Chapter 2

My littlest victory was so sweet, stripping mother down to her bra, I didn't wait another week. Three days later, just about the time my bum was able to sit down in a hard chair again, I stole her skirts.

Mother retrieved her clothes straight away, this time wearing only her blouse and a heavy cotton girdle. I wasn't nearly as excited by this state of undress as a more experienced boy or man might have been. Yet I didn't miss the shape her full-length, black stockings assumed. If Pepsi had made their bottles in the shape of my mother's legs, Coca-Cola Corporation would be a penny stock today. My goal however, was motivated by my memory of one of her naked breasts. I'd never even heard of cunt. If I succeeded in exposing both of her nursing bottles to me, I would title myself Calvin the Conquerer. Her tall, sturdy girdle left far too much to the imagination. Her reaction to my second theft left none.

Expecting the worst, I awaited her in the living room 'in one minute'. Mother entered and sat down beside me on the couch. She had not put on a skirt to conceal her dove white girdle. Her semitransparent stockings smoothed over each of her legs without run or blemish.

"I'm not going to beat you again Calvin. This strange obsession of yours has me worried, and I want you to know that I will try whatever it takes to cure you. Obviously, physical punishment has failed." She left the conversation open ended.

Take off your bra mommy, and let me jack off all over your tits, and I'll be fine, I heard the base of my skull comment. I sniffed to conceal my internal chagrin.

"But mommy, all I want to do is wear your blouse." I tried pouting.

She looked at me strangely.

"Calvin," Mother asked me very slowly. "Do you wish you were a girl?"

"No!" I blurted, then I hesitated, "I-I don't think so." I suddenly wondered if there was an answer that would move her closer to my goal. Unfortunately, my first outburst came from a straight boy's natural commitment to his sex. Fortunately, I shrouded my words with a shred of doubt. Unfortunately, I was sporting the hardest erection my pants ever had to contain.

"It isn't right for a boy to want to be..." She glanced down at my zipper. "... be uh, something other than uh, a boy." Her voice fell to a whisper. "But sometimes God has reason to confuse us." Her eyes confronted mine patiently. They held no shame at their brief distraction at my erect dick.

"What does God want me to be?" I tried to play the innocent, striving to casually cover my lap with my hands.

"He wants you to be good and not steal your mother's clothes."

Round Six: Mom - 6, Calvin - Zero. I guess she'd earned the previous point too.

Round seven didn't happen for another two weeks. My mother's reaction had blown me away. Still, I didn't let pass that brief moment when mother noticed my hard cock tenting my pants. It was important, I knew it instinctively, but having only an upper body centric eroticism I was unable to understand either her glance or her willingness to wear underwear right next to me.

I acted without purpose or plan when round seven finally occurred. One early morning, I got up to use the bathroom, but mother was showering. My piss hard-on wasn't desperate so for some reason I wandered into her bedroom where I found her clothes neatly laid out on her bed. I picked up the bra and wrapped it around my chest, but I didn't fasten it. I simply held it together behind me. I didn't even put my arms through the straps. They fell down against my belly and sides. I was imagining her breasts filling this inexplicable contraption, not my own flat chest. After a few moments I returned the bra as closely to it's original place as I remembered. I turned to her less fascinating, but still intriguing girdle. I picked it up.

"Go ahead and try them on." Her soft voice surprised me. Mother had entered the room behind me.

I turned around, ready to bolt through the door, but her quiet composure reassured me. She was wearing three towels. I was wearing my jockey shorts.

"Uh, I guess I don't really feel like it." I fumbled once again.

"Okay, that's fine." She nodded plainly. "Now scram. Mommy has to dress."

Exactly one week later, I asked her again.

"Mom, can I wear your clothes?"

Mother looked surprised for the very first time. "Calvin, what do you really want? Can't you just simply ask for that?"

I very much wanted to ask her to strip naked for me so I could beat my rampant cock in front of her and spew my cum, hopefully dousing her with it, drenching her with my cum. Instead, I asked her an even stupider question.

"Can I wear those clothes?" I said, and I meekly pointed at her widow black, extra plain blouse.

"Do you mean, the clothes I'm wearing right now?" Mother asked apparently beguiled by the possibility. Later on, I learned that she never considered the idea that her son just wanted to strip her naked. That sort of motivation didn't occurre to her. Not only was she a prude herself, she naturally assumed that I was sufficiently indoctrinated and far too young to harbor anything but innocent evils. Instead, she had constructed an entirely different rationale for my requests to wear women's clothes. She thought her only child was confused about his gender or possibly his sexual orientation. Mother didn't know what to make of my more specific request. "This?" She queried and plucked at her upright collar.