I Knew, (sort of)

I knew, of COURSE I knew. As long as I could remember, I'd been told I was too pretty to be a boy, and how much like my mother I looked. AND, I didn't really mind, until I hit high school, and was badgered and bullied by the jocks. With girls? I was a bestie, nothing more. It was rare for any of them to look at me as more than one of them. I was in my last couple of months of school, and already 18, because I started school late, was looking forward to college, with the hope of something different.

So... of course it was on my mind... a LOT. At eighteen, I'm almost exactly the same size as my Mom, minus boobs, of course. And, as you probably already guessed, my curiosity lead me to her clothing. Like most, it started with her underthings. My Mom had always been beautiful, and until the last year or so, had always shown off her small, slim, sexy body. Short, tight dresses, heels, she made every man's head turn. I watched, studied, how she put her makeup on, and styled her hair. She thought it was innocent curiosity, and at first, it was.

As time passed, though, she was a living tutorial, and anytime I knew she and my stepdad would be gone for more than a few hours, I was replicating every move I saw. The first time I dressed fully, I came in her panties. The feeling was indescribable. I wasn't a boy, constantly teased, I was a hot girl. I was elated at the transformation, but scared at what I had opened, too. When I looked at the girl in the mirror, I knew at some point, I would pass the point of no return. That first day, I raised the hem of that dress and jacked myself off three times. I could not get over this feeling of sexuality. From that point on, I had to be VERY careful of making sure every item of clothing was put back where it belonged, cleaned and folded, or hung up.

I can't remember my dad. Mom said that I wasn't even walking before he decided he wasn't a family man. Yes, child support checks came once a month, but never a birthday card, or Christmas card, My Mom married my stepdad when I was 5, and he's always been pretty good to me. I think there was some disappointment that I wasn't a typical boy, but he hid it well. Up until this last year, he and Mom seemed the perfect couple. She'd get all "dolled up" as he put it, and they'd go out on regular dates, be it movies, dancing, or whatever. Not as much these days, and I haven't seen her in nice dresses in months. They weren't fighting, but definitely not as close.

Two nights ago, at dinner, Mom told us that Aunt Meg had a car accident, and she was going to see her in the hospital, and stay for a few days, until they were sure what her condition would be. She went into work, to arrange time off, and set up facetime meetings with her bosses, if needed. This morning, She kissed us bye, and headed for the airport. My stepdad, Clint, left for work right after her. Right after I called school, and said I was sick, I started my ritual. I jumped in the shower, freshly shaved everywhere (which is fast, as I'm not very hairy to begin with), and got out, immediately blow-drying and styling my hair. I pulled out my favorite bra/panty set of Mom's, a red satin demi cup bra, (stuffed with stockings) and french cut matching panties. Then the nearly sheer nude stockings. I slipped on her four inch ankle strapped stilettos, and sat to do my makeup.

My heart was racing as I put just the lightest touch of foundation, then translucent eye shadow, and mascara and eyeliner. Seeing my Mom in the mirror in front of me, I completed her look with luscious glossy red lipstick. GOD, I loved the feel of it. Satisfied, I stood, slipped on the body hugging red dress that made every man who saw her, drool. I turned on some music, and started dancing. I was trying every sexy slither I'd ever seen Mom do, reasonably convinced that I could turn heads too.

For the first time, I wondered if I dared go OUT like this. My whole goal was to make guys look. I don't know why, but I'd never thought beyond that. It hadn't occurred to me that somebody might want to do more. Anyway, I was deep in my fantasy, when I caught something in the mirror, behind me. I froze.

"Beth, what are you doing back home, and.. Why are you wearing my favorite dress? Was this just a story? Did you plan to surprise me?" My stepdad stepped into me, his hands on my ass, and slipping around me. "Mmmm, that ass is still as fine as the first time I touched it!" He swung me around and leaned in to kiss me, when he saw the shock in my eyes, my mouth wide open. "WHAT... The.. HELL? Nathaniel! What... why... FUCK me, I thought you were Beth!" He now looked as stunned as I was.

"Umm, I... ugh... I'm sorry.. I... didn't know you'd be h-home..." He let go of me, and stepped back a bit.

"I wouldn't have been, but the sprinklers went off at the office, and everything is shut down. But... This... I mean, I guess I wondered if you might be gay, but..."

"Gay? N-no... no. I'm NOT. I... just like... dressing like Mom, looking like her. I um... liked the idea of guys looking at me like they looked at her, and, everyone said I looked like her, so..." Swallowing, trying to get the lump out of my throat.

His voiced dropped some, and he nodded. "Well, you DO look like her. JUST like her, dressed like that. Damn, boy, I was so excited, seeing her... uh, you, It's... it's been a while since she looked like... THAT."

He shifted his weight, and that's when I saw the bulge in his pants. God, I had... excited him! He really DID think I was Mom. I pointed to it, and stammered, "I'm so sorry, I didn't mean to... cause that. I was... just having fun." I think we both blushed.

He said, "well, dammit, it's been a while since your Mom wanted to... do... anything. I guess nature took over." We each stood there, awkwardly, and it was clear, that thing wasn't going down. I don't know why, but I could not stop staring. I'd heard enough through the bedroom door to know it had to be impressive, Mom, before things cooled off, made enough noise. All I could think of was, I made that happen. For the first time, I wondered about cocks. What it would feel like, what... to DO with one. AND, could I do it. I can only guess, but when my eyes shifted to his face, it seemed like he might be wondering the same thing.

"Wh-what do you call yourself, when you... do this?" Waving his hands outwardly.

I turned red, and whispered, "Natalie. Nathaniel just didn't fit." He laughed, nodding.

"Natalie, could I... give you a hug? I could really use one, and you are SO pretty." I didn't answer, I just stepped into him, wrapping my arms around him. He is six foot three, so, even in my heels, he towered over me, just like he did Mom. His big arms wrapped around me, and I felt that hardon pressing against me. I SWEAR, I could feel it throbbing. My mind was racing. This is new territory. We barely moved, and I felt the heat from him. His big hands eased down my back, and ever so gently caressed my butt. I maybe SHOULD have pulled away, and been upset, but in that moment, I FELT like a girl. A girl who was desired. I loved that feeling. I'd never been THIS close to another being, and my brain screamed for more.

I looked up at him, and saw lust, yes, but more. He KNEW who I was, what I was, but, was attracted to me. He must have seen the surrender in my eyes, because he lowered his lips to mine. Ever so gently, I felt my first kiss. NOT a kiss I'd ever have imagined, but one that changed me forever. I opened my lips and his tongue danced on mine. It was THAT moment that I KNEW I'd give him everything. Our bodies slowly grinded on each other, and I felt myself moaning. He picked me up, carried me to the bed. He sat me on the bed, looked down at me and said. "If you don't want this, say so now, because, I won't be able to stop."

I reached out, rubbed that bulge, and unbuckled his pants. I wasn't sure what to do, but I had a feeling he was going to teach me.