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Introduction:

Sorry for the delay with this chapter. No need to read the earlier chapters, but you may like them. After having sex with his stepmom and stepsister again, Tim has had a chance to recover a little, until a surprise visitor comes over. Read on and enjoy! Constructive criticism please.
After Tim's experience with his stepmom, then stepsister and stepmom at the same time, again. He didn't know how much longer he could keep this up. He wasn't about to complain about it, but both of the women in the house were wearing him ragged. He knew he had it better than any other guy his age, but was getting worn out.

It had been 5 days since the last experience, while both Kelly and Jenna flirted with him constantly, he still was trying to recover. It was early Monday afternoon, Kelly was off of work for the day. Tim was in the front room watching TV, while Kelly and Jenna had gone to the mall to shop. Kelly said that they probably wouldn't return until the evening. She had asked Tim if he wanted to go with, but he didn't accept the invitation, not wanting to spend the day at the mall with them.

Tim was laying on the couch, wearing a tank top and gym shorts, drifting in and out of sleep. As his eyes closed again, the doorbell rang, startling him awake. He got up off of the couch, walking to the front door, not realizing his dick was semi hard and forming a noticeable bulge in his shorts. He opened the door, wondering who it was.

Standing behind the door was a young girl. Tim looked at her, realizing it was Anna, one of Jenna's friends. He smiled at her, "hi Anna, can I help you?"

Anna is a few months younger than Jenna, and not as developed as Jenna. Anna stands about 5'4" with brown hair and blue eyes. Tim guessed she weighed 90 lbs., at the most, with maybe a B-cup chest. She was wearing a tight belly shirt and tiny jean shorts that barely covered her firm ass cheeks. Anna smiled shyly at Tim, as she nervously responded, "is your sister, Jenna home?" Tim shook his head, "no she's at the mall with her mom, she should be back this evening." Anna looked at him, disappointedly, "ah shucks, I was hoping her and I could hang out."

Tim looked at her sincerely, feeling his dick lightly twitch as he looked at her firm stomach. "Well I can let her know that you stopped by," he said, ready to close the door. Anna noticed the bulge in his shorts, then looked at him innocently, "well can I just come in and wait for her?" Tim started to shake his head, wanting to tell her he didn't think that was a good idea, but he went against his instinct and said, "ok I guess so, she should be home soon."

Anna smiled at him as she opened the screen door and walked in. Tim closed the door behind her, and led her to the front room. He plopped back onto the couch, laying down. He pointed at the recliner, saying, "you can sit there." Anna slowly walked over to the recliner, looking at him dejectedly, "ok, but I thought I would sit with you." Tim looked at her with surprise, as he watched her sit down, groaning to himself as she bent over slightly, before she sat down.

Tim then turned his attention back to the TV, again beginning to drift off to sleep, not paying any attention to Anna. Anna sat in the recliner, glancing over at Tim, every so often, wondering if what Jenna had told her was true about him.

Unbeknownst to Tim or Kelly, Jenna had told all of her friends about her stepbrother's huge dick. She had called all of them the day after she first had sex with him. She had talked to her friends before that day that she was going to find a way to have sex with him, and be the first of her friends to lose her virginity. All of them didn't believe that she could get her stepbrother to have sex with her, but after she did, and told them about how big he was, they all wanted to see it for themselves.

Anna sat there, remembering how Jenna had explained it to her. "Oh my god Anna, his thing is huge, no it's a monster," Jenna had said. Anna laughed to herself, just as she did when Jenna had told her that. She also remembered what Jenna had told her about how it felt to feel his dick inside of her. "It hurt a little at first, but after a while it felt good, and finally when I had my first orgasm, it felt, it felt totally incredible. Oh and when he shot his stuff inside of me, it felt warm, almost like he was peeing in me," Jenna had explained.

Anna had not come over just for that though, she had no idea Jenna wasn't home. She had just come to play with Jenna, and hoped she could get a chance to see Tim's dick before she left. But here she was, in their house, alone with Tim, but not knowing what to do, or how to get him to show her. She sat there, contemplating what to do, finally she broke the silence, bluntly spouting out, "Tim, can I see your huge thing?"

Tim jumped as Anna spoke, waking up and looking at her. Anna looked at him innocently, waiting for him to show her his dick. "What?" He asked, not sure what she meant. "Can I see your monster?" She asked, looking at him sincerely. Tim slowly sat up, looking at Anna in confusion, "my monster?" Anna quickly nodded, moving her feet under her in anticipation of him showing his dick to her. Tim still had a confused look on his face, asking, "what are you talking about?" Anna blinked her eyes quickly, surprised by his question, "yo... you know, your thing that you have sex with."

Tim almost burst out laughing ,realizing she meant his dick, but thought it was funny how she had said it. "Why do you wanna see that?" He asked, wondering what she was doing. Anna blushed innocently, getting more nervous now, "be... because I wanna see if what Jenna told me is true." Tim looked at her sternly, growing a little angry now, "wait a minute, Jenna told you about my dick?" Anna quickly nodded again, giggling at him saying, 'dick.' Tim was growing more angry now, not at Anna, but at Jenna, "what else did she tell you?"

Anna shifted nervously on the recliner, clearing her throat, "sh... she told me that you were the first person to have sex with her." Again Tim looked at her with surprise, Jenna had told Anna about them having sex, he wondered what else Jenna had said. He didn't ask her for anymore though, "so you want to see if it's true?" Anna eagerly nodded , hoping it was going to happen now. "How would you know if what she told you is true? Have you ever seen a guy's dick before?" Tim asked, slowly getting up from the couch.

Anna kept her eyes locked on him, slowly shaking her head, "well I did see my dad's when I was younger." Tim chuckled, "and what did you think of that?" Anna shrugged her shoulders, "I thought it just looked funny, because its not like my privates." Tim smiled devilishly at her, wondering what she would think of his then. "Ok well I'll show it to you, but you have to promise not to tell anyone," he said, looking at her sternly. Anna's face lit up, quickly nodding, "I promise Tim."

Tim let out a long breath, as he put his thumbs into the waistline of his shorts and boxers, "here goes nothing," he whispered under his breath. He slowly began to push his shorts down, Anna's widening as the shaft of his thick member was slowly revealed. As Tim pushed his shorts down to his mid-thighs, his semi-hard dick sprang up a little, causing Anna to gasp aloud, as she slowly began to move off of the chair. Tim chuckled when he heard her gasp, causing his dick to bounce a little, "are you ok Anna?"

Anna just stared at his dick, not saying anything, as she slowly moved towards him. Tim laughed to himself, as he watched her eyes cross, transfixed on his dick. Anna walked right up in front of him, still looking down at his dick. Tim could smell a sweet scent wafting from her, as his dick started to grow harder. She looked up at him, a look of shock on her face, "that is so much bigger than my dad's." Tim smiled slyly at her, "really, well you can touch it if you want," realizing he may have a chance to have sex with her.

Anna looked back down at his growing dick, slowly nodding, she covered her mouth to muffle a gasp, "its getting bigger." Tim lightly chuckled, "that's because he likes you, and wants you to touch him." Anna stared at it, watching his dick almost stand straight up in the air. Tim put a hand on her shoulder, whispering, "go ahead, touch him, it won't bite." He could feel her arm trembling, as he slowly moved his hand down the side of it, realizing she was probably nervous.

Anna slowly moved her hand out towards his dick, not knowing what to say or think about Tim's huge dick. 'It has to be twice as big as my dad's,' she thought, as she watched it throb in front of her. Tim looked down at her hand, inching towards him, slowly moving himself towards her, until her fingertips brushed against his shaft, causing him to groan and suck in his breath. Anna lightly ran her fingertips over his veiny shaft, marveling at how hard it looked, but soft to the touch.

"Oh yes, touch him, wrap your hand around him," Tim whispered with a groan, his legs beginning to shake in excitement, acting as if this was his first time again. Anna cooed, lightly running her fingertips up and down his shaft, feeling it throb against her touch. Tim pushed his hips towards her, wanting her to touch him more now, as he moved his hands to her lower back and rubbed down to her ass. Anna slowly wrapped her hand the shaft of his dick, looking up at him innocently, "well she was right, it is a monster, much bigger than my dad's."

Tim chuckled loudly, deciding this to go further now. "Well since you've seen mine, time for you to show me yours," he said, moving his hands to her hips and smiling at her. Anna looked up at him with fear, "I... I can't," she stuttered, moving her hand away from his dick. Tim took a step back, "what do you mean, you can't?" Anna held her head down, as if in shame, "m... my mom said it was wrong to show it to guys."

Tim was not about to let that fly, this little girl had just got him fully hard, and played with him a little. "Is your mom here right now?" He asked sarcastically. Anna looked up at him, slowly shaking her head, looking at him innocently. "So why can't you show me yours?" He asked, a little frustration in his voice. "Be... because she said I could get really sick if I did," she responded, tears welling up in eyes. Tim laughed heartily, "oh my fucking god, that has to be the most ridiculous thing I've ever heard." Anna laughed a little at his response. "Jenna told you what we did right?" Tim asked, hoping the answer was yes now. Anna slowly nodded, remaining silent. "See and she's not sick is she?" Tim said, hoping this worked.

Anna looked back down at his dick, then up at him, shaking her head. "So why can't I see your pussy?" He asked bluntly. Anna shrugged her shoulders, quietly saying, "I... I guess I could." Tim smiled wide, "yes you can," now the only thing on his mind was getting off. Tim sat down on the couch, slowly stroking his cock, "I'll sit here while you undress."

Anna nodded once, nervously fumbling with the button on her shorts, keeping her eyes focused on him. Tim smiled at her, ready to see her young pussy. She finally got her shorts unbuttoned, and began wiggling her hips around, trying to push them down. Tim focused his eyes on the prize, as Anna slowly pushed her shorts and panties down her legs, stopping at her knees and standing there in front of him. "Well, what do you think, are you happy now?" Anna asked, a little sarcasm in her voice.

Tim licked his lips as he stared at her hairless, 13 year old slit. He looked back up at her and smiled, "I think I need a closer look, come sit down over here," he said, patting a spot next to him. Anna nervously stood there, not sure if she should do what he wanted. "Come on Anna, I won't bite or tell anyone," Tim said, smiling. Anna hesitantly made her way over to the couch and sat down next to him. "Why are you so scared now, you weren't when I showed you my dick," Tim asked, noticing her nervousness.

Anna shrugged her shoulders slowly, "I guess because of what my mom told me about showing my privates to boys." Tim laughed again, "but your mom didn't say anything about a boy showing you his?" Anna shook her head quickly, looking down at his hand that was on her thigh, getting more nervous now. "Well just relax, nothing bad will happen from you showing me your pussy," Tim said softly, as he slowly started moving his hand up her thigh.

Anna's eyes darted between Tim's face and his hand moving closer to her pussy, her pussy beginning to tingle a little. Tim moved his head closer to her, his breath going into her ear, as his finger brushed against her pussy lip. Anna tried to pull away from him, not sure what was happening to her. "Shh it's ok Anna, just relax and do what feels natural to you," Tim groaned into her ear, taking her earlobe into his mouth and lightly nibbling at it.

Anna continued trying to pull away from Tim, as her body began to tingle all over, noticing her body temperature rising, her heart almost beating out of her chest. "What is happening to me?" Anna whispered, not trying to pull away anymore, and giving into him. Tim let go of her earlobe, whispering, "you're enjoying yourself, that's what." Tim put his middle finger in the middle of her slit, applying steady pressure as it opened and his finger went between her moistening folds.

Anna threw her head back, opening her mouth wide, as if to scream, but a moan was the only thing that escaped. Tim started kissing and nibbling at her neck, slowly moving his finger up and down her slit, feeling her legs jump and tremble, more and more, her breathing hastening. He continued to kiss at her neck, as tried to push the tip of his finger into her pussy, realizing that she was extremely tight. He groaned into her neck, her pussy denying his finger entry.

Tim moved away from her neck, wondering how he was going to get his dick inside of Anna, as he continued trying to push his finger into her. Anna opened her eyes and looked at him with lust now, "why did you stop?" Without saying a word, he moved his hand away from her pussy and slowly moved to the floor, and to his knees in front of her. Anna looked down at him, her pussy tingling even more, as she watched him grab her shorts and panties, pulling them the rest of the way off, and tossing them over his head. She locked her eyes on him, as Tim put his hands on her knees and spread her legs wide apart.

Tim glanced up at her, then back at her pussy, still trying to figure out how he was going to get inside of her extremely tight hole. He put a hand on her stomach, using his thumb and forefinger to spread her tiny pussy lips apart, and groaning at the sight of her pink insides, and her tiny pussy hole looking back at him. He again glanced up at her, Anna looking at him innocently, biting her lower lip. He smiled at her, then slowly moved his head towards her pussy, smelling her scent wafting from her pussy, causing his dick to throb.

Anna didn't know what to expect, as she watched him stick his tongue out, and felt the tip brush against her pussy, causing her to involuntarily tremble. She kept her eyes locked on him, as the tip of his tongue moved up her slit, flicking it across her swollen clit. Anna grabbed his head, her legs trembling violently, as felt pressure building up inside of her. Tim groaned, slightly in pain as her hands squeezed his ears tightly, continuing to flick his tongue against her clit.

Anna's body began to jerk and jump, as all kinds of new feelings ran over her. Tim tried pushing the middle finger of his other hand into her tight entrance, groaning as it slowly began to enter her. Anna threw her head back when she felt his finger begin to enter, moaning loudly, "wow, wow, wow." Her tight pussy sucked at his finger, as Tim tried to push it further into her, putting his mouth over her clit and sucking on it.

This put Anna over the edge, her hips moving forward hard, slamming her pussy against his mouth. A moan started low and gradually grew louder, as she experienced her first orgasm. Tim's finger was forced out of her pussy, as juices shot out, splashing against his chin and neck, soaking his shirt. Anna's hips bucked off of the couch, as she squeezed his head harder, enjoying the intense feeling of her first orgasm. Tim continued to suck on her clit, as her pussy expelled more juices out, completely drenching his shirt.

Anna's body fell limply onto the couch, her body still jerking and twitching as Tim sucked on her clit a little longer. As Tim moved his head away from her pussy, hisdick neck and chest glistening with her juices, she smiled at him, "what was that?" She asked, lightly moaning in pleasure. Tim lightly laughed, smiling at her, "you just came." Anna moaned again, "mmm, that was incredible, it felt like I had to pee, then this great pressure just left my body, followed by pure pleasure." Tim laughed again, kneeling up, taking his shirt off and looking down at his dick, sticking straight up in the air and precum oozing out of the tip. He looked back at Anna and smiled wide, "so are you ready to try what Jenna did?"

Anna's eyes widened as she looked up at him, "wh... what d... do you mean?" Tim sensed the nervousness in her voice, almost laughing at her, "you know what I mean, let me put my dick inside of you." Anna quickly shook her head, a look of fear coming across her face, "no, I... I can't." Tim's look quickly turned to disappointment, "why can't you, you're the one that started this, and it's not nice to tease." Anna looked down at his erection, stumbling out, "bu... but you're dick is so big, and I'm so small."

A smile crossed Tim's face, as he said, "that may be, but it fit in Jenna." Anna looked back up at him, the scared look still there, "I know Tim, but she's bigger than me." Tim was beginning to get frustrated now, "I tell you what, let me try putting it inside of you, and if you don't like it, I'll stop."

Anna looked at him, contemplating her options, she knew he had sex with Jenna, and Jenna said she loved it, but again her mind went back to what her mom had told her about sex. 'If you let a guy see your privates, or put his thing in there, it will cause you great pain and make you really sick,' her mom had said. She had no idea how ridiculous it really was, but believing her mom. The more she thought about it, the more she realized how ridiculous it was, 'I showed him my privates, and whatever he did to me, brought me great pleasure, and he did put it in Jenna,' she thought to herself, a smile crossing her face.

Anna looked at Tim again, "o... ok, but if it hurts, you had better stop." Tim nodded vigorously, his excitement growing now, "I promise Anna." Anna slowly nodded, looking down at his dick, as he grabbed it and lined it up with her slit. Tim slowly moved himself towards her, holding his dick steady as the tip began to split her labia, him taking deep breaths, trying to relax and not rush it. Anna was sitting up, watching her tiny lips being split apart by his fat head, taking quick, shallow breaths in anticipation of how it was going to feel.

Tim looked up at Anna, knowing she was scared, but remaining quiet. He looked back down at his dick, and slowly pushed forward, feeling her pussy begin to open and stretch around the head of his dick. Anna let out a long moan when she felt the head of his dick enter her, feeling a little uncomfortable now. Tim held steady, applying a little more pressure as his dick slowly sank into Anna's virgin pussy. He steadily pushed his dick into her until he felt some resistance, 'I can't be all the way inside of her,' he thought to himself, looking down and seeing well over half of his dick was still out of her.

Anna looked up at Tim, and moaned quietly, "holy shit," her pussy being stretched to its limit. Tim looked at her with concern, "ar... are you ok Anna?" Anna nodded, "yeah, but it feels so stretched down there." Tim lightly chuckled at her comment, and replied, "are you ready to experience your first fuck?" He groaned, feeling her pussy grasp and release the head of his dick. Anna again nodded, not sure what else she could say or do.

Tim put his hands on the couch, on either side of Anna's hips, ready to take her virginity. He took some deep breaths, surprised at how tight she was, and that his dick actually fit in her. He slowly began to withdraw, keeping his eyes locked on Anna's, as she looked at him with trust. Tim looked down at her pussy as he felt the air hit the glans of his head, staring at her pussy lips wrapped the head of his dick. He looked back up at Anna, swiftly moving his hips forward, the head of his dick ripping through her hymen, and slamming into her cervix.

As her cherry was ripped apart, Anna let out a blood curdling scream of pain, causing Tim to wince and look at her. "Take it out, it hurts, take it out," she yelled, tears rolling down her cheeks. Tim was frozen, not sure how to react, as he looked at her sincerely, "shh, it's ok, just try and relax." Anna shook her head vigorously, more tears rolling down her cheeks, "no, take it out, please stop." Anna had never felt so much pain before in her life. Tim's dick was making her feel so full, and stretching her pussy beyond its limit, she thought.

Tim had never broke a girl's cherry before, so her reaction took him by surprise. Tim decided to try moving in and out of her, maybe then she would relax. He slowly began to withdraw, looking down at his dick as he pulled out, noticing streaks of blood running along the shaft of his dick. He quickly looked up Anna, who had her eyes closed, her face cringing, as if she was in pain. Without saying anything to Anna, he looked back down as the glans of his dick appeared, Anna putting her hand on his stomach, trying to push him away. Tim grabbed her wrist, not about to stop now, as he slowly pushed his dick back into her until he pushed against her cervix again.

Anna opened her eyes, looking at him with a pleading look, "no please stop, you said you would." Remaining silent, Tim withdrew his dick again, until an inch of his dick was still inside of her, sweat beginning to run down his forehead. Anna struggled to free her hand, as Tim grunted, his dick throbbing inside of her, sending even more new sensations through her pussy. Anna finally gave up on trying to free herself, realizing Tim was much to strong for her, looking at him with a fearful look, but her pussy starting to relax now.

Tim smiled at her, "does it feel better now?" Anna shrugged her shoulders, "I don't know, it feels you're ripping my insides apart, but good at the same time." Tim laughed lightly, "I guarantee you I'm not." Anna smiled, lightly laughing as well, "ok, but it does hurt a little yet." Tim's look turned to concern, "well let me try moving in and out of you, then maybe it'll feel better." Anna nodded, looking at him sincerely.

Tim let out a long groan as he slowly pushed his dick back into her pussy, feeling her muscles quiver around it, as he buried himself inside of her again. Without pausing he slowly pulled back out of her, groaning louder at the sight of her pussy clinging to his blood streaked shaft. Just when the head of his dick was about to pull out of her, he looked at her and steadily pushed forward again. "Holy shit, she's so fucking tight," he groaned aloud, starting a steady rhythm of moving in and out of her clinging pussy. Anna moaned when she heard what he said, "I told you, I was small."

Tim started making animalistic noises, grunting and groaning, as he slowly picked up the pace on each stroke. Anna closed her eyes, starting to enjoy the feeling now, feeling the pressure begin build, just like it did earlier. Tim was moving in and out of her, almost as fast as he could, feeling his balls already pulling tight against him, knowing he was about to cum. Anna's hips were involuntarily moving into Tim, as the pressure continued to build higher. "Ohhh Tim, I feel the pressure building in me again, I think I'm gonna cum again," she moaned, meeting his thrusts harder each time.

Tim groaned when she announced that, "me too, your tight pussy is gonna make me cum." Anna felt his dick grow even bigger inside of her, being stretched even more. Tim threw his head back as he slammed into her hard, letting out a guttural groan, his dick throbbing hard as his virile seed rushed up his dick and fired into Anna's pussy, splashing against her cervix and filling her tight cavity immediately.

As Anna felt the first shot of Tim's cum spill into her, it set off her own orgasm, her pussy squeezing his dick hard, and pushing him back out of her. Tim groaned loudly as he felt his dick being pushed out of her pussy, trying to keep the head of his dick inside of her as it throbbed again and more cum shot out forcefully, and splashing back over the head, and dropping onto the floor. As Anna came, her pussy expelled more juices, just like earlier, but mixed with Tim's cum and her virginity blood, coating his dick and splashing against his abdomen.

Tim looked down as he felt her juices splash against him, just as his dick surged again, cum flying out and landing just above her slit, and drooping down over her gaping slit. Tim grabbed his dick, stroking it as it throbbed and jerked, more cum slowly oozing out and dripping onto Anna's gaping pussy.

Anna's body continued to jerk, as her orgasm began to fade, moaning and marveling at how hot his cum felt on her pussy. She smiled at Tim, laying back on the couch in exhaustion, "wow Tim, you were right, I did like that." Tim lightly laughed, leaning in and lightly kissing her on the lips, he pulled back and groaned, "I enjoyed it too."

Anna smiled wider, "when can we do it again?" Tim knelt back up, shrugging his shoulders, "not right now, I don't know when they'll be home, and I need a short break." He said, looking down at his limp dick, then at her cum covered, gaping and swollen pussy. Anna slowly sat up, looking down at her gaping slit, lightly touching it with her fingers, moaning, "I guess you're right, I'm a little sore. I'll just have to stay the night then."

Tim looked at her in shock, "st... stay the night?" Anna smiled at him, nodding, "yep so we can do it again." Tim sat back on his heels, a look of disbelief crossing his face.

Should I continue? Let me know what you think. Constructive criticism please.
91 comments

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anonymous readerReport

2013-09-26 16:56:52
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