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Josie opened the tube of KY jelly and squeezed some onto her fingers. Tom was still laying on his back on the bed, his pencil-like cock stretched out, hard, across his belly.

"Lift up your legs," Josie said.

Tom lifted his knees, his feet still flat on the bed.

"Higher," Josie commanded, slapping Tom on the side of the butt with her dry hand. Tom lifted his knees up to his chest, laughing nervously. His cock pushed into his belly. His balls lifted a little and the crease of his butt came into view. You could see his hole now. Hairless and open slightly as his butt cheeks splayed out on the bed.

Josie reached down with her lube-covered fingers and touched them to Tom's asshole. I moved in closer, partly to watch what she was doing, but mostly to be closer to her. As she leaned over Tom, her tee shirt left a clear view to the tops of her breasts which looked full and creamy white with a few freckles.

As she touched Tom's butthole it puckered closed a little at the contact. Josie put her middle finger against the opening, wiping the lube all over his hole. She pressed at the opening with her finger. The flesh around her finger began to indent slightly as she pressed, then her finger tip began to disappear into his ass, ever so slowly. Up to the first knuckle, then the second. It was half way into Tom's ass and Josie started to pull it back out. The ring of Tom's asshole tried to come along with her finger, then yielded and slid away as she slipped her finger out to the tip.

As soon as the finger was most of the way out, she started it back in again. There was no resistance this time and it slid back in, past both knuckles until her whole finger was in as deeply as it could go. Tom moaned a little.

"That hurt?" Josie asked.

"A little," Tom replied.

"Better get used to it quick," Josie said, "you've got at least two more fingers to go, before I'm done."

"Three fingers! No way," said Tom, "That'll hurt like hell."

"Bob, get up on your knees." I did as she asked, my cock a few inches from her face.

"Rub your cock, Bob, and get it completely hard again."

I reached down and stroked my dick. Looking down the front of Josie's tee shirt as she knelt behind Tom, I got a view of nearly all of her left breast. It was full and round, and when she shifted her position a little I could see the nipple, long and hard and red on the end of her breast, emerging from a small aureole, wrinkled with excitement. My cock got hard in no time.

"Look at this, Tom," Josie said, holding three of her fingers up to my cock. It was the first direct contact she had with my cock and her oily fingers felt warm against my swollen dick. "See this, Tom. Three of my fingers aren't as wide across as Bob's cock. If you ever plan to fuck my little ass, you're going to have to take my three fingers up your ass. If you can't, there's no way this big fat dick is going to squeeze in there."

When Josie mentioned Tom fucking her in the ass, he reached down and grabbed his own dick and pulled the foreskin back. He looked at my cock, lifted his legs back up so Josie could get at his ass and said, "Go ahead."

Josie put her forefinger into Tom's ass, slowly sliding it in an out. She pulled it all the way to the tip, then placed the tip of her middle finger along side it. Going slowly again, the fingers bunched together side by side, she slid both greasy fingers into Tom's ass. Tom flinched a little, but went on rubbing his own cock.

Josie continued sliding in and out until two fingers were completely buried in Tom's little asshole. Then she placed her ring finger in the bunch with the other two and started sliding all three into Tom's ass. Tom grimaced, but rubbed his cock faster and didn't make a peep.

I couldn't help watch as the three fingers pressed up into Tom's butt, disappearing into what looked like a solid wall of flesh. Josie was right. Three fingers seemed like a lot, but they weren't even the diameter of my prick and bunched together they were only a little wider than Tom's. I hoped that Tom's ass wouldn't strip the skin off my dick. It would definitely be as tight a squeeze as my dick had ever felt.

I looked at Tom's dick again. He pulled the long foreskin all the way back, then slid it forward until it stretched up over the bulb-like head, completely covering the tip of his cock. Josie was definitely going to get the easier part of this deal, Tom's cock would be a breeze compared to mine. I wondered if she would be able to take its enormous length, though. Suddenly Tom yelped, and I looked up from my daydream. Josie was holding her fingers about two thirds of the way up his ass and slowly opening and closing them so that they were bunched together and splayed apart. Now she was getting closer to my size, but still not quite there.

Josie said, "That's oily enough, I think," and slowly pulled her fingers out of Tom's butt. The hole seemed to stay open slightly, then suddenly closed up as small as when she had started. Josie turned to me and said, "Now it's your turn."

She squeezed KY out onto the palm of her right hand and reached out for my cock. Slowly, she slid her oily hand down over the head of my dick, twisting as she went to distribute the lube around the head. Her hand was warn and she wiggled her fingers as she oiled me. It felt great. I hoped that she wouldn't spend too long at this, or I would be spewing come all over her hand.

She brought her face up close to my dick and looked at it as she slid her hand down the shaft. The skin pulled taut at the base of my dick and my pre-cum began to ooze from the tip. Josie stuck out her tongue and touched the tip to the hole of my slippery dick, collecting the droplet that had formed there. She looked at my cock and her hand upon and seemed to be measuring its girth. Her face flushed a little, as her hand barely got halfway around my dick. Suddenly she stood up, still holding my dick and pulled me over to where Tom still lay on the bed with his legs up, pulling at his own cock.

Josie asked him, "Are you ready?"

"I guess so," Tom said.