Chapter 27

“That is why boys normally aren’t allowed to sleep with shorts on!” Stacy pointed to my hard dick wedged in my shorts. I didn’t understand at the time what she was saying. A boner was perfectly natural for me. They explained that in their house, boys were allowed to walk around hard all the time. The boys were expected to masturbate at set times during the day. The girls considered it a biological function. The act of masturbating cleared the boy’s minds of dirty thoughts and made them less horny and mischevious. As far as the sisters were concerned, it was not much different than eating or going to the bathroom.

The promise of fucking the two saucy girls in the butt was enough to get me out of bed and aroused. Once they explained the way they saw unexpected erections, I was embarrassed they saw me hard. If two nearly naked girls climb in my window and offer me butt sex in the middle of the night, I wasn’t going to let some embarrassment stop me.

Stacy and Waverly didn’t seem that concerned once they noticed my boner. They acted mildly annoyed, but otherwise, it was a perfectly normal biological reaction for a male to them. They had grown up knowing about boners. I couldn’t imagine the same maturity coming from any of my siblings about the issue.

The two blonde girls began to step out of their thongs. Stacy didn’t want to take off her pasties, but Waverly insisted we go all in and run to the trailer park and back completely naked. They expected me to undress as well.

“This isn’t a trick? You are really going to let me fuck you both in the ass if I win?” I said as I shimmied out of my shorts. I wanted to wear shoes, but the girls insisted that it wasn’t part of the rules.

“If it was a trick, would we tell you?” Stacy chuckled at how naive I sounded.

Waverly pulled a butt plug out of her ass and showed it to me after she cleaned it with her mouth. The stainless steel plug wasn’t that big. The base had been decorated with a circular Beyblade POG top. They were once popular anime based tops that you were supposed to spin with your friends and have battles.

“Pretty cool,” I said as if I were impressed.

“If I am willing to shove one of these rubber ding-dongs in my booty hole just for fun, then what difference does it make if I let you shimmy that dong of yours up my ass?” Waverly placed her butt plug over my hard cock to show me it was almost as wide as my dick.

“Then why do I have to win the race? Why not let me fuck you in the ass if I go with you?” I asked.

“Fine,” Waverly shrugged and looked at her sister for confirmation on the agreement. She wiggled the nub of the plug around her asshole and pushed it inside of her.

“I don’t want to be fucked with the same dick that has been in your ass,” Stacy scrunched her nose like that was disgusting.

“Don’t be silly, Stacy” Waverly reminded her sister that she could clean my dick off with her mouth before it goes in her ass.

“That’s a good idea,” Waverly spread her cheeks for me and showed me she wasn’t wearing a butt plug. “Do you want this?” she asked me.

I remembered what Claire asked me earlier about if she was a backup plan or an upgrade. I definitely wanted to fuck both of these silly girls. They were offering anal sex. I was even willing to risk getting caught to be able to do it. It seemed worth the risk.

“Yeah, I’d like that a lot,” I said.

They chuckled like silly girls and led me out the window of my bedroom. We were completely naked.

“You jumped out of the bed like you’ve never had anal sex before,” Waverly said to me as we jogged naked through our neighborhood.

I wanted to lie and say that I had plenty of times, but I told the truth.

“Never,” I admitted.

“Wow, that’s crazy!” Stacy acted like I was from the Opposite planet, where everything was the opposite of the Earth.

“You didn’t start giving up the booty until two years ago!” Waverly teased her sister. I liked jogging slightly behind the girls. They did have plump little asses, and it also helped avoid them seeing my hard dick flopping up and down as I ran.

“That is because mom said I couldn’t,” Stacy insisted with a pout.

“Your mom knows you have anal sex?” I found that interesting.

“Yeah, so? Do you think she wants us getting preggers?” Waverly rubbed her tummy to indicate a baby in her belly. That did make a little sense to me. One reason I was always painfully shy around women was that I was afraid I would put my foot in my mouth. If I didn’t say anything, then that couldn’t happen. I also couldn’t arrange to butt fuck two sisters either. I was feeling rather cavalier and confident.

“How many times have you done it?” I asked as we jogged.

“Get fucked in the ass? Today? Probably only twice, but I had an enema if you are worried about shit on your dick,” Waverly answered bluntly.

I nearly tripped when she said that.

“With who?” I was shocked.

Waverly turned her head as we ran towards the nearest wall and gave me a look like it was none of my business.

“Once was with Lewis. He did a good job cleaning my room,” Waverly said she couldn’t remember who the other one was.

“That boy you met at the pool?” Stacy asked.

“Oh yeah, there was a boy I liked at the pool,” Waverly remembered like it was a trivial matter who she had sex with.

“Let’s rewind,” I reminded them that Lewis was one of their brothers. “You have sex with your brothers?” I asked.

They both winced at me like I was disgusting.

“I guess you could say it is technically sex. I let him hop on my back and do his business. It isn’t as big of a deal as you are making it,” Waverly said. She had a stubborn look on her face that insisted what she was doing wasn’t sex, no matter how much I inferred it was.

They explained that there wasn’t any emotional exchange at all. “If he does something I want him to do, then I let him get a quick nut in my butt. You don’t do that with your sister? Do they even let you jerk off on them?” they asked me like I was crazy.

“You have to be putting me on. They jerk off on you?” I said.

“It washes off with a warm washcloth. What is the big deal?” Waverly explained it like she assumed everybody did this in their household.

“We run around naked all the time. It turns guys on, and they get hard. You’ve got a boner right now. You can’t help it just like I can’t help getting wet when I think dirty thoughts. Mom would rather the guys jerk off on us than seek out porn or weird girls. It really isn’t that big of a deal,” Waverly said.

Stacy said she liked being glazed. The girls called, getting creamed on being glazed like a jelly donut.

“So whenever they want, your brothers can whip out their cocks, and you’ll stand there, and they masturbate on your face?” I found it impossible to believe.

“No, you have the wrong idea,” Waverly said. I was somewhat relieved. I found it incredibly taboo and loved it, and for that same reason, I found it impossible to believe anyone’s family life allowed for this.

“The boys are permitted to masturbate three times a day at home. They can pick one of us, and we give them a few minutes to pop their load. All we have to do is stand there and let them look at us. They can think whatever they want. They can’t touch us. They shoot their goop on us, and then we go wash it off,” Stacy explained.

Waverly said it was great for the skin.

“You go to public school, right? You have to know that most people don’t do this in their homes?” I said.

“Mom always says who gives a fuck about most people? why would you want to be most people, anyway?” Waverly shrugged.

“We don’t run around naked at school if that is what you are getting at,” Stacy assured me.

“I wasn’t suggesting you did. I just mean, do you tell boys at school you like to take it up the ass?” I asked.

“Yeah,” Waverly shrugged that it was easy to make friends that way. “You don’t think vanilla girls take it up the ass for the same reason?” she said.

She had a point there. They were just so unrepentant and open about it that it was unnerving.

I couldn’t imagine spanking one out on my sisters. I would have liked to have seen Lindsay’s face if she had to stand there and let me, though.

It did seem logically consistent to me that girls raised to think nudity and butt plugs were perfectly normal in public might have a very modern approach to sex. As far as they were concerned, it wasn’t sex. It was a favor they were doing a horny boy to let him dump his load in their back door and nothing more.

I wasn’t sure if I was still flattered, they had offered me their asses. I was still going to do it if I got the chance, mind you. I just wished it was a bigger deal to them like it was to me.

It was still surreal to me that I was running around in what appeared to be a typical upscale housing development without any clothes. No one was on the streets. I wondered if I could get away with this in a vanilla community. I wondered if the trailer park was clothing optional or not.

“Is this trailer park vanilla?” I asked them. I meant is it clothing optional.

“Everything outside of Sunny Manor is clothing optional,” they told me as we reached the wall. I had to help them up by pushing their sweet asses above my head. I spread their butts and looked straight into Waverly’s slick wet pussy as I did.

“If you choose the option of going naked though you could get arrested if you get caught,” Waverly smirked once she got to the top. She offered me her hand to help pull me up and told me not to get caught.

“Now watch this moat,” Waverly told me once I struggled my way to the top of the white medieval-like wall that surrounded Sunny Manor. “There are alligators and poisonous snakes in there,” she said as she hopped down and began swimming.

I was nervous, and she looked back at me and smirked. She was poking fun at me. I resolved if the girls crossed without fear, then I would cross. I let them go first, though, just in case.

We waded across, and I had to admit that there was a new electric charge in the air once I left the confines of Sunny Manor.

It was purely in my head, but realizing I was no longer in a private community that condoned nudity made it seem far more risky to run around in the humid Florida wilderness.

There were no street lights and nothing but swamplands around the gravel road that led up to the trailer park. There were plenty of gnats and mosquitos to keep us company. I kept slapping myself to keep them off me.

Stacy poked me quickly in the nuts and said that she saw a mosquito on me. Waverly chuckled and announced, “Quarterback Sack!”

I slapped Stacy on one of her bald pussy and said playfully, “Wide receiver!” She was wet, and I felt her entire clit hood when I slapped her pussy with the palm of my hand.

Stacy regarded me like I had done the unthinkable for a minute. I was about to apologize. I shouldn’t have spanked her on her pussy. When both girls laughed and kept running.

It was longer than I thought it would be to the trailer park. I was getting tired.

“Can’t make it?” Waverly stopped. She was breathing heavy.

I was willing to go on. I had to if I wanted that booty - and I did.

I trudged on to the trailer park. There were about sixty trailers, and they looked broken down and rusted out at night. They were close together with very little yard space. It was a stark contrast to the pristine Sunny Manor. There were industrial buildings and what appeared to be a water treatment plant very close to the trailer park. It didn’t seem like an ideal smell to have wafting night and day through your windows.

Florida is balmy anyway, and we were coated in a fine sheen of our own sweat. I could smell the girl’s pussies, and I have to admit that despite a distinct fishy smell, I liked it. There must have been pheromones in their pussy juices that made me love it the way dogs love other dog’s butts.

Waverly pointed to four points around the park. The fourth one was a large Banyan Tree that was in a sad little rickety park with broken downswings and a bent slide.

“Sodomy,” I thought to myself as I watched the sister’s asses jiggle in the moonlight. It was something the bible probably forbid. There was probably more porn of people doing that then there was vaginal sex on the Internet.

It seemed so taboo for normal people but something that porn stars did as their every day 9 to 5 job. Waverly and Stacy didn’t seem to have any reservations about letting me nut in their asses. I had no reason to think they were teasing when they made the offer. All I had to do was finish this lap around the trailer park, and I’d be able to fuck them both.

I was still technically a virgin unless you count some light finger fucking and a blowjob. I was going straight to the major leagues by skipping the vagina and fucking TWO girls at once in the ass.

I think it was the excitement that caused me to trip over a garden hoe and faceplant on the dirty street just outside of the trailer park.

“Leave that hoe alone,” Waverly laughed at me as she made a play on words.

I brushed off my dirty knees. I was fine except for a few scratches. I was ready to continue with our little game.

I nearly jumped the first time a yapping dog noticed us. It was late on a Sunday night, and most people had gone to bed.

I say most people because there were still a few people up and about.

“Oh my god, those boys go to my school!” Stacy yelped and dashed behind an old white van with her sister.

I thought they were extroverts who didn’t care who saw their naked bodies?

Suddenly, three boys about my own age look in my direction because they heard Stacy when she cried out.

“Flasher!” the boys didn’t hesitate to chase me. They thought I might be some pervert who was probably peeping in windows and trying to flash them. I wasn’t going to wait and let them catch me to explain.

I began to dash and dodge and weave around the various trailers. I Tripped over garden hoses and stepping in dog shit people didn’t pick up. If I hadn’t fallen into a ditch because I am clumsy, they might have caught me and beat the snot out of me.

Instead, I ended up with a little mud on my face. I hid down in the mud with the frogs, crickets, and who knows what else. I looked up at the Florida moon and wondered if this had been the girl’s cruel plan all along.

Promise me anal sex and then ditch me as soon as we got to the trailer. Imagine if Charley Brown went to kick the football and instead of one girl pulling the ball away, but TWO girls do it. He still lands flat on his ass.

Now imagine that football is the promise of first time anal sex! That is precisely how I felt.

“What are you doing down there?” I heard Waverly chuckle from the street with her hands on her hips, “beating off?”

“No, I was waiting for those boys to stop chasing me,” I tried to brush the mud off my body, but I only managed to smear it in more. I hoped it was mud after I smelled it. It had a foul, sulfurous odor to it.

The girls looked excited about being out here. I was probably looking pretty grim and miserable.

I followed when they took off, running around the edge of the trailer park again.

“Why did you hide when those boys came after us?” I asked as we jogged around the perimeter. “I thought you were comfortable being seen naked?” I said.

“Yeah, but that is IN Sunny Manor,” Stacy shrugged like that should be obvious.

Her big sister explained it was like the difference between being comfortable naked in the shower or walking through a shopping mall.

“If the same boys lived in Sunny Manor, they would have seen you naked, though?” I didn’t understand.

“They don’t live there, though. It is bad enough that kids at school know our bus stop is Sunny Manor,” Stacy said.

Her sister explained that guys often think girls that live there are easy and want to fuck them.

“You said anal wasn’t even that big of a deal?” I reminded them both. We were nearing the tree and the final stretch of the trailer park.

“Yeah, but it isn’t like a boyfriend-girlfriend thing. Guys at school ask us out on a date and expect we’ll do all this freaky shit with them,” Waverly said.

“You served your brothers on turnabout day,” I pointed out what I felt was the illogical inconsistency of what they were saying. “Wouldn’t you be happy doing freaky stuff with a guy at school who is NOT a blood relative?” I asked.

They looked at each other like I just asked why Apple Jacks taste nothing like Apples. They had no explanation other than it just does.

“Boys that live outside of Sunny Manor only have fantasies and porn to rely on. Our brothers have been raised in a female-led household. I guess we trust them, and it isn’t sexual to us. The things vanilla boys at our school would do to us would be a lot different,” Waverly said.

Stacy looked like she might consider it anyway.

“Have you two ever dominated each other?” I changed the subject.

Waverly and Stacy stopped jogging and looked at each other with a wicked grin. It is evident from their expression they had never thought about it before.

“Why would we do that?” Waverly said after they started jogging again.

There were a lot of reasons I could have suggested. The one that sprang to mind first was it would be hot to see two sisters dominate each other in a lesbian BDSM relationship and be an incredibly hot fantasy. The fact that they looked so similar to one another would have made it even more taboo and sexy. They weren’t twins, but Waverly looked just like a slightly older version of her sister.

“You have turnabout day to put yourself in the place of a submissive and see things from their perspective,” I said instead.

“Yeah, but also to give our brothers a chance to get even with us if we pushed them a little too hard or were extremely rude. It’s incredibly easy to get on a power trip when you are in charge,” Waverly added that caveat.

“You are never rude to your sister?” I smiled, my answer.

The girls stopped again and looked at one another. It was clear from their expression that I had made an understatement. Big sister Waverly and Stacy were often competitive with another and rivals.

“Yeah, but it isn’t the same because my sister can be rude right back. My brothers would be punished for insolence and sassing us,” Waverly said, and the girls continued jogging into the night.

We touched the banyan tree. It was a giant solitary tree with aerial roots that had probably been growing for decades. It was sad to see the noble tree littered with garbage and spray painted with graffiti.

“Do they remain polite because they are polite or because there are consequences if they aren’t?” I asked. I had been thinking a lot about dominance and submission.

Waverly said her brothers were naturally polite and wanted to be good boys.

“Are they always polite when they are in charge of you?” I asked.

“Oh, definitely not! They make us push our noses up and oink like piggies,” Waverly showed me by lifting her nose and snorting. Stacy did the same thing and showed me her two buck teeth as she did.

“You might be more polite and helpful to one another if you were to have turnabout day between the two of you,” I suggested.

Stacy scrunched up her nose and said she’d never want to serve her sister.

“Why? chicken?” Waverly teased her younger sister.

“No, just you’d probably make me do a lot of dirty stuff in the living room in front of everybody!” Stacy said. I had fun picturing that dirty stuff in my mind. I imagined deep knee-squats and a wooden cane for starters.

“You would be able to make me do the same thing,” Waverly assured her.

“Are we talking about just a day?” the girls asked me if that is what I had in mind. I didn’t expect they’d let me define their turnabout rules.

“I think to understand how it feels to submit and have consequences, you should spend at least a week serving each other,” I suggested while trying to suppress my wicked grin. I was trying to appear helpful, but I was fantasizing about two girls spanking each other’s asses.

“You wouldn’t obey me for an entire week,” Waverly accused Stacy.

“I would if you would! but you definitely couldn’t handle obeying me for a week!” Stacy assured her big sister.

“It sounds like a bet,” I said.

The girls looked at me like I said the magic word. I had their undivided attention. I didn’t think of the bet in advance before I said anything about it, but from the look on their face, they were intrigued.

“You have to submit the same way you would for your brothers during turnabout day - just for your sister. If in that week you refuse any order, then she wins!” I said.

“What do I win?” Stacy asked with excitement in her eyes.

“I would be the one who wins!” Waverly assured her sister and asked me to define the stakes of the bet.

I really hadn’t thought about what the winner gets. I was happy I could think up a bet that intrigued them. I assumed they wouldn’t agree to spend another week in submission if they had already refused an order.

I couldn’t think of anything else that made sense. I decided to rely upon the wisdom of Dicktatress Moxxi to think of something.

“The loser begs her mom to punish her for disobedience. Your mom will adjust your attitude and decide if you should continue your week or extend it a little longer!” I said.

They high fived in front of me with big smiles on their faces.

“Hey, can we do the anal sex now?” I asked. It seemed like the best time to ask was when they were happy. We had made it to the tree, and I was ready to collect.

They looked at me like I couldn’t be serious. I was about to go off on them for dragging me out here in the middle of the night, getting me coated in mud, nearly beat up, I stepped on a garden tool and landed flat on my face.

“We need to wash you up first! Can we do it in your bed?” they both asked me. I was glad I hadn’t become a sourpuss because they were still quite willing. I am sure I smelled pretty ripe and looked even worse. I agreed and asked them to start running back.

“So, who is in charge for the first week?” I asked as we began to run back to Sunny Manor. It is not lost on me that the fantasy of the two of them dominating each other was incredibly sexy to me. At the same time, the idea of Lindsay telling me to take out the garbage and being able to spank me for it was anathema to my very existence.

Then again, Charity would do all the chores around the house. I started to realize it may not be so bad to be submissive for a little while at our house. Dad would never make me do half the stuff Kyle did, and Charity already handles all the chores.

The girls bickered back and forth on who got to be the domina of the relationship first.

“Whoever’s butt I cum in first tonight gets to be the first one in charge,” I said with a cavalier attitude that seemingly came out of nowhere. I wanted to give them some incentive to turn me on and make me cum.

Stacy scrunched up her nose at me in disgust.

Waverly looked over her shoulder at me like I must be kidding.

“If you stick it in my ass first, then I’ll make you cum!” Waverly insisted, and she wiggled her butt as she jogged. I have to admit Waverly was really stacked in terms of boobs and ass. She had a face like Sam from iCarly but an ass like Kim Kardashian.

“No, I can make him cum faster!” Stacy insisted.

Listening to them argue over who had me first was worth stepping on a garden hoe, falling in the mud, and being chased by angry boys. I

“How about I fuck you both in the ass, and I decide who I liked better?” I decided like I was a young King Solomon.

They both quickly agreed to let me make the final decision.

“You’ll serve me for an entire week?” Waverly asked her sister to confirm she would.

“He is going to pick me first,” Stacy assured her sister that she was convinced she would be the one in charge. It was Easter Break, and that meant the girls had the entire week with no interruptions from school to dominate the other. I was massively excited by the idea myself and running with a hard-on.

They kept giggling and making devious stares in my direction as I jogged behind them to ogle their asses.

“If you do win,” Stacy asked her sister with an impish grin, “will you make me give blowjobs to any guy you want?”

“Hmm, that means when it is your turn, you get to make ME do that?” Waverly considered her sister’s question carefully. Stacy nodded her head, enthusiastically that she would.

“We should probably have limits,” Waverly said “Whatever our brothers can order us to do on turnabout.”

Stacy looked disappointed and a little horny. “They can jerk off on us, and make us give them handjobs. Can I make you let other guys do it to you?” Stacy asked sweetly.

“You are the one who is going to be my pet. I’ve got the prettier ass!” Waverly assured her little sister and winked at me.

I couldn’t be more excited about how things worked out. Even swimming across a dirty moat a the muggy Florida swamp didn’t bother me. I barely thought about the snakes, alligators, and fish that were probably lurking around underwater, just waiting to bite into my junk. I didn’t mind slapping the mosquitos. I didn’t mind scratching my balls on the cement as we made the arduous climb over the walls.

“At the end of the week, you will swap roles anyway, and the one who was in charge becomes the pet,” I reminded the bickering sisters.

I hadn’t intended to shoot myself in the foot by mentioning it. I just wanted the girls to be aware that it was only fair they swap roles after the first week. I need to learn to keep my mouth shut. My well-intentioned reminder quenched some of their competitive back and forth teasing of what they’d make each other day if they win. They’d both end up in charge eventually.

“Then again,” I said as I dusted myself off once I climbed down the wall with them into Sunny Manor. “I could judge who was the best submissive at the end of two weeks, and then that girl gets to be in charge for TWO weeks at a time!”

The muddy canal in front of our community didn’t wash off the mud. It just made my skin wet and made me look even dirtier than before. It had the opposite effect on Stacy and Waverly. In the moonlight, they looked like chubby little woodland nymphs who were dripping wet.

“Why would the girl who does the best get submitting get to be in charge?” Waverly challenged my suggestion without dismissing it.

“The winner proved she doesn’t need as much submissive training because she was obviously very good at it,” I shrugged. I was just making this up as I went. I wanted to be the one to judge them!

“The credit for her being a good submissive also belongs to a good dominatrix. They supplied an environment of consistent structure and discipline!” Waverly said.

She had a point, and these girls knew much more about this lifestyle than I did. I told her I was just trying to think of a bet that would incentivize the girls to fully submit to each other and take it seriously.

“If we don’t, then Mom will have our ass!” Stacy shrugged that was already a given, and her sister agreed.

“On turnabout day, if we were to whine and drag our asses when our brothers give us an order, mom would just make us do the entire over until we get it right,” Waverly assured me.

It took us a while to jog to my house. I enjoyed listening to them talk about what they would make each other do once the game began.

“I want you collared and plugged all day tomorrow!” Stacy teased her big sister.

“I’m plugged most of the time anyway,” Waverly shrugged that it was no big deal if she wore a butt plug. It was sexy to see a girl be so open to that idea like it was nothing at all.

“Yeah, but this time it will because I told you and not just because you wanted to do it anyway!” Stacy teased her sister.

Once we got to my house, I was nervous my father might catch us here us trying to get back in. I was more nervous that my sister might catch us coming back in.

I wish I could say that I had thought a lot about what I’d do on Monday morning. My sister expected me to make a decision about one of the options she gave me. I had been distracted by pretty young girls and the promise of anal sex.

“We should hose you down before you go up there,” the girls pointed to our garden hose. I told them I had a bathroom with a shower in my room, and it would be fine.

“I’ve been hosing down my brothers since I was little. I promise it won’t take but a minute,” Waverly assured me and even walked over to the garden hose and bent over. I could see her pussy lips glistening in the light of our house.

“I am going to make my decision based on who fucks me the best. We could start in my shower?” I said with a cock-sure grin.

“Dirty, dirty boy!” Waverly put her hand on my chest and then touched my dick. “C’mon then,” she helped me climb my trellis.