Chapter 1

Thomas Milford Stout should have been a lucky boy. He didn’t feel lucky, though. He was heir to something known as the Stout fortune, although he didn’t really realize at his tender age what that consisted of. Lots and lots of money was all he knew. The property and stock holdings didn’t interest him yet, but the money did. But the problem was that he was a kid and he couldn’t get his hands on it. And he had some probably realistic fears that somehow he’d be shut out of it before his time came.

But his biggest problem was Mrs. Crane, his guardian. She had been a friend of his mothers and for reasons unknown, in his parent’s will she had been specified as first choice to raise him should something happen to his parents. And sure enough, something had happened to his parents. During an airplane ride to survey some project his dad was involved in somehow a building had gotten in the way of the airplane. It was still remarked about in the news. Thomas knew exactly what had happened to his parents. They even drove past the building occasionally and he could see where the new parts of it didn’t quite match the color of the old parts. Crazy. It made him sad.

Mrs. Crane made him sad, too. She was a harsh guardian. In spite of coming from a genteel background she was severe and strict and in his mind he called her a nazi. She was strict beyond reason and just plain mean. She was totally anal about things like his room and every day he had to pick up things and make his bed. He wasn’t allowed down to breakfast until she had inspected the room and everything met her strict standards. Good god, he thought, I wish this woman had had kids of her own so she had something to focus on other than me.

Her husband was a meek mouse of a man and was no help. He was as harried and henpecked as Thomas. More so, probably. Although Mrs. Crane was attractive, Thomas could no more imagine the Cranes having sex than elephants flying. Although ... if that’s what she wanted ... Mrs. Crane usually got what she wanted. She had a strong will that could not be denied. And here’s the weird thing, as far as Thomas was concerned. For all her bitchiness, Mrs. Crane was a very attractive woman. She was maybe in her early forties and had a nice figure. Her waist was still slim and her hips and butt looked great ... she hadn’t started plumping out like most women her age. Her face was beautiful, although she almost never smiled. She worked at keeping her figure, their home had a small gym, and she spent an hour a night in it, working out or running on the treadmill. Thomas harbored a secret fascination with her, he watched her carefully, and, deep in his heart, he even lusted after her. Well, Thomas was that age where he lusted after anything remotely female. If she just wasn’t such a bitch, he thought.

Sex was a big part of Thomas’s life at the moment. Not actually having sex, he figured he was years away from that, he was never allowed around girls anyway. Sex, to him, meant basically jacking off. He had discovered his ability to ejaculate a year ago and become quite an expert at it, as most young boys do. It consumed much of his time although he was very careful not to get caught at it. Luckily his door had a lock.

Thomas lived with the Cranes in their mansion in the Hamptons. Their butler, Worthington, took him to school every morning and brought him back in the afternoon. He was hardly ever allowed to have company, another thing that pissed him off. Mrs. Crane was also very reticent about allowing him to go to his friend’s houses. Sometimes he felt all alone in the world ... most of the time, for that matter.

One day Thomas got in trouble. Major trouble. Mrs. Crane often searched his room for contraband during the day when he was at school. He knew that, and he had several hiding places that he thought were safe.

A friend at school had given him a sexy magazine, something named Beavers Galore, and he had hidden it in the center of his bed, inbetween the mattress and the springs. He knew she ran her hand inbetween the crack between the springs and mattress, but so far stuff in the very center of the bed was safe. The most damning thing by far, moreso than the magazine, was a pair of Mrs. Cranes used panties, something he had stolen from the laundry room a few days ago.

When Worthington brought him home from school that fateful day, he knew he was in trouble just from the stormy look on her face. His first thought was the magazine, and sure enough when he checked his hiding place the magazine and panties were both missing. His heart stopped for a moment, and he sighed. He knew this one would be bad. He changed clothes and slowly went back down the stairs to the dining room at dinnertime.

Dinner was not pleasant, though no words were spoken to him. After dinner she tersely motioned Thomas to accompany her. His heart sinking even further, he followed her to the study and seated himself. She launched into him immediately.

“Thomas. You have failed me again. You have proved your unworthiness to deserve the fortune your parents so foolishly left in your name. I have done what I could to raise you properly, but it appears I have failed.”

She reached in a drawer, and withdrew the offensive magazine. He winced at the slutty woman posing on the cover with her legs far apart. He knew doubly this was going to be bad. It was.

“Thomas, where did you get this ... this smut.” she asked, shaking the magazine in his face. He pinched his lips together. He wasn’t going to rat his friend out.

“I found it in a wastebasket, at school,” he finally said, when, as was her habit, she just sat and stared accusingly at him, waiting for him to speak.

“Well, that answer will have to do. Although I’m sure one of your nasty little friends gave it to you. That, however, is not the real issue here. That is not the real problem. Your unholy perversity is the problem. And I have proof of it, here.”

Once again she reached in the drawer, and triumphantly withdrew the culprit. The pair of her very own soiled panties. A pair of panties that she had obviously worked out in the gym in, judging by the sweat-stained appearance of them. She hadn’t dared to sniff them, but she was sure they were aromatic, probably offensively so. She waved the panties in front of the evil boy.

“What is this, Thomas? What have we here?” She stood, and approached him, holding the panties in front of her like Van Helsing approaching a vampire, his cross at the ready. “Who’s are these? Could they be mine? What are you doing with a pair of my panties under your bed?”

She stopped, and pressed the panties to his face. She positively scrubbed his nose with them. He sat, solidly, not wanting to give her any satisfaction.

“My, my, Thomas, what a naughty boy you are. Stealing a pair of my underpants for your nocturnal activities. What do you do with these? Do you sniff them, as you touch yourself?”

He was silent. She scrubbed them in his face some more. To his horror, he felt his penis begin to harden. It was sexy to him, to smell her sweaty pussy smell, and know it was her holding the panties to his nose. This was the thing he’d done every night since he’d gotten them, and here she was doing it to him. He hoped she couldn’t tell if he got a hard-on.

“Do my panties excite you, Thomas? Do they make your ... manhood stiffen? Does it feel good? What a little wastrel you are, spending your life in such base pursuits as sex. What a naughty little boy, playing with your pee-pee. You should truly be ashamed.”

She finally finished, and threw the panties in his lap. “I care no longer. I have tried my best, and I see that it is not good enough. Your perverse animosity to my concern for you is more than I can bear. I wash my hands of you. You must survive on your own, now, without guidance from me.”

Oh, he thought, if only that was true. He knew this shit. She’d said all this before, pretty much verbatim, last week when he forgot to take the garbage out, his one single chore around the house. He knew she’d be right back on his ass in a day or two.

“Thomas, go to your room. This is a severe offense. One which calls for corporal punishment. You leave me no choice. Go to your room and wait for me. I must assemble my ... equipment.”

He had no idea what that meant, but he was glad to escape. He dropped the panties on the floor and fled back to his room. He locked the door, knowing he wouldn’t have the nerve to keep her out when she came. He sat on his bed and pinched his hard cock. Yep, he thought, that was pretty sexy, getting to smell her pussy at her hands.

Thomas wasn’t that afraid of Mrs. Crane. She’d never touched him in the three or four years he’d lived here. He did wonder, though, what she’d meant by equipment. Was she going to finally spank him? Had he crossed the line on this one?

An hour later she knocked sharply on his door. He opened it and she entered. Oh, shit, he thought. In her hands was a riding crop, like what jockeys used on horse. And a bottle of lotion. And, the weirdest of all, two pairs of handcuffs. She was wearing a knee-length black skirt, and a white blouse. Her feet were in a pair of high heels. He could smell her scent, the perfume she usually wore. She actually looked pretty good, if she just wasn’t such a bitch, he thought.

“Thomas. The moment of your punishment has arrived. I expect perfect timely obedience from here on. Don’t make it worse on yourself.” He nodded. He just wanted to get this shit over with. He knew it would probably hurt a little but he thought he could stand it.

She stood at the foot of his bed. “Come here,” she said, and he cautiously approached her.

She took one of the handcuffs and held out her hand. He slowly held his hand out and she clicked it on him. She reached down, his arm following her, and clicked the other end of the handcuff on a rail that ran along the bottom of his bed. Oh, shit, he thought. I’m going to be helpless.

The other hand soon followed. He faced his bed, his hands grasping the rail. He was glad he had jeans on, he thought they would protect him some from her whip.

That was not to be. With a satisfied noise, she reached around him, and he felt her fumbling with the snap to his jeans.

“Hey...” he said, and she froze.

“Thomas,” she said, “I said, do not make this worse. You have caused me to have to do this. Do not irritate me further.”

He was silent. Shit, he thought, for the hundredth time. Shit. This did not look good.

She got his pants unsnapped and drew them down his legs. All the way down to his ankles. Damn, he thought. Just past my butt would be enough. But it wasn’t to be. And then, she just blew his mind. He felt her fumbling along the waistband of his undershorts, and she pulled them down. All the way down, too. He stood before her, bottomless, his ass exposed. He felt his face burning in shame.

“Now,” she said. He heard a slap, as she slapped the riding crop on her hand. “Thomas. This is an opportunity for you to take your punishment like a man. Let’s see if you can be more of a man than Mr. Crane. He often cries out.”

That surprised him. She whipped her own husband? For what? That was just almost weird that she would say a thing like that. In his mind, though, he had no problem imagining her whipping the man. What a fucking nazi he thought for the thousandth time.

The first strike wasn’t that bad. I can stand this, no problem, he thought. The second stung a little more. And she positively hit harder on the third. By the tenth he was squirming and she stopped for a moment. He froze and she struck again.

He finally lost count. He just stopped counting as stroke after stroke fell on his tender ass. He could feel the burn and it got worse and worse. When she finally stopped he was almost to the point of crying out.

He jumped, then, feeling her hands on his body.

“Thomas, because of the severity of what you did, I’m going to punish a very specific part of your body. Remember, you did this, not me.” she said, and he felt her hand between his legs. Her other hand she put in the middle of his back, and pushed down, hard. He almost fell on his chest on the bed, his ass still in the air. She now had his testicles in her hand. She pulled them out between the back of his legs. He felt his cock begin to harden, in spite of everything. She had pulled his balls out so far, his cock was sticking straight down, and was also almost out the back of his legs too. He knew she’d be able to see it without looking too closely, and he hoped she didn’t notice it’s hardness. His mind was a jumble of emotions. His ass still burned, and he was embarrassed and pissed off, but the feel of his ballsack in her hand was really exciting him.

“Thomas, this will hurt, but it will not damage you. Remember, you did this.” she said, and he felt the crop lightly smack him on his balls. It did not sting, it did not even really hurt at all. It was almost like she was playing with them. She did it five times, and then released his balls and stood up.

“There. Consider that, next time you are tempted to raid the laundry basket for my panties. Remember what it will get you.”

She unlocked the handcuffs, and he stood. He didn’t want to turn around and face her because his penis was uncomfortably hard by now. He reached down for his pants and undershorts but she stopped him.

“No!” she said. “Thomas, turn around. Face me.”

He didn’t dare. He was afraid seeing his cock would enrage her. He heard her slap the riding crop on her open palm, again.

“Thomas ... this doesn’t have to be over...” she said warningly.

He slowly turned, his body still hunched over like it had been when he had reached for his pants.

“Stand up, Thomas,” she said. He slowly raised up straight.

“Ha!” she said. “Just as I thought. Did that excite you, Thomas? Did getting your little balls spanked turn you on?”

He was silent. It had, but he’d be damned if he let her know.

“I see we are going to have to work on this problem. You are well on your way to becoming a pervert, just like my husband. We must nip this problem in the bud.”

She stared speculatively at his hard cock. He felt it twitch. It was turning him on big-time to see her looking at him. He was, for a moment, proud of his cock. He wondered if her husband’s cock ever got this hard.

“I will think on this,” she finally said. “I have some ideas. I believe I can straighten you out. Now, lay on your bed, so I can apply this ointment to your bottom.”

Oh shit, he thought, all this and I’m getting an ass massage, too. He turned to his bed, and lay across it, pressing his hard cock into his belly. She approached, and he felt something cold on his ass as she squirted lotion on it. He felt her strong, hard hands rubbing it into his hot butt. That, at least, felt good.

To his surprise, she actually apologized for whipping him. She talked quite a bit, as she rubbed his ass. To his absolute shock, she spread his legs with her hands, and he felt her rubbing some lotion into his ballsack. Damn ... that feels pretty good, he thought, wishing his hard cock were pointed down, instead of up along his belly. The feel of her hands between his legs was unreal as she rubbed the slippery lotion into him.

She finally gathered her equipment and went to the door.

“Thomas. Expect a visit from me. We will begin your ... re-education after school tomorrow.”

Shit, he thought, breathing a sigh of relief as she left the room. He hurriedly shut the door and locked it. Within moments his hands were on his hard cock. He went to his bathroom and solemnly jacked off into the sink, thinking of the feel of her hands on his balls. He wished she’d took his cock into her hand. That would have been too much. At last he sighed and groaned and shot a giant load of cum into the sink. He felt much better after that.

He spent the rest of the evening planning his revenge. Sadly, it was just plans, he couldn’t really come up with anything. It was damn hard to get leverage on the woman.

He had almost forgotten about his “re-education” by the next day. But he hadn’t forgotten her hands on his balls. He’d masturbated again that night and then the next morning, remembering the feeling of her hot hands on his ballsack. She’s touched my balls, he told himself, she held them in her hands. It really turned him on.

After dinner, she sent her husband to the kitchen with the used dishes and turned to face Thomas.

“Thomas, go to your room, please. And think of your wayward path as you wait for me.”

Oh shit. He trudged upstairs and sat on his bed. He didn’t even bother to close the door this time. She showed up fairly quickly and, to his secret pleasure, she had the whip again, the lotion, and ... weirdest of all ... what looked like a pair of her panties. Another pair, not the pair he’d stolen. He felt his balls tingling already.

“Thomas, I have been reading extensively about this subject, both last night and all day today. We are going to practice something called Aversion Therapy. We are going to force your wicked brain to associate pain with certain parts of your body, and certain actions. It is not important whether you understand it or not.”

She faced him, her hands on her hips. He just stared at her.

“Thomas, please remove your pants and your underpants.”

Shit, my pleasure, he thought. He slid his pants down his legs and kicked his underwear off. His penis was already about half hard. She stared at it, tapping her lips with a finger.

“I see we are none to soon,” she finally said. She picked up her whip. “Thomas. Please face your bed.” He did, and she stood behind him. “Okay,” she said. “This may sound a bit peculiar, but follow my instructions precisely, please. Please grasp your ... organ ... in your hand.”

He just stood there, not sure what she meant. Did she want him to grab his dick? She looked around him to see if he had done it.

“Thomas,” she said, giving him a smart rap on his ass with the riding crop, “do as I say. Take hold of your ... penis.”

He slowly reached his hand out and took the shaft of his cock in it. He felt a little strange doing it, but that’s what she wanted. He felt something touch his left hand. He grasped it, and looked down. Shit. She was handing him the pair of panties.

“Okay. You may sniff those panties, and manipulate yourself, as I whip you.” He almost snorted in surprise. She wanted him to jack off and sniff her panties? He jumped as the crop landed on his already-sore ass. It wasn’t that bad, he thought. He lifted the panties to his nose and took hold of the shaft of his cock. This was too much. He was jacking off under her orders. She spanked him slower than she had yesterday and not quite as hard, which was good since his ass was still sore. He was almost laughing as he jacked his cock. She thought this would make him want to stop? This was way too much fun.

“Do you ... like those ... Thomas?” she asked, inbetween smacks. He restrained the urge to nod. He knew it was a rhetorical question. “Do those ... panties smell ... good to you? Those were ... what I ... was wearing ... yesterday ... yesterday when ... I spanked ... your bottom. Do you ... like them? Do they ... smell good?”

Shit. They smelled good to him. Nice strong pussy smell, with a little honest sweat. This was too much. He didn’t even have to sneak around for this pair. She’d handed them to him. She just handed her fucking panties over and encouraged him to sniff them. Fuck. She’d ordered him to sniff them. He drew deep breaths in through his nose, drinking in her womanly scent. He felt a disturbing twitch from his dick, and knew he was only moments away from ejaculating. He wondered if she was ready for that.

He was content to smell, and jack. This was certainly the most sexual experience he’d ever had. A beautiful, albeit bitchy, woman was whipping his ass as he sniffed her panties. He couldn’t have dreamed up something this cool. Simply jacking off may never again be enough, he thought.

“Are you ... about through ... Thomas?” she finally asked, and he noticed she had slowed the pace of her crop strikes down even further. I could do this for hours, he thought. Her panties still smelled like pussy to him. His dick still felt good and hard in his hand.

“What do I do now?” he finally asked, wondering if she actually wanted him to ejaculate. He hoped she did. He had a thought about that. A thought of something he wanted to do, if she did.

“What do you usually do, when you do this?” she asked, as if she didn’t know, he thought.