1-Do You Have a Big Dick? Why Not? - Cover

1-Do You Have a Big Dick? Why Not?

Copyright© 2019 by Eddie Davidson

Chapter 16

Coming of Age Sex Story: Chapter 16 - A semi-true coming of age story with BDSM/fetish elements about a high schooler that meets a slutty girl, her mom and sister that actively webcam for a living and learns about dominance and submission. The story has been separated into sections so you can jump right in without the exposition and introduction if you prefer.

Caution: This Coming of Age Sex Story contains strong sexual content, including Teenagers   School   Mother   Sister   BDSM   DomSub   MaleDom   FemaleDom   Humiliation   Light Bond   Spanking   Gang Bang   Group Sex   Swinging   Interracial   Black Male   White Female   Anal Sex   Analingus   Cream Pie   Double Penetration   Exhibitionism   Fisting   Flatulence   Masturbation   Oral Sex   Pegging   Sex Toys   Tit-Fucking   Water Sports   Prostitution  

“I should put you on restriction!” Betty told Waverly that she was now on restriction after the finished laughing about my father’s corny reaction to them and nervous behavior. I walked up to them in their front yard with Hayden by my side.

“RESTRICTION! What the fuck for?” Waverly looked surprised and stomped her feet. “You just want to put me on restriction to be a bitch!”

“I had eight hundred dollars hidden where Jay would never find it and you gave it to him!” Betty complained to Waverly angrily.

“He would have beaten your ass for that money if he thought you were holding out on him,” Waverly said and added she wished her mom WOULD put her on restriction for that. I noticed that all of them had a habit of daring you to punish them by saying “I wish you would”. Hayden shrugged like she had no idea what was going on.

I knew that Betty was teasing my father about spanking Hayden’s ass. However, even if he had it wouldn’t have been that big of a deal to any of them. However, I felt really bad that Betty was going to punish Waverly for trying to save her mother from a beating.

“Honey, Jay was going to beat my ass anyway and I am a big girl. I can take a beating for eight hundred dollars!” Betty explained to her daughter like she was an idiot and should know that. “You gave him that money because he offered you cocaine,” Betty lectured Waverly as we walked to their backdoor.

I assumed we were walking to the back door so that Hayden could take her clothes off and get inspected but Waverly and Betty started to strip down midway through the backyard and step out of their clothes from the night before. They wanted me to hose them all down. The girls bent over and spread their legs apart like it was not a big deal to expose themselves in their back yard and held their legs apart for me.

It was daylight and there you could see through the fence where it had fallen apart. The fence was in disrepair like most fences in this neighborhood. It was missing boards or there were knots in the wood.

That same boy who teased Hayden yesterday about seeing her naked outside popped his head out and said he could see their bootie holes. It was like he had been hiding there the entire time and waiting for the opportunity or lived right next door.

“I know you can Luther. Want to come inside and take a closer look?” Waverly offered it to him like she didn’t care if he did or not and the boy ran off like a scared rabbit.

“You were nervous turning tricks?” Betty found that hard to believe. I put my thumb over the hose to build up pressure in the water line and sprayed their asses hard. They endured whatever I did to them as long as I didn’t get water in their eyes or hair. They turned side to side so that I could get them all over and let me wash them down while they soaped up with soap they kept outside. They told me their shower wasn’t big enough and years before they had fought over who got to use it first. Washing up outside had been Betty’s solution to tracking dirt in the house. “Obviously, when we started this little tradition we had a little more privacy where we lived,” Hayden told me.

“Yes, I was fucking nervous! OKAY? It was my first time walking track! I needed something to help get me through it! I am sorry, okay!” Waverly was still arguing with her mother about the restriction. She turned around and let me spray water all over her tits and held them up so I could wash under her boobs. I accidentally sprayed her face and she spit out the water and glared at me but let me wash her anyway.

The girls definitely didn’t like their face and hair sprayed. I told her that I thought she had cum on her face and Waverly admitted she did with a ditzy smile. Waverly licked her lips and said “Flavor savor,” and winked at me like she was used to having dried cum on her face too.

“You worked with half of the girls on the track at the club and most of the same customers were out there on the point. You bought the coke at the end of the shift! It wasn’t even that much,” Betty said angrily about the bargain she got for the coke.

“His blow wasn’t even that good,” Waverly admitted that the coke had been cut and didn’t do that much for her and rubbed her teeth as if she were trying to dislodge some dried cum or food particles.

I didn’t feel any sympathy now for Waverly because she had spent the money on drugs. Waverly nodded her head and said “How long then? A day?” she accepted she would get some restriction.

“You will be on restriction as long as Hayden!” Betty had left her sister’s restriction fairly open ended at this point.

“What? She wrecked the fucking car and did like 4,000 dollars damage. I just did 800 bucks. We could get that back tonight! Get Justin’s cute Dad to drop us off at the motel and I’ll earn it by noon.” She promised her mother.

I gathered from their argument that usually the girls were partners in crime or one of them manipulated the other into getting trouble so typically their restrictions lasted the same length of time. However, in this case they were two separate incidents and Waverly felt that what she did was hardly as bad as Hayden.

“You’ll earn the money back on restriction plus interest!” Betty insisted.

“Why are you so butt hurt about this? It’s not like I did anything that was criminal!” Waverly objected and thought her mom was over reacting.

“Buying coke is illegal, you air headed bimbo! I should dye your hair blonde again!” Betty insisted.

“Don’t you dare! Not for just one week of restriction! And selling ass out of a motel is illegal too, mom!” Waverly argued back.

That was a fair point.

“You need at least a week to cool off, stop being such a prideful, conceited self-centered bitch who only thinks about her needs because if an afternoon of restriction would fix you then I’d have you fixed,” Betty assured her daughter and told her to start calling her Mistress again effective immediately.

“I am a prideful conceited self-centered bitch. You have to look out for yourself in this world because no one else will! I like it. It is the way I am. Fine though, a week it is! You’ll get bored of whacking my fat ass in an afternoon anyway, and a week won’t fix me either,” Waverly accepted her mother’s punishment but warned her she would not follow through.

“I’ll just blow smoke up your ass until you get bored. Suit yourself,” Waverly acted like there was nothing wrong with what she did and the consequences of being on restriction were nothing to be alarmed about because her mother would soon tire of trying to fix her.

“Oh that’s why I have Master Justin now, and I want you well behaved for their pool party tomorrow,” Betty patted me on my crotch and held her tits apart so that I could wash her on the chest. All the water was getting all over my school clothes. I would have to undress to wash them down in the future but I think I was the only one terrified of being seen outside naked. My only consolation was that I’d be seen with three naked women and not just be this lone flasher in a backyard. I would have taken off my clothes then but the lurking boy had returned.

The ladies paid no attention to the black boy that had run away. He had returned and was obviously peeping behind the fence. They told me they had a lot of peeping toms and it didn’t really matter since they were on the Internet anyway as long as they remained harmless. I squirted the hose at Luther and he ran away again. They may not have cared because the more you scare them away the more they return.

“We aren’t really going to that thing? Saturday is one of our best days!” Waverly complained.

“It isn’t up to you now is it? Whose pussy is this?” Betty stuck two fingers in Waverly’s pussy roughly and held it apart for me to spray with water.

“Your Pussy Mistress Betty” Waverly reluctantly agreed.

“Now, go dig out your restriction thong, comb your hair and get your make up on. We’ve got some morning calisthenics to do for your audience,” Betty instructed Waverly to get in the house and get ready for punishment.

“What about breakfast Mistress Betty?” Waverly whined.

“Your fat ass can miss a breakfast. You swallowed enough cum last night to drown a horse,” Betty slapped her daughter on the ass and walked us inside after we finished expecting Hayden and Waverly together.

We were running behind for school but Betty didn’t care if we were late. She operated on a very different kind of time scale. That explained why Hayden was often in trouble at school for being tardy.

“Let me make you some oatmeal and you can tell me all about your sleep over,” Betty told Hayden as she walked her into the house.

“They fed me at their house, Mistress” Hayden explained.

“You ate properly or did they spoil you?” Betty asked her daughter.

“They spoiled me but I did freeze the oatmeal in the morning, Ma’am” Hayden answered submissively.

“Where did they take you to eat last night?” Betty asked skeptical of her daughter’s positive behavior. She knew it was probably an act. Hayden had been laughing and acting casually in the car and not talking with that submissive tone she took now.

“We didn’t eat out. His mom made us a Turkey dinner,” Hayden was very enthusiastic about that.

Betty looked at me and said “Well Law-Dee-Dah, I didn’t know you lived like Royalty, perhaps I was wrong about assuming you weren’t rich?” she asked me.

“We aren’t rich but my mom likes to cook. My Dad did give me a hundred bucks for expenses tomorrow though. It is yours if you want,” I handed it to her. “It won’t make up for the money you lost but it is something.” Betty saw the condom in my hand as well and realized my father had handed me that at the same time and smiled.

“He must be really proud of you?” she winked at me. She took his giving me money and a condom as a big compliment. “This is your spending money for tomorrow though,” she offered the cash back to me. I did not expect that. Betty had been all about extracting money from dumb men that wanted to give it to her.

“You take it,” I insisted. “I know it is not eight hundred dollars. You probably earned that pretty quick so this is really nothing anyway,” I shrugged.

“We barely got sixty bucks a trick out at that fucking truck stop motel,” Waverly seemed annoyed that I thought it was easy money. I hadn’t meant to make it sound easy to earn money fucking strangers. I thought they got more than that though. Sixty dollars was barely the cost of an Xbox game.

“Street Pussy is like delivery pizza. It was 10-20 bucks when I was in high school and it is still about that. The new girls that come on the lot get told the price and the old bitches out there won’t let them undercut by charging less or they will kick their ass, and the tricks won’t pay more because they are used to the prices,” Betty explained that it was a dog-eat-dog kind of system on the streets that never changes when hustling men.

Can I ask how much money Jay and Q let you keep of your earnings from last night?” I asked. I am just a naturally inquisitive person. I really had no reason to ask the question other than general concern that they had made at least enough to cover what they would have made doing cam shows.

Betty looked at me with pity on her face like I was Jon Snow in the North and didn’t know anything. “Pimps don’t let ho’s carry any money. He took all of it,” she said.

That didn’t sound right to me at all! They earned the money and they should keep all of it. I knew the pimp took some but I assumed it was like 20% like a Hollywood agent.

It was obvious from Betty’s body language that she didn’t want to explain that much more about how things worked on the street. “We owe Jay money so it comes off our debt with interest. We have to do little favors now and then for him. I know you were worried about me and I appreciate those sweet little texts. I am more worried that you are spoiling my daughter though. You see how spoiling turns out?” Betty held out her hand to indicate Waverly.

Betty told me that the Chinese webcam company took a good portion of the coins they earned every night as well. “There is always a pimp with his hand in your pocket trying to exploit you when you are exploiting men,” Betty shrugged that was just the way things are and always will be. We just had to learn to except it and get earn what we could. She did thank me for the hundred dollars though.

Waverly came walking into the living room trying to get a cotton white thong on that was clearly way too small for her waist. It was the same one that Hayden normally wore around the house. It didn’t cover most of the pussy crack or the entire ass crack but there was a white strand that covered the labia so that any wetness would be absorbed into the cotton. There was a triangle in the front and it wrapped around the waist like really tiny underwear. “I can’t get these fuckers to fit,” she said as she pulled the thong in the back through her ass crack.

“Those are mine, lard ass,” Hayden reminded her big sister and the two of them through a few insults at each other about not wearing panties normally and being too fat to wear each other’s clothes.

“Tell me about yesterday? Was this what you made Hayden where to school?” she asked as she looked at the outfit she came home in and looked over the butt plug and nipple clamps that Hayden still had on.

“Yes, I wanted her to dress slutty,” I explained. “It wasn’t too show her off. You told me not to do that. I just wanted her to feel beautiful and sexy. She always dresses in baggy clothes and I thought if she wore something slutty that would reinforce how other people actually see her,” I said.

“That’s cute,” Betty acknowledged that was a good idea and then said she didn’t tell me I couldn’t show her off. “I meant you couldn’t give her to your friends to fuck and make her do jumping jacks naked while they watch. I can hardly expect you not to want to be seen with a hot girl like Hayden,” Betty said that to Hayden as much as to me. It was rare she complimented her daughter but Hayden shrugged it off. She had difficulty accepting compliments –especially ones that didn’t reinforce her own self-image.

I noticed Hayden would talk about being conceited and stuck up and prideful and at the same time she thought she was fat and ugly. It was difficult for me to understand how she could think she was both at the same time.

UNCLE’S NOTE: YOU HAVEN’T TALKED TO MANY WOMEN HAVE YOU? THEIR LOGIC DOESN’T HAVE TO MAKE SENSE.

The girls casually joked around and put each other down a lot and I don’t think they usually believed it was serious. However, I could tell when Betty DID offer a rare compliment that it meant a lot to Hayden even if she shrugged it off like it was not true.

“You want slutty? These stretchy pants are Pilates Mom sexy. Let me show you what you can make her wear to school and you pick. I can’t expect you to understand the boundaries without a very detailed set of rules. Since I am too lazy to write those out for you we are going to have to take this a step at a time with our guidance,” she said.

I said I understood.

“I can hear your words but your face says you don’t. How much did you punish her at school yesterday?” she asked me.

“I didn’t have too. She was well behaved,” I said. Betty looked at me like that was obvious bullshit. I amended my answer to say “reasonably well behaved” before adding she had made some unintentional mistakes at best.

“if you don’t punish my daughter for even her unintentional mistakes and apply discipline then she will start to make intentional mistakes to get that discipline. Wearing slutty clothes at school can be a punishment for Hayden but I’d walked into her guidance office wearing what I had on last night. The punishment becomes a form of training that teaches her how to accept her place and not be so prideful. I’ve tried for years to get her to wear more appropriate clothes to school but she insisted on baggy clothes and I sleep late so I just really didn’t have time to fight this battle with her,” Betty said as she brought me to her daughter’s room. “We are going to change that, I am so glad we met you Justin!”

It was obvious to me that Betty’s idea of appropriate clothes for them was slutty outfits which was the opposite of what my mom would have said.

There in Hayden’s dresser closet behind a bunch of baggy shirts and jeans was a bunch of short skirts, half tops, tube tops, skinny low rise jeans, pleated plaid skirts, and even a full Harley Quinn costume with corset. Her mother started laying out the sluttiest outfits she thought we could get away with at school and even when Hayden shook her head that it would never be allowed Betty said to tell them to call her and she would straighten them out.

“I dare an administrator to tell me they can’t empower your body image or whatever. If they want to body shame you, I’ll be calling Action Line Nine,” Betty pretended for us how she would be hostile towards the administrator that dared to question her daughter’s clothing choices.

“I’ll walk in there with my cleavage out and if one of them even stares at me the wrong way I’ll say they are the one with the problem. Why should I change because they have to be creepy about the way they look at women?” Betty was on fire about that topic.

Waverly couldn’t care less. She said in her day it was simple. She went to school dressed like a slut because that is what got her passing grades.

“You dress like a slut because you are a slut,” Betty pointed out to Waverly and smacked her on the butt. Waverly was just standing to the side watching Hayden squirm as we chose her outfit for school.

“Obviously, you went with no bra and that is normally a good choice for most sluts. You want to see maximum jiggle and bounce. However, when you have honkers like we do a bra is essential. She doesn’t have the plastic surgeries I have had to make them stay up. All Hayden has is Mother Nature until your rich daddy buys her a pair. You want to pick outfits that show off the cleavage and support the tits and help them jiggle.” She could tell I had no clue when it came to the difference between a baby doll dress versus a sheath dress much less a corset and a bustier.

“Let Hayden present you with options that will please you,” she said knowing I was clueless when it came to this. “Hayden, how come you didn’t show him these when he said he wanted you to be slutty at school?”

“He said he liked stretchy pants, Mistress” Hayden explained.

“You see what spoiling her gets? Turkey dinners and look at this butt plug? Did you pick the tiniest one in my collection?” she popped it out of her daughter’s ass and stuck it in Hayden’s mouth to clean. “Go get a proper butt plug and sit on it for him, nothing smaller than Stanley!” she insisted.

Hayden acknowledged her mother’s order and went off to retrieve a butt plug from somewhere in the house.

Once she was gone Betty asked me if this was too much for me. She asked if I had been concerned about how she came on to my father. I said that I was having the time of my life and that my father will never stop thinking about this experience. I told her I wanted her to have the money. “He was so proud of me that he just spontaneously gave it to me and told me to swear not to tell my mother about it. That is on top of what I can pull out of the ATM.”

Betty thanked me and told me to use some of that tomorrow on Hayden. “I really am not a bad person. I am not Cruella Deville you understand. I know your father wouldn’t dare lay a finger on my daughter but if he did that wouldn’t bother Hayden. I was just having a bit of a laugh playing with his head because he looked so nervous. However, when I ask you to punish my daughter it is for her own good. You understand that? You will need to be much stricter or else she will start to take advantage of you. She will test you and push your buttons. She knows that. She’s been trying to tell you that she can’t help it.”

Betty asked me if we had a dog cage where I live and about what things I could get away with at my house. We did have a dog crate but our dog slept in it. Betty saw all the comforts we had as potentially undoing all the hard work she was doing giving Hayden severe domestic austerity discipline at home. Betty was pretty well convinced my house was literal poison for Hayden who would be sneaking out or fucking my Dad before too long.

I told Betty my Dad would never cheat on mom and Betty asked me if I wanted to make a bet. The way she looked at me told me she was pretty confident she would win that bet.

Hayden came back in the room and presented two butt plugs. One was made of latex and shaped like a massive triangle about the size of my forearm. The other plug was stainless steel and very fat and round with a diamond tip. Betty considered both and told her to bend over. She handed me the smaller one and told me to see how it looks.

I remembered to stick it in Hayden’s mouth for her to lubricate it and then shoved it in. Betty told me that was good and that I could also make it Hayden’s responsibility to keep it lubed several times a day. She asked me if I liked it. I loved seeing the glittering crystal in her butt cheeks. The circular base pulled her ass cheeks apart slightly so that you could see the entire circle.

“Fine, use the other one for training then. You will need to take some things back to your house if she is going to spend the night in the future,” she warned me. I assumed she meant that the stainless steel plug would be for everyday use and the bigger red one was for punishments and practice.

“Is the idea to stretch out her asshole with training?” I asked curiously.

“You have to stretch the muscles to work them out and tighten them. She needs to take bigger and bigger dicks and be able to grip them and hold them. Massage them with her asshole and cunt muscles. Get on the floor and show him your Kegel exercises,” Betty ordered Hayden to lay on her back and spread her legs.

Hayden put her hands behind her head and lay flat on her bedroom floor with her legs apart. She began to wink her pussy at me with the butt plug stuffed up her ass. She was even moving the butt plug slightly as the muscles in her pussy flexed. Betty told me to make her do that as often as I could “No more than an hour at a time though,” she said.

I couldn’t imagine exercising my dick for an hour. Hayden continued to obey her mother and let me watch her wink her pussy at me. She winked at me playfully and said “My pussy is down here, not in my eyes!” as she pointed to her pussy to get my eyes back where they belonged.

That was a funny twist on the joke of not looking directly at a girls tits when you are talking to her. I smiled and looked at her pussy.

I also let Betty know that my mom had already found the handcuffs, nipple clamps, and butt plug in her purse and how Hayden wore them under her clothes. I wanted her to tell me how to be more discrete.

Betty ruffled my hair and told me I was twisted but she liked my sense of humor. “Obviously, I don’t expect Hayden to crawl to breakfast at your family table when they are home but since she already knows we have one less thing to worry about. Do you mind if I flirt with your dad tomorrow at the water park or would that be too much? He is cute,” Betty told me it would be harmless. I smiled that would be fine.

Once we had agreed on Hayden’s regular butt plug then Waverly was told to wear a matching one. “Your two cute little asses can sparkle together,” she said as she pulled out a cane.

“Mistress, we are already late for school,” Hayden reminded her mother from the floor while continuing to wink her pussy. She was opening her lips and closing them without touching them. It was fascinating to watch. I could see some of her juices starting to drip down the winkles in her pussy.

“Since you are already late then you can be a few more minutes late. Tell them to call me and I’ll explain we were in prayer, now lay down flat on the coffee table so I can teach your boyfriend how to cane you,” she instructed Hayden to get off the floor and go into the living room and clear the coffee table.

Hayden lay flat on the coffee table with her tits pressed against the cold wood after removing the ashtrays and all the assorted junk. Betty told Waverly to stand with her hands behind her head.

Betty demonstrated how when caning from this position I should swing downwards like I was chopping wood at the lower buttocks when the girl is laying on her tummy. “You need to practice your spanking. Tonight, I am going to need you to punish both girls. You got away with just banging a paddle against Hayden’s ass last night but watch this,” Betty sliced into her Hayden’s ass with the cane and it made a satisfying swish sound and made her jump. There was already a dark bruise forming on the buttocks. “Give that a try,” she told me and Hayden counted out ten for me.

It felt very different. Betty told me to do the same to Waverly but hitting lower didn’t work. Betty showed me how coming across the very center of her buttocks would cause the least amount of pain. She had me come down from the top with my swing across her upper buttocks and then she made Waverly hold her ass cheeks apart and let me hit the tender flesh inside the crack.

“Owww, ahhh! It’s not fair to cold cane me,” Waverly shouted and tried to defend her ass cheeks with her hands.

Betty cuffed both of her daughter’s wrists to the coffee table. They had handcuffs on each of the posts of the coffee table already and had obviously used this table as a makeshift punishment rack before this.

I learned “Cold caning” was lack of a warm-up punishment and it was designed to be a cold, sharp dose of reality. Betty said the goal wasn’t to put her in “Sub-space” so she could meditate and forget about the pain. “You need pain in your ass because you ARE a pain in the ass! How else will you learn?” she made Waverly endure even more caning across her back and the bottoms of her feet while she punctuated that lesson.

I thanked Betty for the things she was teaching me and the girls did as well. They had too. Betty told them that they were expected to give thanks for the opportunity to be educated and to thank me as well for taking the time to learn to properly beat their asses in the most effective ways.

“Thank you Master Justin,” they both said sourly. I noticed Hayden became slightly less submissive when her sister was with her almost automatically.

Waverly rubbed her sore ass and complained that she needed to get warmed up to all this discipline because she hadn’t been on restriction in a while.

Once the lesson was over on caning I had to finish Hayden’s inspection before we leave and pick her clothes. I really didn’t want to make her a complete spectacle on my first day and get her kicked out of school but at the same time I knew her mom had said I needed to be more strict.

“You’ll wear this plaid skirt, this white top, and these saddle shoes,” picked an outfit that Hayden called her “Brittany Spears Oops I did it again” Halloween costume. The top was tight enough to hold up her tits but kept her nipples exposed. I didn’t attach the nipple clamps but I did make her go without panties and wear her butt plug. I also handcuffed her hands behind her back and told her she would walk that way to school from now on so I could keep an eye on her hands.

“Yes Sir, thank you Sir. That is wise. I may want to hug you,” she smirked. I lifted her skirt in the back and left it up so that her butt cheeks were completely exposed. “Look at that, you didn’t even notice how it flew up in the back. It will stay that way until someone notices and points it out or we reach school.” I told her that was her punishment. She would have to pretend she didn’t know her butt crack could be seen while she walked with me. I said it with authority and this time Hayden didn’t have a smart ass comment to add.

I would have to carry our books and her purse now that she was hand cuffed. Naturally, I didn’t mind. I would have done that anyway since like the old man from yesterday I generally believed that the guy should carry the books. I wasn’t sure if Hayden was a feminist and believed in equality of genders or if she felt women were naturally supposed to submit. I decided not to ask that question just yet though.

I packed her a lunch like the day before. Betty approved and when I suggested the Hot Dogs were bad she said that she would clean it off. She stuck the Hot Dog in her pussy all the way to the tip and then pulled it out and put it in the Ziploc bag with the raviolis, potato chips and breakfast cereal that I had also mixed together.

“I’ll notify the chefs at the Winter Palace to have roasted pheasant for dinner tonight, your highness,” Betty teased Hayden before we left about the turkey dinner we had last night. They made it sound like it was so much more than it was to me.

Betty noticed my little punishment and lifted the skirt up even higher in the back so that her entire ass was visible. “If you are going to have an accident, you can’t be too subtle or no one will ever notice. That isn’t fair. Give Hayden a fighting chance someone will care enough to point it out to her after I explained the deal I had made about when she could pull it back down.

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