Little Sisters Ch. 04: Bess Explores

All parties are of legal age at the time of sexual activity.

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The thing I would soon realize with Bess is she loved sex from the first time we fucked. I am not complaining about it but you wouldn't believe how much she wanted it. After that Saturday it was almost a daily thing for my dick to be buried in one if not all of Bess' holes at some point. Before the end of that first week I added her anal virginity to the list of me taking.

I don't know how we never got caught between the close calls and her being aroused by them it was a miracle. There was this one time we were in the loft of the barn when Alex came looking for Bess for our mom. Just before she sees Bess with my cock up her ass barely staying quiet she is called back to the house by mom. Even then Bess nearly gets us busted when she can no longer take it and screams in pleasure "Yes Joe fuck my ass just like that."

Luckily Alex didn't hear her and we got by with it once more. I think that is why we did it so many different times and ways cause the thrill of not getting caught when we kept coming so close. After that first weekend for almost the next three months Bess would come home from school wanting to try something new she had heard about from her friends. With everything we tried I only know of one thing we both agreed that we did not wanna try and that was piss and scat play.

We also never did anything with animals but that was not ever discussed we just didn't do it. Bess I realized later was a true nymphomaniac she loved sex and couldn't get enough of it and it really didn't matter what type. As long as she was getting fucked she was fine with it didn't matter if it was rough, loving, submissive, dominant, solitary, single or multiple partners, bondage, role-playing, and even forced.

One other thing with Bess was as long as it was during multiple partners that another female was involved she was OK but alone no not even if the I was watching with intent to join. She would do anything with another girl but a guy had to be actively involved or she wouldn't continue. She never said anything about it she just wouldn't do it so I never understood why but I didn't push her either.

I guess I should now tell of 2 specific times that we tried something new during our sexual experience with one another. The first one is kinda of short but I think important cause it explains how we got into anal sex. Now the thing about this is where the idea came from was a fight our mother had with our stepfather in which taking it in the ass was brought up.

The argument took place the Sunday after our first time fucking and on Monday Bess wanted to try taking my cock in her ass. So after we had both finished our homework for the day we went down to the barn which thinking about it now was a regular spot for us to fuck. The reason we used the barn regularly for sex was neither mom or our step-dad went to it and Alex avoided it cause "It was just nasty".

As soon as we are in the loft Bess strips completely naked and tells me to strip as well. As soon as I am out of my boxers she has my cock in her mouth sucking it with a purpose. Now don't get me wrong no man is going to complain including me but I'm caught completely off guard and quickly cum right in her mouth. So here I am standing in the loft of the barn with my cock in my little sister's mouth that now has my cum leaking out of it while she is sucking on it to get me hard once more.

Once I am hard again she looks up at me with cum on her chin and says "Your turn big brother and don't forget about taking me in the ass today!". Which is the first time I have a clue about anything other than me fucking her pussy causing me to ask her "What do you mean by that?". Without blinking an eye as I begin to go down on her licking her sweet nectar from her wet folds Bess tells me "I want to take your cock in my ass like mom does our step-dad's cock". Now this is a bit of a turn off for me thinking about our parents fucking but with Bess laying there naked wanting me to fuck her in the ass it's not that big an issue.

So after eating her pussy out through one orgasm and making sure to well lubricate her rosebud and my cock do I turn her over and start pushing my cock in her ass. I thought her and Alex's pussies were tight the first time but they had nothing on Bess' asshole. It takes me awhile but finally I work my cock into her ass all the way but it wasn't without a lot of patience and discomfort for us both. I suggested that we stop a couple of times and just fuck normal but Bess was set on me fucking her in the ass at least once.

I will admit that we both had no idea what to do for anal that first time otherwise it would probably have been easier and better. That being said once I was in there I did take my time and make sure her ass stretches around my cock. Once it does though it quickly became one of Bess' favorite ways to get fucked and didn't take long before she once more was cumming on the floor in the loft. I was close to my own release when hers hit causing her ass to clamp down on my cock and push me over the edge again.

Once I was able to remove my cock from the vice grip her ass had on it Bess washed it off with a rag she had brought with her before once more sucking me into her mouth. She did this to make me hard once more so I could also fuck her pussy and cum in it as well so she could have had cum in all three of her holes that day. I was barely able to fulfill her desires that day but did get it done but I was totally spent from the effort.

The other experience I had in mind happened a couple of months later and again it was all Bess' idea that I would not have a clue until it was happening. In fact Bess set me up and did her best to make sure that I was not aware of what was happening until it was happening. Now Bess and one of her friends had been talking about their experiences with the guys at school without saying who they had been with. When her friend told her that she hadn't had a good experience yet Bess offered to make sure she did as long as no one else found out about it.

She would agree to this and to the term of later joining in a threesome with Bess little did she know that both would happen within the same weekend and with the same guy. So when Bess got home that evening after we fucked she would explain about her friend and ask me to fuck her making sure it was good experience for her. Now this isn't a bad looking girl it was the inexperienced guys that she kept hooking up with at the time was the problem. She stood about 4'11" 120 lbs light brown hair green eyes and a 28b cup.

So of course I am more than willing if Bess is certain that she doesn't mind me fucking her friend. Which of course she doesn't seeing as she is planning to have me fuck them both soon afterwards. Bess would then go ask my mom if her friend could come over Friday and spend the weekend with her. Which she agrees not knowing what exactly Bess has planned for the weekend. Mom would inform me to expect Bess to be bringing a friend home on Friday and to make sure to behave myself which honestly she should have told that to Bess.

Friday afternoon finally arrives and I am just getting my chores and homework finished when Bess arrives home with her friend. Now the plan was that Saturday morning I would go out into the woods in front of the house that actually surrounded the whole property and make my way around to the barn in the back of the house unseen. Then after I had been gone for a bit Bess and her friend would go to the barn and out into the fields to explore. Well Bess would actually be in the fields alone cause she sent her friend up into the loft where I would be waiting for her.

There would be two slight unforeseen problems with this plan that would delay things but not derail them. The first being that Alex followed me that morning out into the woods and wanted me to fuck her. Which wasn't that much of an issue since I left earlier than planned so I was able to fuck her and get to the barn on time. The second being that my step-dad choose that day to come down and use the punching bag hanging in the bottom part of the barn. So that when the girls arrived Bess couldn't really send her into the loft alone at the time with him right there.

So they both went out into the field and watched for him to leave which wasn't very long. Also luckily I heard them say hi to him so I stayed put and still so he didn't know I was up there since no one but me and Bess went into the loft. After watching him leave the barn and go back into the house Bess quickly showed her friend lets call her Sue from now on how to get up into the loft. Sue was shocked to find out Joe Bess' big brother was the one going to give her a good sexual experience but she said she didn't mind it was me.

Now I had plenty of time to recoup from fucking Alex earlier cause do to everything it had been a couple of hours since then. Also I took my time with Sue making sure to let her experience all the pleasure possible from me fucking her. From removing her clothes to putting them back on her afterwards I made sure she enjoyed every last second of it. I will admit that I got a little carried away and left a couple of noticeable marks on her that fortunately went almost unnoticed by everyone else except for Alex.

After first removing her shirt and bra I laid her back on the blanket we had in the loft to play with her breast. Pinching and massaging one while biting, licking, and suckling the other only pausing long enough to switch sides. I would continue to do this until she would pull me up so we could kiss deeply and passionately with our tongues wrestling for control and space in the others mouth. It was during this time I would unfasten her trousers and start pushing them down before starting my way down her body with my lips.

I would leave a mark on both sides of her neck that just barely showed above the collar of her shirt when it was on while making my way down her body. I would not realize they were there until later when it was brought to my attention but that's for later. Once I had made my way down over her breast again pleasuring them both past her navel with my tongue to the point right above her sweet split Sue would experience her first orgasm ever. I think most of it was from anticipation of what was yet to come after what had already been done to her body.

I would waste no time diving into her delicious pie to lick, finger, bite, and suck as much of her succulent nectar from her wet valley. It would not be long before I found her legs clamped around my head and both her hands pulling me deeper into her pussy smothering me as she once again came this time on my face. Once she had come back down from her blissful high and caught her breath she took my raging hard on in her mouth saying "Now I am going to thank you for giving me my first two orgasms ever.". I told her that I definitely appreciated it but she didn't have to unless she wanted to but it would help if she would suck me until I was hard once again after I had cum in her mouth. She was more than willing to do what I asked with the promise that I would not be finished after I had cum once but would still be able to fuck her to another orgasm afterwards.

I had thought at the time Bess was an expert cock sucker but Sue beat her hands down easily. She had me cumming in her mouth in no time and never lost a drop swallowed every bit of it and soon had me hard ready to plunder her snatch. After I was again hard I pulled my cock out of her mouth to the slight sound of disappointment only to change to longing as I lined up to her hole. As soon as I buried myself inside of her she wanted off her back and on top of me. So I rolled us over never pulling out of her tight welcoming love canal giving her the top position.

She rode my cock like it was a Pogo stick and she would die if she fail off of it. She was lost to the delirious pleasure of my cock being up inside her pussy that she didn't stop until she was spent from another mind altering orgasm. It didn't take long either but since I was nowhere near close to cumming again seeing as I had already cum twice that day once in Alex and once in her mouth I wasn't finished with her quite yet. So I rolled her off of me and turned her over to enter her once more this time from behind causing her to once again orgasm from anticipation of the fucking she was about to receive.

I would then proceeded to ravage her mercilessly from behind until she would experience her last orgasm of the day while I exploded deep inside her releasing my full load into her waiting womb. Bess had told me that Sue was also on birth control so I wasn't worried about painting her insides with my cum. I would then collapse beside her both of us completely spent and exhausted from the mornings activities unable to move for several minutes. Once we had both come around and had enough energy to move about we got dressed but before we left our separate ways Sue said "Thanks Joe that was the best experience I have had and I am glad that I have had sex now".

I would tell her I am glad and that she deserved to also be fully pleased that if she was with someone unwilling to get her off to she could always find someone else. I also said that I would be more than willing to fuck her again any time she desired all she had to do was ask. I would leave Sue in the loft to wait for Bess who would meet me in the woods behind the barn to ask me to meet her in the barn after bedtime that evening. Now as far as I knew the plan was for Sue and Bess to camp out in the field by the barn that night. So I figured she knew I could easily sneak out to the barn for us to have a chance to fuck undisturbed.

The actual plan Bess had was for me to get to the barn right after she revealed that the reason she knew I would give Sue a good experience was cause we had been fucking for awhile. That she wanted me to fuck both her and Sue that night as well as to also try fucking another girl herself while also having a guy to fuck. I think the only thing Bess didn't expect was that Sue figured out about us fucking before she told her that night. After we got done having sex Sue was thinking about it and what Bess had told her about her good experiences and put together that it was from us fucking that gave Bess those experiences.

Sue also figured out that it was me that Bess wanted her to have a threesome with to complete their deal. Which after her experience that morning she wasn't against but confronted Bess before she was ready to tell her. When she did confront Bess with the knowledge of what was going on Bess admitted to it and got her to promise not to tell anyone since she was willing to share me and I had already expressed a desire to fuck her again. So the two of them planned out how they wanted that night to go before dinner let alone I got there.

Now when I got down to the barn that night it was to find Bess in the loft alone I thought but found out Sue was there hidden until things got heated between us. Sue came out of hiding surprising me by taking my balls in her mouth while Bess was sliding her lips down my shaft. To say I was shocked would be an understatement but it was a pleasant and a well appreciated surprise for me. Now both of them knew exactly what they wanted and once they knew I was fine doing them together they set down the rules for the night.

Which the rules were simple that while they wanted me to enjoy the experience it was about their pleasure and not mine that night mine that would come in the future. Which I enjoyed it and trust me when I say I was well pleased by both of them the whole time. Basically the rules boiled down to this that they would be doing each other and my cock was only to be out of one of their holes long enough to enter a new one. And which everyone my cock wasn't in at the time I was to leave alone for the one it was in to take care of without help or interference from me. I also had to promise not to say anything to them until after we finished for the night so that it would not be distracting to either of them.

So I spent the next couple of hours with my cock in one of their mouths while the other was eating the pussy of the one sucking on me. Then once I was hard I would take it and fuck the one eating pussy until I had cum in that pussy and flopped out. Only to find myself now in her mouth while the other proceeded to eat my cum out of freshly fucked pussy. Then once I was again hard I would fuck her pussy until I left a cream pie in it to be sucked out by the other again.

We did this for I don't know how long through them having several orgasm and me wondering how I ever could keep going until finally we reached the last act. Then they informed me that I was going to take Sue's anal virginity with Bess helping that night to finish them off. I don't know how but I was hard but man was my dick sensitive and sore by that time but I was going to do my best not to let these two down. What I did not know at the moment was that while I was alternating between their mouths and pussies they had been preparing Sue's ass unlike I had for Bess.

So when I got into position behind Sue with Bess holding her ass cheeks apart my cock entered her tight ass without the same resistance or Sue's discomfort. Sue also enjoyed me fucking her in the ass hard once she got accustomed to my dick being lodged firmly inside it. I wouldn't cum in her ass but brought her to another orgasm before also fucking Bess to an orgasm in the ass not cumming in hers either. I just didn't have any more left and once they both had another orgasm I was so tired and sore I was glad to stop.

I laid down in between the two of them for a little bit to get enough energy back to sneak back in without getting caught. When I got up to leave I gave them both a passionate kiss and told them I was looking forward to the next time both with them alone and together but that they didn't owe me anything. I explained that while they may not have been seeking my pleasure that night I had definitely received my fair share of pleasure from them that night.

As a final side note for this chapter while I left other marks on Sue that night and on Bess only those on Sue were noticed. The person who noticed them would approach me on Sunday morning questioning how they got there on Saturday and if I was the one to bite her. That they knew Sue wasn't in the field with Bess after our step-dad went back into the house so did I meet up with her and make them. I saw no reason to lie so I admitted to Alex that I fucked Sue soon after fucking her that morning and that I had plans to fuck Sue again before she went home that day.

This would be one of the few times Alex knowingly took part in anything kinky by having me fuck her again before I fucked Sue. Which I was fine with even though I hadn't fully recovered from the activities during the night but was adequate for the task at hand. This would also be one of the roughest fucks I had with Alex since she was practically blackmailing me into it this time I decided to make sure that she knew I was upset with her actions. I also made sure Alex had four very distinct marks on her body when we finished to insure that she kept quiet about me and Sue and unknown to her Bess. The four marks I placed were as follows one under her shirt collar easily, one on her left breast, one on her right inner thigh, and one on her right ass cheek.

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I hope you enjoyed this one and that it wasn't to long but I need to cover this ground before the next few chapters.