How my affair with my family's smoking hot babysitter began
Linda has babysat my brothers and me during the morning and afternoon for years. She comes over to my house on Tuesdays, Wednesdays, and Thursdays. She is about 5’5”, slightly over 100 pounds, and is hot as fuck. She has blue eyes, black hair which I dyed blond, is thin, and has one of the best combination of curves and legs I have ever seen. She is about 60 years old, which may seem too old to want to fuck. However, I have never lusted after a woman so much in my life. In my early high school years I began to realize how hot she was. When I would come home from school and see her hot blond hair, her beautiful tits, and nice round ass, I often could not help but go up into my room and jerk off. After months of fantasizing, I reached a point where I just had to have her. Due to inexperience, I did not know how to go about it. She was not the type of woman who would tell my parents if I misbehaved, or even went as far as to make a sexual pass at her. However, I did not think that she would voluntarily sleep with me, so I had to find another way. I was able to get my hands on some roofies through a guy at school, and slipped them in her drink one afternoon. When she started to feel sick and tired I said that she should go up to my parents bed and take a nap, which she did. Once she was passed out, I took her body and brought her up to the third floor of my house. I laid her on the floor, and slowly began to undress her. I took off her clothes and felt her up, I could not believe that I was actually rubbing Linda’s hot body. My penis was hard as a rock in no time. At last she lay there naked in front of me. I quickly undressed myself, and thought about what I should do to her. I came to the conclusion that I did not want to ram my cock into her pussy or ass, because she would know that she had gotten fucked when she woke up. So I flipped her over on her stomach and rubbed my fat cock all over her ass and in between her butt cheeks, and spanked her rear end a few times as well. I then flipped her back over onto her back and felt up her boobs, proceeding to rub my penis around them. I then strattled her head and stuck my meat in her mouth. I rubbed my bulging cock head all along the inside of her cheeks and along her tongue. Pre-cum oozed out as I took my piece out and smacked in the face a few times with it. I wanted another piece of her ass, so I turned her back over, laid on top of her, and humped her naked butt. It was so tempting to ram my big penis into her from behind, but I wanted he to think that she had just fallen asleep when she woke up. After dry-humping her for a while, I put her on her back and got between her legs. I wrapped her legs around me and imagined how good it would feel to actually fuck her sweet pussy. However, since I could not, I strattled her stomach, rubbing my dick on her tummy as I cupped her breasts with my hands. They were nice and round and felt and her tits felt oh so good. I then squeezed his boobs together and began to titty-fuck her. I put some spit on my cock so lid in between her boobs nice and easy. My penis got really hot, and when I felt that I was going to cum soon, I got up on my knees and started to jerk off right next to her face. The site of her naked body in front of my and the thought of me molesting her like I had just done soon brought me over the edge, and a couple streams of cum shot across her face, getting in her hair, her eyes, over her lips, and on her chin. As more cum oozed out of the head of my cock, I rubbed it on her cheeks. Once I had finished up, I took a picture of her naked body with my cum on her face. I then wiped my load off of her, put her clothes back on, and carried her back downstairs to my parents bed. I was sure to rub her tits a few more times on the way.
What I did to Linda while she was drugged got me off for several weeks. However, I soon had a deep desire to penetrate that tight little ass of hers. I just had to be in her. Not only did I want to fuck her in the butt, but I wanted her to scream and struggle to get away while I did it. I soon saw a perfect opportunity to get her right where I wanted her. It was just past noon on a Thursday, and school had been let early due to teacher meetings. I had not been aware of this early dismissal, and neither had anyone at my house. My carpool ride showed up on time, and dropped me off near my house about 90 minutes earlier than usual. As I entered my house through the side door, I noticed that Linda was not downstairs. From upstairs I heard her yell down to the kitchen and ask if anyone was home. I was about to respond when a dirty thought that was just too tempting to pass up popped into my head. Instead of answering her request, I remained silent and snuck upstairs to my room. I quickly got a hard-on from the thought of what I was about to do. I quietly moved around my house until I pinpointed her location. She was on the third floor of my house dusting cabinets, as a good bitch should. Her back was facing me, and I saw my opportunity to move in. I pounced on her from behind, causing her to let out a loud scream. I quickly cuffed my hand over her mouth and squeezed her cheeks shut. I brought her down to the floor so she was on her stomach, and then proceeded to get on top of her to completely subdue her efforts to escape. I made sure to keep her face looking forward so that she would not see my identity. I then proceeded to lift her sweater and shirt up over her head, and tied the end in a knot. Now she could not see at all. She could scream, but no one would hear her because the rest of the neighborhood was still either at work or school. The more she screamed, the hotter the fuck would be. Now that both of my hands were free, I brought her hands behind her back and held them together with one hand. With my other hand, I undid her bra and let it fall to the floor. Her hot breasts now dangled before me. She was now on her knees with her smothered face grinding into the carpet. I then undid her tight jeans and pulled them down to her knees, along with her panties. Her exposed asshole was now right in front of me, and I could not wait to ravage her with my big cock. While holding her in place with one hand, I quickly spit on my hand to lube up my penis and her asshole. Once my moist fingers began to penetrate her rear hole, she struggled even harder to get away from me, but she never stood a chance. I could completely dominate this old maid. I was ready to enter her, so I placed my cock head at the entrance to her asshole and slid my slippery penis inside of her. She let out a scream that rattled the windows. At first, because she tightened up so much, only the head of my cock went inside of her. But she was so tight that I leaned my head back in ecstasy. I smacked her in the ass a few times and then pulled her butt cheeks apart with my hand. I then slowly started applying more pressure, and pushed further and further into her hot rear end. She moaned louder and louder as my humping caused increased penetration. She begged me to get off of her, but that just turned me on more. Anyways, with the amount of money my parents were paying this woman for her bitch-work, she better learn to take a cock or two while on the job. My humping continued, and when my meat stick was about half way in, her anal muscles began to loosen up a little. She began to get used to my penis being in her ass, and realized that it was useless to try and escape my grasp. With access to her ass now a little easier I let go of her arms and grabbed her waist with both of my hands. I steadied myself and then began thrusting my dick into her asshole fast and hard. She screamed and moaned like the slut that she is, telling my how big my juicy cock felt in her ass. The thought of me actually corn holing this beautiful blonde babe who I had fantasized so much about, along her gasps as I ravaged her tight ass, soon brought me to the brink of ejaculation. I wanted to yell out as I exploded into her, but I could not because she might recognize my voice. With one final, deep thrust I went balls deep into her ass and held my penis there as she wiggled around, screaming in shock. I continued to press forward, sending several shots of cum deep into her ass. I held her there until all of my seed had oozed out into her rear hole. After a final smack on the ass, I pulled out of her, quickly pulled up my pants, and snuck back out of my house. I did not return until the usual time that I arrived home, so that I was free of suspicion.