- Sissy
My real name is Marie, but everyone calls me Sissy. As you probably know, Debbie is my younger sister by over two years. Until recently I really thought of her as a much younger sister, but in the last year or so I was very aware of her physical maturing. It's hard to believe, but I think that in the last few months, her breasts have become more developed than mine. Anyway my relationship changed with her on a night that I had come home from a date with Bobby. Usually, Bobby and I were able to find a private place to make out after we had gone out to a movie or some other kind of thing we did with our friends. Bobby and I had been having sex for the last six months or so. Bobby was my first experience, and I was his first. So you might say we were learning together. I had started the pill when I was sixteen, and I was very ready then, but either the opportunity never came along, or the guy was wrong. I don't want to get into a whole story of my history with Bobby. As far as I'm concerned the really interesting part of our sex lives really began that night.
We had been fooling around at my friend Nancy's house. You know, kind of listening to music in the fixed up basement and dancing a little. Nancy was with a guy she was not exactly thrilled to be with, so for Bobby and I to makeout by ourselves was definitely kind have awkward. We had been fooling around on a daybed in a little alcove near the oil burner and hot water heater. We were both very hot and bothered from doing a lot of kissing and touching. We had also smoked a joint just before we had gotten to Nancy's, and that's always a big turn on for me. Well it was clear that it was just going to be a bummer at Nancy's. She wanted us to be with them, since she absolutely didn't want to be alone with this guy. We decided to call it a night, and to put Nancy out of her misery, we offered to drive this guy home, since he lived close to Bobby. Bobby dropped me off. We were going to see each other the next day so it was hardly a tragedy. The three of us smoked another joint just down the block from my house. I had a very nice buzz as I kissed Bobby good night and said goodbye to the other kid. I was definitely feeling no pain as I walked into the house, and I was still pretty worked up from our little sexual groping at Nancy's. I could hear the TV sound coming from my folk's bedroom. I walked down the hall to their bedroom suite, poked my head in to say good night. I liked to do that to let them know I was home. They had fallen asleep watching the television. I found the remote, and turned the TV off. I climbed the carpeted stairs to get to my bedroom. Debbie's bedroom and mine were at the very end of the hall. Her room was on the left and my room on the right, with a shared bathroom in between. I could see a little light coming out from under Debbie's door. I was glad that she might be up. I was very awake and I was looking forward to some company. Certainly I usually knocked before I entered her room, but for whatever reason, I didn't that night, and was very glad I hadn't. As I opened the door, I was greeted by an amazing sight. I was looking at my sister naked legs wide apart as she was obviously masturbating. Her eyes were shut tight as she concentrated her right hand on her pussy and her left hand was inside her partially open pajama top, where she was obviously pulling at her left nipple. Her night table light was on low, but I could clearly see what she was doing. I was absolutely frozen. She had no idea I was there, and I suppose I could have slowly backed out of the room, but I didn't. For what seemed like forever, I watched her rather desperately try to get herself off. I must say at this point, I had not recently seen my sister undressed. I was struck by her obvious physical maturity. Her public hair was clearly thicker than mine was. Her breasts were also more developed, and I was two years older. I have to admit that in my somewhat stoned state; this sight both shocked and excited me. There was no question about it. I also now was becoming fearful of Debbie coming while I was watching. Somehow I felt that would make a difficult situation worse. Backing out seemed impossible now, so I simple knocked lightly on the slightly ajar door. Debbie's hands stopped moving and her eyes fluttered open. Even before she could say a word I said, "I'm sorry I disturbed you." There was a terrible pause, as Debbie simply looked frozen in place. I needed to take charge I quickly realized. "Look Debbie. I want you to know that I should have knocked, but I don't want you to be embarrassed. Believe me I do that all the time, and I'll probably do it myself tonight." I felt I needed to keep talking to try to take the sting of her embarrassment away. "Please don't feel bad, honestly I do it all the time, and I hope you do to." She hadn't moved when she simply and quietly asked me. "How long were you watching?" I thought being completely straight, would not really help, so I answered. "Well just enough to see what you were doing." She slowly removed her hands and brought her legs together. I continued. "You know Debbie, I know it's a kind of private thing but I have to tell you that I do it all the time, and especially after a night like this when I might fool around with Bobby and not have a chance to get off. Then I almost always do it as soon as I'm in bed or in the bath. So I really understand honey, I do." I was almost pleading with her. She finally said, with some irritation. "Alright Sissy, alright Sissy it's not the biggest deal in the world. I know that. I don't even think I'm doing it right. I'm not even sure I know what I'm doing. I hardly ever feel any big thing at the end, hardly ever." With those words she started to cry a little. I felt awful. But I also saw a way I might help. "Look Debbie nobody is born knowing how to do it. A lot of people learn from their friends. Sometimes badly. Believe me I know. Nancy showed me some years ago, and frankly she had no idea what she was doing, and I had to unlearn what she had taught me. Maybe I can show you. Would that make you uncomfortable? If it does we can skip the whole thing, but I think I can really help. What do you think?" She was looking more relaxed much to my relief. She pulled her legs back and gestured for me to sit down, which I gratefully did. "Oh Sissy, I would love that. In a million years I could never have asked. Sometimes I get really kind of excited. I don't even know what starts it. A few times it's been a scene in a movie or in a book, but a lot of the time it just happens especially when I'm lying in bed. That's when I try to do it. I know I can get myself very worked up. You know what I mean? But I rarely can get any real relief. Like just before, I just couldn't finish it off at all. So if you think you can help I would love that. It would be so great if you could." With that she reached over and gave me a hug. I can't tell you how pleased and relieved I was. Also, the grass I think was heightening a lot of my feelings. I hugged her in return. I didn't want to break the spell but I had to pee like crazy, so I told her that, and that I wanted to get comfortable. I almost leapt from the bed, went to our bathroom, and as I peed, began to undress. By the time I wiped myself, I was undressed. I slipped on my bathrobe, which was hanging behind the door and quickly slipped back in Debbie's room. This time I shut the door behind me and turned the lock. She seemed to be exactly where I had left her. "Wow, Sissy that was fast. Here sit down beside me. Ok Sissy, I admit I'm feeling a little shy, so you just do what you think will help. I promise I'll be your best student." At that idea, we both laughed a little but it sort of broke the ice too. I was thinking fast about how to go about this. I decided that I thought that maybe I would show her what I did. That way all she had to do in the beginning was watch. I told her my idea. She seemed both relieved and pleased at the same time. She got right into it. "Sissy, change places with me. I'll sit at the end of the bed so I can see you, ok?" We did, and I stretched out on her bed with her pillows behind my head, with Debbie at my feet. "Ok Debbie. I kind of have to get into it. I usually close my eyes and think sexy thoughts, like making out with Bobby or something like that. I try to make it as real as I can. You can use anything that turns you on. Whatever you like. I like to think of the head of Bobby's cock after I've sucked it a little and it's become very stiff. I love the way it looks then. It's very smooth and shiny. I can even see his heart beat in the vein that runs up his cock. One of my favorites is to imagine that Bobby is licking my pussy, That my finger is his tongue." I could see that Debbie was hanging on every word. I moved my robe aside and slightly lifted my legs and opened myself for Debbie to see clearly. "You see just from having those thoughts, and seeing you trying to get off, and even fooling around with Bobby just before I came home has made me wet. Can you see that? " I didn't expect her to answer, but she leaned over to look more closely. I took one hand and pulled my lips apart a little so she could see a little better. I placed my right index finger slowly into my vagina. "I'm going to get myself all wet and lubricated so I can get myself off without irritating myself." I added another finger, and began to moisten my labia, then up to my clitoral hood. I was definitely getting myself all worked up. I think having Debbie peering at my wet pussy was having its effect. I started to stroke myself a little faster. "Try not to be to rough, be very gentle. That way you can go on and on without irritating yourself. Keep your fingers nice and wet. You see?" I was really getting in the mood now, but I didn't want to come first. I kind of thought that would be unfair to Debbie. "I love to do also what you were doing. It really helps me to play with my nipples. I'll show you something else later, that's also good. I'm going to stop for a while. I don't want to get ahead of you. Let's switch places again. I want you to try it, and I'll help, alright?" As I sat up and moved, Debbie wordlessly took my place. She lay back, with her legs opened and her knee's slightly raised. She closed her eyes. "Ok, Sissy, I'm going to just think about things." I could clearly see than Debbie was even wetter than before, even if she was unaware of it. Even before she touched herself, I could see that she was quite aroused. Her labia were puffy and open. I could even see that her clitoris was now exposed. I must admit that seeing her so ready was having a very strong effect on me. I could even smell her arousal. I needed to say something. "Oh Debbie, I think you're very ready. You're nice and wet. That's a good sign. Can you feel it? " She just nodded her agreement. "This time I'll help you a little, ok?" Again she nodded. I softly touched her inner thigh. I heard her draw in her breath. I used both hands stroking her thighs, very slowly working my way closer to her wide-open pussy. She reacted by opening her legs even wider. The pink opening to her vagina was like a target. "Debbie give me your hand." As I reached up to hold her right hand, I continued to play around where her public hair ended in the crack of her thigh and outer lips. She slipped her hand in mine. I took it down to her pussy. I held her two fingers and wet them on the very entrance to her vagina. She let out some more air and moaned a little. I could see the entrance to her vagina actually contract a little as I pressed her fingers in to pick up as much fluid as I could. That was made easy by the considerable flow she was producing now. I moved her wet fingers along her inner lips from side to side. I was avoided her clitoris which by now was clearly peaking out from her distended, thickened lips. I had her moisten her hood, and we made circles around and around. By now Debbie hips were moving her in a rhythmic state, as though she was trying to capture her fingers inside herself. She kept moaning. "Oh Sissy, oh Sissy, oh please, oh please, oh God, oh God." I didn't think it was fair to prolong her orgasm any longer. I moved her fingers inside her vagina and moving at the same speed she was, took my own moist fingers to her clit and softly but urgently began to move the tips of my fingers very rapidly all over her. She started to climax immediately. She thrust her hips up, lifting her self completely off the mattress. She started to yell rather loudly. I placed my other hand at her mouth to muffle her sound a little. "Ahhhhhhhhhhhh, ahhhhhhhhhhhhhh." Again and again. Her own fingers had fallen from her pussy, but I could clearly see she was not finished, so I placed my fingers deeply inside her and in fact began to finger fuck her. I could clearly feel her vagina contract around my three fingers deep within her. I reached over and grabbed her other hand and brought it to her wet clit and held it there while she touched and did herself. She was having wave after wave of comes. She had quieted down somewhat, and was no longer yelling. She was just moaning and humming with each spasm. It finally began to slow down. I waited for a while to remove my fingers from inside her. Because each time I moved to take them out she would hold me there and have another little orgasm. She finally drew my fingers from her vagina. The smell of sex was in the air. The whole episode had made me extremely turned on and I could smell my own flow, mixing with Debbie's distinct odor. She was now still. I was also exhausted, and lay my head down on Debbie's thigh. I could strongly smell her. It was a wonderfully rich odor. I heard Debbie murmuring. "Sissy thank you, thank you. Oh God Sissy that was unbelievable." Over and over, a flood of thanks and compliments. "Hon, my darling, it was my pleasure. I can't tell you how much I enjoyed giving you a gift like this. Remember that you'll always have it." I had by now worked myself into quite a state of arousal. With the grass, and the whole scene that was taking place, I was by now as sexually high as I could ever remember. I needed to give myself a little something or would die.
Debbie had now curled up on her bed in a sort of fetal position. She was still awake, watching me through half-closed eyes, and a sweet satisfied smile. She asked me something in such a low voice that I had to lean over to her. "Sissy" She asked. "Can't I do something for you? You know what I mean." I was moved by her offer, and told her so. "It's ok my darling. You go to sleep. I'll do myself in my room. You don't have to help me this time. Maybe at another time. I promise I'll let you do it. I actually would love you too." She seemed satisfied, and drifted off to sleep. I pulled her blanket up, kissed her forehead and quietly left the room, as I switched her light off. When I got to the bathroom, I immediately went to a place on the rear wall. There was a loose piece of wainscoting. I could easily slip it away from the wall. It was piece about eighteen inches long. I had discovered this loose piece of wood a few years before. It was a perfect hiding place. When I removed the board, you could see that another piece of wood formed a six-inch shelf. When the board went back, you would never know anything was hidden there.
In the wall were my stash of grass, a little chunk of hash wrapped in foil, a little brass hash pipe, and a packet of Bamboo papers. Also hidden were two old books that I had found in a Dumpster, the year before. They where, "The Joy of Sex" and "The Joy of Lesbian Sex". I had read those books so many times; I had to keep them together with masking and Scotch tape. I had been absolutely thrilled when I found these books; it was as if my prayers had been answered. They answered just about every question that I had about sex, and plenty more that had never occurred to me. The books pencil illustrations were kind of disappointing in the beginning, but after a while, they became amazingly real to me. I remember thinking; Debbie will love these books.
I also thought that maybe it might be a good time to introduce Debbie to Arlene Strenich. I was certain they would really hit it off. I had learnt so much from her, I was certain Arlene would love another pupil and baby sitter.
I lay down in bed, and simply recollected what had just gone on with Debbie. I gave myself a few strokes, and I was there.