4 comments/ 16430 views/ 13 favorites Ginger's Makeup Ch. 01 By: MadQuill She was tall in her stilettos and the ankle was the only part of her legs I could see when the manger Mr. Thom introduced me around that late summer afternoon three months ago. After the first hour of watching her parade about delivering the guest's their cocktails I saw more of her leg since the sheath gown of sequins in soft red was split along the left, biased to expose Ginger's thigh well passed the knee. Her smile cause me to dream of her over the next few evenings as I pedaled homeward. Ginger was only six years older than me but she was a centerfold alive in my small world. Work when she was at the Inn wasn't work. It was lust as I would track her, waiting for a glimpse of her moving and the flesh above her knee. After a few weeks of working together my fantasies were cooled as we'd spent the late evenings talking as we re-ordered the dining room for the next day's activities. She spoke of her boyfriend and her girlfriends but not her family. My imagination moved elsewhere since I'd come to know her as a person rather than a moving sex object. During my fourth week at the Inn she introduced another hostess. A woman named Thelma. To the staff she wasn't important but to me she was gracious and sexy. This friend of Ginger's captivated me. Thelma seemed drawn to me. I wasn't sure why but the friendship seem to develop quickly. She was a little older than Ginger and tall, especially with her high heels. Thelma wore her nearly black hair very short which was part of her charisma. It seemed unusual to me since all of the other women at the Inn and in my life wore their hair long. She was very attractive with beautiful eyes and high cheekbones but it was her scent that aroused me more than her beauty. Musky yet sweet would be how I'd describe it. I asked Ginger about Thelma's scent and she laughed, "Ambre Gris, it's not common. I know how you feel. It drives me crazy. She's so sexy, huh?" Her style was different than Ginger's but the two of them were fun to be with and for some reason I was to her as well. Sometime each evening Thelma would come up behind me and hold me, my butt snug against her mound, and she would cause me to stiffen. Her tease was welcome but private due to her sense of the activities away for us. No one ever saw her squeeze me, at least I thought so. Thelma had become my girl of lust. We were in the Kitchen before the crowds formed one Saturday and the girls were talking of their gowns when I stepped in. "Look Charles, do I look like I weight 130 pounds?" Thelma was gorgeous in her new gown but thought it made her look heavy. I said rather casually, "I weight about 130 pounds. There is no way you do Thelma." "No way Charles, you're only a hundred and thirty pounds! Ginger his hips are almost as wide as mine, right?" Ginger came closer to us, "I'd say his are close and you two are about the same height, but in your sexy heels you tower over him." Thelma smiled, "I have to work my look carefully otherwise I look like a boy. Shit, I guess I look like a boy!" One of the cooks settled it, "Here's my tape." Jon announced that, "Thelma has thirty-seven and a half inch hips and Charles is a thirty-five." The head chef came near smiling, "Yes, I'd say Charles is too beautiful to be a boy. To bad we only need two hostesses." He came near Ginger and held her waist, "Now, get this nonsense out of my Kitchen girls!" This statement surprised me and I guess I looked wounded. Ginger came to me and whispered, "He's just jealous that we pay so much attention to our pretty boy." One day Ginger arrived at the Inn but was a bit late. She was wearing another ankle length gown and holding her heels. Her stocking were torn. She stepped to the restroom and a moment later came out with her heels on. "I removed my hose'. I hope I don't form a blister in these nearly four inch heels. My Camaro broken down Charles about a mile down the River Road. Can I get a lift home later from you?" I had earned enough to buy a bucket of loose bolts and sheet metal that passed as a car. "Alright Ginger but you've seen my banged up ride so don't expect a limo." She hugged me, her breasts touching my chest and I almost shot a load. How would I get through this night? I hadn't had a sexual thought of her since Thelma had come to work at the Inn. Now she wanted my help and all I could do was lust after her. I felt like a heel. Her cleavage was all I could think of as I worked that shift. When I drove along the narrow road after work to her place my mind was imagining all sorts of scenarios but nothing happened. Except her very sensual kiss goodbye. She actual pushed her tongue into my mouth! Then she turned and headed to the door as she spoke. "You're my new best toyfriend Charlie. Thanks for the kiss," and she was gone. My crotch was now damp. Did she say 'boyfriend'? Later that week I saw Ginger and Thelma kissing passionately in the back empty dining room. I hadn't ever considered that these two women whom I knew so well might be lesbians. It crashed my fantasies. I moved quickly around the corner to avoid their seeing me. Then I heard Thelma say, "I want to be with your toyfriend when she's ready." Ginger swore, "Fuck you if I'll allow that to happen." She giggled and continued, "We'll find a reason to share the new girlfriend don't worry." The next week she asked for another ride since her car was in the shop. Thelma had suggested that she could drop her off. They stood quite close, their hips nearly touching. "Thanks Thelma but I'm having Charles help me tonight. You can help me some other time." This time when we arrived at her apartment she asked me to come in for a drink and a joint. Sitting alone with her was too much for now I could see her beauty relaxed and only for my eyes and imagination. Her apartment was simple but clearly a feminine home. The smoke now filled the room and the music was sensual. I was enjoying being this close to this beautiful woman. "Can I use the bathroom Ginger?" "Sure just through there." I closed the door before lighting the room and was surprised to see in the comfortable bath stuff everywhere. This was the workroom necessary to put this beauty together each afternoon. Her bathtub was draped with drying lingerie and true stockings. Her large counter covered with makeup and lotions and the room opened into her dressing room and bedroom beyond. I paused as I reviewed the sheer hose, my fingers touch the material. I stepped to the doorway and saw the many dresses, work gowns and so many pairs of heels in different styles and heights. Beyond I saw a large dresser, the upper drawer open and the collection of colors and fabrics. A cream-colored bra and panty were hanging off the drawer pulls. I moved to the counter and sat on the small stool as I studied the multitude of colors and brushes and the scent of the various products. When I paused I looked up and to the right toward the dressing room. Ginger stood looking at me over her shoulder as she dropped the blue sequined gown off of her body and it fell to the floor. Her lingerie was lightly confining her sexy body and I looked first to her tight thong and then down her legs. "I needed to get out of this wrap. It's so tight. Can you imagine it Charlie?" I was lost; she wasn't wearing a bra and her large breasts were filling my eyes. Her deep colored areolas and taut nipples caught my attention. I was staring at her body and then I looked to the mirror just beside her and saw the cleft of her bottom where the thin material of her thong disappeared. "You haven't seen a woman this undress huh? Well don't fret my new toyfriend. I've got you right where I want you." She turned, still in the three and a half inch satin blue heels and the gartered hose', and walked into the bedroom. I watched her beautiful motion and didn't hear her speaking for I was so overwhelmed by her body. As she approached again speaking I was transfixed watching her breasts move. "I said get into the shower with that cream on the little shelf and the razor." She had re-entered the bath and was standing only twenty inches away while I was seated. She looked down to my face, bent slightly and kissed me deeply. I reached for her bottom and held Ginger close. "I want you to be my lover tonight and 'Charlie' is such cute name for a girlfriend. Get naked and start shaving sweetie." She moved close and kissing me again as she pulled me to stand and reached to run the shower. "Should I remove these old rags Charlie? You'll need some help with your back and your groin so I'll stay. Come on girl! Your legs will require the most work." She was confusing me. I was to get into the shower and shave? My back and legs? Her girlfriend? Cute? I realized that I could get laid by Ginger tonight. I was going to sleep with her but she wanted me to do what? It finally dawned on me. She wanted me to be smooth, "Why do I need to shave Ginger?" "Because girl's are smooth Charlie. I want my lover smooth and sexy so we start with the razor." She had reached for my belt and now my pants hit the floor. "See, the legs Charlie, Now!" I considered where I was and what she wanted of me. So began our evening. I acquiesced to her intent and within fifteen minutes she was doing my face and shaping my nails. Thirty minutes later I was being shown how to roll a hose' and clip on a suspender belt clasp. I didn't pause to comprehend where I was headed with Ginger. I just followed and said very little. An hour after arriving she slipped into the shower while I stood near the mirror, "Well how do you feel about your new face and body Charlie?" I was still in the bath as she talked over the sound of the running water, "I knew when I met you I was correct. You aren't a boy Charlie. You're my girl. I want you to stay tonight and make love with me. Do you think you can handle that?" I looked into the mirror. There was little evidence of Charles, the boy I had been just before stepping into Ginger's bathroom. She had helped me with the earrings, the bracelets, and the bra, which was filled with the very real feeling silicone forms. The heels weren't as much of a problem as they were lower then three inches as they were. My waist was drawn tight with a waist cincher that held the sheer hose. "I'll help you into one of the gowns in just a minute but I wanted you to take in what you are Charlie. I wanted you to see you as I see you. With some skill your hair is styled similar to Thelma's which I find very sexy. Can you understand how wet my pussy is?" I said just two words, "I'm Charlie." To be continued. 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 ***** 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