My big sister, who was two years older than I and twenty at the time, would get on top of me with her jeans unzipped and begin dry-humping me through my underwear.  As she worked herself against me, I would use my knees to slowly slide her jeans lower until she was grinding her crotch against me only covered by our underwear.

The more she would work against me, the harder I would get and the friction of her movement would slide the head of my cock out of my underwear.  Once it was exposed and fully hard, I would make sure that as she ground up the length of my shaft that when she reached the tip she would “top out” and push the tip against her panties where the entrance to her pussy was.  When I sensed I was at the opening I would push my hips up.  She would hover in that position and move up and down on the tip.  I forgot the pretense of pretending and started holding my cock straight up and letting her hump it.

Eventually, I started leaning forward and running my fingers over her ass.  I would get as far under her ass to her slit as I could.  As she rubbed her clit against my cock head I would start fingering her and slipping my middle finger inside.

This also started escalating and soon she began slipping her panties off altogether.  By now it was naked pussy against naked cock.  I made sure that as she ground against my shaft that I could feel her wetness covering the length of my cock and making it slick.  She still got to the tip and applied pressure but she attempted to keep her pussy from opening up in full.  She’d even slide the tip of my cock past the opening and slip it past her ass.  I held on to her ass cheeks and started pulling her pussy lips slightly apart as she humped me.  Eventually, I knew that the tip was going to hit that slick and hot part of her pussy opening that was one push from heaven.

She seemed to relish the new sensation and even held that spot while avoiding pushing the head inside.

I held her hips and whispered, "Slip it inside – just the tip.”

“I can’t,” she said but she also didn’t move off.  

“Go ahead,” I answered, “I’ll tell you when I have to pull out.”  

“Do you promise?” she asked. At that point, I would have promised her anything.

She reached down and circled her hand around the shaft of my erection.  She stayed on one knee and slid my cock up against her slit until she eased it against that hot slick opening.  Now she eased the head inside her pussy and asked, “Are you okay?”  

I mumbled something and she started working the head in and out by moving her ass up and down.  I felt her pause and then she eased down so that I slipped deeper inside.  She gasped slightly before settling all the way down and I felt the tip of my cock hit against the back wall of her pussy.  She was red hot inside.  I reached up and pulled her shirt over her head so that I could watch her tits bounce as she rode me.  I played with her tits and glanced down to watch her hips bucking and bending my erection underneath her hot wet pussy.

She rode me for a good thirty minutes before I felt the friction weakening my resolve not to cum.  That and watching her massive tits sway had taken their toll on my vulnerability.

I warned her, “I’m going to cum soon.” 

She angrily muttered, “Fuck!” and quickened her pace as if moving faster might make her cum before I did.  

That isn’t how it works, but I wasn’t complaining.

I reached down and slipped my wet cock out of her pussy and as it was pointing straight up, a hot stream of cum shot up over her tits onto her neck.  It kept spasming and the semen coated her sternum and ran down her neck and tits over her tummy.  She ground her sopping wet slit over my balls until she came too.

Wow.