This is a story about how my longest and most intimate and taboo fantasy came true on my 32 birthday.
As far back as I can remember, I have been attracted to one girl more than any other. That girl (now a woman) is my sister. Growing up, I was always the good boy and she was more of the black sheep (a trait that I found extremely sexy in her – not to mention that I think she is the most beautiful and sexy girl in the world). Even being a “good boy”, I had, on many occasions when we lived under the same roof, fantasized and spied on her. I used to wake up and wait to hear her start the shower (back then she occasionally left the doors mostly open. I am not sure she ever really knew how I felt about her… I was a virgin till I was nineteen because even sex was taboo. To fantasize about my sister was even more so. She was not a virgin, I think she lost her virginity around 12-13. I was so enamored with her that I had even been caught spying on her, by both her and a friend of hers one time.
I had multiple ways that I would spy on her, hoping to catch a glimpse of her goddess-like body. I would sometimes try to use the mirrors in her room to catch a glimpse, I would also go as far as to enter her room, hand-in-pants cock-in-hand and see how close I could get to her bathroom door. At one point I even removed my window screen so that I could slip out onto the roof and possibly see her getting ready. The times I got caught didn’t phase me in the least. It was such a rush and also made me more nervous than anything in the world to try to just admire her beautiful body. In addition to my spying tactics, I even stayed awake at night waiting till she would fall asleep. On more that a few occasions, I would creep across the hall and into her room, praying that her soft breathing and quiet snoring would mask my actions, and I would watch her sleep. I hate that it makes me a creeper, but I desired her more than anything. I would watch her sleep in the moonlight and would massage my cock as I looked on. At times I would even try to caress her body… my anxiousness would inevitably win though and I would chicken out. All that went on as long as we were living in the same house… after we moved out I had less of a chance. I still fantasized about her even when I was married. All I wanted was her. As life progressed… She had her roller coaster of life and ended up pregnant. Frankly, I was jealous… It would have been a dream come true to have been the one that impregnated her. I wanted her attraction and her more than anything else. Despite my getting caught spying, my craving and desire for her never ebbed. I wanted to feel her, touch her, taste her, caress her, penetrate her and love her still. I was and am infatuated with my sister. Since then, I have had multiple partners, almost as many as my sister, so I do have a base of reference on what I like, and what other women are like; so my infatuation, although to this point, was speculation has a strong base of comparison.
That is the back story… now fast-forward to about three years ago. My sister and I and her sons and my parents were in Florida for a vacation. My sister’s computer was acting up so she asked me if I could look at it. I obliged. As I was trying to fix it, I came across some pictures of her that were taken for (most likely) her husband. This was actually the first time that I had seen my beautiful sister completely exposed. When they opened, I was instantly rock hard… luckily no one else was at home. Without her knowledge (sorry sis) I emailed all the pics I could find to my account so that I would have something to look at later while I was self-pleasuring. Later that week, she and I went out to go shell-hunting. On the way there (I don’t know what possessed me) I decided that I would bring up the computer. The conversation went something like… “While I was fixing your computer, I accidentally opened some pictures of you that were ‘revealing'”. She immediately said “sorry”. I apparently grew huge testicles this night because I then said “actually I liked them, and wow, you are seriously sexy”… after her “thanks” I continued to talk about the pics, commenting on her perfect pussy, as well as mentioning the crush/infatuation I have had for her since I can remember. After convincing her that I was completely serious, she admitted to the fact that what I just told her was a turn on. At that point I offered to share some pics that I had of my cock… I was already in the deep end, figured I might as well swim. Now I don’t have the largest cock; it’s decent but not huge (though the typical descriptor is “just right” or “perfect size”). She seemed to like what she saw, and proceeded to tell me that my interest in her and my cock turned her on. I then got braver and decided to ask to see her breasts, she obliged. They were gorgeous, perfect in my eyes. Later that night I asked to touch them and she let me, and I also asked to see her pussy… like I said I was getting braver. That was pretty much it for the trip… over the last few years, we continued to carry on, and I was lucky enough to get more pictures of her beautiful body. We continued to talk and every time i saw her I desired her more.
About a year ago I thought I had hit the jackpot. We were both hanging out at her house and we had been drinking… This raised my courage enough to kiss her and more. We kissed and I got the first feel of her perfect pussy. Either that trip or that trip to where she lived combined, I not only got to finger her pussy and caress her breasts, but I also learned how it felt to have her hand on my cock, and to have my cock in her mouth. This was only a short tease though. It left me wanting more. Over the years to follow, I managed to get some more pics and to feed my fantasy more. All that leaves me where I am today.
I was visiting my family (who live 7 hrs away) this last weekend, my birthday weekend. I took a chance and asked for a birthday present to surpass all others from my sister. To my surprise, she gave me an option, a contingency. I had to do a favor for her and she would let me put my cock inside her pussy. Upon receiving that text, yes, my cock grew rock hard. I almost couldn’t believe it, honestly I didn’t. But as the day progressed… My anxiety and excitement grew… I even stroked my cock to the thought of what may happen. As the day progressed I kept reminding myself that this may not actually happen… I also kept reminding her that I hope it does. I went ahead and did the favor for her, and after the anxiety built as I learned that this was actually going to happen. Everything I have wanted for probably twenty years was about to come to fruition. Though even going into it and being reminded that “it is just sex”… I still doubted that it would actually happen.
When she got home (where I was waiting) she ended up on the phone with her husband (forgot to mention that)… Then after she hung up I asked where she wanted to do this. She led me up stairs to one of her extra bedrooms… we shut the windows and the blinds and my heart was racing. There in front of me stood the woman I have fantasized about for as long as I can remember… she was wearing a skirt and a form fitting top. I could barely contain myself… I was already getting hard and I couldn’t help but occasionally tease and play with my cock as we were about to start. Under her outer clothes she had on a bathing suit (we were initially supposed to go to a beach party)… as we shut the windows and blinds she commented “You know whats great about this bathing suit? All I have to do is untie the sides and I don’t even have to take it off.” At that moment her bathing suit was untied and I got to see her beautiful perfect pussy waiting for me. The bed in the room was covered in clothes and I asked her how she wanted to do this… her answer was to just bend her over the bed or something and proceeded to bend over in front of me… My hand immediately reached for her moist pussy. As my fingers touched her perfect lips and felt her wetness in anticipation, I told her… “No, why don’t you lay on your back? I want to look at you while we do this.” My words were brash and non-suave as my anticipation and hormones overpowered my vocabulary. She obliged again and after pushing the clothes aside, laid on her back in front of me… her legs spread wide open, pussy bare… just for me. I had asked her if she was ok with me taking some pictures and she had said “that’s fine, as long as they don’t end up on the internet”… so at this point I decided to snap a shot of her, legs spread, awaiting my cock. Then one of my cock hard and lined up with her awaiting lips. i could barely focus I was so aroused. That’s when it happened… my fantasy of over twenty years came true. My rock hard cock pushed past her waiting pussy lips and slid deep inside her pussy. I can not even begin to describe the feeling, much less the emotions I was having at that moment… I am still having difficulty believing it actually happened… As we started, it was regrettably very matter of fact… I took some pictures of my cock penetrating my sister, her wetness glistening on my shaft… and then I was overwhelmed with the fact that my cock was actually buried hilt deep inside of my sister… with my phone I actually took some short videos of the amazing moment. As I slid in and out of her, I watched her as I could see her pleasure on her face… She felt unbelievable… As I was sliding in and out of her drenched pussy… she muttered the words “you feel good” to which my only response was “so do you” followed by a “thank you”. I continued to pound away at her as her legs were in the air, over my shoulders. Then I noticed that you could see and feel my cock inside her just above her pelvis… I could see myself every time I buried it deep inside her… I commented about how hot I thought that was and she agreed, then mentioned that I was hitting her g-spot with every thrust and that she was going to cum. I continued to penetrate her as her pussy came all over my cock… as that happened I couldn’t take it any more… I was about to explode. Regrettably I could not shoot my huge hot thick load inside of her as (as I previously mentioned) she was married… I pulled my cum drenched cock out of her pussy and began to explode into my hand, since I had no other options… I have never cum as much or as hard as I did just then with my sister. She has since told me that she enjoyed it, though cumming all over my cock kind of tipped me off. She had also said that this is a one time deal… that is a depressing thought… I can only hope that she liked it enough to want it again… Regardless… my fantasy of over 20 years came true and I can say now that my cock has found where it wishes it could be every day.
Even if I never get to feel my sister’s pussy wrapped around her brother’s cock again, I can say honestly that my biggest sexual fantasy has been fulfilled… I only hope that in the future I get the chance to penetrate her once again and maybe even fill her with my cum… how I would love to watch it drip out of her. I love my sister and now, based on experience, I love being intimate with her. I don’t know if I will ever get the chance again, but I will continue to hope that one day I may have the privilege to fill her with the love and the cum that I so desperately yearn to give her.
So that is it… that is the story of a fantasy come true. It is my first an maybe only story. I welcome your responses and your feelings on the story… it is after all the truest story I have ever told… I would love to hear advice and any comments… Thank you for your time.