A Helping Hand

"Not bad for your first time. You have a week to practice and I expect you to be a pro at this. Now come over here and I'll help you with the rest of it."

I stood back up and noticed how the breeze from my slight motion felt against my stocking covered legs. The soft breeze felt incredible against my smooth skin and caused penis to stick straight out.

Looking down at my cock my mother said "Now, that is going to be a problem."

She fished around in her bags again and pulled out something small and walked over to me. Again, she crouched down in front of me and pulled a pair of black satin panties up my legs. When she reached my waist she took my penis in her hand and did her best to stuff it into the panties. Between the silky material of the panties against my skin and her hands on my cock it was enough to make me explode right into the panties. I thought that she would be mad, but I felt her hand slowly stroke the length of my cock while my cock filled the panties with cum.

Looking up at me she asked in a gentle tone "Does that feel better honey?"

I was so embarrassed all I could do was nod. I watched as my mother wiped up my cum with her hand and licked it off of her fingers. My mouth dropped at the sight and she stood back up.

"You look surprised, it's just cum. Don't tell me you've never tasted your cum before."

Still at a loss for words I shook my head.

"I thought teenage boys did all sorts of things like that. Here." My mother reached down and pushed her hand into my panties, wiping up more of my cum, and brought her hand to my mouth. My mouth still hung open in shock as her outstretched finger slowly brushed against my lower lip as it pushed further into my mouth. Instinctively I closed my lips around my mother's finger and licked my cum off of her. The taste is hard to describe but it was very salty with a heavy musky flavor. It didn't taste bad, but it didn't taste like anything I had ever had before.

She pulled her finger from my mouth and asked "Well?"

"ummm..."

"That wasn't so bad was it?"

"I guess not."

"It's a good thing I bought you other panties, but don't go doing that in every pair of panties you have. This is why you need to practice before the party. You need to look and feel like a natural girl if you are going to pull it off."

"I understand. I'll do anything you say mom."

"Now take off those dirty panties and put on a fresh pair."

I hooked my thumbs into the waistband of the panties and slid them down my legs. I picked them up off the floor and curiously looked at the crotch of panties that was still covered in my cum.

"It's ok honey, I won't tell anyone if you want to take another taste."

I can't say that I liked the taste of my cum at first, but I was intrigued. I pulled the panties to my mouth and licked the silky fabric until my tongue was covered in my sticky cum. For some reason the taste was exciting to me. I might have been partly because my gorgeous half naked mother was goading me to eat it but I slowly started to enjoy the taste as it lingered on my lips. My mother handed me another pair of panties and I pulled them up my legs. Once again, she pushed her hand into the front of my panties and grabbed my cock. This time she pushed my penis against my body and between my legs. She was somewhat forceful, but not enough to hurt.

"See, you need to tuck it between your legs otherwise you won't really look like a girl. You have a lot to practice young woman..."

My mother took my hand and pressed it against the crotch of her panties. She held it there for a few moments before gently rubbing my hand across the thin silky fabric that covered her pussy. I could feel the heat of her body through the material and thought that I heard a soft moan escape her lips at the intimate contact.

"This is how it should feel. Isn't that nice?"

"Yes, you feel very soft."

She let go of my hand but I lingered pushing it against her body a little more firmly before she broke the silence.

"It feels so soft because I shave every day. See."

She pushed the waistband of her panties down exposing her bare pussy. I had never seen a pussy before and was mesmerized by the gentle slope of her mound and the small nub of skin protruding above her slit. She must have noticed me staring and again pushed my hand against her crotch. This time I could feel the contours of her soft skin against me. I couldn't believe how soft she was. I took my time gently caressing my mother's pussy and noticed that she moved her legs apart ever so slightly to allow me better access. While rubbing her I felt my fingers getting moist and realized that she must be getting wet. I was thrilled that my hand was getting her so excited. I pushed my luck and pressed my finger against her slit and felt it slide between the moist folds of her pussy. My mother gasped as my finger brushed against the entrance to her pussy and she abruptly took a half step back. I could hear her panting heavily as I watched her chest rising and falling with each breath. I turned my attention to my hand, my finger was covered in her juices. I brought my hand up to my face and inhaled her aroma before licking my finger. My mother stood frozen with her panties stretched across her hips watching me lick her pussy juices off of my finger. Her juices tasted very different from mine. Hers was much sweeter and almost floral. I was intrigued by my taste, but I was immediately hooked on hers.

"mmmm..." I smiled at her as I moaned in satisfaction.

Seeming somewhat embarrassed she pulled up her panties and then stepped back towards me and showed me how to clip the garter straps to the tops of the stockings and then pulled out a pair of high heels.

"This is going to be the trickiest part for you. Some women take years to be comfortable in heels, so you will need to wear these at all times around the house."

I slipped my feet into the heels and they were a perfect fit. My mother held me by my arm to help me balance as I took my first tentative steps. I was surprised how difficult it was to walk in them. Women make it look so easy. I was determined to get the hang of it so I slowly walked around my room. I gained confidence with every step and eventually my mother let go of my arm.

"Very good. With practice you will be a natural I can tell."

Next, my mother pulled out a wig and spent a few minutes adjusting it and securing it to my hair with bobby pins. My new straight hair was dark brown and fell down between my shoulder blades. It felt weird having so much hair and I gave my head a few twists causing it to swoosh around me. But I didn't have much time to enjoy my new hair when my mom spoke up again.

"Now for the finishing touch. Let's go up to my room and do your makeup. It's very important that you pay attention for this part because you will need to be able to do your makeup all on your own."

My mother picked up her dress and pulled it over her head. With a quick tie of the strap her body was once again covered. She led me from my room to hers slowly as I struggled in the heels. She sat me down at her vanity and over the course of the next hour I got my first lesson in makeup. She plucked my eyebrows into a thin tapered line and showed me how to curl my eye lashes. She taught me about foundation and blush. When she was finished I was astonished that I looked like a real girl. My mother gave me a little color in my cheeks with a light blush. My blue eyes were accented by a soft layer of eye shadow that faded into my skin tone and my lips looked more pronounced with a pale pink color that gently shimmered under the lights of her vanity.

I walked over to her body length mirror and admired her work. I twisted and turned to see myself from every angle and was amazed at my transformation. The heels gave my legs a much more feminine shape. The corset was already forcing my body into more of an hourglass shape and combined with my new breasts made me look like a knockout.

"Pretty good, huh?"

"Wow mom, this is incredible. I don't even recognize myself."

"That's the point. Now all you have to do is practice walking around dressed like a girl and learn how to do you our makeup."

"We just might pull this off after all." I said with a smile as I ogled myself in the mirror.

"I don't know how I missed it, but you need to work on your voice too!"

"You're right." Thankfully, I've always been good with voices. I cleared my throat and said "How does sound?"

"Hmmm... Good, but not great. I think you should spend as much time as you can this week practicing your voice too."

"Ok, I'll get it."

"Since this is only for the next week I thought it would be silly to buy you dresses when you can just borrow mine. We are about the same size after all. Why don't you grab something from my closet we have somewhere to go."

"You want me to go out like this?"

"Of course! You need to practice and we have things to do, now hurry up and pick something out."

My mother had a massive walk-in closet that was the size of a small apartment. I was overwhelmed when I walked in the first time. I felt foolish that I never thought to borrow some of her silky lingerie before. This was the mother lode. She had two full racks filled with silk nighties and negligees. Some of them were full length gowns while others were much shorter. I reached out and brushed my hand across the wall of soft fabric. I could already feel my cock stirring in my panties as I looked through my mother's lingerie. Next to the racks of lingerie were a stack of drawers. One of them was partially open and I saw that it was filled with her panties. Nervously I pulled it open further and let my hand explore the soft pile of underwear rolling the fabric between my fingers. I heard footsteps behind me and quickly pushed the drawer closed.

"Come on, we don't have all day. You can go shopping later."

She walked over to a rack that was filled with dresses and pulled one out.

"Try this on."

She handed me a light summer dress in a floral print. It fit perfectly and the shoulder straps covered the straps of the corset. In an instant I was transformed from a lingerie-clad vixen to the girl next door.

"What a good fit! It's like we're sisters!" My mom shouted with a devilish smile.

I followed her down to the car and managed to avoid killing myself in the heels. I was very cautious with the stairs at first but slowly my balance was improving which allowed me to keep up with my mom as we walked through the house. We drove into town and got a quick lunch before going to a tanning salon. My mom made arrangements for me to get a weekly package telling the woman at the counter that she wanted me to be as dark as possible. She waited for me in the front of the store while I was led to a room in the back. I was given a little mesh hat to put my hair in and carefully undressed myself. I found a zipper hidden in the seam on the side of the corset and felt a wave of relief when I took it off. I stripped down to my panties and got into the tanning bed. After my time was up I looked myself over in the mirror and noticed a hint of color already. I took my time getting ready, trying to remember how to put everything on. I met my mother in the front room where she complimented me on my new color.

We went out for an early dinner at a cafe and I continued practicing my new voice. It was hard for me to remember to always use my feminine voice but after an hour or two it was coming more naturally. After eating, we went to a salon and got our nails done. My mother chose a deep red for herself and a soft pink tone for me. In addition to getting our nails done she asked them to pierce my ears. I was left with two small gold studs and was told not to take them out for two weeks. After all of the pampering we went back home. It was getting late and my father would be getting home soon so my mother took me up to her room. She led me back to her vanity and showed me how to remove my makeup before telling me to pick out a night gown from her closet. After ten minutes alone cataloguing her entire wardrobe of lingerie she joined me and began getting ready for bed herself. My mom tugged on the strap of her dress and let it fall to the floor. She spent a minute walking around her closet in her panties putting away her dress and jewelry. I was torn between watching my nearly naked mother gracefully float around the room with her breasts swaying at every move and focusing my attention on her endless collection of sexy underwear. I was in heaven. My mother walked over to the rack in front of me and slipped her panties off. She pulled out a shiny black chemise with a lace trim. I watched intently as she lifted it above her head arching her back and pushing her breasts out towards me. My eyes drifted down to her bald pussy tucked neatly between her legs as the silky material fell into place ending just beyond her crotch with a small slit up on side of the front exposing her leg up to her waist. She looked like a goddess and I felt honored to be under her guidance.

"You look like you're having a hard time deciding."

She flipped through the hangars on the rack and pulled out a little outfit for me. The outfit she picked for me was a two piece. The top was a short silky shirt that tied up in the back and left my midriff exposed. The bottom was a pair of high cut silky boy shorts that barely covered my ass. The outfit was black with little red and white hearts all over them. She helped me out of my clothes and into her lingerie. Watching my mother move around in her chemise and feeling the silky material against my skin made me rock hard again and the boy shorts that I wore did nothing to constrain my cock. The head of my penis proudly projected out of one the leg openings and pushed the silky material away from my body. Taking my penis in her hand she said.

"Remember you need to keep this tucked between your legs at all times. I don't care how excited you get you must always play the part."

It didn't help my situation that my mother was slowly stroking my cock as she scolded me.

"I'm starting to think that you like playing dress up. Is that right?"

I nodded weakly.

"Well, since you've been such a good girl today."

I watched in disbelief as my mother knelt down and began stroking me faster. My eyes followed her down and she looked up at me with a wicked smile before she guided the tip of my cock towards her mouth. My body reeled as her warm wet lips first made contact with the tip of my cock. She kissed it and then opened her mouth wrapping her lips around my penis as she slowly pushed her head forward into my body. The warmth of her mouth encasing my cock was too much for me to handle and I grunted as my cock twitched releasing my cum into her mouth. She kept her mouth on my cock until I finished cumming and then stood back up. I watched as she swallowed my cum and then leaned in to me pressing her lips against mine. She tasted sweet like honey but I could also taste my own musky cum on her lips. After a brief kiss she pulled back and told me to go to bed. I gathered up my clothes and headed back to my room. As I walked through the bedroom I heard her call back to me.

"Don't forget these" She stood in the doorway to her closet with her arm outstretched and the panties she had been wearing earlier dangling from her finger.

Still wearing my heels I walked back to her as quickly as I could and took the panties from her. I felt her staring at me as I left her room. Back in my bedroom I dropped my clothes on the floor and held her panties up to my face inhaling her aroma again. My head spun as I pressed the soft material to my face. I kicked off the heels and slipped into bed where I fell asleep with the crotch of my mother's panties pressed against my face.

The next day I was awoken by my mother standing over my bed. The smile on my mother's face reminded me that I still had her panties pressed against my nose. I snatched them away and tucked them under the covers, but it was too late and I felt my face redden.

"Rise and shine honey." My mother's voice was soft and chipper.

I pulled the blanket off of me and sat on the edge of my bed. I saw that my mother has already layed out an outfit for me to wear. There was a fresh pair of black panties, the same corset and stockings, and a pink polka dot dress. She told me to get dressed and then watched as I applied my makeup. She gave me tips along the way and then told me that I was on my own today because she had more errands to run for the party. She reminded me to go to the tanning salon and gave me a short grocery list. Before she left she again tightened my corset until I felt like it was almost too tight. I looked in the mirror and marveled at how my figure was even more feminine than the day before.

After she left I decided to spend the morning out in the sun by the pool. Since I was instructed to leave the corset on all day I only took off my dress and napped in a lounge chair for most of the morning. I made my tanning session and stopped by the grocery store, all the while practicing my new voice. By the end of the day I found that I could easily speak like a girl without even thinking about it. When I got home the day was almost gone but my parents were still out so I went up to their room and went through my mom's makeup in her vanity. I sampled her different perfumes until I found one that I liked and sprayed it on my neck. The feminine scent gave me goosebumps as I admired myself in the mirror. I was experimenting with different colors of lipstick when I heard her come in. She seemed to revel in the fact that I was taking my role so seriously. She told me that my father was taking her out for the night and she needed to get ready. She started to take off her clothes while asking me about my day. I watched as she stripped off her clothes and darted around the room naked. She emerged from her closet wearing a bra and matching panties and shooed me away from her vanity so that she could do her makeup and told me to pick out another nightie to wear. I was again lost in her vast collection and was once again drawn to her panty drawer. I opened a different drawer this time and carefully examined every piece of underwear she had. When I reached the bottom of the drawer my hand hit something hard and I pulled it out curiously.

I had found my mother's vibrator. It never occurred to me that she would have a sex toy, but my cock instantly sprang to attention. I licked the end of it and found that it tasted just like her juices did the day before. I heard her walk into the closet and turned around trying to hide her vibrator behind my back. She knew what I had in my hand and walked right up to me pulling it from my hand.

"So, you found my little friend. Boy's aren't the only ones who play with themselves you know. I haven't played with this in a long time." Her voice trailed off as she said that.

My mother walked over to the plush chair in the corner of her closet and sat down with her legs spread wide apart. She pushed the front of her panties to the side and I heard a sharp inhale as she pushed the tip of her vibrator against her pussy. She rubbed it up and down the length of her pussy before twisting the end of it. I watched as she plunged her toy deep into her wet pussy. I walked over to her to get a closer look and could hear the sound of the suction caused by her fucking herself. Suddenly she pulled it out and turned it off.

"There's no time for this now. I'm already running late." She handed me her vibrator and said "Put this back where you found it and pick out any nightie you want. You should take these too." She stepped out of her panties and handed them to me too. My mother grabbed a slinky red cocktail dress and pulled it over her head. She took a pair of red high heels and left for dinner without putting on another pair of panties. My heart was pounding as I held her vibrator in one hand and her dripping wet panties in my other. I took off my dress and slipped out of my panties, replacing them with her wet ones. I tucked my cock into the moist fabric and rubbed myself while I licked my mother's juices off of her vibrator. I came right away filling her panties with my cum. I was so worked up that I sat down in her chair until I calmed down. I took off her panties carefully making sure not to spill any of my cum on her floor. I watched myself in her mirror dressed in my black and pink corset as I lapped up the mixture of my cum and her juices from her panties. I was amazed at how hot I looked in my new costume and was getting turned on watching myself. After I cleaned up her panties I picked out a sheer green chemise with matching panties and carefully removed my makeup before retiring to my room. I again fell asleep with her panties pressed against my face.