Something 'Ryan' hasn't done in 4 years

Mrs. Anderson continues to circle her desk, removing her blazer on the way. "You know as the warden here, I am privy to a lot of information. Like the physique of my inmates."

She then bites her lip.

"And I know under that prison uniform is a big, fat, cock."

Isaac smiles at Mrs. Anderson. "There sure is."

Smiling back, Mrs. Anderson throws Isaac a condom. "Take this. I know what you prison boys get up to."

Nodding, Isaac kicks off his sneakers and stands up. He then unzips his orange overalls and removes them, revealing his new, muscular, ink-covered body. After removing his briefs, Isaac looks up to Mrs. Anderson, who's just unbuttoned her blouse. She proceeds to throw it open, flaunting her petite beestings, which are still rather perky considering her age.

Isaac moves towards Mrs. Anderson with lust in his eyes. She might not be as attractive as Mia, but that didn't stifle Isaac or his growing erection. As he grew harder, he tore the condom wrapper open. Rolling the rubber of his new cock, Isaac gained a real appreciation for how much it dwarfed his old member. Looking back ot Mrs. Anderson, he finds her sitting on the edge of the desk, her skirt hiked up and her panties pulled to the side.

"Ready for your first piece of pussy in four years?"

"Hell yeah."

Without further ado, Isaac pressed his tip against the lips of her entrance. As his cockhead presses inside of her, Mrs. Anderson gasps "Go slow... You're so much bigger than my husband."

Despite his excitement, Isaac heeds her words, slowly thrusting away. Her moans are music to his ears, and her slit is a welcome change to his hand, even if the sensation was muted somewhat by the condom. He also indulged in the sight in front of him. A woman who's practically naked with a smile, enjoying every thrust he's giving her. For the longest time, this had been his dream, and now it is finally his reality.

"Ah... How does your first pussy in four years feel?" Mrs. Anderson cries.

"So good." Isaac replies.

"Yeah? How about you give it to me harder?" She growls.

"Sure."

Isaac pistons harder, bracing both hands on the desk that begins to shake. This makes Mrs. Anderson cry out in ecstasy, without regard for any guards who might hear her. Isaac didn't stop either. In fact, only a fool would try to pry him away. Mrs. Anderson makes sure to snare him in between her legs, before reaching for her clit, further adding to her pleasure.

"That's it... Fuck me like my husband never could."

Her words spurred Isaac to pound her as hard as he could. She soon lost her grip and fell into her desk. 'Ryan's' cock continued to overwhelm her, making her legs tremble. Then her eyes rolled into the back of her head, before she finally declared "You're gonna make me cum!"

That's when her body convulsed, overwhelmed by pleasure. Isaac managed one last pump before erupting inside of his condom. Now finished, he slides out of Mrs. Anderson who sits back up. She proceeds to kiss his lips, before saying "If only I could keep you in here."

"If only." Isaac replied.

"No go on. The Feds will be here soon."

"What do you want me to do with the condom?"

"There's a bin by my desk."

Isaac nods, before discarding his used rubber. Next, he gets dressed and gives Mrs. Anderson a wave before leaving her office. Outside, a guard escorts him back to his cell, seemingly none the wiser to what just happened. Back in the cell, Isaac begins to wonder what his life in witness security will be like, hoping it'll be better than the one he's left behind.