My Lovely Sister: Part III: Venturing Into New Territory

Friday,July 3 rd , 2009...

I had been really disappointed to see that Mandy had off from work the next day. I didn't think I'd get to masturbate in with her clothes at all. However, lucky for me, Mandy had gone off to a friend's house early that morning. Needless to say, I wanted to continue my new routine of going through her clothes, picking out some panties, and masturbating to them. So I headed off to her bed room, this time completely naked. I wasn't hard yet, but I knew I would be soon.

By the time I had reached my sister's bedroom, I found myself consumed by a new desire. It was totally out of my character, but I just couldn't get the feel of Mandy's panties wrapped around my cock out of my head. How good it felt, to know that something that was once on my sister's pussy had also been on my cock! It was probably the closest I would ever get to actually fucking her, though a boy can dream, can't he? So this time, I wanted to take it a step further.

I was going to wear my sister's clothes.

I began immediately digging in her laundry hamper, still not bold enough to look through her clean—folded—clothes. The first thing I managed to find was a pair of pastel pink, cotton, boy-shorts panties. I stepped into them so quickly that I nearly lost my balance. But now with both legs in, I convinced myself to take it slow, to savor every moment. Hence I gradually moved the panties up my legs, until they were snug against my cock and butt. However, my cock was already pushing the front forward.

“Keep digging,” I told myself aloud, returning my attention back to the laundry hamper. As it was, I was already so horny that it was difficult to think. The next thing I grabbed was a white sports bra. I didn't care in that moment that it was a sports bra and not a cupped or lacy one; I simply hurried to get it on.

“Only one more thing,” I said again to myself. One more thing was all I'd be able to handle before having to pleasure myself. As it turns out, that one more thing was a pair of tan pantyhose. I stepped into them one leg at a time, and before I pulled the first leg just over my knee, I was already poking out the top of my sister's panties. They could no longer contain my erection. Still, I paced myself in covering my legs in those smooth, silky pantyhose. Once I had pulled them all the way up, I couldn't believe how sexy they made my legs feel.

As I turned to the door, wanting to masturbate in my own room for a change, I caught a glimpse of myself in Mandy's full body mirror and stopped. “Wow,” I said softly. “I look just like her!” As I had spoken those words, I found myself rubbing my cock lightly with my middle finger, and pinching my nipple through the bra with my free hand. Both the panties and the pantyhose that I wore were stained with pre-cum in the front by now, and I was overwhelmed with another idea. Still looking at my cross dressed body in the mirror, I pushed my cock through the right leg hole of my sister's panties, and pulled the panties as high as I could stretch them without ripping them. I could feel the soft fabric rise between my butt cheeks, no doubt showing the slight curves of my ass; I moaned at the sensation.

Next, I pulled the pantyhose up as well. These stretched further than the panties, and I found myself able to tuck the top of them underneath the sports bra that I wore. This much stretching made them feel tight on my legs, making them feel even silkier and sexier. “Oh, God,” I moaned at the extreme level of pleasure. In this manner, I quickly returned to my bedroom, not even bothering to close the door. I pulled the front of the pantyhose down to expose my rock-hard cock, trying to leave the sides and back up as much as possible.

Then, as firmly as I could, I took a hold of my cock and began masturbating. I was leaning my back against the wall, while pushing my hips forward. I moved my hand quickly and harshly, nearly pounding myself with every back stroke. I had been imagining that my hand was actually Mandy's hand, and I was pretty sure my mind temporarily convinced me of that fact.

“Oh, Mandy!” I shouted, as loud as I could, my eyes closed tight. “Mandy! Mandy!” I cried. Finally, I exploded, without even knowing it was coming. “UH!” I quickly squealed, squirting my load forward. It shot so far that I nearly hit my own bed. By the time I was finished, there was a trail of my own semen leading from where to stood to the foot end of my bed. I decided that, rather than clean it, I would lick it. I got down on my hands and knees, and licked the entire trail of cum, not swallowing it until it was all in my mouth.

“Mandy'll have to do without these for today,” I said aloud. I kept true to my word that day; I put on my jeans and t-shirt right over my sister's underclothes, and even let my feet remain exposed. All it would have took to get caught was someone later looking at my feet, and spotting the pantyhose.

Fortunately, no one noticed.