Exploring the Night

An experience shared by Michael:

~ ~ ~

I have always been a sexual person. Some of my earliest memories involve sexual exploration. My younger sister (18 months younger) and I took baths together until my mother decided our behavior was becoming inappropriate. It was innocent exploration, however, I knew that I liked the feeling of my “thing” being touched when it was hard. I loved to be naked and would play games that allowed me to get that way. My mother’s vigilance soon put an end to our games. I was 7 and my sister was 6 (the math works, my birthday is in November, hers is in May) when she walked in on my older cousin and me. We were in the changing room out by the pool. He and I were naked. As I recall, on a dare, she sucked each one of us for a minute or so. I remember having a fluttery sensation in my stomach as she did that.

After that, it seemed like the sexual play increased. I would try to see my sister changing, or when she had one of her friends over I would try to catch a glimpse of them in the shower. Typical kid stuff. One of my favorite things to do was when we were swimming in the pool. I would untie my bathing suit so that when I dove in, it would slip off! My sister or one of her friends would invariably grab it, and a game of keep away would ensue. I’m sure you see the beauty of this. I would be hard and naked, and I would grab my sister, or whatever friend she had over, and try to retrieve my bathing suit. They would always end the game by throwing it out of the pool, forcing me to climb out naked and recover it. They always watched me pick it up and put it back on. I would also hide under her bed and watch her change clothes. Sometimes to heighten the thrill I would sneak into her room naked and hide. I would lie under her bed and watch as her and a friend would change as I humped the carpet. God what a feeling that was: terrified they would catch me, and all the while hoping they would.

This next part took place after the story of my male cousin and me. Also, I want to say that this happened many years ago. During that time, parents would leave their children at home without hiring a baby sitter. I have also asked my sister and her friend if it would be okay with them if I submitted this story, and they both agreed to let me.

My little sister’s best friend had been staying at our house every weekend for quite a while. We had horses and her friend boarded her horse with us, which is why she was always at our house. Both my sister and her friend had seen me naked with a hard-on several times, and by the age of 14 my hormones were in overdrive. I had a crush on her friend and I would find any excuse to be around them. I had also taken to locating her panties in the dirty clothes hamper and giving them a sniff. They were just your standard every day girl’s underwear, and honestly, because my sister and she were so similar in shape and size I knew that half the time I probably had my sister’s panties. It really didn’t matter to me , the faint acrid odor and having my face in the same place that so recently held the object of my adolescent desire was always enough to push me over the edge.

One night, or I suppose it was very early morning, while on my way to the bathroom, I passed my sister’s bedroom door. It was wide open and the light from my room cast a square of light onto my sister’s bed. She was asleep, of course, and her night gown was gathered up around her waist. She was on her side, her back was to me, and one side of her panties were pulled back, exposing her butt cheek. I just stood there for a moment, stunned!

I quickly went back to my room and shut the door. I listened, my heart pounding in my chest. I quietly went back to my sister’s door. I got to my knees and listened to her breathing. It was slow and steady, she was still fast asleep. As my eyes adjusted to the darkness, I could once again see her sleeping form, and more importantly I could see her exposed butt cheek. I crept closer to her bed and rose up from my hands into a crouching position. Without touching the bed, I leaned in a little closer. It goes without saying I was so hard it hurt, and I was trembling uncontrollably.

I carefully reached out and as lightly as I could I touched my sister’s butt. She moved, and I bolted for the bathroom. I almost slammed the door, but caught myself just in time. I waited and tried to listen but my breathing and heart beat where both so fast I couldn’t hear a thing. When I finally calmed down enough, I looked back around the corner. My sister was still sleeping, however, she had pulled the blankets back over herself. I went back to my room and masturbated as only a fourteen-year-old boy could.

This was just the beginning of many sleepless nights. The next day I waited, and nothing happened. My sister acted the same towards me. That next night I returned, but she slept under the covers. After several nights of this, my desperation grew. Finally one night I lifted the covers up from the foot of the bed and using a flashlight looked again. She was lying on her back with her night gown bunched around her waist once more. Her panties were pulled up so tight that I could plainly see the outline of her. I nearly came right then. I lowered the blankets and went back to my room, I think I fell sleep around dawn. I must have cum four times that night.

The weekend finally rolled around and her friend once more spent the night. By now my body had become accustomed to waking up and going on my nocturnal visits. As I lay there in bed stroking myself, I wondered if I should even get out of bed, but my hormones were in charge and flashlight in hand I worked my way into the hallway. My sister’s door was open as usual, and as I crept closer I could see two forms on the bed. With all the stealth I could muster, I looked into the room.

My sister was sleeping on her stomach, with her night gown bunched around her middle, her friend was on her side with her night gown just covering her round little butt. I ever so gently pulled my sister’s night gown away and slightly up and got my first glimpse of her panty-clad bottom. My sister moved, and so did I. Flying back to my room.

I was up and out doing chores before the girls where even awake and the day was a typical Saturday. That night, however, when I went on my nightly haunt, it was unbelievable. When I snuck into my sisters room, her friend was asleep face down, wearing a little shirt and panties, with both cheeks half exposed, and my sister was dressed similarly, lying on her back. Her panties where pulled to the side exposing one lip. I started to tremble so badly I got out of the room before I woke either one of them.

My nighttime forays continued for most of the following week, when one night I was surprised once more. When I went to my sister’s room, she was asleep on her back, on top of the covers with her night gown bunched around her waist, and she wasn’t wearing any panties! I just sat there at the foot of her bed gazing in wonder. I realized I had been rubbing myself while staring at her and then to my shock, I came right there in my underwear! I quickly crawled out of her room and spent another sleepless night.

The next night when I crept into her room she was lying asleep on top of her covers wearing a shirt and no panties again. I moved closer to the side of the bed, to get a better look. I’m not sure how long I had been staring when suddenly I realized my sister’s eyes where wide open! I freaked out, I flew out of the room. My sister was following me as I bolted for my room. She caught a hold of my arm and kept whispering, “It’s okay.”

She followed me into my room. I was babbling an apology and begging her not to tell our parents, and promising anything if she wouldn’t tell. It took me a minute or so to realize she kept telling me it was okay. I looked at her, she smiled and said it’s okay one more time. She started to laugh at me. It dawned on me how stupid I must have looked, and started to laugh as well. She was giggling as she hugged my neck, telling me she knew I was sneaking into her room and looking at her for a while. She had heard me get up to go to the bathroom one night and wondered why she didn’t hear me in the bathroom, that’s when she felt the covers move and knew I was looking under them at her. She said at first she was mad, but it gave her a tingly feeling in her tummy, that’s why she stopped wearing panties at night. She would wait until I would go back to my room and then come and listen at my door. She told me she knew I was “jacking off” when I went to my room.

My sister and I talked for a long time. She told me about watching her friend’s brother shoot when he jacked off, and how she and her friend had discovered how to make themselves cum. I told her about the things I had done with my cousin (she told me she had seen us once when I was sucking him), and how I had tried to see her and her friend sleeping. She explained that her and her friend knew I would try to spy on them and they had dressed the way they did on purpose, then listened to me play with myself afterwards.

My sister became my friend that night. We had never been very close. That night we shared our hearts with each other. As we talked, we both became more relaxed. She sat on my bed Indian style, I leaned back against my head board. It wasn’t long before my erection was clearly visible. My sister said it wasn’t fair that she had no panties on and I still had my shorts on. I told her if I took off my shorts I would be naked, and she had on a shirt. She said fine and took off her shirt.

I slipped off my shorts, and we sat naked on my bed. This was the first time I had more than just a quick looks at her budding breasts. They were sort of chubby with large puffy nipples. By this time I was so hard it was painful and I was all but dripping pre-cum. She asked me if I was cumming, and I explained to her about pre-cum. She asked me if my cousin did the same thing and I told her yes. then she wanted to know what it tasted like, I’m sure I had the biggest, stupidest grin on my face when I leaned back and said, “Have a taste.” She had a big stupid grin on her face when she said to me, “I will, if you will.”

How could I say no to that? I leaned back and she crawled up between my knees, and with one quick move took the head of my cock into her mouth. She began sucking on me like a straw, it took only a moment or two and I had to pull her off me, with a little popping sound the head slipped from her lips and I erupted, shooting up over my chest and stomach. She just stared in wonder at it. As the last spasms of my climax were fading, she jumped to her feet, grabbed her shirt and ran back to her room. I was going to follow her but I heard what she must have heard as well. The unmistakable sounds of my father getting ready for work. I cleaned myself up and fell asleep for a few hours.

I didn’t see much of my sister that day or the next. I didn’t return to her room that night, the lack of sleepless nights was beginning to take its toll on me and I needed some time to think about what had happened. The next time we were alone together was a Thursday night. My parents had gone out and wouldn’t be back till around midnight. I was in the front room watching “Kung Fu” when my sister came in and asked if I was mad at her. I just looked at her and she said. “Well, you haven’t looked at me for the last couple of nights,” so she thought I was upset with her. I told her “No,” I was just thinking, that’s all.

I was kind of scared at what we had done, and that we could get in a lot of trouble if anyone (our parents) found out. She kept trying to assure me that she would never tell anyone, but I had my doubts. I told her I needed to think about it some more. The weekend came around and of course her friend stayed the night. I had not repeated my nighttime explorations since that night. I did get up and go to the bathroom one time while her friend was there, and as I passed her room I noticed that both girls were lying on top of the covers with their night gowns bunched up around their waists and no panties on. I hurried back to my room with the intention of rubbing one out, but the thought that they might be listening at the door kept me distracted. I kept sneaking to the door and pulling it open, in an effort to catch them at it.

It wasn’t till later that next week that something more happened. I was asleep in my room, when someone opening my door woke me. I recognized my sister right away and what’s more she was naked! She came right to my bed and slid under the covers. At first I thought she was cold; she was shivering so badly, then I realized she was trembling. I put my arms around her and hugged her and asked what was wrong? She said, “I don’t know,” then snuggled up against me.

I had been sleeping naked ever since my cousin and I had played together and she could feel me hard against her skin. She giggled and asked, “Is that for me?” and I said in my best John Wayne impersonation, “Why yes, little sister.” That made her laugh and she tried to slap me, and we started wrestling around under the covers. In all the commotion, my cock was repeatedly stabbing her in the thigh and leg leaving trails of pre-cum, when all of a sudden we both froze.

She had wiggled around and now my cockhead was right between her legs just against the opening. I instantly pulled back, and started to apologize. I was upset and she was trying to calm me back down. I told her I hadn’t meant to do that, and she said she knew, and then after a beat or two said, it felt really good though. I told her we couldn’t, I could get her pregnant, and that our parents would kill us if that happened. She kept telling me it was okay. Then she asked me if she could just try something. I was a little unsure, my sister could do crazy things at times, but I gave her a very unsure nod of my head.

She pushed my shoulders back on the bed and started to climb on top of me! I grabbed her and stopped her, I told her we can’t. She kept saying, “I know, this will be okay though.” I grabbed the head of my cock to keep her from impaling herself on me, then she straddled my hips, and lowered herself down on me. She wiggled just a little and came to rest with my rock hard cock snuggled between her outer lips.

I was overwhelmed by that dizzy-swoopy feeling, like the whole room was floating. The combination of moist heat and the knowledge of what she was doing had disconnected my brain. Slowly she began to rub up and down on me. Suddenly she began to convulse, her finger nails digging into my chest, her hips bucking and grinding against me, she was making stifled grunting noises in her throat. My mind finally cleared enough to realize she was having an orgasm! T

he full weight of what was happening finally hit me. The first time I was with a female having an orgasm, it was my sister and she was doing it while sliding up and down on my cock. My mind went blank, I convulsed and I came so hard it hurt, spraying cum up over my chest, on to my face. I heaved my hips up and flipped my sister off of me, my penis was so sensitive that I couldn’t stand to have it touched. There we lay, side by side, naked, panting as if we had just ran a mile, and my sister began to giggle.

I must have looked at her as if she had lost her mind. Through her giggles she said, pointing at my face and chest, “Now I know what they mean when they say messy sex.” I know it’s not that funny, but I broke out laughing with her. I went to hug her and she pushed me away with an “Eww, gross” comment and grabbed the corner of the blanket and started to wipe me off. She snuggled up in my arms and kissed me on the cheek, and I held her until I started to doze off, that’s when she got up and went back to her room.

When I woke up the next morning, my thoughts were in a blur. I’ve always been a worrier, and my mind was racing. I had no idea how my sister was going to respond to me. As it turned out, I had nothing to worry about. It was a completely average morning, with one exception. Before she left the house, she came up to me and gave me a very un-sisterly like hug and a kiss on the cheek, smiled at me and went out the door.

Thus began and almost nightly routine of my sister coming into my room at night naked and riding me to a climax. As strange is this may seem, we only tried kissing once, and we both found it so awkward that we never tried it again. We would get together if our parents were out for an evening, and nearly every night. We did not play when her friend spent the night, and as far as I know, our secret was ours alone.

While it never occurred to me that my sister would blab everything to her friend (I didn’t know girls that well back then) she apparently had. One night after we were done “playing,” I was holding my sister and she explained to me that her best friend had always had a crush on me and she wanted to play with us. I just about freaked out! “You told her what we’ve been doing?” I hissed. “Are you crazy? She’s going to tell everyone!” She assured me that she wouldn’t and I eventually calmed down.

The following weekend, our parents would be out until around two in the morning. We kids would be alone for most of the night. As Friday night got closer, I was becoming more and more nervous. I told my sister at least three times we were not going to do anything. My sister, in the meantime, had become very adept at manipulating me. She could get just about anything she wanted out of me.

Friday finally arrived and her friend came over right after school as usual, and everything seemed quite normal. I had almost forgotten my fears, when my parents’ car had pulled out of the driveway, and I realized I was alone with two girls in the house, two girls that had shared our secret. I had that same swoopy feeling in the pit of my stomach once more. Then my sister was calling me from her room.

The door was open and they were both standing in the middle of the room completely naked! They both started to laugh, I guess the expression on my face was pretty funny. I must have looked like I was going to turn and run because they both grabbed my arms and pulled me into the room. My sister told me to take off my clothes, but my eyes where focused on her friend. She smiled at me and nodded her head, so I took off my clothes. My sister took charge. It was like I was a scientific experiment, for the next hour the two of them explored my body.

My sister and her friend talked to each other. As you might imagine I was incredibly hard the entire time, and literally dripping pre-cum. My sister explained to her friend what it was and even licked the head a couple of times, sending bolts electricity through my nervous system! I noticed both girls touching themselves from time to time. My sister was a little bolder and would just rub herself, but her friend would sort of flick at herself and rubbed her thighs together quite a bit. Finally my sister explained to her friend how to straddle me. Taking a hold of the head of my cock she guided her friend down on top of me, so that she had me firmly wedged between her lips.

With my sister explaining to her what to do she started to rock back and forth. That was all I could take, I started cumming at once, spraying cum up on my stomach. Her friend leaped off me and with what I can only describe as disgust, stared at me. My sister was giggling and explaining, “That’s what’s supposed to happen.” My sister, still giggling, ran and got a towel so I could wipe up, and then with a devilish grin said to her friend, “Watch and I’ll show you.”

With that she climbed on and began to ride me. (Even though I had just climaxed, I had not gone soft. isn’t youth wonderful?) Then she did something we had never done before, she turned around so she was facing my feet. Suddenly I was watching her cute little butt flex and jiggle as she worked on me. I couldn’t hold back, I came once more. I think that this was the moment when I became a confirmed ass man.

I had pushed her off me, I was just too sensitive keep going. Her friend had been sitting at the foot of the bed watching all of this, and now I noticed an odd look on her face, and her hand held tightly between her thighs. My sister got into what was now a familiar position, laying her head on my chest with my arm around her as we cuddled.

My sister explained to her friend that I needed a minute or two to recover, but it wouldn’t take too long. Her friend stayed at the foot of the bed. My sister’s prediction soon came true, as I once more started to swell. After a brief conversation with her friend in which they decided that my sister would go again. This was the first time we had done it this many times, and the first time I was not right on the edge of shooting. I was watching my sister, how her small breast bounced, the way her hair seemed to float around her face, I noticed the beads of perspiration as they trickled down her neck. In that moment I realized how beautiful she was. She had given herself over to what she was feeling. Then it happened!

I honestly cannot tell you how it happened, but it did. I was inside her!

I had penetrated her. I could feel her completely surrounding me. She was grinding down onto me as if she was trying to push me all the way through her. Her chin on her chest, her nails digging into my ribs, and she was cumming, hard. I could feel her body grabbing hold of me. I froze, my mind was a blur. I have no idea how long, perhaps fifteen seconds and then I freaked! I pushed her up off me and began to yell at her, “What the fuck are you doing? You’re going to get pregnant now!”

Even today as I write this, the terror of that moment returns. It took a couple of hours for me to calm down, if you could call it that. We never did anything else after that night. I lived in terror for the next couple of months, but thankfully she did not get pregnant. During that time I also learned how extraordinarily risky it was just to have her rubbing on me. I’m sorry to say that an emotional gulf opened up between us. I was scared and she was hurt. Life went on and in time we got back on friendly terms, but that closeness was gone.

Here we are over forty years later and several lifetimes from that night, and I have to thank Rachael, the host of this blog. You see in writing this story, I opened up a dark moment in my sister’s and my life. She never really understood my reaction, just how scared I was, and I never realized how hurt she was. She felt I had rejected her and that I hated her for it. Even her friend carried some scars from it, she was terribly afraid of my reaction. We have all talked at great length now and the healing has begun. My sister and I have grown closer in the last few days, and have even had a few good laughs about what happened.

I have had a very uninhibited sex life, experimenting and trying just about everything. My wife (who by the way was the editor of this story) and I have a wonderful open relationship, and sex is a healthy part of our day. The most important part of any relationship is communication. Talk to each other, and listen!

I would like to thank my sister and her friend for allowing me to tell our story, my wife and her mistress for their editing, and most of all Rachael for hosting this blog and making this all possible.

>~ ~ ~

Leave a Reply