Try, try, try again

Gary felt Bernie's ring yield and stretch, and his broad cock head popped into her ass.

"We did it!" he said.

Bernie was standing in front of him in the upstairs shower, bent far forward to present her buttocks, and braced against the wall. "Yeah," she said, her face down toward the floor tiles. "Third time was the charm. It was way easier with Ben. I guess you're just that much bigger."

"Guess so," Gary said.

Two, Gary thought to himself. He'd been bareback up two asses, Sharon and Bernie. They'd started with a condom this morning, but he and Bernie had had so much trouble that they'd given up, and it was just silicone lubricant between his penis and her tight anal ring and hot, soft rectum.

Bernie was panting as Gary's cock stretched her rear door. "I dunno," she said. "I've had a toy as big as you before up there. I guess the real thing is just different."

"Yeah," Gary said. "How do you like it?"

"Intense," Bernie said. "And we'll have to figure out another position next time. But I'm so happy you're inside me there."

"Yeah," Gary said. "Feels good to me."

For their first try, Gary and Bernie had followed the advice in the Your First Anal Intercourse chapter of Your Family Doctor's Guide to Anal Sex, the same reference that Bernie and Ben had used together. Somehow they couldn't get the angle right, or the aim, or something.

For their second try, Gary had lain down on Bernie's bed and let her run the show. Another frustrating try had led to slipping, struggling, and Gary's erection softening as they tried to get the angle and pressure right.

They'd taken a break and went down to join Bernie's mom and Gary's sister for breakfast. The other two had headed out to the pool while Gary and Bernie headed back upstairs, determined to make a go of it.

The magic ingredients included an adjustable cock ring to keep Gary hard while they got the angle right, a warm shower to help Bernie relax, and a bottle of clinging, slippery silicone lubricant.

"Okay, you can start moving," Bernie said.

Bernie gripped her cordless, waterproof vibrator with one hand. When Gary had found his rhythm, quick shallow strokes, she clicked on the vibrator.

A few minutes later, Bernie's voice rose to a loud orgasmic cry. The vibrator clattered to the shower floor and she braced herself, striving hard to keep her knees locked and her feet planted as Gary finished off with a few quick strokes, a groan, and a hot spurt of semen up her ass.