I was 14 when I had this experience. I was small for my age, only 5 foot, but very muscular and tanned.
I had a medium sized cock, about 4 inches when erect, only and 2 when placid and had never got further with a girl than kissing. I should say now that I am straight, however I enjoyed exploring the concept of anal.
I had fingered myself before and even put a tampon inside of me. I had always been intrigued by the idea of incest and found myself often thinking sexual thoughts about my mum. She was in her early 40's, short black hair, had breasts around a 34B and was on the chubby side.
I would fantasize about having sex with her and would seek out her dirty knickers for a sniff or put on one of her bra's and masturbate, however I would always feel disgusted with myself afterwards. We were a very respectable middle-class family, my parents had good jobs and my brother and I both had a private education.
I always feared what would happen if anyone found out about my fantasies. It was late afternoon, my dad was at work and my mum and brother had gone shopping. I was extremely horny. I decided, as I had a few hours alone, to go to my parents bedroom and investigate my mum's drawers.
I had done this on previous occasions hoping to find condoms or lube, anything that indicated towards my parents sex life. I had never found anything though and once again my search through her drawers proved fruitless. I was prepared to give up, go back downstairs and masturbate to some porn when I noticed that the bed my parents had, had drawers attached to the side.
I had never noticed these drawers before and my young cock soon sprung to attention as I imagined what delightfully naughty goodies my mum may have hidden within. There were 4 of these drawers, 2 on each side of the bed. I opened the first and was disappointed to find only an array of my mum's winter jumpers. My erect dick started to droop somewhat, perhaps this search would also be frivolous? The next drawer however soon got me fully erect again, and drops of pre-cum started to form on my 14 year old 4 inch penis.
Inside were a small selection of sexy thongs and lace bras. I picked out a crotch less pair of panties with a small heart where the strings met in the middle. I decided to try them on. I also took a light pink bra. I went over to the full-length mirror in the corner of my parents bedroom and undressed myself.
My dick was now very hard and the pre-cum was starting to drip down the shaft, congealing in my boxers. I placed the bra around my chest and slipped the panties on, watching myself in the mirror, feeling myself get hotter and hornier, wanting desperately to relive my aching balls.
I stroked my shaft slowly, spreading the pre-cum over my cock. Ohhh it felt so good. I decided to keep looking, not yet satisfied with only lingerie. I went to the other side of the bed, my dad's side and opened a drawer. Again the first drawer was empty of sexual things, the second however held something I never thought my parents would ever own. A dildo. A vibrating rabbit dildo. I stood for a few seconds stunned by my discovery. It was bright red and about 6 inches long. At the base were 3 buttons letting you control the direction the shaft swivelled, the intensity of the vibrator and the pace at which it rotated.
Lying next to the vibrator was a tube of lube. Once again my balls ached and I was ready to squirt my load then and there, looking at the device which had no doubt driven my mother to orgasm after orgasm. I imagined her naked on the bed, legs spread wide, her hairy pussy being rammed with this machine. The feeling of ecstasy as she had her orgasm. I wanted to feel it too. Ohh it was getting too much to bear, I had to release my load, thinking about my mum cumming made me want to cum so much!
I reached out and took the vibrator, pulled it up to my face and sniffed. It smelt quite musky and you could see bits of her dried juice smeared over it. It had obviously been used recently. I tentatively stuck out a tongue and licked the shaft which had once been deep inside my mother.
It tasted strange, quite bitter and I wasn't sure I really liked it. None the less, I was hornier than ever tasting my mum's cum, something I had wanted to do for a very long time. I leant down and picked up the lube in my other hand. Suddenly a wonderful idea came into my head: the vibrator which had recently penetrated my mum, could penetrate me. I liked fingering my ass and the lube would help make it more pleasurable.
I squirted some onto my had and lay down in front of the mirror and placed my legs in the air. I rubbed the lube around my hole, fingering myself to loosen up for this dildo.
Once again I was close to cumming.
I turned on the vibrator and slowly pushed it against my crack. "Mmmmmm Ohhhhhh Ahhhhhhh" I cried with pleasure as it pulsated against my ass. With my other hand I started stroking my cock, slowly at first, teasing myself, making my moan more as I pressed the dildo into my bum. It was too wide however and my young teenage ass couldn't take it, it wouldn't go in.
I was determined however to penetrate myself with this magnificent machine and instead took the vibrating rabbit which was significantly slimmer and pushed that slowly into my bum.
I wriggled it around slowly before suddenly it sunk all the way in, all 2 inches of the rabbit were deep inside of me. I groaned loudly and moved my hand faster over my cock, feeling my balls get closer and closer to release. I looked at myself in the mirror, saw the dildo moving in and out of my ass, imagining my mum lying on the bed, pleasing herself with it. "Ohhhhhhh Ahhhhhhhh Mmmmmmmm Ohhhhhhh" I screamed out loud as I neared orgasm.
Ramming the rabbit in and out as fiercely as my little hand would go. Wanking furiously I felt my balls tighten, my legs tingled, my ass clenched and I squirted the largest load I ever had right into my mum's panties. "Ohhhhhhhhhhhhhhhhhhhhhhh" I cried as I watched the white goo erupt from my still hard young cock into the black satin of the knickers.
I collapsed onto the floor, the rabbit still rammed up inside of me, and sat there for a few minutes, my young body still quivering after my biggest ever orgasm. Slowly I stood up and extracted the dildo from my butt.
I looked at it and once again imagined my mum, this time lying helpless on the bed after a furious orgasm. I put the panties and bra(unwashed) back into the drawer, a little present for my mum.
I also put the dildo back into the drawer unclean, dirty just the way I had found it. I thought of my mum fucking herself with it, only this time she'd have some of me left on it.
This made me horny again and before I knew it I was stroking my still hard cock once again. I ejaculated quicker this time, still wiped out from earlier and the little squirt that came out went into her panty drawer.
Slowly I dressed myself again and went downstairs, just in time, as a few minutes later my mum and brother returned home.
I said hi to my mum and looked at her bra, just visible above her top. I could feel my cock getting hard once again, thinking about that sexy lingerie I had found, imagining her in it, penetrating herself with the dildo.
I hoped that she and my brother would have to go shopping again soon.