It goes okay (Luck: -10 Supicion: -10)

"Oh the lube!" Jonathan said remembering basic preparation. He darted back to his computer and was back in a jiffy.

"OH yeah we will want that." Leah teased him adding "Good thing you had it out already."

"Yeah yeah yeah." he said moving into position behind her. He squeezed out a healthy portion of lubricant on his cock and stroked himself. The cold lube made him shudder for a moment but he was very eager to fulfill his fantasy.

"Should I just put it in? Or like finger you first?" he asked awkwardly. Questions about fingering someone's asshole were never a very natural topic for most people.

"Just go real slow." she said as she helped spread her cheeks. "And stop if I say stop--okay?"

"Of course." he nodded to Leah who had turned to look back at him.

He moved his cock's head up to Leah's asshole and fumbled for a moment or two, the lubricant making things slippery. Then he found just the perfect spot, leveled his cock, and pushed forward slowly.

"Ooof!" Leah said as she felt his manhood begin to enter her exit-only orifice.

"You okay?" Jonathan asked, spotting any further movement.

"Yeah yeah...just I'm good, keep going babe." Leah said encouraging him.

He needed little encouragement, he soon put another inch inside her and another and another. Finally he was all the way inside her.

"OH GOD you feel so fucking good." he said with a groan as she sat there his cock balls deep in her tight asshole. "Shit its so fucking tight. GAH!"

He began to slowly move his cock back out, not all the way but just to the tip.

"Ughghgg!" Leah cooed as she felt him push himself back inside her.

"Fuck...." he groaned as he thrust again. He continued to groan with each thrust. It hadn't even been a dozen pumps before he felt himself about to cum.

"God I am gonna cum already. Gahhhhh!" He thrust himself forward deep inside Leah as he came. He didn't even let out a string of grunts like normal as Leah's tight asshole was so snuggly wrapped around his quivering cock that he had never experienced such pleasure.

"Ogh!" was all he could manage as he came deep inside her. Leah felt the awkward fluids fill her. It felt like a ton. And he hadn't even gone for a dozen thrusts. In his defense, he had been beating off earlier and was very...primed for excitement. Plus he had just been given the opportunity to fulfill his fantasy. So even Leah couldn't blame him. In fact, she even took a bit of pride in knowing that she had made him cum so quickly.

Jonathan didn't even thrust so much as to shake through his climax. Leah was just so tight he couldn't do much else but keep from yelping in pleasure. After he finished....shaking? He withdrew himself from Leah's hole. A flood of cum followed him, making quite a mess.

"Holy shit...." He leaned back on the bed and let out a few heavy sighs.

"Looks like someone was excited." Leah said playfully as she felt the stream of cum flowing down her.

"God that....felt so good...shit...." he smiled at her.

"I'm glad you enjoyed it babe." she looked toward the bathroom then asked "Can you get me a towel? You left a bit of a mess." she winked at him playfully again. She wanted to fulfill his fantasies. She loved this man so much.