Yes

Tony's body was already struggling to deal with the unfamiliar sensations Katie's finger was creating in it, but it wasn't unpleasant. Who was Tony kidding? It was great. Very strange, but great. He wasn't sure how much more he could take, but he knew if he took it slow, it would take forever for him to be ready enough for Katie, and he didn't want to make her wait any more than absolutely necessary. Up to this point, his concern was for making Katie wait, but after feeling what a single finger could do... He nodded. "Yes. Let's do it."

Katie smiled. "Alright then. Let's go!" And with that she pulled her finger out. Tony's sphincter closed, leaving Tony with a strangely empty feeling in his ass. This thankfully wouldn't last, as Tony felt two of Katie's fingers pressing against his hole. Unlike the first time, Katie had to work a bit harder to slide her fingers inside. However, when she did...

"Fffffffuuuckkkk...." Tony hissed out. His anus had to stretch to fit Katie's fingers this time, and it was sending his poor overwhelmed brain another mix of pain and pleasure. Katie started thrusting her fingers inside of him again. All traces of pain disappeared as Katie's fingers repeatedly hit his prostate.

Katie smiled as Tony whimpered and moaned. She leaned over him, whispering into his ear. "Tony, I'm going to stretch you a little, okay?" Tony nodded. "If it hurts too much, just let me know. I don't want to hurt you."

"I know." Tony turned to look at her. "I trust you, Katie."

Katie slowly started to separate her fingers. Tony bit his lip. Once Katie had stretched him as far as she dared, she stopped. "Are you okay?"

"Y-yeah", Tony whimpered.

"I think this is as much as we can do today. We'll need lube to go any further." Katie brought her fingers back together. "So Tony, ready to cum?" And with that, she resumed thrusting with her fingers. Tony began to shake as Katie hit his prostate over and over, sending waves of pleasure throughout his body each time. He began to hump the air, his dick at full mast, **** for stimulation. Stimulation that Katie was all too happy to provide. She grasped his penis with her other hand and began to jerk him off.

Tony grunted as the combined forces of Katie's hands brought him to the brink of orgasm. "I... I'm gonna...!"

As soon as Tony said this, Katie stopped, and pulled her fingers out.

"Why did you..." Tony started to ask, but Katie gently but quickly flipped him over onto his back.

"This is why. Now cum for me, Tony!" Katie rapidly stroked his cock, and put her fingers back into his ass for one final thrust. And with that, Tony came.

"Fuuuuuuuuuuck!" Tony grunted. Jet after jet of semen shot out, landing on his stomach, although the first shot almost hit his face. As the last spurt dribbled out, he lay there, gasping. "Wow, that was... wow."

"I'm glad you enjoyed it," Katie smiled down at him.

Tony looked down at his cum-covered stomach. "Wow. I've never cum that hard in my life."

Katie giggled, bringing a smile to Tony's face. "It's a shame it didn't hit your face. I think you'd look cute covered in cum."

Tony never would have even considered doing this before today, but he'd done a lot of things today he'd never even considered doing before... So, fuck it.

He sat up and grabbed Katie's dick. "What about you? Don't tell me you're spent after only one blowjob!"

She, in fact, was not, as her rock hard rod made abundantly clear. This, however, was the only part of her body that was communicating clearly. She was blushing, covering her eyes with her hands, and was making what Tony thought were the cutest sounds he'd ever heard. "I...I...uh...you...um..." Tony grabbed her womanhood with both hands and started stroking.