Analternative (3-Pack Bundle) Read online

  Analternative

  By

  Saffron Daughter

  * * *

  Table of Contents:

  Trying Something New

  Girl In Control

  Neighbor in the Back

  About the Author

  Bonus Material 1 - Good Girl Bad Babysitter

  Bonus Material 2 - Caught Cheating

  Bonus Material 3 - My Sister's Boyfriend

  Non-Taboo Stories by Saffron Daughter

  Taboo Stories by Saffron Daughter

  License

  Trying Something New

  On the eve of Vanessa’s boyfriend’s birthday was when everything changed for Ralph. Well, everything might be overstating it a little. But to Ralph, caught in the throes of passion and its implication, it seemed like everything had changed.

  At the very least, his relationship with Vanessa, his best friend, the only person he really trusted, changed immeasurably.

  It all began with a single word: Anal.

  “Anal?” Ralph blurted out, unable to stop the wide and childish grin from pulling at his lips. “Are you serious?”

  “Yes, Ralph, I am serious.”

  “Wait, let me get this straight,” he said, his face bunching up tightly as if he was trying to decipher some alien code. “You want me to have sex with you… in the bum, so that you can go and have sex with your boyfriend… in the bum?”

  “Yes,” Vanessa said, nodding feverishly.

  “Okay, but why don’t you just cut out the middle man?” Ralph pointed at himself. “As in me, and go and just have anal sex with your boyfriend?”

  “Ralph, you’re so dimwitted, you know. I’ve never done it before.”

  “So?”

  “Tomorrow is his birthday.”

  “You’ve mentioned.”

  “So I want to give him a good present.”

  “And I’m sure he’ll like it!”

  “Yes, but I want it to be good!”

  “Oh, come on Van, you’re gorgeous.”

  “God, you’re thick. I need practice!”

  “Practice.”

  “Practice,” Vanessa said, punctuating it with a single nod of her head.

  “I… see,” Ralph replied, his face once again doing its best to imitate a prune. “Practice… to get… fucked up the bum?”

  “Yes.”

  “So, wait, why are you giving him practiced anal sex for his birthday?”

  “Well, he’s been asking for it for ages. He’s always touching me down there and licking—”

  “Woah, woah, let’s keep this PG-thirteen, yeah?”

  “Christ,” Vanessa said, rolling her eyes and slapping her thighs dramatically. “Anyway, I just feel like it would be a good time to give it to him.”

  “Well, technically he’d be giving it to you.” He erupted into a giggling splutter.

  “You’re so childish, Ralph.”

  “But seriously, Van, just because he wants it doesn’t mean you have to do it.”

  Vanessa’s lip curled wickedly. “Are you feeling… no, it couldn’t be! Concerned for me?”

  “No, I’m just saying—”

  “I know, Ralph. But, you know.” She shrugged. “Why not, right? I’m a bit curious.”

  “Curiosity killed the cat.”

  “I’ll kill you if you don’t start taking this seriously.”

  “Curiosity could hurt, you know.”

  “I know.”

  “Okay, so let’s go over this again,” Ralph said, still grinning. He could hardly believe this was real, that he was actually having a conversation like this, no less with Vanessa. God, how strange was this?

  “So you want me,” he continued, “to fuck you in your out-hole, so that you can practice for your boyfriend.”

  “Exactly.”

  “And how exactly will it be practice?”

  “Oh Jesus, Ralph. I just want to know what it feels like, and how to relax my bum muscles and stuff. You know, I don’t want it to be bad for him. It’s his birthday, and he’s wanted it for so long.”

  “Okay, okay, I get it,” Ralph said, holding his hands up as he sensed Vanessa’s patience eroding. “Um, I guess so?” He smiled searchingly at her, looking for any sign that she might not want to do it with him strictly. He might be the only option she had to practice with. A light bulb flicked on in his mind and held a finger up to silence Vanessa’s next words. “Wait, wait,” he said. “Why don’t you just try it with a dildo?”

  “I can’t fuck my ass with a dildo, Ralph.”

  “Why not?”

  “My arms aren’t long enough.”

  “What?!” Ralph said, bursting out into laughter. “How do you know?” His laughter stopped and his eyes widened. “Ah, I see.”

  “Yup. I just can’t push it in smoothly enough, or at the right angle.”

  “You know, you might be sitting in the wrong position or something. There are many ways to maximize—”

  “Ralph, Jesus, it’s not the same! I need to know what it feels like when he thrusts. He’s a… powerful love maker.”

  “Powerful eh?” Ralph said, grinning boyishly.

  “So, what do you say?” she asked, ignoring his childishness.

  “Um. Okay, I guess.” Ralph looked at his best friend quizzically for a moment, wondering why he was on such a high. He was teasing her, laughing at her, leading her on and generally being an annoying twit. The twitch he felt in his cock alerted him to it for the first time, and glancing at his own crotch, he was half-appalled and half-amused to find that he was sporting a semi. “Well, would you look at that,” he said, shaking his head and clucking his tongue. “I just can’t take you anywhere!”

  As Ralph stared at his own semi-rigid cock, it was as if a floodgate was opened. Memories came crashing through his consciousness. Him and Vanessa playing in the paddling pool together. Him and Vanessa playing football together, playing basketball together, playing table tennis together. Him and Vanessa going to school together, doing projects together, seeing movies together. He realized that she was almost more than a best friend. She was practically an extension of him. A twin, perhaps, born of a different mother and father.

  He tried to pull himself out of reverie but couldn’t. The thoughts of the past had ignited something else within him. He thought of the times they had play wrestled, when he had accidentally found his hand on her breast or her bum, or her inner thigh or around her navel. He thought of the times he had tickled her, and she him; when her hands had brushed past his groin, when they had held each other close, pushing their wriggling digits at each other…

  His heart skipped a beat, then jumped out of his chest, then plunged into his stomach where a hurricane was brewing. He gulped, before opening his mouth and saying: “Okay, okay. Let’s do it.”

  Vanessa smiled widely and looked into Ralph’s eyes. “Thank you,” she said, and Ralph smiled feebly back at her, feeling his face redden slightly.

  “Well,” he said, shakily. “Don’t ask me how I know, but I know we’ll need lubricant.”

  “You’ve done this before?”

  “Um, no, I’ve just watched lots of porn.”

  “Ah,” Vanessa said. “I see. Recently, so have I, actually.”

  “Good, we’re on the same page then.”

  “Indeed. And I made sure to prepare for tonight.” She bounced off the bed and retrieved a tube of lubricant from her bedside drawer. “Recommended for anal intercourse,” she read off the tube’s label.

  “Great,” Ralph said, feeling his cock twitch again.

  “Great,” Vanessa said.

  “Great,” Ralph echoed before suddenly erupting into a fit of nervous laughter. “So where di
d you buy that?” He imagined his best friend gingerly placing it on the counter, doing her best to look anywhere but in the eyes of the cashier.

  “Dundee’s Sex Shop on Acland.”

  “Oh yeah, I know it.”

  “You do?”

  “Yeah, never mind. Anyway, well, let’s get started.”

  “Right,” she said, “right. Getting started. I suppose that means taking off our clothes.”

  “Um, well, I guess. Not all of them, I suppose.”

  “Ralph, I wasn’t about to get naked in front of you.”

  “It’s not like I’d complain,” Ralph said genuinely.

  “Ralph…” Vanessa groaned. “Not now, please.”

  “Well go on then. Get undressed.”

  “Okay,” she said with a sigh, getting onto her knees on the bed and pointing her behind at her best friend. Slowly she eased down her skirt and her white panties with it, just far enough so that her anus came into view, but not far enough for Ralph to see her cunt. He gasped, feeling a violent surge in his sex. Her ass was immaculate, gorgeous, round and firm, each globe covered by smooth, unblemished skin. He stared at her entrance, devouring the sight of her wrinkled button, the skin slightly darker. He saw the small spots that were the tiny points of hair… so she’d just shaved.

  “Wow,” he let slip out of his mouth.

  “Thanks… I guess,” Vanessa said, looking over her shoulder. “Ready?”

  “Yeah, I think so,” Ralph said, fumbling a little. Now that the joking was over, he was beginning to feel a little scared. Had he showered that morning? He struggled to think when the last time he trimmed his pubic hair was. He gasped. What color underwear was he wearing? Stuff it, he thought. He positioned himself behind Vanessa on the bed and reached for the bottle of lube that had rolled to rest against the skin of her leg. “It’s going to be cold,” he said.

  “Yeah, that’s fine.” He noticed her voice was also a little shaky. So she was just as nervous as he was. A sudden thought struck him. Was this a good idea? Would this ruin their friendship?

  Would this release some hidden emotion or desire he harbored?

  Stuff it, he thought. Stuff it, stuff it… stuff her.

  He positioned the bottle an inch above the end of the cleft of her ass and squeezed out two generous dollops. They landed, wobbling like jelly, before they began to drip slowly down, a river of shiny lubricant running between her two glorious globes. He watched the jelly glide over her pucker, and he saw her squeeze and react to the cold.

  “It is cold,” she said, laughing nervously.

  “Yeah, I bet,” Ralph replied, feeling that it was something of an impotent remark. He fumbled at his belt buckle before finally getting it open, and unzipped his jeans and pulled them down in one ago, his purple boxer briefs coming down at the same moment. His cock came springing out, freed from the curled constriction it had faced in its underwear-imprisonment.

  “I’m going to have to rub it into you,” he said, wincing as he did so, wondering just how weird it would sound to her. Her best friend, and here he was saying he was going to have to push lubricant into her ass with his finger. Jesus, he thought, unable to contain the grin that grew on his face.

  “Okay, I’m going to put some on my finger and, uh, loosen you a little.”

  “Sure.”

  “Sure.” Ralph squeezed out another dollop of the lubricant onto his right hand and worked it in between his fingers until they were slick and slippery. He placed a finger gently at her entrance, feeling the textured skin, and Vanessa let out a low gasp, her head still and eyes fixed on the bed beneath her. He began to move his fingers in slow rhythmic circles, and his cock twitched violently, and he felt a faint surge of pain shoot through his pelvic muscle. He felt as if the skin around his shaft might split. He wondered at why he was so hard. Was it the anal sex? Or was it his best friend? Deep down, he knew the answer, but pushed it out of his consciousness. No, not now, Ralph, he thought. Now is not the time.

  Slowly, he began to apply pressure to her button, pressing harder and harder with each revolution, with each lap of the darker, wrinkled skin that funneled inward to her tight pucker. “Is everything okay?” he asked in a whisper.

  “Yes,” she said nearly breathlessly, and he noticed that his best friend’s breathing had quickened. She was nearly panting, her back heaving up and down quickly. Was she nervous or excited?

  Did it matter?

  “Um, okay, I’m going to push a finger inside you now,” he said gingerly.

  “Sure, sure,” she said hurriedly, waving her hand behind her as if to say he was in the driver’s seat now. He nodded, mostly for his own encouragement, before gently pressing harder with his finger, a firm and consistent force. The tip of his finger made its way inside, and he felt her resistance. She was tightening up, and her fingers clutching at the bed sheets only confirmed it.

  “You need to relax more,” he said. “You’re really tight.”

  “I am relaxing!”

  “No, you’re not. Trust me. Look, if we’re going to do this, you have to trust me, yeah?”

  “Okay, okay.”

  “Relax it. Let go. Don’t clench.” He felt her asshole loosen a little. “That’s right,” he said softly, nearly cooing. He pressed his finger in a little harder, and it began to slide inward. His nail bed disappeared into her hole, and he felt the tight ring clutching at his digit. He couldn’t help thinking how good this would feel on his cock…

  “Slower!” Vanessa said with a gasp, and Ralph immediately stopped pressing inward.

  “Sorry,” he offered, feeling that it was in vain.

  “No, no, it’s okay. Just… it feels weird.”

  “I bet,” he said before slowly restarting his exploration into her. He slid his finger fully in, slowly and, to his surprise, with little more resistance. As he pulled his finger out, Vanessa let out a soft sigh, and he wondered if she was feeling pleasure or if it was pain. Or perhaps it was both?

  “Okay, a few more times, yeah?”

  “Sure, okay.”

  “Okay.” He gathered more lubricant onto his finger from the area around her ass before pushing slowly back inside her again. This time she shivered strongly, and he saw goose bumps erupt on the sides of her thighs. “Are you okay?”

  “Fine, fine. Are you ready?”

  “What?” he said, distractedly. He was thrusting into her with his finger faster and harder, her inside already lubricated enough to allow his digit to move with little friction.

  “Are you hard?” she said a little impatiently before letting out a soft groan. It was only barely audible, but Ralph’s ears picked it up instantly, sending signals to his shaft to twitch powerfully once again, sending signals to his heart to try and pump more blood into his already turgid phallus.

  “Um,” he said, looking down at his aching cock. “Yeah, I think so.”

  Ralph gulped audibly and began to slowly pump his shaft, half with the aim of spreading the lubricant over his member, half with the aim of releasing some of the pent up pressure within it. Calm down, Ralph, he thought. Don’t get this all mixed up! She wants to practice for her boyfriend.

  Her boyfriend.

  Her fucking boyfriend!

  He gripped himself at his base and guided his glans to her entrance. The wide dome of his admittedly large cock pressed gently at her pucker, and he paused for a moment, looking at the back of his best friend’s head. He looked at her hair, cascading down either side of her face, fine and thin and shiny. He thought about grabbing a fistful of it and tugging hard, but recoiled in horror at his own lewd cognitions.

  What the fuck, Ralph. She’s your best friend! He yelled inwardly at himself.

  “Wait, Ralph,” she said, splitting the tension that had built between them cleanly in half.

  “Uh, yeah, Vanessa?” he said, painfully aware that his voice was hoarse and laced with lust.

  “This won’t change our friendship, will it?”

  “Isn’
t it a bit late for that?”

  “Will it?”

  “No,” Ralph promised, feeling his heart squirm painfully within him. “No, I promise.”

  “Good,” she said. “Proceed.” Ralph laughed lightly at her. What an odd thing so say.

  He pressed forward firmly, seeing her entrance stretch at his dome. He pushed but he wasn’t making any headway. The elastic ring of her ass seemed to be repelling him. He looked to the side and saw Vanessa’s fingers grasping tightly at the bed sheets. She looked either physically uncomfortable, or mentally uncomfortable, and Ralph couldn’t make up his mind on which one. While the former seemed more likely, the latter might mirror his own turbulent thoughts.

  “Try again,” she whispered at him, feeling that he’d stopped pushing.

  “Okay,” he said, pushing harder again. This time, she opened up, and the head of his cock slipped into her, her ring tightly ushering him inward until it clasped tightly around his shaft. He was inside her his entire glans, and he froze, feeling the periodic contractions of her ass around his cock. She gasped loudly, the tail-end of her vocal outburst graduating to a semi-moan.

  “Wow,” he said again, despite his previous conviction not to let slip anything else that might be revealing.

  “What?” Vanessa said, her voice suddenly imbued with alarm.

  “Oh, uh, nothing,” he lied. “It’s just, you’re really tight.” That was the truth, he thought.

  “It’s not too tight, is it?”

  “Are you kidding me?” he said with a laugh, instantly putting his hand to his face. “I mean, no it’s not too tight. Actually, I think your boyfriend is definitely going to enjoy this.” He felt his heart throb painfully.

  “Great, then,” she said. “Great.”

  “So, uh, do you want me to, you know, really fuck you? Like, hard? Like as if I would if I was actually doing this with my, uh, hypothetical girlfriend?”

  “Well, yeah.”

  “Are you sure?”

  “Well, I’ll never know how it feels—” she said, her voice trailing off and becoming a low grunt as his cock twitched powerfully within her. “I’ll never know how it feels,” she resumed, “if you don’t do it properly. I want to be ready for tomorrow.”