The first time it fit Sex Stories Cool – Y2 Stories

She was a hard sleeper and tonight was the night I was going to test it

It was 6 days after her 10th birthday.
I was 14.
She was asleep on the couch. Everyone else in the house was already asleep in bed.
I had already pulled her pants down a few times at night and had even started finger fucking her asshole while I jerked off on her.
Tonight was different though.
You see, last night, when she finally fell asleep in my bedroom, I pulled her panties down and started finger fucking her tight asshole. I was really giving it hell too. I was using my middle finger and was pushing it as far as I could up her ass. I decided that if she can’t one finger, and the biggest finger on my hand, let’s see if she can take my thumb up her ass.
Sure enough, it slid right in there. She clinched up when it got really deep but there it was, thumb deep in her ass and her fast asleep.
So I got brave!
Two fingers it is!
I started by pushing my index in first. Once I got it to the second knuckle, I started pushing the middle finger in. You could feel her asshole reached it stretching limit and she clinched up really tight when it did, tight enough to push the tip of my middle finger back out of her ass.
Her clinches didn’t deter me. I pushed the tip of my middle back up her ass and stretched her asshole out to its limit again. She clinched up really tight again but I refused to let her push me out. She slowly relaxed and there it was, two fingers almost knuckle deep in her tight little ass and she’s still fast asleep.
I started cumming like a faucet when she relaxed with that much in her ass.
I decided right then, tomorrow night, you’re getting sick and I’m going to cum in your ass.
Tonight was that night.
I started by pulling her little ass over to the edge of the couch and started pulling her pajama pants down in the back all the way to her thighs. She had on her tight fitting panties tonight. That sucks. Those are really hard to get off of her. I was determined to cum in her ass though. It took me about 12 minutes of slowly tugging and pulling to finally get her tight hairless asshole out in the open, but I got it done.
My cock was already covered in precum at the thought of fucking her ass. I poured a decent glob of baby oil all over my hands and started sticking my fingers in her ass. My dick was a little larger around than two fingers and a lot longer than two fingers so I knew lube was going to be a must.
After getting her asshole stretched out and lubed enough to take my thumb again, I decided it was time for sissy to get her first buttfucking. I doubt she would’ve been as excited about it as I was in that moment, but that wasn’t going to stop the fact that she was about to get a full sized cock in her ass.
I leaned back to get a good look, spread her firm little cheeks apart and placed the head of my baby oiled cock at the entrance to her virgin ass. I slowly started to push it in.
It wouldn’t fit.
I pushed even harder and she started to flinch and pull away. I let her pull away and then pulled her tight ass over the edge of the couch again and lined her up for round two.
I pushed again and nope, not going to fit. She kept clinching up and pulling away from it.
My cock was just too big on its own to fit in her ass.
I was so disappointed.
I then had a wonderful idea!!!
What if I grab my cock at the head, grip it really tight, and push all of the blood that I can out of it, get it as little as I possibly can, then push it in her ass.
So I tried.
It hurt a little to push all of the blood out of my cock. I mean, I was rock fucking hard in that moment but I knew, tonight was special and there wasn’t anything going to stop me from cumming in her ass!
I lined my pale stiff dick up with her asshole again and started to push.
She gave a little clinch, just a little one, relaxed, and boom, I felt my cock slowly slide past her asshole and into her colon. I leaned back to give it a visual confirmation and sure enough, my dick was about 2 inches in her ass and still going. I pushed and got about 5 inches in her before my hand holding the blood from my cock got in the way.
This immediate warmth shot all over my body like magic. It was heaven being inside her tight little ass.
I couldn’t help but to let go of my cock and see if she could take it.
The moment I let go of my cock and felt it grow to size inside her colon, I immediate started cumming.
I grabbed her hip and held her still so she couldn’t pull away.
Her asshole got so tight when I started to cum that she would clinch and it was seriously stopping the cum in the shaft of my cock. She would relax and the next thrust would shoot it in her. I felt the cum come back past the head of my cock, as if I had actually filled her ass with cum and it was about to start oozing back out. I slowly started pulling my cock out of her ass. I had little brown shit nuggets behind the head of my dick and the moment my soaking wet cock fell out of her ass, a 4 oz glob of cum oozed out of her gaping asshole and onto the cloth couch.
I wiped her gaping asshole up with my t shirt, pulled her panties and pajamas back up to cover her blown out ass and went bed, still wearing her booty juices on my cock.