Trainingware Pt. 06

After a pause, Judy added, "In fact, I want you to be as nice as you can to Gwynn from now on, but only as a friendly older brother. If she tries to flirt, just tell her that you wouldn't feel right, and it wouldn't be a good idea anyway. But be encouraging and let her know you think she's cute. Tell her you're sure there are boys in her class who want to ask her out, but are just too shy. I think I know a boy her age who'd be suitable, and I'm sure he'd be interested if he thought Gwynn liked him. Can you remember all this and do it right?"

I answered that I would, and Judy said, "That's an assignment I'm giving you, David, and I want you to make progress on it when you have a chance to talk to Gwynn, or I'll punish you for that!"

I cringed away slightly, and then I felt my punishment shorts slipping off as Judy told me not to move. My erection had been at a sixty degree angle making a tent in my shorts ever since Judy arrived, and now that I was naked it was my most prominent feature. I felt an unbelievable wave of shame to appear in front of Judy this way, so exposed, as bad as I'd felt when she made me stand like this yesterday. I couldn't understand why I wasn't getting more used to it! It wasn't supposed to be just as embarrassing the second time, was it?

Suddenly, Judy's voice was less serious, "Is that something Hubba is doing, David, or are you just glad to see me?" She was playful all of a sudden, looking at my erection and reaching out to touch it lightly. I jumped when I felt contact and my face flushed as hot as I thought it ever got.

"Now walk into the punishment room," Judy said, picking up the punishment wand from the table. "And get onto the positioner."

I felt frightened enough to start crying quietly when Judy picked up the wand, and I was trembling by the time I stepped on the stirrups of the positioner and laid forward. The restraints snapped around me again and the positioner lifted me up and rotated me to whipping position.

Judy came up behind me, and started using the wand on my behind in the warm- up. At the end, there was a pause, and I started full-throated crying because I knew what was coming. When the whipping started, I was shrieking with every slap again, and bawling like a baby before very long. When the slaps finally stopped, Judy told me that I'd just had thirty slaps and there'd be another thirty coming after my rest. Then she walked somewhere behind the positioner where I couldn't see her.

I went through the stage of feeling the sting of returning circulation in my behind and the enormously sensitive erection I got from the punishment wand sex-surge. The arousal was worse than ever this time, with Hubba augmenting it. I felt the elongated nipple sliding slowly in and out of my rectum, and the sheath around my cock providing friction with any slight movement I could manage. Only the fact that I couldn't properly rock my hips in the positioner made it possible for me to calm down. After several minutes, I had myself under control enough to look around. The large mirror on the wall in front of me was still showing a view of my face and upper torso on the positioner, but I couldn't see anything behind me so I didn't know if Judy was still in the room. There wasn't much else to look at, and I was trying to concentrate on how to avoid hurting people's feelings when I heard Judy's footsteps coming up behind me again, and all other thoughts fled away as I began pleading with her not to whip me any more.

Judy ignored me, and after my warm-up, when I felt the whipping on my sore behind, I was bawling almost immediately. I continued through slap after slap, too much in pain to plead or even form sensible English sentences. At the end, I went on wailing for a long time. I was still sore from yesterday, of course, and the first round of whipping had made me more sensitive than ever.

Judy raised her voice over my bawling and said she'd be back in a little while to see how good I'd been in other ways. I felt like I needed to pee from fear of more whipping, even though I'd used the bathroom just before I left school. The feeling was really bad for a minute, and maybe a few drops got out, but I figured I'd be sure to get it if I peed on the floor while I was in the positioner, so I finally got myself under control. My main fear was that Judy had seen me humping on my bed last night and this morning, and was going to punish me for that. By the time I managed to calm down from the sensitive erection of my latest whipping round and heard Judy's steps coming back, I was whimpering again.

"I did see you wiggling around on your bed last night, David," Judy said in a cheerful voice, "But I'm not going to whip you for anything like that unless I see you touch your erection with your hand. Anything short of that will just frustrate you, so you're only punishing yourself. You almost put your hand down there this morning, but I was glad to see you caught yourself in time."

That addressed my main worry, but I was still scared because I wasn't out of the positioner yet, and Judy obviously wasn't finished with me.

"What about lying, David?" Judy asked. "Have you told any lies today?"

"No, Ma'am," I answered. "I haven't lied to you! I promise!"

"What about lying to the teacher in Civics class?" Judy asked, and suddenly I felt the awful stinging slaps again, one after another. I think she stopped at four or five, but I was bawling loudly by then and they hurt too much to count. When Judy stopped I tried to control myself again so I could speak.

"You didn't say I couldn't lie to anyone, Ma'am," I said in a shaking voice, still crying. "Just that I couldn't lie to you!"

After a pause, I heard Judy's voice near my ear. "Am I way out of line here, David?"

I stammered that I hadn't meant that, but then felt more slaps that went on for some time, and I was shrieking again.

It took me almost a minute to stop bawling when Judy was done, and then I saw her move to the front of the positioner. She told me to look at her, and as I did I felt a surge of lust, seeing her still in school uniform.

"Now try to understand this, David." She looked very serious. "I'm in charge of your behavior now, and I want you to learn some simple rules. I don't want you to do selfish and egotistical things to gratify yourself: hurt people's feelings, lie to get your way, steal something you think you can use better than the person who owns it, invade someone's privacy, NONE OF THAT!"

Judy leaned forward a little and continued speaking slowly, "I don't want to have to set up lots of little rules. I want you to UNDERSTAND what you're supposed to do! It's simple: I want you to stop doing things you've been told all your life are bad and selfish and arrogant and mean."

Judy looked thoughtful for a moment, then added, "Or if that's too abstract, then think about pleasing ME! Figure out what I want you to do. If you think I wouldn't like it, then don't do it! And you'd better think these things out in advance if you don't want to get whipped every time to learn what I don't want you to do."

Judy paused and smiled slightly, "Think about how to PLEASE me, David! Then I'll let you out of punishment if you make an honest mistake and do something wrong. But I want to be the first person in your life who's ever been real to you, other than yourself and maybe your Dad, so I'm encouraging you here to spend time thinking about my wishes and how you can gratify me."

Then, in a forceful voice, "Do you think you can do all that? Are you motivated enough?"

"Please, yes, Ma'am," I said, as soon as I heard my cue to speak. "I'll do what you want! I'll make it automatic and think about it a lot! I promise!"

"So you don't need any more whipping to drive this idea into your head?" Judy was still smiling slightly, and I thought she was just teasing me now, but I didn't dare take her for granted.

"No, Ma'am! Please! I'll be good!"

Suddenly I felt the positioner moving down and the restraints snapping open, as Judy started walking back to the table behind me. I got up off the positioner, and when I looked in her direction I saw her turn to glance at me. I had a rock-hard erection, and was feeling more embarrassed again. Now that I was off the positioner my nakedness was somehow more blatant, so I asked if I could put my shorts on. Judy said yes, that I was finished with my punishment.

I pulled the shorts on, and then looked at her hesitantly. She seemed receptive, and now that I was off the positioner, there was something I had to ask her, even though I knew it would involve taking off my shorts again.

"Um, Ma'am," I said, and then hesitated. "Uh, could I ask you please to, uh, get me off the way you did yesterday? I'm terribly horny, and this is the only chance I get to ask, so . . ." I trailed off, flushing at having to beg for this, but it was an extremely urgent need at the moment. I was still feeling the sex-surge of the most recent slaps, and I was completely at Judy's mercy if she wanted to tease me by not bringing it up herself.

"I'm not very happy with you right now, David," Judy said, expressionless. "So I think you can wait at least another day."

"Oh, please, Ma'am!" I cried out, shocked. "I can't wait! I won't be able to resist trying to masturbate tonight if I don't get relief from you now."

"I'm not at your beck and call on this, David!" Judy answered, with a snap in her voice. "And of course I'll be keeping a close eye on you tonight. So if you try to masturbate and I catch you at it you'll just get another whipping tomorrow, and then I may be unhappy with you again for trying to masturbate!"

"Please, Ma'am!" I was crying again.

"You're becoming insistent and repetitive, David. You don't want to do that, do you?"

I bit my lip, and then slowly asked, "Can I bring it up again if I say something new at the same time?"

Judy leaned her head to one side and smiled slightly. "Yes, but only if you think I'll like hearing what you have to say. Try to please me, David."

I was pretty sure that what I wanted to suggest would please Judy. "Well, uh, I'd take a whipping over your knee again to get to come . . . like yesterday."

Judy was smiling widely now. "I know you kind of enjoyed that, David. I kept the paddling just at the limit that could sublimate in sexual excitement, so I'm afraid that wouldn't be enough."

Not enough? "Do--Uh --," I was almost afraid to ask, "Do you mean there's something that would be 'enough', so if I agreed to it you'd get me off?"

Judy looked thoughtful, then pointed over at the table.

"If you go bend over the table as you did yesterday, and stand still for thirty-five slaps at full whipping strength, then I'll finish by getting you off over my knee."

I felt a thrill of fear that felt like intense heat all through my body. "I can't, Ma'am," I blurted. "Those slaps hurt too much! I'd never be able to stand still for thirty-five in a row!"

"Well anytime you move I'll just take that one over," Judy answered in a reasonable tone. "I'm sure that if you're sufficiently motivated we'll get through all of them eventually."

I just stood there, feeling miserable, thinking what it would be like trying to stay bent over the table while Judy whipped me, jumping up constantly, probably getting two or three slaps for every one of the thirty-five I'd have coming. And then I tried to imagine how long this would go on while Judy made me take rest breaks so my buttocks would get sensitive again.

"I can't, Ma'am," I said tearfully. Then the urgent need I felt made me add: "But I'd, uh . . .," I had trouble going on, then in a rush, "I'd be willing to get on the positioner while you gave me thirty-five full- strength slaps if you'd let me come at the end." I was ashamed, with my painfully sore behind, to tell Judy what I was willing to do to get off.

But Judy wasn't interested anyway. "No, you have to hold yourself still over the table if you want me to get you off."

I actually wanted to reconsider whether I could stand it, horrified at how much I wanted to come, but finally said, in a bleak voice, "I can't, Ma'am."

"OK, fine," Judy sounded brisk. "You can change into your street clothes, now, and then do some work at the console. It seems that you need to study some more mental training to keep your mind off sex." Judy sounded like she was enjoying my humiliation! "But I don't want you spending so much time on it you can't get your school work done. From now on you'll get ten slaps when you fail to hand in any homework assignment, and of course you're not allowed to lie to your teachers anymore."

"Yes, Ma'am," I murmured, going to pick up my clothes and change in the bathroom.

"And call me 'Judy' now," she called after me. "Your punishment is over for today." With the frustrated arousal she knew I was feeling after my whipping, I didn't think she even believed that herself.

But somehow I couldn't resent what Judy was doing, since she wasn't as mean as she could have been. I was ashamed to realize that I would have tantalized Judy in the positioner while announcing I wouldn't get her off today if I'd been in charge. Even so, I was a little surprised I didn't resent Judy more than I did. Maybe it was because I was developing a profound feeling of how much I needed her good opinion. As I remembered Judy's speech about pleasing her, I decided I wasn't in any position to resist, and I was going to have to give in and do whatever she wanted. It was a very easy decision to make for some reason, and I felt better after I made it.

-12- Judy

Watching David through the monitor cameras when he got home after his first session was very erotic. To begin with he pulled down his pants to look at his bottom in the bathroom mirror. Hubba was making it look like he had only a pink flush back there, as if from a light spanking, and I could see David's dismay as he realized he wouldn't get any sympathy for how sore he felt. He had a prominent erection when he'd pulled his pants down of course, since he'd had masochistic fantasies ever since Linda Fechtenbaum whipped him. David probed his buttocks with his fingers, and when Hubba masked the soreness he continued rubbing his behind with a kind of dreamy expression, clearly getting turned on. Suddenly he got a guilty, embarrassed look, and pulled his pants up quickly. Obviously he'd remembered I might be watching, and he was embarrassed about me seeing him rub his bottom that way. After a short pause, David went into the kitchen for lunch. Hubba's telltales showed me that he got another erection when he saw Diane bent over the lower Flashing unit. Hubba was set to hold his penis against his belly when he got an erection in public, and I saw David's look of surprise as he noticed. David plumped himself down at the table, probably hoping to cry out and get sympathy, but Hubba continued to mask his soreness.

When Diane sat down and asked David about his session with me, his face got very flushed, and he answered minimally, just that it had hurt a lot and been very embarrassing. Diane got him to admit that his punishment was nowhere near as painful as he'd had from Linda Fechtenbaum, and I could imagine how miserable David felt leaving it at that because the compulsion I'd given made him too humiliated to talk any more than necessary. Even when Diane put him in O-Mode, he was too embarrassed to say anything more than he had to. I was sure this sounded to Diane like I'd handled things perfectly, so there was nothing for her to worry about.

I watched David in his room later, struggling against taking his clothes off in front of the monitor cameras. After several minutes coming to terms with his compulsion, he went to take a bath, showing a constant erection after he undressed. But as I watched I realized he was showing off to me, just like a little kid. He put on a show as he was getting in the tub, flirting his bottom at the cameras he thought I was looking through. Of course after a few minutes in the water David's fantasy play caused Hubba to magnify his erotic excitement with anal and genital stimulation until he started rocking his hips. He suddenly got very red- faced as he realized he had to control himself. He obviously didn't enjoy that part.

David didn't enjoy it when he had to sit down on the toilet later, either! He looked completely humiliated! Almost immediately, Hubba asked me if it should remove the intrusion from David's rectum to allow him to defecate without waiting for his erection to detumesce, but I said I wanted David to use self-control instead. David got impatient and tried to pull Hubba's tentacles out with his hand, so Hubba restrained him. When he lost his temper, struggling to free himself, Hubba stung his rectum at moderate strength with a sound-effect to emphasize it. David cried out, and stopped resisting, so after a few seconds Hubba released him again. Then David sat a long time coming to terms with the situation, before he finally managed to get his erection down so he could evacuate. I felt he'd learned the lesson I wanted, that Hubba could control him even when I wasn't around. I knew that without that control David would try to run away from home soon to dramatize his desire to get out of my control.

When David finally got to put on his leisure suit, I joined Mom for dinner. Afterwards, we watched a Media story about the Mars colony, and spent a little time together. Then I went back to my apartment and did my homework, until David phoned me to ask me to get him off. I explained that he'd get whipped if he pestered me about that; the only time he was allowed to ask was when we met after school. David blushed as I explained the rules, and got even redder when I said I'd enjoyed his strip-show in the bathroom.

I watched him again as he got into bed, enjoying his dawning realization that he had to sleep in the nude -- he'd told me in Deep O-Mode that he always threw off his covers, and I'd reinforced that with a minor com- pulsion so I'd be able to see him naked whenever I looked in during the night. Once he got in bed he went through some slow movements on his stomach that were obviously sexual, before he suddenly stopped and pretended to go to sleep. Hubba told me he was worried I might catch him and accuse him of trying to masturbate. Of course I didn't mind him getting himself excited that way, since it could only frustrate him. He had to use his hand or a peripheral to masturbate, and Hubba was making him too nervous that I'd notice for him to attempt it. At some point I realized that David was so horny he was having trouble going to sleep, so I checked with Hubba that it would help him drop off the same way it helped him concentrate on studying when he made an effort. About ten minutes later, Hubba told me David was asleep.

Watching David moving reminded me about his wake-ups. The surreptitious masturbation variation included daily stimulation to make David wake up humping in his bed. It would normally happen in the morning, when he was so sure he was being observed he'd have to stop, but occasionally it would happen during the night when he'd think it was safe to masturbate. I told Hubba to let me know every morning when David's wake-up was about to start. I thought watching David humping in the morning would be very erotic, especially after I got the sensie line installed so I could experience what he was feeling. I thought about that as I masturbated before going to sleep.

I woke up at six as usual, and read the news while I had breakfast. Then I returned to my room and studied until Hubba told me it was starting to stimulate David. I brought him up on my wallscreen and he was still asleep, lying naked, face down on the bed with the covers kicked off. Hubba started by using some very subtle anal stimulation to give David an erection and encourage sexual dream fantasies; once that was successful, David would never guess Hubba was doing anything unusual when he woke up, since he'd expect erotic dreams would cause Hubba to stimulate him. The enlarged nipple moving in his rectum and the friction in the sheath around his penis would just seem like a standard reaction to his own sexual arousal.