Scotlands Alcatraz

Chapter 4. Teacher punished

"Come in Rosalind." Nervously she entered the headmaster's office. "Sit down please. You have of course guessed why I sent for you." Rosalind nodded yes. "Would you like to tell me your version of the events that led up to this morning's fiasco? And then perhaps make recommendations as to how you might prevent it happening again."

"I wasn't prepared for that girl's outburst. I didn't expect it. I was nervous. This is my first job in this sort of situation and I thought they would all be cowed down by it all. They weren't. I don't think they are now, even after the thrashing you gave Jan."

"Where was your tawse Ros?"

"In the drawer. Hidden. I didn't want to intimidate them."

"So they intimidated you instead?"

"Yes, I suppose so," Rosalind meekly replied. "What are you going to do about it? Sack me? Or?"

"Or what Ros?"

"Cane me," Ros replied quietly.

"Ros, Do you think you are cut out for this job? If you don't think you can handle this lot, then no amount of caning will help. It's not like it was with Jan. You might just as well leave and go to a normal school."

"I don't want to leave Derek. I came here because I thought I could do a good job but it may take me a week or two to get into the way of things. You and the others have taught in prison schools or been warders before so you had some idea of what to expect. I came straight from college. If it takes a tawsing or a even caning to keep this job for a few weeks to prove I can do it, then so be it."

"Ros, you saw what Jan was like after her caning. In view of the gravity of the situation and the fact that you were the root cause of the kerfuffle, you ought to have at least the same as she did." Rosalind gasped at the thought but Derek went on, "However, you might find it even more difficult to teach for the next few days therefore, if you decide to go that route, I propose to only give you six with the cane provided that you allow me to comfort you in my room afterwards."

"You mean you would want to…?"

"To put it bluntly, I would want you to strip naked, lie over my desk and be fastened down like Jan and receive six strokes of the No. 2 cane, same as she had. I don't intend to pull the strokes so you will have to take the full force of them again the same as Jan. For propriety, you can opt to be gagged so as not to let the whole prison know. With Jan I wanted her screams to be heard far and wide. Afterwards I will take you through those doors into my personal rooms and do what I can to alleviate the pain but, yes, I do intend to fuck you at my leisure. It will all be considered part of your punishment package. So the choice is yours. Either hand in your resignation, or if you refuse to do that, I will sack you. The alternative is the cane and my cock and my bed. Which is it to be?"

"I guess I don't have a choice at all if I want to stay," Ros remarked tearfully, "This job pays well, I have my own accommodation and I think I can get to like what I do once I learn how to deal with these 'students'. Shall we just get it over with?"

"Not now we'll wait till later tonight. Say ten o'clock when it's quieter and then I think we can get a little more pleasure out of it than a quick caning and a fuck, Ros. We'll start by undressing each other. When we're both starkers, I'll do the painful bit and afterwards back to pleasure again."

I don't think there will be much pleasure in it for me after you've thrashed me, but okay, I guess I'll have to go along with it."

"See you at dinner." Derek knew she wouldn't get that much pleasure from what he intended to do, but he certainly would! He hadn't told her all he planned to do.

Because there were as yet only a few students in the prison, students and staff who were not on duty ate in the same dining room. Derek had also decided on a family service system. Tables were laid for eight people, staff and students mixed. One from each table went to the hatch to collect the food tray for the whole table and served it. Jan and Denny caused some amusement as they hadn't yet learned to move in time with each other. Apart from being tied, they seemed an odd couple. Jan's large form was a complete contrast to Denny's four foot eleven frail frame. Still he seemed to be considerate to her and she allowed him to apply the salve the nurse supplied. In turn, Jan mothered the boy as though he were her baby boy.

Derek saved a place for Rosalind but with students Quack, Sally, Maureen and Pete on their table as well as two of the security staff, the talk was on more mundane things, like their interests and girlfriends at home. Derek hoped to use these sessions to build up a picture of his students. Rosalind tried to hide her nervousness at what she knew would happen later, behind giggling and false laughter. As they left the table, Derek whispered, "I suggest you spend the evening preparing tomorrow's lesson and working out how you are going to deal with your class. I shall keep an eye on you but won't interfere unless it is absolutely necessary."

At ten precisely Rosalind walked to the head's office wearing only her gown. In this place she knew her tryst would be monitored by the security staff so there was little point in trying not to be noticed but she hoped Derek could turn off the cameras in his office.

"She's going into his office Pete," Patti said to her on-duty colleague, "I reckon she's going to get screwed."

"More likely she'll get her bum warmed after this morning's incident. That I must watch. She's a nice looking young thing. Not too much in the tit department though." Pete chuckled to himself.

"You just watch your screens otherwise we'll have our arses more than warmed if something happens and we don't spot it. Those new students could well start to get frisky or start fighting."

"Not much happening here. The twins are in bed together but the covers aren't moving much. Let me know when something interesting happens."

"Yeah okay Pete, just as long as you don't get too horny yourself and want to screw before the shift is over. I don't want to lose this cushy job."

"Come in Ros," Derek answered her knock, "You look lovely in that thin gown. Like an eastern princess."

"I doubt I will look as nice when you've finished with me." Rosalind gave nervous laugh. She was very apprehensive about the whole thing. She'd admired Derek's looks at the interview in Birmingham last month and again at the staff meeting two days ago and a more personal interview afterwards but at these Derek had been fully dressed and his manner correct. Today she'd seen how cruel he could be and it was even whispered that he had shagged one of the guards while the girl had to watch. She trembled when Derek opened her robe and slid it off.

"Take mine off now Ros and then we can examine each other properly."

"I think I would just like to get the caning over with if you don't mind Derek." Ros slid Derek's robe to the floor and was immediately captivated by his already erect cock. "Perhaps you could just punish me with this?" she suggested taking hold of it.

"Oh, I will Ros, I surely will, but only after I have warmed your bottom a little." His cupped her breasts, squeezed them and finally pinched her nipples enough to make her cry out. "Hmmm I shall enjoy taking this little bitch afterwards," he told himself, "I don't think she's experienced too many men before and certainly not had a thrashing like she is going to get now." They fondled each other for a few minutes until Derek quietly led her to his desk and fastened her wrists and ankles "I shall certainly enjoy thrashing this tight arse. I'll make her squeal with the cane and then with my cock," Derek said to himself.

"Don't be too hard on me Derek please. I've got to teach tomorrow."

"I know but a punishment is a punishment. Jan had to go back to her lessons afterwards. To be effective this has to be a proper caning and you are only getting half her amount because you are submitting to punishment by my cock afterwards for a couple of hours or so."

"He's got her tied and spread over the desk now Pete and he's getting the cane from the cupboard." Patti informed her fellow guard. "I wonder if she'll get the same as that girl?"

Pete pushed his office chair so it sped across the floor and he could take a look at her screen for a few moments. "Nice," he commented, "Wouldn't mind getting a piece of that cunt myself especially after the boss has tenderised her a bit. Everything's quiet on my screens. Sarah went into Josh's room and hasn't come out."

"So I can take you to my room after the shift, if she's not there," Patti laughed, "Now get back to your screens. I'll let you know when the action takes place. You can replay it anyway later." Before Pete sent his wheeled chair zooming back to his section of the monitor room, he'd watched as the first stroke landed on Rosalind's arse. He saw it lift and writhe under the impact. "Looks like he's not going to be easy on her, Patti. That was no light tickle." A movement in the boy's dorm caught his eye but it was only Quack getting up and walking to the loo. He had an erection. Pete followed the lad's progress and rightly guessed the boy needed to wank himself. He passed the information to Patti but she was glued to the screen showing the boss and the teacher.

"Oh my God!" screamed Rosalind as the first stroke bit deeply into her bum flesh. Pain seared its way into her brain. Fire coursed through her arse. "Not so hard Derek, please. I can't take six like that." She continued to plead until Derek silenced her with a gag. It was small but effective and kept her from waking others while he waited for her to settle down again.

"That was no harder than I gave Jan, and yes you can and will take the full six." With some satisfaction he surveyed the deep red welt that now ran across her derriere just above the crease to her thighs. Her muscles twitched in agony and her arsehole and cunt, completely on display by her widely spaced and tied legs, seemed to move in inviting circles. "I think I will take her like this when she's had her full dose," he told himself. "I don't think I can wait until I get her into my room." He lashed another terrible stroke across her arse, just above the previous one. The writhing and gyrations that followed her first stroke were repeated but her screaming was reduced to muffled moans. Derek grinned sadistically as he watched he writhe in agony.

Thoughts ran wildly through Rosalind's mind. "I really can't take six like this and have sex with him afterwards and teach in the morning. And Jan took twelve like this? Can't believe he is not hitting me harder than he did her. It feels like it. The bastard. Perhaps he will take pity on me. Or just get so horny he has to fuck…" He thoughts were interrupted by the third stroke.

"Halfway now Ros." Derek placed a hand on her bum. "Warming up nicely now. Hope your cunt is warming up nicely too."

"Bastard, bastard, bastard! Warming up! My bum would fry an egg. He thinks this is foreplay? No, this is just hell. Why, why, why, did I agree to it? Why did I apply for the job in the first place? Why did that bitch Jan try and defy me this morning?" Ros' thoughts went crazily through her brain.

"Crack!!!" "Four." Once more the wait.

"It's not fair. It's inhuman, just like Denny said. He's just a sadist. He likes to hurt women. Perhaps he likes boys too."

"Crack!!!" The wait wasn't as long this time. Derek was becoming impatient. "Only one more to go so I'll make this a good one," Derek told the sobbing woman.

"Bastard! The others were plenty good enough for me. I shan't walk for a week. What's the sod waiting for? Get it over with. Let me go back to my room. You can forget about fucking me." All Derek heard was muffled groans from behind the gag.

"Crack!!!" the last one crashed down on her already tormented backside. For a few moments she thought she would pass out but there was not even that relief from her pain. She felt Derek's hands gently massaging her arse. "Release me," she tried to tell him, "Let me up and let me go. I want out of here." The hands left her arse and Derek moved away and when he returned she caught a glimpse of his rock hard prick. Her view of it somewhat obscured by watery eyes. Again the hands were on her arse but this time a finger coated with Vaseline was prying around her arsehole. Horrified, Rosalind tried to convey to him her objections. "No, no, no! I hurt badly enough without that. I've never done it that way and don't want to. Leave me alone you pervert!"

Although he couldn't hear her words, Derek knew she was objecting strongly. It pleased him. He liked a bit of arse now and again. Boy or girl, it didn't matter and if they were helpless to avoid it, so much the better. This woman would learn what life in this prison, this Alcatraz, was all about. "Ready for your first fuck of the evening dear?" he enquired knowing she couldn't reply and knowing she had no choice.

"He really laid it on her Pete," Patti told him, "And now it looks as if he is going to fuck her arse while she is helpless. Looks like rape to me. He's forcing it in now. Good job he is a normal size. He's right in," Patti excitedly continued her commentary.

"He fucked you yet Patti?" Pete asked.

"Not yet. You saw how Sarah had it this morning so I guess other females have too. No doubt he'll get round to me before too long. Just as long as it is not after a thrashing I shan't mind too much. He's fucking her hard now. Poor bitch. Bet that is really hurting."

"You ever had it in the arse?"

"Yep. One of my boyfriends had a small cock so it wasn't painful. I bet she'd be screaming if she weren't gagged. His balls are thumping her welts."

Indeed that was the case. To Ros, the feel of his prick inside her hole was not now unpleasant but when his balls thumped against the sensitive stripes, she nearly hit the roof. Derek tried to hold his seed back as long as he could to keep the enjoyable sensation going but all too soon for him, he shot his load into her bowels and collapsed on top of her. There he remained for several minutes until his cock went soft. He stood up and spoke to Rosalind. "I really enjoyed that Ros but I guess you didn't too much. No matter it was supposed to be a punishment session. You have one more thing to do before I release you and take you to my bed for the final hour or so of our time together. When I remove your gag, you will suck my cock clean. Only then will I release you from the desk and do what I can to reduce the pain. Afterwards I will fuck your cunt and then you can either stay in my bed or go. Your punishment will be over; your slate wiped clean."

Despite her repulsion at what she was being forced to do, Rosalind did take the soft cock in her mouth and sucked until she felt it begin to stiffen. Derek kept his word and gently helped her into his own room. He sprayed her welts and gave her painkillers but his estimate of an hour before she was ready to fuck, was a long way out. Three hours later, he was able to get hard enough and she was calm enough for him to fuck her. Even so, she had to lie across the bed with her arse overhanging the side so no weight went on it. It was 2 a.m. when Patti and Pete saw her reappear on their screens and make her painful way to her own room.