, he was not very happy about the interruption of Eliot's brother and the resulting promise of further painful caning.

Rick had placed a jar of cream on the table, and motioning Josh to bend over the table again took some cream on the hot welts of the boys bottom, a liberal amount was applied to the tight sphincter as his finger entered Josh. The boy moved backward at the feel of the entry to his bottom. Taking Eliot by the arm Dutton placed him behind his friend, putting his fingers into the jar of cream he put cooling covering on the still throbbing penis of Eliot. No further prompting was necessary, Eliot guided himself to enter the waiting relaxed anus of Josh.

Gripping his friend by the shoulders he began to thrust right up to the still hot buttocks then withdraw to the tender head of his manhood before thrusting forward again. It was more than he could stand and he had to release his juices into the warm tightness of Josh's body the final thrusting brough gasps from the lips of both boys as Josh was now in a state of arousal again.

Rick Morley and Roy Dutton watched as Eliot spent himself. Then as if on a silent command they both quickly undressed. Rick took Eliot and bending him the end of his bed slapped the junior across his red bottom with one hand as he used the other to lubricate himself before thrusting into the body of Eliot.

At the other end of the table Roy Dutton was bent in front of Josh, and was guiding the now red hardness of the boys penis to his own waiting sphincter.

Later as all were relaxed and dressed again, Dutton admonished the two Juniors.

"Let that be a lesson to you both, you cannot just violate the rules as you wish, now off with you and don't forget your appointment with Mr. Seetin. When he is through with you both you had better report here again, and Rick and I can perhaps soothe what I am sure will be some sore buttocks."

[comments welcome]


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