Topic: Tims insecurity Part 1All characters and events in the following story and purely fictitious. Any likeness of or to a person/event is strictly coincidental. Aswell this is my first attempt at writing erotic material, so please feel free to leave comment good OR Tim was what many would call an outcast, at 18 he had few friends and never got invited to any of the group events at his age. Parties or kickbacks as many called them now never even mentioned him let alone wanted him there. In fact his best friend of all was probably his sister. Just turning thirteen they were better friends than most would expect. Tim wasn’t a ugly kid, though he was a little on the hefty side. His blonde hair and blue eyes did catch the attention of the girls at school. While many girls considered him cute, they stayed away because of his weight. They didn’t see it as a problem since he was sweet and teddy bear like to them, but they didn’t want to know what the kids at school would say if they became his girlfriend. Of course this meant the kids at school did all they could to make him miserable. His sister on the other hand was rather the opposite. At 18 she was what many considered hot. Long brown hair, tanned white skin and deep brown eyes combined with her C cups now just starting to overflow into D’s and her naturally round hips did little to help keep the boys away. Her social status though was lower than expected for a girl with her looks. She did her best to stay away from the social standard, keeping in her art classes and trying to keep tight in her circle of Growing up together made Tim and his sister Ashley bond well.
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Though having the occasional fight the worked well together. Ashley tried to boost her brothers confidence and help with the girls at school, and Tim used his size to protect his sister. One time in particular Tim came home to find a guy from school that had seemed rather nice pinning her on the couch trying to get her shirt off. Before the guy knew it he found himself out side their house with a broken nose and arm. Needless to say she never heard from him ever again. While she was happy inside she knew she was rather sad, while they both played the part of normal in everyday life. Both of them had a secret that not even each of them knew of each other. Now at the age of 18 and hearing so many stories from his friends and from other boys at school, Tim’s sex drive had gone into overdrive. Almost anything could give him a hard on that wouldn’t go away till he jacked off. His sister hid a feeling quite the same, while her older friend began to talk of touching boys and such she was beginning to think of sex constantly and the ache between her legs only went away when she touched it.
The problem for both of them only got worse when one day while he was home sick and everyone was out Tim had found a website he was able to get a name and password for and spent the entire take jacking off too it. A whole array of lewdness that he couldn’t get enough of. Needless to say, a week later when Ashley came down with the same symptoms as her brother she came upon the name and password he had saved to his computer and soon found herself unable to not touch herself. She found herself most interested in two things which were all over the website, the first thing they called ‘titty fucking’ she thought was interesting. When she first saw this she couldn’t stop staring at her own boobs, roughly the same size as some of the younger girls on the site the thought of a boy putting his thing between her boobs till he squirted his stuff on them made her so wet she ended up needing to change her panties.
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The second though she didn’t understand why she was so turned on by was called ‘anal sex’. Page after page of guys putting their cocks in a girls butt, at first she thought it was gross. But after watching a few videos it seemed the girls doing it really enjoyed it. Later that day after taking a shower she stared at her ass in the mirror and wondered to herself, would it feel good? Would a boy like putting his thing in her Of course Tim wanted to try it all, it all looked fun to him. Not having a single girlfriend ever though things looked grim, this maybe even sparked his sex drive to be stronger. It wasn’t until about a month later nearing the end of the school year that anything happened. It was a Wednesday and the school day had been particularly cruel to Tim, though no one had really picked on him that day he sat near the back of his science class. The teacher more or less droned on in a endless sermon about things so the kids often whispered back and forth. In front of him sat five girls, they were all best friends of course and talked about this or that. One of the girls, Sally, was a close friend to Ashley and as they talked Tim thought he would listen in to see what was the topic of her sister and friends. It turned out it was sex, more specifically boys and their ‘size’. Appearently Sally recently gave her first blowjob and enjoyed and felt the need to tell her friends here in class, the others though were more popular girls in school and from what they said were all more experienced than poor Sara, the leader of this group was the first to ask. “well how big was he?” Sally raised her fingers up to show the distance between. “Oh, he wasn’t very big now was he? I love my guys big, nice long dicks. Nothing is more fun than giving a BJ to a boy with a nice big one.
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” Sally looked down at the table a little. “Well… I liked it. I thought he was a nice size. ” Another girl in the group chimed in. “Oh honey that’s just cause you don’t know any better, I’ve been with a few guys and the bigger the better. Sucking or fucking. ” The girls in the group, all but Sally laughed. A fourth girl began “Shes right sweety, that boy is too small. You need to shop around like us, We’ve all got boyfriends and we all picked them by their size. I wont accept anything under this size. ” The girl then raised her hands to show the size but because of Tim’s angle couldn’t see it. The other girls nodded in agreement. “Yeah, that’s a decent size. ” Sally looked ashamed in a way and remained quiet for the rest of the class. It stuck in Tim’s mind the rest of the day what they talked about, it worried him slightly.
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It wasn’t till later after lunch though that it really bothered him. It seemed that during lunch that very day Sally broke up with her boyfriend, she wouldn’t tell him why and the guy seemed really upset about it but Tim knew exactly why. After that his heart wouldn’t stop pounding, girls already didn’t like him. Now he had to worry about his ‘size’? Anxiety was overwhelming him, by the days end the chance to be alone at home felt like escaping a POW camp. Ashley’s day was better buy not much, while the anxiety never happened to her. She had to deal with her friend Sally, after lunch Sally just cried and cried. Ashley tried to be there for her, but Sally wouldn’t say why she did. “But Sally I thought you really liked Chris! He was such a nice guy. ” Sally nodded. “He was… he is!” Ashley didn’t get it. “Then why did you do it?” Sally sniffled more. “Because he just wasn’t right for me!” Ashley rubbed her back a little. “But what about what you did with him a couple days ago? I thought you had fun with him and he was nice to you about it and… I mean doesn’t that kind of mean you should stay with him?” Sally just kept crying. “I did enjoy it… I just… now… things have changed and he just isn’t for me. ” Ashley tried the rest of the day to help her but found it futile.
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When Ashley got home she was exhausted, her parents weren’t due home till late and her brother wasn’t much of a problem when she needed peace. He wouldn’t probably just put on his headset and play video games. As she walked past him room though he laid on his bed in silence, staring at the ceiling. Her first instinct was to just go to her room, she was tired and while she did want to know what was wrong with him she was too tired to try and talk to him after everything she had gone through trying to help Sally. She did anyway though, knocking on his door frame he awoke from his trance and looked at her. “Oh, hey Ash I’m sorry were you saying something. ” She giggled “no not a thing so I guess that means you got a problem?” Tim got a uncomfortable look on his face. “Not exactly a problem… more of a worry. ” Ashley walked over and sat on the foot of his bed and patted his leg. “what is it? You can always talk to me. ” Tim shook his head. “Not this Ash, seriously it’s a personal thing.
” She got a puzzled look on her face. “Personal? Hell you talk to me about girls and such isn’t that personal?” He nodded “Yeah but, this is a personal guy thing. A personal guy worry.
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” He looked at her and sat up. “Listen… it really is… weird. It wasn’t a problem or a worry till today and… I don’t know. ” She scooted next to him and hugged him. “Com’on bro. You know you can talk to me, what happened today that now it’s a problem. ” Tim turns to his sister and tells her the story of Sally and the others. By the end Ashley looks rather angry. “Those fucking bitches! God damn it! I knew Sally wasn’t telling me something! She really liked him and because those bitches went and made her feel bad about his, emm, ‘thing’ she went and broke up with him!” Tim just looked at the floor. “I’m sorry Ash, I didn’t mean to upset you. But you asked. ” She looked at him kindly. “Oh Tim no no no, I’m not mad at you. It’s what they did, she liked him. And she told me she had fun with him and SHE liked his… ummm, well yeah she liked him.
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What does she care what those stupid sluts think!?” Tim just shook his head. “I don’t know, but she seemed really sad at the end of class. ” Ashley clenched her fists. “I don’t get it…” Tim looked at her with question. “What does she care what those girls think? If she’s happy with him and what he has it shouldn’t matter. Plus how does she know that those girls have any CLUE what they’re talking about?” Tim just shrugged and looked out the window of his room. “I just think it’s stupid, if a girl is happy with what her guy has why does she care what other girls say?. . . I bet those stupid girls just watched porn and based their ideas on the size of the guys in those!” Tim looked at her confused. “You mean the guys in those adult films aren’t what girls expect?” Ashley laughed loud at this. “Hell no, those guys are gross big when it comes to their… ummm, ‘cocks’. You know Michelle? Well she and her boyfriend had sex recently and he was only this big…” Holding up her hands to show him about five inches. “… and she loved it. She said it was even a little too big when they first started but she still loved every second of it.
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You know how much something that big would hurt?” Tim laughed. “No how much?” Ashley started laughing and lost herself in it without thinking “A whole fucking lot! I mean with two fingers I feel full so…” She caught herself and turned bright red. “Holy fuck!” She screamed and ran out of Tim’s room to her own. Slamming her door behind her she jumped face first onto her bed and screamed into the pillow. “Oh my god how could I fucking say that to my own brother!?”
Tim just sat there confused and found himself slightly aroused. Was she mad at him? Or what? He felt himself slightly embarrassed though by what she said as well. He wanted to go consol her but he felt it best to let it go and pretend it didn’t happen. Ashley on the other hand couldn’t feel more stupid about letting that slip. ‘Great Ash, you just told your brother straight out you finger fuck yourself. He’s going to think your some slutty deviant now or something. ’ As the night drew on though he never came to say anything to her, she didn’t know if it was because he couldn’t stand the sight of her now or if he was trying to not rub the situation further in. About an hour later the phone rang and Tim picked it up, a few minutes later she heard her brother yell “Hey Ash, mom and dad are staying out tonight, something about the weather where they are. ” Ash stayed silent and Tim went to his room, he started getting ready for bed, worried that his sister was mad at him. Just as he was about to take his boxers off his sister opened his door without knocking. “Hey Ash damn it!” Ashley closed the door “Fuck I’m so sorry!” Tim sat on the bed in his boxers.
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“It’s ok, I’m in my boxers you can come it, that was just close. ” Ashley didn’t say it but she wished silently she had come in a few seconds later. So she could have seen something more. Ashley walked into Tim’s room in her Pjs. A long shirt of his she stole some months ago and shorts, Tim had never noticed it before but for some reason tonight he noticed his sister had really big boobs. While she walked to sit he noticed how they shook and jiggled with every step. Sitting herself down next to him she patted his knee. “I’m sorry about freaking out earlier, I just. . . yeah so anyway, We never talked about your issue and why you were so upset. What was it?” Tim was distracted by her chest for a minute but snapped out of it as she finished the question and turned red. “Oh, it was nothing. ” She brought her arms together to try and act cute, what she didn’t realize was that that when she did it pressed her tits together swallowing her shirt into her cleavage. “Please tell me? I feel bad about just abandoning you when you had a problem.
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” Tim sat staring for a second and then took a deep breath. “Seriously Ash, I don’t think you can help me and this isn’t one of those things where talking will help. Unless I can get answers I won’t feel better and the only person that could give me an answer is a girl. ” She looked a little confused at her brother. “Uhh, hello? These aren’t fake you know?” Said pushing her tits together even more causing the shirt to strain against her nipples. Tim coughed as he caught his breath in his throat. “Oh yeah well… another girl. ” Ashley looked down and seemed sad. “Listen I know that I’m younger than you Tim. But if you need a girls help or anyone’s help I’m willing to try. ” Tim stared at his sister. “You promise not to be grossed out or pissed off with me?” She nodded to Tim slowly breathed in “well, after what I heard the girls in class say and talk about. You know about a guys ‘size’… I mean I can’t even get a girlfriend. What if someday I do and we get to that and she thinks I’m… small. ” Ashley pulled back a little from Tim, seeing his reaction on his face though she was quick to speak up.
“I’m not grossed out… or mad ok? I just don’t know what to say. ” It wasn’t until that moment that she really even thought about the fact that her brother was a boy and that meant her brother had a penis. She laughed to herself a little “I’m sure whatever you have is fine, I don’t know why boys and those girls make such a big deal. ” He shook his head. “How am I supposed to know that? If being ‘big’ makes a girl happy with a guy then I want to make sure that any girlfriend I have is happy with me. ” Ashley felt bad for him, she wanted to help him feel better and not so afraid of things. “Well…” An idea came to her head. She was interested in seeing a boys things, touching it. He wanted some assurance that he wasn’t deformed or what not, maybe she could kill two birds with one stone. She put her hand on his knee, touching his bare skin. “well… I am a girl you know. ” He nodded, her breathing had increased slightly making her chest even more noticed to him. Her being a girl was never more obvious to him than now. “Well… if you weren’t grossed out by it. I mean…” His impatience and need for answers pushed him to ask.
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“You mean what? What do you mean?!” He was desperate for any help his sister could give him. “Well. I mean… I’m a girl, so you could show it to me and I could tell you what I think?” There was silence, neither spoke for a long time. Just a long, unblinking stare between the two. She began to get up “Yeah it was a stupid idea I’m sorry-“ Tim took hold of her wrist and stopped her. “No, wait… I just, I don’t know how to react. I mean… I want you to so I can know but I mean. You’re my sister. Besides being wrong I know you love me and I don’t want you to be nice and tell me a lie just to make me feel better. ” She nodded. “I promise I Normally he would have sent her off, but between her long legs and massive chest the effect was swelling in his lower regions. She looked at him “So how do we do this?” He looked at her and shook his head. She stood up and dropped to her knees in front of him, the second she looked at his boxers she realized he was already hard. She hadn’t noticed before now. “ok… so you wanna pull it out for me so I can see?” She already could feel that warm tingly feeling in her puss again.
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The nagging ache that begged her to touch it, to rub it till her muscles tighten and her head fills with lights. “Are you sure about this Ash? I mean… what if I’m…” she rolled her eyes. “Silly, that’s why I’m doing this for you remember? To find out. ” He nodded his head and reached down to begin pushing down his boxers, as he did she scooted closer wanting a good view. As he pushed his boxers down he finally got them down far enough, his swollen member sprang out, the head hitting his sister in the face. “Oh my god I’m sorry Ash!” he said as he felt himself turn bright red.
She giggled in the most girly way he had ever heard her giggle. “It’s ok, my fault for being so close” she turned her attention back to the main event for her. “Oh wow Tim…” She trailed off as she stared, from the angle she was at she was sure he couldn’t see below her waist so she snuck a hand between her legs to gently rub her pussy though her shorts while she stares. “Wow. ” She said again in awe. Finally anxiety got the best of Tim. “Wow what1!? She recoiled back a little not expecting him to get to loud. “Sheesh calm down… It’s just… well… that’s big. ” Tim felt himself swell with embarrassment and pride.
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“Seriously?” she nodded. “Yeah, seriously. That’s big. I mean I think it is… have you ever measured it?” He shook his head, she pulled her now damp hand from between her legs and got up. “I’ll got get a ruler. ” She runs to her room and gets a standard ruler from her backpack and runs back dropping to her knees she looks at him with the sweetest smile she can muster. “Ok, here I got it… you mind if I… umm, touch it?” Unable to speak he merely shakes his head no. Slowly reaching out she wraps her fingers around the base and Tim breathes in sharply, She pulls back quickly “Did I hurt you?” Shaking his head “No no, it’s just remember what you’re touching. It just feels really good to be touched by a girl… if that grosses you out…” She shakes her head “No, I don’t mind making you feel good as long as you don’t care that it’s your little sister. ” She reaches back out and gets a good grip on him this time, she wants to make him gasp this time. Sliding her hand from the tip to the base she watches his eyes roll back as he doesn’t try to hide a moan. She takes the ruler and presses it against his length. “Hmm, wow. Well bro it looks like you’re a solid 7 inches. Actually just a hair over 7, like 1 tenth over.
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” Taking the ruler away she quickly pumps his shaft twice and then pulls her hand away and giggles trying to pretend she didn’t do anything. “Well… if you think that’s good. ” She nods quickly “Oh yes, VERY good. I think it’s more than a guy needs but it’s not scary so it’s good. ” Tim looks around a bit then at her. “Well thanks… I guess then…” Not wanting it to end Ashley quickly tries to think of something to stop him from putting it away. “Does it hurt?” she more or less blurts out. Tim shrugs “It’s uncomfortable. It aches something fierce but it doesn’t hurt like a bruise or a cut would. ” She slides her left hand down between her legs while she slides her right up his leg. She bites her bottom lip a little looking up at him. “Well… umm, you want me to help you with it?” Tim looks pressed for a decision, Ashley is quick to a solution. “Well… if it would help I could take off my shirt and you could look at my boobs. ” Tim looked at her chest. “Why?” she reached for the bottom of her shirt and stopped.
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“Well guys are constantly staring at my tits… and I know guys like tits. You’re a guy. So I figured you’d like my tits. ” Struck silent Tim just stares quietly at Ashley, watches her as she pulls her shirt up. Her large tits hang there pert with hard pink nipples, each nipple roughly half a inch long. As she bring her arms above her head to get the shirt off, it brings her tits high and together forming what Tim could only explain as perfect. Throwing her shirt to the side she brings her arms together in front of her and giggles, making her tits press together and jiggle. “good?” she asks with a devious smile. Her pussy is starting to take over, she wants to do SO much more than just touch it now. It isn’t her brother anymore, it’s a cock. A nice, beautiful cock that she wants to use as her play thing. Restraining herself she reaches back and wraps her hand around his shaft. “Ok. Now what?” He reaches down and wraps his hand around hers and starts to slowly sliding her hand up and down his hard dick. “Just… just like that.
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” Tim seems exasperated, having a hard time breathing and talking. Almost hypnotized by it she begins to slowly stroke his shaft up and down. “Wow… it’s so hot. Almost like it’s on fire or something, and so hard… yet some how it’s so soft. ” Continuously massaging up and down his shaft a tiny drop begins to form on the tip. “Oh, would you look at that I’m making my brother precum. ” Giggling softly she keeps stroking, now a little harder and faster. She begins to notice a grimace of pain on her brothers face. “What’s wrong?” He grabs her hand. “Sorry, it just hurts. The friction hurts, you can stop if you want. ” She shakes her head. “No I want to finish you so it doesn’t hurt anymore. ” Tim pulls her hand off. “Well then, umm.
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Spit in your hand or something. Just make sure it’s wet. ” She spits in her hand and starts stroking his shaft, again he begins moaning and wiggling under her grip on him. But before long it goes dry and shes hurting him again. Frustration is obvious on her face. “I’m sorry Ash, it just starts to hurt when it gets dry. ” While the first thought in her mind was if his dick was half as wet as her pussy this wouldn’t be a problem. Her second thought she went with. “Ok, I got an idea. Just don’t be grossed out ok?” He nodded. Before he could react his sister swallowed his throbbing dick half way. She seemed to gagged a little and pulled up, spitting on the head and again on the shaft. She then grabs his hard cock again and begins stroking fast and hard. “Oh fucking hell Ash. ” She smiles and almost purrs to him “Oh you like that? Like it when I suck your big dick and then stroke it nice and hard for you?” At this point Tim couldn’t hear her, but he was happy as hell he jacked off so much, other wise he would have cum before she had put it in her mouth.
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“Fuckin’ hell that is so good. Oh fuck… fuck oh fuck!” She quickly releases his cock and takes him back in her mouth, she slobbers over his swollen prick as much as she can and then pulls off and keeps stroking him. She realizes that he has a flavor, a slightly sweet flavor. She thinks it’s weird at first till she thinks about what it must be. His cum! Of course, but its supposed to be salty and nasty… his is sweet I don’t taste any salt. Tim falls back on his bed. “Oh fuck Ash I’m going to cum!” she gets on her knees and leans in, before he cums though she remembers how the guys in the porns cum and aims his dick down at her tits. “oh fuck here it comes!” The first shot is hard and goes straight onto her right nipples, the feeling makes her shiver as her sensitive nipples feel the hot splash of his cum on them. The second and third shot go right between her tits and begin to slowly slide down in between her tits. The fourth and fifth shots though tend to dribble out and on her hand. By now shes stopped stroking him and just keeps squeezing his shaft in her hands, squeezing everytime she feels his dick pulse in her hands. Tim slowly sits up from the daze “holy hell, that was amazing I’ve never cum that hard. ” She smiles at him wickedly. “Well I’m glad… I had fun. ” Tim finally notices his cum all over her tits.
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“OH shit I am so sorry Ash” she laughs “It’s ok, I have to take a shower and anyway I wanted you to cum on them. It’s hot you know?” Ashley looks at the clock in his room. “Oh fuck! It’s 12. We got to wake up in 7 hours for school! I’m going to shower and go to bed. You should too. Night. . oh and I’m assuming you won’t tell anyone?” Tim nods quickly and pulls his bed sheets up. “Of course! Thanks sis. ” She winks at him “You’re welcome… I enjoyed it. Maybe you can return the favor tomorrow?. . . ” He feels himself swell at the thought of returning the favor. “Id love too! Seriously though thanks again.
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She winks at him as she walks out of his room “Seriously bro… any time. ” She closes his door and he lays back and thinks over what just happened. What he doesn’t see is what she does after she leaves. Once in the bathroom with the shower turned on she begins rubbing the cum into her tits, she gets a little drop on her finger and brings it to her lips. She quickly licks it off to taste it. “hmm, it’s not bad at all. It’s strange, but it tastes kind of good” Once in the shower it takes her all of five seconds to get a finger into her clean shaven bald pussy and one grabbing on to a tit that is far too big for her hand. “Oh god… fucking hell. ” She slowly pumps her fingers in and out of her pussy, sliding her thumb over her swollen clit. “Oh god damn… fuck bro you have such a nice cock. ” She slowly pushes a second finger into her overly tight pussy and starts to use her spare fingers to rub her inflamed puffy pussy lips. “oh god… oh god… OH GOD!” She shudders as her legs give out and she falls to her knees in the shower, the whole time she keeps pumping her fingers in and out while pinching her nipple. “OH FucK!” She shakes as she cums hard all over her fingers, the warm fluid from her pussy covering her hand as she keeps fucking herself with her fingers. “Mmmmm, oh fuck…” she shakes a little before coming out of her high. “Oh god… next time I am getting that beautiful fucking cock in me I don’t care what I have to do.
” After the shower Ashley lays in bed unable to sleep… she can’t wait for after school tomorrow…
.
