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How Not to Major in Business

Category: Anal Sex
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Suzanne lay naked on her stomach across Tim’s bed with the top of her snorkel shoved in her ass. The rubber of the mouthpiece flopped in the air when she shifted her weight.

Tim climbed onto the bed beside her and propped his head on his hand. She was waking up from her nap. He had put her through a rough morning.

He ran his other hand down her back to rest over the crack of Suzanne’s upturned ass, the snorkel rising up between two of his fingers. He nudged it and asked, “Has it been in your ass the entire time?”

He was very close to her. Her face was turned toward him, her head in the crook of his elbow. She smelled like salt, sun and sex.

“Yes,” Suzanne’s eyed his face above her.

“Did you have to ask someone for help? Maybe one of your little friends from next door?” Tim said. His hand started to caress her ass, the snorkel’s mouthpiece jiggling with his movements.

“No. I used a door jam to shove it back in on my way in here but I didn’t touch it myself.” She answered him indignantly and then yawned.

“That really is too bad. I’m going to have to come up with a better type of humiliation for you then,” he said. Tim began to idly twist the snorkel back and forth but did not remove it. The tanning oil he used to lubricate its path that morning had long dried causing resistance and friction. He hoped it chafed.

Tim was considering the snorkel, Suzanne, and her ass.

Tim was staying in his company’s beach condo while he met some clients in town. After a long flight, he found himself ordered off his own property by the little blond thing before him. She’d told him her daddy would fire him if he didn’t get out.

After he stopped laughing, he set her straight. And he really would have fired her father in a New York second for handing out the keys to one of his company condos out to a bunch of college kids, if not for two reasons.

The first reason was she propositioned him on terms he couldn’t resist manipulating. It was almost too easy to turn the tables on her; she was really bad a bartering. He hoped she wasn’t a business major. And he really hoped she didn’t get her brains from her father.

The second reason was the girl was willing to do anything and she possessed one tight little virgin ass. And if Tim was anything, it was an ass man.

The only question for Tim was how long he would toy with her mind before he took the best part of what she had already bartered away for her daddy’s job and a week’s worth of free condo for Spring Break.

“You know what I really want to do?” He finally broke the silence.

“Hmmm. What?” Suzanne mumbled, still groggy from her nap.

“I want to fuck your ass.” His answer was flat.

Her anus tightened unconsciously on the snorkel. “Are you asking my permission?” Suzanne asked him. She sounded truly awake for the first time since he’d come in.

“Oh not at all. You know you gave me free reign. I am just getting you used to the idea…” Tim said and then continued. “It will hurt, you know. You’ve never had anything bigger than a finger in there until today, have you?”

Suzanne took a deep breath, “No.”

They were both quiet. Tim could feel his blood rushing in anticipation. And so could Suzanne… but she never would have admitted it.

“Will it really hurt?” Suzanne ventured.

“Oh yes. I will make sure it hurts.” Tim’s voice got a little deeper.

“When are you going to do it?” Suzanne asked and looked at his face.

He ignored her question and kept his eyes on her ass. His hand twisted the snorkel the whole time he talked to her about her ass. Her anus moved in turn. “Hmm. I want you to beg me to fuck your ass first.” Tim told her.

“Alrighty then.” Suzanne said in a tone that sounded more like “yeah right, you’re the only asshole in this equation.”

“You will beg me and you will mean it.” Tim looked down at her. He was surprised and pleased that she was going to buck him on this. It would make it more fun. He yanked the snorkel out and Suzanne winced. He tossed it across the room and pushed her over onto her back.

Tim kissed her earlobe and then her neck and trailed down to her breasts, taking each nipple in his mouth, holding it with his teeth and flicking it with his tongue. Suzanne dug her hands into his hair. If he kept this up, begging for it would be a very easy thing to do. His month continued over her stomach and over her public mound, his lips and tongue splitting her hairy cleft.

“Have you ever shaved your pubes Suzanne?” His tongue found her clit and started to roll it gently back and forth. Suzanne looked down at him, his mouth obscured in her hair.

“I shave my bikini line. I shaved all of it once and it itched when it grew back.” Suzanne’s last word was barely audible because Tim has begun to suck on her clit. His lifted her legs to drape over his arms and buried his hands under her ass. Each hand held a globe, four fingers lining her crack on each side. His hands began to massage and squeeze. He worked his fingers further into her cleft. As he tongued her clit, she lifted her ass to allow his hands better access. Tim couldn’t help thinking this girl was so easy.

“You are going to have to trim them, if nothing else. But most likely it will be a shaving,” Tim said up to her.

Suzanne’s eyelids fell and she experienced a strange sense of vertigo at the matter-of-fact manner in which he discussed her body. It was either that or his mouth had brought her to closer to an orgasm than she realized.

Tim’s tongue slipped down, lapped loudly in her juices and plunged into her. He tongue fucked her and squeezed her ass cheeks in the same rhythm. Suzanne’s moaning and heel digging signaled that she was getting close to orgasm.

Tim pulled a hand up and slipped his middle finger into her pussy and then down to her asshole. He repeated this, his fingers trailing her juices and his saliva to her asshole. His tongue licked a path from her pussy to her clit as he did this.

He pulled back and watched her face as he traced the outside of her puckered little asshole with his middle finger. The fingers of his other hand pulled apart her ass, as Tim’s finger slowly entered her.

He gently finger-fucked her ass and then worked his thumb into her pussy. He developed a rhythm, alternately fucking one hole and then the other with his thumb and finger. His bore down on her clit with his tongue and fingered her holes with blinding speed. He held her steady and as she racked against his mouth with her hips.

When she cried out and started to cum, Tim pulled his mouth back and rammed his finger deep into her ass. He wiggled his fingertip in her rectum and her ass clenched around his finger. He kept this up as he pulled her over onto her stomach with his free hand.

Suzanne ground her hips against Tim’s palm. His finger was pumping and wiggling in her ass, his thumb dipping occasionally into her pussy. She was still close to her orgasm and moaning. He smiled to himself at her desperate moves against his hand.

He told her to get up on her knees and elbows. He pulled her hips up to guide her with his free hand. Tim pulled his hand and finger away. Her ass felt unexpected empty where his finger had been. He pulled her knees apart so her ass was slightly spread and he could see her brown little bud peaking out.

Suzanne was in the same position as she had been the night before and was getting anxious. She wanted him to fuck her, not fuck with her.

“Alight, Suzanne. I want you to beg me to fuck you. I want you to beg me to fuck your virgin ass,” he said. “I want to hear your words and I want to see you beckon me with that sweet ass of yours.” He stood back from the bed, behind her.

Suzanne twisted a looked back at him over her shoulder. “Um. Fuck me, Tim.”

Tim crossed his arms against his chest. He was still fully clothed, aroused but clothed. “You will have to do a hell of a lot better than that.”

She tossed her hair and beseeched him with her eyes—which amused him. She was trying to find her confidence. She looked away from him. “Fuck my ass, Tim. Please.”

“Go on.” He answered.

“Please Tim. I want you to fuck my ass,” Suzanne looked back at him again.

“I might be starting to believe you. Tell me what you want me to do specifically. Tell me what you think it will feel like.” Tim offered her a lead.

“Um. I want you to fuck my asshole. I want to feel you in my ass,” Suzanne was starting to get frustrated.

“And will it hurt?” Tim said and waited.

“Yes, I think it will hurt.” Suzanne’s voice got a little deeper.

“Does that scare you?” Tim asked.

“Yeah, it does.” Suzanne’s head fell forward, away from him.

“And does that turn you on?” Tim’s voice was intense.

“I think. Yeah, it does.” Her answer was very quiet.

“That’s even more scary than the thought that it might hurt, isn’t it?” Tim asked her.

She didn’t answer. “Tell me what you want,” Tim demanded at her silence.

“I want you to fuck my ass with your big hot dick Tim.” Suzanne said in frustration. Tim smiled because she was getting pissed off.

“That’s sweet Suzanne. But I’m still not convinced. How about you invite me with your ass to fuck you? I want you to wave your ass behind you and beg me to fuck you,” Tim said.

Suzanne arched her back and stretched her ass back toward him. “Tim—please fuck me.” He did not answer her. She pulled her knees together and rocked back and forth. When she pushed her ass back her asshole winked out at him and then disappeared as she moved her body away.

“Oh Tim, I want you in my ass,” Suzanne moaned. She waved her ass from side to side.

“Now you’re on the right track Suzanne,” Tim said, his voice and his cock thickening.

“Please fuck my ass. Please. I want you in my ass so badly,” she begged. She raised her ass higher and higher. “Please Tim. Fuck my ass. I’ve never had a man in my ass before and I want you there. Soon.” Suzanne’s words and silky movements were starting to get to her.

And they were getting to Tim as well. He tossed off his shirt and pulled his shorts and briefs down. His dick was standing hard, tall and ready.

“More Suzanne. Where do you want me?” Tim asked her.

Suzanne let her shoulders and chest fall flush against the bed. Her hands crept back to her ass and she pulled her cheeks apart to show him her asshole.

“Please, please Tim. I am begging you, please. Fuck me here. “ One of her fingers grazed her asshole. “I want you here in my ass,” Suzanne pleaded.

Tim stepped forward at that moment. “Yes. Oh god yes. That is exactly what I want.”

He climbed on the bed behind her and trapped her legs between his. His thighs pressed up against the back of hers.

“Keep your hands right where they are.” He covered her fingers with his. “Spread your ass wider Suz.” He pulled her cheeks further apart and she held them open. Her little asshole was stretched and winking up at him. He spit on his fingers and rubbed the saliva into her asshole, around the edges.

Tim wanted to make a production of lubing her up but intentionally did it ineffectively. The friction would wear off his saliva quickly and then it would burn. And he wanted it to burn. The head of Tim’ dick rested on her little brown asshole. He slipped his cock down and slid into Suzanne’s dripping pussy. Suzanne moaned and he heard her making soft satisfied sounds as he slipped in and out of her. He plunged into her pussy once, twice, a third time before he pulled out and positioned at her asshole again.

“Tell me Suzanne. What do you want?” Tim asked.

“I want you in my ass.” She answered into the bed.

“What?” Tim demanded and pulled her head back by her long blond hair.

She turned her head to the side. “Fuck me. Fuck my ass, Tim.” She pushed her ass back towards him.

“Alright.” Tim pushed the head against her sphincter muscle. Suzanne was trying to find a way to tolerate him entering her ass. Tim knew what to tell her to make it easy for her but said nothing. Instead, he pushed relentlessly forward. He broke through her sphincter to the sound of Suzanne crying out.

“Ugh. Ugh. Ahhh.” She pulled her hands away from her ass and started to mewl. Tim felt her moving away from him. He grabbed her hips to stop her from crawling away from him.

Tim was unsure for the first time since last night when Suzanne stretched like a cat in heat on his bed and offered him anything, begging him to fuck her anywhere he wanted. He paused and asked, “Is this still what you want? Do you want me in your ass?”

“Nooooo.“ Suzanne whimpered.

Tim was stunned and a little incredulous that she might be backing out. “Really?”

Suzanne got up on her elbows as she answered after a silence and several deep breaths. “No, not really. I mean, yes, I still want it.”

Tim exhaled and started in on a slow path up her ass. Suzanne was trying to find a method to control and guide him but couldn’t center her muscles around him. The further he drove, the wider he got.

“Oh god…” she arched her back and then tried to move her hips forward and away.

Tim held her steady with hands on each side of her ass. He needed another strategy. He didn’t want her to back out. “Sshhhh baby. Move your hands back where they were. I want you to hold your ass wide open.”

She reached back again and pulled her cheeks apart. Tim moved his legs. “Now slowly spread your knees apart.” He guided her legs apart.

Tim inched into her a little more. “Half way, Suz. How does that feel baby?”

She moaned.

“Tell me. Tell me how it feels. Tell me what you want.“ Tim encouraged her.

“Oh god… Its huge.” Suzanne answered

He smiled. “Flattery doesn’t work on me, baby.”

“Hhurts,” she told him.

“Mmmm. Bad?” He took a deep breath. He wanted to move. He watched her dig her fingers into her ass.

“Not completely.” She was breathing hard. “Ugh. Umm, ok.”

“Do you want me to go deeper Suz? Beg me to drive deeper into you.” Tim asked before he pulled back and pushed into her, fucking her with half his dick. He reached under her and found her clit. He rolled it around between his finger and thumb.

“Ugh… Tim. Deeper… I want you to fuck me… more.” Suzanne was moving with him. The movement was loosening her muscles. Tim drove in a little further and then fucked her ass slowly.

“Oh yeah,” Suzanne moaned, getting turned on. She started to repeat herself. “Oh yeah. Fuck my ass Tim. I want you deep inside. I want your balls to beat up against my stomach.” Suzanne rotated her hips a little.

Tim pulled out at her actions. He decided he’d coddled her enough. She moaned a little in protest when he stopped rubbing her clit. He abruptly entered her again and pulled out. The shock and slight pain made her cry out. He pulled out entered her over and over again, driving them both. Her tight ass raked the sensitive head of his cock. Each breach made Suzanne whimper but was followed by a long, deep stroke that brought a series of guttural, satisfied moans from both of them.

Suzanne began leaning back into his strokes. Her movements soon became fevered. When Tim became unsure whether he was fucking her ass or if she was fucking his dick with her ass, he drove home and buried his dick buried to the hilt in her ass.

The momentum pushed Suzanne down flat onto the bed. Tim’s hips rested the backs of her hands. Her cheeks were still spread wide by her fingers. She was pinned under him and he rested between her spread legs. He began to rhythmically ground his hips into her ass. He started pumping her ass with short deep strokes which gave the effect of wedging himself further and further into her.

His lips were above her ear. “What does this feel like Suz?” Her head was turned and he could watch her profile. He was completely still, inside her.

“Oh god… It’s deep. Invading me. You are so huge. It feels like a log crammed up my ass.” She smiled a little.

“Do you like it?” Tim breathed into her ear and began to rotate his hips in circles.

She hesitated and her answered was labored. “Um yeah…. Ugh… You know, I think…ahh I like it.

Tim paused and rotated his hips in the other direction. “How do you feel?”

“Powerless…. Hot. Ahhh..” Suzanne moaned and started to move her ass against him.

“You should because you are both.” He answered but he wasn’t so sure. She was definitely hot, but powerless was in question.

Tim shifted his weight a little and pulled out of her. He told her to get back on her knees and hold her cheeks apart but this time with her knees on the edge of the bed. He pushed her legs closer together so her ass would be higher.

He pulled her to the edge of the bed as he stood up. Tim covered her hands with his and kneaded her cheeks, pulling them apart and pushing them together. He guided his cock into her ass again and watched her red puckered asshole stretch around his cock and swallow it.

When he was imbedded in her ass again, he told her to move one of her hands and see if she could feel where they were joined. She had to readjust and reach between her legs. But Tim helped her by guiding her hand with his to where her ass was spread around him.

He pumped into her while her fingers grazed his cock moving in and out. She was quiet and finally said, “I wish I could see it.” She was lost in her own feelings and missed his sharp intake of air that drove him over the edge.

Tim wasn’t aware of her hand falling away when he started to fuck her ass in earnest. He pulled her hips up to meet him. Suzanne finally braced her forearms on the bed and used them to push her body back when he drove into her. His dick was a piston in and out of her ass and she couldn’t keep track of him. She had wanted to meet his strokes but it was too much for her.

The friction between dick and her asshole began to burn. Suzanne finally gave into him and braced her hips and elbows to bear the onslaught of his fucking. With grunts and moans, she let herself feel weak and wanting and was surprised when she felt an orgasm building. It might have been the combination of the sex sounds of his legs slapping against hers and their combined grunts. But she suspected it was giving into him.

Tim threw his head back and gripped her hips flush against hers. Suzanne’s orgasm started with flexing the muscles in her legs and finally culminated in her a series of waves flexing her asshole spread around Tim’s throbbing cock. And Tim finally came deep in her ass, spurting over and over, grunting and yelling her name as the vice effect of her orgasm gripped at his cock in her ass.

Tim pushed Suzanne flat to the bed again and rested on top of her until his breathing slowed. His dick buried deep in her ass, he whispered into her ear all the ways he was going to use her over the next week. And before he pulled his flaccid dick from her ass, Suzanne agreed to each and every deed.

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