My Sister Jill

Story Info
Or, how I love to masturbate.
12.1k words
4.35
103.8k
20
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

When I was 18, my sister Jill, who is two years older than me, had two of her friends over to our house. One of them, Donna, was always flirting with me and I loved it, even though it was driving me crazy.

It was her breasts. They were the biggest and the best I had ever seen. When no one else was looking she would make sure that I would notice them and notice them I would.

She would make me so hard, that I was torn between never wanting to take my eyes off of them and going to the bathroom, locking the door, and taking my pants down to my ankles, wrapping my hand around my cock and stroking it till I came.

Actually, it was with Donna's image that I had my first ever orgasm, just earlier that year. I though that I had never felt anything quite so good, so I did it again and again. I was possessed with doing it.

And here I was, with Donna in the house, showing them off to me again. She had on an elastic halter-top that didn't leave anything to the imagination. I was basically staring at them when my sister caught me and told me to leave them alone. I left and went down to the rec. room in our basement, to watch TV and to be alone, alone enough to put my hand down my pants and keep my hard going. Just as I started to have those good feelings, I heard, "It looks like you're having fun."

It was Donna. I jerked my hand out of my pants and started stammering, unable to say anything. She walked over to me and put one of her feet on top of my groin and started lightly moving it. "Look" she said, and with that, she took hold of the top of her halter-top and slowly started dragging it down. She started showing more and more cleavage, more and more of the tops of her breasts. I was seeing more breast than I had ever seen before. A little more I would be seeing here nipples.

At that point, we heard a noise from upstairs and she looked at the stairs, realizing that it wouldn't take much to be discovered. She reached down and grabbed my hand and said come with me and literally drug me over to a corner of the room where we wouldn't be seen. She asked me if I would like to kiss her. At this point in my life I had no confidence in myself when it came to girls, I had never kissed one romantically and here I was with the girl of my dreams, the girl that I beat off to. Even though I was hesitant, she wasn't and leaned into me and gave me my first kiss. She hadn't let go of my hand and as we were kissing, she brought it up to her breast and put my hand on it.

I had never felt anything so good. God, my cock was throbbing so much, it had never felt harder and I knew I wouldn’t be able to take much more of this. But, I also never wanted it to stop. And then Donna pulled her top down and exposed her naked breasts to me. She also started moving her hips into me, rubbing my cock. I was touching naked female flesh for the first time and having her taking me over the edge, with just her body movement. I couldn't help it, I was so close and everything felt so great, there was no way that I was going to stop the sensations and I started coming.

And just as I was, Donna screamed, "stop it you pervert" and pushed me away from her, while pulling up her top. And there was my sister, Jill, taking it all in. Knowing with out a doubt that I had somehow, attacked one of her best friends.

Talk about the shit hitting the fan. First of all my sister is bigger than she and me came up to me and kicked me as hard as she could and then starting hitting me. Only when she got tired did she stop and then started crying and took Donna in her arms, who now was also crying. Then Jill started yelling at me, about me being a pervert and how sick I was and just wait till she tells mom and dad.

Well, my carefree life ended right there. Jill did tell our parents and dad did punish me. First with a whipping that I never will forget and then he basically grounded me. I was forbidden to date or have any contact with the opposite sex. It was probably just as well, because the story of what had happened was all over town in a matter of days. I was known as the pervert.

Yeah, I still liked to whack off, when I had a chance. But, I was closely watched at home, and never given much of a chance. I had to leave my bedroom door open now, because I shouldn't have "anything to hide." My sister and I never got along at all after what had happened. In fact, we had terrible fights up until the time she left for college.

My job was doing maintenance and clean up work in the local factory. The last couple of hours though, the factory shut down and there were only a few of us there, doing the clean up. It was at this time that I would go into the bathroom and do my thing. It was almost like a ritual, every day about the same time; I would go in there and stroke myself off. I loved the feeling and I like to watch myself cum, watching it spurt, feeling the load come out. I would do it a hundred times a day if I could.

Little did I realize that my habit brought notice, not at first but later. Our restroom had 6 stalls in it and I was in there for about a half an hour at a time. Well evidently, I wasn't the only one there, who liked to do their thing, because one day when I thought I was in there alone, I heard the sounds of someone else doing what I loved doing. The sounds were unmistakable. Even though, I was extremely excited knowing that there was someone next to me doing the same thing, it was also scary to me. I couldn't continue and was torn between leaving then and trying to see who came out or continue listening to him jacking off.

Then there came silence.

And then a voice, "why did you stop?"

I was too scared to answer.

He said, "It's better for me when I hear you and knowing we're doing the same thing."

I now knew it was Brian. He was about six years older and we had become friends. But, this was too much. I had gotten caught and the label of pervert put on me earlier and I didn't want the same thing again. But, still this was exciting.

Just then, I heard him walking over to my stall and he gave my door a knock, "Open it up for a second" he said. I first pushed my hard dick down between my legs and closed them together, so he couldn't see it and then I opened the door, not knowing what would happen, but excited with some unknown possibility.

There he stood, with a bulge in his pants and then he asked me, if I would promise not to say anything to anybody. "About what," I said.

"About this" he said. And with that he slowly started unzipping his pants, looking into my eyes, for any sign to stop. Instead of a sign to stop, I took my eyes from his and lowered them to his groin. After he unzipped himself, he put his hand inside of his pants and then he hesitated. I knew he had his hand around his dick and was ready to bring it out.

"OK," he asked?

"Yes," I managed to squeak out.

And with that he pulled his dick out and started to stroke it.

"Do you think it's a nice one," he asked?

I again managed a squeaky yes.

His cock was unlike mine. His was long and skinny, but it had a really big purple head on it. It looked like it was made for stroking, which he did.

"Do you like watching me?"

I could only nod.

"Can I cum? Do you want to watch me cum?"

At this point I couldn't do anything, not even swallow.

"You have to help me," he said.

I looked up at him, afraid of what he meant.

"Let me see yours."

My cock, at this point, was hurting me. I was extremely hard and it was pushed down in a very uncomfortable position. I wanted the relief, in more than one way. With just a little movement from my legs, my cock popped up. I reached down and grabbed hold of it, down by the base and finished bring it up in all its glory. It felt harder than it ever had did, and so I started stroking it. I had to.

When Brian saw me, his legs just about gave way and he had to reach up and grab the top of the door to steady himself. And then he started chanting, "oh God, oh God, oh fuck, oh fuck." And, then after a few moments of that, it was "I'm going to cum, oh fuck, fuck, fuck, oh God.

And then with that his dick got even bigger, redder, his body started to jerk around and then he unloaded the biggest wad I have ever seen, twice anything I have ever done. He blew his wad all over the door and the floor and it appeared it was all he could do to remain standing. He slowly backed upped to where he could rest against one of the sinks.

He was watching me the whole time and after a minute he was back on his feet moving toward me. "I want to watch you, you have a good big one, stroke it, make yourself cum. Just think how good it will feel to cum like I did." Even though he had just had a huge orgasm, he was stroking himself again. It was all too much; I was getting those tingly feeling in my balls that I knew meant that my time was near.

Usually, when I'm by myself, I turn around and drop my load in the toilet bowl, but not this time, I wanted to watch Brian some more and I wanted him to see me, I knew I had a big load myself coming. And then it was on me. That first spurt, I swear, went three feet straight up in the air, most of the rest, ended up on my stomach and ran down my cock, into my pubs and on my balls. Oh, it was so good.

But then reality started sinking in. There were other guys outside, in the plant and any one of them could have walked in on us and still could. I was starting to get scared. What if Brian was gay and wanting to do more? I didn't want him touching me or him making me do something to him.

But, Brian just said thanks and that he would clean up and for me to go ahead and get back to work.

I was out of there in a heartbeat.

*****

It was a couple of weeks later, before I even tried to go into that rest room again and I also kept my distance from Brian. I 'm not sure why, because I did find the whole thing exciting, but I was afraid that he might want to do something queer and I wasn't ready for any thing like that. Even though watching him get off was the most exciting thing I had ever done.

I had tried to hold off jacking off at work, and resorted to playing with myself on the drive home, but there never did seem to be enough time to get off, so I was continually in a state of arousal.

At school I would leave some of my classes to go to the rest room and tried to get off there, but I would get interrupted from other kids, so I quite trying there.

So, I decided to revert back to my habit of whacking off at work. I did this a couple of times, without seeing Brian, even though I guess I would have liked something to happen.

After refraining as long as I had, it felt so good. A couple of times I did it twice.

One day, after I had just gotten to work, Brian came up to me and asked me to meet him by the storage room, just before the next break. He wanted to show me something. I was hesitant, because of what may happen and also because with all the people around, we could get caught.

It was all I could think of though; I felt like I could hardly breath. I couldn't help myself; I was drawn to the storage area. I saw Brian already there, just as the signal for the break sounded. He motioned for me to come with him and to be quite. We entered the room and I followed him to a corner. He whispered in my ear, "see where the electrical cables run through the wall there, be real quite and look through that opening in a minute or two."

It wasn't but a minute, when I heard somebody talking, so I looked and I saw Wendy and Ryan. They work in the parts department and hardly ever came out on the floor. But, there they were, in the electrical closet, starting to make out.

Then with out hardly any preliminaries, Wendy just dropped down on her knees, unzipped his fly, took his cock out and started sucking on it.

I couldn't believe it. Wendy was not a beauty by some standards, but had a hard body, with nice breast and a tight ass. I could feel myself throbbing, I was so hard. I looked over to Brian; he was looking through another spot and had his cock out jacking it. I started rubbing mine, not taking it out, but through my clothes. I didn't know what I wanted, other than to watch the couple in front of me. This was the first time I ever saw a girl do anything like this; I couldn't believe what she was doing to his cock and I could only imagine how it must feel.

In just a moment, Wendy got up off her knees and started undoing her belt and the top of her pants. Having done that she lowered them and then bent over a table, while Ryan, moved in behind her and stared doing her doggy style.

This was by far the most erotic thing I have ever seen, but still I looked away, to watch Brian. He was really going at it, with that pecker of his. It was too much for me. If I didn't take my cock out, I was going to come in my pants. I unzipped them and for a moment had trouble taking it out. God it was stiff, but oh did it feel good when I started stroking it. I could get enough. Being with Brian, both of us jacking off, while watching the two fuckers fuck. I just wished I could see her boobs. But who was I to complain.

I couldn't see much of her pussy, because of my angle, but he had his hands on her hips, holding her, while he did her. He had to, she was moving all over the place. I saw her move one of her hands between her legs, I though maybe she was going to play with her self, but she was playing with his balls.

Just then I heard him say that he was getting ready to cum and with that she turned around and took him in her mouth again. I could tell he was coming, with all the grunting and the way he went spastic.

Between watching and wanting to hold off, I had stopped jacking myself, but I was so close to cumming. I looked at Brian and he had slowed down also. He held his finger up to his lips, indicating for me to be quite.

In a few moments they were gone and I started to put my cock away. Brian said, "Don't." And he started stroking him self again. He asked me what I though about it and I told him it was the hottest thing I had ever seen. I then asked him how he knew about it. He told me that years ago, he and Wendy, used to get it on in there, but she ended up getting married and wanted to try and remain faithful to her husband. But, lately, he noticed her and Ryan, becoming friendly. They still talked some and Wendy said that Ryan would help her out some financially and with her promotions. All it took from her, was a once a week, quickie.

"She knows that I probably am in here watching and jacking off. It's been our secret. We're two of a kind, we both love sex and getting off. Sometimes, she will stay in there and do her self.

I asked if he ever did her any more and he said no. That Wendy said having one boy friend, other than her husband, was bad enough.

Brian told me, that what ever I do, don't let her know that you're in here watching her, because it will ruin it for the both of us.

Just then, the break signal sounded again and we had to stop. I needed to just let loose and cum, but our time was up. Brian said, "meet me in the restroom, in an hour, that is if you can wait that long.

So that started a "friendship" with Brian. Not every day, but most we would get together in the restroom and watch each other whack off. That is except when we were watching Wendy. Their routine was almost always the same as that first day. Every once in a while she would lift up her top and he would suck on her nipples. I would close my eyes and think about her, in there doing what she did.

Brian never made a move on me, never touched me, even though in the storage closet, as close as we were, I thought about it. Just to see what his cock would feel like, especially when he was cumming.

*********

About a month later, as I was walking in the door, Brian came up to me and said that he was told about a repair part that need to be picked up and we needed to go get it. It was in Kansas City, about an hour and a half drive away. We took one of the company's trucks and took off. When we got there we found out that the part, even though was ready, and had to be moved, to where it could be loaded. After asking how long it would be, Brian told him that we were going to get some thing to eat and would be back in a couple of hours.

As we were driving away, Brian asked me if I had ever been to an adult movie theater. I told him I didn't even know that they were any around here. Well the next thing I knew, we were walking in the front door of one. Just follow me and be quit, Brian told me. He paid for us and we walked to the rear of the place and through the curtains.

All I could see was the movie, it was so dark. in there. Up on the screen, was a girl giving head to this guy, who had the biggest dick I had ever seen. I didn't know that they got that big.

I couldn't believe it, within ten seconds, I was supporting a hard on. Brian was just standing there. Then he told me, we had to wait for a minute for our eyes to adjust to the darkness, so we could find a seat.

I told him that I could see a lot of empty seats down in front, where the screen was illuminating them. But, Brian said no, just wait, we need to sit in the back.

Just then, I heard somebody speak out, " you can move on over, there isn't anybody there, till you're about in the middle." Brian then said, "come on" to me and then louder, "thanks," to who ever spoke up.

After we found our seats, Brian told me, " you think there is good action up there, just wait." "Wait for what," I asked. "Till you can see," he said, chuckling "and hear."

Hell, all I needed to see, was the action on the screen. Another girl had joined in and was playing with the first girl's pussy.

Brian then leaned over to me and asked, "are you hard yet?" All I could do was nod. He then told me, "don't be afraid to take it out and play with it." I looked at him like he was crazy, and he said, "what do you think everyone else is doing?" And with that, I heard the unmistakable sound of his zipper going down.

Even though it was still dark, I could make out, him pulling his cock out of his pants and then starting to jack off right there. With that I gasped, I couldn't believe he was exposing himself, where anybody could happen to see. "When you can, just look around, to the other seats," he said.

In just a few minutes I understood. Guys and only guys were in there, mainly in the back two rows of the theater. Some by them selves, some in pairs, but all with their cocks out. Some of them, which were sitting in pairs, were jacking each other off. Just then I saw one of the guys, lean over and take a cock in his mouth.

I didn't know what was the most exciting, what was up on the screen or what was taking place all around me.

Brian then told me, "you need to take yours out. You need to join in. It kind of makes them nervous, when you don't." I asked Brian, "Is everybody gay, here?" "No," he said. Some are just doing it, like us, because it's fun and it feels good. Others because they're lonely."

So with some apprehension and some relief, I took my cock out of my pants and joined in with the rest of them. I didn't know what to make of Brian though. Did he do this kind of thing much? Did he like guys? Was he going to be like some of the other guys around and grab me?

Just then somebody came down our row and tried to get by us, in doing so, he grabbed my dick and said it was a nice one. I jumped and knocked his hand away. He moved on and did the same to Brian. But, Brian let him play a while, then told the guy, that he was just here to watch and thanks anyway. So the guy moved on.

Brian then asked me what I thought of some guy doing that to me, I replied that it had surprised me and was like what he said, it was fun to just watch. I told him that I liked girls better. Brian said that it wasn't about girls or boys, it was about being around others who, like us, were having fun and getting off, with out any complications.