My Friend's Mother And Grandmother

When I was 14 I had a friend who was 12 that lived a few houses down the street. His Grandmother adopted him when he was little, as his Mom was killed in a car accident. Every once in a while she(I think she was 45 at the time) would say inappropriate things. Like one time I was over and my friend and I walked through the living room she was in. She reminded him to take a shower today. Then she said, "and make sure you clean that little willie of yours. I'll bet Sam(me) has a bigger pecker than you." I didn't respond other than getting an embarrassed look on my face and a bit flushed. Evan said, "Mommmm" and we walk to his bedroom. We didn't talk about it. She seemed to always have an alcoholic drink in her hand. That might explain some of it.

Ok, time to get right into it. Evan and I had started masturbating in front of each other the past 4 months or so. That is another story, but suffice it to say that it started one day when I was over at his house and no one else was home. Evan found a hardcore porn VHS cassette in his parents closet. We watched it and couldn't help but pull our dicks out about half way through.

About a month after the 'bigger pecker' comment Evan asked me to sleep over. So, when we decided to retire to his room for the night, we grabbed some snacks, shut the door, climbed up on his bed(we would both sleep in his bed when I slept over), and started watching TV. About 20 minutes into the show(I forget what we were watching) I look over and Evan is rubbing his hard little dick through his pyjama bottoms. This got me going a bit and within a few minutes I was rock hard myself, and proceeded to slide my hand down my bottoms and grabbed my dick. I then proceeded to stroke it.

Evan noticed and slid his hand in his bottoms and began doing the same thing. I was usually the instigator in these situations, and true to form, feeling a bit horny, I pulled my dick and balls out the fly of my pyjamas. As I began to jerk my newly freed and very hard cock, Evans started watching me instead of the TV. Feeling naughty horny, I asked him to take his out. He did and I began to watch him also. By the way, of course mine was bigger. I was 2 years older than he was. By Evan and I already knew that before she made the comment. After a bit I pulled my PJ's down to mid-calf and started stroking hard and fast. As I slowed down Evan pulled his PJ's down, also to mid-calf.

So, about 25-30 minutes into our jerk off session, all of the sudden the bedroom door opened and there his Grandma stood(apparently she wanted to check on us because the light was still on and it was getting late). We both froze. We didn't have time to pull our bottoms up, so Evan grabbed his underwear and laid them over his groin, and I just had my hands covering me.

I thought her expression on her face was strange at the time. Now that I look back it seems like it was part surprise and part excitement. When she spoke I could tell she had bit too much drink. She said, "Well, just checking to make sure you go to bed soon, but I find my boys being a bit naughty. What have we here.". I said sheepishly, "I'm sorry". Even then said the same. With one hand trying to cover myself, I used the other to start pulling up my pyjamas. Evan just laid there with his underwear still covering himself. Then his Grandma stepped into the room, shut the door, and leaned against his dresser near the TV. She said, "Hold on a minute, you're not in trouble, how long have you guys done this together?" I stopped trying to pull up my pyjamas and moved my hand back to help cover my groin. Oh and by the way, no I didn't get soft. For some reason I was still hard as could be. So was Evan judging from the bulge under his underwear.

Evan answered her question by saying, "oooohhh Mommm" and then mumble something about a few months. She said, "Well, let's see what you got, can you guys move the hands and underwear. I looked at Evan and he looked at me, and both of us still horny, hesitantly moved our groin cover. Evan's Grandma in the almost drunk voice she had, said, "Well well, Sam yours is growing nicely, and yours is cute too honey." She continued, "Now guys, you know it is perfectly fine to rub yourselves. It is natural, and I don't mind at all. So you can continue if you'd like." We look at each other again, both with a kind of shocked look on our faces. Both of us mumble a bit about not knowing what to do stuff like that. She says, "come on boys, let's see what goes on in here when the doors shut." She now seems to be slightly slurring some words. Slowly, and nervously, Evan moves his hand and starts slowly stroking his still rigid cock. After seeing him start, I then hesitantly started rubbing my equally rigid dick.

She asked if we liked seeing each other, and we both looked at each other and then said quietly, "uh huh". "Are you gay", she said looking at me, then laughed a little. To be continued ...