More Deviltry

This is a continuation of Much Deviltry afoot. Please read that first.

All characters are of legal age.

More Deviltry

Jay and Sienna were living together now, I think Sienna didn't want to be alone. She also didn't want to be without Jay's 10-inch cock, which she could now take without being split wide open.

I had moved in with Marlena and we were fucking like rabbits every chance we had. She had also kept her promise of dilating my asshole for Jay. She desperately wanted to see me getting fucked by that young horse cock. I'll admit, I wanted it too. When I set a goal, I reach it. Marlena would warm up the stainless steel dilators and slowly work my ass over with them. She would get one in place and make me keep it in all day. She'd do this 4 or 5 times a week.

At first, it felt really weird wearing a butt plug to work, but like anything... you get used to it. I wore size #1 for a week and when it began to get easy to insert, she'd upgrade me to #2. I kept them in while we fucked and it felt great, making my orgasms much more powerful.

I told her, "Now that I'm on #2 dilator, we're gonna put the #1 in you. I want to see you take Jay in your ass as much as you want to see me."

She laughed and told me that she was already up to #4. She had made extra dilators and had been using them at the same time. Now I understand.

"That's why I practically fell into your asshole last time I fucked your butt!"

She laughed, "Yep, I've been an industrious little machinist. We have the same goal. I want to be impaled on that telephone pole too. I want to feel his cup of hot yogurt filling my intestines."

I nodded, "As long as I get to watch. Maybe we'll DP you. I'd love to feel his cock rubbing against mine through your pussy walls. I can see it now....monster cock in your ass, normal dicked me in your box.... and you screaming like a banshee. We may have to soundproof your bedroom."

Her eyes lit up at the thought of double penetration. She was gonna have a rough time sitting for a week after we got done with her. Poor Marlena.

We told Jay and Sienna about our little plan and she told us that she had ordered some dilators on Amazon. They'd be here in two days. She also loved the thought of two cocks fucking her at the same time. Jay had no problem with all of this. Sure, he was living his dream, sex anytime he wanted, a choice of two vaginas, three mouths, and three assholes. And no religious parents to pray the gay away. Things were looking up for him.

About six weeks after returning from Aruba, Jay's asshole parents found out where he was working and got his work email. If you have enough money, you can do almost anything. But, money can't buy common sense. The fools sent an e-mail stating that they were coming to his 'place of residence' to take him away from a life of sin and bring him back to god. The idiots even informed him when they'd be arriving!

I guess they expected Jay to just get in the car and go with them leaving us behind to wallow in despair and die in sin.

"Over my dead fucking body!", Marlena screamed when she heard the news. Marlena, having made lots of healthy donations to political and police children's charities, had connections with local law enforcement and was friendly with quite a few powerful politicians. She made a few calls and informed her 'friends' of the impending visit from Jay's parental morons. The police were waiting around the neighborhood in unmarked cruisers, they were also waiting in Sienna's bedroom. Marlena and I were also there for moral support. We never expected to be assaulted. I mean, these are religious people after all. Yeah, religious people.

The parents arrived in a Chevy Suburban and forced their way into Sienna's house at gunpoint, both parents had handguns. A big no-no in NYC. Carrying an unlicensed handgun buys you a mandatory 1-year jail term. The father hit me in the face with the butt of his handgun, cutting my face and knocking me down. I'll gladly take one for the team.

The officers stepped into the living room, guns and tasers drawn, and attempted to arrest the parents. Jay's mother kicked and punched an officer and was rewarded by being tased and handcuffed none too gently.

His father, Mr 'lack of common sense' tried to pull the cops off of his wife. Guess who else got tased? They were led away kicking and screaming about the wrath of god and the police would pay for this outrage, Blah blah blah... "My son is a sinner and you are condemning him to hell by arresting us! I'll make sure you all die for this! You will burn for eternity in the fires of hell!" Screamed the father.

Let's just add threatening police officers to the assault charges and carrying an unlicensed handgun in New York City. Oh, and let us not forget attempted kidnapping with intent to cross state lines. A few sundry charges would also be tacked on.

Rikers Island correctional facility, in NYC, is not a nice place. They're gonna find out the hard way. Needless to say, they fucked up....big time. They won't be bothering Jay for quite a while. New York City doesn't take well to people assaulting and threatening their officers. Both wound up as honored guests of Ossining prison, Singsing, for five years with the possibility of parole after two years. Guilty as charged your honor!

Jay took all of this much better than expected. In court, he told of the beatings and humiliations that were visited upon him in school and the threats from his loving parents. After the judge had passed sentence on them, Jay walked past his parents and simply said, "I hope the prisoners treat you better than you treated me. But...don't count on it." He turned and walked away to the sound of his mother bawling and his father threatening to wreak hellfire and damnation upon all those involved.

As for Jay, he received lots of support from the people at the factory and the LGBT community. They rallied outside the courthouse to cheer him on. Good non-judgemental folks.

Life got back to normal for us. We typically spent our weekends together at Marlena's home, fucking, sucking, riding a strapon or two, seeing who could get all of Jay's cock in their mouth without choking. I won that one. Yeah, me, the sort of straight guy with no blowjob experience! I put the two ladies to shame. I had gotten to the point where I could deep throat him, feeling his balls on my chin, and opening my throat so that he came in my esophagus.....right down the hatch. The girls couldn't handle his massive loads. Aww, too bad. I was finally better at something than they were, but it didn't seem to bother them. They usually jilled off watching me swallow him whole.

Sienna's and my enhanced anal therapy, or E.A.T, as Marlena called it, was progressing very nicely. Just not as quickly as Marlena's did. She was older and therefore a bit more of an easily opened back door than her younger friends. She was the first one to anally accept Jay's beast down to the root. It took two minutes of deep breathing and a few shots of tequila to do it, but she did it. After she had grown accustomed to his girth, she began to ride him like a pro. Her orgasms came like ocean waves on a stormy day, one right after the other...crashing into each other as they passed. The sounds that came from her were mostly unintelligible nonsense, growls, moans, screams, and primordial bellowing.

At one point, she rode him reverse cowgirl, so I lay her back on Jay's chest and slid my cock into her pussy amidst more screams and foul verbiage. The words, climax, and orgasm no longer had meaning. Her releases were now on the level of a volcanic eruption. She tore at the sheets and thrashed as if she was possessed. Jay's parents should see this. Hold that thought....

I came first and then Jay emptied himself in usual fashion into her gaping asshole. As Jay pulled out, the cum poured out of Marlena like a dam bursting, flooding the bed. My cum just sort of drooled out of her pussy, nothing to see here folks. I carried Marlena into the shower, lay her down on the padded bench, where she was gently washed by Sienna. Marlena's anus was still agape. It reminded me of the Brooklyn Battery tunnel.....wide open.

I couldn't wait to be on the receiving end of that cock, I used my dilators diligently. I even bought an inflatable butt plug to wear when I slept. Anything to be able to jump on that beautiful pole and feel it throbbing in my rectum. And all of this started with a very straight man and a simple strapon in Marlena's shower. She has taught me well, opened my mind, and asshole, to new and exciting experiences. I'm still learning new things about myself....all because of her.

Another weekend of sexual debauchery found us and I'm ready to be Jayed. We all showered as per usual but this time I didn't let anybody make Jay cum in the shower. Instead, we all took turns sucking him and keeping him on edge. We'd get him close to blowing a load and then stop. I wanted as much cum as I could get when he fucks my ass tonight.

Sienna gave me a few brown soap enemas so there wouldn't be any nasty surprises when Jay pulls out. I sat on the toilet for almost thirty minutes, and after three enemas, I was squirting crystal clear water out of my asshole.

It was time.

As I lay on my side, Marlena greased my rear end, thoroughly.

She squirted lube inside and out. This stuff was almost as thick as Crisco and as slimy as an eel. She made me lay face down with a pillow under my pelvis, lifting my ass a bit.

Sienna lubed Jay's horse cock and guided him to my relaxed pucker. I felt him start to press his cock into my asshole, he was as hard as stone. I took a deep breath and let it out slowly...slowly....slowww POP! His cock head had easily penetrated my defenses and was easily working its way toward my brain, or so it felt. With as much dilation as I'd had the previous weeks, I was still being stretched beyond belief, I whimpered piteously.

His slow advance was worse than the stretching though. I wanted it in! "Stop fucking teasing me, Jay!" The frustration was evident in my voice. Unable to stand it anymore, I pushed my ass back onto him and he slid in right up to his balls. The women let out a simultaneous war-whoop, high-fived each other, and did a little victory dance on the bed.

Jay grabbed my hips and pulled me up into a doggy position and started thrusting deeply but was still too slow for my needs. "Come on goddamnit! Fuck me! All the way in, hard!"

Jay can be a bit slow on the uptake at times, but he finally got the hint. He started slamming into me, driving all ten beautiful inches in with ferocious thrusts. My eyes rolled back in my head and my sight started to dim.

"Breath you big yutz! Stop holding your breath! You're gonna pass out!", Sienna screamed.

I drew a few deep breaths and the world came back into focus. Now it was my turn. I began thrusting back to meet his advances thus driving him deeper than his ten inches. His balls were crashing into mine. I'm sure that this would be painful in everyday life, but this was most definitely not everyday life.

This young man can fuck! He pounded my poor asshole for five minutes, till I was numb. I made him pull out momentarily so we could change position. As he pulled out, I felt something I've never experienced before. A breeze was blowing into my gaping hole, it was cold. It felt like a chill mountain wind blowing through a cave.

Jay pushed my knees back as I lay on my back, the pillows under my ass lifting my hole to his cock level. He poured more lube on me and slowly buried his sword to the hilt, deep inside my rectum. Now, every time he pushed into me, he'd hit my prostate causing me to squirt cum. Sienna and Marlena got my cock in a dual-mouth kiss. They sucked every drop that Jay forced out of me.

I had hold of his ass cheeks and was doing my best to pull his entire body into my asshole, I wanted him in...balls and all. This was the most incredible thing on earth.

I could tell that he was gonna blow sky-high soon, the look on his face said it all, "I'm cuuuuuummmmmiiiiinnngggggg! Ohhhhh myyyfuckiiiiingggg godddddddddd, I'm cuuuuuuummmmiiinnnnngggg!" He bellowed so loudly that the neighbors had to have heard it.

His cock pulsed and throbbed in my colon, sending his hi-test yogurt cum deep into me. Five, six pulses, and he still wasn't done! He fell back a bit and his cock unintentionally flopped out. He was still shooting thick ropes of cum that hit the girls on the sides of their faces because they were sucking me off.

My poor asshole was talking to me again... 'was it worth it buddy?'

Fuck yeah! It was soooo worth it. I could now feel his hot cream pouring from my sparkling clean asshole and I told him to plug the dam with his semi-limp cock. He managed to stuff himself into my war wound, thus stopping the Niagra-like flow, as the girls scooped up his cum and rubbed it over all of us. We were covered in Jaygoo. This boy really should be in porn.

Sweet Sienna brought a warm wet washcloth to plug the hole in my body and held it there whilst I crawled on hands and knees to the shower. The ladies helped me to stand and washed me as the cum poured out and ran down my leg, no poop, just an endless stream of atheist semen.

Praise the lord and pass me something to plug my ass with.

When I had pushed everything out of me, I tried and miserably failed to pucker my uncooperative sphincter. I could feel the cool room air going in and out with my breathing. I bet that if you put a flashlight in my mouth, you would see the beam shining out of my asshole. 'Oh please, don't let me spend the rest of my life with a tunnel for an asshole, close up damnit!' I didn't want to have to explain something like that to my doctor.

My hole finally began to go back to normal after ten long minutes. I was saved....I wouldn't need to wear a diaper! Wooooohooooo!

I was finally able to hobble back to the bed where Jay was waiting with celebratory champagne.

He had a proud look on his face, "I know how hard you worked just to be able to take me in your ass, so I bought this bottle of Roederer 242 to celebrate with.

Marlena, being a connoisseur of fine wine, took the bottle, approved of the vintage, and expertly opened it.

The bottle didn't pop, it sighed. She said, "A properly opened bottle of champagne should make a sound like the sigh of a satisfied woman." "A toast! Good health to all of us, and may our assholes never need lemon juice to tighten up after being Jayed! Congratulations on being man fucked by Jay."

I laughed, and in my best Fozzie Bear voice said, "Thank you, thank you, thank you...and thank yoooooo! I would stand and bow, but I think my liver might fall out of my asshole if I did." Guffaws all around.

We drank our champagne in silence for a few minutes when Jay looked like he'd had a eureka moment.

"This might sound cruel, but I want some payback. We need to make a video of all of us having sex together, and send it to my parents when they get out of prison. That will put a torpedo in my father's stern. Speaking of getting torpedoed in the rear, I wonder if the stories of prison rape are true? Do you think that my racist father is getting it in the ass from a big dark-skinned, monster-cocked gentleman? I sort of hope he is. I hope he's surrounded by the people that he hates. Don't you think it's odd that such a religious man could have so much racial hate in him? Yet he preaches 'Love thy neighbor!' I guess that only applies to neighbors that are white and uptight like him."

What's even more shocking is that he doesn't know that my mother.... my holier than thou bible-waving, PRAISE JAYSUS! mother was getting fucked by her black chauffeur, Reuben. She would go to the guest house when my father went out preaching, suck Reuben off, and then get her brains fucked out for four hours by a very large black cock. She was also fucking Alonso, the pool man. Sometimes Reuben and Alonso would double team her. I could hear her screaming from my bedroom."

He continued, "My father never figured out why his wife was always in such a good mood when he got home. She often told him that Jesus was in her soul, making her happy. More like Reuben's big black cock was in her hole, making her happy."

The southern Italian blood in me pumped faster at the thought of getting back at those two miserable creeps for all the torture that they visited upon him since childhood.

"Jay, I have a plan. We can make that video and have a prison officer play it for your parents. We'll each wear masks and introduce ourselves by name. They'll certainly recognize you by your voice, and I'm sure your parents saw your cock when you were growing up...they'll recognize that too. We need the masks just in case the video gets out. Nobody can identify anything....except maybe the beast that lives in your pants."

Jay told us, "Oh fuck! I just remembered something else. My mother used to sit at the tubside and watch me as I bathed, making sure that I was 'clean enough for the holy spirit'. Now I realize why she sat there and why she liked the chauffeur and Alonso so much. It's because my father had a three-inch skinny worm for a penis...you wouldn't call it a cock or even a dick. My mother was perving on me! She never touched me, but she always watched as I washed my cock and she'd get all hot and bothered if it was erect. That scranky old whore wanted my cock, but she was probably worried that she'd be excommunicated from her precious church and shunned by elite society if they knew she was getting dicked down by her son. It's probably much less damning to be caught screwing the black chauffeur or the Italian pool guy. Good god fearin people! HAAA! What a pair of fucking hypocrites they are! Let's make this movie! Yeeeehaaaawww!" He jumped up pumping his fist in the air.

Jay was all fired up. I don't recall seeing him this happy since he first fucked Sienna.

When I was finally able to sit down, Jay and I wrote out a sort of script to follow for the movie. I had access to professional video cameras at work, I'm sure that Marlena could get the CEO to lend them to us. Because Marlena and I were big fans of Star Wars, we opted for a Star Wars-themed video. Ya gotta love Amazon. Everything we needed was just a click and prime delivery away. Click click click, and we had a Darth Vader helmet, Yoda, C-3PO, and a Chewbacca headpiece. This was gonna make Star Wars history, a Rule 34 type of thing.

With Jay's help, I had set up three video cameras throughout the room and one pointing down at the bed. Jay, the genius engineering student, made a light fixture/camera mount for the ceiling shot. Everything was fed to Marlena's computer for recording.

The plan was to introduce ourselves by our first name while wearing the costume helmets and the white hotel robes from Aruba. (And no, we didn't steal them...Marlena put them on our hotel tab. We might be sexual deviant weirdos, but we're not thieves.) After introductions, we would remove our robes and have a lightsaber fight with some of the purple-lighted dildos from Marlena's collection.

The cast is as follows.

Marlena: Darth Vader

Sienna: C-3PO

Dave(me): Yoda. I do a great Yoda impression.

And the Star of our movie, Jay: Chewbacca

Making movies isn't as easy as one would think. There's lighting to be considered, sound quality, proper camera angles, wires and tripods to trip over, and tons of editing.

The cast was ready, the stage, set. Lights, camera, action!

The four of us, each wearing our mask and hotel robe, walked out holding hands. Facing one of the cameras, we introduced ourselves as the character we represented, not our real names. Chewbacca Said one of his two English lines, "Mother and Father, this video is for you from your loving sinner son formerly known as Jebediah. I hope you're having a wonderful time in prison. Though I doubt it. Oh, by the way, I'm changing my first and last names. I won't be associated with hypocritical filth like you anymore."