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“That was amazing, Imzadi, thank you,” Will Riker said, putting his napkin on the table.
“Thank you, but I can’t take all the credit. The replicator did most of the work,” Deanna Troi said with a laugh.
“It doesn’t matter. The meal was perfect. Now what’s left for our date night?”
“Well…I kind of had an idea for something new.”
Deanna got up from her chair and straddled Will’s lap.
“I’m intrigued.”
“I may have gotten a new toy that I want to try out.”
“Now you have my complete attention.”
“There’s no real delicate way of saying this…I will let you fuck me in the ass…”
“What?!” Will’s eyes widened.
“…if you let me do the same to you.”
He opened his mouth to speak and then closed it again. Deanna laughed.
“Speechless, huh? We’re off to a great start.”
She stood up and held up a finger. She walked into the bedroom and returned with a fairly realistic looking dildo strap on. She straddled him again.
“I will let you fuck me in the ass and do other things to me with this. But then I’m going to use this to fuck you in the ass.”
Will looked warily at the dildo.
“This could be a one time thing,” she said. “If neither of us like it, we won't do it again. But if we do, then we can add it to our repertoire.”
Deanna’s hand moved down to Will’s crotch and started rubbing it. He groaned.
“Okay, fine,” he said. “Let’s try it.”
Deanna’s dark eyes sparkled. She kissed him passionately before standing and held out her hand. Will took it and followed her into the bedroom.
Once there, she threw the dildo on the bed and they started kissing and shedding their clothes. Will picked her up and laid her on the bed. He climbed on top of her.
“Oh, we might need this,” she said, reaching into a drawer in the bedside table and taking out a bottle of lube.
“We’ve never needed that before.”
“I’ve never had a cock in my ass before. And, unless I’m mistaken, you’ve never had one in yours either.”
“Fair enough.”
He kissed her and squeezed one of her breasts with his hand. He ran his thumb over her nipple which hardened at his touch. He took her other nipple in his mouth and sucked it, flicking it with his tongue. His hand wandered between her legs.
“We may not need the lube, because you are already soaked.”
He lightly touched her clit and she inhaled sharply.
“How do you want to do this?” he asked.
“Surprise me.”
He grinned.
“Turn over.”
She got on her knees, her forearms resting on the bed, her ass sticking up in the air. He looked at her dripping pussy. His cock was ready to go, but he inserted a finger first. After getting it nice and wet in her vagina, he thrust his cock into her while inserting his finger into her asshole. As he filled both of her holes, he grabbed the bottle of lube. He removed his finger, spread lube on her asshole and two of his fingers before inserting them again.
Will…oh…
He didn’t want her to come yet, so he pulled his fingers and cock out. She whimpered with disappointment.
“We could stop here if you want,” he teased.
“No. Fuck my ass.”
“You asked for it.”
He lubed up his cock and put more on around her asshole.
“You will tell me to stop if you need me to, right?”
“Mmhmm.”
He ran his cock over her wet slit and ass crack. Then he pushed his tip into her asshole. He eased his big cock in slowly, Deanna’s breathing steady as his whole length disappeared into her ass.
He slowly moved in and out of her and her breathing grew heavier.
“Oh, fuck!” she exclaimed, not even bothering to say it inside his head.
Then she picked up the dildo and rubbed it against her pussy before thrusting it into herself. He almost came right then.
He pulled her up so she was against him. He kissed her neck and had a hand on breast as they moved together. Soon she was screaming with pleasure. It may have been the biggest orgasm she’d ever had, which made him explode.
She wrapped an arm around his neck and turned her head to kiss him deeply.
“That was amazing,” she said, breathlessly.
“You’re amazing,” he said, kissing her again.
They collapsed on the bed and he saw the dildo was still inside her.
“I’m just keeping it warm for you,” she teased. “But you can back out if you want.”
“Nope. I said I’d do it. So let’s do it.”
It was Deanna’s turn to grin. She took the dildo out of her and put it in her mouth, sucking her own cum off of it.
“Oh fuck,” Will said. He almost couldn’t believe that he was hard again already.
Deanna attached the dildo to the strap on and put it on.
“It’s a little weird seeing you with a cock,” Will said.
“I bet it is. Now get on your knees.”
“Yes ma’am.”
Will loved the domineering side of Deanna.
He assumed the same position she had just been in. This was a little weird for both of them.
Deanna put some lube on two of her fingers and Will’s asshole. Then she inserted her fingers and he groaned.
“Like it already?” she teased, thrusting her fingers in and out a few times.
“It’s definitely a different experience.”
She removed her fingers and lubed the dildo. It wasn’t as big or as thick as Will’s substantial cock, which would definitely be better for him.
She slowly eased the tip into his asshole.
“Relax,” she said, gently.
She took her time, but soon the dildo was buried in his ass up to the hilt. Deanna started moving as if the dildo was a part of her. She started moaning because the strap on was rubbing against her clit, so she would hopefully get a nice orgasm out of this experience too.
“Fuck!”
“Are you okay?” she asked.
“Mmmhmmm.”
She smiled.
She had one hand on his back and reached under him and wrapped her other hand around his hard cock.
“Oh fuck. Deanna!”
She was pounding his ass and with her hand working his cock, he came, hard. She continued her thrusts until the rubbing against her clit made her come again.
She rolled off of him, dildo standing at attention, since it was always ready to go. He turned onto his back and they entwined their fingers.
“What did you think?” she asked.
“It was weird. Kind of fun. But weird. I’m not sure if that’s really for me. At least not all the time.”
“Honestly, it was kind of weird to me too. Being in that position. We don’t have to do it again. I know there are other ways for me to dominate you.”
She smiled.
“I can’t wait. What about you though? Did you like the first part?”
“What do you think?” she said coyly as she climbed on top of him.
“I think we’re adding that to our repertoire,” he said, pulling her down for a kiss.