In Bed With The Boss

* * * * The week before Christmas Richie started to whistle for no apparent reason. He smiled all the time and walked with a lighter step. This was the happiest he’d ever been in his life, especially at Christmastime. He had a man like Brad Lindsay, who was willing to leave his wife and make Richie his permanent lover. Richie was so happy he even decided to try out an experiment with Brad. Since they’d started seeing each other Richie had always been the submissive one in bed. He’d always been the one on the bottom. But Richie knew men like Brad Lindsay better than they knew themselves, sometimes. So one night, while Brad and Richie were getting ready to climb into Toby’s bed for one of their regular love-making sessions after work, Richie yanked his dick out of his underwear and said, “Why don’t you bottom tonight.” He shook it up and down and smiled.

Brad was naked by then. He’d already climbed into bed and he was under the covers. He laughed and said, “I don’t think so. I’ve never done that before and I’ve never wanted to do it either. I’m strictly on top. I don’t get fucked.”

Richie smiled. That’s exactly what both of the married guys he’d been with before had said the first time he’d suggested this to them. “Let’s just try it out and see what happens,” Richie said. He was dying to fuck Brad. In fact, he was dying to fuck in general. He’d always been more of a top than a bottom. And though he could bottom without any problem at all, there was something about poking a tight hole that caused his heart to beat faster.

“I don’t think so,” Brad said. He was still smiling. But he’d folded his arms across his chest.

Richie dropped his boxer shorts and stepped out of them. He grabbed his dick, loped to the bed, and climbed on top of Brad’s body. He moved forward and kneeled in front of Brad’s face. He rubbed the head of his dick across Brad’s lips. Then he slapped Brad’s face with the shaft and said, “C’mon, let’s do it. If you don’t like it we’ll stop and you can fuck me.”

When his dick touched Brad’s lips, Brad opened his mouth and licked the shaft. Then he started sucking the head very slowly, with just his lips. He closed his eyes and inhaled, as if savoring the taste, the texture, and the smell all at the same time. He took Richie deeper into his mouth and rested his hands on Richie’s hairy thighs and let out a gentle moan of pure satisfaction.

Richie glanced down at him and smiled. He caressed the top of Brad’s head and pushed his dick all the way to the back of Brad’s throat. Brad Lindsay was one of the best cock suckers Richie had ever met: a pure natural. He sucked with passion and used his lips and his tongue at the same time. He never complained about discomfort and kept sucking until Richie was close to climax. And Richie had never met a great cock sucker who didn’t like to get fucked…no matter how many times they protested in the beginning.

When Brad sucked dick, he took his time and enjoyed every last inch. They started out in this position, with Richie kneeling, and twenty minutes later Brad was on his back, sprawled out across the middle of the bed, and Richie was bucking his hips into Brad’s face. Richie stretched out as if doing push-ups over Brad’s head, with his palms braced on the edge of the mattress. His balls were against Brad’s chin. And Brad was slurping and sucking so hard Richie had to hold back because he still wanted to fuck him.

At one point, Richie got up and opened a jar of petroleum jelly. He lathered a few fingers on his right hand and rubbed the rest on his dick. Then he reached down between Brad’s legs and lubed his opening. When he did this, Brad’s entire body tightened and he set his palms against Richie’s thighs, “What are you doing?”

“I’m getting ready to finger fuck you,” Richie said. “Just close your eyes and relax. You’ll like this. Nice and slow, easy does it.” This was the first time Richie had attempted to play with Brad’s ass.

“I don’t want to get fucked,” Brad said. “It’s not my thing.”

Richie smiled and inserted the tip of his greased up middle finger. He moved it around and said, “I’ll just slide my finger in and out really slow. If you don’t like it, I’ll stop.” He moved his finger forward and he felt the lips of Brad’s anus clamp down. It was just as tight as he’d imagined it would be. His heart began to race and he bit his bottom lip.

“No,” Brad said, “Let’s stop.” He didn’t sound as convincing this time. His voice wavered and his tone became softer, with a breathy quality. And Richie noticed his eyes were closed and his lips were parted.

Richie’s finger went deeper and he started pulling it in and out slowly. He didn’t want to shock Brad. He just wanted to open him up and prepare him for the real thing. “That’s it,” he said. “Just close your eyes and let me do all the work.” Richie couldn’t deny that he was enjoying this. The deeper he went the softer it was.

“It’s not that bad,” Brad said. He lifted his legs and spread them apart. “But that’s it. Just your finger and nothing else.”

Richie smiled. “Don’t worry. I know exactly what I’m doing.”

A minute or two later, Richie inserted a second finger and didn’t even tell Brad he was doing this. When Brad lifted his legs and moaned out load, Richie started fucking him with two fingers. A few minutes after that, Richie inserted a third finger and Brad’s toes curled back. He even let out a scream, threw his arms back over his head, and arched his back. If Richie hadn’t known that Brad had never been with a man this way before, he would have thought Brad had been getting fucked in the ass all his life. But that’s usually the way it worked with guys like Brad Lindsay. They’d deny it and fool themselves into believing they weren’t interested in getting fucked. They were manly men, always in control; they only topped. But the minute Richie spread their legs and went to work they always wound up begging for more.

Though Richie was certain Brad would be like the others, he went a little slower with Brad and took his time. Brad had that aggressive, masculine personality in public and he seemed to care about his image. In many ways, Brad overcompensated in order to hide his true identity and he came off as obnoxious to some people. But Richie knew he and Brad had something special together and he knew that one day soon Brad would leave his wife and they’d be together all the time. Brad’s ass would belong to him then. Richie didn’t want to ruin it. So Richie didn’t turn him over until the moment he was certain Brad was ready.