Little Sisters Ch. 02: Bess's First Time

All parties involved in this story are 18 and over at the time of the story.

I want to first thank everyone for their comments and assure you I will take them into consideration as I go forward.

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While I may have started fooling around with Alex first we never really had a good relationship as brother and sister. She was always just my little sister that I tolerated because we were family. Don't get me wrong she wasn't a bad looking girl just our personalities didn't get along with each other.

Now for our baby sister Bess we always got along in fact it was rare to see one without the other when we were home. Bess is 5' 4" with long blonde hair, baby blue eyes, curves in all the right places, and 32D breast. In fact even before I had started fucking Alex and decided there wasn't anything wrong with fucking family I found I sometimes got an erection thinking about Bess. Bess always hung around with me no matter what I was doing when we were growing up which made her a bit of a tomboy but she always had my back.

So it was no surprise to find us wrestling around one afternoon in my bedroom when things took an unexpected turn in our relationship. The thing you need to understand is that even though I had been fucking Alex for awhile it had never occurred to me to try anything with Bess. Bess was my buddy my partner in crime the one I knew exactly where I stood with her and wasn't willing to risk our bond just to fuck even though I wanted to since the first time with Alex.

I reached to grab a hold of Bess so I could pick her up and body slam her when my hand slipped. Now we had been rough housing for awhile and we both were covered in layer of sweat. So that when my hand slipped it went right down her shorts into her panties and I got my first feel of her mound. I quickly dropped her on her feet pulling my hand out after getting a nice feel of Bess and then stepped back away from her.

That is when Bess gives me this shocked look and ask me "What do you think you are doing Joe? You shouldn't be touching your little sister like that or there!"

I answer her saying "It was an accident I would never do that to you on purpose Bess! I would never try to take advantage of you in any especially in a sexual nature." That is when I got the surprise of my life when Bess reached out and grabbed me without any warning.

I was startled and jumped asking her "Bess what do you think you are doing? It is just as wrong for you to touch me as it is for me to touch you."

To which she calmly responded "Just making us even Joe what is that not ok with you? Shouldn't I at least get to grab you just like you already did me?" It was only at this point did the idea of fucking Bess even enter my mind and as soon as it had it came with an incredible urge to make it happen.

So barely missing a beat I say "Weellll it isn't quite the same since my hand actually went down inside your pants and panties" trying to see how she would react. I figured depending on how she reacted I would know if it was possible to start something with her. Little did I know what exactly I was about to get myself into or what would become of us afterwards.

Bess cracks a grin and says "Like you would let me put my hand in your pants and grab your dick on purpose so I took what I could get by with." That is when I decided to see how far I could take things before she would get scared or think about it too much.

So I shut and locked my door then went back over to her and dropped my pants saying "Well it is only fair since I grabbed you and you should get to grab me with full contact." This really did surprise but I got to give her credit she recovered quickly.

It took her a few minutes of sitting there staring at my cock before she said "Are you serious or what? You can't seriously be offering to allow me to grab your cock just to make us even."

I simply said "Hey I am only trying to make us completely even but if you don't want to it is your choice it doesn't matter to me. But then again I guess if we are to go for a complete balance I should get to grab you through your pants but again only if you are interested in us being equal." This whole time she has not stopped staring at my now erect cock.

I stand there for a couple of minutes longer then say to Bess "So do we balance things or would you rather just go back to wrestling around I need an answer." The response I receive is her timidly taking a grip of my cock and stroking it while allowing me to start rubbing her pants covered mound. After us doing this for a little bit of time I say "I guess we are almost even now except you got to see me do I get to take a peek at you now."

Bess whispers barely audible "Do you really want to see your little sister's pussy? If you do then yes you can go ahead and take my shorts and panties off so you can get your peek. I just can't believe my older brother is allowing me to stroke his cock and wants to see my pussy. "

So I do and the whole time Bess is stroking my cock so as soon as I have them off I go back to rubbing her pussy. Finally Bess comes out of her shock and says "Now wait a minute you aren't supposed to be doing that again. In fact we shouldn't be doing this at all we are family which makes this wrong." She stops stroking my cock and I quit rubbing her pussy which is really wet now.

I then sit down on the bed beside her and tell her it is ok we didn't do anything wrong and that in fact I liked it but we would stop if she wanted. Bess looked and me and said that while it did feel nice and she also liked it that because she was my sister it was not something we should be doing with each other. I realized at that moment I could easily talk her into proceeding with things but if I did it the wrong way how it would affect Bess.

So I looked at her and said "Bess I Love You and you are my little sister I would never do anything to hurt you. That yes others might see what we had done as wrong and even bad but I didn't cause we were just having fun. That as long as we both agreed and enjoyed it then it was ok cause it wasn't like we were trying to start dating. We were just fooling around with one another. It is up to you though if you want we can stop and just go back to our normal afternoon or we can continue and see what happens and whether we enjoy this new game."

She takes a while to think about what I have said during which time I just sit beside her doing nothing letting her decide on her own. Finally she places her hand on my leg and says "Joe are you sure it's ok? I don't want anyone thinking I a slut or something like that and you are my brother and best friend. I did enjoy what we have already done and actually want to see about more I just don't know if it is ok if I do it with you. What do you think is it ok or do you think we should stop now?"

So I tell her first we should only stop if she doesn't want to continue and wasn't having fun. That we could take our time and if she wanted to stop at any point we would immediately cause I wouldn't harm her in any way. As for what others might think I wasn't going to tell anyone because whatever we decided to do would be between us and no one else's business.

Again she took her time and thought about what I had just told and what it meant. After a bit she started stroking my limp cock again so I began to play with her pussy. I could tell she still hadn't made her mind up so I took my time but did move things forward to the point I had removed her shirt and bra and was playing with her nipples.

It wasn't until I was massaging her breast in one hand and rubbing circles with my thumb around her clit that she moaned and I truly took over. I pushed her back on the bed legs hanging over the side spread slightly. I got on my knees in the floor and began to methodically eat her out during which time I continued to play with her breast. I was enjoying her taste as she lost all control and had an orgasm right on my face the first time I took her engorged clit between my teeth with a gentle nibble and applied pressure licking it.

As she finally stopped twitching and was able to breathe again I slowly made my way back up her body. Never removing my lips or tongue from her body at the same time keeping her aroused and not thinking of asking me to quit. I made sure to pay attention to her heaving breast sucking, nibbling, and even biting her very erect nipples. She gasped and begged me for more as each nipple was bitten hard enough to leave an imprint of my teeth on them.

As I finally made my path to her neck kissing and softly nibbling on her firm flesh I had to remember not to leave any visible marks. This was a slightly harder than I thought cause I wanted to leave a lasting mark for at least a couple of days but couldn't cause it would lead to unwanted questions. Just as I reach her neck Bess quickly turns her head and our lips meet for the first time kissing with true untamed passion from both of us.

As we are locked in this abandoned moment of unbridled lust I have just enough presence of mind to line up and start inserting my diamond hard cock inside her dripping wet hole without ramming it in full force. As Bess feels me sliding into her unused but hungry pussy it is just enough for her to break the kiss and look at me. What I see deep in her eyes is mixture of desire, fear, longing, and a slight bit of shame causing me to stop briefly.

I tell it is ok we are only doing what we want that there is nothing wrong with it cause we love each other in a true and deep way. That I know it is her first time that I won't hurt her but it might be slightly uncomfortable at first but would quickly start to feel good. I see the fear and shame leaving and only desire, lust, longing, acceptance, and love behind so I start sliding deeper into her body.

Coming to a barrier ready to be parted I stop to kiss her again and to tell her to squeeze my arms if she feels any discomfort and that I am honored and glad she is doing this with me. Once I say this to her I thrust fully in breaking her hymen causing her to grab both my arms and gasp deeply. As I rest completely sheathed in her not moving until she let's my arms go I whisper to her I Love You Bess.

Once she is no longer gripping my arms I start to slowly pull out and slide back in each time causing less of a gasp and more of a moan. After a few minutes Bess finally looks up at me smiles and says "Joe you can start to fuck me for real now I am ready." I begin to increase my pace gradually still trying to not cause her anymore discomfort but she says to me this feels nice but I'm really ready to be fucked now.

Now that Bess has told me twice to fuck her I let all restraint go and fuck her fast and hard. With each downward stroke Bess moans or says yes that feels good just like that Joe and please keeping fucking me Joe. With her talking dirty and my relentless pace fucking her when she once more cums causing her pussy to clamp down on my cock I can't help but pop off inside her pumping her full of my cum.

Since I had already squirted cum deep into Bess's body I keep thrusting into her until we are both spent and my flaccid cock plops out of her creampied pussy. Rolling off beside her I kiss her passionately once more before she cuddles up to me and we rest. In the haze and quiet afterwards I most have fallen asleep with Bess also taking a nap beside me.

It isn't until I feel Bess start sucking on my dick that I wake up looking down at her I ask you sure you want to do that. Her answer to me is no but since I had been willing to do everything to and for her she could at least try it with me and find out. I tell her I appreciate her willingness to try and that it feels great to have her lips wrapped around me.

She goes back to giving me a decent blow job better since it was her first ever. It isn't long before once more I am hard and again wanting to be buried deep inside Bess's body fucking her once more. I grab a hand full of her hair forcing her to lookup at me so I can signal want I am wanting to do.

She climbs up my body as fast as she possibly can soon positioning her wet opening over my now erect cock. As I pull her down impaling her on my dick she lets out a sweet moan and drags her nails across my chest. This time I decide to turn over full control to her as she starts riding like she is on a horse escaping a war party. I am completely enjoying watching her as she loses herself in the pleasure she feels inside her and soon feel her again clamp down on me in orgasmic bliss but I am not done yet.

Since she collapses on me spent afterwards I decide to now take her from behind and soon I am fucking her doggy style. Every time I drive my cock into her she is still feeling deep untapped pleasure she has just started to feel. I keep relentlessly pounding her causing her tits to bounce as I slap her ass. Getting the desired response from Bess which is her pleading with me to keep going and not to stop until once more I dump a load of cum deep inside my little sister causing her to again cum. This time we stay awake and rest Bess telling me how she enjoyed everything and that it all felt wonderful.

That is when we noticed the time and knowing our mom will soon be home we quickly get dressed and Bess leaves going to her room with Alex. We really didn't get a chance to talk about what happened more than what Bess said afterwards. So the next day when Bess came in my room shutting and locking the door behind her while saying "Joe we need to talk about yesterday!"

I wasn't surprised in fact I had be expecting it that whole Saturday and was prepared I thought so I said "Ok fine let's talk Bess. What is on your mind and what exactly is bothering you about yesterday?" She quickly stats that while yes she had fun and had enjoyed the whole experience she wasn't certain it was ok for us as siblings to do it with each other.

Now I had known this was a possible problem and that if we continued it would have to be her decision but that I could influence her either way. I could influence her to continue with underhanded means and harm her in the long run or be understanding and make it a good complete experience. So actually loving my little sister I choose the latter and asked why she thought and felt that way. Of course she brought up it having to be kept a secret due to how others would react and that she wanted more than just a sexual relationship and that she felt like others would view her as a slut or worse if they knew.

I addressed the first and last first and together because they were the easiest and had similar reasoning to put them to rest. I told her that I wouldn't tell anyone we had sex even if she wasn't my sister cause that wasn't any of their business it was between us and no one else that made it truly special and meaningful. That even if we weren't siblings others could still see her negatively for having sex but since it wasn't anyone's business their opinion didn't count. The second one was harder cause it could be harmful if not handled right or be the reason to stop if handled right but not handled properly.

I thought it over before telling her our relationship could never be just sexual cause we already had a bond of love. That if we kept having sex it was just another aspect of our current relationship and that is why I wanted it to be her decision if we had sex again. That if she wanted we could continue having sex as a game or learning experience or just cause we enjoyed fucking each other it didn't mean she would ever stop being my little sister.

She then asked what happened if either one or both decided to have a more typical boyfriend girlfriend relationship with the other or got into an actual relationship with someone else? It was at this point I knew I had her but had to continue to tread carefully or undermine everything I had done already. As far as the actual relationship part I told her we would only have sex if both of us wanted that we had to agree not to get upset when one wasn't available. Then I went on to say while yes there would be certain aspects of life we could never experience together we could continue until they came up and decide then to quit or continue the experience.

As far as being in a dating relationship we could as long as no one who knew also knew we were siblings as well cause of societies current views. While yes around the family we could not tell it wasn't important as long as we were happy and content. That I really wasn't bringing dates around any ways but again it was her decision to make.

After thinking about it for around 10 minutes she finally looked up and asked "Joe will you do me a favor while I think this through?" I of course told her yes whatever she needed or wanted I would do willingly. That is when she said can we just lay her for awhile so I can think with your arms around me.

After laying with her in my arms another half hour before she suddenly turned over and gave me a quick kiss. After kissing me she said "I need you to take all your clothes off and do nothing until I tell you. There is something I need to do and see first only then I will be able to give you my decision ok?". Again I told her of course whatever she needed to help make up her mind I would do cause that way it could be her decision alone.

I quickly got up taking my clothes off and laid back down on the bed to watch her get up and undress herself. Then for the second time in two days she took my cock in her mouth sucking me until I had cum in her mouth with her swallowing what she could she kept sucking until I was once again hard. The second part was hard being sensitive but I knew Bess meant she needed this not to just decide whether to continue but if what we had already done was ok. Once I was hard again she impaled herself on my shaft riding me like there was tomorrow through two orgasms. After the second one she collapsed on my chest tired and told me I could do what I needed to do to cum again that once that was done we could finish our talk. So I rolled her off me on to her back taking her again in the missionary position pounding her pussy until I finally unloaded a third load of cum into my little sister's soaking wet and now well used hole.

It was only after giving her every last drop I had to give her that I laid back down beside her and took her in my arms. Laying her head on my chest she tells me that she definitely wants more that in fact she doesn't think she will ever want to completely stop but that was for another day. She went on to tell me she was happy we had done it and would gladly continue as often as possible, as many ways as could be done, and whenever I wanted her. I told her I only wanted her to fuck if that is what she wanted as well and that I would gladly keep having sex with her and that she had decided for herself that it was what she wanted to do.

Bess would tell me while she was on birth control she would appreciate it if I wouldn't always cum in her just in case. She wanted us to have fun and enjoy ourselves but that she didn't want to get pregnant. Plus if she did wind up knocked up it would blow our cover.

I agreed to do my part and either wear a condom or pull out often to keep her from getting pregnant. This is just the beginning with my sisters and I. By the time we would finish several others in our family will be involved or doing similar things together.