Chapter 36

Ann drove me back to meet up with the others at Captain Hiram’s. It was a local bar where they liked to hang out. The bar was bustling, and the bouncers didn’t question us when she walked up. In the 1980s, the drinking age hadn’t yet become 21, and pretty girls were rarely carded. I had snuck in there a few times, but my mom always caught me.

You don’t need money when you are a pretty girl, either. You won’t pay a cover charge, and guys are always ready to buy you a drink. No one is going to offer you any food, and other than cum and my own pussy juices, I hadn’t eaten anything, so my stomach was grumbling. I was also walking funny because of the huge plug in my ass.

Guys stared at us as we sauntered through the bar to find my mom. She was at one of the bars with the other girls. They were flirting with men all around them. My brothers Buddy and Lewis were home being babysat by Lori and George. Kiwi was hanging around like a wallflower trying to fit into the rowdy crowd of tourists and locals.

A local band was playing Jessie’s girl when we walked in to the room.

“Oh god, what have you been doing? You missed everything!” Honey saw me and excitedly starting bragging about how many dicks she caught that night. “I fucked a son and his dad TOGETHER! It was his sons first time, and they paid to fuck me TOGETHER!” she bragged.

“What happened with Stan?” I asked her.

“Oh, he was a twisted weirdo! Very freaky,” she started to tell me all about it when my mom smacked my ass and told me to sit on the barstool and shut my yap. “You can catch up and gossip later. We are working,” she informed me.

We were there to flirt and find guys to fuck in the bathroom for money. Honey and Candy had been fucking and sucking all day long at the beach with my mom and Liz watching over them.

The first time a guy sent over a fresh round of drinks, I grabbed my white wine spritzer and downed it. My mom looked at me churlishly to suggest I shouldn’t try to get drunk. I smiled at her and then spread my legs slightly on the barstool and brought the wine glass between my legs.

I pissed into it and filled it up. I was surprised my pee was a much deeper yellow than Ann’s was. I sipped it at first and then spit it back into the cup. I smiled at my mother, playfully. I gargled a little and smiled even though my piss tasted like stale cheerios.

She smiled back at me. Then she looked at Ann knowingly. I began to drink my own pee in the glass, but I also backwashed some of it back into the cup. It was gross and disgusting, but I wanted to seem like I was willing to do whatever it took to prove myself to my mother.

“Show her the plug I bought you,” Ann said.

I smiled and turned around and flipped up my skirt playfully while parting my ass cheeks to give her a glimpse of the massive butt plug.

“No, I mean show it to her,” Ann said in a more serious tone.

I stood up and reached down between my legs. I saw men who were sitting close to us watch as I hefted the heavy plug out and then brought it to my lips. I kissed it clean and handed it to my mother.

“This is really nice,” my mom handed it back to me, and I kissed it to get it wet before returning it to my ass.

“I have one for each of you,” Ann told Candy and Honey that they would be getting bigger plugs.

“You can make us wear them when you graduate Summer School,” Ann said over the music that was playing in the background.

A man tapped me on the shoulder and asked me what I had just shown my friends. “That is my butt plug, Sir” I smiled at him.

“You like taking it in the ass, little girl?” he smelled of shrimp and brine and looked like a biker.

“Yes, Sir, I like it anywhere you want to put it,” I said to him with a smile.

“Let’s go then,” he took my hand.

“Twenty-five for head, thirty-five for half and half and fifty for around the world,” I said to him.

“You are a whore? They are getting younger and younger,” he released my arm in disgust.

“Okay, you can spend a few hours talking to girls and trying to charm them into giving it to you for free or pay me, and I’ll give you what you want without any effort on your part, Sir?” I flirted with him.

He took my hand and led me out of the bar before I had a chance to tell my mother where I was going. I hoped she wouldn’t be angry with me. He grumbled that I had better be worth it.

Once he got me outside, he threw me into his truck and piled in on top of me, pulling my skirt up and started to play with my wet snatch.

“Fifty bucks in advance, Sir,” I said.

“No way, I want to see if you are worth my time!” he grunted.

I wasn’t sure what to tell him. He didn’t want to follow the rules my mother had set. I wouldn’t get the money anyway, so I didn’t stop him. He ravished me in the backseat and put his hands around my throat to choke me. I could barely breathe, and I couldn’t stop cumming as the stout redneck dominated me with his body. He forced himself down on me even though I put up no resistance. I gyrated and wiggled underneath him and rode his stubby cock as he rammed it into me roughly. At first he asked me if I was a nasty girl over and over. I kept telling him yes but he only repeated the question while he humped me. He grunted wordlessly, and when he finally came inside of me, he threw me to the side.

“That was garbage, you just laid there!” he said.

“I couldn’t move under you, Sir! I was trying!” I begged him to pay me the money.

He tossed two crumpled ten-dollar bills on me and kicked me out of the truck before I had a chance to complain or eat his cum. “Get out of here nasty girl!” he shouted. My first real trick had only pulled my skirt up and popped my buttons off of my top, so I was still partially dressed. I got up and dusted myself off. I could have yelled at him and demanded more money, but he intimidated me.

I slunk back to the bar past the bouncers and returned to my mother. I handed her the two twenties.

“You just gave him head?” she asked me.

I could have lied and said that was all I did. She would have no way of knowing that he fucked me.

“No, Ma’am, he wouldn’t pay me in advance, and after he fucked me, he threw twenty dollars at me. I am so sorry, I know I was supposed to get the money in advance! He just wouldn’t give it to me,” I knew I was in for a beating.

“You are learning,” my mom took the money. “You should have referred him to Ann, and she would have made the arrangements. You don’t handle the money,” she said.

“I won’t be punished?” I asked with a tear in my eye. I felt guilty for failing to understand what I was supposed to do. The other girls had lots of practice tonight working the beach, but this was the first trick I ever turned by myself.

“You will be punished but not right now,” she said. She fingered me under my skirt and French-kissed me. Then she put her finger to her lips and tasted the man’s cum. She led me to the men’s bathroom and told me to squat in one of the booths. “Lap it up before you return,” she said as she stood over me in the stall and watched me squat.

My mom had a small purse and let me re-apply my makeup in the bathroom and clean up after I finished gobbling this man’s cum off the dirty floor. It was strange to be in the men’s bathroom, but it seemed like most of the guys in there thought it was a treat. They pissed in a big trough instead of individual urinals, and they only had two stalls.

As we left the bathroom together, I ran into Jack and Bruce. They were the boys I had been playing with for months that helped me throw the party. They were trying to get into the bar, but the bouncer wouldn’t let them in.

My mom went to the bouncer and whispered in his ear. I don’t know what she said, but he let the boys in. They looked concerned that she was going to yell at them.

“Don’t worry, boys, my daughter is paying for the damages your little party caused. I am not mad at you about it,” she smiled at them. She told them she knew it would never happen again.

“No, Ma’am,” Jack smiled at her. He was a handsome jock, but he seemed so immature compared to how I remembered him from before. I suppose because I had fucked so many adult men by this point that I realized just because he was a Senior in high school, he wasn’t really as mature as I thought.

“Do you guys want to fuck me?” I asked over the music.

“What?” Jack and Bruce were flabbergasted.

“Fifty bucks each and I’ll do you both in the bathroom or your car, Sir,” I said.

I could tell from Jack’s expression that he thought this was another of my many manipulations. He had spent months jumping through the hoops I created for him on an emotional roller-coaster that of pretending to want him only to pick at things he did and find reasons to reject him. It was all just to play with his head and wrap him all around my little finger by frustrating and confusing him. I was damned good at it too!

“Twenty bucks each and I’ll give you the best blowjobs of your lives, Sir” I smiled.

Jack and Bruce looked at my mother as if they were waiting to be told that this was not going to happen. She smiled at them. “Julie and Mandy are here too if you would rather have one of them,” my mom smiled.

“What the fuck, Blair?” Jack said.

“I go by Sugar now, Sir. Mandy is Candy, and Julie is Honey. This is how we are paying back mom for the damage we’ve caused,” I said.

“No fucking way,” Bruce seemed floored by this revelation.

“Yes, fucking way, sir,” I said.

“If you change your mind, we’ll be over there,” my mom said and led me away. She told me to cut bait after five minutes with young guys. “They usually have no money, and they want to chat endlessly. Old guys are where the money is,” she said.

I wanted to give Jack and Bruce a piece of me because I felt they had earned it after all I had put them through. They seemed intimidated by my offer. My mom told me that I needed to learn to be more subtle. “You are going to eventually proposition an undercover officer, and you’d go to jail. It is okay to ask old fuck buddies like you did, but you need more practice, I’ll show you after the wet T-shirt contest,” She said.

The wet T-shirt contest was the main event, and it was one of the reason there were so many guys at the club and so few women. The women that were there were hopeful contestants. There were some cute waitresses hoping to make a buck. My mom said they would be easy to beat.

There were a couple regular strippers who worked the wet t-shirt contest circuit. My mom said they come to all of the tiny bikini and wet t-shirt contests up and down the Florida coast and are stiff competition.

The one girl that my mom didn’t want to be there was also there. Betty Welton the freshman with huge tits and porn star looks arrived just in time for the contest. She was flanked by a handsome grey, haired gentleman who looked very wealthy. She was dressed like a slut in a white, flimsy top and made a spectacular entrance by flipping her shirt ‘accidentally’ at the door to flash the crowd.

“That fucking cunt will soak up all the attention,” Ann lamented.

“Don’t be jealous,” my mom teased her. She turned to me and said the same thing.

“We aren’t here to win this contest. The prize money is nice, but the goal is to get attention. Pretend to be drunk and horny, and at the end, you’ll have tons of offers from guys to fuck. Tell them you’d love to, but it isn’t up to you. Tell them to talk to your Mom, and I’ll make all the arrangements,” mom informed us that WE would be in the competition and afterward we would fuck whoever offered the most cash to take us home.

“Kiwi!!” Betty hugged Kiwi and pressed her huge tits into his body. He was her cousin, and he was supposed to be visiting her instead of staying with us. He smiled at her politely. Kiwi had certainly matured tremendously since he began his stay with us. This wasn’t the summer vacation he expected for sure. He didn’t seem overwhelmed by Betty’s attention or flummoxed with a boner because boobs brushed against him.

“Heya Betty, nice to see you,” Kiwi said politely.

“This is Jeffery Epstein, my boyfriend,” she introduced the older man behind her. He could have easily been her father. The man seemed unwilling to admit to being her boyfriend, but he smiled politely.

“You girls are so awesome, I’ve heard all kinds of naughty rumors about you!” Betty told us sweetly. “If half of them are true, I want in! Let me play!” she seemed to beg my mom.

“The girls are in a disciplinary summer program. They have lost all their freedoms and must obey their mum,” Kiwi explained.

“Ooh, that sounds awesome,” Betty slid up to her cousin and begged him to tell her more.

Kiwi quickly explained that we were spanked, caged, bound, and made to clean in the nude. He said we had to obey him, and she would to if she was part of the summer program. He was trying to scare her off, but it only made her more fascinated by my mother’s program.

My mom told her that she was far too advanced to be in her program, and she didn’t have room. Betty didn’t think that was fair and tried to flirt her way into the program. I was shocked that my mother was adamant about it.

Her boyfriend stood behind us, watching this discussion unfold. “I’ve got a private island. If you want to play dirty games, I am sure I can think of something,” Jeffery promised her.

“Please guys? I want to play with you,” Betty pleaded.

Ann was about to tell her to take her big jugs and shove them up her ass when the DJ announced it was time for the wet t-shirt contest. It was the 1980s, and cheesy DJs with oversized sunglasses and outrageous costumes weren’t played out clichés.

“I am Mikey D, and I came to see! Who out here has the biggest titt-ees!” a white guy jumped out with a cordless microphone and rapped over the Sugar Hill Gang’s Rapper Delight beat. It was super stupid, but everyone started cheering and clapping anyway. “All the lovely ladies who want to get in my game come on up and give me your name!” he rapped.

Mom coaxed us forward and sent Liz as well. It was my first wet t-shirt contest. The DJ took one look at me and said, “You are in it to win it!” – I felt so validated. He took one look at Honey and said, “Wow, you’ve got titties for days!! I’d love to motorboat those hooters!!”

Honey shook her tits for everyone, and the crowd lit up with applause and laughter.

Candy walked up and took her top off and then threw it over her head. The crowd became electric. “Oh my, this one is ready to start the show! Leave a little to the imagination, sweet cheeks!!” the DJ said in his corny DJ voice.

When Betty walked up to the stage, the entire room stood up and began chanting. I had gone from feeling like a superstar to feeling like second banana. Betty was spectacular, and she danced like a professional. She was born to be on stage like this and looked like a girl that stepped out of a Centerfold from the 1980s. She had the big blonde hair and the bold, puffy nipples sitting on top of two enormous naturally huge tits. She had a butt that wouldn’t quit and hips for days. She was a little short but her legs were muscular and shapely.

I saw a few girls walk away after she got that standing ovation. “Now girls, don’t go away mad! Just go away,” the DJ joked with them as they walked out. “Come on back! Hey there is a second-place and a third-place prize! Fifty dollar bar tab and a Captain Hiram’s T-shirt!!!”

The contest eventually had twelve contestants. We were each provided with white half-shirts to change into behind the stage. They were see-thru, so it really didn’t matter, but it helped build up the anticipation to the crowd.

Betty had a penis-shaped pendant on a chain around her neck. She opened it and snorted a line of coke just before the contest. She offered me some, but I didn’t take it. I would have if I wasn’t in training.

I think one of the reasons I liked drinking and doing drugs prior to my training was that it allowed me to stop being Blair for a little while and stop thinking. It made me feel less evil. I no longer needed drugs to feel that way.

I was so nervous that I almost threw up. All the eyes in the house were on me, and I felt like some of them would figure out I was just an immature school girl who didn’t belong there. I held my tits out, clenched my butt cheek, raised my chin like I had been taught, and stood in line with the other girls, and no one told me to get off stage. I felt that was a small victory.

The DJ alternated between playing AC/DC’s Back in Black, and You Shook me all night long while guys from the audience were asked to pour water on us while we danced.

Jack poured water on my tits, and the crowd went crazy. I lifted my skirt and turned around and bent over and wiggled my ass. I realized afterward that the reason I had such a huge ovation wasn’t just that they saw my entire pussy but that they could see that huge butt plug glittering in my ass cheeks.

I came in second!! Honey came in third, and Liz and Candy did very well as crowd favorites. All in all we were very pleased with the reaction of the audience.

Naturally, Betty won the contest, and Jeffery whisked her off to wherever they were going to go to party after that.

Most of the men started to filter out after the main event however, as my mom predicted, a lot of them came over and wanted to talk to me. I giggled and said, “My mom decides who I date. You’ll have to talk to her,” as guys fondled me and pressed in close to talk to me.

Jack and Bruce walked up while I was talking to several guys. “Are you still up for what you discussed earlier?” They asked me.

“My mom decides who I date, sir!” I told Jack coldly. He had his chance to have me earlier and now it was up to the highest bidder. I knew he wouldn’t have the cash to outbid any of them. There were a lot of really nice looking, older men that were interested in me.

It was a very surreal feeling to have no control over who was going to take me home that night. It was the first time I felt like I was being auctioned off and strangely instead of making me feel like powerless cattle I felt like something valuable and worthwhile.

I know I was supposed to feel humiliated that I’d have to fuck an old man. I know I was supposed to feel powerless that I had no choice who I spread my legs for. I knew I was supposed to feel like an animal to be traded for money and a whore.

I didn’t feel proud or vain. I didn’t feel like a superstar. I think that is what Betty got out of winning that contest. She certainly didn’t need the prize money. The cocaine she snorted prior to that contest probably cost more than what she won.

I don’t even remember who bought me that night. He was a nice gentleman, and I can’t tell you too much about how he fucked me. My mom had to rent us rooms at a local motel. She normally fucked guys in her bed, but there were too many of us to share her room.

That next morning after fucking a total stranger twice my age my mom came to pick me up. I got in her car completely naked without complaint and kissed him goodbye and never saw him again.

The next day my mother began training my little brothers how to dominate me. She made me kneel before them and pledge myself to obey them. Mom said she didn’t want me to intimidate them, but she also didn’t want them to think they had total control over me, and anything goes. I asked her what I should say, and she gave me some guidelines but told me I had to speak from the heart.