Late Night Truth or Dare Ch. 08

He started to pause, get everyone's attention, and make the announcement that he and Dee had planned, but realized what Dee knew immediately: It could wait. They had wanted to tell everyone that Dee was off birth control, and that she'd be ovulating the next week, but there was time, plus, with her "whoever the lucky guy is" attitude, Mark knew it didn't matter. Everyone here was fucking with the intention of impregnating themselves of someone else, so what was one more child from whoever got lucky. If it wasn't Mark, he was sure he'd get a shot with one of the other women. The thought was crazy to him, but the more it sunk in the more he realized that he was going to love being a party of this large, crazy, fucking family.

***

"Hey, everyone," Jennifer chimed her glass as she stood. "I just wanted to congratulate everyone. Some of you just graduated, some of you are pregnant and just graduated, and some of you are just, well, do I need a reason to cheers any of you? Anyway, I really just wanted to ask something. I know we've all done some crazy shit, and are still doing it, but there's one thing I haven't done yet, and now that Mark is here, I want to try this."

"What is it, mom?" Sarah yelled out from the other end of the table. "Just ask, I'm sure everyone will be into it."

"Well, I want to have all three holes filled at the same time," Jennifer looked around the table, stopping on Bobby, Ian, and Mark as she made the circle. "What'ya say boys? Want to give this old woman her wish?"

"We'd love to, right guys?" Ian said, already moving toward Jennifer, his cock growing as he walked.

"I'm in," Bobby joined his mom and brother.

"Me too," Mark said. "I just have one question, who get's what hole?"

***

Jennifer had thought hard about how she wanted to do this. She'd never even been double penetrated, which is what she was going to ask for before Mark showed up, and she was nervous she wouldn't be able to service the three guys at once. Originally, she'd envisioned sitting on Ian's lap, while he sat in a chair, with his cock up her ass. He wasn't as thick as Bobby, and she thought he deserved to have her butt more than anyone. That would allow Bobby to fuck her cunt while either straddling, or standing between, Ian's legs. This was all good, but it put her head a little too high for Mark to fuck her face without standing on something. Instead, she deciding she'd put Bobby on his back, with her on top, leaning forward, giving Ian access to fuck her ass while he kneeled behind her. They would have to work out a rhythm to make sure their thrusts didn't fight against each others, but it would put her in perfect position to turn her head and suck off Mark. After a coordination meeting, they invited everyone to watch, wanting to put on a show while Jennifer was used by the three young men.

"All right, boys. You know the drill. I want you to all shoot together, if at all possible, and no one get's to cum until I do," Jennifer raised her arms above her head, stretching in anticipation of her body being brutalized by three young cocks.

"Yes, mother. We know the drill," Bobby jested as he lay back, his hard cock rising above him as he held it in place for his mother to impale herself on him.

Jennifer straddled her son, running her soaked cunt over his head before settling on him. She was always surprised by his girth, as his father lacked any at all. She wiggled her hips and she sank lower, adjusting forward as she presented her asshole to Ian. She kissed Bobby, teasing his tongue, as Ian lubed up her sphincter. He'd fucked her in the ass many times, but never with anything bigger than a small vibrator in her pussy. This was going to be tight, and she made sure he added enough lubrication.

"Take it slow," Jennifer broke from her kiss with her son. "This isn't like the other times. It's going to be tight as shit in there. Bobby's already filling me up in the other hole."

"I've got it," Ian said, slowly popping his tip inside Jennifer, "but yes, you're fucking tight as shit. I think I can feel Bobby's cock through the walls of your ass."

Bobby started to slowly thrust, learning to time his and Ian's thrusts. Ian was in charge, not only because he was in the more delicate hole, but because he was in better position to drive his cock with confidence. Bobby, on his back and lacking the ability to move Jennifer, could only do so much, but with the pressure Jennifer was feeling in both holes, he didn't need to.

"Oh god, you two feel amazing. I can't believe we haven't done this until now," Jennifer moaned. "Can you feel each other?"

"Oh, yes," Ian moaned. "Fuck, your ass is tight like this."

"I feel him. Just sliding along my cock." Bobby said. "It's fucking weird, feeling another guys cock like that, but I have to say, it feels fucking amazing. You better cum fast, because this is going to be hard to hold off for."

"Don't worry son, I' not going to last long. Just keep filling me up," Jennifer rolled her head as waves of pleasure swept through her. "Speaking of filling me up. Mark, get over here and stick your cock in my mouth."

"Yes, ma'am," Mark obeyed and pressed his dick against Jennifer's lips, waiting for them to open before pushing deeper, achieving her dream of being filled in all three holes at the same time.

The boys cycled through their thrusts, making sure to take their time and not rush. Any deviation of their rhythm threw everyone off and they had to reset. Despite the methodical method they were implementing they were all approaching orgasm. The excitement of the situation, the pressure on their cocks, and the encouragement of the onlookers drove all of them closer to orgasm, but each held off, trying to prolong the session in accordance with Jennifer's demands.

"Pinch her nipple, Mark. She loves that," Ian instructed. "Sarah, come over here. See if you can reach her clit. Colleen, get the other nipple. I want to give her the best orgasm we can. Stimulate everything. She deserves to feel the love from all of us.

Each girl did as she was told, with the others filling in behind the guys. Candace ran her hands over Ian's chest, pressing her breasts against his back. Dee did the same to Mark, but she also reached down and cupped his balls as Jennifer engulfed his cock. Ashley leaned over and kissed Bobby, sneaking her head next to Jennifer's. They all engaged in their own way, and drove the original foursome toward their goal of massive orgasm.

Jennifer was the first to tip the scales of her pleasure, plunging into the depths of bliss as her body was rocked by a massive orgasm. She moaned, vibrating her mouth on Marks cock, sending him into a climax right after hers. He shot into her mouth as she tried to swallow, hampered by her body shuddering with pleasure.

"Oh, oh, oh!" Mark moaned, thrusting into Jennifer's mouth as Dee cupped his balls, squeezing tight as she knew he liked.

She managed to contain the first stream, but the subsequent explosions of his dick oozed out of her mouth and ran down her cheek as Ian launched his orgasm next. His cock spasmed and filled her asshole with his cum.

"I'm cumming!" Ian shouted, louder than he needed. "Oh God, this is amazing."

The sensation of his cock throbbing through Jennifer's thin flesh sent Bobby over the edge next. His cock jerked sharply and pumped his semen into his mom.

"Me too, bro. Me too," Bobby added as he grabbed Jennifer's hips and pumped into her from below.

She was not only being fucked in all three holes, but the boys were filling each of them with their cum. All at the same time. Just as she'd dreamed.

"Oh, fuck, boys, this is fucking amazing. Keep going, don't stop, I'm not fucking done yet," Jennifer said after Marks cock popped from her mouth, continuing to shot several more shots of sperm across her face. "Fill me up. Cover me with cum. Use me like a fucking whore, boys."

"Yes, mom," all three boys responded in unison.

They kept going, milking their orgasms for as long as they could, trying to prolong hers as they worked. Eventually, Jennifer collapsed, lowering her weight onto her son's body, pinning him to the floor as his cock began to shrink inside her. Ian reluctantly pulled his cock from Jennifer's ass, allowing a stream of cum to leak from her, dripping down over Bobby's balls, as he sat back on his knees before listing to the side in exhaustion.

Sarah and Candace quickly dipped their faces to the still joined sex organs of Bobby and Jennifer, lapping up Ian's cum and then turning their attention to Bobby's as his cock fell from his mom's cunt. On the other end, Ashley and Dee licked Mark's cum from Jennifer's face, before alternating gentle kisses with her and then themselves.

When Jennifer, Bobby, and Ian were cleaned by the mouths of the girls, they crawled to each other, snuggling as much out of love as weariness. They drifted in and out of sleep as the girls began to entertain each other before focusing their attention on Mark, who, despite recently cumming as well, did not join the snuggling of the other three. He had lost time to make up with these girls, and he wasn't going to waste any of it on rest. Not that he was invited to snuggle anyway.

***

The groups enjoyed every inch of each others' bodies over the next week and a half. Bobby and Jennifer had taken vacation to make sure they could keep up with the demands of the recent college grads. Everyone's inhibitions were low and they lived like they never had to stop. The children were looked after by rotation. Everyone agreeing it was too risky to invite strangers in to look after them.

The adjoining properties kept their antics private, and the neighbors never came to investigate. Hopefully, unable to hear everyone's screams of pleasure. Everything was perfect, but there lingered a question amongst the original five. What had happened to Bella?

Each of them had tried to reach out to her several times over the last four years, but none of them had received a response. Her phone number was now used by someone else, and one by one her social media accounts were shut down after being dormant from the day she'd supposedly left for college. They'd all but given up hope of hearing from her, assuming something had happened with her family in Mexico and that she'd shifted her priorities. Until one sweltering afternoon when a familiar brunette rang the doorbell to Bobby's house.

Bobby opened the door with Sarah, Ashley, Candace, and Dee standing next to him. The familiar brunette was standing with her arms behind her back, anxiety strewn across her face, fidgeting as she hesitated to speak.

"Hi, Bobby. Girls. Everyone." Bella said, smiling nervously, knowing she owed everyone a long explanation, despite it being her parent's that forced her to move back to Mexico to not shame herself and the family with her unplanned pregnancy. Even then, she'd wanted to keep the girl, but she was taken from her. Not legally against her will, but she never would have signed the papers if she'd been thinking clearly. She'd been convinced she couldn't raise a child on her own, and that Bobby would abandon her. She knew better, even then, but her parent's insisted, pressuring her, even involving their old Catholic priest. In the end, it was the nuns who took her baby away to be given up for adoption. "I know it's been a minute, and I'm sorry for not reaching out. I've been through some shit, but I'm happy to have found my way back. Can you all forgive me?"

"Of course. We're here for you. Whatever you need," Bobby said, stepping forward and pulling Bella into his arms. Sarah, Ashley, Candace, and Dee completed the group hug, welcoming their lost friend back into the family. "And we have some new additions for you to meet."