Long Time Cumming-best Friends Sister

Posted by: Age: 45 Posted on: 1 comments
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This story takes place in my mid twenties, but started long before that. My best friend Bob and I did everything together, from school to boy scouts. From time to time we would sleep over each others house, at the time I was about 13 years old. Bob had an older sister we will call Ann, she had recently moved back home with her son. I know it was hard for her to come home after a rocky relationship, and a young child. Her boyfriend was a piece of shit, could not hold a job, and was very abusive.



While sleeping over at Bobs house one night, I woke up around 3am with a raging hardon. I went to the bathroom to take a leak hoping this would relieve my situation. No such luck, my teenage hormones were in an uproar and there was only one thing that was going to help. I got out of bed quietly, and snuck back to the bathroom for a quick wank. I went in shut the door and started at it, I was in such a rush to wank that I didn't lock the door. Now I am minutes from cumming and the door flies open, there I am dick in hand stroking for all I was worth. It was Bob's sister Ann, I was so embarrassed, I almost cried on the spot. I tried to cover myself with my hands, and pull my pants up.



At this point tears are running down my face, Ann tells me to keep quiet and grabs me by the hand and takes me to her room. At this point I am scared shitless, my mind was running wild. My biggest fear is that she would rat me out to her parents. She sits me down trying to calm me down, telling me it was all right, that all teenagers did it. Now she's holding my hand, dressed in a tee shirt and when she sat down I realized she was not wearing any underwear. Let's see a 13 year old boy a half naked woman, boing, instant hardon poking out of the top of my underwear!



Ann looks down at my pants and I think she was feeling sorry for me, without saying a word she pulls her tee shirt off, stands me up and pulls my underwear down to my ankles. Never being with anybody besides myself I thought I was going to cum on the spot, my heart was racing. Then she slowly started to stroke me, god I thought I was in heaven. I knew by the feeling in my balls building it would not be long. Then that's when it happened, the baby started crying and Ann heard her mother's voice from down the hall 'is everything ok' faster than I could blink my eyes she pulled my pants up and whispered for me to go back to bed, answering her mother 'every things all fine.'



Needless to say I didn't get any sleep that night nor did I cum. But when I got home I wanked three times in a row, and used that as one of my best memories while masturbating for many years.



But this is not how it ends. Turn the clock forward 12 years. I am still single and have bought a small house. Come to find out Ann and her husband live two houses over from where I bought my house. We chatted a few times but never talked about what almost happened when we were younger. Besides I was in a pretty serious relationship of two years and engaged, and she was married.



Six months later I found out my girlfriend was cheating on me, and for me that was it, no going back. Shortly after that Ann caught her husband banging their baby sitter who was a minor, 16 at the time. Needless to say she was heading for a divorce. About four months had passed, things were quieting down for me, I was glad it happened before we were married and was moving on with my life. One Friday night after work, I was out working in the yard cutting grass and trimming out. When I was done I called for a pizza and hit the shower. After the shower I was sitting on the porch having a drink waiting for my pizza.



I hear a knock at the front door, I grab my money on my way through the house only to find out it was Ann. I invited her in, in the mean time the pizza shows up. I offered her pizza and a drink and to my surprise she says yes. Her mother was taking her kids to the beach for the weekend. After eating, both of us were starting to loosen up. Then it happened, she says... 'remember when'... and we both started laughing !! I told her that she was a huge part of my teenage masturbation sessions. That's when my jaw hit the floor, she asked me if she could finish what she started. Of course I said yes, not having had been with anyone since the breakup. But there were conditions, Ann was going through a nasty divorce and did not want sex, she said she was not ready for that so I agreed.



We went into the bedroom and stripped both of us giggling. We lay side by side naked, kissing and I was highly aroused (she looked great). Then she started stroking me gently and I was fingering her. My mind drifted back to that night, our pace soon quickened and her breathing became heavy. She was soon cumming, and I was also experiencing my first squirter, as she proceeded to soak me my bed and the wall. At this point I was ready to explode, which I did, the first stream hit her in the chin and each of the following a little shorter, it had been a long time since I have cum that hard. When we caught our breath we looked at each other both covered in cum (hers and mine) and laughed about the mess we had made. It was really good to finally complete my teenage memory. This led to much more which is not appropriate for this site.

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