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How It All Started For Me

"I would never had thought this would happen"

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It all started when I was a teen boy. Our grandmother came to visit and she had to sleep in my sisters room. So that meant that my sister had to sleep in my room with me. She was 3 years older than I was. It was summer time and very hot out. Of course we had no AC to keep cool. I liked to sleep in my underwear to try to keep cool and she wore just a pair of panties and a T shirt. As I got into bed my sister went to the bathroom and turned the light off in the room as she left. After a few minutes she returned laughing and clearly hiding something behind her back. She jumped into bed and what ever she had she hid under her pillow.

After a few minutes she told me she found a pair of our mom's panties and bra in the bathroom. It was no big deal mom left them in there all the time. So I asked her what the big deal was? As she started to laugh to said she wanted to see me put them on. Of course I got mad and said no way. My sister kept nagging me and begging me to. I held my ground and told her no time and time. Then she pulled out her black mail card on me. A few weeks earlier she caught me looking threw her girlfriends clothes and sniffing her panties. So now I was even madder then before, simply because I knew I had to give in or I was in big trouble.

 So I got up out of bed and told her to give them to me, as I started heading for the door she stopped me and said NO, right here I want to see. I was not going to fight it was late and very hot. I figured that if I did it and got it over with I could try to get some sleep. So I turned by back pulled my underwear off and put mom's panties on. As I turned my sister was laughing and told me now the bra. So I put the bra on and she told me to come over to her so she could hook the back. I did what I was told to do. So I took a step back raised my arms and asked her if she was happy now? All hot , embarrassed and really mad now I was so happy it was over.

She told me how cute I looked and asked if I liked it. Of course I did not like it. I felt and like a complete fool. So I asked her if I was done now and if I could put my underwear back on. When she went to reply back she said first she had one questions to ask me and I had to tell her the Truth. I said what ever hurry up and asked. She asked me how long I was playing with myself and if I like it. Of course I lied and told her I was not jerking off and had no idea what she was talking about. She told me I was lying and she could prove it to me. I asked her how??? Very easy she replied!! Last Saturday when mom and dad went out and I was out with my friends you watched a Porn movie ( she told me the name of it, not sure if I can say the name here with out breaking any rules).. Any way I nearly fell over and did say to her so what if I did. The big deal she told me was that she walked in and I did not hear her and she saw me sitting there naked jerking off . She told me that I must have either been paranoid or heard her because I turned my head and she walked away and did not see or know if I finished.

Now that I was really embarrassed and I know I had to be red in the face I could not believe that I could feel myself getting hard. My sister noticed that my dick was getting hard and started laughing. She asked if I liked being in the panties or that she saw me naked playing with myself. I did not know what to say or do at that point. So I took off the bra and as I did she said to stop hold on a minute. As I tried to be quiet and argue no with her she said please juts hold on one minute real quick. So I stopped and said What?? She said if I leave it on she had a surprise for me. I asked what and she said I had to leave it on and promise not to take it off and she would show me my surprise. So now I had to know what she had in mind. So I did as she asked, even though I should have known better she was most likely setting me up again. So I said give me my surprise and I held out my hands. She said OK here goes, as I stood there with my hand out in mom's panties and bra waiting, I could not believe what she was doing. My sister took off her T shirt ans was sitting on my bed in just her panties and nothing else. Now my stiff dick just got hard so fast and the top was peeking out of the panties I had on.

She smiled and asked if I liked what I saw? I did not know what to say or do and all of a sudden I just blurted out YES. There was my sister showing me her tits, I knew they were big and had to be nice but never did I think I would see them. She asked if I would jerk off looking at her? Again I blurted out YES. She was laughing and said she wanted to see me jerk off again but this time she wanted to see me cum, unlike last week she did not get to see me finish now she wanted to. I wanted to so bad but did get some since to say no way it is not right and I am embarrassed to do it in front of her. As I was telling her this she was rubbing her tits and licking them for me to see. My dick was starting to hurt just like the first time I jerked off I wanted to do it and relieve myself. Now she said maybe this would help and she started rubbing her pussy over her panties and I was ready to loose all control.

How I was holding back I have no clue to this day. As I was ready to give in she removed her panties and asked if this would help me to jerk off now.There was my older sister, nice dark tan with no tan lines big ass tits and a very nice trimmed pussy. It did not matter any more I had to do it, I did not care what I had on or who may walk in I started jerking off and in no time at all I cam in and all over my mom's panties.

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I did not even realize that while doing this my sister was playing with herself and with in a few seconds after me she was cumming herself. What a rush and thrill, I did not even realize at this point what just had happened. It felt so good a real life girl naked and me jerking off. My sister jumped up out of bed ran to the bathroom and came back with some wet towels and started clean me off. She told me to get out of mom's panties and bra and she would tale care of them. So I did what she said to do she took off and came back a few minutes later.

After she came back she give me a kiss and asked if I liked what we just did? Off course I did but we can get into big trouble if we get caught. She told me not to worry, relax and just enjoy the moment for now. She walked over to the bed grabbed her panties she was wearing and said to me here put these on. I want you to wear my panties tonight to sleep in. I asked what she was going to wear? She said her T shirt, what else? We climbed into bed , me in her panties and her in just her T shirt.

As I lay there all worried and scared of what just happened she told me to forget about it and not to worry again. I asked how can I do that? I am wearing your panties after jerking off for you in Mom's panties and bra learning you have seen me before doing it and you have no clothes on!!! She just laughed and said if she can help me would I calm down and not worry. Of course I would if you could help me.. I figured that she was going to tell me something nice or funny to put me at ease. Instead she asked me who's panties do I like better, hers or mom's? I nearly screamed when she said that. She told me all she wanted to do is ask a simple question? Of course now still being scared and all I could feel myself getting hard again.As she said well, who's I could feel her hand rubbing her hand on my crotch area over her panties. I was rock hard and in fear of what to do.

I laid there just letting her do what she wanted. As she rubbed my hard dick through her panties she asked if I liked how it felt. Yes I like it.. I felt her grab my hand with her other hand and she started to move it. I could feel that she was laying my hand on her body and I could feel her skin. I was not sure what to do or if I should even say anything. I did not want to ruin anything or even get caught. But I had to know what was going to happen next. As she rubbed my hand on her leg moving it up and down I could feel a small amount of hair. It had to be her pussy that she was running my hand over. As I went to look she told me no looking just touching only. She guided my hand between her legs and told me to feel her all I wanted to she will not stop me. As she was saying this she was still rubbing my hard dick in her panties. I knew I was going to cum again and soon , I was afraid that if I did not act now I would never have the chance again and if I cum to soon she may stop me. I started to rub her pussy and I could feel it getting all wet. She started to moan and just like she did and I have seen in porn movies I went for it and tried to put my finger in her pussy, with my hands shaking and no clue what I was doing she said here let me, She told me to relax my had and let her do it, she took my finger and guided it into her pussy. Once my finger found the entrance of her pussy it slid right in and she moaned.

She told me to just keep sliding my finger in and out and do not stop. I did as I was told to do she was moaning and twitching all over the place I could feel my had was soaking wet and getting wetter, At the same time she was stroking me faster and faster, before I knew it I was cumming all over her hand and myself, it felt so good I started sliding my finger in and out of her faster and faster myself on her. My sister started bighting the pillow as I could feel her clinching her pussy on my finger. She was going nuts and I just kept going as she kept telling me not to stop, please do not stop keep going.. All of a sudden she just let out this big moan and a deep breath. I just made my own sister cum by fingering her. She jerked me off while I wore her panties. By this point I did not care any more and I was calm now and she was right she would make me feel allot better.

When my sister caught her breath she asked me if I was feeling better now. Of course I said yes with a big smile. She laughed and said so did she. She also said to be she was lying and never would have told dad about me sniffing her girlfriends panties, she just said that to scare me. She said she thought for sure I would never do what she wanted. But the more she told me what to do the more she got turned on and the whole thing was a joke that she never thought would lead to us watching and then helping each other to get off... At first I thought I was mad then I realized I just had sex for the first time and that is all I care about. She was happy that she was able to help me and to teach me herself.

We both got up cleaned ourselves up and got ready for bed again. As she handed me my underwear, I asked her if it was OK if I wore her panties to bed tonight? She replied only if she did not have to wear any? We laid down and as hot as it was she asked me to hold her in my arms. I did, she placed one hand on her breast and my other on her pussy. I started to get hard and I could feel it pressing on her ass. She laughed and said we need to sleep it will go away. No worries. Good night.... It was a very good night....
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Written by herbie327
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