Can I Try? Pt. 03

"OK" my Mom said at last, spinning my chair to look in the mirror "what do you think?"

I was stunned. The reflection in the mirror was one I had only dreamed of. Looking back at me was a pretty young girl in an over sized t-shirt. She was so beautiful I was speechless. While I looked I saw the girl's eyes go glassy and start to well up with tears.

"None of that!" my Mom said smiling as she held my eyes open and blew on them to evaporate the tears before they ruined my eye makeup. Before long we were laughing and hugging and the urge to cry passed.

"You're gorgeous Baby." My Mom complimented.

"I wonder what Randy will think." I mused.

"Oh I think he'll like it," my mom replied with a knowing smile, "he probably won't be able to keep his hands off of you."

I blushed bright red at this kind of talk from my Mom.

"Have you heard from Randy at all?" Mom asked.

"No" I said feeling a bit rejected "I think he's avoiding me."

"OK you silly girl, let's put some clothes on you and order some pizza." My Mom said changing the subject before the happy mood soured.

I stood and my Mom lifted my t-shirt over my head, leaving me in nothing but panties. She grabbed the Victoria secret bag and reached in. The first item she brought out was a bra, simple and black. It had very small cups and was made for someone nearly as flat as I was.

She helped me put it on, the material was comfortable and the straps made my shoulders look really sexy. I felt like a girl wearing it. It had a liner that pushed the skin on my chest inward enhancing the illusion of cleavage my mom had done with the makeup.

"OK now step two." My Mom declared as she pulled a beautiful lacey purple and black bra out of the bag. This one had formed cups that were bigger. Not huge but definitely meant for a modest breast size, like a B cup.

This went over the smaller bra and to my surprise the cups met flesh in what appeared to be a decent sized pair of tits, the illusion was incredible!

"Hmm, yes that will suffice until we get you some real boobs." She said with a wink.

My Mom handed me a pair of lacey panties that matched the bra and turned her back as I changed from the ones I had on.

Looking in the mirror at my slender and feminized body, my Mom was right. I wanted real boobs more than anything in the world. I wanted to be this girl I saw more than anything in the world.

"You look so beautiful Honey." My Mom said standing behind me and looking over my shoulder in the mirror.

"We do need to figure out what to do with this." She said reaching around the front of me and tapping the small bulge in my panties. It wasn't hard at the moment, but she slid her hand into my waistband and cupped it in her hand I became nearly instantly aroused.

"Spread your legs a little." She whispered in my ear.

I did, but moaned a bit as her soft hand started pushing my little package between my legs. She massaged as she pushed farther and farther between my legs. I was fully hard as she painfully tucked me and my ass involuntarily pushing back against her. She held my hip with her other hand.

"Shh, shh," she cooed, her hand rubbing and pushing as I moaned sensually in her arms "now legs together."

I was left with an intensely sexual feeling between my legs as my Mom's hand slid away. My smooth, shaved inner thighs held my hard cock in place painfully but the memory of my Mom touching me so sensually lingered.

"Whew," she said, fanning her face "that was kind of intense."

"Yeah." I acknowledged embarrassed.

"OK slip into these." She said changing the subject and handing me a pair of dark pantyhose.

I put them on, then she handed me a black pleated skirt. I slid into that too. Then she gave me a thin cotton camisole, low cut and burgundy red. It was very form fitting and really lifted my breasts even more. I looked in the mirror again.

"Holy shit" I said, my voice cracking a bit. I looked incredible.

"Don't get too excited," Mom warned, "we're not done yet. No outfit is complete without accessories."

She gave me some silver bangles for my wrists and some dangly silver earrings. My ears were already pierced so I removed the simple stainless steel studs I usually wore and replaced them with the more feminine jewelry. We topped off the look with a simple silver necklace with a nice silver pendant.

"OK now shoes." My Mom said producing a pair of high heeled Mary Janes with a wide heel. I put them on and my new look was complete.

"Wow Honey you look so amazing!" she said hugging me tightly. "OK picture time!"

We took a few pictures in different poses. My Mom totally hammed it up acting like a high fashion photographer.

"Show me your pouty face, there you go. Now give me a big smile, work it girl." It was hilarious.

Then the doorbell rang.

"Yay! The Pizza is here!" my Mom exclaimed. Then she got a wicked grin on her face. Handing me her purse, which did go well with my outfit, she said "Why don't you go get it?"

"Mom, I can't!" I was horrified.

"Oh relax, he'll never know and you look amazing."

"OK" I said giving in.

I was super distracted and almost killed myself trying to walk in the high heels. I kicked them off and tried to walk in a feminine way down the stairs and to the door. I stood in front of the door my heart pound. I opened it.

There he was, a kind of fat guy in his thirties holding a pizza. He gave me a once over that had me flushing immediately. I dug in the purse for money to pay him, then took the pizza. He gave me another leering look before he left, leaving me flushed and breathless.

It was a really quick interaction and to be entirely honest he was kind of gross, but I learned a lot about myself in those few seconds. First, he was entirely fooled in that he thought I was a girl. This gave me a confidence that I didn't have before. The second was that my body responded to his desire, the way he looked at me made my little cock harden painfully trapped between my thighs despite my not being attracted to him at all.

I brought the pizza to the kitchen table lost in thought. Mom and I ate pizza, drank some wine and talked. She helped me work on my body language, posture and mannerisms. I was becoming more feminine by the minute, but I also realized as we practiced that I had a lifetime of indoctrination to both unlearn (typically male mannerisms) and then learn to truly become the young lady I wanted to be. It is difficult to realize how different we are until you try to become the other.

After we ate we worked on walking in high heels. My Mom had gotten me three pairs to start me off. The Mary Janes had a thick heel and were much easier to walk in than the pumps or strappy stilettos, but I loved the way the high stilettos made me look so I worked hard at getting used to them.

It was getting late. Mom and I had probably just a touch too much wine and we were both tired and a bit silly. Mom led me back upstairs to her bedroom. She had me sit at her vanity and she instructed me in removing my makeup.

"Do I have to?" I asked. I didn't want to take it off because I just looked so pretty.

"Yes Sweetie, a girl needs to take care of her skin, sleeping in makeup will having you breaking out in no time."

Using cotton pads and makeup remover she cleaned my face and chest. She let my hair down too. To my surprise I really didn't look that bad even without make up.

"OK strip." My Mom demanded again.

I stripped down to my panties and bra while she fished around in the Victoria's Secret bag and pulled out a really pretty green and black satin and lace babydoll nighty.

"Bra too Honey." I pouted but did as she asked. To my great surprise my Mom started disrobing too. My little cock got instantly hard between my thighs when she took off her bra. Her breasts were big round globes with only the slightest sag and with very large nipples that got hard in the cool room air. My Mom stood before me, her much curvier body on display in just panties, a black lace pair of boy short style cut. My mouth watered. I swallowed hard.

"Just us girls now, right Sweetheart?" Girl or not my body definitely responded to hers.

She grabbed a different babydoll from the bag and slipped it over her head. I did the same, mine was made for a small breasted woman so it fit me nearly perfectly.

"Time for bed." She said. I moved to head to my room, fully intent on masturbating like crazy. I had been turned on so many times that day with no relief.

As I went to leave my Mom grabbed my hand. "Would you stay?" she asked earnestly, "I haven't had a girls night since college and this is just so fun."

Looking into her hazel eyes so enthusiastic I could refuse her even though it would mean a frustrating night.

We hit the lights and lay down in her king sized bed facing each other in the moonlit darkness. We gossiped for a while. She asked me about Randy and my feelings for him. I asked her about Paul and why she never dated much. We talked and giggled together for over an hour.

We touched each other a lot as we spoke. I would brush a strand of hair out of her face, or our hands or legs would touch. Each contact sent a forbidden electric thrill all through my body. I didn't think there would be any way I would get to sleep that night.

In the darkness I had freed my cock from between my thighs. I liked looking flat in front, but tucking was so uncomfortable, particularly when I was getting turned on every few minutes.

Then my Mom ran a long fingernail over my belly.

"So flat," she commented, "guys will like that."

I couldn't speak as her fingernail continued over my hard cock barely contained within my panties.

"I guess something got out." She said as she traced the outline. It was heave but also excruciating.

"It's OK though." She mused as her fingers spread to massage the head causing me to moan.

"Does that feel good?" she asked.

"Yes Mom"

"Have you ever been with a woman before?"

"No"

"We can't take this too far Sweetie, but if you want to be a woman you should understand what that feels like."

She took my hand and guided it to her belly then into the top of her panties. I slid my fingers gingerly over her smooth, shaved mound. I started to press and probe, looking for the opening. Despite my liberal education I didn't really have a great understanding of female anatomy.

"Be soft, just explore." I stopped probing and felt the shape of her outer labia with a light touch. Not sure what to do I just very gently massaged using my fingertips.

"Mmm better." My Mom responded with a sigh.

"OK" I said as felt her hand slip into my panties and over my cock and balls and lightly massage me. I moved closer and our smooth legs entwined and rubbed against each other, smooth skin on smooth skin.

Then my fingertip found her slit and pressing just a bit she opened. It was so warm and very wet.

"Mmmm yesss" she moaned, pressing my cock just a bit more "do you feel how wet I am."

"Yes"

"That means you are making me feel good, let's make you wet too." She said as she got a little bottle and poured some in her hand before sliding back in my panties to rub my cock and balls.

In the darkness we lay caressing each other and moaning. My Mom would name the parts of her anatomy as I touched them, educating me as I explored her. Soon I had a feel for the landscape and she could guide me with a whispered word.

"Now back up to my clit," she moaned her back arching "yes, do you feel how hard it is? Yes rub it there, just the tip, mmm Oh god, just a bit faster..."

She also responded by stroking my cock in my panties faster and gripping it harder. I was enjoying the sensations, but holding back my orgasm was getting difficult.

"Faster Baby, rub me faster, oh god yes!" she cried out, her hand jerking me hard and fast as I tried to follow her instructions.

"Yes, there, there, there, oh god yes, so close!" she cried, then "I'm gonna cum, oh god make Mommy cum!"

I rubbed her clit as fast as I could while just trying to graze the tip.

"FUCK YES!!" she cried out lifting her hips hard, her back arching, hand still pumping my cock. It was too much watching her cum and I felt my cock explode in her hand. I was moaning wildly and just as out of control as her as my cum shot all over her hand, wrist and my tummy.

"Mmm Honey, that was amazing." My Mom said as our bodies calmed and cooled in the night air. She giggled a little as she let go of my cock. Her hand and wrist were soaked in my cum, she brought it up to my lips and I licked her fingers eagerly. Then she licked a bit herself.

Then she grabbed my wrist and brought the hand that had pleased her up to her own lips. My fingers were soaked in her juices. She licked them then guided my hand to my lips and I tasted her, it was glorious.

Then my Mom kissed me. We kissed like lovers, tongues entwined for a minute. Then she lay back with a big heavy sigh.

"I needed that." She said.

Soon we were asleep. It was a huge day for me, for both of us. I also realized I was wrong, sleeping in my Mom's bed was not frustrating at all.