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Breaking Billy

"A dildo up a man’s butt won’t break him unless it’s done right."

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Author's Notes

"I think this story stands on its own, but if you haven’t already, take a peek at “Taming Billy” to see what came before."

“Don’t be stupid, Billy. There ain’t nothing gay about this. Do I in any way look like a man to you? At all?”

“Phfft! Are you kidding me?” Billy leered first at his naked sister-in-law’s big ol’ tits, tits that not long ago had been taking turns in his mouth. Vera had long hair like a woman should, a face made up just on the good-girl side of slutty, and a round ass too big and too small to make fun of.

His stare lingered at the cum dripping out of her furry cunt despite the hovering, menacing vein-laden strap-on nodding approvingly at him. He didn’t dare mention that, obviously.

“I’m sorry, Baby.” Vera played with his slicky, recently re-drained cock, and locked her eyes onto his long enough to make him uneasy. “I should have known you were making a joke. You’re so secure, not like your brother. Too bad your cock isn’t as nice as his.” Billy, satisfied that she understood he was all man, had long ago stopped protesting whenever she compared his cock with Jimmy’s.

“Lie back,” Vera instructed as she snapped on a latex glove and squirted out some lube. “You like fucking Jeanie’s ass, I bet.”

“Sure, yeah.” Billy sucked his next breath through his teeth when she slipped her finger in. “She likes it too—a lot.” He shuddered when she massaged his prostate—not that he knew that’s what it was.

“I don’t doubt that.” Vera flopped his cock with her hand while prepping him for a second finger. “She’s got a cute ass. It’s like a boy’s ass, isn’t it? Like an ass you used to see in the showers, I bet, after those Varsity games?”

Billy liked the way she was man-handling his cock and he liked what she was doing with the second finger. “It ain’t like that at all,” he argued, but the image got stuck in his head. “You and Jimmy do this butt thing too, right?” he asked again, just to be sure.

“What your brother and I do in the privacy of our bedroom ain’t none of your business.”

Something about what Vera said didn’t sit right with Billy, but he couldn’t quite work it out in his head. He shifted under her pumping fist so that his nuts weren’t getting battered so much, and his cock got harder as he thought about fucking his wife’s ass. His cock got harder as he thought about his ass clamping around his sister-in-law’s fingers. His cock got harder with the unbidden visions of showering young men.

“Fuck, no!”

“Something wrong, Baby?”

“How come you can ask me about me and Jeanie, but you said you and Jimmy’s sex life ain’t none of my business?”

“My fingers up your ass makes it my business, dumbass.” Vera climbed down and discarded the glove. “Okay, off the bed! This is exciting, isn’t it?” She gazed into Billy’s eyes with as much sincerity as she could fake. “Baby, I want to make you as comfortable as I possibly can. We’ll do this exactly the way you do Jeanie. Get down on your knees and suck my cock.”

“I ain’t…”

“Baby, don’t be angry, no-no-no. It needs your spit, that’s all, just like when Jeanie sucks your cock before you lube that bad boy up. And, Baby, this one is rubber, so it needs a lot more spit before the lube will work right.”

“I can’t…”

“Well, Baby, I can’t suck it myself, as much as my big macho man would like to see me try. Yeah?” Vera held her dildo and had Billy squat in front of her. “Oh, Baby, that is so hot, watching you from up here with your cheeks sucked in and all. No wonder you like to watch when I do it.”

When Billy said that it was wet enough, Vera squirted some lube onto his palm and told him to stroke it. “I’ll bet it’s been a long time since a lady-killer like you has had a cock in his hand. Baby, I wish I could feel it for you.”

“Is that enough?”

“Bend over, Sexy. You’ll be the first to know.” Vera shoved him over by the shoulders, caressed his hairy butt, and positioned her rubber phallus. “Patience, Baby. I know that you’ve wanted this for a long time.”

“I never said…”

“It’s okay, Baby, we’re family.”

“Yeah, but…”

“Hush, now. Don’t make me hurt you.” Billy winced and clenched. Vera sang nonsense to him and hummed, pet and patted him until he relaxed. She pulled his cheeks apart and told him what a pretty pucker he had before coaxing it open. Vera penetrated him slowly, smoothly, two bits in and one bit back until her cock popped and bottomed out.

“Damn…”

“You were right, Baby.” Vera fucked him with increasingly stronger thrusts, knocking him off balance until he, and his re-inflating cock, were firmly against the mattress. “You always told Jeanie how much she liked getting fucked in the ass, and you were right, weren’t you?”

“Damn…”

Vera chuckled from behind, making sure that every one of her thrusts forced him to hump the mattress in turn. “Baby, I wish I could feel what it's like to be in you. Are you hard again, yet? I can’t wait for my turn.”

Billy was so lost in his ass-fucking-mattress-humping bliss that he hadn’t thought about getting his turn in her ass until it was too late—Vera had made sure it was too late—and, right after she gave him a solid spank, he lost his third load of the day between his gut and the sheets.

“I ain’t waiting anymore,” Vera said when she withdrew. She strapped off her strap-on and bent over the bed at his side. “Baby, watching you made me want this so bad!”

“Baby?” She nudged him shoulder-to-shoulder and called him by name. “Don’t tease me, Baby.” She pretended to be shocked and dismayed when he rolled away from her, exposing a cock that had gone even softer than she had last seen it. “Baby. I don’t understand. Why ain’t you hard?” She had a break in her voice, and she quivered her lip. “You said you like it.”

Billy sputtered, trying to come up with a plausible excuse.

“Billy?” Vera scooped her fingers through the puddle he left on the sheets. “William? You came? You came? You selfish prick!”

“Vera, look…”

“No! I ain’t got the patience for your excuses.” Vera slipped into her role of a neglected, red-faced, teary-eyed woman. “I sucked you real good and I even swallowed, and then I let you fuck me and let you cum inside, and I didn’t say a word when I didn’t cum because you promised!”

Her brother-in-law hung his head, and Vera angrily paced back and forth like a wounded animal. “'Jeanie likes it in the ass,’ you said. ‘Please fuck my ass,’ you begged. You did, you begged, and you said ‘please’ and you never say ‘please.’ Then you promised to make me cum with your prick in my ass. You promised!” Vera wiped her nose with her arm and sat next to him. “I could hit you! I’ll make Jim hit you!”

Billy didn’t remember the events quite the way she said, but figured this wasn’t the time to argue about it. “I didn’t mean to, honest.” He put his arm around her and comforted her the best he knew how while she quietly sobbed on his shoulder. Three times was pushing it as it was, and he knew he wouldn’t be able to get it up again anytime soon, but he suggested that maybe they could try in a little while.

“No, that’s okay.” She sniffed and looked down at her hands folded in her lap. “I know you don’t like me, Billy, and you’re just using me, but I kind of hoped, you know, playing with our butts, you know…”

“Yeah, I know.” Billy was surprised at himself for not growing another boner because crying women used to be such a huge turn-on. “Honestly, I never saw what Jimmy saw in you because you were always kind of bitch, but you were always a looker and always a good fuck. I mean it. A great fuck.”

Vera rolled her eyes and hoped that Billy hadn’t seen it. “Thank you,” she said softly and tried not to laugh. They sat in silence a moment, and then Vera abruptly stood. “I need to see your wife.”

Billy objected, of course, and his unimaginative outcries grew louder the longer Vera dismissed him. She slipped a dress over her nude frame, made a show of adjusting the girls, and fluffed her hair. “Jeanie and I need to talk,” she said and slyly retrieved a set of handcuffs from her nightstand. After two rapid click-clicks, Billy was trapped. “Stay!” she commanded. “We’ll be right back. You should think of something to tell Jim in case he comes home early.”

She slipped her sneakers on and ran out, ignoring his demands and pleas. Jeanie and Billy’s house was only a short jog down the street, and when Vera burst in, she giddily kissed her sister-in-law. “Better!” she said. “Kiss me better,” and the two made out until Jeanie managed to push her back.

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“I thought Billy was with you.”

“He is. He was. Baby, I fucked him in the ass. He’s breaking.” Vera caught her up during the walk back and told her to follow her lead.

Billy couldn’t reach the nightstand drawer for a key and couldn’t shake himself out of the cuffs. He fantasized about the lessons he would give Vera and shouted for her over and over until she and Jeanie walked into the room. “Get these off of me, you bitch! Jeanie, baby, this isn’t what it looks like. It’s all Vera’s fault!”

“I know, Billy,” his wife said, cupping his cheek. “I used to think everything was my fault, and it is, but it’s her fault, too, and mostly yours.” When Billy rattled his chains, Jeanie jumped and pleaded with him not to be angry at her.

Vera waved Jeanie over and embraced her. She told her sister-in-law not to look at her husband before they kissed, and that time, Jeanie didn’t have to be instructed to do better. She put all her fear and misgiving into the kiss and held on to the other woman for dearest life.

Billy’s jaws flapped silently as he gawked. He didn’t know what to think about Jeanie kissing a girl, much less that girl.

“Jeanie, love, we must confess ourselves to your husband. Shall I start?” Jeanie quickly nodded. “Billy, I am embarrassed to say that your beautiful wife has seduced me.”

“I, I ain’t sure I’d put it that way.” Jeanie, with eyes wide, couldn’t figure out where Vera was going with this.

“No, Jeanie, do not try to protect me. I succumbed to your allure just as your husband must have. Billy, Jeanie sought me out when you became violent with her—my words, not hers! How she unearthed my hidden lesbian yearnings, I’ll never know.”

Vera turned away and thought, I could have been an actress.

“Baby, you’re a lez?”

“Baby, no, I…” Jeanie stuttered, unable to deny anything under Vera’s glare. “I ain’t sure what to say.”

“You gotta fuck me, Billy,” Vera told him, stripping off her dress. “You gotta be a man and fuck your brother’s wife in front of your lez wife.” Billy jerked his impotent, floppy dick, knowing full well that he couldn’t rise to the occasion, and Jeanie felt bad for him when Vera made fun of him. “You can get a boner when I’m fucking you in the ass, but you can’t get one when a naked woman wants you in her cunt?”

“Jeanie, it’s not like that. Vera, that ain’t right. You ain’t being fair.”

“Oh, I’m fair, alright.” Vera pulled Jeanie’s frilly T-shirt over her head. “I’m more than fair.” Jeanie’s denim skirt was tossed aside next, as were her powder blue panties, leaving her only in her matching frilly push-up bra.

“Don’t cover up, girl,” Vera said, stroking Jeanie’s hair. “Ain’t nothing we ain’t all seen before. Billy, what do you think? Are girls prettier naked, or boys?” Hand-in-hand, Vera brought Billy's bottomless wife just out of his reach. “You ain’t hard again yet? Damn.”

Vera rubbed her pussy, teasing her pubes and teasing her slit. “I’m horny, Billy. You made me so horny. I need to cum so bad, Billy, and you didn’t do it for me.” She kissed Jeanie on the shoulder and rested her head there. “That means it’s Jeanie’s job. It falls on the man’s woman to finish what he can’t.”

Billy jerked on his flaccid cock fast enough to start a fire if he had had any wood at all. “Jeanie,” he meekly called when Vera put her hands on his wife’s shoulders.

“I don’t know that I can,” Jeanie whispered when Vera applied a little pressure. “I ain’t never. You know I ain’t never…” Her eyes said, you know. She shook a little as she unlocked her knees.

“I believe in you, Baby,” Vera whispered back. “Billy won’t believe that he turned you lez if you don’t.” Jeanie sank to her knees, just the way Billy would make her, and hesitantly licked her first-ever pussy. “Jeanie, that feels so good. I didn’t think it could! I ain’t never. You know I ain’t never.”

With Vera’s moans of encouragement, with the encouraging grip Vera had on her hair, with Billy’s encouraging groans, Jeanie used her tongue and mouth to please her sister-in-law the way she wished Billy would eat her. She licked her lips, and her lips, inside and around, coating her face with Vera’s excitement.

“Baby, yes! Can you taste your man in me? Suck the man out of me!” Vera’s theatrics might have been over the top, but her orgasm was real and real good. She shuddered and giggled, and she looked straight at Billy when she said, “That was better than any man, Jeanie—any man!” His shoulders and head slumped, and he gave up on his manhood.

Vera passionately kissed Jeanie and thanked her, barely taking out her tongue. “My cunt tastes so good in your mouth,” Vera said over and over again.

Jeanie sat on the floor in shock, painting her bald pussy with its juices and wishing she could apologize to her husband.

“I thought two women together was supposed to turn a man on, but you’re soft, Billy. That says something about a man.” Vera kissed Jeanie and told her to stay put and she’d be right back.

“Jeanie!” Billy softly called, looking out for Vera. “Get me out of these handcuffs. Let’s go home, and I promise I’ll treat you right from now on.”

“I don’t know if I should. I mean, she told me to stay.”

Vera returned with a laundry basket full of stuff before Billy had a chance to convince her. “Here we go!” she said. “We’re doing this for you, Billy, so you’d better appreciate it.”

She plucked Jeanie’s bra away and wound several turns of plastic wrap around her, flattening her already modest rack. She gave her one of Jim’s old T-shirts and held up two strap-ons. “Double-ended or not, for you? ‘Not,’ I think.” She stood back when she was done and admired the small phallus bobbing above her pussy.

“That’s good, but we’re not quite there.” She warned Jeanie to stand very still. “These are very sharp,” she said and cut Jeanie’s hair very, very short, and then parted it to one side. She wiped off Jeanie’s make-up and declared her to be a very handsome young man. “Isn’t she, Billy? Isn’t your wife a good-looking young man?”

Vera wrapped up her own much larger breasts the best she could and covered up with a button-down flannel shirt. She hid her hair under a baseball cap and stuffed in one end of her double strap-on. “There,” she said in her best false basso voice. “No chicks here. It’s just us guys.”

“Fuck,” Billy said under his breath.

“Front or back, Jeanie? I mean, Gene. C’mon, Billy, on the bed. Up! That’s a good boy, on your hands and knees. You can have the back, Gene. You can call me Vern. Billy, open your mouth so you can get Gene’s cock wet. Don’t be shy. It’s not like you’ve never had a cock in your mouth before.”

“Billy?”

“Uh-uh, no talking with your mouth full!” Vera pushed on Jeanie’s butt and shoved her dildo down Billy’s throat. She let him gag on it a while before letting him cough it out. “I’m sorry. Were you uncomfortable? Were you gagging? You were? I apologize for that, and promise never to do that again.” She slapped her cock on his face and said, “See how that works?”

Vera replaced Jeanie’s cock with hers and began fucking Billy’s face. She tossed the lube at Jeanie and told her to use as much or as little as she thought best. “You can fuck him the way he fucked you.”

Jeanie liberally lubed her dildo and his ass hole, and kissed him on the back before penetrating him. He moaned around Vera’s cock as his skinny wife man-fucked him, thankful for the smaller cock and gentler thrusts.

“You ain’t hard yet? Boy, you don’t like girls, and you don’t like boys. You got more problems than I want to deal with.” Vera withdrew from his drooling trap and positioned herself behind Jeanie. She only needed a few dry thrusts before syncing up with Jeanie’s hips and sinking between Jeanie’s sopping lips.

“Oh, God!” Jeanie screamed. “I can feel it in my cunt and I can feel it in my cock! This is fucking amazing!” Like sweaty dominoes, one collapsed after the other.

Billy curled up into a ball but couldn’t avoid Vera’s examination. “I’m so, so sorry for you, Billy. Jeanie, come look. Look.”

“Vera, can me and Billy just go home?”

Vera sliced away Jeanie’s bindings and said, “Oh, Baby, I’m so, so sorry, but, no. You and I are spending the night together at your house, but Billy has to stay here. Both of you get dressed now, okay? Billy, be sure to make the bed before Jim gets home. You can sleep on the couch. I’d tell you no jerking off on my couch, but I don’t think that will be a problem. It’s nice to see you’re not getting angry about these things anymore.”

~~~

Jim came home to his brother sitting on the couch. “Vera here?”

Billy silently shook his head.

“You get kicked out?”

Billy nodded.

“Vera over at your place?” Jim called out from the kitchen.

“Yeah.”

“Dude,” Jim said, tossing his brother a beer. “You are so fucked!”

Published 
Written by dronette56
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Comments

This is so fun! Vera is amazing and yes, Billy is so fucked. Intense way of transforming Jeanie … I’m intrigued to see where that goes.

I'm glad you're enjoying it!

That was fun 👏

Vera is hot and dangerous. Curious why she had to cut Jeanie’s hair where she got away with tucking hers under a baseball cap. But otherwise I’m curious if Jim gets involved to help Jeanie experience more bliss.

I wanted Vera to be both of those things—I'm glad it came across. She cut Jeanie's hair simply because she could. She had control over her, and that was one way she used that control to control Billy.

I love this story and the one before. Such a tantalizing exploration of a couple of great themes! I love how Vera manipulates the situation with both Billy and Jeanie and how she can use sex as a weapon. It makes her a very interesting character! I don’t know if you have plans for another “Billy is so Fucked” story, but my imagination is wondering what twist it would have.

I'm glad you liked it! I hadn't planned on a follow-up to Taming Billy, then an idea popped into my head. Now, I have a couple of other ideas, so let's see if I can make anything of them.

Oh my - so fucked... 🙄

Tee-hee—so true.

Vera is a badass. 😈

I wouldn't dare to argue that point!

This story was fun to read, poor Billy doesn't have a chance with Vera around! Great story telling!

No, he doesn't. Thank you!

Maybe Billy will get hard with Jim’s cock in his ass??? Since the wifes are having fun down the street!!!

That would make for an interesting twist and something Vera might want to arrange.

I like that plot!!! Vera is just the bitch to arrange that!!

I don't think Jim has ANY idea... hahaha

I left Jim in the background, that's for sure. I didn't know whether he was clueless or already whipped.

Yet again, Vera proves she's always two steps ahead!

Well, _somebody_ needs to know what needs doin'!