Glengreave College Ch. 05

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John invites Susan to assist in the humiliation of a boy.
2.5k words
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Part 5 of the 5 part series

Updated 02/16/2025
Created 02/15/2025
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Chapter 5

In the 1960s, before widespread use of the new contraceptive pill, Glengreave College was keen to avoid any pregnancies on campus. Accordingly, male and female students were educated separately and kept apart as much as possible. Dormitories in particular were strictly out of bounds for members of the opposite sex.

Having come from mainly rural Scottish communities, most students were inexperienced in sexual matters but that didn't reduce their hormones and desire to gain experience. Meanwhile, although the college did not officially approve of same-sex relationships, the staff turned a blind eye to any boy-boy or girl-girl relationships as this reduced the risk of students sneaking into dormitories of the opposite sex.

Even John and Susan had had little contact with the opposite sex in their time at Glengreave. Now, as Senior Student Representatives in their fifth and final year at the college, they had been given permission to meet to discuss the new arrangements whereby they were administering caning and so had access to each other's private quarters.

The previous events, discussing their past sexual histories and their first term of carrying out canings, had all taken place on one wintery afternoon toward the end of the term. When they got together again at the beginning of the spring term, they were both excited at the prospect of what they could do together now, with their new playmates.

They agreed loosely that, if John had someone for caning who he thought Susan might be interested in, he would invite her to be present. She had expressed her desire to cane some naked boys. Similarly, if Susan had anyone interesting to be caned or was going to be seeing Carla, Samantha or Goldilocks again she would invite John to her room.

John was the first one to make an invitation, and Susan joined him in his rooms late one afternoon. John explained that, unusually, he had two boys coming to see him to receive the cane at the same time and they were due shortly. The situation appeared to be that a second-year boy and a first-year boy had been caught having sex together in the changing rooms. Both boys were due to receive six strokes of the cane. However, John explained that he had made enquiries, and the situation was more complicated. The second-year boy was quite a bully. He often ridiculed and taunted smaller younger lads, especially those who were known to have any homosexual tendencies. Sometimes he got his henchmen to restrain a boy while he pulled down his trousers and wanked him off. On this occasion it was clear that the young boy in question had not consented to sex although he'd appeared to be enjoying it when the staff member had found them. It seemed that the older boy's friends had held the first-year bent over a desk, and stripped off his trousers, and then applauded and egged the second-year on, watching as he fucked the arse of the younger boy. The older boy, however, told everybody that he wasn't a homosexual he just did it to show them it was wrong.

John had already decided that he was going to let the younger boy off and give all 12 strokes to the bully. And instead of clearing a space in the middle of the room, he placed a heavy wooden table there and prepared some rope.

The two boys duly arrived and looked surprised to see Susan in the room. John explained that she was simply there to observe. Both John and Susan were holding canes in their hands and were now proficient at exuding menace and authority.

The older boy, Gavin, was John's height with dark hair but didn't appear to be particularly strong. The younger boy, Simon, was shorter and slim and it was easy to see why a bully would pick on him.

To continue the pretence that both boys would be caned, John ordered them both to undress. They each looked shyly at Susan as they did so, keeping their backs to her. Susan sat quietly on a chair in the corner.

"To adopt the correct position for caning, you need to bend over this table," said John with authority. "In order to ensure that you don't become agitated whilst receiving the cane, it's necessary to ropes to your wrists and ankles," said John. As Gavin had never received the cane before it wasn't difficult to deceive him.

Gavin lent across the table and John tied his ankles to the bottom legs of the table and his wrists pulled tightly across the top. Gavin was now stretched naked across the table, unable to move. His penis dangled limply from his groin, below the top of the table, a detail which wasn't unnoticed by Susan.

She had been waiting for a chance to watch naked boys being caned. She was always turned on when caning girls with their knickers pulled down and naked boys was even more exciting.

It was at this point that John explained what was going to happen. "I've made some enquiries and it's quite clear that Simon here is completely innocent. In view of this, Simon you will not receive the cane and your 6 strokes will be passed to your aggressor. Gavin, you are to receive all 12 strokes."

Gavin immediately protested and tried to escape the ropes, finding that he was unable to move. To stop him shouting, John took Gavin's own underpants and pushed them into his mouth.

Now the scene was set, Susan stood up. She was eager to watch this bully receiving his punishment. John had previously told Susan that some boys when receiving the cane became sexually aroused. It was unclear whether this was due to blood flow to the area, adrenalin or other reasons. Susan was excited that this might occur here. She was also keen to find out how honest Gavin was when protesting to all his friends that he was not a homosexual.

Susan stood beside Simon and they both watched as John delivered the first stroke. It hit hard on his pale bare buttocks and Gavin screamed into his gag. John paused for some time, allowing the anticipation of pain to grow before delivering the second stroke even more forcefully. Gavin screamed again. How often it is the case that the bully is the least brave. Susan was biting her lip and breathing heavily as she watched. She was also quite excited that young Simon standing beside her was also naked and she put her arm around his bare shoulders.

After the third stroke, John walked around him and asked him if he intended to continue being a bully in future? He couldn't talk through his gag but shook his head to confirm that he would not. But Susan had her eyes fixed on Gavin's cock which had started to swell after the first couple of strikes and was now fully extended. Susan had a strong impression that, far from his protestations, Gavin had been excited to be caned, to be humiliated and naked in front of them all. When he turned his head and saw both Susan and Simon staring at his hard cock, it appeared to spring up even harder.

John continued taking his time to deliver three more strokes and with each stroke Susan watched his hard cock sway from side to side. John paused to walk around ensuring the maximum humiliation before continuing. For the final six strokes he invited Susan to take over and she was more than willing. While not having quite the strength of John, she was highly experienced and with Gavin's backside already being raw and bleeding, the strokes she administered were no less painful.

Susan was feeling very turned on, it was her first experience of caning a boy and it was exhilarating. She watched closely as, every time he flinched with a stroke of the cane, his penis swung from side to side. Before proceeding with the final three strikes, she approached him.

"So you like being a bully do you?" Unable to speak he shook his head. "But it looks like you enjoy receiving pain as well as administering it," she said as she took his hard cock in her fingers and started wanking it slowly.

Gavin's eyes opened widely, confused as to what was going on. One minute she was inflicting horrific pain and now she was wanking his cock. Then she pulled his foreskin down as hard as she could until it almost hurt, watching him wince. Her pussy was throbbing as she held his hard cock and she kept the pressure for several seconds as he moaned into his gag. She felt it throb and guessed that if she continued the pressure much longer he was going to ejaculate.

Then Susan returned to her spot beside him and snarled, "I've got no time for bullies." And with that she inflicted the final three blows as hard as she could, watching gleefully as his hard cock swung from side to side.

The 12 strokes had been administered, but her sense of justice craved something more to happen. She sensed also that John was quite turned on having delivered the blows.

Susan decided to explore whether there were further options. "I'm not sure the punishment is sufficient" she said. "I wonder if there is a more poetic justice we can apply, and maybe find out whether he really is a homosexual?"

"What did you have in mind?" Asked John although he had a good idea what she intended.

"I think Simon has a right to get his own back," said Susan "here and now while he's tied up and cannot refuse."

Sensing what she implied, Gavin tried to remonstrate. Although his words could not be heard clearly, his cries of "no, no, no" were unmistakable.

"Yes, yes, yes," said John," and if you tell anyone we will let the housemaster know about all your bullying and persecution of first-years."

Susan turned to Simon who had been watching the entire episode in silence and a degree of fear. "Don't worry," said Susan, "nothing is going to happen to you that you don't want to happen. Tell me, would you like to do to him what he was doing to you?"

Simon stood and thought for a while before responding, "actually yes, I would it would serve him right. But at the moment I'm not sure I'm equipped?" He said indicating his flaccid member.

"Let me see if I can help you with that," said Susan, gladly reaching down one of her slender hands to stroke his penis. She always enjoyed the challenge of awakening a penis from its sleep and with her gentle and expert touch she soon had his cock growing until it was fully engorged and hard in her palm. For Such a small boy she was impressed with its size and was very tempted to continue wanking it till he came. But she knew that was not the plan.

"Now, he's at your mercy, do your worst," she said.

Gaining courage, Simon approached Gavin's backside. He paused a moment looking at John and Susan for encouragement. They nodded. He pressed the tip of his cock against Gavin's arsehole. At the same time Susan nodded to John to indicate that he could also get involved and increase the humiliation. John stood beside Gavin and put his hand around his cock. "Let's see how someone who's not a homosexual enjoys a male wank and an arse fuck."

Gavin was shouting into his underpants stuffed in his mouth, but he couldn't be heard. Simon pressed the tip of his cock into Gavin's arsehole as Gavin continued to protest. Simon slowly pushed his cock deeply inside and started to fuck him. And then amazingly, Gavin's shouts changed to moans. He started moving his hips in rhythm, as much as he was able with the confines of the ropes. Simon was enjoying having the power for a change and continued pushing his cock deep inside, fucking him hard. John meanwhile was wanking Gavin's cock. Gavin was breathing heavily now. Simon was thrusting his cock like a piston as the bully remained tied up and unable to move. Susan was also getting very turned on watching and positioned herself behind Simon so she could lift her skirt and masturbate herself as she watched.

It wasn't long before Simon ejaculated in his arse. John continued to wank the bully as fast as he could and moments later he came all over the carpet.

Simon withdrew and John showed him where the bathroom was should he wish to clean himself. Meanwhile, he untied Gavin and removed the gag. Gavin looked crestfallen as he got dressed. "Please don't tell anyone what happened," he asked pitifully. John assured him that he would not, as long as he ceased his bullying behaviour. But if he heard of one more incident of abuse, he would tell everyone that Gavin had cum while being fucked up the arse and wanked by another boy. He'd also let all the authorities know about his bullying behaviour, and that would almost certainly result in his parents finding out and him being expelled from the college. Gavin left with his head held low.

Simon returned from the bathroom, clean but still naked. Susan looked him up and down and realised she was still horny. "Tell me Simon, do you only enjoy boys or do you like girls as well?"

"Well in theory I like girls," said Simon, "but I've never had the opportunity to find out."

Susan smiled at John. Then turning to Simon she started to remove her clothing, slowly and seductively, "I think it's about time you found out."

It was John's turn to sit on the chair and watch, realising this was something special for Simon and Susan. He watched as she stripped herself naked in front of the young boy. John could tell she was enjoying the boy's attention, his eyes wide as he looked at her beautiful and athletic naked body. He watched as Susan moved up to Simon and kissed him, her hands stroking the back of his head, his shoulders, his naked back and then his backside. He watched as she took his cock in her hand and expertly stroked it up and down making it hard again. John knew from experience how excited she would be, to be holding a young virile and virgin cock between her fingers. He watched as she lay down on the sofa and encouraged Simon on top of her. By the time she had taken his cock in her hands and directed it into the tip of her crack, John had his own cock out of his trousers and in his hands.

John wanked as he watched this young boy losing his virginity to his beautiful blonde friend. He watched as Simon came inside her and moments later when Susan orgasmed, John came too.

Needless to say, later after Simon had left as well, John and Susan retired to the bedroom and discussed the events of the afternoon and spent the evening making love to each other.

[Note from author: Please leave comments if you enjoy the story. More Chapters will follow soon.]

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FlashingJackFlashingJack13 days agoAuthor

Next chapter is almost complete. John gets introduced to Goldilocks.

Mike7845Mike784516 days ago

Please keep the story going

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