EXPLORING WITH SISTER
Oct 7
This is a short memoir about an incident that occurred in my life about 10 years ago.

By the time I was 17, my sex life could be pretty much summed up by one word: frustration. I had been masturbating for a number of years, but when it came to the opposite sex, my experience was agonizingly limited. On two separate occasions, I engaged in some heavy petting with a girlfriend. I had even managed to slip my fingers into her wet vagina. But nothing was ever consummated that time or any other in my few sexual activities with girls.

I’d like to blame my problem on my straitlaced, Catholic family, but that would be a cheap way out. I had a good father, though constantly busy with his work. My mother was also good to me, despite her deep-seated conservatism in politics, religion and social outlook. I had a 16 year-old sister, Andrea, who seemed to be following in my mother’s footsteps. Outwardly, she was still suffering from teenage growing pains. She struggled with her weight and because of an eye condition, couldn’t wear contacts, so was forced to wear glasses with rather thick lenses. As a result, she didn’t try to draw attention to herself, dressing conservatively and wearing her light brown hair straight back in a simple ponytail.


One Friday evening, my sister was gone, helping out at a church function, while I had made arrangements to spend the night at a friend’s house. But when I got there, a mild family crisis had arisen, making it impossible for me to stay. I walked slowly home, disgusted with how the evening and probably the entire weekend was going to turn out. I must have opened the door quietly because my parents didn’t seem to hear me come in. It was then I heard a moaning noise come from upstairs. Somewhat alarmed, I cautiously walked up the stairs and then peeked down the hall towards my parents room where the noise was coming from.

I was stunned to see my parents on their bed, making love. In the dim light cast by the street light, I could make out my mother, completely naked, straddling my father, who was mostly hidden in the darkness. I still remember how shocked I was to see my conservative mother making love so fervently. With unbridled passion she rode my father’s penis, calling out, “oh my god...don’t stop...it feels so good!” over and over. I could see her large breasts sway and bounce as her excitement built.

Shocked as I was, I couldn’t take my eyes off of what was happening in their room. Worse, I was completely aroused by mother’s sexuality. Finally, I heard my father moan and raise his hips off the bed. I realized he must have just climaxed and so I beat a hasty retreat, heading back outdoors, so they wouldn’t know I was home. I went to our backyard and behind the garage where I masturbated furiously to relieve the tension and excitement of what I had just witnessed. I then wandered around the neighborhood for a good hour before returning This time, the lights in the house were on and my father and mother were downstairs watching TV and having a drink.

For the next week, I found it hard to get out of my mind the reality of my parent’s sexuality. Despite knowing they probably had sex all the time, the fact that I saw them performing the act seemed to change everything. It didn’t take long for me to realize that my quiet sister was probably sexually active too. I suddenly found that new thought hard to dismiss and, increasingly, wondered if there was some way to find out.

My hormones must have been raging that year. Without a girlfriend, I found myself constantly wondering about Andrea. Did she masturbate? Had she ever had sex? I realized I knew little about her, what she disliked or liked. Nor did I really know much about her physically. Because of her plumpness, she kept everything under wraps.

One evening, when my parents were out, I paid my sister a visit in her room. We talked innocently at first, but then I told her I had a secret to tell. Her ears perked up as I described what I saw that Friday night when I inadvertently came home early. Andrea was flabbergasted by my story. Sensing her interest, I described in detail what I saw: how Mom was on top, how she moaned and what she cried out while making love.

Andrea couldn’t believe I watched our parents make love. She said she would have been out of there in a flash. I told her how that was my reaction as well, but something held me back. Andrea then called me a voyeur. I said so what, and added that under the right circumstances, I bet she would watch a couple make love, if she knew they couldn’t see her.

She replied she wouldn’t do such a thing. I then saw my opening and dove in. Would you watch me, I asked, if you happened to see me masturbating in my room. Andrea began to turn red and denied she would. I then told her I masturbated all the time. Andrea said nothing. Without pausing, I then asked if she would like to watch me now. My sister’s reaction was swift. She called me disgusting and told me to leave her room. I knew I blew it, but went on defiantly, adding a lie that I masturbated with my last girlfriend. Andrea replied it’s not the same as doing it in front of your sister. I told her there was no difference, it was just curiosity. But, I got up and left her room, feeling completely embarrassed at what I had said.

I sat in my room, feeling like an absolute jerk. I figured Andrea took me for some kind of pervert and would keep her distance from me. She might even say something to Mom. For the next 20 minutes I felt like dying and crawling into a hole. Then, there was a knock on the door and Andrea stuck her head in. She asked if she could come in. When she did, she apologized for snapping at me. I began to tell her it was my fault and that I should be apologizing, when I noticed she she seemed to be blushing.

Andrea then asked if it was true about my masturbating in front of my girlfriend. I nodded, but added it only happened once, trying to downplay my little lie. Then she said, “show me how you did it.” Within seconds, my heart rate jumped as I realized just what she meant. I said okay and pulled my pants off and then my underpants. My penis was stiffening rapidly by the time I disrobed. I gulped and then quietly asked if she’d like to touch it first. Hesitantly, she did. First with her fingers and then she grasped it with her hand. She remarked at how big and stiff it was. I remember thinking, my sister has never seen an erect penis before!

I began to slowly stroke my member as my sister watched. As I felt the pressure increase, my hand began to move more rapidly. I kept glancing at Andrea, who’s eyes were glued to my penis. I found myself beginning to fantasize what she looked like naked. I stared at her breasts and wondered what it would be like to feel them. The thoughts came rapidly and within seconds I felt that wonderful throbbing sensation begin. As I ejaculated, I let out a groan as spurts of semen shot out and landed on my stomach and chest.

Andrea was silent for a moment, then murmured, “Wow!”. She looked quite flushed. I suddenly became quite candid and told her I enjoyed having her watch me and hoped I could do the same some time. She didn’t reply, but I had a hunch I could coax something out of her. The following weekend, I rented a porn video and when my father and mother had gone to sleep, I dropped by Andrea’s room and asked if she cared to watch the movie with me.

She groaned when I told her what it was, but about 10 minutes after I started the video, my sister sat down on the couch and began watching. I was wearing shorts and a t-shirt, standard bedtime clothes for me. Andrea had on a long night shirt. As the picture became more graphic and my arousal increased, I began to rub my penis through my shorts. Then Andrea spoke, saying she didn’t mind if I wanted to masturbate. I said okay and then added that she should join me. I peeled off my pants and began stroking my penis. I turned so that I was partially facing Andrea.

My sister soon began to rub herself. Within a minute or two, our eyes were on each other, not the film as we sat at opposite ends of the couch, caressing, rubbing and stroking ourselves. The sight of my younger sister touching herself in front of me proved incredibly exciting. I tried to hold back, but it was impossible. I let out a soft groan and told Andrea I was about to climax. Soon I had drops of semen all over my t-shirt.

Now I sat back and watched Andrea masturbate. The only light came from the TV, but it was enough to see her fingers rubbing her moist clit and vaginal lips. Clearly, she was no novice at masturbation. She took her time, building the excitement up. She leaned her head back, closed her eyes and began to breath heavily as the moment of orgasm came closer. All of a sudden she half-grunted, half-moaned as her hips convulsed and her body shuddered.

The sight of Andrea having an orgasm was enough to arouse me once again. With the TV still flickering in the background, I peeled off my T-shirt. I told my sister I wanted to masturbate again, but this time I’d like to look at her breasts. Andrea smiled, still dazed from her orgasm, but she complied, lifting up her shirt and giving me, for the first time, a full view of her body.


Andrea was plump, but at sixteen, her skin was soft and seemed to glow in the light cast by the TV. I found her round shape quite sensuous. Her breasts were larger than I expected and they had that firmness and roundness that can only be created by nature, not silicone. Her nipples jutted out and I found it hard not to touch or suck them.

I began stroking myself again. Soon, however, Andrea asked me to move closer. As I did, she reached over and began to stroke my penis for me. My heart began to beat wildly at what was happening. The sensation of my sister’s smooth hands on my penis was incredible. I remember smiling at my sister and she smiling back as she stroked my penis and caressed my balls. Within a couple of minutes, I felt the pressure begin to build again, and I warned Andrea what was about to happen. She only stroked faster and pointed my penis at her breasts. In another instant, I began gushing streams of semen on to her, trying not to groan too loud as I did.

I put my hands on to my sister’s breasts and began rubbing the semen over her warm skin, touching the nipples and massaging the undersides of her breasts. Andrea sighed softly, then rested on the cushions as my hands explored her soft body. It was an intoxicating moment for the both of us. One I will never forget.