While my high school girlfriend and her mom were gone on summer vacation, I had ended up being seduced by her dad. My summer job consisted of taking care of their home and pool, so I was not raising any suspicions at home. Everyday I would bicycle off to the Engle's. And every day I would spend my time sucking and fucking with Mr. Engle. I had progressed to the point where I couldn't wait to get to his house. I had come to love sucking his huge cock and having it rammed up my ass. I couldn't get enough. He had even invited over a co-worker of his once and the two of them had used me all day.
Now, about a week after this had all begun, I was again biking up to the Engle's house. I knew that things would change as soon as Margie and her mom got home, but I was determined to use every minute I had with Chuck.
When I got to the house, I knocked and let myself in with my key. As usual, Chuck was on the chaise lounge by the pool, naked in the sun. The tall trees and shrubbery hid the view from the neighbors.
"Hi, Mr. Engle," I said. Without being prompted, I shucked my clothes and climbed onto the lounge next to him.
"Good morning," he said and he ran his hands down my body. He fondled my prick until it was hard, then squeezed my balls. His hand trailed underneath to my asshole, which he stroked lightly. "Mmmm, you're just as tasty as ever!"
"Thanks," I said and I reached up and kissed him. His tongue insinuated itself into my mouth and we played tongue tag for several minutes. While we were kissing he took my left hand and moved it to his prick. I grasped his huge member, barely able to encircle it with my hand. I marveled at the texture of it and how I could get such a huge monster up my ass. Both my mouth and my ass ached to have it. We stroked each other's cocks while we kissed.
After a bit we pulled apart, out of breath. Chuck looked into my eyes. "Would you like to do something special for me?"
"Anything," I said, wondering what else we could do together.
"It's a little weird," he said, "I don't know if you'd want to do it or not."
"A little weird? As compared to what we've been doing?"
He laughed. "I see your point. Come on." He got up and led me by the hand into the house. We walked through the living room and down the hall. At the end we turned right, into my girlfriend Margie's bedroom.
"You want to do it in here?" I asked. The idea made me vaguely uncomfortable. After all, I still loved Margie didn't I? I still wanted to sleep with her but I didn't want to do it with her dad in her room.
"No, no," he replied hastily. "Not at all. What I want you to do though...." He paused for moment, then continued quickly, "I want you to pick out some of her clothes. Dress up in a skirt, nylons, bra - all that stuff. Then come see me in the living room." He turned quickly and left the room.
I stood there with my mouth open. Dress up in girl's clothes? I was shocked for a moment but then the idea began to build within me. After all, when I'd had the house to myself this summer, more than a few times I had wondered into this room. I'd gone through her drawers and her closet out of curiosity.
Now though.... Dress up in Margie's clothes? I found the idea more and more intriguing. I went through her top drawer and started to select a pair of panties. Then I thought better of it. I probably wouldn't be wearing the panties long. Instead, I found a garter belt and a pair of nylons. I figured out how the belt worked and then put them on. I loved the sheer feel of the nylon as they encased my legs. I was getting a hard on just from the feel. From her closet I found a short pleated green wool skirt. Margie is kind of a big girl so her clothes didn't fit that badly on me. In her middle drawer I found a plain white bra. I fiddled around with that and got it on. Obviously, I couldn't fill the cups. I took some socks and stuffed the bra. Then a simple white blouse, almost like a shirt. It took a bit to get the blouse buttoned. Finally I found a pair of black high heels. They were tight on my feet but they'd do. In stood in front of the full length mirror and admired myself. My long hair worked with the outfit. Too bad I didn't know much about makeup.
I went into Margie's half bath and found her makeup. Might as well try. I found some eyelash stuff and carefully applied it. It seemed to work. Then I found some muted lipstick. I had to apply it a couple of times before I was satisfied. I checked myself in the mirror. Not too bad, I thought.
I gathered myself up and walked on unsteady feet to the living room. Chuck was there, sitting in his chair, a drink in his hand.