Chapter 1

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/Fa, Consensual, Heterosexual, Fiction, Light Bond, First, Oral Sex, Masturbation, Petting, Teacher/Student, .

Desc: Coming of Age Sex Story: Chapter 1 - A young boy is disciplined by his guardian, a heartless but sexy bitch.

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.

“Uh ... I usually ... squirt out stuff...” he said.

“Well, then, if you must,” she said. “We must see this thing to the end.”

“Uh ... Mrs. Crane ... I usually do it ... into panties or something...” he said, trying to sound embarrassed. He didn’t actually, he’d never wanted to spoil the panties he’d stolen by shooting off into them, but hell ... why not, if she’d bring him a fresh pair each time.

“Oh, do what you must, then,” she said, sounding disgusted. She had stopped spanking him but now she gave him a gentle tap with the crop. He dropped the panties from his face and arranged them with his dick inside them. The soft material felt good on his hard cock. They were almost silk. Damn, he thought. I’m glad I thought that one up.

He just continued to stroke while she lightly whipped his behind. He saw her in his peripheral vision a time or two as she looked around his body to see what he was doing. I’m jacking off, he thought. At last he just couldn’t hold it any longer, and his knees almost buckled as he filled her panties up with sperm. He was enormously turned on, and he pumped so much out that some dripped on the floor. He sighed and she gave him one last swat.

“Well, I hope you enjoyed yourself,” she said. I sure as fuck did, he said to himself. He was happy, and felt all warm and fuzzy the way he did after he came. Now the lotion, he thought, and he lay down on his bed, waiting for her. She sighed and he felt her sit on the bed beside him.

She talked again while she rubbed his ass, she told him psychological crap she’d read from various websites and tried to explain how she thought her “treatments” would shape his personality. Shit, he thought, it’ll take years, if this is what she does every day. I’ll love the shit out of this, getting to jack off under command of the queen. Shit. He desperately hoped she’d provide him with a new pair of panties tomorrow. Those old ones were pretty soaked with cum. He could smell it in the air, and he knew she could, too.

To his surprise, she rubbed his balls again, even though she hadn’t spanked them. She coated them with lotion and rubbed it in. Damn, that feels good, he thought. She finally got up from his bed, and he sat up. His dick was still about half hard, and he was proud once again to show it off to her.

“Ugh,” she said, taking the pair of panties off the foot of his bed and holding them daintily. They were completely cum-soaked. He laughed inside his head.

“I have been curious in the past why sometimes my panties were wet,” she said, almost to herself. “I believe I know the reason now.”

She departed his room after collecting her equipment. No sooner than she was out the door he’d locked it and buried himself in his bathroom, where he furiously masturbated, less than twenty minutes after he’d ejaculated. He was really turned on, thinking of what he’d done, and remembering her scent in his nostrils.


The next day at school, he told his friend Dave all about his experiences with Mrs. Crane. Dave was entranced, he was every bit as big a perv as Thomas, and it sounded like fun to him. Thomas told him he had high hopes for that night, when he hoped to get another “treatment.”

That night dinner was enjoyable for him. Well, the anticipation of what would follow dinner helped get him through it with a smile. He went to his room, and waited for her, sitting on his bed. It took forever and he’d finally given up when she arrived.

“I am sorry, Thomas,” she said, “I had to put the dishes in the washer, the cook has the night off.”

“It’s no problem, Mrs. Crane,” he said. He started to pull his pants down, then he thought, no, don’t want to look too eager. He said and waited on her. He looked at her hands. Shit, he was disappointed. No panties tonight. Awww, fuck.

She tossed the lotion on the bed and flexed the riding crop. Suddenly she looked around.

“Oh dear,” she said. “I have already done the laundry. I’m sorry, but I have no panties for you tonight. Do you have another pair hidden away, may I ask?”

He did, but he said no, his mind racing. She looked disgusted with herself.

“Mrs. Crane...” he finally said, summoning up his courage. “Don’t you have a pair ... on?”

She stopped, and just stared at him for a moment.

“Yes, of course,” she said slowly. He could almost see the wheels turning in her head. She slowly reached beneath her skirt, as if she was almost hypnotized. He tried to catch a glimpse of her pussy, but she never allowed her skirt to rise. She inched her panties down her legs and finally stepped out of them. It turned him on big time to think that she was now naked beneath her skirt. Pantyless. His cock was already as hard as a steel rod.

“Please remove your pants and undershorts,” she commanded and he jumped to obey. He took the panties from her with eager hands and plastered them to his nose. Shit, they were still warm. He almost came, then and there. He grabbed his rock-hard cock, and pumped away at it. The fresh smell of her pussy was unreal to him. He realized he was still facing her, and she was just staring at him.

“Please turn around, Thomas,” she finally said, and he absently turned. He was really pounding his cock now, almost violently. This time, he thought, this time I’m gonna shoot it as far as I can. I’m gonna show this bitch how far I can squirt.

She finally tapped his ass with the crop, almost gently. Good, he thought. He had another thought. He was eager to somehow get her hands on his cock. he had an idea.

“Mrs. Crane,” he said, and she stopped whipping him. He turned slightly, where he could see her.

“Yes?” she said.

“Do you think...” he said, slowly, like he was having an inspiration. “Do you think it might help me if you ... if you ... spanked my weenie?”

And then rubbed lotion on it, he finished in his mind. She gave him a suspicious look, and appeared thoughtful. He wished with all his might.

“I suppose it might. I shall be careful, though, I don’t want to hurt you overly, or leave a mark.” she said. He turned all the way around, and took his hands off his cock. It stood out hard, high and proud. She looked at it speculatively.

“Hold very still,” she said, and took a step towards him. She reached out, and placed her hand beneath his cock, making a “V” of her fingers, and placing his cock on top of it. She took the crop, and carefully brought it down on his cock, still barely hitting him. He flinched on purpose, to make her think he’d felt it.

She did it five times, smacking his cock on the head with her crop, and he had a hard time to keep from laughing. Hurt, hell, he barely felt it. He wondered if she was serious. She thought this would imprint him? Shit. She’s holding my cock, he told himself. A woman has her hands on my cock. Jeezus.

“Okay,” she said. “You may finish.”

He turned, and brought her panties to his nose again. She spanked him, almost softly, as he jacked his cock and sniffed her panties. He wanted to go on forever, and he did, for a good long time. Finally he decided it was time. He felt an orgasm building in his stomach, and he locked his legs. He sped his hand up, and suddenly a squirt of semen sprayed from his cock, shooting out a good six or seven feet to fall to the floor. He moaned, and squirted again. And again. Shit, that was a good one, he thought. On impulse, he gave the panties one last snort, and then wiped the cum off his dick with them.

She’d stopped spanking him, and as he fell across the bed she sat on it beside him. As she rubbed the lotion into his ass she talked, yet again, trying to explain to him what she thought she was doing. He laughed inside as he listened to her. He was pleased, and happy.

And, yet again, she rubbed his balls with lotion. He finally rolled over, and looked pointedly at his cock. She hesitantly dribbled a little bit of lotion on it, and then grasped it firmly in her hand, rubbing it in, almost stroking him up and down, exactly as he did when he masturbated. Shit, that quick, he started to get hard again. He knew she could tell.

“Goodness,” she finally said, still stroking him. “I wish Albert had your recuperative powers. And your ... firmness...” He was of course shocked by that little speech, shocked and turned on. His cock surged but she dropped it just when it started getting good.

He had felt like she rubbed his cock a good long time and was very pleased with the whole experience. It just gets better and better, he thought. It occurred to him at this time to wonder if she really thought she was doing any good with this or if she was just fucking around with him. Why would she do that, though? he thought. Why would she play around with me, as big a bitch as she is? Why would she let me do this, something that feels this good, unless she thought she was turning me off to it? He had no idea what her true feelings were. But, as long as she was willing to do shit like this he was willing to play along. This was more fun than he’d ever had.

She collected her stuff and left the room. He was still turned on to think of her bottomless under her dress. Once again he closed the door in a hurry and flew to his bathroom, where he masturbated furiously. His dick was almost sore by the time he ejaculated again. He didn’t bother to clean up the cum on his floor. She’s so nasty-nice, he thought, I’m surprised she didn’t order me to clean that shit up. He wondered if she’d been impressed by how far he squirted. He hoped so.


The next day was pretty much a repeat performance, including her stepping out of her panties. This time she was wearing stockings and he caught a glimpse of her garter belt as she slid her panties down. His cock was insanely hard before he ever touched it. This time he stopped sniffing and once again filled her panties with his seed when he ejaculated. He got great pleasure out of watching her lift them gingerly with two fingers when she left the room. She had spanked his cock again, and rubbed lotion on it, to his great satisfaction. It’s crazy, he thought, we do something once, and she thinks it’s just part of the routine after that. His life looked great, now, before it had been boring and constrictive, but now he was happy. He had something to look forward to now.

A few more days of this, though, and she finally paused to assess her theory of Aversion Therapy.

“Thomas,” she said, as he pulled his underwear down, exposing his hard cock. She had just stepped out of her panties, and held them out to him. He took them, feeling their warmth, immediately plastering them to his face. Shit ... he felt something and looked down ... there was a wet spot on the crotch ... a goddam wet spot, he told himself. Shit. Did he ever want this pair, now.

“Thomas, look at me,” she said, and he looked up. “Thomas, do you feel like we are doing any good with this?

“I ... I think so...” he said. He sure as hell didn’t want her to stop, now.

“You are still getting ... erections, I see. I just wondered. Well, this might take a while.” she said, idly slapping her crop against her leg.

“Mmmph,” he said, as he plastered her fresh panties against his mouth and nose. He felt the wet spot on his upper lip. He almost came at the feel of it. Jeezus, he was turned on. His cock couldn’t have been any harder. Yeah, he thought, it’s working out just fine. Keep up the good work.


The next day she didn’t whip his cock, but she still rubbed lotion on it, and she rubbed it so long he got a full erection. She suddenly seemed to notice, and pulled her hand away. He flogged it unmercifully that night, after she left. He was beginning to imagine that she was enjoying the things they did.

The next day, she did something that surprised him even more. This time, when she showed up, she brought the handcuffs again. Not just two sets of them, but four. Oh shit, he thought. This was gonna be good. He just knew it was.

“Thomas,” she said, “we are going to vary our routine slightly, tonight. I am going to do all the work, while you just lay there and suffer. I hope you will find this as embarrassing as I do.”

That probably won’t happen, he thought, but give it your best shot. She indicated that he lay on the bed, and he did. Then she indicated that he get back up.

“I’m sorry,” she said, “but you’ll have to strip first.”

Strip? he thought. Totally? She nodded, and he dropped his trousers, and slowly slid his undershorts down his legs. His cock was already hard, and ready to play. He looked at her again, and she nodded. Yes. The shirt, too. He slowly took his shirt off, and was naked in front of her. Weirdly, he felt more embarrassed about his shirt being off than his pants. He slowly crawled up on his bed, and she got the handcuffs. She cuffed his feet to the rail, spreading his legs widely, and tried to reach the upper rail for his hands. The cuffs would not reach.

“Thomas, hang on,” she said. “I need to get more handcuffs.”

She left the room, leaving the door wide open. Well, shit, he thought. Sure enough, within a minute a shadow fell over the open door. He looked up, and Mr. Crane was standing there. The man surveyed the boy, stark naked, handcuffed by his feet to the bed, and laughed.

“What’s so funny?” said Thomas, irritated. He cupped his hands over his genitals, not wanting the man to see his still-hard penis.

“She’s got you now. You are a lucky boy,” Mr. Crane said, and disappeared, still laughing. Shit, thought Thomas, yes, I know I’m lucky. Leave it alone, old man.

Within another minute Mrs. Crane showed back up, with two more handcuffs. Shit, thought Thomas, how many pairs of those damn things does she have? She made a chain, connecting the new cuffs to the ones already on his hands, and was able at last to cuff them to the rail. He was immobilized, his hands and feet securely bound.

“Now, Thomas,” she said. “I don’t want you to think I’m doing this because I enjoy it. You are a bad boy, and this is your punishment. I am willing to undergo this trial in a brave attempt to turn you from your wicked ways. Someday I hope you will thank me.”

Yes, I’ll thank you already for playing with my dick last night, Thomas thought. He was enjoying laying naked, his hard cock standing straight up in the air. He noticed how her eyes returned to it, time after time. He imagined she had a special interest in it.

She was wearing a much shorter skirt than normal today, for some reason. He looked at her again, realizing just how short it was. Surprising. She looked good in it, though, her muscular legs were shown off well.

“Well,” she said, “let us begin.”

She reached beneath her skirt, and dropped her panties down her legs. She came to the side of the bed, and arranged them on his face where the crotch was on his nose, but he could look out the leg holes. His dick just got harder and harder. Everything she did seemed insanely sexy to him, and she seemed to have no clue.

He had carefully watched her remove her panties in the short skirt, and he imagined he’d been able to catch a fleeting glimpse of her pussy. Her skirt had ballooned outwards when she raised her leg, and, from his low elevation on the bed, he was able to look up it. He felt like he was just moments from ejaculating, he was so turned on.

She disappeared into his bathroom for a moment, returned and moved to the end of the bed, and picked up her riding crop. She crawled over the railing his feet were handcuffed to, and, on her knees, crouched between his spread legs. He felt something cold on his cock, and looked down to see her dribbling baby oil on his cock. Oh shit, he knew that bottle well, it was from his own bathroom. He felt breathless with anticipation.

Her hand clasped his hard slippery cock, and he gave a guttural moan. She smiled down at him, an evil smile.

“Thomas, this is not about you having a good time. This will, I hope, train you to associate pain with ... masturbation.”

He felt her touch him. She pulled her fingers out to the end of his cock and then circled it, squeezing tightly, finally pushing her hand back down to the root. He gave a deep gasp. He could have cum, that instant but somehow he held back. His eyes were closed and he jumped when she struck him with the crop on his chest. She continued to jack him and strike him each time her hand traveled the length of his cock. He was in heaven. And shit, she wasn’t hitting that hard. He felt a little pain, but not much...

The whole thing had an air of unreality about it that almost left him light-headed. He felt like he was dreaming or something. A woman is jacking me off, he told himself time and time again. A woman.

Suddenly, he could take it no longer. He felt a giant surge from his penis and a huge dollop of sperm shot from the end of his cock. He plainly heard her say “goodness,” and she stopped for a moment, to his displeasure. Luckily she started up again and he let the moment carry him away.

When he finally regained his composure she smacked him one last time right on the tip of his softening cock. Luckily, she hit lightly. He sighed in pleasure, having had one of the greatest experiences of his life.

“Thomas...” he heard her say. He opened his eyes. Jeezus. She looked shocked and was holding her arms out from her sides. He saw shiny spots on her clothes and looked closer. She was covered in his cum! He almost wanted to shriek with laughter but he kept his mouth shut. He could even see it in her hair. She carefully climbed off the bed and disappeared into his bathroom.

Well, he wasn’t going anywhere. He lay on the bed, basking in the warmth of his orgasm. Damn, though ... he was still turned on ... and seeing her splattered with his cum was too much. He heard the sink run and finally she returned.

“Thomas,” she said, ever practical, “when we are done here, you need to spend some time cleaning the chrome in your restroom. It looks terrible.”

She unlocked him at last and he sat on his bed, rubbing his wrists.

“Goodness,” she said, “we forgot the lotion.”

Oh jeezus, he didn’t know how much more of this he could take. He just flopped over backwards and lay there, determined to just let her do whatever she wanted. She found her tube of lotion, sat on the side of the bed, one leg laying crossways on the bed, and one on the floor. She dribbled some lotion on his chest, and began to rub. He sighed, hoping she’d go down a little further.

He turned his head, and looked sideways at her skirt. My god, he thought, as rational thought fled his mind. He could literally see beneath her short skirt, it was partly folded back on itself, and he could see ... her beautiful cunt. Jeezus. He felt an immediate surge of blood into his cock. He just lay there and stared. Her cunt was fabulous. It was pretty hairy but that just turned him on all the more. She had fat, puffy pussy lips, pink, and the inner parts of her pussy were deep red. He could see what he imagined to be her clit above the hole of her vagina. Her vagina was stretched slightly since her leg up on the bed was spread widely. He was stunned and amazed. My first cunt, he thought. My first beautiful cunt.

She seemed absolutely unaware what he was doing. She was talking about more psychological crap but he wasn’t listening. He was in love. Seeing her cunt was a thousand times better than some stupid magazine. About that time she dribbled some hand lotion on his cock and seized it in her hand. His cock was over half hard, struggling valiantly to recover from his massive ejaculation of a few minutes ago, and the feeling of her soft strong hand was all it needed.

“Goodness, Thomas,” she said, “I believe this is having the opposite effect on you. I wonder if I’m doing the right thing.”

He cleared his throat, not taking his eyes off her fantastic cunt. “I think we are, Mrs. Crane ... it’s just something I have to get out of my system...”

“Well, I’m not totally convinced ... I guess we should give you a while longer...” she finally said, while giving him a hand job that would make a Japanese masseuse green with envy. He almost thought he was going to cum again, but she stopped before he got that far. His cock was still rock-hard, and stood almost straight up.

She finally slid her leg off the bed and the peep show was over. She stood and unlocked him from the bed, gathering up her supplies.

“You may dress, Thomas,” she said, and left the room. He slammed and locked the door and disappeared into his bathroom. He had unfinished business.

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