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Can Bailey Take It?

Category: Anal Sex
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Work had been a beast this week. Normally Bailey loved her job, but this week, she was ready to throw both her computer AND her cell phone out the window. As the Office Manager for a small construction company, it was her job to make sure all the employees in the office did their job correctly and everything ran smoothly. Most importantly because she was the only employee in the office. And her boss was a stickler for perfection.

Her office was in a warehouse where they kept material. They didn’t get many visitors, which was fine with Bailey because she could wear jeans and a t-shirt all year round. Her boss had an office behind hers, which she never really understood why, since he used it only about twice a year. There was a kitchen and a bathroom in the back. Sometimes Bailey got lonely, but usually at least once a day one of the construction guys would come by, or sometimes a vendor would pop over.

This past week, however, it seemed that everyone on the planet had come to visit. The boss, Mr. Wyatt, owner and President of Wyatt Construction for which one Bailey Sinclair worked, seemed to have taken up residence in his office. There was a problem on one of the jobs so three of the workers were in the shop fixing and cutting and making a shit ton of noise, and the phone seemed to have a life of its own. Oh, and to top it all off, Monday’s payroll got all janked up. Monday, of the week that Mr. Wyatt was working 20 feet away from her. Shit.

Now, on Friday morning, Bailey’s peaceful world felt like it would never return. Frazzled like an espresso OD, she turned on some music and decided that if she just got back to routine, she would at least try to finish the work she had left and maybe knock off early. Being an Office Manager did have some perks.

About 10:00 the phone rang and Bailey realized it was for the first time that morning. Caller ID said it was Rick from one of the lumber supply companies that they used. She smiled as she answered the phone because Rick was always friendly and she enjoyed talking to him. She dealt with a lot of the vendors and some were really nice, some were ok, and some were downright assholes. Rick was close to the top of her like list. He was kind of hot, too, with just a touch of a Texas accent. She had to refocus on what he was saying because her mind had definitely just run off to a place it shouldn’t have.

“…drop off a new price sheet if that’s ok?” Rick had been saying.

“What? Oh, yeah, sure, what time did you say? I was thinking of leaving early today,” Bailey blundered, feeling foolish for not paying attention.

“I was thinking in about a half hour or so. Will that work?”

“Uh, sure. OK”

“Bailey, are you ok? You don’t sound like your normal chipper self.” Rick had real concern in his voice.

“No, I’m fine; it’s just been a long week, that’s all. I appreciate you asking. See you soon,” Bailey said as she hung up the phone and put it back in the holster on her belt. Under normal circumstances, she would really love to see Rick, but today she just wanted to go to go home and not think about work until Monday morning.

She decided to go look at herself in the mirror to see how horrible she looked. “Oh my God,” she said out loud to herself. She definitely had some dark circles under her normally bright blue eyes. Even her curly strawberry blond hair seemed to be tired as it was just limp today. Double shit.

About an hour later she heard the outer door close and tired as she was, her tummy gave a little flip while expecting Rick to fill her office with his presence. He wasn’t that big of a guy, maybe only 6′, but when he came into a room, you knew it. He had a nice build on him, and his casual clothes seemed to emphasize that. He always wore jeans, a white t-shirt and some kind of opened button up over that. He exuded confidence which was sexy as hell to Bailey. Of course, his looks didn’t hurt either. He wasn’t drop dead gorgeous, he had brown hair, brown eyes, but there was just something about his face that made you do a double take.

And there he was, filling her doorway, standing there with his hands on both sides of the door jamb, one foot casually crossed over the other one. Just like always, his red button up was wide open, exposing the brilliant white t-shirt underneath tucked into his jeans. Bailey immediately felt her heart beat just a little faster and internally scolded herself for acting like a school girl.

“Hey, Bailey,” Rick said as he smiled down at her. “Uh, I mean this in the nicest way, but, honey, you look like hell.” He dropped his arms and started toward her desk.

Bailey went three shades of red before she found her voice and was able to respond. “You sure know how to woo a girl, Rick. Is that your best pick up line?”

“No, I have plenty of them, but I don’t think you need a pick up line right now. Would I be too bold if I offered you a shoulder massage? I can just see the tension on your face. And I hate to see your pretty face anything but beaming sunshine like it normally is.” He was blushing a little at his last comment.

Bailey didn’t know what to say at that. The thought of Rick’s hands on her made her tingle, and what she wished he would do with those hands started making her hot and come to life a little bit. But she was at work, and he seemed like such a gentleman. Screw it. “I would love nothing more, Rick. Are you sure you wouldn’t mind?”

“Mind?” he asked as he started moving toward the back of her chair, “I enjoy this. You just have to let me know if I am rubbing too hard, ok? I didn’t always sell stuff, I used to work on a farm too, so sometimes I can forget to be gentle.”

He started rubbing her shoulders and the nape of her neck and immediately Bailey felt some of the tension release. But now Bailey was having a new problem. Rick was turning her on. She was tingling, getting hot, and now she was getting wet. Rick kept massaging her shoulders and back and neck, and the more he touched her, the more Bailey was getting turned on. Her nipples were at full attention and with the t-shirt she had on, she was pretty sure that Rick could tell they were hard. He moved her forward a little so he could reach more of her back, and Bailey moaned a little.

“Are you liking that?” he asked, his voice a little husky.

“God, yes. That feels wonderful,” Bailey managed to whisper out.

“Not too hard?” he whispered back.

“Not hard enough,” Bailey heard herself reply. Wow, what was going on here? she thought.

“You like it hard?” he growled, and Bailey got the implication. She had a split second to make a decision. She could stop this now, or she could go all the way. She could get caught if someone came in. She didn’t care; this week had sucked so bad, she actually didn’t care if anyone walked in, even Mr. Wyatt, although he had told her yesterday that he was taking today off. She was on the pill, so she didn’t care about that. She was going to hope to God that Rick didn’t have any disease. Hmmm, sounded like she had already made up her mind.

“I love it hard,” she said as she turned her chair and came face to face with the fly of his jeans. His cock was stiff enough to make a nice ridge in his pants. She looked up at him, “I want to taste you.”

Rick’s eyes got just a little bigger as a smile crossed his face. “You do, huh? Well, I want to see your tits.”

Bailey couldn’t help but smile back. “Fine, but after I suck your cock. Release it now before I start biting through your jeans.” She could feel the wetness between her thighs increase and put her hand there for just a second. She heard Rick suck in his breath as she did and she liked knowing that she was turning him on as well.

He had unbuckled his belt and taken his pants down a bit and she watched as his cock sprang up to greet her. “Sweet Jesus,” was all she managed to get out before giving in to her desire to taste him. He had such a clean scent, like he had just gotten out of the shower, and there was just a hint of cologne that she could smell. She felt herself getting even wetter and she didn’t know how long she could suck him before she wanted to launch herself on his cock and ride him until she came herself.

But she absolutely loved giving blow jobs. So she started with her tongue and made small circles around the head of his cock. She held his shaft in one hand and his balls in the other and felt his cock twitch when she used her teeth to gently rake across the top of the head. He moaned and she smiled knowing that she was making him feel good. She took his cock into her mouth just about an inch, then back out, then an inch more, then back out, and kept doing that until she had made it wet all the way down. Another circle around the head with her tongue and she plunged the whole way down his cock, taking the whole thing in her mouth. Rick gave a tiny scream and grabbed Bailey’s hair and started rocking her head back and forth on his cock. This was her favorite. She just loved having her hair pulled, and they developed a rhythm. He pulled, she sucked. She used her tongue to massage his cock on every stroke and with every stroke she got wetter and wetter. She still massaged his balls, but she used her other hand to massage her clit and she was only moments away from cumming herself. Every so often Rick would stop their rhythm so that he wouldn’t cum, but she kept playing with her clit, sticking her fingers in her pussy, loving how hot and wet it was inside. Finally he grabbed hold of her hair and pulled so hard that it made her scream, and it made her cum, which made her scream more. But her mouth was full of cock, so it didn’t make any noise, just a vibration on his cock, which made him shoot his load into her mouth. He expected her to either spit it on his cock or his stomach, but she kept sucking and soon she was making those little circles on the head again, with an open mouth. Yeah, Bailey was a swallower. Rick got even more turned on by that.

“Come here,” he said to Bailey, and pulled her up from the chair. He moved so quickly that she giggled because before she knew it, he was sitting in her chair, pants pooled around his ankles, and she was in his lap with her jeans only partway on.

“Wow,” he said, still breathing hard. “That was fucking fantastic.” He wrapped his arms around her waist and closed his eyes.

“No, that’s later,” Bailey said, poking him in the stomach, “and you have it wrong.”

Still with his eyes closed he said, “What are you talking about?”

“The fantastic fucking is later.”

She felt his chest move with laughter as he sat her upright and looked at her. “So, are you still tense, Ms. Bailey? ‘Cause you look a whole hell of a lot better than when I walked in here.”

Moving here shoulders back and forth and her head side to side, Bailey said, “Well, I guess a little better, but I think I need some more massage sessions. When do you think you might be a-hem, up for one?”

“What are you ready to go again already? You wanton woman, you! What are you doing tonight?”

“Really? I’m leaving early, that’s what I’m doing. And you’re on! Show me what you’ve got. Where and when?” Bailey was getting horny again just thinking about Rick and what they might do later. She had some plans for him, but this time it was going to be her turn to be the recipient.

“I’ll take you to dinner first, Mario’s, 6:00. We can go from there.”

“Nah,” she countered. I have food at my house. I already gave you a blow job, so you know I don’t need to be wined and dined first. Here…” she scribbled down her address and handed it to him. “Be there at 6:00. If you’re hungry, eat before you get there. I want to be ready for some business when you show up.” Bailey got up and put herself back together as best as she could, as did Rick.

“Scoot and let me finish my work so I can get out of here,” she said with a wink.

As she watched Rick leave she couldn’t help but think, what in the hell just happened here?

By 5:45, Bailey was ready to puke. Ok, a blow job with a guy she hardly knew was one thing, but hell, she had invited the guy over for sex! And the way she did it was like, Hey baby, come on over to my place for some steamy hot sex, even though I really don’t know you. What the fuck! She didn’t have his number to tell him not to come. She kept hoping he wouldn’t show up. RIGHT! She kept telling herself that when he showed up she was just going to tell him she couldn’t go through with it and hope that he was a nice enough guy that they could sit and talk and laugh about it.

6:00 on the dot her doorbell rang. Shit. She looked through the peephole and there was Rick and for the first time, she couldn’t see a white t-shirt. She opened the door and immediately felt like a jackass because other than take her shoes off, she was still in her work clothes. Rick had put on nice slacks and an actual dress shirt. And buttoned it up. Double shit.

“You wanna let me in or do you just want to do it out here for your neighbors to see,” he teased.

“Shut up,” she said as she moved out of the way to let him in. Her house wasn’t all that big so she gave him the brief tour, avoiding the bedroom on purpose, deciding to start things off in the living room. She hoped he wouldn’t notice the bedroom oversight. He did, of course.

“Waiting for later to show me the bedroom?” he asked while waggling his eyebrows, and making himself comfortable on the couch next to her.

Bailey might have gotten mad, but damn he smelled wonderful. She didn’t know what he was wearing, but holy shit she wanted to go sit in his lap again. Just thinking of that made her start to tingle and for a second she started to second guess her plans for the night. It had been a long time since she had had a good fuck. Maybe this would be a good night after all. Hmmmm.

“What are you thinking in that mind of yours? I can see some wheels spinning,” Rick said looking at her with suspicious eyes. “Are you having second thoughts about tonight?”

“Yeah. No! I mean, I was, but now I’m not sure.” He stopped her talk with a brief kiss on the lips. He lifted her chin so he could see her eyes, which had fully recovered from the week’s drama and were back to their azure hue. “What?” she asked.

“Tell me what you want,” Risk said in a smooth tone that instantly put Bailey at ease.

“Uh, well, do you have any diseases I should know about,” she blurted.

He chuckled and put his hand on her thigh, “No. I’m a card carrying member of The Disease Free Club, but I have it framed at home, so if you want to see it, we have to go to my place.”

She stuck her tongue out at him.

“Watch it, I know where that tongue has been!” he teased, but he looked at Bailey and saw that she wasn’t laughing. “You’re serious, what else do you want to know?” At that he pulled “The Man Pose” where he leaned back on the couch and put one ankle on the other knee.

Bailey tucked one bare foot up under her bottom and expressed her concerns, which actually made Rick feel better. He told her he had the same ones and was glad they were talking. After about an hour Bailey asked if he wanted some wine or beer and he said that he had a penis so he preferred beer. Again she stuck out her tongue. He offered some suggestions of what she could do with it.

“Keep up the sweet talk and I might just take you up on your offer,” she retorted as she went to the kitchen to grab a couple of beers from the fridge. Like a panther he had snuck up behind her so that when she turned around she bumped right into him.

He took the beers out of her hand and placed them on the counter behind her without either of them moving. With his hand still partly behind her, he deftly reached her bra and with one swift “pluck” undid her bra strap. She took a deep breath and looked him directly in the eyes as if to give him the ok. He gave a barely visible nod, but she caught it and did the same.

Standing as close as they were, face-to-face, she felt his hard on. He put his hands on her ass and pulled her closer so there was no mistaking it. She unbuttoned the top button of his shirt with hands that were slightly shaky. His breath smelled like mint gum as it started to get heavier. Another button, then another. Then she felt the back of her shirt being lifted. Rick took off her shirt and bra and she stood there topless. She quickly undid the rest of the buttons on his shirt to reveal the ever present white t-shirt. He shirked off his dress shirt and in seconds had the t-shirt off as well. Still holding the shirts, he took her hand and led her into the living room where he tossed his shirts onto the back of an armchair. Standing in front of the couch, he unzipped her jeans and Bailey took the cue and kicked them off, underwear included.

“Sit. It’s your turn now, baby,” he said in a raspy voice.

Bailey obliged which wasn’t difficult given how weak her knees were anyway. He spread her knees apart and pulled her to the edge of the couch where he took one finger and touched her pussy and slowly pulled it away.

“My God, you are so wet,” he said as a trail of Bailey’s wetness stretched from his finger to her pussy. He took his finger and put it in his mouth. “Oh, God,” he moaned and stuck his finger back into her. Bailey arched her back at the feel of his touch inside her, as it only served to make her even more wet. She didn’t know how long she could go before she would be begging him to fuck her. Especially if he just kept toying with her like this.

She closed her eyes to the sensation of his finger going deep inside of her and soon he had two plunging into the depths of her tight pussy. Suddenly she felt his tongue slithering on her clit and she was writhing on the couch in pleasure. He took her whole clit on his mouth, sucking on it, nibbling on it and occasionally slipping his tongue into her pussy, but never letting his fingers come out. He kept fucking her with his fingers and using his tongue to bring her closer and closer to cumming.

“I want you to cum for me now,” he said authoritatively, his mouth speaking into her pussy.

She felt the vibration of his words as well as heard them and the command made her cum. She arched her back and forced her pussy into his face as she came while he still fucked her with his fingers. Her explosion was hard and while he was still eating her she came again, putting her heels on the edge of the couch and lifting herself into the air, screaming out loud with the force of the ecstasy that she felt.

When she came back to Earth, she sat upright on the couch and noticed that Rick was completely naked, his cock at full attention. She looked at it and licked her lips, but Rick cut her thoughts off. “Not this time. I have other plans.” He slowly turned Bailey over so she was face down on the couch with her knees on the floor. Rick came up behind her and folded himself over her, using his hand to play with her pussy once again. He used his left hand to cup and massage her left breast and pinched the nipple a few times. Whenever he did, Bailey cried out, but it was out of pleasure. A low, feral growl was building in her chest and she could feel an animal instinct coming on. She put her hands on the couch and lifted herself to give him better access to both her breasts.

A knee parted her legs, and soon a finger was inside her, rubbing her juices around, lubricating her ass. She started when a finger went into her ass.

“Shhhh. It’s ok. Have you ever been fucked in the ass before?” he whispered to her like she was a frightened child.

Bailey just shook her head. She had tried to do it once with an old boyfriend, but they weren’t successful, and all he ended up doing was hurting her, and she told him to stop. Thankfully he did.

“You will like it. And we will ease into it,” he continued to whisper. His finger continued to stroke her pussy and clit. A low thrumming was building in her, both from how he was rubbing her, and from the soothing way he was talking to her. He stopped massaging her breasts and nipples and she could tell that he had started stroking his cock and she turned her head so she could see him.

He gave her a little smile and said, “Ready?” and before she could answer, with a quick thrust he had sheathed himself inside her pussy to the hilt. She screamed as he grabbed a handful of her hair and immediately began pummeling her with his cock. Bailey tried to release herself from his hold just enough to be able to see him. She loved this position because it felt incredible, but she didn’t like that she couldn’t see his face. She liked to see every expression as it crossed his face.

As he continued to ram his cock in her pussy, she felt the buildup of an orgasm from deep inside. Every thrust that caused him to pull her hair made her scream out and made her get that much closer to bursting. Just as she felt herself on the brink, she felt his thumb massaging the outside of ass, which caused a weird sensation to run through her. She was a little frightened at first, but it quickly turned to pleasure and soon a finger found its way inside and just with that little change, she felt the eruption of pleasure and let her orgasm take over her senses. Rick slowed his thrusting for just a few seconds while Bailey let her muscles tense and relax from the amazing surge going through her body. In mere moments Rick picked up the pace again, but this time, he stuck his whole finger in her ass, and Bailey struggled a little.

“Shhh, it’s ok. You will enjoy this, just try it.” His words soothed over her and soon she was back under his hypnotic spell as he slipped another finger inside her. He continued fucking her, rocking her back and forth, while his fingers explored new territory, and Bailey tried to relax. Rick took his cock out of her pussy and got some of her cum juices and wiped them on his cock and stroked himself and got more juice and put them on her ass. He took the head of his cock and teased her ass with it; poking the head in and out just enough to let her know what was coming next.

“Let me know if I hurt you, I will stop,” he leaned down and whispered to Bailey.

As excited and horny as she was, she figured she was ready for it, “I will,” she huffed out. “Go for it, please, God, please, put it in.”

Rick gave a crooked smile at her eagerness and eased the head of his cock into her. She sucked in her breath and went up to her elbows on the couch. “It’s ok,” she said. He slid more of his cock into her tight ass, and closed his eye at how good she felt. Her ass squeezed his cock so tight and he just wanted to start ramming into her and fucking the shit out of her. Soon, she’d be ready in just a minute. He slowly backed out, then in a little more, back out, then in deeper. She gasped a few times, and he’d stop for a second until she nodded, which damn near killed him because he was almost ready to shoot his load right now.

He finally managed to get his cock in her ass all the way and by now it was stretched enough that she was ready to be fucked good. God, he wanted to fuck her so hard in the ass. He went a few more times slowly, mostly for his own benefit than hers so he wouldn’t cum the first time that he thrust all the way into her. He could tell that she was getting into it because she was squirming and moving around on his cock, finding the spots where it felt good. Hold on, baby, he thought. It’s all gonna feel good in a minute.

When the immediate threat of cumming in her ass had passed, he grabbed both ass cheeks, and started to slowly rock her back and forth on his cock. Fuck, it was going to be so hard not to cum right away, but he rocked her back and forth, and began to pick up the tempo, and soon had her slamming onto his cock. He had her screaming out and the second he felt her orgasm begin, he knew he could let loose and drilled his cock into her ass for one final stroke to send him over the edge. His cum shot into her ass in hot spurts as he made guttural noises of ecstasy. They were both shuddering from wild orgasms, as he withdrew from her and they collapsed on the couch.

Bailey had never experienced anything like that before in her life. There was sex, and there was screwing, but she just got her brains fucked out of her. Holy hell, Rick was a fuck god. She was still breathing hard, but a crooked smile crossed her face as she couldn’t hold back the image of a naked statue of Rick with a hard on cast in marble placed in some town square.

“What?” he asked, sitting up a little, but moving slowly, clearly exhausted. “What are you thinking? Or do I even want to know?” he asked cautiously with his eye growing large.

Breaking out in a full grin now, Bailey just answered, “Oh, I think I’ve found my cure for the week from hell.” She gave him a quick poke in his belly and seemingly rejuvenated jumped off the couch and went down the hall.

Rick continued to sprawl on the couch and closed his eyes thinking about this evening and wondering how it had all come about. Jesus, all he had done this morning was call to see if Bailey wanted a new price sheet! He never imagined the evening would end up like this. He could tell that Bailey Sinclair was going to keep him on his toes. Or knees, elbows, or anywhere she wanted, he thought with a smile.

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