It started a couple years back. I'm a 17 year old boy. My Mom and Dad had been divorced for a while now and my Dad was back in the dating scene. Soon enough he found a girlfriend who moved in with him. So one daywhen i was alone, i was horny and i decided to jerk off, and i started to wonder if my dads new girlfriend had "something" to help. 
 
So i decided it was time to snoop, in other words, find stuff that belongs to her, dirty stuff. I searched every where but i could not find anything anywhere. Under the bed, the closet, the bathroom, the dressers, nothing was in there. So i went back to my room and started jacking off again. But in the middle of it i remembered one place i forgot to check. 
 
It was this little drawer that was next to my dad's bed, it was also the side his girlfriend slept on. So i walked in the room towards the drawer. I put my hand on the handle and pulled.. 
 
 
 
 
 
And behold!!! There was a blue dildo in there, and i could hardly breathe because i had never seen one and i knew that her juices were on it. I examined it and at the bottom there was a black base, and when i turned it... it started vibrating. So i grabbed the lube that was in there and went back to my bedroom. 
 
I poured some lube onto my hand, and before i put it on the dildo, i started sucking it.  
 
I'm going to pause here to let you readers know something. I have a fantasy of being a lesbian getting fucked with a strapon. It turns me on, two hot girls going at it. But the strapon thing may continue in another story. 
 
So I was sucking it, thinking of it as a girl with a strap on. When i finished, i put the lube on it and I started jerking the dildo off (figuratively) and i put it near my anus (which had not had anything this big put in it). 
 
 
I touched it and i started breathing heavily. I tried to put it in and i hurt before the tip got it. So i relaxed and just pushed it in, all 7 inches of it. All of a sudden a wave of pleasure came over me and my head shot up (both of them!!!) and i anchored my dildo hand on the bed and started riding the dildo. With every time i sank down on it i moaned as stretched my ass. 
 
Then I turned the vibrator on... and then... i put some lube in my hand and jerked my self off. I started riding up and down again while pumping my penis. With the vibrator hitting my prostate, combined with me jacking off, i had one of the best orgasms ever as semen flew onto my chest. 
 
 
Recovering from the pleasure, i (slightly painfully) took the vibrator out of my ass. Cleaned it off, and put it back. I have done it a couple times since then, but my dad and her broke up. So where else can i get anal satisfaction? Vancouver, apparently, and i will continue there.