Tommy had a crush on Denise since Junior High, but was too shy to do anything about it. Since they were both in band and taking college prep courses, they were in nearly every class together. Denise was nearly as shy as Tommy, which was part of his fascination with her. Senior Prom was approaching fast and he realized that this could be his last chance.

Fortunately the very things that Tommy found attractive about Denise didn’t make her popular. Shy, nerdy girls rarely are popular. Few people, particularly in high school, find freckles and glasses attractive. Tommy adored her long legs, but plenty of guys don’t like her six foot tall frame. But the final straw is her tits, or lack thereof. Denise’s tall, lean frame has only small bumps on her chest. So many boys are fixated on thick girls with big, bouncy breasts, that girls like Denise are largely ignored.

No matter what anyone else thought, Tommy believed that Denise was the most beautiful girl in the world. He imagined himself spending the rest of his life with her. Before that could happen, he needed to ask her out just once. He convinced himself that today was the day. He would ask her before band.

“Denise. Umm. I was wondering. More like hoping. What I mean is. Would you go to prom with me?”

“I’d like that. But my parents are really strict. I’ll ask them tonight and let you know tomorrow.”

“Could you call me or email their answer?”

“I said they are strict. I’d get in big trouble for contacting a boy.”

It was the longest night of Tommy’s life. He waited at Denise’s locker before school, anxious for the answer.

“Well?”

“My Mom said that you need to come to our house and ask her for permission.”

“I have to ask your Mom rather than your Dad?”

“Yeah, my Mom is basically queen of the house.”

“Can I come over tonight and ask her?”

“You can come over right after school. She doesn’t work.”

The school day couldn’t end soon enough for Tommy. When it finally did end, Tommy was terrified of facing Denise’s Mom. He’d seen her at band concerts. Most boys, Tommy included, would say she was a MILF. Mrs. Vance shares her daughter’s height and freckles; although the freckles aren’t as pronounced. However, she has blonde hair instead of red and has a really nice pair of tits that she often shows off with tight tops. It is easy to tell that they are Mother and Daughter, but most people would conclude Mom is significantly hotter despite her additional years. This was the root of Tommy’s issue, Mrs. Vance’s looks intimidated him. He was afraid he wouldn’t be able to talk to her.

But having a chance to date Denise was too big of an opportunity to skip. Tommy summoned all of his courage and rang the doorbell.

“Good afternoon Mrs. Vance.”

“Come in Tommy. Denise tells me that you have something you want to ask me.”

Tommy was afraid he would chicken-out if he didn’t get it over with quickly.

“Mrs. Vance, I would like your permission to take your daughter to prom.”

“If you want to go on a date with my daughter, I have a few conditions.”

Expecting that she was going to mention curfews, avoiding alcohol, and similar things Tommy replied, “I’d do anything.”

“I hope you mean that. My daughter deserves to be treated like a princess.”

“I completely agree.”

“Interrupting a woman while she is talking to you isn’t how you should treat her. This is exactly what I’m talking about. You need to learn to how to treat a woman properly. Is that something you are willing to learn?”

“Yes”

“Yes, what?”

“Yes ma’am.”

“That’s better. Would you like me to teach you what it means to treat a woman like a princess?”

“Yes ma’am”

“Then you need to ask me.”

“Mrs. Vance, would you please teach me how to treat a woman like a princess.”

“I will, but only if you work hard to learn. If I think you aren’t trying hard enough, the lessons are over. If you show me that you can treat a woman like a princess, then I will allow you to date my daughter. Do you think having sex with my daughter would be treating her like a princess?”

“No ma’am”

“Do you ever masturbate?”

Tommy hesitated before admitting that he did.

“Do you ever think about Denise when you are masturbating?”

“Sometimes ma’am”

“Does that seem like the right way to treat a princess?”

“No ma’am”

“Would you agree not to masturbate in order to date Denise?”

This conversation wasn’t going the way Tommy expected, but Denise was the girl of his dreams and he could put up with just about anything for the chance to date her.

“Absolutely ma’am”

“Can you give me even one good reason that I should trust you?”

“I can’t think of one ma’am”

“Fortunately for you, I know a way to guarantee you won’t masturbate or try to convince my daughter to have sex with you. You said that you would do anything in order to date Denise, did you really mean that? Would you give up the ability to masturbate in order to date her?

“I meant what I said. I would do anything.”

“Good. Let me explain what is about to happen. I’m going to lock your penis in a device that will stop you from being able to touch yourself. In fact, the device will be so tight that you won’t even be able to have an erection without some pain. In order to work properly, the device needs to be fitted perfectly. I need to measure your penis when you aren’t even slightly aroused. That is only possible right after you ejaculate. Get undressed.”

Getting undressed in front of anyone was awkward for Tommy. This would be even more awkward. Mrs. Vance turned him on. What would she think when his pants came off and she saw his erection?

“Have you ever seen a naked woman?”

“Not it real life.”

“I don’t want you thinking about Denise while you masturbate. I’m going to take off my top and I want you to keep your eyes open and looking at me until you orgasm.”

Tommy felt awkward playing with himself in front of a woman. Mrs. Vance’s tits were even nicer than he had imagined. Was it strange to get so turned on by his girlfriend’s mom? It didn’t take long before he came. Mrs. Vance was prepared with tissues to catch it all. She waited until he was flaccid and then measured the length and circumference of his penis.

“Looks like you will need an extra small cage. I will place a rush order on a custom-fitted steel model. Until then I will be locking you into a plastic one. Wait here, just like you are, while I get one from the basement.”

It felt nice having Mrs. Vance touch his penis as she guided it into the plastic cage. Tommy was certain he could tolerate this for the month between now and prom. Denise was worth a little pain and embarrassment.

“Now that you are properly caged, there are some other lessons that you will need to learn before you can spend any time alone with Denise.”

“I’m ready ma’am”

“The first two that you need to learn are house cleaning and giving a good foot massage. Go home and learn everything you can online about giving a foot massage tonight. After school tomorrow, you will come straight here. I will have a list of chores for you to do and you will show me how well you have learned to massage feet.”

“Yes ma’am.”

Tommy spent the evening learning everything he could about foot massage on the internet, trying out different things on his own feet. He was determined to impress Mrs. Vance the next day.

Even though Tommy was going directly to Denise’s house after school, he wasn’t allowed to drive her home or even see her at the house. His only job was to show Mrs. Vance that he could learn to treat a woman like a princess. Today’s job was to clean all of the bathrooms and the windows throughout the house. Tommy took his time to make sure everything was perfect. It was 8 pm when he was done. Tommy was tired and hungry, but waited patiently while Mrs. Vance carefully inspected his work. Her inspection lasted over 30 minutes. She found a couple imperfections, but told him that he had done a good job overall. Tommy was looking forward to going home and eating.

“One more thing before you go Tommy. Did you forget about my foot massage?”

Tommy lied.

“Kneel on the floor and show me what you learned.”

Mrs. Vance sat on a kitchen chair while Tommy knelt on the hard tile floor. Tommy gently removed her heels and began rubbing her stocking-covered foot. He moved slowly, trying to recall everything he had learned. After 20 minutes massaging her right foot, he switched to the left and gave it equal attention. He finished, thinking he had done a good job.

“Is that the best you could do?”

“It wasn’t good enough, ma’am?”

“Not by a long shot.”

“Please tell me how to do better.”

“First, you need to pay more attention to my response. Make sure that you are using the right amount of pressure. Start softer and gradually increase the pressure, making sure you never rub too hard. Don’t give every area the same amount of attention. Notice which areas I enjoy having rubbed the most and spend more time in those areas. Finally, you need to ask me what I want. Do you know that I wanted my feet rubbed over my stockings?”

“No ma’am. I just assumed.”

“Never assume, make sure you are doing exactly what your princess wants. You should have also asked if I was ready for you to move to my other foot. As it turns out, I wasn’t ready yet. I trust you will do better tomorrow.”

Tommy drove home feeling like a failure. He had tried so hard to impress Mrs. Vance but hadn’t pleased her. But tomorrow was another day, he would do better. He had to.

“Good to see you Tommy. I have some different chores for you today. The floors need cleaned. You will scrub the tile with a brush and sponge. I set out rags and polish for the wood floors. Any questions?”

“No ma’am.”

The Vance’s have a large house. Today’s chore took even longer than yesterday. Tommy was on his hands and knees cleaning until almost 9 pm. His stomach hurt from hunger. His knees felt like someone had driven nails into them.

“I’ve finished with the floors Mrs. Vance.”

“Let’s check your work before you give me a foot rub.”

Tommy was thankful for the chance to stand. He was even more pleased when Mrs. Vance praised his work. Even though it hurt to kneel on the floor to give her a foot massage, Tommy recalled all of his lessons from yesterday.

“Would you prefer your stockings on or off for the foot rub ma’am?”

“Please take them off for me.”

Mrs. Vance wore stockings rather than pantyhose. Tommy carefully reached up her skirt to slide down the stockings. He noticed her firm, thin thighs. He’d never thought about what great legs she had. He could feel his dick swelling against the plastic cage.

Tommy took his time with her feet, carefully judging her reaction to each movement. He spent nearly 30 minutes with her left foot.

“Are you ready for me to switch feet?”

“Yes.”

Tommy gave just as much attention to her right foot.

“You are a quick learner Tommy. That was much better than yesterday. When you go home tonight, I want you to study how to give a full pedicure. I’ll want you to start practicing tomorrow. I expect you here by 9 am. There will be plenty of chores as well.”

Tommy was glad it was Friday night. At least he could put off his school work and focus on what Mrs. Vance wanted him to learn. He arrived 10 minutes early on Saturday morning.

“Saturdays are laundry days at our house. I’ll have you start with that. Be sure to treat any stains and pay attention to the washing instructions. Undergarments should be hand washed. Iron anything that needs it before hanging it up. Carefully fold everything else. Any questions?”

“No ma’am, I’ll get started right away.”

In addition to Denise and Mrs. Vance, there were also clothes from Mr. Vance and Denise’s little sister Sandra. The week’s worth of clothing made quite a stack. Apparently, everyone in the family exercised regularly too, as there were dirty gym clothes including extra bras and panties. Tommy started by sorting the clothes and checking for stains. Once the first load was in the wash, Tommy started hand washing the lingerie. He couldn’t resist checking out the bras a little more closely. It was obvious which ones were Mrs. Vance’s rather than her daughters. She wore a D-cup and her daughter’s bras were much smaller. One girl wore a 34 B while the other wore a heavily padded 32 AA. He couldn’t be certain, but he immediately suspected that his precious Denise wore the smaller, padded bra. Even though she was 2 years older than her sister, she looked thinner. He wouldn’t have guessed that she was that small, but it didn’t change his desire for her.

Tommy took his time washing the bras, imagining what each set of breasts, even Sandra’s, would feel like in his hand. He switched over to the panties. The panties had varying degrees of stains in the area covering the pussy. Tommy couldn’t resist sniffing each pair, comparing the slight differences in aroma between each one. Tommy carefully scrubbed out each of the stains.

Tommy was surprised to find that Mr. Vance also had a lengthy set of chores for the day, including cooking all of the meals. He had been away on business during the week, so Tommy didn’t know what happened on evenings that he was home. He suspected that Mr. Vance knew how to treat a woman like a princess, just like Tommy was learning now. Although Tommy couldn’t explain exactly why he suspected this.

The laundry took most of the day. Tommy wasn’t fast at folding or ironing and he was determined to make everything perfect. He revelled in the praise from Mrs. Vance at what a nice job he had done.

“Let’s see what you have learned about giving a pedicure.”

Tommy started well, picking a perfect temperature to soak her feet. She had regular pedicures, so there wasn’t much work to do with the pumice stone. Tommy focused on giving another great foot massage and followed that up by painting her toenails.

“That was good up to the nail painting. You did a sloppy job. Look at those brush marks and the gaps at the edges. Maybe my husband needs to show you how to do this right.”

Mr. Vance demonstrated on Sandra. Tommy still wasn’t allowed to spend any time around Denise at the house. He paid close attention to everything Mr. Vance did. Now he was certain that Mr. Vance received some of the same training he was undergoing. Tommy wondered if Mr. Vance had to wear a cage on his cock, or even if he still did.

“Now that you’ve seen one done correctly, strip off the nail polish and start over, including the foot massage.”

Tommy’s knees were still sore from the day before and this lengthy time kneeling in front of Mrs. Vance hurt. But he pushed that pain to the back of his mind and focused on doing an even better job this time.

“That was adequate, but barely. Clearly you need more practice. Take tomorrow off and I’ll see you right after school on Monday.

Tommy arrived promptly after school on Monday and knocked on the door, eager to prove himself worthy of a date with Denise.

“I have good news for you Tommy. Your custom cage arrived today. Let’s get you fitted before you start your chores.”

Tommy undressed for Mrs. Vance which caused his dick to swell against the plastic cage. He watched as she unpacked the new cage from the box. It looked much smaller than the plastic one. He wasn’t sure how he could fit in such a tiny device. It was such a relief when Mrs. Vance unlocked his cage and removed it.

“Regular hygiene is important when wearing a cage. I’m going to clean you off before placing you in the new cage. Don’t even think about having an orgasm while I clean you.”

Mrs. Vance scrubbed his hard dick vigorously, gripping hard around his member with a fist full of soap. She was obviously testing him, trying to coax him to cum. It took tremendous concentration to distract himself from the amazing feel of a woman playing with his cock.

His swollen dick would never fit in that tiny cage. Mrs. Vance solved that problem with a bowl of ice. Shrunken to a small nub, Tommy’s dick was a perfect fit in the cage.Instead of putting his own clothes back on, Mrs. Vance had a tight pair of bike shorts for Tommy to wear. His chores for the day were in the yard. The shorts were tight enough that Tommy was sure that anyone looking at him would be able to see the cage. Tommy worked in the yard until dark.

“Time to practice your pedicure skills. This evening you will give both Sandra and I pedicures.”

Tommy did a better job this evening than he had on Saturday, working hard to serve Sandra just as thoroughly as he did her Mother. When Tommy was removing her stockings, he noticed that Mrs. Vance wasn’t wearing any panties. Throughout the foot massage, Tommy kept glancing up her skirt hoping to catch another glimpse of her pussy.

“You did a nice job on the pedicures, with a little more practice you could become good at that. However, do you think it is treating me like a princess to try looking up my skirt?”

“No ma’am. I’m sorry.”

“You will be sorry. I’m going to spank your little ass until you can’t sit down. Get you pants down and bend over.”

Tommy moved quickly to do as he was told.

“I think you also need to apologize to Denise.”

“Sandra, bring my belt and get your sister while you are upstairs.”

Tommy was naked from the waist down with his tiny cage dangling as he bent over waiting. He realized just how humiliating it would be to beg for his crush’s forgiveness in this position. Denise and Sandra walked back into the room.

“Tommy, do you have something to say to Denise?”

“Denise, please forgive me. I was completely out of line. I was trying to look up your Mom’s skirt. I should never have done that to her, or to you. I know I deserve the spanking that your Mom is about to give me. I’m sorry and I really want to prove that I’m a guy who can treat you like deserve. I know I still have a great to learn, but I want the chance to learn it.”

“I’m going to give him 20 swats with the belt for looking up my skirt. I’ll let you decide how many he deserves for looking lustfully at another woman.”

“I think he needs 20 swats for looking at someone other than me and an extra 20 because it was my Mom. But split them up between tonight and tomorrow.”

“You should stay and watch Denise. It will be a good reminder to Tommy of why he is here. Do you want your sister to stay too?”

“Yes. Both today and tomorrow. I’m sure it will be worse for Tommy being spanked in front of us both.”

“Excellent thinking. You give me hope that you will know how to take charge of your relationships when the time comes.”

Tommy was surprised by Denise’s assertive and sadistic streaks. A week ago, he wouldn’t have wanted to date a girl with either of those characteristics. Now he was at least as aroused as he was intimidated.

SMACK! The first stroke landed. Tommy couldn’t believe that it hurt so much. His parents had spanked him up to first year of high school. He was relieved when they declared him too old for spankings. Maybe it had just been too long, but he didn’t remember his Dad spanking this hard.

SMACK! Tears were already starting to form in his eyes and he still had 28 swats to go. Denise would think he was a wimp. Although seeing him locked in that tiny steel cage had probably already convinced her that he was a wimp. Would she ever understand that he was only doing this for her?

Tommy was crying hard by the end of the spanking. It hurt to put on his jeans and drive home.

The chores continued each day along with daily pedicure practice. On Friday, Mrs. Vance declared that Tommy had proven his ability to perform pedicures enough that he would also be allowed to give one to Denise. As careful of attention as he paid to her Mom, Tommy put in even more effort to make Denise’s pedicure perfect. After failing her on Monday, he was determined that he could show her how much he cared for her.

“I think you have learned this first lesson well. You have the weekend off. My husband will be doing the laundry, along with the rest of his chores, this weekend. Next week, you will start learning to give good back massages. Study up on massage techniques this weekend.”