Ginger's Makeup Ch. 02

Please remember this is a copyrighted work and all legal disclaimers apply. The story covers a history of changes that Charlie experienced with Ginger after that first night. MadQuill

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Three weeks later I was heading out to shop with Thelma at the nearby Mall. She had suggested that the day would be spent looking at and possibly buying some new shoes and accessories. I had a small amount of cash and was anxious.

"I've got a few friends who work at the stores. One woman works at the lingerie store we'll visit and Sheila is a manager at Aldos. She'll help us by applying her Employee Discount. Come on Charlie. You look too cute to stay in today."

I was anxious every time I ventured outside. She was wearing a pair of black leather pants that were so tight I could see the indent of her Venus mound and of course when she turned her ass cleft was well defined by the material tautly conforming to her body. The black heels were way too tall for me. She was so lovely.

"I can't believe the work it takes for you to get into those Thelma!" She was a yard away reviewing herself in front of the mirror.

"Charlie that print dress does look good on you. I explained that we're not in a troop so we simply can't be dressed alike. Besides I only have one pair of these pants. You're lucky that Ginger agreed to share the new girl in her life with me. The subtle changes to your makeup details make a huge difference. You don't pass like a boy now. You look like a 'doe' now." She kissed my cheek when I came beside her at the mirror.

"Come on, let's get going cutie," she said.

Her friends various discounts saved us both hundreds of dollars. She insisted on buying many small items for me and I came home to Ginger's with a bounty.

"I'm in the toilet girls. I'll be there is a minute. I want to see Charlie in the new pants and the five inch heels!"

The strapped heels were only four and a half inches and Thelma had pushed me to get a pair of faux leather leggings. Even with help I couldn't get the sexy pants on easily. Ginger came out wearing a loose jean and she was barefoot. Yet her face looked gorgeous. She came to me and bending at the waist kissed me.

"The pants are worth the effort Charlie. Just keep slipping and pulling. Wow Thelma, how did she afford that heel?"

"Charlie has slightly bigger feet as I do and I learned how to review the discount table long ago; thirty-two bucks."

"But my pair cost me over a one-fifty only two weeks ago?" Ginger went to her wardrobe and returned with a pair matching my new ones.

"Life isn't always fair Ging, help Charlie with the waist okay?"

The trip had included my ear piercing, "Those look cute in her ears. Was it painful?"

I smiled, "Not at all Ginger. How did the doctor appointment go?"

"She says I just need a different prescription. The new pills are ready at the drugstore. We'll stop on the way to work then?"

Thelma said as I moved to the mirror, "Great fit Charlie."

Ginger stood and pulled Thelma beside me, "Look how beautiful my two lovers are! Two tightly wrapped bums," as she shifted us about laughing.

Thelma teased, "Let's get into bed then girls," but Ginger was in charge now.

"No way can I get sexy for you two. I'm on at five this evening and Charlie has a shift too."

I had quit the Inn following my revelation at Ginger's hand. After tens days and my cash getting thin she suggested I could try her old position at a medium priced restaurant down the street. It was more casual but our schedules seemed to coincide making it possible for me to avoid driving while not being dressed as a boy. I didn't need a cop causing a problem. The Place on the Park was a great little bistro with a popular bar as well. Being a hostess and bar server brought in more than twice what I had getting at the Inn. At the time Ginger suggested, "You can use many of my outfits from my stint there. No one will notice."

The only problem was Ginger had left because of bothersome attention from one of the staff. He wasn't a head of the place but was second in-charge.

"If he even comes near you Charlie let me know. I'll call his boss and he'll be spinning. Two reports of harassment would get him fired."

The idea that Sam would make a pass was ludicrous. I didn't have Ginger's charms! Besides Thelma had suggested I use a pair of glasses to help conceal my facial structure.

"She looks very good but watch what happens when I put these on Charlie."

She was correct. The affect of the subtle shadow on my face meant that the other details of my face and head were less clear. The lenses were just clear glass.

"I've used this device to reduce the number of passes made on me at one of the bars I used to work. Girls wearing glasses you know," Thelma said.

That evening I got off early at ten though and was walking toward the Inn to meet Ginger. It was only a quarter of a mile and I'd worn a low wedge shoe tonight. A car slowed alongside the walk but I didn't pay any attention nor look to see whom it was. The girls had trained me to ignore obvious attention from leches.

"Do you need a ride home Charlie?" It was Sam in his little bimmer. The window on the passenger side was down and I spoke as I continued to walk toward the Inn.

I considered my alternatives, "No I'm find and the friend I'm meeting is just up the street."

He didn't drive off but said, "Could that be Ginger? She works at the Inn."

Now I was stuck. She had advised me to minimize the people who knew I was her friend. At least until now I hadn't had to share the information with anyone at the Place on the Park.

I came up with a response quickly. "Sam I'm with someone and therefore though it's nice that you're interested in me I can't say the same. Please respect my privacy and I'll respect yours okay?"

This seemed to work, "Sure thing Babe. I'll just move along." He sped away and I didn't think anymore about the incident. I also didn't mention it to Ginger nor Thelma.

- - - - - -

My education had been Ginger's joy since that first evening and I had come to realize that she was a better judge of all things regarding Charlie than I could be. Therefore the omission of the conversation with Sam was crazy. Why was I now thinking of superseding her control and vision?

- - - - - -

After Ginger had dress me that first time we had slept together. She insisted that I needed to be taught to pleasure her body. I didn't orgasm with her for nearly a week.

"If you get my pleasure correct yours will be a lot more intense Charlie. Playing like girls do will take some time and I'm willing to teach you. So first and always keep your tongue soft and your fingers moist. Lick me gently until its obvious I'm coming."

By the third night of dressing and loving her I was able to get her to peak without her intervening. She loved to lick my face clean after her orgasms! The needs of my lover became more important each of those first days. I say days because we didn't get out of bed the fourth day until after she had come three times. Her toys were so varied that I almost considered writing notes.

"This one is an insertable but we won't play with it for several weeks. Here, I want this long thin pink one buried in my ass."

This was prefaced by her instruction on keeping clean, "Your tongue will appreciate my clean little hole. I expect the same from my lover."

As I moved close to moisten her bottom I asked, "Your cleft has no hair. Can you shave me like this?" The toy slipped into her tight canal and I helped bring her to orgasm again.

Later she told me, "Women who enjoy sex eventually find they can enjoy anal. It can't be rushed Charlie and having a clean back door is essential. I love your tongue in my bottom and I want you to enjoy mine there in yours."

- - - - - - -

The actual shaving was very intimate, "Someday I will be deep inside you Charlie."

Ginger insisted that first week I spend watching her going everything, "Maybe you'll better understand how a woman lives by observing the routines we take for granted. It will be fun too Charlie, playing a 'shadow' like from the play "Peter Pan"."

We spoke of the gender shift that was at the core of that character.

Ginger wondered about the author Barrie's sexuality and the transformation at the core of the story. "I'll never grow up? That's what I mean. Peter will control his 'changes'. It's obvious to me why they used females in the roles over the years."

I wasn't so sure having been in a Lit class two years earlier with a professor who'd written her dissertation on the play. "I believe the casting was due to the labor laws back near the turn of the century in London."

"Don't get technical Charlie. It's just a great story. I'm just suggesting that you can use the shadow idea to help make these changes a little easier." She came to me and we hugged.

"So I mimic you, doing the dishes, brushing your beautiful long hair, putting on your bra?"

She smirked and said, "I've got to pee. You come and watch. You'll learn something I'm sure."

I did and I listened as she released the urine. "It's so quiet compared to my habit."

"And a lot less messy. I love cock as much as any girl but those damn things have made a mess out of the world."

- - - - - - -

Near the end of the first week with Ginger I was in the second bedroom using the desktop CPU when I hear voices. It was Thelma at the door.

"So where are you hiding him, oh, I should've said 'her' correct?"

I stepped into the front room wearing a simple dress and flats but with full makeup and a wig. "Hello Thelma."

She saw me immediately and ran across the wood floor, her heels clicking. "Aren't you adorable Charlie! Ginger said it was remarkable, I mean you face and body were meant for this change." She hugged me with her face turned to avoid affecting her own makeup.

"I'm on in twenty minutes sweetie. Ginger offered to let me see her new girlfriend. You look great, even nice boobs?" She looked toward Ginger.

"I found them on-line over a week ago," Ginger quietly provided.

I paused hearing this since it implied that she had bought the silicone falsies before the night I first stayed. I had wondered during the past five days how easily she had coopted me. The dresses and wigs were hers but our feet weren't close in size. Yet she had three pairs of heels that seemed to fit well. Now I was clear. She had set up that evening and initiated my girlhood.

Thelma smiled and turned toward the door, "I'll be late if I get into the details now. Let's meet after work for a drink girls, here will be okay Ginger?"

Ginger closed the door and walked over to where I stood, "Yes Charlie, I lead you to this. I didn't trick you. I knew you were meant for a different path. You are already a beauty and with a bit more training from Thelma and me you'll be perfect."

I wondered if there was something inside my mind that would have found this alternative life independently.

"Why did you select me Ginger? I can accept the notion that I'm a 'prettyboy'. There have been girls telling me that all of my life. Shit there have been guys implying that since my junior year when I didn't have to shave or what. How did you come to decide to make your life more complicated?" She was quiet, just listening.

I turned away but encountered my image in the hall mirror, "I don't know Ginger. I do love being with you. Is this just a short-term masquerade though? I enjoy how smooth my body is and I clearing like wearing your clothes and sleeping with you but someone will find out. I can't fool everyone."

She came to my side and I noticed her dress and cleavage. About her long neck she had a simple gold necklace. She smiled as my eyes reviewed her tightly fit black dress. "I saw this 'girl' the first time I met you. I didn't scheme to get you in my dressing room. But I did buy the appliances that make your body womanly Charlie. I wanted you in my bed, and your gender isn't an issue. I've slept with many more girls than men and I think I've got a right to choose. I'll be sad if you leave now. Selfish as I may sound I'm just getting started with my new girlfriend and won't let go easily."

Her eyes were nearly at my level since she was wearing a tall pair of black pumps and she turned me and kissed me. Her soft tongue entered my mouth as her hand caressed my bottom. She reached into my thong panty and slipped the narrow panel material aside. Holding her fingertip at the pucker opening she said, "This is my next step. To have you filled up and screaming to climax. You haven't had an orgasm with me yet Charlie. Well, I haven't allowed a cock in my pussy for nearly a year either."

This thought caused me anxiety. She was really not into my penis?

"What about the toys, don't they count?" I asked as she moved about but didn't answer my question.

Ginger hugged me and our breasts touched. She dropped to her knees, "Let's see if my girl has a need for release."

As she lifted my dress I looked down to her face. Her eyes were smiling as her left hand shifted the thong that held my penis back and though soft was now near her mouth. With her right hand she touched it lightly as she moved close enough to kiss and lick the very tip.

I moaned softly and she said, "Just like a girl. This soft clit is for me."

She rolled her tongue across the head of my stiffing member and then ran up its length to my groin. Slowly she moved back to the head and lightly licked as I became fully erect. With her right hand at the base she licked slowly across the head again and again then slipped her moist tongue down to my testes as the finger again teased my opening. She seemed to relish the fact that I was stiff as her tongue moved slowly about the length and along the sides repeatedly. I trembled waiting to be engulfed in her warm mouth.

"A girl loves her pussy licked this way Charlie; slowly and with passion. Enjoy this because it is your future. I want you to love my sweet holes like I'm loving your clit."

As she said this her mouth and tongue engulf me. Covering my hard penis her lips reached nearly my groin. Then I realized how I was dress and her lesson made sense. I needed to love her body in the same way. I would learn to be slow and focus on her feelings and needs. It was a marvel how she slipped my clit past her throat and held me there. She had definitely done this before. But now I was the lucky one, the lucky girl. That's when I decided I was this girl Charlie and would remain so. I continued to watch her lovely me. She paused slightly and ran her tongue along the length then allowed my body to re-enter hers deeply. Her eyes looked up to mine and said, 'I'm loving this'.

I almost lost it thinking of her sensual kiss but she softly said, "I love juice Charlie. Fill my mouth with your honey."

I hadn't ever released into a lovers mouth but I couldn't stop and I came strongly. I almost lost balance but she kept her mouth on my clit and held my bottom. "That's a girl, sweet honey in my mouth."

Standing Ginger kissed me, "We will share this too Charlie."

To be continued,

MadQuill