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 wasnât 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 didnât see it as a problem since he was sweet and teddy bear like to them, but they didnât 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 Dâs 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. 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, Timâs sex drive had gone into overdrive. Almost anything could give him a hard on that wouldnât 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 couldnât 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 âtitty fuckingâ she thought was interesting. When she first saw this she couldnât 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. The second though she didnât understand why she was so turned on by was called âanal sexâ. 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 wasnât 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 âsizeâ. 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. âwell how big was he?â Sally raised her fingers up to show the distance between. âOh, he wasnât 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.â Sally looked down at the table a little. âWell⊠I liked it. I thought he was a nice size.â Another girl in the group chimed in. âOh honey thatâs just cause you donât know any better, Iâve been with a few guys and the bigger the better. Sucking or fucking.â The girls in the group, all but Sally laughed. A fourth girl began âShes right sweety, that boy is too small. You need to shop around like us, Weâve all got boyfriends and we all picked them by their size. I wont accept anything under this size.â The girl then raised her hands to show the size but because of Timâs angle couldnât see it. The other girls nodded in agreement. âYeah, thatâs a decent size.â Sally looked ashamed in a way and remained quiet for the rest of the class. It stuck in Timâs mind the rest of the day what they talked about, it worried him slightly. It wasnât 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 wouldnât tell him why and the guy seemed really upset about it but Tim knew exactly why. After that his heart wouldnât stop pounding, girls already didnât like him. Now he had to worry about his âsizeâ? Anxiety was overwhelming him, by the days end the chance to be alone at home felt like escaping a POW camp. Ashleyâs 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 wouldnât say why she did. âBut Sally I thought you really liked Chris! He was such a nice guy.â Sally nodded. âHe was⊠he is!â Ashley didnât get it. âThen why did you do it?â Sally sniffled more. âBecause he just wasnât right for me!â Ashley rubbed her back a little. âBut 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 doesnât that kind of mean you should stay with him?â Sally just kept crying. âI did enjoy it⊠I just⊠now⊠things have changed and he just isnât for me.â Ashley tried the rest of the day to help her but found it futile. When Ashley got home she was exhausted, her parents werenât due home till late and her brother wasnât much of a problem when she needed peace. He wouldnât 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. âOh, hey Ash Iâm sorry were you saying something.â She giggled âno not a thing so I guess that means you got a problem?â Tim got a uncomfortable look on his face. âNot exactly a problem⊠more of a worry.â Ashley walked over and sat on the foot of his bed and patted his leg. âwhat is it? You can always talk to me.â Tim shook his head. âNot this Ash, seriously itâs a personal thing.â She got a puzzled look on her face. âPersonal? Hell you talk to me about girls and such isnât that personal?â He nodded âYeah but, this is a personal guy thing. A personal guy worry.â He looked at her and sat up. âListen⊠it really is⊠weird. It wasnât a problem or a worry till today and⊠I donât know.â She scooted next to him and hugged him. âComâon bro. You know you can talk to me, what happened today that now itâs a problem.â Tim turns to his sister and tells her the story of Sally and the others. By the end Ashley looks rather angry. âThose fucking bitches! God damn it! I knew Sally wasnât telling me something! She really liked him and because those bitches went and made her feel bad about his, emm, âthingâ she went and broke up with him!â Tim just looked at the floor. âIâm sorry Ash, I didnât mean to upset you. But you asked.â She looked at him kindly. âOh Tim no no no, Iâm not mad at you. Itâs 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. What does she care what those stupid sluts think!?â Tim just shook his head. âI donât know, but she seemed really sad at the end of class.â Ashley clenched her fists. âI donât get itâŠâ Tim looked at her with question. âWhat does she care what those girls think? If sheâs happy with him and what he has it shouldnât matter. Plus how does she know that those girls have any CLUE what theyâre talking about?â Tim just shrugged and looked out the window of his room. âI just think itâs 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!â Tim looked at her confused. âYou mean the guys in those adult films arenât what girls expect?â Ashley laughed loud at this. âHell no, those guys are gross big when it comes to their⊠ummm, âcocksâ. You know Michelle? Well she and her boyfriend had sex recently and he was only this bigâŠâ Holding up her hands to show him about five inches. â⊠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. You know how much something that big would hurt?â Tim laughed. âNo how much?â Ashley started laughing and lost herself in it without thinking âA whole fucking lot! I mean with two fingers I feel full soâŠâ She caught herself and turned bright red. âHoly fuck!â She screamed and ran out of Timâs room to her own. Slamming her door behind her she jumped face first onto her bed and screamed into the pillow. âOh my god how could I fucking say that to my own brother!?â
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 didnât happen. Ashley on the other hand couldnât feel more stupid about letting that slip. âGreat Ash, you just told your brother straight out you finger fuck yourself. Heâs going to think your some slutty deviant now or something.â As the night drew on though he never came to say anything to her, she didnât know if it was because he couldnât 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 âHey Ash, mom and dad are staying out tonight, something about the weather where they are.â 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. âHey Ash damn it!â Ashley closed the door âFuck Iâm so sorry!â Tim sat on the bed in his boxers. âItâs ok, Iâm in my boxers you can come it, that was just close.â Ashley didnât say it but she wished silently she had come in a few seconds later. So she could have seen something more.    Ashley walked into Timâs 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. âIâm 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?â Tim was distracted by her chest for a minute but snapped out of it as she finished the question and turned red. âOh, it was nothing.â She brought her arms together to try and act cute, what she didnât realize was that that when she did it pressed her tits together swallowing her shirt into her cleavage. âPlease tell me? I feel bad about just abandoning you when you had a problem.â       Tim sat staring for a second and then took a deep breath. âSeriously Ash, I donât think you can help me and this isnât one of those things where talking will help. Unless I can get answers I wonât feel better and the only person that could give me an answer is a girl.â She looked a little confused at her brother. âUhh, hello? These arenât fake you know?â 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. âOh yeah well⊠another girl.â Ashley looked down and seemed sad. âListen I know that Iâm younger than you Tim. But if you need a girls help or anyoneâs help Iâm willing to try.â Tim stared at his sister. âYou promise not to be grossed out or pissed off with me?â She nodded to Tim slowly breathed in âwell, after what I heard the girls in class say and talk about. You know about a guys âsizeâ⊠I mean I canât even get a girlfriend. What if someday I do and we get to that and she thinks Iâm⊠small.â Ashley pulled back a little from Tim, seeing his reaction on his face though she was quick to speak up. âIâm not grossed out⊠or mad ok? I just donât know what to say.â It wasnât 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 âIâm sure whatever you have is fine, I donât know why boys and those girls make such a big deal.â He shook his head. âHow am I supposed to know that? If being âbigâ makes a girl happy with a guy then I want to make sure that any girlfriend I have is happy with me.â Ashley felt bad for him, she wanted to help him feel better and not so afraid of things. âWellâŠâ An idea came to her head. She was interested in seeing a boys things, touching it. He wanted some assurance that he wasnât deformed or what not, maybe she could kill two birds with one stone.   She put her hand on his knee, touching his bare skin. âwell⊠I am a girl you know.â 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. âWell⊠if you werenât grossed out by it. I meanâŠâ His impatience and need for answers pushed him to ask. âYou mean what? What do you mean?!â He was desperate for any help his sister could give him. âWell. I mean⊠Iâm a girl, so you could show it to me and I could tell you what I think?â There was silence, neither spoke for a long time. Just a long, unblinking stare between the two. She began to get up âYeah it was a stupid idea Iâm sorry-â Tim took hold of her wrist and stopped her. âNo, wait⊠I just, I donât know how to react. I mean⊠I want you to so I can know but I mean. Youâre my sister. Besides being wrong I know you love me and I donât want you to be nice and tell me a lie just to make me feel better.â She nodded. âI 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 âSo how do we do this?â 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 hadnât noticed before now. âok⊠so you wanna pull it out for me so I can see?â She already could feel that warm tingly feeling in her puss again. The nagging ache that begged her to touch it, to rub it till her muscles tighten and her head fills with lights. âAre you sure about this Ash? I mean⊠what if IâmâŠâ she rolled her eyes.
âSilly, thatâs why Iâm doing this for you remember? To find out.â 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. âOh my god Iâm sorry Ash!â he said as he felt himself turn bright red. She giggled in the most girly way he had ever heard her giggle. âItâs ok, my fault for being so closeâ she turned her attention back to the main event for her. âOh wow TimâŠâ She trailed off as she stared, from the angle she was at she was sure he couldnât see below her waist so she snuck a hand between her legs to gently rub her pussy though her shorts while she stares. âWow.â She said again in awe. Finally anxiety got the best of Tim. âWow what1!? She recoiled back a little not expecting him to get to loud. âSheesh calm down⊠Itâs just⊠well⊠thatâs big.â Tim felt himself swell with embarrassment and pride. âSeriously?â she nodded. âYeah, seriously. Thatâs big. I mean I think it is⊠have you ever measured it?â He shook his head, she pulled her now damp hand from between her legs and got up. âIâll got get a ruler.â 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. âOk, here I got it⊠you mind if I⊠umm, touch it?â 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 âDid I hurt you?â Shaking his head âNo no, itâs just remember what youâre touching. It just feels really good to be touched by a girl⊠if that grosses you outâŠâ She shakes her head âNo, I donât mind making you feel good as long as you donât care that itâs your little sister.â 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 doesnât try to hide a moan. She takes the ruler and presses it against his length. âHmm, wow. Well bro it looks like youâre a solid 7 inches. Actually just a hair over 7, like 1 tenth over.â Taking the ruler away she quickly pumps his shaft twice and then pulls her hand away and giggles trying to pretend she didnât do anything. âWell⊠if you think thatâs good.â She nods quickly âOh yes, VERY good. I think itâs more than a guy needs but itâs not scary so itâs good.â Tim looks around a bit then at her. âWell thanks⊠I guess thenâŠâ Not wanting it to end Ashley quickly tries to think of something to stop him from putting it away. âDoes it hurt?â she more or less blurts out. Tim shrugs âItâs uncomfortable. It aches something fierce but it doesnât hurt like a bruise or a cut would.â 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. âWell⊠umm, you want me to help you with it?â Tim looks pressed for a decision, Ashley is quick to a solution. âWell⊠if it would help I could take off my shirt and you could look at my boobs.â Tim looked at her chest. âWhy?â she reached for the bottom of her shirt and stopped. âWell guys are constantly staring at my tits⊠and I know guys like tits. Youâre a guy. So I figured youâd like my tits.â 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. âgood?â 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 isnât her brother anymore, itâs 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. âOk. Now what?â He reaches down and wraps his hand around hers and starts to slowly sliding her hand up and down his hard dick. âJust⊠just like that.â Tim seems exasperated, having a hard time breathing and talking.         Almost hypnotized by it she begins to slowly stroke his shaft up and down. âWow⊠itâs so hot. Almost like itâs on fire or something, and so hard⊠yet some how itâs so soft.â Continuously massaging up and down his shaft a tiny drop begins to form on the tip. âOh, would you look at that Iâm making my brother precum.â Giggling softly she keeps stroking, now a little harder and faster. She begins to notice a grimace of pain on her brothers face. âWhatâs wrong?â He grabs her hand. âSorry, it just hurts. The friction hurts, you can stop if you want.â She shakes her head. âNo I want to finish you so it doesnât hurt anymore.â Tim pulls her hand off. âWell then, umm. Spit in your hand or something. Just make sure itâs wet.â 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. âIâm sorry Ash, it just starts to hurt when it gets dry.â While the first thought in her mind was if his dick was half as wet as her pussy this wouldnât be a problem. Her second thought she went with. âOk, I got an idea. Just donât be grossed out ok?â 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. âOh fucking hell Ash.â She smiles and almost purrs to him âOh you like that? Like it when I suck your big dick and then stroke it nice and hard for you?â At this point Tim couldnât 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. âFuckinâ hell that is so good. Oh fuck⊠fuck oh fuck!â 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 itâs 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 donât taste any salt. Tim falls back on his bed. âOh fuck Ash Iâm going to cum!â 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. âoh fuck here it comes!â 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 âholy hell, that was amazing Iâve never cum that hard.â She smiles at him wickedly. âWell Iâm glad⊠I had fun.â Tim finally notices his cum all over her tits. âOH shit I am so sorry Ashâ she laughs âItâs ok, I have to take a shower and anyway I wanted you to cum on them. Itâs hot you know?â Ashley looks at the clock in his room. âOh fuck! Itâs 12. We got to wake up in 7 hours for school! Iâm going to shower and go to bed. You should too. Night.. oh and Iâm assuming you wonât tell anyone?â Tim nods quickly and pulls his bed sheets up. âOf course! Thanks sis.â She winks at him âYouâre welcome⊠I enjoyed it. Maybe you can return the favor tomorrow?...â He feels himself swell at the thought of returning the favor. âId love too! Seriously though thanks again. She winks at him as she walks out of his room âSeriously bro⊠any time.â She closes his door and he lays back and thinks over what just happened. What he doesnât 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. âhmm, itâs not bad at all. Itâs strange, but it tastes kind of goodâ 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. âOh god⊠fucking hell.â She slowly pumps her fingers in and out of her pussy, sliding her thumb over her swollen clit. âOh god damn⊠fuck bro you have such a nice cock.â 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. âoh god⊠oh god⊠OH GOD!â 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. âOH FucK!â 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. âMmmmm, oh fuckâŠâ she shakes a little before coming out of her high. âOh god⊠next time I am getting that beautiful fucking cock in me I donât care what I have to do.â After the shower Ashley lays in bed unable to sleep⊠she canât wait for after school tomorrowâŠ
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