The Affair Episode 04

Thanks to my editor Cheer_smartie526, this story was a lot more work that I thought it would be.

This series is intended to be like a TV series, you can start on any story and it should make sense, but is better if you start from the begining. That said, this one is closely tied to the one that follows it. Enjoy the story.

Brad glanced around the hotel lobby furtively. For the first time it felt like he was having an affair. He checked his phone again for a text message from Sherry. There was no change from the last time he checked, less than a minute earlier. This was the first time they had used a hotel, and Sherry had chosen a nice one. There were not very many people in the lobby, which is what he expected for a mid week morning. It appeared to mostly be business travelers. Brad wondered if anyone else in the lobby was there for the same reason he was.

Sherry spotted Brad fidgeting in the lobby. She looked at the clock on the wall and decided she was fashionably late as she strode across the lobby, the heels of her boots clicking loudly on the tile floor. It got Brad's attention, and the attention of several of the other men that were waiting to check in. Sherry was dressed professionally, but at the same time provocatively. Her skirt was short enough to show a little leg and her leather boots followed the contours of her calf muscles perfectly. The shirt she was wearing accentuated her large breasts. She knew she couldn't compete with the twenty-something blonde behind the desk, but she didn't have to. She only wanted to impress one man, and he was already staring at her.

"I've already arranged for a meeting space," Sherry said to Brad as she walked up to him, "please follow me."

Sherry turned abruptly as Brad began to stand. Today she was going to indulge herself a bit. Since Brad and Charlotte seemed to be getting what they wanted out of the arrangement, Sherry saw no reason why her needs, wants, and desires couldn't be addressed as well. Not that she had any complaints. Brad had proven more than capable in their sexual escapades. Sherry somewhat pitied the men that asked her out on dates. With Brad satisfying her carnal desires she was unlikely to indulge in a one night stand. She found herself being very selective about whom she hooked up with. So far none had equaled Brad's abilities in the bedroom.

As he followed Sherry across the lobby Brad found himself smiling. He wondered if anyone there knew what he and Sherry were about to do. Brad had always wondered about the people around him; where they were going, what they were doing. Sometimes he made up stories about them when he was stuck standing in line or waiting for some service to be completed. He wondered what stories people made up about he and Sherry.

Much to their disappointment they had company in the elevator. Sherry discreetly slipped a room key into Brad's pocket, and then stepped off the elevator one floor below the room she had reserved for them. She enjoyed the espionage; trying to be secretive about their affair spiced things up and made everything more exciting. The moment the elevator doors closed she headed towards the stairs. It would be good to have her heart rate up when she arrived at the room.

The room was nice. The most notable feature was the floor to ceiling windows. Brad noticed Sherry had left a small duffle bag in the room. It was zipped shut. He picked it up by the handles, trying to guess its contents by the weight of the bag. In one of the outside pockets was a paperback copy of the book Fifty Shades of Grey. He had just set it down when Sherry walked in. Brad suspected he knew the contents of the bag.

"I'd be lying if I said I didn't feel a little guilty about today," Sherry said as she approached.

"Why?" Brad asked.

"Usually Charlotte gets the first crack at you, but we are meeting pretty early today. Leaving your wife sloppy seconds doesn't seem right," she confessed.

"She had her chance this morning and politely declined. Charlotte likes sex, but once every few days is enough to keep her satisfied," Brad explained.

"Really, so she does not seem to be jealous?" Sherry asked.

"I wouldn't say jealous, but she does have a competitive streak in her. I think she has upped her game a bit because of you."

Sherry was suddenly intrigued, "Really, how so?"

"It's little things. She is starting to talk dirty, which is great. She also had been willing to get a bit rougher. Basically she letting her bad girl out to play just a little bit," Brad answered.

"You know, Charlotte told me about how you two have tied each other up. Based on what I am hearing from both of you I think it can go a bit farther," Sherry said with a seductive grin.

"Oh really," Brad replied.

"Yes, really," Sherry said as she walked to the large window and drew the curtains back. The view was impressive. The hotel was on the edge of downtown, so there were no tall buildings to block the cityscape outside the window.

"So you plan on tying me up?" Brad inquired.

"Oh yes, and then some. The one thing I'm not going to do is let you come. That is something I want your wife to take care of."

"I think I can handle both of you," Brad said, almost bragging. He felt like he had managed to perform quite well for both Sherry and Charlotte.

"You have, that's not the point. You are going learn about delayed gratification today, and then pass that lesson on to your wife. Well, that and I still feel a little guilty," Sherry explained. She suspected Brad's biggest challenge would be with Charlotte. He was quite eager to please, and Sherry wasn't sure he could deprive his wife of anything.

"So where do we start?" Brad asked.

"Right here," Sherry answered, "I want you to stand in front of me with your back to the window."

As expected, Brad quickly complied. Sherry retrieved the duffle bag. She noted that it had moved.

"Not where I left you, " she mumbled to herself.

"What's that?" Brad asked.

"Oh, Checkout is at eleven tomorrow. The kids can have sleep over at my place if you and Charlotte want to spend the night here," she replied.

Brad smiled. It would be nice to spend the night out. It wasn't unusual for the kids to sleep over at one place or the other. He often wondered what Sherry did on her nights alone. He knew that a few times it had been for work or a girl's night out. He suspected that other times were spent with other men.

Sherry stood in front of Brad and put her arms around his waist.

"I think you can lose the pistol for now, the zombie apocalypse isn't going to start today," she said when her hand encounters a lump on his hip. Brad removed his pistol from its holster and set it on the table.

"SIG 227," Sherry observed, "When did you switch to a .45? If I didn't know better I would say you were compensating for something."

Brad smirked and watched Sherry open the bag. The first thing she pulled out was a leather collar with metal rings on it. She put it around his neck. Next she extracted a pair of handcuffs. One at a time she placed his wrists behind his head and closed the metal cuffs. Brad couldn't see them, but somehow the handcuffs were attached to the collar.

Sherry paused. She wasn't done restraining Brad, but this was enough for now. She stood in front of him, her tits lightly pressed against his chest. Her hands found his belt buckle. She unfastened it and pulled the belt out then dropped it on the ground. Next she unbuttoned his pants and let them fall away. She hooked her fingers inside his underwear and pulled them to the floor, pausing to run her tongue down the length of his erection.

"You are mooning the city," Sherry said with a wry smile.

Brad blushed slightly, not sure if anyone could actually see him from the outside. The warm wet feel of Sherry's tongue had left him aching for the feel of her lips on his cock.

"So now what?' he asked.

"A lot of things," Sherry replied, "but your orgasm is not one of them. If you come I shall be quite cross. I want you to save that for your wife today. I, however, am under no such restriction. You are going to learn about delayed gratification. I'm going to focus on immediate satisfaction. Do you understand?"

As she was talking Sherry was shedding her clothes. She carefully removed each item. She hung her shirt on the back of a chair. After she released her ample bosom from the confines of her lacy white bra she folded the undergarment neatly and set it on the desk. She unzipped her skirt and wriggled out of it, noting the smile on Brad's face when he noticed she had not been wearing underwear. She left her calf high black leather boots on. Reaching into her duffle bag she produced a riding crop. Sherry swung it back and forth a few times, creating a whooshing sound. The expression on Brad's face didn't change; he still looked at her with burning lust in his eyes.

"There are a few things I think Charlotte wants you to do, although I doubt she realizes it. The first is she wants you to come in her mouth," Sherry said as she slapped the riding crop against her naked thigh.

"Every time I ask she says no," Brad responded.

"Don't ask, just do. Allow me to demonstrate. Get on your knees," Sherry tapped the back of Brad's leg with the leather crop and he immediately complied. Sherry placed the tip of the riding crop under his chin and forced his head to tilt back.

"But..." Brad started to say before being cut off.

"You are going to lick and suck on me until I come all over your face," she commanded. She put her hand on the back of Brad's head and pulled it towards her body. At the same time she thrust her hips forward.

Brad had never felt anything quite like this before. He had gone down on Sherry several times, but she had never been so aggressive about it. Sherry's hot, wet pussy ground against his mouth. At first he was overwhelmed. He felt the riding crop on his back and heard Sherry's voice.

"Suck, lick," she said sternly, "Make me come."

Brad ran his tongue along Sherry's labia. He wondered if this was what it was like to give a blowjob. He explored every wet fold of flesh he could reach. He wrapped his lips around Sherry's clit and sucked on it. She continued to thrust and grind against his face, coating him with her wetness. Her enthusiasm was contagious and Brad found himself pushing against her. His hands were still restrained behind his head. Sherry's bountiful breasts were just out of reach. He focused all his attention on the one part of her he could touch. He opened his mouth and sucked on the lips of her pussy. Sherry moaned in response. She tugged on his hair, pulling him in even tighter.

"That's it, don't stop," Sherry moaned, "I want to come all over your face, right there, right there, oh, that feels so good. Don't stop. Don't you fucking dare stop."

Brad had always tried to please Sherry, but it seemed even more imperative now. He didn't care who could see him in the window. He didn't care about his aching erection. His only concern was pushing Sherry to climax. He buried his tongue inside her as far as he possibly could. Her wetness flowed across his face and down his neck as she cried out. Sherry rammed her pussy against his face with such force Brad though he might be bruised, then she relaxed her grip on his head. He looked up at her heaving breasts. She pulled his head back, then leaned down and kissed him on the mouth.

"Did you enjoy that?" she asked breathlessly.

"Yea, yea, that was great," he replied.

"I think Charlotte will like it just as much as you did," Sherry said, pulling Brad back to his feet.

Sherry took a step back and ran the riding crop against the inside of Brad's thigh, "Spread your legs and bend your knees a bit."

Perhaps the slightly uncomfortable position would dampen his arousal enough for him to contain his orgasm, Sherry thought as she looked at Brad. Sherry retrieved an item from her bag.

"I know how watching me turns you on, so I thought this might help you, uh, contain yourself," she said, waving a sleep mask in front of Brad's face. She stretched the band around the back of his head, but left the mask just above his eyes. "We don't need it just yet, there is one more thing you need to see that might help ensure your wife gets what she is due."

Brad's arms were starting to go numb from being in the same position for so long, but he wasn't concerned. He watched Sherry bend over and pull something else out of her bag. She held it close to her chest.

She stood up and backed up until her body was pressed against his body.

"Still want to fuck me in the ass?" she asked, pressing her ass cheeks against his cock.

"Yeah," he eagerly replied.

"Still okay with my conditions? Are you still willing to take what you want to dish out?" she inquired as she pushed her hips back. Brad balanced precariously, trying to lean forward far enough to see Sherry's tits and whatever she was holding against them without tumbling over.

She whirled around, "Let's find out." In her right hand was a small dildo; in her left was a bottle of lube. She was calling his bluff. Sherry stepped forward, pressing her swollen nipples into Brad's chest. She put her arms around him, letting the tip of the dildo rest against his ass.

"Still okay with this? It's not too late to back out," she offered.

Brad swallowed. He leaned his head forward just enough to see Sherry's butt.

"I'm okay," he replied.

The next thing Brad felt was the lube dripping onto his skin, just above his ass. The liquid flowed downward and Sherry rubbed the tip of her toy in the thin stream of liquid. He heard the lid snap shut and the bottle hit the floor. Sherry pulled the mask over his eyes, everything went dark. She began to kiss him on the chest slowly working her way down.

"How....about...I...suck...your...cock...at ... the ....same... time," she said, kissing and licking him between each word.

He could feel her breath on his erection. He could also feel her toy gently pressed against his ass. Sherry wrapped her hand around his rigid shaft.

"Yours is much bigger, I think I'm going to have to upgrade if this is going to be fair," she said.

Brad felt an intense vibration from every word she spoke. Not coming was going to be a serious challenge.

Sherry released Brad's dick and picked up her riding crop. Starting with Brad's right ankle she let the leather tip slide along his legs, following the contour of his muscles. When she reached the top she stroked his balls like she was painting them. Next she inched along his throbbing erection, using the riding crop to spread the pre-cum all over his engorged head. Sherry flipped the tip over before she traced her way down the other side of his rigid penis.

She lifted it briefly, pressing the wet spot on the leather against her swollen nipple. When she pulled it away a string of precum stretched between her breast and the riding crop.

Brad felt the tip resting against his hip, and she began to hit him with it. At first she was very gentle, but with each stroke she smacked him a bit harder. He didn't know what to think. Brad had almost completely forgotten about Sherry's toy. The riding crop had his full attention. By the time the crop struck his ribs the impact had started to sting a bit. The sensation dulled as she worked her way across his chest. The combination of hair and pectoral muscles cushioned the blows until the leather tip slapped against his nipple. It was like an electric shock, but in a good way. Brad moaned as the riding crop found its target over and over.

"Make this quick," Sherry whispered to herself as she lowered her mouth onto Brad's cock. She enjoyed giving Brad blowjobs almost as much as he enjoyed receiving them. True, she had never had an orgasm from sucking on a dick, but she did find the feel of a thick cock between her lips very arousing. Making herself stop before Brad came in her mouth was going to be a challenge.

As Brad's erection slipped past her lips Sherry slowly increased the pressure on her toy. She had a matching dildo she had used on herself. She wondered if Brad was enjoying the experience as much as she did. If the hardness of his cock was any indication he wasn't turned off by what she was doing. When the resistance to her pushing leveled off Sherry knew Brad had accepted the full diameter of the toy. She pulled it out slightly, and then slowly pushed it back in. That was the part she had enjoyed the most, the feeling of being penetrated.

The first thing that crossed Brad's mind when the dildo touched his ass was that he had to make an appointment for his annual physical. That thought quickly faded when Sherry wrapped her lips around his throbbing erection. He focused on the blowjob she was giving him until he felt his orgasm building. Then he shifted his attention to what she was doing to his ass. It would be just his luck that her oral skills would give him a Pavlovian response to having something in his ass.

Brad felt the riding crop on his neck. He was amazed at Sherry's ability to multitask. Somehow she was fucking him with the dildo, sucking his cock and whipping him all at the same time. Unlike the blows to his chest, when the leather tip impacted his neck there was a noticeable sting. He realized he was approaching sensory overload.

"I...I...I'm getting close," he moaned. It was tempting to remain quiet and unload into Sherry's mouth, but then he wouldn't find out what else she had planned, and he didn't want to make her cross.

Sherry was relieved to hear Brad's admission that he couldn't take any more. Trying to do three things at once had taken some of the fun out the act. She dropped the riding crop and lifted her head off Brad's cock. The last thing she did was extract the toy from him. She wanted Brad to be very aware of what he was asking her to do for his pleasure. It was her intention that Brad understood that she wasn't his plaything. They were equals. His sacrifices needed to match hers, as did his pleasures. She tucked the toy into a pocket on her bag. For a moment Sherry hesitated, and then she reached in the bag and pulled out her own dildo and picked up the lube. She grabbed the riding crop and tucked it under her arm.

"How long can you stand me riding you cowgirl without coming?" Sherry asked as she put her hand on Brad's shoulder.

"With the blindfold and the handcuffs?" he asked.

"Yea, no point in you being comfortable or anything," she answered.

"I can handle it," Brad said as he moved his arms. His muscles were beginning to cramp, which detracted from his arousal.

"Three steps forward, then turn around and sit down," Sherry instructed. She watched Brad cautiously make his way across the room to the bed. He was frequently a bit on the timid side for her tastes. Sex was one of the few activities that brought out his adventuresome side. She put her hand on his shoulder and gave him a shove. He rolled over and landed flat on his back in the middle of the bed. He was right where she wanted him.

Brad felt a sense of relief when Sherry disconnected the handcuffs from his collar. He didn't mind that she attached them to something above his head. It felt good to have his arms stretched out. He felt her wrap something around each of his ankles. Like his arms, his legs were pulled tight.

After climbing onto the bed Sherry sat with her knees between Brad's legs. She set the dildo down and wrapped her fingers around the handle of the riding crop. Slowly she drew it out from under her arm. It gave her a sense of power, like she was unsheathing a sword. A stream of precum bubbled from the tip of Brad's erection. She swiped the tip of the crop against the head of his dick. Brad shivered in response.

"Are you still close?" Sherry asked.

"I'm good for now," Brad replied.