How many of us have often thought woulda, coulda, shoulda, and dreamt of being able to turn back the clock to do it all over again, but differently? The last twenty seven years of my life have involved that kind of thing, but since I can’t time travel, I am stuck with nothing but regrets. My name is Tim and I just turned forty, and I suppose that it is fairly common when a person hits that age milestone, they look back on the years that got away from them, and only remember the regrets.
My big regret involved my sister Sarah, who is a year older than me, and dates back to when I was 13 years old. I was mentally immature for my age back then, but my body physically had matured so well, that I became addicted to sex. Well, maybe that might be an exaggeration, but I was hornier than anyone I knew, and my pecker, as well as any pussy I could visualize, were constantly on my mind. I’m sure that I jerked off more than most kids, and figured out just about every imaginable way to pleasure my pecker. I had been caught jerking off by my mother, two of my aunts and almost by Sarah, my 14 year old sister. When Sarah and I were younger, we played games that inevitably led to showing our privates, touching, etc., but nothing hot and heavy. Even at age 14, she sometimes joked with me about some of the stuff we used to do, and I would usually jerk off after she talked about it. I never felt that she brought it up to initiate anything, and I’m not even sure she knew it got me worked up. When she talked about it, I would cover my erection, so she wouldn’t see it.
One of the times that Sarah joked about us exposing ourselves when we were younger, I said to her “Sarah, it’s too bad we can’t still do those things, because I would love to see you naked now that you have developed into a sexy young hottie”. She laughed and said “Tim, we are not ten years old anymore, and besides where would be able to do those things, without being discovered by somebody”? We were in the family room in the basement, and my parents were one floor up in the living room, so I would have done it right there, but I knew Sarah would be too afraid of getting caught. My erection was telling me to keep this conversation going, so I got really brave and said “Look what has happened to me just talking about what we used to do”, as I pointed to my bulging shorts. Sarah glanced down at the tent in my shorts, and said “Holy shit Tim; it sure seems a lot bigger than what I remember”. Being immature, I said “look closer and you can see how big it has got”, as I pulled the waistband of my shorts down enough for my pecker to pop out. It was only six inches long, but back then, most kids figured they had the biggest in town, and I was no different.
Sarah was caught off guard at my boldness, and although she stared at my pecker for a few seconds, she then said “oh my god Tim, what the hell are you doing”? She bolted up the stairs, and there I sat with my pecker sticking out, and no way to do anything with it. I put it away and waited until it deflated, then I went up to my room on the top level, to get ready to masturbate. I dropped my shorts and briefs and sat on the edge of my bed, stroking my pecker, as I thought back to Sarah’s reaction. I guess you could only classify it as outright rejection, so it wasn’t easy lathering up a load of sperm. I heard a knock at my door, so I pulled my shorts up in a hurry, and then said “come in”. It was Sarah and when she asked me what I was doing, I said “I was thinking of you and had to masturbate, so here I am”. Sarah said “I didn’t even show you anything so why would you be doing this”? Before I could answer her, she went on to say “so did you already masturbate or were you just about to start when I knocked”?
I told her that I had just started, but had to stop when she knocked. Sarah said “okay, mom and dad just went grocery shopping and will be gone for an hour or two, so I guess I owe you a look. I will show you my body and watch you masturbate, but nothing else”. We left my bedroom door open, so we could hear if mom and dad came back, so I dropped my shorts and Sarah lifted up her tank top, and dropped her shorts and panties. Because of the conversation, I was rock hard, so when my shorts were pulled down over my pecker, it bounced a couple of times, and Sarah found this funny. There was nothing funny about the beautiful tits and pussy in front of me, and I wondered if I would be able to keep from shooting my load right then. I said to Sarah “I can’t believe how beautiful you are, and I am so thankful that you decided to show me your body”.
Sarah said that I should get started since we really didn’t know how much time we had, so I started stroking my pecker. I asked her if she could sit on my bed with me so I had a better view and she reluctantly sat down. She watched intently as I stroked, and then she said “what is the wet stuff on the end of your thingy”? I said “it’s called pre-cum, and it’s for lubrication to help with masturbation and sex”. Sarah was sitting on my left, and I was trying to edge closer to her, hoping to get a quick touch of her tit, and as my left arm grazed her nipple, she jumped up, got dressed and left my room. I finished jerking off and shot a huge load all over the floor, and then went for paper towels to clean up. I was surprised when she came back in to my room, and said “I guess you are finished already. That’s too bad, but I warned you that there would be nothing else going on and you didn’t listen”. I said “Sarah, I’m sorry that I upset you, but the sight of your body got me so worked up, I had a hard time controlling myself. Do you have any idea how hot you are “?
Sarah smiled and said that she was flattered, but asked me to stop exaggerating. She said that she had probably overreacted earlier, so if I wanted to masturbate again, she would strip and sit with me. It didn’t take long for my shorts to hit the floor, and I was already stroking by the time she sat down. What was interesting was the fact that Sarah sat even closer to me this time, and her tit made contact with my arm right off the bat. Our thighs were also touching, so I was getting worked up into a frenzy. My right hand pumped furiously on my pecker, and I said “watch Sarah, it’s going to shoot”. Sarah bent over slightly to watch me shoot, so the first stream just missed her face, but the second and third landed on her thighs. I thought that I would get in trouble, but she touched it with her fingers, and said “This stuff is pretty slimy”. Her tit was still touching my arm, and my cock didn’t deflate like it usually would, so I continued stroking. Sarah said “I thought you were finished”. I said “your tit was touching my arm, and our bare thighs were touching so my cock wants to continue”. She laughed and said “I can’t imagine what your cock would do if I actually let you touch me”.
I wanted to say “let’s find out”, but I figured that I better not push my luck. Sarah must have been feeling a little aroused because her attitude seemed to change. She said to me ‘I’ll tell you what. You let me stroke your cock this time, and I will let you touch me”. I was getting to the point of no return, and began to think that maybe we should call it a day before I ended up raping her or something.
Before I had a chance to consider anything, Sarah reached over and took hold of my cock, and she placed my hand on her tit. She squirmed when I played with her nipple, and she began stroking my cock. I found our positions to be a little awkward, so I suggested that we take off our clothes completely, and lie down. I said “don’t worry; I’m not going to do anything stupid. I just figured if we were going to do this, why shouldn’t we be comfortable.
I was very surprised that Sarah agreed to it, but she removed everything and lay back on my bed. I moved beside her on my side, so that I had my right hand free to feel her body. I took her right hand and placed it on my cock, and then I began exploring her beautiful body. Thinking back, I wish I had known more about the female body, and I might have had more success with Sarah. I had a great time with both of her tits, but I wanted more. I wasn’t sure if Sarah had counted on me touching her pussy, but I wasn’t going to miss this opportunity, so began moving my hand lower.
My hand reached her pubic hair, and when she didn’t resist, I continued downwards and put my hand on her pussy. I rubbed it awkwardly, and tried to get my fingers inside, and just when she started parting her legs, seemingly to give me access, my cock started shooting cum. Sarah sat up a bit, and said “that little feel of my pussy sure got your cock shooting in a hurry”. She still held it, as it shot stream after stream onto her stomach area, and she gazed at the pools of cum with a curious stare. I apologized for getting her all wet, and then got up for paper towels. I wiped her down, and then she got up and began putting her clothes back on, as I began to feel a little down, thinking that this kind of opportunity may never happen again. Sarah was walking out of my bedroom, when I asked her to wait so I could ask her something. She stopped and turned around and asked what I wanted. I said “Sarah this was so fantastic; is there any chance we could do this again sometime”? Typical of a girl; she said “Maybe, but I’ll have to think about it”.
A few weeks went by and there hadn’t been any opportunities for me to ask her, at least none with us alone in the house, and I was starting to get very frustrated. My parents were going to a company barbecue this Saturday, and Sarah and I chose not to go, so I figured this would be my big chance to get her alone for a repeat performance. Four days and counting; I hoped that the time would go by fast, since I was masturbating three times a day just thinking about it. Friday night Sarah came to my room and asked me what I had planned for Saturday, because she was going to invite a friend over if I didn’t mind. I said that mom and dad were leaving at noon, and I had no plans, except that I was hoping her and I could spend some fun time together since we had the house to ourselves. She smiled at me and said “you horny little bugger; you want to get me naked again, don’t you”? I said that I had been dreaming about her for weeks and couldn’t stop thinking about our last time together.
After a minute of deliberation, Sarah said that she would make my dreams come true, if I promised to obey her rules and only do what she says. I agreed and said “it’s a deal sis, so what time can we start tomorrow”? She said “aren’t you the impatient one; are you sure that you can last until then”? I walked over to her and touched her pussy through her shorts and said “with this beautiful pussy to look forward to, I can wait”. Sarah gave my cock a little grope through my shorts and then took my hand from her pussy and said “1pm tomorrow in my room and don’t be late”.
When I got back to my room, I didn’t know how I would stay sane thinking about 1pm tomorrow, and how I would kill time until then. I guess I would just have to be patient.