My step sister [F] fulfilled one of my [M] biggest fantasy’s. Part 1: The First Deal

Forgive me for any formatting issues or poor sentencing structures as i have never wrote something like this before on reddit so any feedback is much welcomed. For some incite this is just something I have always wanted to share personally and get off my chest and was always curious if anyone reading this has had a similar situation to mine. My Apologies for the length of the post, I felt I needed to give as much background info and detail as I could to do my experience justice. I have split this into a few parts ill be looking to upload soon.
Enjoy.

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Me and my step sister were always extremely close growing up together and always shared a special connection. There was always a bit of sexual tension between us but nothing ever happened considering both of us were extremely shy. The most that ever happened between us is that we kissed each other a few times as a joke but other than that nothing to wild. As time went on we grew apart and she moved to a new town quite far from me. I would try my best to visit from time to time but we had a difficult time staying in touch after her move. On the rare occasions we would get together we would usually have some drinks and catch up. We both were in serious committed relationships at this point so it never crossed my mind anything would ever happen between us two.

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Ever since I could remember I always found her extremely attractive and was one of the most beautiful girls I have known. As we both grew up she just became more and more stunning in my eyes and had an insane body to die for. I had always fantasized about doing things with her and dreaming of scenarios in my head where I would catch her changing or things along that line. She also had the most amazing pair of breasts on her and she knew that but was very modest in the outfits she wore. She usually would get comments about if they were fake or not considering how perfect they looked in anything she wore but they were all natural. I had always lusted for them but not once in any situation together did I get to see them but I always hoped maybe one day I would get lucky. At that point the most I had ever seen of her body was when we would go to the beach together and it would drive me crazy how perfect her body looked in a bikini and was always a constant tease to me and I just needed to see more. She eventually picked up a modelling gig with an agency and pursued it and gave it all her focus. I would always beat around the bush and ask her if she posed nude or did anything along those lines in hopes of me finding some pics of her online or on her photographers pages but she was always very adamant that she had zero interest in doing content like that. Her boyfriend was quite the jealous type and was very against it so she wanted to do right by him and just stay away from all that considering she was certain he would leaver her if she went that route.

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We get together a few more times that year and i’d always cautiously ask her questions about the modelling and jokingly tell her that people would pay insane money for some more provocative pictures and could maybe help her further her career. She eventually would briefly entertain my suggestion when she started to fall behind on rent and bills. I told her I had a few “friends” that would totally buy some pics from her so she wouldn’t expect me to be the one who actually wanted them. I was always extremely petrified of my real intentions getting discovered considering it would probably rip our two family’s apart and our spouses along with it so I just made it clear to her i’d be the middle man between the two parties and that’s it. Months pass and the deal never goes through or gets brought up again so I assumed that she was doing okay now money wise. The holidays roll around and my sister and I make plans to hang out for the night. My girlfriend was at work for most of the day so me and my sister decide to have a couple drinks and some tokes and play our favourite card game we played as kids. After some drinks I suggest we up the ante and I suggested an altered more adult themed ruleset of the game which included drinking and stripping cards and other adult party game themes. Much to my surprise she looked over the rules and conditions and said it looked like fun and she agreed to play. Within at least 10 minutes of starting the game I was unfortunately the one to be fully nude but she was on her way there and was being very selective about what item of clothing would come off.

Finally after years of fantasizing and hoping I got my dream and she had to take her top off as per one of the cards she had. My heart raced as she slowly undid her bra and her incredible breasts were finally displayed to me. They were more perfect than I ever imagined them to be, they were quite large and she had perfect sized and placed nipples, I was rock hard at this moment and was in pure heaven. She moved her hair in front of her breasts to cover them, I don’t even recall how long I was staring before she did that but it must have been pretty obvious. The game wraps up and she gets up to go to the bathroom and walks past my side of the table. It was at that moment her eyes very visibly locked onto my erect penis, I was extremely nervous as to what she would say to me about it and I figured she was going to be upset her brother was sitting there hard as a rock. She just kind of stopped and glared at it a bit before stumbling off to the bathroom. I quickly got dressed and for the rest of the night I felt sick to my stomach and was stressing out about what transpired. The fact I may have possibly changed the dynamic of our relationship and possibly jeopardized my bond with my sister really upset me and than combining that with guilt of having my girlfriend come home later that evening and me and my sister acting like nothing happened even though we were both naked and piss drunk just hours before. My sister goes home the next day and I asked if things were cool. She said she had a really fun time and looked forward to our next visit. I drove her to the bus depot gave her a hug and sent her on her way.

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I visited her the next month and we just chilled and spent the day together. After thinking about what happened previously at my place I figured I would push my luck and see what happens this time. We had some more drinks and I brought up the events of last time. I asked her what was going through her head once we were both naked, she told me she wasn’t really bothered and that it was just part of the fun. I asked her if it was weird now between us and she said there was nothing to worry about. I brought up the instance where I noticed her looking at my penis and she laughed it off saying we were both drunk and things like that are normal, it just took her by surprised but that in a strange way she was flattered by it. At that moment I knew I had to capitalize and I spilled my guts to her about all the fantasy’s I had about her and how seeing her naked was insanely hot for me and a dream come true and was something that was on my mind a lot since it happened. I was prepared for the worst but was relived I told her how I felt finally, she answered back and told me how surprisingly good that made her feel. She admitted that yes it was very strange coming from her brother but at the same time was extremely flattering and that it made her feel attractive for once. She told me she always struggled with her insecurity’s about her looks and and how she never felt like much of a catch for any guy. I was taken aback by her statement and we laughed how it took her brother creeping on her to get to this sort of issue. I figured id keep the ball rolling since we were opening up more to each other and I confessed to her that I would masturbate to some of her modelling shots and some sexy pictures on her Instagram. The look on her face was very surprised and she asked me how long have i felt this way, I told her it had been happening for awhile and she was always my go to for fapping. She told me she didn’t mind that I was doing that and found it to be kind of cute and was also intrigued she was able to have so much control over me without even knowing it and how well I hid these feelings. I told her we needed to keep this just between us and told her my fears of our family’s and spouses finding out and she agreed it was a secret we take to our graves. At this point it was very obvious she was pretty high on herself and my constant praising of her was really giving her a huge confidence boost. I figured now was my chance to get something I had been wanting forever and I asked her if she would make one of my fantasy’s come true.

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I asked her if she still had some money problems and she said yes. I told her that her modeling pictures have been good to me but I have always wanted something more. I asked my sister if she would be interested in taking a couple of nude photos for me and id pay her well for them. She didn’t hesitate to say yes and so we began working out a deal. She asked me for $100 for 10 pictures and that she would not go bottomless and would only be going topless. I agreed as I would have honestly paid more for those 10 pics. Within an instant she took her top off so suddenly like it was nothing now and asked me what kind of poses I was looking for. I froze big time, the scenario I dreamt about my whole life was right in front of me and I was riddled with nerves once again. I than suggest if she wanted to take them herself since I felt to much like a creep and that it was a little uncomfortable giving her directions. She obliged and took my phone to the bathroom and began taking the pics herself. I was once again fully erect from this situation but felt a little gross having my dick clearly showing through my pants. When she returned she noticed me trying to hide it but said it was no big deal and that after last time and all the things I told her she was expecting it to happen today. We both laughed it off and than sat down and we reviewed the photos. I was so happy with what I got, she took many different angles and really seemed like she knew what I was looking for and wanted to see. One picture in particular had her pushing her boobs together with her hands and she had her tounge out, I told her I would have payed double for something like that and she told me she was very happy I liked that one. After we exchanged the money I felt this wave of guiltiness again, I told her how I felt about this situation and she assured me everything was fine and no lines were crossed today.

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She got herself dressed and asked if I could take her to the other end of town to grab some groceries has she did not have a car and didn’t want to bus it all the way there. I jokingly asked what’s in it for me, she replied back with if you take me there i’ll let you touch my tits for 20 seconds and that should cover your gas there. I didn’t even ask if she was serious I immediately said yes and she unbuttoned her top for me. Once again I felt disgusted with what I was doing, I have a girlfriend and here I am out of town about to touch my sisters tits. My sister kept coming closer to me almost egging me on to grab them, I finally reach out and touched them and she set an alarm on her iphone and for those 20 seconds it was amazing. I did everything I could to those perfect tits in that short period of time. Her nipples became extremely hard during my fondling and just seeing that aroused me so much I could feel pre cum slowly oozing out of my tip. Once the timer went off and she buttoned her shirt up again I asked her if I could rub one out in her bathroom and jokingly told her if i didn’t i would have the worst blue balls of all time after all this. She laughed and told me to go right ahead. I kind of got lost in the moment and asked her something I would immediately regret. I proposed that if I gave her some more money if she would watch me cum. I told her she didn’t have to touch it or get naked or do anything else other than just watch me shoot a massive load. I was pretty much ready to pop and offered her $100 for the 1 minute it would take me. She replied with a very firm no way.

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She scolded me about how weird that would be and how we would both have a very difficult time seeing each other the same after something as intimate as that. I apologized profusely and blamed it on me thinking with the wrong head and quickly packed my stuff and began to leave. We both got in the car and I began the drive across town, the silence in the vehicle was deafening and you could cut the tension with a knife. I drove her about halfway before she asked to be let out at a nearby bus station and that she would finish the trip on her own. At that moment I knew how badly I fucked up our special bond and might have lost my sister over my sick fantasy’s. As she got out of the vehicle I asked if we were good and if things were going to be okay between us. She told me in a very non convincingly manner that everything was good and there was no ill will towards me. She waved goodbye shut the door and went on her way. I made the long drive home which felt like forever. I thought about every last detail of what happened today and my stomach was in knots and like predicted had the worst blue balls I’ve ever experienced.

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My girlfriend greeted me at the door and asked where I was all day, I lied and said at a buddys house and than did my best to act like myself and hide my shame after what I did behind her back that day. Weeks go by before I even looked at the photos my sister took as It was just a painful reminder of what happened between us and the reason we wont speak again. When I did finally decide to jerk off I pulled up her pictures, instantly i was very hard and all those feelings I had for my sisters body came back full force. I damn near shot my load on the ceiling from remembering the experience. After I came I felt a tremendous sense of sadness over what I did to get those pictures all just so I could rub one out to them.

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Time goes by and than something happened I never would have imagined but was always wishing it would. I checked my phone and noticed I had a missed call from my sister, my sister was never big on texting and I cant even recall the last time she ever called me. I stared at the missed call for awhile before getting enough guts to call her back. I was sweating bullets at this point and pondered what could be so important that she would call. Just saying hi? ,maybe she told her boyfriend? My anxiety was through the roof when she finally picked up and we exchanged hellos. We conversed a bit and caught up with each others lives. After a good 40 minutes on the phone she hit me with something I did not expect. She asked me if I was interested in doing another deal with me giving her some cash and her giving me some photos. I remembered how shitty I felt and how much of a strain this put on us and there was still the possibility of me losing her again. Even with all those feelings and the guilt I promptly said Of Course

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To be continued in part 2

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Source: reddit.com/r/gonewildstories/comments/9q9vuk/my_step_sister_f_fulfilled_one_of_my_m_biggest