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Lucky Bill

Category: Anal Sex
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He was forty-five, and she was 18, an obvious difference in age, but there were other factors contributing to the hardship of undertaking a romance. He was married with two daughters, one who was 18, and the other who was 16. The problem did not lay with them, but with the wife, who had fallen out of love with her husband a while ago. They were only staying together for the kids, and that was where it all started.

See, Bill, the husband, was a nice guy, a wonderfully good and honest man, who was the best Father that anyone could ask for. He was neither strict nor overbearing, and he loved his family very much, but he did want his wife very badly. They had been in love since high school, and she had stopped giving him what he wanted after an outing to the strip club had completely wiped out their anniversary and holiday sex. He felt like he was barren most days, and although he tried to get what he wanted from his wife, there was no end to the frustrations.

He spent more time than usual at strip clubs and with other women, but he would never cheat on his wife. That was something that he would not do to his girls. He did not want to be kicked out of his house, that he had bought, and fixed up, and had always been apart of. The daughters were grown, but he still had time to be with them before they completely moved out–then the divorce subject would definitely be broached in a serious manner. Even though he did not want his wife to leave him, he knew that once the girls were gone, then she would go with them.

It was a sad fact that led him to focus his frustrations and tensions in guns, television, war movies mostly, and his work, which was depressing. Eleven years at the grocery store, and still only a photo lab manager. It was insanity. He was supposed to do more with his life than eat, work, sleep, and do it the next day. There had to be something more in life than the mundane routine, than the everyday bickering, and constant make-do that made him want to lose control. His temper had risen to a level that could not be kept at bay, and he was no longer a friendly man, moreso cross and testy than wonderfully nice. It seemed as though the toll of being a deprived husband and a taken for granted father were two things that he could not be anymore. Where would Bill’s relief come from?

It came in the form of Angie Jefferson, the best friend of his eldest, Megan. She was the same age as Megan, 18, but she had a much more mature body than his daughter. Angie had breasts as large as honeydew melons, and an ass as round and tender like the one of Jennifer Lopez. It was divine when she came over. Her beach blonde hair so long and cute, and her breasts were always bouncing in the tank tops that she had to wear in the California heat. Her skirts were always a little short, revealing thighs of tan flesh and skin that was so tight over her muscles. It was obvious that she played sports, such as volleyball and basketball. He should know, since she had been in everything with his own daughter.

After she graduated, he fretted that he would never see the pretty face of Angie again. He was so used to seeing her around the house, that he never really considered losing the memory of her face, which would have been a disaster for the times when he allowed himself in the shower to gratify his desires. He pictured her fresh, hot face sucking on his deprived cock, letting his juices drip all over her face. It was a facial that he could never picture with his wife, as her own face had shriveled somewhat, but the look of Angie’s was so precious. She had bright green eyes, freckled bronze cheeks, and plump pouty lips.

Her own family life was a mystery to Bill. He knew that she didn’t have a father, and that her mother was somewhat of a crazy woman. Angie was always complaining about the way she treated her daughter. He always made several comments that she was welcome to their little home, even though they were not that rich. They had room, but of course, his wife was witchy about the whole situation. They had two daughters, they didn’t need one more, especially one that made everyone so happy like Angie. Megan was certainly happier when she was around, and Heather, his other daughter, got along great with the girl. And he, of course, well, Bill just wanted to finally get the chance to see her naked or feel her.

It was around the time that they were off from college, on winter break, and Angie spent almost every single night and day at their house. Bill left early from work, became much more personable when he knew she would be there. He talked to her like a Father, and she would giggle and joke that he should adopt her. He would ask her why, and she would roll her eyes dramatically, commenting about how her mother drives her crazy. Consoling her was easy, and it was always a running joke for her to call him ‘Dad’ like his own.

In the early hours of the morning, when most of the house was sleeping, except for himself, as he liked to sleep in the living room, he heard the door to his daughter’s room open. He thought nothing of it, seeing that the bathroom was right across from the hall, but as he turned to look back from the couch, he noticed the bright blonde head bobbing up and down as Angie walked to the bathroom. Licking over her lips, he turned back to the depressing and boring display of C-span, and then thoughts came over him of two voluptuous naked breasts, the smiling of Angie above, and the little pink panties that he had found of hers on the floor one day. They were satin and lace, and he could just picture them hugging tight to her sweet ass and pussy lips.

Bill had enough of waiting. He had enough of everything, and in the tumultuous moment between sanity and insanity, he pushed himself off of the couch and went down the hall. He opened the door of the bathroom to find Angie standing with her panties down and flushing the toilet. She opened her mouth to say ‘hey!’ or whatever to get him to shut the door, but he did not let her nude body leave his sight. Going in, he looked over her and then leaned down to give her a kiss, placing his hands on her head and holding her against him. She tasted sweet and warm, and his tongue swarmed her own, sucking on it and lifting her up by her naked ass with a squeeze and grab. His hands then moved to run between her legs and over her pussy, feeling her clit and wet pussy. Surprised, he continued to toy as she stood there taking it. Was she letting him or actually in shock? Ignoring the answers that could possibly be, he pressed on. He was taller than her, much taller, and wider as well, she was relatively small compared to him.

Gasping after they broke apart, Angie wiped her mouth and stared at him with wide frightened eyes. She was silent for a moment, and then stepped back to him, kissing him this time. She accepted him, and that was enough to let the hunger out, letting his hands roam over every part of her. Her own shook and were slightly chilled as they held his neck. Her lips struggled to keep up with his own, which were taking her forcefully to the edge. In their passion, he was afraid that the smack of their lips was loud, as the house really wasn’t that big, and so he drew away from her, bringing his hands up from her darling bottom and caressing the back of her head, running through her hair.

“We can’t do this right now,” he told her looking deep into her eyes with his own baby blues. She nodded in agreement and licked over her lips. He could tell that she was going to make a fine cumslut when given the chance. Nodding, he swallowed and leaned forward for another tender kiss, then stopped and stood. “Let’s do something tomorrow, I’ll give you a call, and in the mean time–keep this a secret.”

He left her in the bathroom, and he could not believe that he had did it. Bill only looked forward to the coming days when he could do more than kiss and feel a young body like hers.

Bill did not call her the next day, as he had to work all day and there was no way that he could get away. He decided he would call the next day on his lunch hour, and so he did. She answered not knowing who it was, and he did not need to explained as he talked. He knew that she knew it was him. They were to meet at a grungy cheap hotel later that evening. Angie was against it at first, but with persuasion, promises that he just wanted to talk and let everything out in the open, she conceded. It was set that he was going to go over his “Dad’s”, so he could go hunting the next day. His family thought nothing of it, except that it was on sudden notice, but he explained it was something he needed to do for himself.

That night, he watched her pull into the hotel, park outside the room or building that they were in. Angie wore a little low cut tank top with a jacket over herself, and then a pair of low rise flared jeans. Her sandals clicked on the pavement as she walked up and turned the knob. First, she looked around, and then they met eyes as he came out of the bathroom and cleared his throat. Giving a little wave, he gestured to the bureau and told her to put her stuff down, as she seemed to be taking off her jacket and had a purse with her.

Angie was breathtaking, as always, and with her hair up in the ponytail, her face was only accentuated more than usual. Slender neck, narrow tan shoulders, and a very dainty, delicate face of gorgeous proportions. She swallowed and leaned against the bureau with her hands and ass, giving him a look of intense anxiety. She was very nervous about this, and he could not say that he did not feel the same. He was a married man having relations with his daughter’s very young best friend. Even still, it was hard to keep his erection at bay, as he had been thinking about all the possibilities of that night. Considering that he was actually going to cheat on his wife and family, he hoped that she was as good as he had made her out to be.

“So…about last night…” Angie began, clasping her hands and fidgeting as she lifted her glittering pools to study his face. “I just don’t know what happened….I was…thinking that…”

“What’s it going to take for you to suck my cock, dear?” He stood up, pushing down his boxers and pulling up the undershirt, revealing the dick. Bill knew that he had told himself to take it slow, but he hadn’t brought her here to talk. Whatever she wanted, he would give it to her, even money.

Startled, Angie licked her lips nervously and brought her hand to rest at the back of her neck, rubbing and massaging while stammering to reply, but he was already there in front of her with his dick getting harder by merely stripping her clothes off with his eyes. Couldn’t she just let it go like last night? Yes, it had to be there. The problem was that she was so alert. They needed drinks, and he had brought alcohol. If it would help to get her loose, then he had the cure.

“Well just get comfortable, hon, you know…I’m not going to bite. I’m your ‘dad’, remember?” He spoke placidly, reaching to push a stray wisp of blonde out of her face. He bent down and kissed her softly, pulling her close within a few seconds and hotly wrapping her tongue up with his own. Her chest pounded against his with each frenching embrace that he delivered, and soon, he let the breathless girl go, watching her slyly. Backing up, he sat down and glanced up to her with a raised brow. “Come on, baby, suck this dick just for a little while. It’s been such a long time…”

Tempted, she stared at it and bit her lip in a debate between her mind and body. Finally, the body won, and she dropped to her knees, crawling forward with a smirk on her face as he watched in great approval.

“That’s it, baby, crawl to blow this dick off, mmm,” he groaned as she tilted her face up, getting right in between his parted legs. She started at the base and licked up, then back down, kissing and licking, sucking gently on the tip. Placing his hands on her head, he started to push his dick down into her mouth. He wanted her to open up and see the light, he had one million ways to get off, and this was just one them. Her mouth received him after a push that sent his dick to the back of her throat. She came up choking, and he pulled off, easing it back in after a second. He worked it in and out slowly, gathering that she didn’t suck a lot of cock as her eyes were misty with tears from trying not to gag.

“Yea, take that cock, like a good girl for her Daddy. Mhm, suck that, bitch. Ah, yeah,” Bill commented hoarsely, growing and growing with each thrust down into her throat. She deep throated well after a time of coaxing it in, and his dick had never felt better. The beautiful face of a young blonde was like something he could never get off from watching porn. The real thing was so much better. Chuckling as she drew off suddenly, sputtering and coughing, he realized that he had came somewhat in her mouth. “What? You don’t like to drink cum, baby? Come on, sweetie. It’s not that bad.”

“It’s just that I don’t do a lot of this, and I’ve never swallowed, and yea, I don’t know, I’m sorry,” Her replies were more like pants with slight tone, as the dick nestled in her hair and against her cheek. Angie seemed sorrowful that she could not suck him off properly, but he really didn’t mind. He didn’t let her in on that, rather not wanting to give up his control over the young doe, but instead, he wrapped his hand up in her hair and pulled up to his face. He gave her a kiss and steadied her between his legs.

Bill took each strap of her tank top and pulled it to tear apart. She let out a shout and tried to stop her, but he wouldn’t let her, holding her hands down with a taunting chuckle. “What, I’ll buy you a new one, I promise. I’m your Daddy now, honey…leave it up to me to say what you wear, okay?”

She pouted as Bill tossed the tatters down to the floor, staring up at the full breasts in the confines of her strapless black bra. He reached back and pulled on the back, watching it unsnap and release the mountains of milky glory. Her nipples were like pink quarters, titillated to the chill of nude air on them. Bill pushed his face between them and let their weight press on him as he pulled her to him with arms wrapped around her waist.

Her pants had been falling off her hips the whole time, and when he pushed down by his hands, they fell past her thighs and showed him the shaven box of her mound. He smirked and bit a the right tit, looking up into her eyes with a devilish hint. He sucked and rested his hands on her ass, gripped and spread them, feeling down her ass crack. Jumping as he played with her asshole, smacking him lightly and giggling, Angie shook her head. “No, no.”

“Mm, yes, yes, baby,” he retorted, pulling her down quickly and over his lap. “Don’t tell me no, Angie. I’ve been told that for too long.”

He spanked her good and hard relentlessly for a minute. Listening to her yelps and whimpers, he brought her up and looked at her red face. She opened her mouth to say something but the control over her was enough to shut her up. He simply forced her head down to his lap, stuffing her up with his cock in her mouth again. Pushing his finger to her asshole again, he pressed and felt her stiffen, the dick simply in her mouth. She wasn’t sucking or swallowing, like he wanted.

“If you do anything but suck on that cock, Angie, I’m going to rip this ass up, so get to work,” he commanded, meaning business as he circled the tight hole between her cheeks. He knew that she was frightened now, but she did as demanded from. Slurping better than she had before. There was no instance of teeth as she bobbed up and down to his liking. He had placed his hand on her head to keep the right pace, lifting up when she needed to breath or stop from gagging. His erection was growing fast, and through the trials of easing her up off of his dick and then pushing her down again, he wanted to cum finally. It came with an idea as he threw her off of his lap and onto the bed. He shoved her head down into the pillow, fighting against her to pull her ass up and spread her cheeks. With his knees on her calves, there was nothing she could do but shout and plead for him to stop, but he was mad with lust as he filled her ass crack with his semen. He watched with mounting desire as the white liquid streamed down over the little hams and plunging a finger into the asshole, he felt her muscles contract and tighten. Likewise, her breath hissed between her teeth and her back arched as he pumped the fingers in and out, getting it as loose as he could before stepping back and then thrusting forward with his incredulously engorged member.

The head slammed deep down over and over whilst he smacked her ass, beating her down with his dick and hand. Angie could barely fight him off with the large dick inside of her ass, pummeling the inside of her cavity with an inhumane ravenous satisfaction.

“Take that cock, bitch. God, yes, mmm, yea that’s it. I want you to scream, Angie. Haha, God yes, little one. You act like my fucking ho now to this dick in your ass. Haha.” He laughed with pleasure as he finished his orgasm off inside of her ass. He pulled out and flipped her around. Her eyes went wide as he pushed the dick into her mouth. “Clean that. Come on, I’m not done yet. Let’s go.”

She was sucking again, and every time she whimpered, it hummed against his dick. He loved it, sweeping her hair over his hands as both of them took hold of her and rocked her face up and down on his cock. It grew hard after a long 20 minutes of her continuously sucking, and he drew out of her, slapping her face a couple times with it as he laughed and watched her lay there in distress. Pressing the dick over her face, his balls hung on her chin and he told her to lick it. She did so, and he told her to kiss it, and she did so.

“Mmm, that’s so nice of you, Angie, to do this for me, to be what I need right now,” he said in a soothing voice, leaning down to kiss her lips sloppily. She didn’t pull away but her response was a little bit lifeless. “Aww, you’re tired?”

He lifted her bottom up and pushed her to twist at the hip so he could rub her ass while speaking so nicely to her. “Sore baby? Sorry I got a little powerful, but you know I love you, sweetheart. Mm, indeed I love those tits, too. How big are they?”

“36D,” she breathed out and brought her body back to lay flat on the bed, staring up at him as he held himself over her.

“You want me to cum again, honey?” He questioned. Bill had started jerking his cock while talking to her, trying to give her a little break in between his sexual take overs. She only moaned and nodded. Boy, she was a good little one. He groaned and let her replace his hand with hers, handling it with expertise as she worked her fingers up and down in a firm but gentle hold. His balls shook as she pulled and pushed, and he thought he would never cum, even though it felt wonderful. The orgasm cumming was a powerful one, and he groaned as it began to drizzle. She gasped and went to put it in her mouth, but before she could, it had sprayed on her forehead and cheeks, lips and then in her mouth. Bill pulled back, liking the display of cum on his new slut. “No, no, let me just…”

The cum spouted on her chest, long strands of it shooting all over her as she writhed trying to avoid the salty juices from getting in her face. She didn’t succeed as a shot landed right on her face, dripping down to her jaw. The gallon of cum spread everywhere as he massaged it into her breasts, giving it a nice glisten. “You’re a gorgeous cum-covered daughter.”

Spent, he lay down on his back and watched as she got up to go into the bathroom, emerging clean and wet a while later. Laying down with Bill, he wrapped his arms around the little darling and gave her a pop on the forehead. She purred in response, “I love you.”

“I know, but did you ever think we’d be doing this?” He asked, shaking his head as he stared up at the ceiling, sighing and holding his dick in his hand. He itched and rubbed before letting it go and placing his hands around her again, feeling her smooth silky skin. It was like being back in high school with her.

“No, this was like a fantasy of mine, but I never thought it would have happened or like it did. I mean, is this a one time thing?” Angie asked, reminding him so much of Megan, and the way she was always worrying about her reputation or whatever.

“No need to worry, honey. I’m going to be here for you, and we’ll do this as often as I can. I don’t get any from Martha anyway, so you’re going to be the only one pleasuring Daddy, k?” He squeezed her shoulders and kissed her lips tenderly. He was gaining another powerful urge to spank her again, but he held it back, thinking that he’d like to do something else with his new fucktoy. “So did you like anal, baby? I know how Megan and you always seem to be repulsed by it.”

“It hurt a lot, but I could get into it…maybe,” she answered tickling his side as she giggled and nuzzled her head against his chest.

“Like you need more time with the experience? Hmm…how about we do it again right now? I’ll be more gentle and accommodating. I know you’ll like it more the second time.” He had already begun to sit up, letting her lay there and ponder. She shrugged her shoulders and moved to sit up on her knees.

“Well, I need to get wet first, right? It would hurt less if we get it lubed or something.” She started looking around for something, but he already knew of what to do.

“Lay down on your back and spread your legs wide, cumslut,” he said this lovingly, a twinkle in his eye as he pulled her down by her ankles gently. She lowered and bent her legs at the knee and opened, revealing to him a most gorgeous pussy, fat lips, shaven and glistening with wetness. “Mmm..”

He took a hand and placed it on her pussy, rubbing the thumb in to separate, and then took it away, pushing on her inner thighs to spread out more. He then saw the hole of her pussy and even the bud of her clit, and he smirked, nudging his fingers in and around to rub and tease. The moans started up as he pumped one finger in and then slipped in another. She gushed and moaned for more. His middle, pointer, and then his ring finger shoved up into her, and gasping, she fucked his hand like it was a cock. She grew wild and loud, nasty as he slammed it into her with zealotry. Her ass gleamed after she soaked the sheets with her juices, and he patted the bottom of her ass that he could while she lay on his back, driven to crazed desire by his finger fucks. This dirty old man was loving every bit of the young girl’s pleasure, because he knew what he was getting in the end.

He brought her to lay on her stomach, with his fingers still buried inside and then rubbed her milk all over her ass, in between, and around her asshole. It was still sore as he touched it and she clenched up, but he probed with his middle and got her up on her hind legs and hands. She spread the ass as wide as she could, pushing the ripe flesh up into the air like an offering for the sex gods. He was just their deliverer.

Raising up, he stood and got over her with his legs apart. Removing the finger, he eased his cock down, feeling her stretch and quiver with the 9 inch cock swelling up inside the small hole and canal. He pulled back, and she groaned, breathing between her teeth and then releasing.

“Don’t squeeze,” he advised, holding her ass apart and leaning down for another slow thrust inward. “Just let it go in and out, baby. Mmm, feels good.”

Bill was enjoying this, liking anal was a challenge that most girls wouldn’t accept, and he was teaching her how. He had never had so much control over anyone or anything in his whole life, and here he was, telling a young girl how to get him off, how to take this dick into her sweet ass. It was a number on his mind, that all this time, this was what he had been missing.

Every thrust sped up the next, and after about 10 minutes of slow, passionate taking of her bottom, he began to feel the tension loosening. Her arms jiggled and smacked against his with every deep rogering he pounded in. He wasn’t going to go to town just yet, letting it continue to quicken naturally and gently. Looking at her face, he saw the streams of tears down her cheeks and her hands gripping the sheets, but she was moaning. He brought one of the hands away from groping her ass and pushed two fingers into her pussy. The rhythmic push and pull of both holes sent her into a flurry of spasms and uncontrollable rocking. Pretty soon, he was fucking her ass harder and faster, ramming it in and letting her take it. She did this well, just to his liking, and every penetration was another scream or hiss or wince, whatever position she took, he received it with a good smile and jerk. The cum spewed out of him and into her ass once more, gushing and squirting from her hole as it flowed in from the head of his dick. It grew even more slippery, and the last few moments of their anal were fast and precise thrusts in and out of the crack of her ass.

Drained, once more, he lay down behind her, with his dick on her ass and felt her squeeze and loosen as she tried to remain calm. He was going to fall asleep, and he didn’t want his dick to ever leave her body. She leaned forward and rocked on it for awhile, pleasuring him somewhat as he felt her bounce and cry out. Angie was doing it for him. Every time he groaned her name or said something dirty, she only bounced harder, even though he was limp. In his lap, she was like an animal, massaging his crotch with her ass and moaning as he played idly with her pussy. The rest of the night was just as such, a cockfest for Bill, something that he had never dreamed of, that Angie would have been the one to be there for him all night, whenever he needed a kiss, or a blow job, or a really good anal fuck.

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