Jilly in the Night

One of several Jilly stories..........

I woke up with a throbbing erection. You guys know the one I’m talking about. The one that’s already dripping. The one that almost hurts. The one that’s about to go off all by itself.

Now I figured that I had the same choices I’d had for the last few months. I could lay there and finish the job myself, or I could make a quick trip over to my sister’s bedroom. Come to think of it, there wasn’t much of a choice at all.

I got up and peeled my shorts off. No sense in getting them any wetter than they already were. Then I walked through my bedroom to the bathroom I shared with my little sister Jilly. My dad called it a Brady Bunch bathroom, which is, I guess, old folks’ talk for two bedrooms connected by a single bathroom.

I left the lights off in my room, but I turned the light on in the bathroom and opened the door to Jilly’s room just a crack. The way it worked, we had to pretend that she never awoke, and I couldn’t turn on the light in her room or the spell would be broken. But I couldn’t make my way through the mess on her floor without a quick peek. So I used the light from the bathroom to get a fix in my head where all the stuff on her floor was, so that I could walk around it. Fortunately, her room was pretty neat for a change, and I quickly turned off the bathroom light and quietly walked into the dark of her room.

Jilly was curled up asleep on her bed on her right side, facing me. She liked to dress warm and then sleep on top of the covers, but I never could figure out why. She had on her usual sleeping outfit, a tank top, and a pair of sweat pants. Her feet were bare, and I looked at them lovingly for a moment before I decided that that wasn’t what my dick was really crying out for tonight. I would have preferred that she wore just panties, or even nothing, so that I could watch her long legs and tight little ass while we did our thing, but that wasn’t the way it worked.

Seeing her laying there, her blond hair falling over her face, I got even more excited, remembering I guess the times we’d done this already. My throbbing dick was almost ready to spew all over her just from seeing her angelic face under her short blond hair.

Jilly and I had somehow without ever discussing it come to a kind of arrangement some months before. It always involved my satisfaction, and I was never too sure what she got out of it. I would have fucked her in a New York minute if she’d let me, and she had become the sexiest girl in my existence. I would have done anything she asked. But we’d never actually had sex. One thing I knew for sure - this wasn’t going to take long tonight.

I laid down on her bed, on my left side, facing Jilly. I was careful not to let my dick touch her, because that wasn’t allowed. I put my hand behind her head, kind of wrapped in those blond locks, and eased it towards my dick. She woke just enough to help a little. She bent over at the waist, curling up even tighter, and opened her lips just a little as they neared my throbbing erection. I loved the feeling of her hair in my hand, and then as she settled into place, her hair on my belly.

Jilly ran her lips over the head of my dick, getting her lips covered in pre-cum as she searched for my opening with her tongue. As soon as she found it she stopped moving except for a soft sucking, kind of like she was drinking a pop from a straw. That was all it took.

I held on to my dick with my right hand, pushing down on it as if I was thrusting it into her instead of just barely touching her. The cum poured from me in a stream, and Jilly sucked and drank. I’ll never know how she did it. It was as if she was slowly slurping a milkshake, and not having jets of hot steamy come shoot into her. But she never lost a drop, and she kept on sucking patiently and swallowing quietly until I was all done. This never failed to milk me absolutely dry, and I knew that I’d have no trouble from my dick for the rest of this night.

As I got up from my little sister’s bed she stretched slowly, and sleepily resumed the position she was in when I had first come into her room. Jilly settled in back to sleep and I heard her say softly as I left the room, just like she always did, “Thank you.”