Today, I try to do everything right. I figured that trying to get spanking was perverted, so I'm not going to go that way. Mom comes home and starts dinner and says, "Tonight, Donna and Amy will be having dinner with us. I want you to dress nice. Think of it as a date." A date? Now I am embarrassed because it is a formal date. I don't know what to do or say. However, Amy understands me, so it should work out.
The doorbell rings and I go answer it. There they are. Mrs. Donna is wearing a sexy red dress showing some serious cleavage. Amy is also wear a nice dress that is red and black but not showing much cleavage. Her dress is backless, and she is not wearing a bra. Nice.
The dinner goes well, and we retreat to the living room to watch a boring romantic comedy. I am not the only one bored. Amy's mom and my Mom are chatting the whole time. That's all they do. Even Amy looks bored as we engage is a little conversation ourselves.
"Billy, did you do all your chores today? Dishes, vacuuming, cleaned the bathroom?" my Mom asks.
"Of course, I did," I reply. Is she trying to start something? I wonder what is behind all this. She knows I did the dishes. She just cooked a big meal and should have noticed the clean dishes. However, with the dinner we just had, I have a lot to do when they leave.
"Amy, what about you? Finished your chores today?" Mrs. Donna asks Amy. They must be working together.
"Yeah, I'm done," Amy replies.
Mrs. Donna also asks, "Taken out the garbage, pick-up is today?"
"It was today?" Amy says. "Um, I forgot about that. I always forget about the once-a-week chores. You know?" Amy tries to get out of it.
"I can't have all that garbage pile up all week." Mrs. Donna says. "The stray dogs will get into it and trash up the yard."
My Mom asks "What about you Billy? Did you get the garbage?"
"Yeah, I remembered about it," I say. I luckily remembered about that. Couldn't Amy just lie about? Her mom would find out later and get her spanking later. It is not like her mom would have gotten up to check so she could have her punishment here. Then again, it sounds like our moms are trying to get up both spanked at the same time. I think our moms are perverted.
Mrs. Donna is ready. "Amy, time for your punishment."
Amy says, "Does it have to be here? Wait we wait until you get home?"
"No Amy," Mrs. Donna replies sounding upset. "Why are you always trying to get out of your punishment? When have I ever backed off? Are you ready or should we add more spanking?"
"I'm ready," Amy say giving in. Amy stands and starts pulling up her dress. She reveals a sexy red lace thong making her round ass look perfect. She slips her whole dress off and shows off her amazing breasts. She pauses a few seconds and starts slowly sliding her thong down. She stands up displaying her clean pussy looking like it is ready for my tongue. I wish I could just get up right there and give her a tongue bath.
Mrs. Donna says, "Joanne, could you get me a hair brush. Wait. How about your paddle? That should do." My Mom grabs the paddle and hands it to Amy's mom. Amy is about the get spanked by the paddle that spanks my nude ass. I can't wait for my next spankings after that paddle gets Amy's ass. Amy moves to her mom looking like she is trying to hold back a smile. Did she want this? Did she plan this? I guess I screwed up because I didn't get punished to be spanked with her.
Amy gets on her mom's knee. Unfortunately, I don't have much of a view. All I can see from my angle is her pussy and ass. I can't see her boobs. Anyway, the spankings start, and I watch her ass get red and pussy get wet. I'm just trying to get as much in for my jack-off session tonight. The spanking eventually end. Amy get up, grabs her dress and thong then heads for the bathroom.
"Where are you going?" her mom asks.
"I need to pee," she replies. She continues to the bathroom and takes her time. I wondered if she having feminine issues or rubbing one off. She returns and sits next to me. "I have a present for you," she whispers in my ear. She makes sure our moms are not looking and slides her hand to my pocket and puts something in it.
"What?" I ask.
"My thong. You can keep it," she devilishly replies. I am going to have a good night.
The movie ends and Mrs. Donna and Amy begin to leave. I get hugs and another kiss on the lips this time. No tongue. Well, our moms were right there so a make out session isn’t appropriate. I clean up the kitchen and go to bed. I went to sleep late because, no surprise, I spent hours jacking off and smelling her thong.
I wake up on time. Tell my Mom goodbye as she heads for work. I do my chores, and have some free time to masturbate. My mom gets home, and she is very happy for some reason. "We are going to Donna's and spend some time at the pool and work on our tans." Cool. I haven't been swimming in a while, and I get to see Amy again in her skimpy bikini. Up close this time.
I go upstairs and change into my swim trunks. I go back downstairs and find my mom wearing a really long shirt holding a bag likely full of towels. She always does as her swimsuit is underneath and takes off her shirt when she gets there. We go to their pool through the back yard not having to go through their house.
Amy comes out and shows off her green bikini accenting her breasts and her pussy outline. Mrs. Donna comes out absolutely stunning. Whoa, she's topless! Her D-cup breasts droop a little, and she has huge areolas. She is also wearing a thong, but the cloth is barely covering her pussy and nothing more. Any shift and it would show all.
Amy is shocked and tells her mom, "Mom why are you topless especially in front of company?"
Her mom, says, "Amy, we are trying to work on our tan today. You are going to have to take off your top too."
"But Mom, why?" Amy tells her mom seeming upset.
Her mom replies, "Don't worry, we all seen them."
My Mom starts taking off her shirt. Oh no. She's topless too, and she's wearing the exact same thong Amy's mom is wearing. They must have gone shopping together. She has an amazing set of C-cup breasts that somehow defy gravity. So here we are. Both our moms are topless wearing a thong barely covering the exits where Amy and I came from. Amy is also wearing a thong but also a top. And me, I am in a large baggy swim trunk. I feel out of place, but I didn't feel like showing off my goods.
Amy says, "How come the girls have to wear all this sexy stuff showing our...you know. What about Billy?" Damn. I don't have any other swimwear, and I don't want to swim nude.
My Mom smiles "Don't worry. I planned for this." She reaches in her bag and pulls out a yellow thong. I almost pass out. "Don't freak out Billy. It's a man's thong. It has a pouch to make room for your penis and scrotum. It should fit, and you'll get a nice tan too. Go in the bathroom and change."
I reluctantly grab the thong and head inside. I enter the bathroom and lock the door. I take off my trunks and see my giant erection. I hate being a teenager. I wonder if my stiffie will show. I put on the thong and with it all the way up, the elastic band don’t go high enough to cover head of my dick. The only thing I can do is quickly masturbate to get rid of this erection. I grab some toilet paper for clean up and get to work. Unfortunately, I am in a foreign bathroom and somehow lose my balance. I grab the towel rack to catch myself. And then it happens. I somehow rip a part of the rack off the wall. I realize it would take serious repairs to get fix. There is no way I was getting out of it. I knew I have to tell Mrs. Donne immediately. I'm getting a spanking today, in front of Mrs. Donna and my Amy. After trying so hard not to screw up today, I did. I notice my penis is soft and quickly put on the thong. Time to confess.
I open to door to go outside and hear all the girls whistling at me as I'm giving them a nice show of my bulge. I head strait to Mrs. Donna and softly tell her about the towel rack and how I would even pay for the repairs. I tried to talk soft enough so my Mom couldn't hear me.
"Billy, Billy, Billy." Mrs. Donna says loud enough for all to hear. "Yes, you will pay for the repairs. I'm glad you confessed."
"What did Billy do?" My Mom asks as I take a huge gulp.
"He ripped of the towel rack in the bathroom," Mrs. Donna tells my Mom.
I tried to explain myself without the masturbation part. "I was putting on this thing and I lost my balance. I'm really sorry."
"Billy, what is wrong with you. You will definitely pay for the repairs. And still get a spanking. We'll go inside for your punishment," my Mom says. We go inside into the living room. I turn around and notice that Mrs. Donna and Amy followed us. Great.
"Do I need to take my thong off? I don't have to," I plea.
My Mom tells me "Yes, take it off. Didn't Amy try that already? Her mom didn't let her off the hook. Why should you?" I slip off my thong and became erect in no time with Amy in her bikini, and both our moms topless. My Moms asks Mrs. Donna, "Can you get me a towel and I guess a hair brush since that what you use?"
"Well, all the towels I have are too nice to get any cum on it," Mrs. Donna says. "I got an idea." She leaves for a minute and comes back with the hair brush. "This should prevent the mess." She has a small packet in her hand and opens it. It is a condom. Am I about to have sex? She takes the condom and slowly rolls it onto my penis. This is the first time anyone has ever touched my penis. It is electrifying. The way she is putting it on is almost like she is jacking me off. I couldn't be any harder.
"I'm ready," my Mom says. I move to her and cannot stop staring at her breasts. I get on her knee, and I can feel the skin of her legs through the condom. It feels much better than that rough towel. She starts spanking me. The spanking is not hard as usual but my dick cannot take it. In no time, I am cumming into the condom. I cannot describe how good it feels. She keeps spanking and spanking even though it is not hard enough to sting. She finally stops. I get up and find my shrunken cock with the condom which slipped half-way off hanging down full of semen.
Mrs. Donna says, "Amy go get a wet wash cloth to clean him with." Amy leaves and returns with a wet cloth. Mrs. Donna removes the condom and leaves to go throw it. Amy takes the wet wash cloth and gently starts wiping my dick. She treats my dick so smoothly. I strongly want her to open her mouth and engulf my member. However, even with all that I cannot get erect again.
My Mom tells me, "Okay honey, put your swimwear back on." I quickly get my thong back on while my dick is limp so it could stay down in its pouch. We all go outside and out moms jump in the pool. Amy, however, takes her time untying her top and takes it off. She turns to me, embraces me, and kisses me. Not a short kiss like last time. Her tongue enters my mouth, and we start making out. We eventually let go. I notice our moms looking like they were not paying attention to us, but they had huge smiles.
I just enjoy the show that the females are putting on for me, especially the three pairs of tits. I'm going to masturbate all night again.
My alarm wakes me up, and I head to the kitchen. Mom is not working today, but I still want to be up early so she doesn't have an excuse for any punishment.
As we eat breakfast, Mom tells me, "Honey, I need to discuss something. I didn't want to say anything before because I know you are just growing-up and becoming a man. However, it is becoming a problem now. I can hear you every night, and it is keeping me awake. Your masturbation habits are too frequent and have become excessive. I know it is okay every now and then to get a release. But, I'm worried you are abusing yourself and may hurt yourself one day. I have been telling you to control your urges but apparently you have been unsuccessful."
Mom continued, "Donna gave me an idea to help with your...leakage and...erections during your spankings. It would also help with your problem. It should come in soon. So, don't worry sweetie. I'll help you with your problems." I have no clue on what Mrs. Donna's idea was. I cannot image my spankings getting worse. Also, I don't want any help to stop masturbating. I enjoy it. I will only stop when I have something better than my hand. Like Amy's mouth or pussy. But, until I get that, how could I stop that wonderful feeling.
"Donna and Amy will be spending the day with us especially for lunch and dinner," Mom says.
"They always come here to eat. Do they not know how to cook?" I ask.
"Not really. But, it is hard buying groceries for cooking for two. And, I get tired of eating leftovers."
"I totally agree. Do I have to wear anything nice like last time they came for dinner?"
"No sweetie," Mom says. "I want to relax today. I don't want to spend time getting dressed up. It's my day off. However, you need to get your chores done before they get here."
"Not a problem," I tell her. I change into some comfortable shorts and a t-shirt, and I get all my chores done. I am debating whether I should not do something so I can get a spanking today. I have no idea if that what Amy wants to do. I would like to try a double-spanking with both of us nude. However, it is more embarrassment than sexual gratification.
After my chores are done, the doorbell rings and I answer it. Mrs. Donna is wearing a light blue button-up blouse and jeans. It is clear that she is not wearing a bra as her nipples are poking out. Amy, however, is wearing a pink camisole and some Sponge Bob pajama bottoms which the waist is tied with a string. I want to untie that thing and get it off right now. She is wearing a bra as I could easily see her white bra straps on the side of her camisole straps. I don't know if it is the casual clothes or the bra straps showing, but it is turning me on. We greet and Amy gives me a huge hug and we deeply kiss.
In the middle of our kiss, Amy's mom stops us, "Knock it off love birds." We slowly back away from each other, and I can see the lust in Amy's eyes.
Both our moms go in the kitchen and start preparing a light lunch. Amy and I stay in the living room.
I ask Amy, "Why are you wearing a bra, unlike your mom?"
"I don't know. I don't want to show off my nipples outside. And, this bra lifts my boobs up and creates some good cleavage. Don't you agree?"
I give a good stare at her breasts. "Absolutely. They are stunning."
Amy asks, "Are you...um...going to get punished today? Because I am."
"Why? What did you do?"
"I didn't do the laundry. My mom noticed before we left. I think she will punish me later. What about you?"
"Uh, I did everything today," I reply.
"But Billy, I was hoping we could get punished together. Naked together. Wouldn't that be hot?"
"Sorry Amy. I didn't know that's what you wanted."
"That's okay," Amy says. "Don't worry. I give you a good show." I can't read a girl's mind. But, it does not bother Amy.
Amy and I discuss movies, movie stars, and about school in a couple of months. She is joining my school this year, and I give her all the details. All of us eat lunch. Amy and I sit next to each other afterwards. I have my left arm over her shoulder caressing her left arm. She has her right hand on my left thigh halfway between my knee and my crotch. It does not seem to bother our mothers. I guess they are happy we are hitting it off. Then, it starts after dinner.
Our mothers’ conversation dies down, and Mrs. Donna brings it up. "Amy hasn't taken care of the laundry in a while, so she needs a punishment. What about Billy?"
Mom replies, "yeah, him too. He's been masturbating too much and it has been keeping me up at night."
Whoa. Doesn't this fall under too much information for our guests? I couldn't believe it. Not only am I getting punished, but she has to tell them that. Amy, however, is doing a victory dance in her head. I guess she got her wish.
Mom chimes in, "Billy, you're first. Strip." Mrs. Donna stays quite.
"Wait, one at a time?" Amy asks.
Her mom yells at her, "Of course. I’m not going to have both of you naked at the same time. Why? Is that what you wanted? Don't tell me you didn't do the laundry because that is what you wanted. You are going to get the spanking of a lifetime, after Billy is dressed." Amy becomes upset and starts crying. I wish I could help her. However, I stand up and remove my shirt. I then slide down my pants and underwear. I am still ashamed about my tighty-whities. I reveal a semi-erection, but it's on the way up.
Mom says, "Wait for a second. Donna, I like your condom idea. Wait here." Great, she is going get a condom. She leaves, and now I'm standing naked next to Amy and her mom.
"Billy," Mrs. Donna says. "Your mom is right. You are going to make some girl really happy one day. Maybe it will be Amy." I can't believe she said that. I can't believe my Mom told her that. Both Amy and I blush. Although, I would love to make Amy that happy girl soon.
Mom returns, "Here you go." She starts rolling the condom on my stiff member. The condom is blue and ribbed. She turns to Mrs. Donna, "it's ribbed and ultra-sensitive. It's my favorite. Too bad I am wasting one on him." The last thing I need is for Mom to talk about her sex life. Then again, I did not know she even had one.
Well, I get on her lap, and my penis gets situated between her legs. She starts with that wooden paddle slamming my ass. It does not take long for me to get off. That thin condom feels really good. Eventually my Mom is done, and I get up.
Mom says, "Amy, can you get a wash cloth from that closet over there, and wet it to clean him up like last time." Amy gets up, retrieves the wash cloth, and dampens it in the kitchen sink. Mom slips off the condom, and Amy caresses my dick with the cloth removing all traces on my cum. "Billy, get dressed."
Once I am dressed, Mrs. Donna tells Amy, "Your turn. Take them off."
Amy first takes off her pajama pants revealing white boy shorts and a camel-toe. I start getting another erection. She takes off her camisole and she is left in her underwear. I can see a hint of nipple on the side of the bra cup. She takes off her bra and reveals the rest of her nipples. Finally, her boy shorts come off, and now she is nude for my pleasure. She walks to her mom and settles herself on her mom's knee.
Her mom says, "Remember, spanking of a life time." She grabs to paddle just used on me and really spanks her. It was louder than I ever heard. Her ass turn red quickly, but her pussy is not wet. I guess it was too much. However, I have to perfect view this time watching or boobs jiggle left and right. Then again, it was hard to enjoy because Amy was in tears. Instead of thinking about my nude girl, I am worried about her.
It seemed like ten minutes pass before her mom stops. Amy slowly gets up, and puts her clothes back on. Mom and Mrs. Donna resume their conversation, and Amy falls into my lap and arms. She is still crying, but I'm caressing her and telling her that is going to be okay.
Now, it is really late, and Mrs. Donna announces that it is time for them to go home. We say our goodbyes at the door, and Amy gives me a good hug and a kiss on the neck. However, I do understand that she didn't fell like making out after all of that.
Last night, I still had to masturbate before I go to sleep. I am losing against my urges. However, I enjoy it so much. I try to beat off as quickly as I can. I wonder if Mrs. Donna's 'idea' will help me. But, I don't even want help.
I'm going to skim over the boring parts of today. Sunday. Mom is not working. Tell my Mom good morning. Take care of my chores. She doesn't mention about last night's masturbation.
It was decided to spend time at Mrs. Donna's pool. Awesome, three topless women in extremely skimpy thongs (which one is my Mom). Only bad part is me wearing a thong.
Same stuff happened like last time at the pool. Mom wore a large t-shirt first and is now topless. Mrs. Donna and Amy are also topless. Except I wore some shorts over my thong until I was ready to swim. Amy and I have a little fun in the pool making out, grabbing our asses, and I'm grabbing her tits. None of it is bothering our moms.
Now, Mrs. Donna tells my Mom, "Amy doesn't need to be punished today. What about Billy?"
Mom replies, "Well, he did masturbate last night." How does she know? "However, I'm too lazy to do that today. We'll postpone it for tomorrow. It arrives tomorrow, so we'll get to try it."
I reluctantly ask, "What is 'idea' Mrs. Donna had that is coming tomorrow?"
Mom says, "Don't worry about it honey. Enjoy your swim." So, I drop the issue. After a few hours of fun, Mom and I go home and prepare for bed. Tonight, I didn't bother jacking off so I wouldn't make tomorrow worse.
Mom works today so I wake up early to tell her bye before she leaves. As she is eating breakfast she tells me, "Sweetie, of course you know I'm expecting a package to arrive today. I don't want you to open the box. You understand?"
"Yes Mom," I reply.
"The ramifications will be severe if you even dare opening it. But, I really think it will help you out." She heads out for work.
While I do my chores, the doorbell rings. I find a box left on the porch and the UPS truck driving away. I look at the plain box and it has a generic return address without any mention of the company it is from. The box is small and light weight. I have no clue what it is. Of course, I make no attempt in opening it.
Mom arrives home. "Did it arrive?"
"Yes Mom, here it is", I tell her.
"Call Donna and tell her it's time for your punishment."
"Mom," I ask, "even if I was perfect yesterday and today, and not deserving a punishment, would I still be punished today? You know, because of that?” pointing at the box.
"Well...Yeah. I know. It wouldn't be fair. But, I need to see if this will take care of your problem." I grab the phone and make the call.
Amy answers, "Hello."
"Hi, it's Billy. Can you um...tell your mom that it is time?"
"Time for what, silly?"
I reply, "Time for my...punishment."
"Oh, you poor baby," Amy says. "That's right. That thing comes in today. Okay, we’ll be there soon. See you later."
I know this will be very embarrassing. When has one of these events not? The doorbell rings, I answer and greet them in. Amy gives me a big hug and a long kiss."
"Oh, I can't wait," Amy tells me. "I've been waiting for today."
"Wait for what?" I ask. "Why don't I get to know what's happening?"
Amy just smiles at me. Well, Amy is happy about it, so maybe it’s real good. Maybe we are allowed to have sex. Wouldn't it be weird our moms would allow this? However, what is this thing about?
"Okay," Mom says. "It is time. Billy, please remove your clothes for me." I begin removing my clothes. Once as all my clothes are gone, Mom starts opening the box. Inside the cardboard box is another box and it says "CB-6000s". She opens that box and unwraps a tube, a ring with an opening, and a few pins and parts.
"Sweetie, this device will help you," Mom tells me. "It prevents you from getting erections. It's going to be a little uncomfortable at first. Stand next to me and try to relax. It won't hurt."
I go to her, and she softly handles my balls checking it out. Through all my confusion I am not erect. She takes the ring and puts it around my scrotum. It squeezes my sack and pushes my balls up. She puts a few pens through the back. She takes the tube and puts my penis through the opening. She slides the tube into the pins and then places a small padlock through the hole of one of the pins. My penis fills the tube and my penis is completely soft. There is absolutely no room for me to get erect.
Mom asks, "How does it feel?"
"It's squeezing my scrotum."
"Does it hurt, especially your testicles?"
"No, not really. Just uncomfortable, like you said before."
"Good," Mom tells me. "It's called a chastity belt, or chastity device. It used to be made like a belt those goes all the way around your waist, but it is a very simple and discrete device. It will prevent you from getting erection, masturbating, and having sex. But, let us try to see if it works during your spanking."
Amy says, "Ah, it's so cute. I really like it." I wonder why she is so happy about it seeing my thing lock up like this.
Mom grabs to paddle, and I know the routine. I set myself on Mom's lap and my junk with the cage in placed between her knees. She starts the paddling. It is a light spanking. I start feeling to get a hard on. However, I feel my dick trapped in there, and I start to feel a little pain. Even though it is a light spanking, it is lasting forever. It is not comfortable with this thing especially between my mom's legs. Finally, Mom stops and I get up.
"Look, no leakage," my Mom says in enjoyment. "After all the money I spent on it, it really works. Okay honey, put your clothes back on.
"Wait," I interrupt. "You are going to...leave it on me."
"Of course," My mom replies. "You always masturbate at night. So we are going to try it for tonight. The only thing you need to know for now is that you will have to pee sitting down, and you will not be able to sleep on your stomach. Here is the key, I have a necklace for it, and I will put it around my neck to make sure you won't take it. Okay?"
"...okay Mom," I say. "I guess I really don't have a choice." I put on my clothes and find with the device on, I sport a little bit of a bulge through my shorts.
"Okay kids," Mrs. Donna says. "Joanne and I are going to my house to take care of some business. You two can stay here and watch TV or whatever you want to do. Just don't have sex. That's right you can't. Bye guys." Both our moms head out and close the door.
For the first time Amy and I am alone together. "I want to see it," Amy tells me. I can see the lust in her I, and I take no time getting up and removing my clothes again. Amy fondles and examines every inch of my manhood trapped in this cage. "It's not fair that only you are naked so I'll take my clothes off too."
"But," I interrupt, "you being naked are going to get me excited, but I can't."
"Come on, don't you like by body?"
Nothing I can do now. I tell her, "of course I do. May I?" I take the initiative. I start unbuttoning her blouse. After every button, I see more cleavage and her somewhat transparent white bra. I slide her blouse through her arms. I undo the top of her jeans and unzip them. I slide down her jean and see some white panties and also transparent at the top, but the transparency stops just below her clit. My penis is trying to get hard but has no room. I get up and reach my hands behind her and fumble with her bra hook. I finally get it after a few seconds and take her bra off. Her nipples are hard and begging me to put them in my mouth. But wait, no one else is here. I bring my mouth in and start kissing her right nipple. She lets out a loud moan.
I continue sucking on her nipple until she interrupts, "Okay, equal time for the other one." I switch to her left breast. After I feel like I given that tit enough time I back away. "Wow! That was just awesome. I didn't think it could feel that good."
After I stare in her gorgeous eye, I move down to her panties and slide them off. Amy sits on the couch and spreads her legs giving me my first view of her pussy spread out. I start to go down to lick that beautiful pussy. Then, the door opens.
"Amy!" Her mom shouts.
"Billy, what are you doing?" My Mom says sounding very pissed off.
"Did I say no sex?" Amy's mom says.
"Um...yeah. But we can't, remember," Amy slowly replies.
"We discussed that oral sex is still sex," Her mom tells her. "The first time we leave you two alone, you two are fooling around. Maybe it's not just Billy that is having problems with his urges. Now, put your clothes back on. Wait. Keep them off. Another spanking of your lifetime."
Amy gets another awful spanking.
"Billy, your turn," Mom tells me. I also get the worst spanking of my life time. My dick now stings and my balls hurt worse than ever. Both Amy and I have tears on our faces. First time I cried in a long time. Amy and her mom left in a hurry.
Mom sounded very pissed and said, "just go to bed. I don't want to talk about what I just seen." I can't believe we were caught just as I'm about to go down on her. I go to the restroom to pee first and had a little bit of trouble to get the stream to go through the slit on the tube. Therefore, I had to take a shower next. I felt powerless not being able to grab my junk during my shower. Eventually, I go to bed not knowing how to go to sleep without being able to masturbate. So, I just try going straight to sleep. I wonder how hard I will be when this thing comes off.
