Breaking in Bill

"That's pretty wild," Bill said. "Did you ever have more than one guy at a time again?"

"A couple of times," Carole said. "I actually called Roger one time after the separation. He had it arranged with one of his friends. They were both taking turns getting on top of me. And a couple of other times, AnnMarie brought home a guy for the both of us to share.

"Did you and AnnMarie touch each other?" Bill asked. He was very interested in this part of the story and was playing with his erection when he asked the question.

"We did," she answered. "She made me cum so hard with her tongue. We have fooled around once or twice since then when we were alone, but it just isn't the same unless there's a man around. We aren't lesbians."

Carole was done telling him everything. She drained a good gulp of her beer.

"So what do you think?" she said.

"What was some story," Bill said. "Was that the special treat you had for me?"

"Part of it, not all of it," she said. "I'm going upstairs," she said. "Why don't you join me in about 20 minutes?"

Up in her room, Carole slipped off her nightgown and put on black stockings and a garter, nothing else. She waited for him in bed, just like that first time they were together. Except this time around, there was no doubt about the outcome.

She was worked up by the stories that she told him and knew that he was, too. In exactly 20 minutes, she heard him trundling up the steps. She got on her hands and knees, her back towards the door. She wanted her son to find her like that right when he walked in. Indeed, Bill, gasped when he opened the door and saw his mother's ass in the air.

"Tonight," she said. "You're gonna live your dream. You are going to fuck your Mom in the ass."

Bill was out of his clothes in a flash. His dick stuck straight out.

"Thank you, Mom," he said, leaning over the bed to give her a kiss on the lips. She tugged at his cock.

"You're rock hard, you better get back there," she said. "Take the K-Y on the nightstand and lube up."

Bill climbed on the bed behind her. He put a dollop on his hand, wrapped his hand around his cock, and jerked a few times until it was slick. She reached back with both hands and spread her ass cheeks apart. Bill gaped at Carole's beckoning rear.

"Get my asshole, too," she said. "Work it in."

She felt a few drops sprinkle on the crack of her ass and then Bill's fingertips rubbing it around. He, somewhat roughly, inserted some inside her with his thumb. She winced and then worried about taking Bill's whole hard cock. She hadn't done this since she was married. She was glad that she teased him and forbade him from jerking off. He would be good and horny. He'd cum fast, unlike Saturday morning. She wouldn't sit for a week if he was back there for very long.

"OK, go ahead," she said.

Her son grabbed his cock in his hand and pressed firmly against her back door. It broke right through and slid in.

"Aye!" his mom said, in pain and surprise. "Go easy, please."

Not needing any more invitation, Bill grabbed his mom by the hips and gently slow fucked her ass. He pulled out no more than an inch with each thrust, but it was enough for them both. His eyes were locked onto the sight of his own cock penetrating his mother's rear.

"Oh my God. Oh my God," he whispered.

Carole could hardly believe it herself. She was breathing through her teeth like a woman in labor. She planted her face down on the mattress and bit the comforter. She rubbed her clit. She wanted to redirect the pain into pleasure. It worked. She came.

Bill slowed down. He wanted this moment to last forever. He stopped completely when he felt like he was going to cum. But it only worked for a minute or two. He shot his load into his Mom's tight ass. He pulled out and her asshole gaped as wide as a quarter. Semen streamed out.

What Carole planned that first night to be a one time incident to ease Bill out of his virginity became an affair that lasted several months. The routine was that sometime over the weekend Bill would pounce on her without warning and ravish her. She might be showering and he would climb in and stick his dick in her while the water was still running. Once he cornered her in the laundry room, lifted her up onto the machine, and got between her legs. She would be on the computer and his cock would suddenly appear in her face for her to suck. One time she was on the exercise bike in the basement and he snuck up behind her, pulled her tights down, and fucked her then and there from behind.

She also planned encounters herself. She and AnnMarie fooled around one night. Carole made sure to get a few pictures on her phone of AnnMarie licking her pussy. She e-mailed them to her son, who was all too willing to eat her out the next time he saw her. Another time, they were driving home from the supermarket, she pulled into an empty parking lot behind a warehouse and went down on him in the car.

At that time, though, she knew it had to end at some point. She was no longer giving Bill lessons to boost his confidence, she was just fucking her son.

She sat him down one Saturday and told him that weekend would be their last. They stayed in bed all day both days watching TV and having sex every couple of hours. Bill could no longer shoot loads and his balls hurt.

They never did quit completely. Once in a while, every several weeks, something would happen. Some nights she "couldn't sleep" and climbed into bed with him. Other times he would initiate something by slapping her ass, grabbing her boob, or flashing his cock. Sometimes it worked right away. Usually, however, Carole would respond with something like "not today". But it would put sex on her mind. And in a day or two she would tell Bill that he needed to "help her with something upstairs."

He would follow her up, his eyes locked on his mother's ass and his dick stiffening with every step.