The summer before my freshman year was going to be filled with parties, beach trips, and girls... Or so I thought. Early on in the summer my dad made it very clear that I was going to be working and saving as much as possible before I left for college because he didn't want to "pay for all my beer." So, my summer then turned into cutting grass and babysitting on a regular basis. I'm about 6'3, brown hair and hazel eyes. I played football in high school, so I kept in pretty good shape. Cutting grass in the heat wasn't half bad, it kept my tan and fit, but babysitting was by far the easier summer job.
I babysat for 2 different families. The Johnson's and the Blake's were every once in a while, so the parents could go out to dinner or a movie. I used to love babysitting for the Blake's, simply to watch Mrs. Blake leave. About 5'11, long blonde hair, blue eyes, shapely. And did I mention double D's? She was the classic vision of female sexuality to me. The Blake's had one daughter, a 5 year old girl named Jessica. Jessica was born in China, but the Blake's adopted her because they couldn't have children for some reason.
I don't classify myself as gay, or straight, I like to experiment, and I like anything that feels good. Temptation always seemed to win out when I was in the shower and those two soapy fingers looked so ready to go somewhere naughty.
So the reason I'm writing is about an encounter I had that was a first for me, of sorts. The Blake's had asked me to babysit Jessica for the evening so they could go to dinner, and I agreed, knowing how well they payed. I arrived at their house at 6 PM.
"Hey Justin, come on in!" Mrs. Blake said, answering the door.
"Hi Mrs. Blake, how are you?" I replied.
"Please, Justin, call me Kim, I tell you every time!"
"Yes Mrs.... Kim..." I replied, always a bit nervous around her.
"Go ahead, Jessica is in the living room watching TV. She went to the zoo today, so shes a bit tired, should be in bed early tonight." Kim informed me.
I watched as she walked away, The silk red cloth of her dress sliding along her curves and putting rather dirty thoughts in my head. I walked into the living room to find little Jessica half asleep watching cartoons. I sat next to her and asked what she was watching.
"Adventure time," she said, following it up with a big yawn. We sat on the couch in silence, watching the cartoon until Mr. and Mrs. Blake came in to tell us they were leaving.
"Have fun guys," I said, again mesmerized by the way Kim's butt looked in that dress.
"We'll probably be late, once Jessica is in bed, feel free to take a nap on the couch," Mr. Blake informed me.
"Will do, Cya." I said.
Me and Jessica watched TV for a few hours, I made us mac and cheese for dinner. By 8:30, she was ready for bed. I took her up and tucked her in, read a bed time story, and left the room. On my way down the hall, i caught a whiff of perfume, it smelled like Mrs. Blake. I turned toward her room, which I had apparently just passed, and pressed on the door. It slid open without a noise so I stepped into the dark room. Upon turning the lights on, my eyes were first drawn to the large four post bed in against the wall. Red satin sheets were draped across it, and the wooden posts stood as dark polished wood. I moved over and sat down on the bed, finding it soft and comfortable. My eyes fell upon the dark side table, and I pulled open the drawer. I immediately closed it, seeing an array of sex toys displayed on top. My curiosity, however, got the best of me.
I opened the drawer back up and examined the toys. There were handcuffs, lubes, and three dildos. One, slender, and purple. Another, about 7 inches, and flesh colored. The last, much much larger, and jet black. I'd never actually held a dildo before, so I picked up the black one and examined the fake veins and balls on it. It was think, I couldn't fit one hand around it. I set it back down and picked up the smaller purple one. It was made of something somewhat translucent, and had a suction cup behind the balls. It was a about the size of my penis, 6 inches, and had a similar girth. While holding it, I realized, this was inside of Mrs. Blake. My eyes widened and I brought it close to my face. I smelled it, I tasted it. I took the shaft into my mouth and tried to taste anything Mrs. Blake had left behind.
My eyes then were drawn back to the open drawer, a bottle of KY sitting among the toys. I pulled it out and popped the cap. Why not, I thought to myself, it's not like I haven't had fingers up there before, and this could be fun. I stood up and undressed, getting completely naked. I got on all fours on the bed and took the dildo in my hand and the lube in the other. Once ready, I pressed the tip against my asshole and felt the pressure as I pushed harder. I pressed until I felt the POP of the head breaching, and sighed, the feeling quite nice. I pressed further, taking the dildo deeper. It felt amazing, being filled up, the pre-cum already dripping from my cock. Once I felt the balls against my own, I pulled it back out slowly, trying to keep it in, but then I felt the head pop out of my ass. I went in again, repeatedly taking the purple cock in my tight ass. I took my other hand and grabbed my cock, I began stroking, slowly, because I knew my load was like a dam waiting to burst. My face in the pillows, I bit down hard on one to stifle a gasp as the cock filled my ass again and again. I stroked harder and faster, feeling my orgasm coming. I worked both hands furiously, loving the feeling of the purple cock filling my ass, and gasping as my cum started pouring out of my cock. The feeling of the both the filling and the emptying of my cock was amazing, I came what seemed like gallons. I left a large puddle on the bed spread, and let the dildo fall out of my ass, staying in my position, my ass high in the air. After a few minutes I fell to my side and rubbed my face, quite satisfied. When I pulled my hands away, I saw Mrs. Blake. Standing in the doorway. Staring at me.
