“How was it?” Roberts asked in a small voice.
“I thought you did well,” I said, getting up and putting on my black and floral, silk robe. “That was your first time, right?”
He nodded. His gangly limbs spread across the bed, his bright red cock shrinking back to its usual, unimpressive size. Across his white chest I had left my marks: raised red slashes and round red welts. They looked like footprints in fresh snow. “How did you like it?” I asked.
“It was, eh, was a little scary, at times. Um, but it was interesting. And fun.”
I walked around the room, opening windows and tidying the spots we had rolled, pushed, sprawled, and braced ourselves upon and through. I savored that particular sensation of silk sliding across my skin, especially after sex, especially in the cool night air. The stuffy smell of sex gave way to the crisp summer night air. In truth he hadn’t done all that well. When I first removed his chastity enforcer after our date, he came almost immediately. His penis skin could have been made of felt, it was so soft. Embarrassed, of course, he tried to make an awkward exit, but I instructed him to go make us a snack in the kitchen. Bless his heart, he made us grilled cheese in the waffle iron.
When his jumpy, mealy-mouthed chatter subsided, I made another move. He was eager if nothing else. Happy to follow instructions, happy to listen, but very little initiative, almost no passion. In short, he fucked not like a man but like a boy. Which, hey, that’s fair enough, sparkly new virgin that he was.
His eyes followed me as I moved around the room. I caught his gaze every now and then. “What?” I asked coquettishly. His look was intrigued but somewhat concerned. “I don’t know,” he said. “Some of it was kind of weird.”
“Like what?” I asked, sitting at the edge of the bed, letting the front of the kimono hang low and open below my breasts. He sat up with legs crossed like we did in kindergarten, his little dick retreating into itself. “I was doing what you asked,” he said softly, avoiding my gaze, “but you kept hurting me.”
I chuckled softly, gently, caressing the patchwork markings I’d left. “I wasn’t really hurting you,” I said, “it was just to turn you on. Get you going. None of them will be there in a couple hours.” Except the hickeys, which would probably bruise. I didn’t even want to see his back, where I did most of my clawing.
Roberts sort of pulled away and scooted to the other side of the bed where he let his legs hang down. “And I feel weird about the last thing.”
“The last thing?” I inquired. “Like when I was playing with your ass?”
He nodded, shoulder slumped in shame.
“Aw come on,” I said, crawling across the bed to him. I laid my head on his lap, right over his glistening member. “Lots of guys like it when I put something in there. I usually do more than a finger.”
“Well I didn’t like it,” he responded.
“Did it make you feel,” I bit his thigh, “violated?”
He jerked with a whimper of pain. “I don’t know. I guess so. It was just, mm, it was weird.”
I was on my knees, rubbing his back, my fingers bouncing across the furrows I’d left there. “Don’t feel bad. It’s just a normal part of sex. Do you want to know what I think?” He sort of sniffed and looked at me. “I think you actually liked it. I mean, you got way harder and you started humping me so much better. I thought it was great.”
“Do you mean that?” he asked, eyes searching for validation.
Training a boy is like gardening. You can never create something totally new. You find your patch, with its overgrowths and twisting vines and you start to prune. A bit here, a bit there, you trim and cut back, and then you encourage growth and development. I could never have made Roberts into a total sissy if the sprouts weren’t already there. All I had to do was prune back the bravado and immaturity, the hang-ups and misgivings, and it was only a matter of letting his dependence and submissiveness grow. With a little love and constant caring, I could coax out the best parts of him, and start to mold the sissy I always wanted. Of course, it’s easy to talk about in the abstract. In reality, the process is never straightforward, as there are hidden snags and deep neuroses. Nor was I the only person making decisions here. Like it or not, Roberts could choose his own path in life, and at times it didn’t seem like he could be the person I wanted him to be.
School was over in a fall and Roberts had been so busy chasing skirts that he hadn’t planned properly. Since he wasn’t going to university and he didn’t have a job (well, he made pizzas), I found it necessary to step in. The first thing that had to go was his nasty shitbox car he had bought with pizza money. I couldn’t stand the embarrassment of having that thing outside of my house at night (never in the driveway because it leaked). But in order for him to give up the car, he had to have transportation from his home and job. So I moved him in with me and found him a job in my office, in the mail room. That way I could drive him in my nice Desrail, the shitbox could be retired, and I could keep tabs on his comings and goings. And yet, for all that forward progress, he still insisted on bringing his taped up, busted skateboard in the trunk. Sometimes his pack of “homies” would come by work and they’d skate around the industrial park on his lunch break. From what I could tell none of the others had jobs at all.
Donna from the mailroom came to my office in a huff less than a month later. My office boy sat her in an armchair in the visiting area of my office. Even though Donna was technically a few ranks below me, she held a similar administrative position in her department and I treated her with respect. “I know you like him, I get it, and it’s not the first favor I’ve done of this kind–hell, it’s not even the first of its kind I’ve done for you, but the boy is completely useless. I really–there’s nothing I can do. I can’t use him.”
“What’s wrong?” I asked, getting a coffee from my secretary for each of us.
“He don’t pay attention to anything. He sorts shit wrong. He delivers things to the wrong people because he’s not paying attention. Seriously, I tell him what to do and his eyes are completely vacant. There’s nothing going on in there.” Donna was already an anxious woman, but when she wore loose, flowing blouses, as she often did, and talked violently with her hands, she was a self-contained tropical storm of heaving waves, threatening to overwhelm you with her sea problems. She had a rosy pink nose and a blotchy complexion. You could just imagine the cartoon steam billowing out of her ears and nose.
I spoke low and slow to try and bring her down to my level. “I understand that you’re frustrated. I don’t want to make your life harder just so mine can be a bit easier. Is there anywhere else he could be useful?”
Donna shook her head, her chins following after, “I already have him working the dumbest, easiest job in the place. Literally all you have to do is pay attention. I wouldn’t trust him with anything else.”
“Is there another department, maybe?” I asked. Donna pondered on that while my secretary organized the papers on my desk. “Don’t mix up Dole with Dillow,” I reminded him.
“HR always needs paper pushers,” she suggested, “but that’s certainly more involved than sorting mail. I mean, can he even write? Sorry, that was rude, but really. You know, there’s always,” she glanced towards my secretary, specifically at his ass as he bend across the desk. I shook my head, starting to talk, but she beat me to it, “I know, you need someone competent. Me too.”
I realized that I would need to get more involved. This kid wasn’t just a mess sexually, he didn’t have his life together. I figured that if he couldn’t work like a man, he could still serve as a houseboy. In the confines of my house I could train him up before introducing him to the wild again. With young boys the fun is being able to mold them exactly how you like, but with that comes a responsibility to train them properly.
I had hoped my latest project would be somewhat self-sufficient, but it seems that his mother taught him nothing. I had to teach him each of the chores in a somewhat laborious process of leading him around by a leash and securing him in the area needing improvement. After an hour or so, I would check on progress and administer corporal punishment if necessary. I don’t personally take pleasure in inflicting pain, at least not the physical kind, so I didn’t really enjoy the process, and Roberts clearly wasn’t pleased either. The way he wailed, you would think he had never seen the flat side of a paddle before.
During this time our sex life changed a bit too. Roberts had so little in his life to lose, it was hard to find leverage to keep him acting right, so I found it necessary to institute certain rules. Early on, I let him cum in me twice or three times a week. I now instituted a rule that he would be allowed to have sex each week on Sunday if he was very good. Of course, for a youth of his age, only once a week is not often enough to prevent him hurting himself in the enforcer, so he was allowed four hours of personal release time per week that he could use whenever he wanted. From what I can tell, he was masturbating about once a day, which honestly wouldn’t bother me if he was getting his chores done. Unfortunately, he was not getting his chores done often.
“Can I have my release time yet?” he whined in that particular teenage way.
“Did you finish the dishes?” I asked, not looking up from my magazine.
He rolled his eyes. “I just cooked. Can’t I do them later?”
“No, you can do them now, and you can get release time later. That’s how it works, remember?”
He sort-of stomped off and huffed around the kitchen for a while. When he came back he was getting red in the face. I couldn’t help but notice how hilariously cute and tiny-sounding his stomping was. “I wish I’d never given you my key. I never had to deal with this from my mom!”
It was my turn to roll my eyes. “Maybe that’s why you’re such a spoiled child. I mean, come on, Roberts. You’re an adult now and you’re throwing a tantrum like a baby.” That seemed to shut him up. On his way out of the room, I called to him, “Roberts, there’s a glass.” The wineglass sat on the table before me, so he had to walk all the way across the room and come right up to me to retrieve it. We had a strict ‘no male clothing’ rule in the house, so he opted to wear nothing. I resisted the urge to tug on his little cage or slap his ass as he walked by. “Thank you,” I said when he picked up the glass. He only glowered at me.
I heard the glass on the kitchen counter, but instead of the sound of water running, I heard the pad of his feet across the hardwood of the front room, up the stone stairs and the closing of the bedroom door. I didn’t let his disobedience bother me, I just kept reading.
When he returned about a half hour later he went straight to the kitchen and started washing. I came in behind him and found him wearing my favorite of his panties, a pink lacy number that showed off his tight ass in the best light. “How was your break?” I asked.
“Huh?” he asked, eyes all wide and innocent.
“What were you doing up there?”
He looked back at the dishes and said noncommittally, “Cleaning.”
I could have laughed if I wasn’t so annoyed. “And what did you clean?” I asked.
“You know. Made the bedroom look nice.”
I was right behind him now, watching his washing over his shoulder. I felt the outline of the panties, two bands across each ass cheek, meeting in the middle and sliding down, all the way around his pert ass, up that warm crease between his legs. I grabbed his balls lightly and kneaded them around. “Are your guys feeling sore? You didn’t get any release yesterday, did you? Why was that?”
“I was bad,” he muttered.
I removed the panties, sliding them down slowly and lifting his feet out of them. Finally I caught a glimpse of his caged package. “And what the fuck happened here?” I demanded. His enforcer was all fucked up. His balls glistened with lube where he had slid it off without the key, and his cock was not at all seated in the plastic tube. I always made sure his enforcer was properly installed every morning, and this was not my handiwork. “Seriously, answer me, what is going on?”
“Well, I asked first,” he said, lower lip jutting defiantly.
“This is absurd,” I said, giving his balls a hard slap. “This is ridiculous. You’re like a child. Just an annoying little shit. I’m too old for this shit. You’re not serious about this relationship.”
Things went downhill from there. As soon as I threatened to throw him out, suddenly he was singing a different tune. Suddenly he loved me and needed me and please please how will I live, where will I sleep, etc. His sniveling only annoyed me. By the end he was sobbing.
“Just hush. Please. Just shut up your bullshit and get out of my house. You don’t live here anymore. To live here, you need to make your own money, or you can work for me. You don’t get to laze around all day and then disobey me at night.”
Eventually he gave up protesting and made up his mind. “That’s fine,” he told me, one bag of clothes under his arm, his panties clearly showing through his tights. “You think you’re so great. Women would love to be with me. I could find someone else in a week.”
Somehow he didn’t find it suspicious that he did just that.