My step sister [F] fulfilled one of my [M] biggest fantasy’s. Part 8: Another Shoot

Once again my apologies for the delay, RDR2 and Pokemon ate up every free hour i had this week :/ But here it is the long awaited part 8. I was sort of putting off this chapter and considering condensing my story to the point where i could comfortably end the story of my experience part 8 but due to a number of kind messages i decided to continue writing it as i have done the others and finish the story at a pace that as already been set and makes sense of the story. I re-wrote this a few times as i just wasn’t super thrilled with how it turned out and it needed a drastic change. There have been some new recent developments with my sister that needed to be added and reworked into my future chapters and i have never been happier to do so and am happy i get to continue my story further as it was basically wrapping up in this chapter and concluding in chapter 9. I cant really give anything away yet or want to spoil the surprise but what im talking about will be made apparent in the next chapter and this event will possibility be happening around Christmas and it is something that you readers will be experiencing with me in real time as my story basically will be catching up to me at the end of part 9 and hopefully reaching a new level depending on what happens next with my sister in a chapter 10 i very much want to write. I have been really pleased to share this 3 year journey with you guys through my writings and it feels very much coincidental like fate that i started writing this and that you readers might be here to maybe wrap it up me in current time and share what i have been hoping for to happen. Anyway here is part 8 and thanks for the continued support.

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Just a heads up there will be some spelling and sentence errors, i did not have enough time tonight to read through everything on this near final draft and fix any issues but i will do that tomorrow night so my apologies for that. I figured id rush this draft out tonight to quench everyones thirst and i will make sure anything incorrect is fixed tomorrow for future readers or if you want to held off reading til i correct it. THANKS :)

The day rolls around for me and my sister to embark on yet another weird erotic experience together and for once i wasn’t stricken with nerves or anxiety, the whole scenario almost felt normal at this point and i just figured if things went south again that it would be resolved in a few months and we would be back to business as usual so i wasn’t to concerned with another “losing my sister” outcome. I pack up the same equipment i used to shoot her last time and begin my trek to what would be another day i get see pure perfection in the flesh. The weather was beautiful outside and the drive to her place was pleasant and relaxing. While on the road i tossed scenarios around in my head of what possible outcomes i was aiming for to happen this afternoon and also what kind of emotion id be towing behind me on the ride home. I once again made sure to save up a load for a few days prior in the event that i would be getting another chance to release my self on my sister, i also made sure i brought more cash than i ever had previously to a deal just to make sure my bargaining could be backed up and i could get what i was trying to achieve that day. I was going here with one major goal and that was for me to work my self into a good spot and maybe see if she would give me a blowjob or in my wildest dreams hopefully agree to fuck me. In my head i knew i was still a scumbag for doing this behind my woman’s back but i rationalized it in my mind that what i was doing wasn’t an super wrong and that i wasn’t looking for love with my sister or seeking out to have a secret affair or relationship with her, all i wanted was to scratch an itch in my being that i have had with me since me and her first met.

For some background on myself in regards to my actions. This has always and still is a major personality trait of mine. I find myself constantly trying to achieve missed opportunity’s i never took or was to naive to see when i was younger. I find myself chasing down events and things from my past i lost and i keep trying to accomplish goals i had and could have seized but never achieved them weather that be personally or professionally. I can remember back to the exact moment i could have fucked my sister but alas i was just a timid shy 18 year old guy still trying to make sense of everything in the world. She invited me over to her new basement suite as she just moved out of my parents place for the first time and she was excited to share it with me. We decided to have drinks and watch a movie and that i could sleep over and we could just hang out and enjoy the night. I show up and we have some drink and order a pizza,i can recall skipping the movie as we couldn’t figure out how to get her audio to work through her system she had. The conversation turned sexual and we were both trying really hard to act cool by saying how many sexual partners we had and how hot shit we were. We were both very inexperienced and were just throwing bull shit out there, but the whole time we talked about sex i got extremely hard just hearing my sister say the words she was saying. I adjust myself on her couch and tuck my boner into my waste band and before i get up to go to the bathroom. I recall starring at myself in the mirror trying to come up with the perfect play to maybe bang her as we were both adults now and we had the house all to ourselves.

I give myself a couple strokes before settling on walking back into the living room with my penis and seeing where it went from there. Looking back on it now my thought process was pretty fucking weird and not i was not right to put someone in that position but for an inexperienced dude who was maybe a little behind on picking up signs and doing the right moves to win a girl over it just seemed like a smart idea and was a right to the point situation. I finish up in the bathroom and as i exit a pull my erect penis through my jeans and begin my way back to the living room. As im walking back i pass by her room and notice she had brought her single bed from my parents and it had the same seats on it that we used to build tents with as children. Seeing that creeped me out and in my head i knew i could not fuck her in there, plus with all the porn i have watched i figured a stud like myself needed a bigger bed and a grander stage to fuck on and a single bed would never cut it. Just before i reach the living room i snap out of the weird decision i was about to make and i felt really gross about myself and knew this was not right at all. I put my penis away and go back to the living room and sit down beside her. The night continues on and she tells me shes super tired and that we should go to bed, i agreed as i was felt like i totally killed my night by acting like a fool and almost exposing myself to my sister in the hopes that she would want any of it. I ask where i would be sleeping and she said the couch is yours if you want, i joke with her and tell her how much i hate sleeping on couches as it always seems to fuck my neck up for a couple days afterwords. She said thats cool and that i could take her bed and that she would grab the couch for the night since i was her guest. I told her thats not a good plan and i didn’t feel right making her not sleep in her bed under her roof and told her i can deal with the couch for the night. She then suggested that we could share we bed together for the night and that it wasn’t a big deal to her. I at this point was super nervous after seeing the size of it and knew we would basically be spooning each other for the night, my balls were aching from the boner i had not taken care of earlier and my body just wasn’t feeling any sexual activity of any kind for the rest of the night. If she would have brought this up when i was hard i might have been game but the part that i still dwell on is that i declined her offer and said i would think it would be best if i just went home for the night and slept in my bed.

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She said that it would be fine and she was cool with having me for the night. I said i didn’t want to bother her and keep her up all night in a hot and tiny bed and that she needed to get a good nights rest as she worked tomorrow. She finally agreed and we called it a night. I did not drive at the time so i had to resort to phoning my mother and waking her up in the late hours of the night to come pick my dumb ass up. My mom pulls through and picks me up, i hug my sister goodbye and we mention making plans for another night and laugh about maybe getting an air mattress next time. I get in my mothers car and receive a tongue lashing from her all the way home about how i was supposed to stay the night and how she was sound asleep and now i ruined it. I got off the hook by claiming i was pretty tipsy and wanted to walk home but figured it might be dangerous and she apologized and said i did the right thing in calling. This moment in my life is honestly where i feel my constant chasing of the dragon known as fucking my sister was originated from. Its a moment as you know i dwell on and am trying my best to undo the moment that passed me by from my youth. Im still not sure if she really was hoping to kick something off in her bed with me that night but it was just way to small for the two of us and she had to have known exactly what she was requesting when she pitched me that idea. Im interested in hearing everyone thoughts on this and hopefully im not reading to deep into her simple gesture and blowing it out of proportion. Jump back to the current story at hand of me making my way to my sisters, the moment at her place years ago replays in my head and today i wanted to rectify it by hopefully getting in bed with her and sealing the deal.

What i was trying to accomplish was so wrong and i have never been one to support cheating but this just felt like something i needed to do so i could move on and stop dwelling on such a stupid concept and goal i was madly chasing and risking a lot in doing so. I make it safely to her place and we exchange greetings and hugs. In a much different setting than last time she rushes me in and sits me down and we get right down to business. She tells me that plans have changed for the day and that she was no longer to hang out for the evening as her boyfriend would be getting off work in 2 hours or so and that we needed to make this quick. I was a little pissed off by that considering the drive i had to make but i would usually hit the malls in her area anyways so it wasn’t a total waste of time and gas and besides i had no other option than to agree with her wishes and i began to unpack my belongings. My sister had already gotten herself done up quite nicely and had been ready and waiting for my arrival. Her skin was much more pale as she had missed her tanning appointments recently and i was very eager and interested in seeing her nude without the tan skin for once. She runs to the bathroom and i watch her applying some lipstick and finishing the last final touches on her self. I ready my camera with my preferred settings and ask her where she wants to do this, she points at her windows and tells me she was washing her curtains so we couldn’t do it in the living room as she didn’t need people looking in and watching and i said thats fair. I tell her that im guessing we are just sticking to the bedroom and she agreed and told me we could do some more in the bathroom if need be and i agreed with that. I follow her into her bedroom and within a moments notice she strips off her yoga pants and hoodies and reveals beautiful red see through lingerie underneath that matched with her lip stick and her hair accessories. I mention how well she put herself together and really made her outfit match and look great. She laughs it off and said she didn’t even notice all that before which i personally didn’t believe and deep down was hoping she did it for me.

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Once again i am very unprepared and i stand there clueless in regards to what shots i was looking to get today. I ask her before we begin what exactly am i getting away with today and how much i would be paying her today. She proclaims that all the line crossing and getting carried away on both parties sides would not be happening today and that we were not going down that path together again. I agree but i knew with the amount of cash i had on me i could change her mind at any moment. She said that if i gave her $200 i would get to keep all the shots i took today considering we did not have enough time to go through them and have me select what i wanted to keep considering her boyfriend would be coming to see her later. I agree to her terms but figure i can push my luck later and see where it gets me, She smiles and says how she knows im going to need to release all the excitement im going to get from this and said for an extra $50 i could cum on her tits at the conclusion of the shoot just like i had done previously. I tried my best to suggest maybe cumming somewhere different this time liker her ass but she wasn’t having any of it and basically said its on her tits or its in a Kleenex. I felt like my day was completely shot as my sister was all business today and wanted no bullshit or me weaseling my way into something more than what she was offering. I still took it as a win for the day still as i was still getting to see her nude again and was going to drop a load on her so overall i was just being greedy and not appreciating what she was giving me. We begin taking some shots of her in various poses on her bed and on the floor in her stunning lingerie as i got her to slowly strip it off frame by frame. She of course notices my erection and tells me im allowed to jerk off while we shoot just to move things along faster, i oblige and strip down and begin snapping photos with one hand and pleasuring myself with the other. She is completely naked at this point and im making damn sure to get as much content i can considering i can keep it all. I ask her to bend over and she does so and lets me take a few pussy and ass shots close up from behind, i thank her for being so generous and joked about how things have changed since our first shoot. She brushed it off and said its not like you haven’t seen it before and that she figured i would like some new shots considering i pretty much had her covered from every angle in other shots.

I laughed and said if thats the case maybe i could get a few shots of you spreading her lips for me, she didn’t seem thrilled with my comment and shot it down right away. She told me if i wanted it that bad than that would be an extra $100 dollars. For some reason this time around my sister wasn’t as desperate for money and almost seemed to have a major change in attitude. I think this time she was really clued into how badly i wanted these things from her and she knew she could bleed me dry to get them this time around. She had what i wanted and she knew her worth to me and was really going to charge me big time for any extras i ask for. Knowing this and feeling a little taken aback by her attitude i declined the offer to give her more money and sad i can live without it. As much as i wanted to see those perfect pink lips spread wide open for me it felt like to much money for what would be a massive tease to me considering all i ever wanted was to be deep inside those beautiful lips and it would have killed me seeing what i would be missing. Our time together is winding down and my sister lays down on the bed and gets into the same position as last time for me to cum on her. I straddle her and begin stroking my cock at a fast rate as i knew i had to wrap this up quick. Something was much different this time as i felt myself having trouble orgasming which was something i never really had with my sister considering i was always leaking pre cum around her and always was ready to bust at any moment. I could tell my sister was getting visibly annoyed as she was eyeing up the clock while watching my penis and me for any sign of progression which made things much harder for me. I think her attitude that day and behavior she took with me that day and the suddenness of everything really put me off and i just wasn’t in the head space like i was in previous times. I asked her if i could play with her tits to help me out a bit and she said sure but it was going to cost me an extra 20, I agreed as that was very fair to me and begin playing with her perfect chest which never got old to me. She keep asking if i was close and that i needed to wrap this up soon or i would be out of luck, her tits were helping me out but her comments counterbalanced that and i didn’t feel that much closer to orgasm.

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I said i was trying my best and the pressure of our time running out was really getting to me. She sympathized with me on that and told me to grab the lube from the night stand and apply it to her breasts and my penis. Hearing her say that made me a bit harder and i did what she asked right away. She said that she would not be giving me a tit job and that i would be the one doing all the work on this. She pushed her tits together and told me i could fuck them until i was closing to cumming and than at that point i would be the one to rub it out on her tits. I asked her if i could just cum while i was fucking her tits and she said no, she reminded me the deal was i would jerk myself off onto her and we were sticking to it. That didn’t really help me much as every time i got close while fucking her breasts i would stop and try and cum while jerking it but my load would go away the second i did that. At this point im hot and sweaty and my sister is telling me i dont have a lot of time left. I have nothing left to lose and tell her im trying my hardest here and that i felt like i needed a little more to get me over the edge. My sister reminds me that this would not be escalating and that we both agreed to that. In my head i knew she had a high price tag today and wouldn’t budge on the rules she set unless i possibly offered up a ton of cash. I decide to go all in and i get off the bed and head to my jacket in the living room. I return to her on the bed who looked visibly confused and i pulled out 3 crisp $100 bills, I show them to her and i ask her if she finishes me in her mouth i will give her this on top of what i owed her for the days shoot. She was making nearly $600 dollars that day but her face didn’t show any emotion towards my offer. She sat quietly pondering it before she told me to get back on the bed and climb on top of her, i asked her if she was agreeing to my rules this time and she said yes it would be fine.

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I straddle her again and she began stroking my cock to get it a bit more hard before it entered her mouth. Something i awaited longed and wished would happen forever was about to be a reality, but something in me just wouldn’t let me enjoy it, my sister seemed so miserable and would rather be anywhere in the world than in that room with me. My now very hard cock was hovering around her lips and i braced myself for entry into her mouth. In the moment i got carried away and said i knew one day we would get to this point and i thanked her for everything she does for me. She moved my cock away from her move and almost snapped it me and scolded me for saying that. She said this was never about me and you and while maybe i was getting pleasure out of it she got absolutely nothing from it. I got defensive and called bullshit on that, i reminded her of our last encounter and how it seemed like she was pretty ready and willing to go the extra mile and satisfy me more than once. She also gets her guard up and says that this as always been about the money and how if it wasn’t for my deep pockets that i would never be in this spot. At this point im pretty hurt and shocked by all this, Was i reading this all wrong? I knew money was a huge factor in this but i figured she was into this in some way or form and got off on some aspects of it or else it wouldn’t keep happening. My sister than says lets just drop this and get this over with, a moment i wanted to treasure and feel every part of was ruined and she took my penis in her mouth and began giving me a very poor blowjob and was clearly rushing and going as fast as she could just to end this awkwardness as soon as she could.

The image i had painted in my head of her finally blowing me did not look like this one bit and i honestly did not feel much pleasure for it. I try me best to focus and make the most of it and concentrate the best i could to help me achieve orgasm. I was so upset at my sister and her words i wanted nothing more than to fill her mouth full and make her gag on my load. Never thought me and her would wind up in a hate fucking blowjob scenario but here we are, she was using quite a bit of teeth and it felt pretty rough but i worked through it and managed to get myself close to orgasm. I can feel my cock swelling in her mouth while she unenthusiasticly continued sucking but i knew for the price tag i was paying i had to make the most of it. I can feel myself at the edge and my dick swells even more in her mouth, i wish i would have looked at my cock between her plump lips more but i didnt want to be reminded of how unimpressed she had looked all day so i just kept my eyes closed and dreamed of a different scenario with her sucking me off. I finally begin to build up to my climax and from what i pitched she would be finishing me with her mouth. I feel my load inches away from escaping my tip into my sister mouth, just as i get there and feel the euphoria of my orgasm she stops sucking me and removes my head from her mouth leaving me with nothing but a ruined climax. I didnt even get to enjoy it or feel the payoff before i look down and see my sister with both hands blocking her mouth and while i tried my best to salvage what cum i had left and tried jerking out what ever was left. My sister asks me what the fuck i was thinking and i got heated with her back and said i asked if you would finish me with your mouth and you agreed. She told me thats not how this works and said she agreed help finish me with her mouth but i still had to follow the rule of rubbing my load out myself and how she wanted zero part in being the one to finish the job. I shook my head and told her how stupid this was and how all these rules and little loop holes made no sense and told her i didnt understand why she was acting like this to me.

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She tells me that i need a reality check and that things would just continue to escalate further if neither one of us didnt put a foot down and put an end to all this nonsense. I finally just broke down and begin telling her how confused as i was regarding these deals and our feelings towards one another. I told her it seemed like she took great pride in the content and deals we were making and that she must have felt something towards me in all of this. I told her she was practically begging and salivating for my cum at one point, i told her she either did a great job acting for the money or she shared the same regrets i did about not hooking up ages ago. She said once again at no point in our encounters together recently did she feel aroused or wanted to take things all the way with me. I to this day still dont believe that all things considered but on this day she was ruthless with her words and was really trying to do some damage. It felt so weird still on top of her with my lip penis dangling in front of her face, her cum covered hand finally move away from her mouth and i notice i got some cum on her lips. I point that out to her and she said are you fucking kidding me and grabs some Kleenex and begins wiping her face and spitting into it. I smirked and said she wasn’t fast enough and she just replied with wow your so funny and began telling me how disgusted she was with herself about the whole thing and how weird it was how she knew all my cues and tells from my penis and body for when im about to cum and how that was just way to personal and gross for her.

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I remind her she had no problem taking my cum any other time and i got off of her and the bed, She demands for me to sit back down on the bed and that she was going to prove something to me so i would just get over all of this and that she wanted to show me exactly how much this aroused her. I ask her what the hell shes talking about and she tells me to hurry up. I sit back on the bed and that’s when my sister opened her legs towards me and showed me her beautiful pussy. I was a little puzzled by her actions and asked her what she was trying to do. She said even though she regrets doing this it had to be done and she wanted me to see and feel first hand that she was not aroused or turned on by today’s events. I laugh at her odd request and ask if she was joking or not considering there was so much miscommunication that day and i wasn’t about to get myself in any trouble or get scolded again. She sits up a bit and takes my hand and aggressively places it on her pussy. She was slowly killing every fantasy i had ever conjured up in my head and i always felt the day i got to finally touch her perfect meaty would be a glorious one but in all honesty i felt very uncomfortable. I run my hands down her bigger than normal clit and her meaty lips before ending at the entrance to the holy grail i have yearned for many of nights. She says go one stick a finger in there, I felt really strange and uneasy about this whole scenario but i figured i might as well just so i can say i did it. I push my finger into her and it honestly hurt my heart and feelings a little when i barley made it inside her very tight pussy when i noticed she was dryer than sand on a pyramid. She pulls my hand away and says ya see what did i tell you, now that we got that squared away we are done here you can pack your stuff and leave. She grabs my $300 of the dresser and proclaims that it belonged to her, i remind her she never followed through with the entirety of the act and that i think $150 was a much better price for the two of us. She shrugged and said whatever if that will get you out of here sooner than fine i’ll take $150 on top of what you owe me for today.

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I grab my camera and show her the screen, i go to format and erase all the content we shot that day. I was so hurt and let down by everything i knew i wouldn’t be needing these anytime soon. I didnt even feel right being in the same room with her let alone fap to her anymore. She asked if i was fucking serious and i told her they were of no use to me now and was only now a painful reminder of what went down today. I still gave her $150 for everything today so she walked away with $300 which was still very good for her and she was somewhat pleased. We argue a bit more and exchange words before agreeing we are done with all of this and that we would need a very long break away from one another to let things heel. As we continue our heated exchange we pretty much lost all track of time and within seconds me and me sister both snap back to reality in an instant as we just starred at each other both wide eyed and shocked each of us still completely naked as we hear a key unlocking her front door. We both had lost all sense of time in our heated states and forget her boyfriend was on his way home from work. We knew at that point we were both Fucked.

To be continued in Part 9…

Source: reddit.com/r/gonewildstories/comments/9z1t6e/my_step_sister_f_fulfilled_one_of_my_m_biggest