Trainingware Pt. 08

I guessed odd, and the number that came up was 12, so that meant I was going to get 20 slaps again tomorrow. I thought hard, as if that made any difference to a random choice, and guessed odd again, then saw the number 53 come up. I started to go the rest of the way to climax, but after I'd been at it for about thirty seconds, I suddenly heard a voice through the monitor annunciators.

"O-Mode. Freeze in that position, David." It was Judy's voice, and my heart went into my throat!

"I've caught you at it! You've been a VERY bad boy!"

I'd frozen in place with my behind in the air at the high point of my humping motion, about to thrust my hips down again, and my position made my embarrassment even worse. Stroking off was such an intensely private act that I felt guilty about doing it at all in front of cameras that Judy could watch later, but having her actually catch me in the act was the most humiliating experience I'd ever had. Through waves of shame, I heard her speak again.

"I'll give you your whipping tomorrow morning, but I want to teach you a small lesson right away, so I'll have Hubba whip you!"

A harness of Hubba's tentacles formed over my shoulders and passed below my body to wrap around my knees. Then my arms were bound together in front, around chest level, and my knees were pushed apart. Finally, the harness tightened, pulling my knees up toward my shoulders, leaving my behind protruding. Judy dropped me out of O-Mode, but I still couldn't move or even rock myself over on my side because of the way my knees were splayed. Then I felt something like a cat of nine tails whipping my buttocks, seeming to cut into my flesh, and I started wailing immediately. The whipping kept up for what could only have been twenty or thirty seconds, but felt much longer, and I nearly peed myself while it was going on. It was completely different from the way the wand felt: the multiple tentacles were so thin, and stung me in an entirely new way! After the whipping stopped, I was crying for another thirty seconds, and then Judy spoke again.

"You won't be able to reach climax now, David. And you have ninety slaps coming tomorrow, twenty for the hurdle you lost, and eighty because I caught you at it. I'll let you out of ten for the punishment you just had. Come to my house in the morning right after you wake up and take your shower!"

Suddenly, I felt Hubba's tentacles release me and I was free to move again. I felt very vulnerable as I pulled the covers up over my body. Judy was even going to count the bet I lost on the first hurdle, although I'd never really had a chance to succeed! I realized she'd probably been watching me trying to stroke off the whole time I was doing it, so she'd have a chance to give me more slaps for any hurdles I failed! Then, if I succeeded, she could just interrupt me and keep me from getting off anyway! I groaned with frustration, then felt a recurring wave of intense embarrassment remembering Judy catching me in the act. I tried to stop squirming and lie still, then did mental exercises until I finally dropped off to sleep.

Saturday morning, I got to Judy's apartment at seven-thirty, feeling a confusing array of emotions. I'd never been so horny in my life when I wasn't being stimulated in some way, and of course I was scared of the whipping I was about to get. But almost as strong as those feelings was my desire to get across to Judy how sorry I was that I'd misjudged her. As I stepped in from the door I said what I'd thought out before Judy could say anything.

"I'm sorry, Judy - uh, Ma'am, that I've been so resentful and mean the last few days." I saw Judy's intent expression, and faltered a bit. "I . . . played your sensie ADT last night, so I know I was wrong about what I thought." Judy smiled then, and I felt better. "In fact, I realize I should be grateful for what you did to keep me from more severe punishment, and I want to apologize that I didn't believe you before." My phrasing was kind of stilted because I'd been thinking of what to say since I woke up, and I worried I was sounding phony. "I know this sounds like I'm sucking up to you because I've got a whipping coming and I need you to get me off so much . . ."

"Not at all," Judy interrupted. "I can always tell when you're not telling the truth, remember. I'm happy you're not angry at me any more, and I accept your apology." She stepped toward me and gave me a little hug, and I started crying with relief, but I was so horny that within a few seconds I was trying to rub against her, and she stepped back.

"None of that, David," Judy said in a teasing voice. "You still have a whipping coming, you know."

That deflated me effectively, but it didn't actually cause my erection to shrink, and when Judy looked significantly at the dresser containing my punishment outfits, I went to take off my clothes and put on the shorts. I wasn't able to turn completely away from Judy to hide my erection, and I was still enormously embarrassed about that, even more for some reason because of what Judy had caught me doing last night.

Judy told me to go get on the positioner, so I only had my shorts on about ten seconds before I had to drop them again and climb into position, trembling a little.

"I can experiment with how I punish you for masturbating, David, as long as the full session motivates you not to do it again. This round I'm going to try setting the sex-surge higher and higher as I go along."

Judy started the warm-up, and I was shrieking when the real slaps started. They didn't feel any different than usual, and I was bawling pretty early because I was still sore. But after a while I started noticing how sexy the slaps felt! They seemed just as hard as before, but I was interpreting them differently, as if I was getting a micro-orgasm with every slap. It became more and more sexy as it continued; my behind felt like a huge sex organ with Judy doing harsh but exciting things to it. My cries didn't get any quieter as this went on, but the tone of my voice must have changed, since I didn't know myself if I was crying with pain or excitement. When Judy stopped the slaps, my cries turned into pleading for the climax Judy could give me. I didn't really expect Judy to get me off in the middle of a punishment, but I wasn't very rational at that point. At the end of the whipping round I'd been feeling sensations I'd always associated with climax.

The positioner came down and released my restraints, and I stood up rocking my hips and gritting my teeth to keep from touching myself. I was completely oblivious to everything but the throbbing arousal I felt everywhere below my waist, and Judy had to speak loudly to get my attention. She told me to follow her over to the sofa and get over her knee in paddling position. I was terribly afraid of more frustration, but by now I'd used hours of mental exercises to make obedience automatic when Judy told me to do something, so I didn't hesitate following her. I got over Judy's knee and she told me to get my bottom up, then immediately grabbed my cock and started stroking it, goosing me at the same time, as she had Tuesday. I started humping galvanically and was back up to my normal orgasm level of Arousal almost immediately -- then I started moving quickly up through the new range of sensations I'd come to expect as part of my sexual rewards. I felt more and more intense excitement as these sensations progressed, but I was expecting Judy to stop at any second and leave me frustrated.

Then I suddenly exploded, screaming my head off as I ejaculated and relieved the frustrating pressure that had built up for the last three days. After a long mindless climax, I fell down bonelessly on Judy's lap, then lifted up quickly, remembering that I'd decided not to pass out over Judy's knee again.

Judy put her hand on my behind and rubbed it in a gentle way that still emphasized the soreness, then said, "You were so horny I decided to let you come, David. But I don't want you to think I'll always go this easy on you. I liked the way you apologized, so I thought I'd give you a reward. Let's have breakfast now, and when you've recharged your batteries I'll finish your punishment."

I understood I was going to get whipped again later, but at least Judy wasn't going to do it right after my climax. That would be extremely mean, since I wouldn't be able to sublimate any of the pain in sexual excitement. It would be like using a strong negative sex-surge on the punishment wand.

I suddenly realized that Judy had taken pity on my sexual needs right in the middle of a punishment session, an act of mercy I'd never expected, and I wanted to express what I felt.

"Could I . . . kiss you?" I asked Judy tentatively. "Just to thank you for getting me off?" I paused, then added, "You kissed me on Tuesday, and I don't have any sexual motive right now, so I thought it might be all right with Hubba for me to do it back."

Judy looked pleased and got the distant look she had when she talked with Hubba. Then she got us both standing up, and moved close to let me kiss her. She joined in when I started, and gave a happy little moan at one point, but it was mainly me controlling the kiss. I was still naked of course, but I wasn't as embarrassed as I had been, and I tried hard to avoid any contact between Judy's erogenous zones and mine. At the end I slowly began feeling embarrassed again as my erection started trying to make a reappearance, and after Judy saw me flushing she told me I could go put on my shorts.

She served a great breakfast, Eggs Benedict with Blue Mountain coffee, and Crepes Suzette for dessert. The coffee was a fabricant duplicate of Jamaica Blue Mountain, and most of the fat was a levulo isomer so it wouldn't stick to us, but I couldn't tell the difference from the real kind myself. By the end of the meal I was being careful not to stuff myself, and beginning to feel a little apprehensive. I was due to get the rest of my whipping when I felt aroused again, and three days without sex was catching up with me: I'd had a sensitive, rock-hard erection for the last ten minutes.

Judy stood up and told me she was going to use the bathroom, and I might want to use the one across the room before she continued my punishment. I obediently went to the bathroom, and after I finished urinating, Judy took several minutes to come back. I got more and more apprehensive as I waited for her; by the time she came in I was red-faced, moving from one foot to another as if I needed to use the bathroom a second time. Judy made my punishment shorts drop off and obviously enjoyed watching my blazing face, then told me to get back in the positioner. I was scared again, since Judy had said the session would motivate me not to masturbate again, and I knew I hadn't had much negative reinforcement so far. Once I was restrained in the positioner, Judy asked me if I wanted to substitute some alternate punishments for some of the sixty slaps I had left, and I agreed eagerly. I felt Judy move the positioner to an arousal position she'd used before, but with my torso slanted slightly up to make it easier to look in the wallscreen. Judy told me to watch the screen and it would remind me of what I was being punished for, then started a vid clip of me in my bed the night before.

The clip showed me naked in bed, starting to hump in my sleep. It was so embarrassing to see myself like that, with a view of Hubba thrusting it's tentacles in and out my rectum, and me getting more and more spasmodic until I finally woke up. I saw myself look closely at my bedside clock, then turn around to look at the monitor cameras with such a flushed and guilty expression that I cringed with embarrassment. Then I started to stroke off in the clip, and the system kept changing the angle of view between different monitor cameras, views from above and then from the side, focusing on my behind humping up and down with Hubba's tentacles moving in and out, switching to my face single-mindedly concentrating on getting off, and occasional views of my cock thrusting into my hand.

Judy suddenly announced that Hubba was going to duplicate my sensations in the vid clip, and when I felt Judy's fingers on my cock I gave an embarrassed cry and started humping in the positioner, watching myself doing the same thing on the wallscreen. The clip must have skipped forward a few times because it seemed only a few minutes until I reached the first hurdle. Just as that happened, Judy came up to the positioner and rubbed my behind a little with her hand, telling me what a naughty boy I was, and asking me if I was sorry I'd been so bad. I was whimpering with excitement as I watched myself failing the first hurdle.

Judy started warm-up slaps while I was still guessing hurdles in the vid clip, and when I heard Judy's voice telling me to freeze in that position, the clip froze and the positioner moved me back into punishment position, while Judy started giving me full whipping slaps with the wand. I was shrieking immediately, and bawling after about ten slaps. Judy kept it up for thirty slaps, and at the end I took nearly two minutes to stop bawling. Then she stood next to me for a few minutes while I felt returning sensitivity stinging my behind, and began the question-and- answer I hated so much.

"Are you sorry you tried to masturbate last night, David?" she asked, and gave me a slap.

"Yes, Ma'am," I cried out right after my shriek of pain.

"Are you going to do it again?"

And of course I didn't know how to answer. I didn't want to say I was going to do it again, but I knew I would if I thought I had a chance to get away with it. So I couldn't say I wasn't going to do it again, since I'd be lying and Judy would catch me. After hesitating a few seconds, Judy gave him a couple of slow slaps, speaking over my shrieks to order me to answer.

"I can't help doing it, Ma'am," I cried, when I could speak again. "I get so horny, and you've given me a chance to get away with it sometimes, so I just can't resist!"

"You could just stop masturbating and depend entirely on my rewarding you when you've been good!" Judy answered in a strict voice. "Don't you want to be good?" And I got two more slaps.

"Yes, Ma'am," I shrieked, unwilling to wait until the effect of the slaps died down. "I want to be good. I'm sorry Ma'am."

Judy paused for a moment, and I felt my buttocks wince whenever I heard her move.

"All right, David," she said. "I suppose I just have to wait until you learn better. But I'm going to help that along by having Hubba tantalize you for ten or fifteen minutes to end your session." There was a short pause for effect, and then she added, "I'm going to let you touch yourself with your hand, and you'll have a small chance to reach climax, about one in ten if you manage to come up with sufficiently erotic fantasies to get yourself off. But most likely you're just going to end up feeling very frustrated at the end. Then I'll have to decide whether to leave you that way until tomorrow."

Judy snapped the positioner into the arousal position again, and I felt Hubba start to tantalize me anally. I realized my right arm was free and I could reach down under the positioner and stroke myself. I tried to resist doing it, because of how likely it was that I would just be left frustrated at the end, but pretty soon I couldn't stop myself, and was amazed again at how embarrassing it was to do this in front of Judy.

I felt Judy's fingers as I stroked myself, and soon I got up to the level where I would have reached orgasm before Judy's training. I was trying to come up with a good fantasy, thinking about Judy watching me do this and how humiliating it was, and then I realized the positioner I was on must have been moved in the last few days, because I could see Judy leaning back against the table, facing me in one of the wall mirrors. The reflection of her head was cut off, but I could see her body from the shoulders down, watching me on display as I tried to masturbate. I got more aroused when I saw her watching me, and began humping frenetically against the tension in the positioner, fantasizing for all I was worth about Judy seeing me like this. I imagined how she might be monitoring my sensie to feel my sore behind and experience how aroused I was, and I was able to get maybe half-way through the new range of sensation, but I couldn't get all the way to climax, and I finally dropped back from that level of sensation, feeling terribly frustrated. Judy had made it clear I only had a one in ten chance!

Suddenly I saw Judy's image in the mirror stand away from the table and drop her shorts, then start stroking her pussy with her hand. I felt a new surge of arousal as I realized that since I couldn't see Judy's face, she didn't know I was watching her! After a minute Judy pulled off her top, and I felt supercharged from seeing her naked body! Then she turned away from the positioner and bent over the table with her rear sticking out and her legs spread. Her fingers were stroking her pussy, perfectly visible in this rear view, and her hips started to move up and down almost as quickly as mine.

I felt myself go nuts with arousal, watching Judy greedily to draw every last bit of erotic energy out of what was happening. I was moving closer and closer to climax, and when Judy suddenly shuddered and moved galvanically in an obvious orgasm, I felt awful that she'd been so quick and I hadn't had quite enough time to reach climax myself. Then I saw that she wasn't stopping, and I realized Judy must have multiple orgasms! I still had a chance! I kept watching Judy masturbate, thinking about her thinking about me, and each time she had a new orgasm I was a little closer, until finally, as what I thought was her fifth orgasm started, I exploded, screaming with release for the second time that morning. After her final galvanized thrusting stopped, I saw Judy turn around and pull on her shorts and top again. Then she walked up to the head of the positioner until I could see her looking at me as if she suspected something.

"Did you get off?" she asked.

"Uh, yes," I said, in what I thought sounded like a guilty voice. If she asked me the right questions, I'd have to tell her what I'd seen.

But Judy laughed, "Well, congratulations on succeeding with your one in ten chance!" Then Judy lowered the positioner and released my restraints, and I was free to get dressed.