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Red Marks The Spot

Category: Anal Sex
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Cassie had one hobby in the last six months and that was to place herself in Will’s path whenever humanly possible. She’d tried to make him jealous by showing up at social gatherings where she knew he would be. She hung all over her dates in front of him and she succeeded in scaring off several of his dates. The act was getting a little bit old.

So when Will unlocked the door of the condo his firm owned and found her curled up on the couch, he wasn’t really surprised. Her father warned him that she was planning on coming up to the mountains to entertain his client’s wife that weekend.

She’d built a fire. She cradled a glass of wine in one hand. A blanket covered her lap and a book was open beside her. Will doubted she had spent much time reading it. Cassie was intelligent enough to have read it. Will knew her attention span rarely lasted a book as thick as the one on the couch.

Will took the scene in and ignored her for the moment. He stashed his luggage in the room furthest from the one she had taken. When he came back into the room, he intended to question her about why she was there and put an end to her games once and for all.

Will was a partner in Cassie’s father’s firm. Her father promoted him two weeks after he had enough of Cassie and kicked her out of their apartment. She wanted a wedding and a husband that danced like a puppet on a string.

She was spoiled and she knew it. Cassie liked to push the envelope with everyone and everything. Will knew exactly how far he could push her back and enjoyed pushing her one inch past that limit whenever he could.

That was probably why she still wanted him. No one else in her life ever told her no. It was probably why her father made him a partner after he kicked out her. Will would have been fine just to leave it at that but he’d had had enough of her games.

Will sat beside her on the couch and tossed the book she’d been reading aside.

“Cass, what are you doing here?” He said.

“I’m here to help you out the with client. I’ll take his wife shopping and to the spa. You will have him all to yourself,” she said.

“There was really no need. Since when do you help with the firm anyway?” Will said.

“Well, that’s a fine thank you,” Cassie answered.

“Cass, this little act is not going to work, you know,” Will said.

“What do you mean?” Cassie said.

“Cass, I could have come here with a woman,” Will said.

“You are here with a woman, Will,” she said.

“Cassie.” Will said.

“What Will?” she asked.

“We’re not getting back together. You are wasting your time,” Will said.

“We’ll see, Will.” Cassie said.

Cassie tossed the blanket aside and stood up from the couch. She swayed over the to the fire and Will felt his mouth go a little dry.

He watched as she grabbed a fireplace poker and shifted the logs on the fire. After tossing another log into the fire, she seemed satisfied. Only Will was not satisfied at all.

He was, in fact, a little shocked. Although it was odd that Cassie actually knew how to tend a fire, that wasn’t what threw him. What really got his attention was the burgundy sweater that reached just to her hips but not far enough to cover the only other piece of clothing she was wearing, a pair of white thong underwear. He was absolutely sure of the color. He got a real good look at the white stripe up her crack when she bent over to pick up the log and toss it into the fire.

Until then, Will thought the only fire she had known how to make was the one in his pants. And she spent very little time tending that one when they had been together.

She’d snatched up her wine glass and was sipping it in front of the fire with her back to him. Her hair was down that night. It had gotten a lot longer since they’d broken up. He never noticed because she always had it up in some proper manner. Her hair was thick and reached about half-way down her back. She was one of those blonds that had hair two shades lighter than honey and creamy skin she protected from the sun at all costs.

Will walked over and stood behind her. He wrapped his arms around her holding her to him. To a casual observer, the embrace might have looked like that of a lover but in all actuality it was a captive embrace.

Will was the captor who intended to hold Cassie to some answers.

“What do you want Cassie?” Will demanded.

“Oh Will, you know what I want,” she answered.

“Yeah I do, but I thought I made it pretty clear we’re not going to go there again. I do not want to become Mr. Cassie, your puppet husband,” Will said.

“It doesn’t have to be that way,” she said.

“Oh yeah?” Will asked. “You say that but I’ve seen your sister and her husband. And we’ve been down that road Cass. Yes, you are an incredibly beautiful woman and yes, I still want you but it would just be sex. Would you stand for that? Could you?”

“That’s fine with me. I just want you. Any way that I can have you,” Cassie said. She leaned back into him.

“Any way?” Will asked.

“Oh yeah,” she said.

She stretched up on her tiptoes and ground her butt into his crotch. Will drew in a sharp breath. He wondered if he should hope that by her body language implied her actual intent or if she was just teasing him again.

“Let me make myself clear, you want me any way that you can have me.” Will asked her again.

“Yes,” Cassie said. She nodded and smiled at him over her shoulder.

“And just that. You will be happy with just that?” Will said. He wasn’t sure he believed what he was hearing.

“Yes Will,” she said. She turned around and faced him.

“Well, we’ll see about that. Let me know when you change your mind Cassie,” Will whispered to her lips.

He kissed her mouth hard. Then he grabbed her by the shoulders and pushed her in the direction of the floor.

“Get down on your knees,” Will said.

“What?” She looked up at him a little confused. “What for?”

He raised his eyebrows in a challenge. Cassie rolled her eyes at him and dropped to her knees. He put a hand on the back of her head and pulled her face to his crotch to give her an idea of what he wanted.

She grinned at him and unbuckled his belt. With her teeth, she yanked the snap his pants open and pulled the zipper down.

She pushed his pants down over his hips and to his knees. Her fingers crawled under the elastic band on his briefs and pulled them down to meet his pants at his knees.

She took his hard cock in her hand and led him to her mouth. Will watched his cock as her lips closed around the head. Her blue eyes looked up to him as she sucked more of him into her mouth.

Will held her head in his hands on either side of her face and guided his dick down her throat. She moaned and pushed a little against him but he ignored her. Her hair was silky soft on his hands as her mouth was around his cock.

Cassie found her rhythm, sucking and cradling his cock with her tongue and then alternately she lost it again. Cassie’s oral talents had never been anything to write home about.

She had always been more interested in teasing and flirting than actually delivering what her body language promised. She’d never willingly gave him head while they were together and he could not ever remember a time when she’d swallowed. Most women swallowed at the beginning of a relationship, at least. But not Cassie.

Even that night, Cassie’s blow job sucked. And not in the way he wanted it to. Will decided that it was time he shifted gears on her.

Will pulled her up to stand. She reached up on her tiptoes and kissed him. Her arms circled his neck. Will kissed her briefly and slipped out of her arms.

He kicked his pants and briefs off and went into his room and then to the kitchen. She heard the refrigerator door open and ice knocking against itself in the tray. He opened other cabinets. She picked up her wine glass and sipped. She smiled to herself and thought she finally had him where she wanted him. This smelled like a condom trip to her.

When he started back into the room, she turned to him.

“Stop. Turn and face the fire,” Will said.

“What?” she asked.

“I said face the fire. Do not look over at me. Look down into the fire.” Will said.

“Alrighty, then ” she snapped at him. She knew she sounded like a smart ass; it was something she prided herself on mastering.

Will came up behind her and covered her eyes with a sleep mask. He pulled her hair from one side of her neck and nipped at her earlobe. He kissed her neck, his mouth cold from his drink and his breath smelling of whiskey.

“You are so beautiful,” Will told her.

“Hmmm,” she smiled.

“And so spoiled,” Will’s tongue traced her ear. She smiled again.

“If I remember correctly, Will, you liked spoiling me,” she said.

She laughed from deep in her throat and licked her lips. She actually managed to sound proud about it, like she was taunting him.

“There is not much you can do about it at this point,” she said.

“No. But I can choose how I am going to spoil you.”

She felt him pull away. Will knelt down behind her. She heard the ice clink in his glass as he sipped his whiskey. She could feel the heat of his body behind her legs.

Will pushed the sweater up out of his way. The sweater had only covered about two thirds of her ass. She had dressed, or rather didn’t dress that way to tease him.

And it worked. The heart shaped globes peaking out from under the crimson sweater appeared even creamier in contrast to the sweater’s color. But what had inspired him to let her stay and not throw her out on her glorious ass was how her cheeks looked heavy, full and ripe falling out from under the edge her sweater.

If Will thought about it, he might have realized the time and effort she put into that ass. He had known Cassie for years. He’d lived with her for the better part of two of those years. She spent hours per week on the stair master and the leg press at the gym.

She spent an almost equal amount of time with her back to a full length mirror looking over her shoulder and lamenting over the round, full part of her ass that no leg press or stair master could defeat.

It was lost on both of them that the part she hated most about her rear end was the part that still kept him up a night. It was the part that brought him back for more, even though he had sworn off of her altogether.

Will’s hands slid up her legs to rest on each of her cheeks. He squeezed them, pushing them together and then pulling them apart.

“What??” Cassie started.

“Shhhhh…” Will answered.

He grabbed the thong underwear and peeled them down over her ass and down her legs. Then, he messaged the cheeks in circles, spreading her crack open and then squeezing her cheeks together again.

“Bend forward a little bit, Cassie.” Will told her.

Cassie tried to accommodate him by leaning forward at the waist slightly. Will was not impressed with her paltry effort.

“Hmm. I guess we’ll work up to that.” He said. When they’d broken up, their sex life had been a point of contention. She knew she’d been a little unwilling a lot of the time and she regretted that.

“Hey, I did what you said…” Cassie started to complain when his next action stopped her short. Will pulled her cheeks wide and buried his face in her crack.

His tongue was immediately on her asshole, probing gently and circling the outside rim.

“Aaahhhh… oh Will.” Cassie moaned. He’d never done anything like that to her before.

Will sucked at the skin around her ass, still not entering it. He licked her ass along the crack and took one cheek in his mouth and began to suck. He nipped and sucked on her right cheek where it curved into her crack. He sucked and pulled the skin into his mouth and grazing his teeth over it creating a red splotchy hickey on her butt just to the right of her pink little rosebud. He knew that she would have a very hard time hiding this at the spa the next day, or worse explaining it to his client’s wife.

He slipped one hand through her legs to stroke the folds of her pussy and begin fingering her. When he was satisfied with one side he settled on her puckered little hole again, poking it with his tongue and sucking all around it. She moaned at this and arched her back. This opened her a little to him. This was what he was looking for before when he asked to bend over.

He shifted his attention and gave her a matching hickey on her other cheek, to the other side of her puckered asshole

When he was satisfied with his work he pressed her cheeks together again. She had a red spot marking the spot where her asshole was nestled between her cheeks.

Will smiled to himself. Her ass was now like a painted target and Will intended to nail a bull’s eye before they slept that night.

“I am going to make your asshole as red as this hickey when I’m done fucking you,” he said. He realized after the words were out that he had not meant to say them out loud. The idea turned him on so much and that the words just slipped out.

“Oh Will, no!!” she said. “Not hickies. They’re so trashy.” Cassie sounded a truly disgusted.

She stepped out away from him and turned around.

“And not that, Will, ” she quietly added and pushed the mask up to her forehead. “We talked about this before. I don’t want you to fuck me there.”

Will rolled his eyes. That was just like Cassie to complain about the humidity but not the heat. She was so proper that the keeping him from giving her hickies was a priority over keeping him from ramming his cock into her virgin asshole.

“Cassie, you said you wanted me any way that you could have me.” Will reminded her.

“And you said to let you know when I changed my mind,” Cassie said. She took a step away from him and pulled her sweater down in vain.

“Fine. Then, get out.” Will said.

“What? Now?” Cassie said. She sounded a little alarmed.

“Yes. Now. But if you leave tonight, I am done with you. And I mean that,” Will said.

“But Will…” She whined.

“I mean it. I am tired of these games Cassie,” Will said. “And quit whining. I assure you, I have given you nothing to whine about tonight.”

She didn’t answer and turned her back on him. He sat back on his heels and watched her standing there in that sweater that came down just past her hickies. This was typical Cassie behavior. She’d been teasing him since he met her and he was sick of it.

“It looks like you have a decision to make, Cassie baby,” Will said. Will got up and took his drink and his pants with him to his bedroom.

Cassie appeared in the doorway a few minutes later. The sleep mask was still pushed up on her forehead, her arms crossed over her chest.

“Okay,” she said.

Will kept unpacking.

“Okay to what Cassie?” Will said.

“Okay to whatever you want, Will,” Cassie said.

“Whatever? That’s broad,” Will said.

“What do you want me to agree to?” Cassie said.

“Well, what do you want to agree to? I think I made it clear what I want. Some time ago. No more games and bullshit. I am tired of you showing up wherever I am at and teasing me. If we’re gonna fuck around Cass, we’re gonna fuck. MY way and your way. Whatever that is.”

“Okay,” she said a little shakily. “I want to stay. I want you, Will.”

Electricity shot through him. He knew it was hope and he wanted to hate that wild streak of weakness when it came to this woman. But he wasn’t going to admit it.

He’d wanted her spread open before him. Hell, he wanted her willing and unwilling. In his own way, he supposed that he actually loved her. But he wasn’t going to admit that either.

Cassie wrapped her arms around him from behind. He had his pants back on with his shirt untucked and his tie hanging loose around his neck.

“I am staying Will. Tell me what you want,” Cassie said.

He reached for his whiskey and finished it off and gave her a side-glance over his shoulder.

“Go over and get on the bed, Cassie.” He told her. He shook his head in the direction of the king sized bed.

She crawled onto the bed and sat there looking at him expectantly.

“Put the mask back on Cass.” He said. She did what he said.

“Take the sweater off and lay on your stomach with your head on one of the pillows,” Will told her.

Cassie pulled off the sweater and tossed it to the floor. She situated herself on her stomach in the center of the bed. He admired her bare ass in the air with the hickies marking his space in the center.

Will left her there. She heard him in the kitchen refilling his drink. Then she felt the bed shift under his weight. He straddled her legs and put his palms on her ass.

She could feel that he was naked. The hair on his legs was course and masculine against her smooth skin. When he shifted his position she could feel his balls on the backs of her legs.

He started on her ass where he had left off, deepening the red on each of her hickies. Then he quickly shifted to her puckered little opening.

He knew that she was a virgin back there. When they dated before, he’d wanted to take her there but she had always been adamantly against it.

Will sucked at the little wrinkles that joined in the center. He proceeded to attempt to trace each little wrinkle with his tongue to the apex. She started moaning at his administrations.

He spread her ass wider and shoved his face in her crack. He shook his head as if the action would allow him deeper access. Then, he straightened his tongue and started to penetrate her ass.

Cassie had always been a vocal lover. Even though this was new to her, her reaction was no different. She’d never had to ask Will to use his mouth to give her pleasure but this was entirely different.

She moaned and made little sighing sounds as he worked her over. She pushed her ass back to him and he felt her tight little muscle was as relaxed as it could be.

He slipped his hand under her and started to twirl a finger around her clit. Cassie’s fingers dug into the bedspread and she pushed her ass back against his mouth. She cried out Will’s name when she came with his fingers on her clit and his tongue pumping her ass.

Will crawled up beside her.

“You liked that. I know you did.” He whispered into her ear. She didn’t answer him.

“Cass. Tell me you liked it when you came and my mouth was on your ass.” He said.

“Yeah. I liked it. That was fucking amazing Will.” Cassie’s voice was quiet, breathless.

“You want me?” He asked.

“Well, YEAH,” She said with that smart ass tone in her voice.

“You want me to fuck you in the ass, don’t you Cassie?” Will said.

“Yes.” She said.

He was lying beside her when she felt his fingers smear something cool and wet around her asshole. Then his fingers were gone, only to return to work themselves and whatever he was using into her tight little hole.

She tried not to resist him but couldn’t help it to some extent. It hurt and well, fingers just didn’t normally go there. With the pain came the foreign sensation of being stretched where she was unused to it and excitement of his fingers invading her.

He kept cramming his fingers into her ass over and over again. She could feel a wetness that didn’t come from her in and around her ass. She knew he was putting something on her to make it easier for him to fuck her. Heat settled in her clit at the thought of being prepared for entry.

“What is that?” she asked. Her head was turned toward him, even though she couldn’t see anything. She felt his fingers on her lips.

“Taste them and find out.” Will said.

“Will!!” Your fingers have been… ” She couldn’t finish.

“They’ve been in your ass. If you want to know what I used to lube you up, then you need to suck my fingers.” Will said.

“But I…” she started and he pushed them into her mouth.

“Suck them Cassie,” he said.

She could hear how excited he was. His voice was thick and low. Cassie realized something that day. She liked the feeling of power that came over her when she knew how turned on Will at just the idea of doing the things they were contemplating. She touched her tongue to his fingers.

“Ever seen Last Tango in Paris, Cass?” He asked. Will’s voice got even lower.

She shook her head no and began to lick his fingers. They tasted like butter and something else, something sharper. She knew that was what her asshole tasted like to Will.

“Suck them clean Cass,” Will said. She cradled his fingers in her tongue and sucked.

He moaned. “Hold on Cass.”

He took back his fingers and moved away from her. She heard his glass tinkle. He was drinking. Then she felt something cold and wet at her asshole.

“Oh my… ugh.. ahh.” Cassie cried out. Will pressed an ice cube up into her ass.

“Hold it there Cassie baby,” Will said. “Let it melt inside you. Squeeze your ass around it while it melts. You’ll like it.”

The sensation and ice melting in her ass was like having to pee and not having to all at the same time. She felt like she did the moment before every orgasm when she never quite knew what to do with herself.

The ice was tightening her loose muscles and making her desperate for him to put his tongue or his fingers right back in there. She knew he was going to push his cock up into her. And now that she could really feel the spot where his cock would be, she wanted him to hurry.

“Will, fuck my ass. Please,” Cassie said. She arched her back and moved her butt a little as if beckoning to him, while still trying to hold onto the ice cube.

Now that she was asking him to do it, Will could barely make up his mind how he wanted to proceed.

He thought long and hard about what position he wanted her in when first entered her virgin ass. He knew he was going to start from behind, but he couldn’t decide if he wanted her flat on her stomach or kneeling with her legs and ass all spread for him.

He knew that it would hurt more the first way. She had been such a pain in his ass for such a long time. When he took aim at that target on her ass and fucked her little asshole, wanted to hurt her a little.

Will straddled her upper legs. He took his cock in his hand and coated it with butter. He would find some other lubricant for the rest of the weekend. He never dreamed she would let him do this and was caught completely unprepared. Ever since he had seen Last Tango when he was a teenager, he had wanted to do this to a woman.

He led his cock to the red spot on her cheeks. He split them with the rounded head of his cock and started to breach her ass.

Cassie cried out as he moved into her tight passage. He did not pause but kept a long straight path up her canal, right on target. As he got deeper inside her, he settled himself on her back and slid between her legs. When his cock was buried as much as the position allowed, he started to talk to her.

“Do you like it Cass?” Will said trying to keep control.

“Um, no.. yes… Ow. No.” Cassie moaned.

“Aww. Baby. But you feel so good,” Will said.

“Will, it hurts….” She whined.

“Give it a minute,” Will said. “You’ll get used to it, baby.”

“Oh,… ahh,” Cassie whined and whimpered.

Her ass felt full of his cock. He had completely replaced the itchy sensation of the ice cube. She gripped at him with her muscles, squeezing and releasing, trying to get comfortable with him lodged in her ass. The action was like an erotic tuning fork that resonated through her.

And those sounds poured out of Cassie’s mouth.

The constriction and her moaning drove Will to start pumping in and out.

“Ahhhh.” She whined.

“That’s it baby,” Will said. “Relax and fuck me back sugar.” She cried out more and moved with him.

“That’s it baby, fuck me with that ass. Let me hear you Cassie,” Will groaned.

“Ah ah ahh.,.. Will… Fuckkk.. ahhh,” she moaned.

“You like it baby. Admit it,” Will’s own voice was strained.

Will’s strokes quickened and he started to pick up the rhythm.

“Ugh.. ugh.. ugh…” Cassie grunted as she tried to meet him.

Will spread her legs wider.

“Pull your knees up a little baby,” Will said. “I’ll help you.”

He walked both of them up onto their knees while remaining deeply imbedded in her ass. Cassie got up on her elbows and Will pushed her knees up and apart so her ass was high and spread. This position allowed him deeper access and he sunk into his cock into her to the hilt.

“Ahhh…” Cassie said. “Is that it? Are you all the way in?”

“Oh yeah, Cass.” Will said.

Will started to fuck her again. His rhythm was hard and fast. Both of them were concentrating on the sensations and the sounds in the room dwindled down to the slapping thud of his balls and thighs against her thighs and pussy. When Cassie started to whine and cry out, Will egged her on.

“That’s it baby. I knew you would like this.” Will said.

As his fucked her ass harder, she had to brace herself and gave over to grunting. Will grasped her hips and stopped occasionally to see how red her ass was.

“It’s almost as red as the hickies, Cass.” Will told her as one point.

He would pull out of her and then enter her again. He wanted to keep doing it over and over again but the tight rim of her ass gripping the head of his cock almost made him cum. He had to hold back a couple times.

At one point, Will withdrew and pulled Cassie down in front of him and pulled off the mask. Spooning on their sides, he coached her to bend one leg at the knee.

He pulled her hand back and together they guided his cock back into her ass. He fucked her slowly and deeply, his finger on her clit, and her ass back up tight against his cock. She grasped backward to his hips to pull him in closer.

His thrusts were slow, deep and determined and Cassie found his rhythm and met him.

“Are you close?” Will asked, his words tight.

“Yeah. Oh yeah,” Cassie said.

“Cum now baby,” Will said. “Cum for me.”

When Will’s cock finally twitched in her backside and he cried out, Cassie’s own cries nearly drowned him out. Her head was thrown back on his shoulder when she came. Her focus was scattered between the instantaneous tightening of the muscles in her ass around his cock and the sensation of Will’s cock shooting cum in her ass.

Will had wanted her to cum as close to him as possible. He wanted her to associate a mind-blowing orgasm with his cock buried deep in her ass.

And that was exactly what Cassie thought of the next day after a half hour on the stair-master when she stood looking over her shoulder at her ass in the bathroom mirror. Her finger circled the hickies for all of three seconds before she was through the door looking for Will and another stick of butter.

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