Sissy’s Game         January 25, 2012

Warning; This is a very naughty story and may not be desirable for uptight youth.

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Chapter I: Girls Going Wild

When you grow up with four younger sisters, there are going to be times when you tease and get teased. This is a story of one sister who turned my teasing around, but provided lots of memories for both of us. The story is based on experience, but is not all fact.

Sissy was the nick-name I gave to my second oldest sister. She came on as a tom-boy early on always wanting to do things the boys do, and loved to act as tough as any boy.

Sissy was several years younger than me, so for the early years, I considered her mostly as a pest. I often tried to ignore her, and even tried to discourage her from following and hanging out with me. It didn’t seem to do much good. She openly protested that she wanted to do stuff that boys do, and her sisters thought she was weird. I tried to explain that my friends were several years older than her and didn’t hang out with girls, especially little girls. Sissy’s feelings were hurt, and in no time at all, she was back, insisting that she still liked being my little tom-boy.

For the first ten years of my life, sex had nothing to do with this problem. Sissy and my other sisters had their own bedrooms, but we shared th same bathroom. Nudity was no big issue other than maybe some curioity. We didn’t know enough about sex to get serious about it. I think that was especially true with Sissy. To her, the only difference between a boy and a girl was that boys had a little thingy they peed out of. Sissy thought nothing of following me to the bathroom to watch me pee or to see me shower. The only reason she didn’t shower with me was because my parents didn’t allow that.

While the girls shared a large bedroom, I was given my own. There was some envy from the girls, but this was explained away by my parents as necessary because I was older, and because boys don’t sleep with their sisters. The girls accepted that this was necessary.

And since we shared the only upstairs bathroom, I got away withsleeping a little longer than te girls. When mom had breakfast ready, she would send Sissy to get me. Sissy was more tan happy to do that. She would run into my room and jump on the bed, bouncing around and teasing me. Mostly in self-defense, I would grab her by the feet, pulling her onto the bed, where I would get even by tickling her. The fact that Sissy usually wore only her white cotton panties, or that I slept in my briefs never bothered us. At times, we would wrestle and roll around touching each other wherever with no idea that this was naughty. It was just a game. Usually it ended when I hopped out of bed to go pee.

As we grew older, the other girls thought Sissy should not be running around downstairs in her panties since every one else was getting dressed for school before eating breakfast. So Sissy made a slight change. She would wake, shower, then still in her panties, come bouncing into my bed. She really didn’t see what the fuss was about.And I guess I didn’t either - at first. 

Sissy must have been about nine years old when I first realized I had a problem. By this time, I was twelve. And things to do with me and my body were changing. I was growing faster than I had ever grown before. I had also been hearing things at school about sex stuff. But mostly, I would wake up in the morning with a stii dick. I had also discovered that touching or rubbing my thingy caused it to feel good and to get stiff.

Keep in mind that the whole time I was discovering this stuff, Sissy was still jumping onto my bed every morning.

At some point, she jumped on the bed to discover a small tent rising where my thingy was. I seem to recall she giggled, and then grabbed hold of it. I’m sure I was startled and confused. I had no idea of what a piss hard-on was, but I also didn’t think having some one grab my dick (I had learned that a thingy was for little boys, not for big boys) could feel so good. I let Sissy hold it, rub it, and play with it, but I quickly explained to her that this was something that happened to big boys, and that she must promise not to tell others about it. She seemed to understand this was some sort of naughty secret between us, but still didn’t relate it to sex. It was a growing up thing. Girls got big boobs. Boys get stiffys. If anything, Sissy was envious that she wasn’t looking forward to big boobs. It’s hard to be like a boy when they have a stiffy, and you get big boobs instead.

For me, the challenge was a whole different thing. Being older, I was more aware of puberty and the new world of sex. When sissy and I wrestled around on te bed in the morning, I wondered what it would be like to get her to suck on my dick. I had heard of sex games kids play, and I knew that soon I would start growing hair and shooting cum. There was the usual fear of having sex with a sister. I had heard about incest. I had also played games with my buddies like jerking off. Despite my self, I taught Sissy how to taste, lick, and suck on my dick. She took it as things boys did that she could do too. Once I had convinced her to suck me until I got that fantastic feeling, there was no turning back. I knew that girls could get pregnant, so I didn’t go that far.

Although the wake-up game faded away when I had to get up earlier to go to middle school, Sissy and I remained close. We had no fear of seeing each other nude or of fooling around. Sissy was still a tom-boy at twelve, but I was now into sports activities at school, and was also checking out girls other than her.

Sissy started inviting her girl friends to spend the night, and often brought friends home fromschool with her. A few of them were closer than others. They seemed to sense that Sissy and I were very close.

One of her best friends was a girl thirteen named Paula. Paula was developing rapidly, and knew that Sissy and I knew way to much about each other. She was sure we were playing sex games. I don’t think either Sissy or I had told her anything, Paula had made it clear to Sissy she had a crush on me, and had started spending a lot of time at our place. She would wear short, light, tight clothes when we were home alone. Sissy seemed to like the game, and did nothing to stop or discourage her.

Early one evening when I came home from school, I headed for the shower to clean up. There was no one at home other than Sissy, Paula, and me. As I came out of the bathroom with nothing but a short towel around my waist, I ran smack dab into Paula coming upstairs to visit with Sissy. She smiled from ear to ear as she cut me off in the hall. Embarassed, I tried to avoid running into her, but not quickly enough. I felt a hand grab hold of my limp shaft, and jumprd back only to see the towel come undone and drop to the floor. As the shaft suddenly changed from limp to stiff, I managed to get my hands in front of my jewels,but not before Paula and Sissy had gotten a good look.

“WOW! This must be my lucky day!” Paula chirped as Sissy giggled, and I stood there frozen.

Neither of the girls made any attempt to move aside or to pick up the towel. And I knew if I bent over to recover the towel, I would have to remove my hands and expose myself again. I started backing toward the bathroom, thinking I could close the door or maybe grab another towel.

Paula picked up the towel and offered it to me (after getting a good look),

Feeling kind of flattered (and very horny), I Didn’t stop to think much about my exposure and had ovecome the redfaced blush. I reached out to take the offered towel once again giving her a pretty good look. I still had one hand there, but slowly took that one away to wrap the towel around my waist.

“I didn’t expect you two to be bounding up the stairs just as I made a run for my bedroom.” I tried to explain my way out of this, knowing it was a little late.

Paula took me by the hand and led me to my room. Sissy smiled and followed. Since I had a room by myself, she knew we wouldn’t be disturbed there. Not sure I wanted to go along with this with Sissy watching, I hesitated by letting her lead. And lead she did. She closed the door behind us. Dropping the towel again, she felt me up holding and rubbing my dick and my balls.

Sissy explained to Paula that I liked it when she sucked on it. Paula hesitated a little, but then sat down on the edge of my bed and leaned forward to taste it. After a few licks at the juice seeping out the end of it, she decided to go for it. She had heard about blow jobs, but had never done that. With lots of encouragement from me, and lots of advice from Sissy, she was doing just fine. It wasn’t long before I was thrusting it to her. When I felt the load building, I pulled back fast enough to blast my load onto the towel. I didn’t think she was ready for drinking my load.

We exchanged kisses. Paula was really good at that. I was sure she had plenty of practice. We also agreed to do this again. She surprised me when she said she had not had sex before. I couldn’t believe it. She was so forward, and was not the least bit shy. At any rate, she was staying the night, and we agreed to do it again, and maybe more. I couldn’t wait to get her clothes off. Paula was very sexy and mature for a thirteen year old. The thought of getting her kept my dick from going limp even after she had got me off. The three of us played around for about ten minutes more before we had to get back to other things. I think someone had come in, but didn’t know we were in my room playing. At any rate, we quickly broke it up.

It was the next day when we met again. We got home from school before the others. Sissy and Paula camr to my room. We closed and locked the door. This time Sissy and Paula stripped down. So did I. Once again, we played around. Sissy showed me how to check out and eat out their pussy. I couldn’t believe we were now sucking and checking each other out. I found out Sissy and Paula had been doing this to each other before, but this was the first time they had included a boy. Sissy and I admitted to Paula we had played games together. Paula knew we would keep this to ourselves.

Although I had not screwed my sister, I had no problem going all the way with Paula. She seemed as anxious to do it as I was. Once we became comfortable with each other, I climbed up on top of her with my dick at the entrance. She watched as I straddled her and placed my dick between her slit. She watched quietly as it slowly entered. I could feel the warmth and the excitement as my shaft was sliding into a warm wet hole. It was a feeling I had never experienced before. It was also something I couldn’t resist. A shrt way in, I felt a slight resistance. I hesitated, but Paula pushed upward, then moaned. It sounded like more of a grunt than a sound of pain. She pushed again, and I felt the shaft slide further in. Then she began to moan in pleasure as I moved my dick around inside her. Paula responded by hugging and kissing me. It was not until later I found out about the hymen. I had taken her cherry, but didn’t know that I had done it. Once in, I began a slow rhythm. This speeded up as I felt a sudden need to unload and claim her as mine. Sissy played with herself and watched us. I was working her pretty vigorously when my nuts let loose their load. Paula rocked back and forth on the bed as I felt my rigid shaft pumping what seemed like a huge load into her. She had already climaxed at least twice, and had made me feel really excited by clinging tightly as I came.

Both of us were sweaty and hot as we realized we had just finished our first real love making. I spent a lot of time playing with her budding breasts, and learning how to make love to a girl. But we also knew this one was special. Neither of us had gone this far before. We held on to each other for what seemed a long time. There was a lot of kissing and exploring before Sissy convinced us to part. Even then, I was still very erect and didn’t want to pull out. Neither of us wanted it to end.

Not much was said after it was over. The girls went to their room. All of us showered. The other younger ones came home. Other than a wink now and then, we were soon involved in the usual picking and fighting at the house.

The next morning when Sissy came to my room to wake me up, I could tell some thing was bothering her. She locked the door this time. She also removed all her clothes and seemed more intent on showing off her budding breasts and her slit which she now kept shaved. She wanted more attention from me. At first, I thought she felt I was getting more out of our fun than she was. To make up for that, I spent more time kissing and playing with her rapidly expanding mounds. She moaned as I ate out her slit, and brought her to a steaming climax. I could feel her cumming for me.

Then as I slid back up to face her, she made her move. I felt her take a hand and place the head of my dick at her entrance. I was trying to explain again why we should not do that, but I think I knew even before I could stop her I knew it wouldn’t work this time. Sissy was sliding on top of me so that my dick was pushing deeper inside her. When Iwas totally inside, she paused.

“I want it.” she protested.

And with that, she took charge. She turned me every which way but loose, and pumped until my dick started doing the thinking for me. I could feel the cum boiling to the surface. I rolled her over and pounded away. Within seconds, I was blasting away, For several minutes, I couldn’t stop. She wanted it. She was going to get it all. Only when I realized there was nothing left did I finally relax on top of her.

She explained that she couldn’t believe I was going to screw her best friend and not her. We discuseed the problems with what I was doing. It was agreed I would provide them with condoms to prevent any accidents. It was also agreed she would be included. I couldn’t believe I had now taken both their cherries.

Although I met with both girls often for the next couple of weeks, I did not screw Sissy in front of Paula. That was a no-no. Sissy and I agreed she could watch while I had sex with Paula, but she was not to know what we did on our own. I don’t think it was the incest thing. I would find out later the two of them had a girlie affair going on between them before I got involved with Paula. Maybe there was some envy involved.

At any rate, Paula would pull a stunt that would change everything. It would also change my sex interests.

One day, Paula showed up to play around, but this time she brought along her little brother, Bobby. She said she had to babysit him for the evening. Her mom had agreed she could stay the night with Sissy, but she would have to bring Bobby with her. Over his objections, Sissy and Paula had agreed to the deal. My parents had agreed Bobby could stay. For some reason, I didn’t even know Paula had a brother.

When Paula introduced Bobby, I was both surprised and disappointed. How was I supposed to make out with the girls with Bobby there? What were they thinking?

On the other hand, I was equally surprised with Bobby’s looks and personality. He was a gorgeous blond twelve year old with blue eyes and a beautiful body to match. I had fooled around with a couple of boys before, but this one was a little young yet a boy doll. He had Paula’s good looks, and even her outgoing seductiveness. I think I knew I wanted him from the time we met. I just couldn’t believe my feelings toward him. The other boys I had fooled around with were just mutual jerk off sessions and boy games. Not this one. His smile alone would cause me to get aroused.

Both Sissy and Paula teased that we couldn’t play around that night. Not with Bobby there. He knew nothing about their games, and if he found out, he could cause Paula trouble at home. Especially if her parents found out she was having sex with a teen brother of Sissy’s. The girls seemed to be having fun with the teasing. I should have been more upset than I was. I tried to act really upset, but secretly I was wondering what it would be like to fool around with Bobby.

My big opportunity came as the hour grew late, and sleeping arrangements came up. Sissy nervously and shyly asked if I would let Bobby sleep in bed with me that night. Otherwise, he would have to use the sofa in the living room. That would mean he would be in the way when the parents got up early and when the younger kids got up. If he could sleep with me, he could sleep in later.

Of course, I insisted that both girls owed me if I agreed to their request, but actually I considered this an unbelievable opportunity to get to know Bobby. Still, I tried to show no hidden desires as they agreed to talk later about paying back the favor. Bobby smiled shyly, but I was sure he knew my favor had something to do with sex. His sister had that sexy look in her eyes.

I led Bobby to my room, and explained that there was plenty of room in my bed for both of us. We took time to shower. He went first, returning to the room wearing his briefs covered by a towel around his waist. As he entered, he dropped the towel and climbed on the bed, laying on top of the covers and chatting as I got undressed to shower. Both of us took the chance to look over the other’s body just out of curiosity. He appeared to be really sexy, but showed no arousal. On the other hand, I quickly grabbed a towel to cover the obvious tent in my briefs. I knew he could see it, but he showed no shock. I took off to shower. I made it quick hoping to get a chance to do more than look when I got back.

I was semi-erect when I got back so it didn’t look all that obvious that I was horny. Bobby was still laying on top of the covers as I joined him. Turning off the overhead light, it was dimly light when we chatted about school and sports for awhile. I was several years older than Bobby so didn’t go the same school or hang with the same crowd, but he knew I was on the school baseball team and thought that was cool.

Things got more intense when Bobby shyly asked if I liked his sister. I answered honestly that she was hot, and was well developed for her age. I could tell by the surprising tent in his briefs that this was leading to sex curiosity. I looked, and just smiled at him. He blushed, then pointed to my own rising problem. Laughing, I reached over and stroked Bobby’s chest and stomach, loving the feel of his smooth tight body. He was surprised at first, but liked the feel as one hand gently worked his inner thigh while the other made cirles on his stomach and chest. He was still cooing softly as one hand touched his ball sac while the other one was moving to play with his three inch stiffy. He looked at me, then at my hands and his crotch. He made no move to move away or stop me.

Bobby was every bit as sexy as his sister. When I tugged at his white briefs, he lifted his hips to make it easier, and watched as the briefs slid down and off his legs. He smiled as I moved down far enough to to show him how fun a blow job could feel. I easily took his stiffy to the hilt and then licked and included his small balls as well. I knew I had him. Bobby cooed and allowed me to take him to new heights playing sex games he had heard of but never expected to play - and certainly not with an older boy.

When I heard him whisper that he had to pee, I knew he was reaching his first dry cum. Instead of backing off, I held him tight and sped up my assault on his stiffy. He was soon humping instinctively and making strange noises as his toes curled, his legs drew tight, and his back arched trying to push his shaft entirely inside my mouth.

One final “Oh my gosh!!!”, and his shaft was twitching wildly trying to unload the sperm that wasn’t there yet.

Exhausted, but very happy, Bobby relaxed and lay limply on the bed.

As I let him go, I raised up and hugged him to let him know everything was fine. I smiled and gave him a peck on the cheek. He was smiling from ear to ear, looking more than a little confused. When he returned from dreamland, we talked about why boys loved having sex. And orgasms. And blow jobs, jerking off, and why stiffys became dicks, and sex stuff.

I also slipped out of my undies so Bobby could play with my six inch hard dick and explore, feel, and stroke it. I left it up to him to decide how far he wanted to go with it for now. No need to rush it. We had all night to play around.

The first thing Bobby wanted to know about was jerking off. He had heard that older guys could shoot stuff that made babies. He wanted to see that. He was also impressed with the size of my dick and the balls. After he had rested up from his own new experience, he was more than willing to help me have fun. He wasn’t ready to suck on that monster yet, but he would help me stroke it until it shot off.

I took his small hand, wrapped it around my shaft, placed my hand over his, and showed him how to get the most out of jerking off. He was fascinated with the feel of the shaft, and watched closely as I held his hand in place. We started off slowly, then sped up as he got the hang of it. I loved having him help. It wasn’t long before my shaft responded to the attention, and as he felt the shaft expand, the two of us could feel the sperm spurt through and shoot into the air landing on my chest and stomach in long white strings. His eyes went wide as he saw a guy shoot off for the first time ever. When it was done, I let him touch the goo, and feel it. Then I cleaned it off. And he felt the shaft after it had softened.

We agreed this was a boy thing not to be discussed with others, and slept nude the rest of the night. I knew I had his interest. We would do more later.

Bobby left to go home that morning, but would show up at my ball practice and track meets. He loved being around an older guy. I had no problem with that. He never mentioned our sex play, or caused any one to notice our close friendship.

I still saw Paula and Sissy as usual. We would have sex after school several times a week. Neither of the girls was aware that I had developed a special interest in Bobby.

Next chapter: Two Loves Have I.

Will the girls catch on? Will Bobby want to go further? What could go wrong?