Growing up I always admired my older sister, Debra. When I was younger I admired the way she handled my parents, which made things a lot easier on me. I always admired how she treated me; I was never the annoying little brother to her. We have always been very close. I think it was a result of all the moving we did growing up. Between the ages of 5 and 15 I lived in seven different towns. Any time you move as a child it always takes time to make new friends, but wherever we went we always had each other.
Debra is 10 months older than me and is currently a very attractive 31 year-old woman. I think she looks better today than she did ten years ago and I thought she looked damn good back then. She's 5'8" tall with shoulder length red hair (not natural but it fits her perfectly), she has a very well proportioned body with curves in just the right places. Her breasts are nice and firm and she has a beautiful ass that I always admired. In fact it was that ass that made me cross the line.
When I was 17 I started to look at Debra less as a sister and more as an incredibly attractive teenage girl. As you know, 17 year-old boys can be rather horny. I use to take any opportunity I could get to spy on Debra. I would try to sneak looks at her in the shower, getting dress, basically anywhere there might be a chance I'd see some flesh. Not too long after I turned 17 I got the chance to see her in all her glory, purely by accident. She came out of the shower one day with just a towel wrapped around her and as she was leaving the bathroom the towel caught on the door and was pulled off. She recovered quickly but it was long enough for me to see her firm breast and neatly trimmed bush.
That image was enough to fuel my fantasies for a month, giving me some of my most intense orgasms while masturbating. The quick peek was enough to fuel my desires and I started to take more and more risks to see her nude again. I was often rewarded with quick looks at a breast or her pussy but it wasn't enough to satisfy my urges. I was finally rewarded with a show that has stayed with me to this very day as one of the most sexually exciting moments of my life.
I had just turned 18 at the time and I finally cooked up a plan that might let me see what I wanted to see. Debra had been dating a guy named Tom for several months and I was certain they were having sex (I came across some condoms in her room while stealing a pair of her underwear). I decided to set things up so I could watch them. My parents were going out to a party and I knew they wouldn't be home until very late. I got the okay from them to spend the night at a friend's house. Of course I had no intention of doing that. Shortly after my parents left for their party I told Debra I was going out. She was eager to get rid of me because she had invited her boyfriend over. I left through the front door and circled back around the house and snuck in through the basement.
I hid downstairs for an hour until I heard Tom show up. I knew they would head to the family room first so I snuck upstairs and hid in Debra's closet. I figured it wouldn't be long before they came to her bedroom to do it. I waited for an hour but I grew impatient and decided to see what was going on. I snuck back down to the main floor of the house and moved quietly to the family room. When I looked around the corner I was treated to an incredibly exciting scene.
It took me a second to take everything in. Tom was standing in the middle of the room with no clothes on; his cock was rock hard and quite big. Debra was standing just in front of him performing a sexy striptease. My own cock quickly hardened as she started to remove her clothes. She started with her shirt and slowly, painfully unbuttoned it from the bottom up. After the buttons were undone, she slowly uncovered first one breast and then the other before covering them again. She turned around and then dropped her shirt to the floor. From my side view I could still see her hard nipples standing out from her firm breasts. My throbbing cock was starting to hurt in my jeans so I undid my pants to set it free.
Debra then slowly turned around to face Tom. He reached for her breasts but she stopped him with a shake of her finger. She then proceeded to flick and pull her own nipples. It was at this time that I started to rub my own cock. I was wishing that I were Tom. Debra left her nipples alone and slowly started to unbutton her skirt. She carefully held it up until all the buttons were undone and then she let it drop. She wasn't wearing any underwear and, unlike the last time I caught a glimpse of her pussy, she was now completely bare. I almost gasped out loud but stopped before I gave myself away. She slowly traced her finger around her bare pussy before she shoved it into her already wet cunt. I was still stroking my hard cock.
Tom had started to rub his cock as well. Debra reached forward with her other hand and grabbed Tom's cock. He let out a small moan as she started to rub it for him. I was imagining the feel of her hand on my cock. Debra then lowered herself in front of Tom and engulfed his cock in her hot mouth. Her experienced sucking was having an obvious effect on Tom as he started to moan louder and louder. He suddenly screamed out that he was going to cum and Debra pulled him all the way in and held him there. I could see him shaking as he came down Debra's throat. Watching my own sister give head to her boyfriend was enough to set me off. I let loose a flood of cum, shooting it across the entrance to the family room.
I leaned back against the wall, my knees weak from the intensity of the orgasm. Tom recovered quicker that I did as he joined Debra on the floor and gave her a deep kiss before pushing her onto her back. He worked his way down her body, stopping to pay homage to her beautiful breasts. He licked and sucked her nipples for several minutes before continuing his journey down to her sweet cunt. I was starting to recover my senses and realized what was going on. My cock hardened again as I watched Tom slowly start to lick around Debra's pussy. Debra was starting to moan from Tom's licking when he suddenly sucked her clit into his mouth. Debra growled and spread her legs even farther apart as he sucked on her clit. I had a perfect view of her cunt from my hiding place. My hand had already found it's way back to my cock. Tom continued to assault my sister's cunt until Debra screamed out in orgasm. Tom kept licking until she calmed down.
When he moved from between her legs to give her a kiss I noticed the damp spot on the floor from where she came. They kissed and fondled each other for several minutes until Debra rolled Tom over, quickly rolled on a condom and straddled him. She slowly inserted his throbbing cock into her dripping wet pussy. When she had taken him all the way in she began to ride up and down on his hard shaft. I was finding the entire thing incredibly exciting but also very frustrating. The way they were now situated I couldn't really see much. I would catch glimpses of Tom's cock disappearing into Debra's hot cunt but it wasn't enough. Unfortunately I couldn't move from where I was without them seeing me.
Luckily, Debra said something the let me see more than I thought I ever would. Debra asked Tom to take her up the ass. I was shocked (and even more aroused) by the dirty language coming from my sister. She was asking Tom to take her up the butt and to fuck her tight hot ass, her verbal tirade continued until she was on her knees (her ass pointed right at me) and Tom had positioned himself behind her. Tom was standing with his legs apart, slightly bent at the knees; his cock was resting against Debra's tight ass. I had a perfect view of her still soaked cunt and of Tom's cock getting buried in her ass. Tom popped the head of his cock into her ass and Debra let out a small scream.