Anal Etiquette Ch. 05: Politics as Usual

If you haven't already, be sure to check out the previous parts starting at chapter 00! Also if you like what you read check out Lordodie's series that started it all!

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Part 6: Silas, Shaine and Courtney in the Middle

"Call Shaine." I spoke into the phone mounted on the wall to the house. Ashley was upstairs still recovering from her time at the clinic. I had Courtney administering the anal cream the clinic had provided to ease my wife through her recovery period. She'd be suffering from anal fever through the weekend the doctor had said. Normally, it wouldn't be a problem for me after all Annie and Courtney would be around to administer to any and all needs that should arise. Annie had informed me after she got home from work that this weekend was the anal expo, her and some friends had been planning the trip for months.

"Silas! what's up little bro?" Shaine my oldest sister answered the phone, her curly brown trusses framed her pretty face. I could see perspiration on her forehead and she seemed short of breath.

"You working out?" I asked her, concerning her current condition.

"Only my ass." Shaine replied, the camera moved as she detached it from its resting place. The screen was a blur and then settled in front of her wide open snatch, sweat had matted the hair framing her wet slit. She was sitting on a mechanical bench, her ass nearly completely impaled on a knobby punishment plug that was spinning 180 degrees clockwise, then counter-clockwise. The camera was a blur again and then settled in its original position back in front of her face.

"Ashley has anal fever and Annie is out of town." I started explaining the reason for my call. "The only available pussy in the house is Courtney's." I continued.

"Isn't Katrina living with you?" Shaine asked, before letting out a little grunt and biting her lower lip.

"Not yet, she's moving in next week, which reminds me you're going to be expected to help with that." I told her.

"FUCK!" I didn't know if it was from the dildo being worked into my sister's guts or from finding out she has to help move Katrina. She sat there thinking, "Fine." She said after an awkwardly long pause.

"Why don't you come over and stay the weekend?" Finally getting to the reason for the call. "You're single now, probably not getting any action." I smiled to myself, getting in a jab at a sibling always feels good.

"More than you do." She shot back, but I could tell from the look on her face that it wasn't true, that or the plug had just opened up new ground in her backside, it was hard to tell.

"Well?" I was expecting a reply.

"Yeah, why not? I don't have plans for tonight." She came back. "Give me an hour."

"Ok, see you then." I hung up the phone.

"Who was that?" Courtney, my live-in maid was coming down the steps. She had on her maid's uniform. A quarter-cup corset pushing her substantial tits up and away from her chest, each rock hard nipple exposed. Her french maid's skirt was to short to totally cover her bare snatch from the front and exposed the retaining plug she had inserted looking from the rear. Her feet were sporting 4" black heels that shaped her already toned calves into works of art. She had a bare arm on the railing as she continued down the stairs.

"Shaine, she's coming over for the rest of the weekend." I informed her. Courtney stopped in her tracks and a look of concern came over her face. "Don't worry, she promised to go easy on you this time." I lied, Shaine and I never even discussed the thought.

"Umm, ok I guess." Courtney still looked nervous, probably recalling last time Shaine had made an appearance at our house. For whatever reason, Shaine had taken quite the liking to Courtney, of course to Shaine -being a notoriously infamous sadist, at least in town- liking someone meant dishing out some serious pain on their nether regions. Courtney arrived at the base of the staircase.

"You'll be fine." I told her to soothe her fears. "Now get over here and drop to your knees, I have to pee." Courtney was quickly at my feet swallowing the steady stream of urine I was supplying her greedy mouth. I finished, Courtney tucked my cock back in my pants and zipped them up for me. "You should go give yourself an enema, Shaine said she'd be here in an hour and knowing her she won't want to wait once she's here."

Courtney merely nodded her head in silent resignation that her asshole was about to be on the receiving end of the "Shaine train" as my sister often says. And headed -a little to slowly, for my tastes- to the bathroom to administer to her needy colon. The "Shaine train" was the only thing growing up I ever saw her get punished for, seriously punished anyway. Our mother had come home early from work one evening and caught her in the act. Shaine and Stephanie -my next oldest sister- had been ordered by Signy, our mother to make sure I was drained of cum by the time she got home. I had a date with Annie that night, one of our firsts and she didn't want me thinking about sex the whole time.

Stephanie was underneath me attempting to get yet another load out of me using her cunt. Shaine had gotten behind me standing up over the two of us, I felt the familiar feeling of my ass being opened up but things got serious real quick. Then I felt my asshole give way and something massive had entered my netherhole, then more and more.

I was putting up quite the fuss, and I remember Shaine just telling me to be quiet and take the "Shaine train" I moved myself around and looked in the mirror I could see Shaine had buried her entire foot and some of her calf into my ass. Not long after that mom walked in on us and jerked Shaine off the bed. As her foot popped past my ass ring I did shot one last round of cum into my other sister's front fuckport though, so I guess in that sense the "Shaine train" was a success. That was the one and only time I'd suffer through that little treatment of her's but Stephanie's husband has been on the receiving end of it many times from what Shaine tells me.

The hour passed, slowly when at last I heard a car pull into the drive way, minutes later the front door opened and my sister appeared wearing a long sun dress, there was a noticeable bulge sticking out from her belly visible even through the loose material of the dress. She was dragging behind her a huge piece of luggage, using both hands to pull it as she walked through the door and into the living room.

"I see you're ready." Shaine laughed as she took in my nude form occupying the couch as I watched TV.

"Why are you wearing a sun dress?" I asked her, I'd never seen her wear one before, and it looked odd. She just stopped dragging the luggage and without a word pulled it over her head and let it fall to the floor. She had been totally naked underneath with the exception of a strap-on harness, the strap-on itself was tucked between her legs secured there by a leather strap. She turned around so I could see her back and ass, the strap-on was being feed into her asshole. She squatted down, released the strap and the dildo slowly started to make its way out of her blown-out colon as she grunted and pushed.

I switched off the TV as my cock jumped to life. The dildo had wicked little triangles on it that was pulling and tearing at her sphincter as they came out. Soon the entire 15" was extracted and slapped the floor as the head came free. Wrapped around the head was something else though, a string that was going from the latex dong and running up into her asshole.

She reached down between her legs still in her squatting position and yanked on the string giving it a hard pull. A truly massive anal bead tore it's way from her intestine, it was easily the size of both of my clenched fists. "Ow, fuck." there was still more inside, another yank on the string and an identical bead appeared, as this one popped past her anal ring her asshole prolapsed momentarily as it tried to push itself out of her useless sphincter. "One more" Shaine declared, and gave another yank this time the bead came rushing out impacting the floor with a thud.

"Whew! That was rough." She declared standing up on shaky legs. Her asshole stayed gaping loosely even as she stood upright. She detached the string around the dildo her ass had just vacated and turned to face me. Shaine's eyes wandered down to my swollen penis. "Where's Courtney?" She asked me.

"That's a good question, actually. Last I saw her she was heading to the bathroom for a colon cleansing." With that Shaine quickly disappeared down the hallway, I heard some ruckus coming back towards me after only a few moments."

"No wait!" It was Courtney half-pleading, half-squealing, "I'm not done! honest!" The pleading was getting louder as from around the corner Shaine appeared in much the same position as she had been when she was dragging the luggage, only this time it was Courtney being drug. "Just five more minutes!"

"Found her!" Shaine seemed rather pleased with herself, at her discovery. "Get over there and straddle my brother's cock!" She ordered the maid.

With a look of defeat on her face, Courtney obeyed she stayed on her hands and knees and was slowly crawling towards the couch. "If you don't pick up the pace it's your ass that's going to be paying the price not mine." Shaine called after the girl. With the threat Courtney doubled her speed, if someone was able to run on all fours I imagine it would look something like her in that moment.

"That's better." Shaine said sauntering over to the couch. Courtney crawled up my frame, I held my cock into place as she lowered herself onto it. Shaine moved in behind the girl and was in the process of lubing up that wicked looking strap-on she still wore around her waist. Courtney was already beginning to sob as the anticipation built, she had flattened herself against my chest as best she could and was sticking her bottom out towards my sister despite knowing what was coming.

Shaine lined up the monster and pressed forward, I felt Courtney's pussy tighten up considerably around my member and I felt each pointy protrusion as they passed through the young maid's ass ring. Courtney's sobs turned into all out crying at this point. I started slow pumping Courtney's pussy unable to sit still any longer. As soon as her pussy started getting worked by my cock her cries died down and soon turned into moans of ecstasy. By the time Shaine bottomed out, Courtney was humping back against the both of us.

"Oh fuck yes!" Courtney was grinding her hips down onto both of the invading members. "Keep going! Right there!" Shaine was now working the length of the strap-on along Courtney's intestinal tract, pumping her hips back and forth rapidly. "Oh, shit! Oh shit! Fuuuuck! I'm cumming!" Courtney seized up, her pussy spasming around my dick. Shaine gave another couple pumps and buried the thing all the way in my young charges asshole and detached it from her harness.

"Stand up." Came Shaine's order. I almost did myself having a flashback to my teenage years. Courtney pried herself away from my cock and turned to face Shaine who gave the girl a smart slap across the right tit. Shaine hooked the dildo into place with a restraining strap and stepped back to admire her handy work. Instead of seeming happy though she looked disappointed. Shaine reached out caressing the girl's right breast, then slapped it hard, then again, then about a dozen more times. Finally, she seemed satisfied with her work and a smile came across her pretty face.

"Ok, teaching moment." Shaine declared. "Now most women think that once their asses have undergone a sufficient amount of training that they are of no use to a man's cock anymore." She eyed my own still erect cock while speaking, "This isn't the case, I'm going to show you have even the most well trained ass can still make a man happy. Shaine maneuvered herself over me, she placed both her feet onto my thighs and lowered her asshole onto my cock which didn't touch the sides of her colon going in. She reached down and started pushing my balls upwards until they too were inside her asshole. The combination of the two was close enough to sealing off her ass. "Now get on your knees in front of me. That's it between my legs. Just like that. Now slide your hand into my pussy. Oh, fuck yes! that's good." From what I could tell no lube was used during this process. Courtney's little hand provided some pressure against my cock but not much.

"Now slide your other hand in alongside the first." I'd been through this before, a family technique from way back. I remember Shaine teaching it to my other older sister Stephanie using me as a prop then too, Shaine having learned it from our mother. "God, yes!" Shaine hissed as another fist joined the one already present in her pussy. "Now feel around for the cock in my ass." She was giving instructions again. "Feel it?" I certainly felt it. "Good grab onto it and start jerking it like you're giving a handjob." I felt my cock get encircled within my sister's intestinal wall, It went from me not even noticing it was there to encasing my dick in no time at all.

I started squeezing my sister's right tit with one hand and reached down between her legs with the other and started encircling her little clit poking out from its hood with my fingers. Courtney was doing a great job jerking my cock through the thin layer of skin separating the two orifices. "Fuck yes, harder!" Shaine was giving orders again.

I stiffened up underneath her and started painting the inside of he colon white, wave after wave of orgasm hit me. Shaine started pushing outward with her ass and it soon prolapsed around my spasming cock and balls. I finished and moved out from under her. She remained laying back on the couch as Courtney started rotating her buried fists around in my sister's pussy. "Courtney, you're going to rip one of your fists out of me and then right after the first the other, understand?" Courtney nodded her head. "Now!" Shaine gave the order and Courtney did as she was told.

Shaine's pussy started immediately spasming its approval as the second balled fist was yanked free of it fleshy confines. Shaine's eyes rolled into the back of her head and Courtney did something I recognized as my wives' handy work, she started rapidly running her hand over the outside of Shaine's pussy prolonging the woman's orgasm. Shaine's asshole kept prolapsing with each of her pussy spasms, it looked as though both her pussy and ass were trying to make their escape.

Shaine always made for a fun weekend, and this one was going to no different.