Bernie's turn to bottom

"...Not Bernie yet," Gary said.

"Soon!" Bernie said. She looked over Peter, lying in the middle of the bed, to her boyfriend Gary. "Hey, maybe really soon. Look at you, all hard again!"

Gary's cock was showing definite signs of life. It hadn't been long since Gary shot off while Peter fucked him and stroked his cock, but hearing Peter talk about fucking Gary's mom and dad and Peter's own mom and dad on the cruise had given Gary a jolt. His thick shaft swelled, lifting up off his balls and rising from his blond patch of pubic hair. The prominent head was still half-covered by his foreskin but looked soon to show up.

"So how many guys have you had up your ass now?" Gary asked Peter.

Peter laughed. "You. Your dad. My dad. And if a strap-on counts... Sandy. And my mom."

"Whoa," Gary said, thinking of Sally Walker's long slender form rocking as she thrust her hips into Peter.

Bernie smiled. "Busy guy." She squeezed Peter's shoulder.

"How about you, Gary?" Peter asked. "Just me?"

Gary swallowed. "Well, you. And Stuart. Right before he took off for his trip. In the back of his van, before he gave me the keys."

"You didn't tell me," Peter said.

"Yeah. I was still thinking about it. That was my first time," Gary said. "We had some weed. I was really pretty high. So I just said yes when he asked. He sucked me hard and took me from in front like you did. I came when he was fucking me. Really hard. No hands or anything. So I still kinda didn't know what to think about it. Was it just being high or what? Then last night when he picked up his van, we got together again."

Bernie nodded. "Yeah," she said. "I was there too."

"Oh?" Peter said.

Gary laughed. "Yeah, that's our deal now," he said. "Bernie's gotta be there. So, yeah. Stu got up in me from behind and gave me a reach-around. It felt good to have his cock in me. Straight, sober, and everything. And pow, he got me off and shot his load. It worked. So that's partly why I was ready to say yes tonight."

Peter laughed. "And Bernie talking you into it," he said. "I love your ass, man. It felt so great finally getting in you."

"Yeah," Gary said.

"So Bernie, are you experienced?" Peter asked.

"Weed makes me throw up," Bernie said. "Nasty stuff."

"No, I'm sorry," Peter said. "I meant to ask have you had anal sex?"

Bernie smiled. "Yeah. I like it a lot. My girlfriend Habiba really got me into it, and my mom, you know, Ms. 'Free To Masturbate'?"

Gary laughed. "We had her book in high school."

Bernie said. "Yeah. Mom is always like, about how it's also an erogenous zone. She likes to finger her ass when she masturbates. Me too sometimes. But I didn't tell Gary I liked anal play because I was worried he thought it was dirty."

Gary said. "Me too, and you know, Sharon liked anal a lot. I wanted to do something different so I wouldn't be thinking about her."

Peter nodded. "Yeah, well, Sharon."

"But we're ready now," Bernie said. "I've got a cousin Ben, he's kind of the guy, well..we've never dated. We drive each other crazy, kinda. But we sort of have a deal that we try out new sex things together. So we don't embarrass ourselves in front of a boyfriend or girlfriend. Because we were both shy and slow to start out, it helped. The last time I went to visit him at college, the new thing we did with each other was anal. We did all kinds of things, you know, touching and kissing each other there. Putting our fingers in our own butts and each other's. Toys. Anal intercourse. I brought my strap-on so Ben could get it too. It was mostly really fun." She pushed her glasses back up her nose and ran a hand through her curly dark hair. "So Gary, what do you think? Now now?"

"Okay," Gary said. He sat up, his erection sticking up from his lap. "Move over, Pete."

Peter found a fresh towel to put on Gary's bed. Gary put on a condom to make clean-up easy. He stroked lube up and down his shaft. Bernie got on her knees and bent forward in the middle of Gary's bed.

"Do you want to lick me, there?" Bernie asked.

"Yes, very much," Gary said. He knelt behind his girlfriend and put his hands on her buttocks, spreading her open. She was self-conscious about her big ass, but for Gary it was outstandingly sexy. He turned his head and bent to kiss her pussy.

"Mmm," Bernie said.

Gary straightened up and licked up, up, up...there. "Mmmm," he said, kissing Bernie's ass.

"Yes," Bernie said. "Yes. Oh yes."

Gary's cock hardened. Hot. Sexy. And nothing like Sharon. Bernie was shy and sweet and loving. And her ass even tasted better than Sharon's. He licked, listening to Bernie's soft sighs.

"Oh, get inside me," Bernie said.

Peter handed Gary the bottle of lube. He freshened the coat on his cock and squeezed a big dab on Bernie's ass. Gary knelt up and pointed to his new target, pressing gently. Bernie pushed out at him, opening herself, and welcomed him in.

"Oh yes!" Bernie said. "Oh, you're big. But good!"

"You feel so good," Gary said. "Hot. Really tight on me."

"Start moving," Bernie said.

Gary started thrusting.

"Oh wow oh wow oh wow," Bernie said.

"I feel you squeezing," Gary said.

"Yeah, I don't know, I think I'm gonna, maybe...keep going, keep going," Bernie said.

Gary kept thrusting gently. So hot inside. Her ring so tight and slippery.

"Oh, OHHHH!" Bernie cried out. Her head dipped, then rose. Her glasses fell onto the pillow.

Gary felt Bernie's ass squeeze down tightly. "Oh, Bernie, wow, me too, gonna..." Gary said. His hands tightened on Bernie's buttocks. His cock swelled inside her hot ass, and his climax came to meet hers.

After a minute just staying still on wobbly knees, Gary eased back out.

"Wow," Gary said.

"Wow wow." Bernie echoed.

Peter helped them clean up. "Isn't that, like, never? Simultaneous orgasm from first time anal?"

Bernie laughed. "Not never. I was really wanting it, and well."

"Huh," Gary said, half-drowsing. "Well, yeah. Well."

Peter laughed. "I'll just let myself out, then."

He dressed and let the two lovers drift off together.