An Apprentice Needs Help

by Wannabe Ginger

Chapter 6

Ginger's home was shrouded by the rain as I walked towards the door. This evening was going to be special. I had made sure that I had shaved more closely than ever before. I wore a cool denim jacket, crisp white shirt and blue chinos. Male. As I had left the house, Mum's words confirmed it was right. "You're looking good tonight — is it an important date?"

I nodded and smiled. "You could do with fixing the colour again, honey — it's growing out and fading at the same time." Her own hair showed the value of constant care — you would never see roots in her hair (and she wasn't about to follow the fashion of showing roots intentionally!)

Male.

I wanted Ginger to receive me that way. However we ended up. I would start the evening more male that she had seen me over the last six or eight weeks. My hair couldn't be changed. It was now long and the colour was still brown, ready for the competition, although it was fading and my own colour showed quite markedly at the roots. I had purposely dried it rough and pulled the longest parts, from the sides of my face, up with a band. Metrosexual, they called it. Indeed, I was becoming the best example of metrosexual man.

So much so, I had my metrosexual undies with me. The ones that Ginger had been with me to choose and to buy. She had even selected the colour, the lightest silvery blue, with plenty of lace. The knickers were 'long leg' to be the right size and not too tight — no thongs for me thank you very much. The bra was lined with soft fabric and finished around its edges with the most delicate lace. It was stretchy, though, and clung to my chest.

Ginger showed me how to gently push the skin of my "pecs" into the cups of the bra to show the nipples off best. The suspender belt was long and its straps were stretchy too. Long enough, they were, to reach the stockings that still remained in their packaging. I had yet to experience the clingy softness of stockings on my legs. The simple idea was extremely sexy!

But that was not for now. That might be for later. Now, I was Male. Indeed, even then later this evening, even if all of those things were worn, even if my hair was done again into the most wonderful style, back-combed high, and even if the make-up was double glamorous — even if my transformation was complete for the first time.

Now I was to be Male.

How glad I was. It was right. As soon as I saw Ginger at the door. A vision of femininity, she was. From head to toe. Beautiful hair. Pretty face, squeaky clean with no make-up yet. A pretty dress that was shaped closely to her figure, placing the right emphasis on her 38B bust and tiny waist. Her long legs were silky smooth in the sheer stockings that I knew would be just like the pair she had chosen for me, for tonight and for the competition night. She was ALL girl tonight!

As I entered her place, I smelled her perfume. It added to the heady concoction that was building in my mind. "You look and smell wonderful." I said. "You too." She replied. We kissed and lingered before moving into the living room where there we two glasses already poured. "Aperitifs." Ginger said. "Martini. Dry." No choices — Martini was evidently for special evenings.

"I've not tasted Martini." I said. "Well, you should, and you will." Ginger said, moving closer, offering the second glass. The atmosphere was again best described as "heady". It would get more so with a little alcohol and a great deal of "intention".

It was clear that we both were in the mood for love and a first sexual experience together. Our hands touched. Our eyes met and our lips closed in on one another's. There was a pause in the moment that it dawned, we would have sex as boy and girl. We were bound to — there was no escaping it, even if one of us wanted.

The kissing became more prolonged and the alcohol took its effect. The Martini had exactly the desired effect. The kissing turned to passion. Our tongues searched out eachothers inner cheeks. The moment was right. The moment was NOW.

Our hands explored eachother's clothing. Buttons and zippers were undone. Garments were removed within moments. There on the floor in the living room, we joined in a wonderful near frenzy — simple desire let loose. All of my fantasies about her were coming true.

This wonderful girl was mine and I became hers, there and then.

We were lost in a tangle of arms and legs and tongues and nipples and even the hairlines of eachothers' precious fantasy hairstyles. I kissed her ears and licked all along the nape of her neck, my tongue straying into the glorious red curls that she had combed out until they shone, before I arrived.

The love-making was wonderful. The way our passions entwined. Time became suspended as we explored every way in which we knew how to please the other. She gave as good as she got!

Once the passion had been fulfilled and the moment of each of our climaxes, with hers repeated, passed, we lay in a gentle huddle each of us listening to the other's breathing. Pulses no longer racing. Warm in our arms, joined together.

Time meant nothing to me. It was Ginger who spoke but didn't break the spell that had woven around us. "We have to practice — we can do that better!" She laughed and then said, "if we're very lucky!!!" I laughed too. When? Was all I could wonder. When could I be in this wonderful woman's arms again?

"But this isn't what we're here for. You're on a promise, as I remember!". Ginger's words were soft but insistent. "You're here for more than that." Her words were unmistakable. "Nothing can make the evening better" I said, genuinely meaning that there need be no other activities tonight. Meaning that I could happily spend the evening in the afterglow of a truly passionate girl/boy experience. "Nothing at all."

"Ahh. You don't get away that easily. You have to earn your treats if that's what you've been doing. Have you been going along with the hairdressing just to get inside my knickers!??? …….You should be ashamed!!". She taunted me.

"How far will a boy go to get to have sex with a poor vulnerable girl like me?!" "Even going to the shops with me to buy some undies for yourself!…. even letting me buy them!" Her words gathered enthusiasm for the play-acting she was indulging in.

"I'm going to steal all the clothes you came here in, so you'll have to wear some of mine!"

There could have been a grain of truth in what she was saying. Perhaps I did get into this to get this far — but it was probably with Karen who I had fancied all the more beforehand. Perhaps Ginger had been an "unattainable" dream. But the, perhaps not. Perhaps the hairdressing was really for its own sake. This sexual encounter had become a wonderful "spin-off".

There was no secret that I was enjoying the hairstyling and how it was making me look. Perhaps I had gone too far with the make-up but I didn't think so. Ginger stood there, expecting an answer — or at least a protest.

"You'll have to wear some of mine, was what I said!" she cried.

"You're a wonderful, beautiful, fantastic lover, and I'd love to do that all over again." I said — hoping, but not knowing, if it was in my powers to come to a wonderful climax again so soon. "Well, you can't!" Ginger replied. "You're here to be transformed."

My clothes were strewn all over the room, along with some of her own. She suddenly jumped to her feet and gathered almost all of my clothes into a bundle. "There!……." she exclaimed. "I have them all! Now what will you do?!"

She was right. There were no other clothes. Her dress lay on the couch. It had clung to her body beautifully. She still wore the stockings that had made her legs look so silky smooth. Her bra and knickers and suspenders were still on her as she soon made clear, "You have your own undies with you, don't you? You promised you would bring them here. So let's start with them. Where are they!?"

I motioned towards the small parcel I'd left by the door.

" The bra should be first, then the suspender belt, then the stockings. Then we'll see how sexy it makes you feel dressed in such girly things. And then we'll see if you're up to having sex all over again like you say you want. Then, and only then, can you put on the panties to hold you in for a while."

I had no choice — but to go along with this charade. It was clearly her plan and I was a willing partner in her game. "I'm going to watch you." Ginger said, her eyes sparkling with a seductive glint. "You know that this really hits on my hot buttons, don't you?!" I did indeed, and it was hitting mine too. "Take your clothes off — all of them!". As Ginger watched, I tried my best to make it seductive in return. This ended, leaving myself standing in the centre of the room, stark naked. Naked at first, I reached for the bra I had brought with me. It was that wonderful shiny, silvery blue. The lace was beautiful. It was a delight, just thinking of putting it on.

"When do we get to do my hair, then?" I asked, prolonging the anticipation of fastening the bra. Ginger said nothing. "We could start with that." I suggested. Ginger again said nothing. She simply looked at my helpless, used, manhood that was beginning to awaken again — just at the thought of my hair being dressed again, not to mention dressing in her clothes and the undies I had brought.

"I'd said I'd prefer it if I dressed after my hair was done." I said again.

"Then come with me and we'll find something comfortable for you while we do that." Ginger's tone had changed. She was much less the loving, accommodating girl that she had been while we made love. She was more forceful in her tone. There was no question. I was to go with her.

She led me to her bedroom and in a quite off-hand manner, held me a nightie, a silvery blue nightie with lace, one that matched the bra and other underwear we had bought in the shop the day before.

"After we went shopping, I went back and bought this for you — it completes your set. It all matches. You must promise to wear it from now until the competition. Put it on now, and we'll do your hair — then you can do mine, and after that, we can dress you and do your make-up. Your complete transformation."

Could this girl be more perfect? How did she learn to read a boy's passions and get the timing right? Was a complete transformation what I wanted. Could it be, given the way we had just made love as boy and girl? Her insistence grew. "Put it on, now! I can't wait to see you and feel you in it!" She really meant that. I could tell just how aroused she was becoming —as, indeed, I was myself.

The wonderful long silky garment went to the floor and I simply stepped into it. I drew it up my legs, over my hips and on to my body. By this time, a problem arose — quite literally! The nightie became mis-shapen as my cock grew in size again. Before I could raise the shoulder straps of the nightie into place, she exclaimed:

"We can't have that! A nightie has to be sheer and smooth and flat at the front below the boobs — and as you haven't any of those yet, ("Yet!!??), you certainly can't have anything else showing! Pull the straps over your shoulders immediately!" I did as she demanded. There was no alternative. Each strap slid over the shoulder and the lacy front clung to my chest. My flat, male chest. What did she mean… Yet!???

"Now lift the hem of the nightie!" Again, no chance to do otherwise. I did so and exposed my now very full cock that stood out towards her. Ginger was close enough to reach out and clasp it gently between her hands. She squeezed me, gently at first and then more strongly. Her had began to push towards my pelvis, and then back towards the head of my cock.

Slowly, everso slowly. And back. And forth. My mind was again in a spin. I stood, clasping the hem of this wonderful silky blue nightie, my own hands having nothing else to do.

Ginger slowly sank to her knees before me and her hands drew my cock towards her. Pulsating, I was ready for love-making again, but could do nothing. Her lips gently curled towards the head of my cock and she began to devour me.

One of my hands strayed from the hem of the nightie. Up towards the breast line of the nightie. I began to fondle the nipple through the lace as she took my cock in and out of her mouth. Deeper and deeper she seemed to go. More and more my nipple became hard and the skin around it wrinkled in pleasure.

As my hand caressed my nipple, my thoughts moved to my hair, that was how this all began, washing my hair with Ginger watching.

That became colouring my hair with Ginger deciding the colour I should be. It led to a cut, that was now growing out. Again, she had encouraged me. Tonight, it had become part of the transformation I was to have done. My other hand slipped to my hair, leaving the hem of the nightie to fall around Ginger's head as she knelt between my legs in front of me.

My hand ran through my hair, its length now full and its thickness growing. Its style had evolved, from firstly being just a long mess that had no shape, to now being a true style with panache, its ends now blunt cut with the curling under at the level of my jaw line, its crown raised with backcombing that I could do myself, and the nape of its neckline still cut close - where the colour would be dramatically changed for the upcoming competition. Shortly after the thoughts of my hair broke through, I felt a dazzling, sensational orgasm, my cock still deep within her mouth.

I could do nothing else but ease my cock from her mouth and pull her to her feet. Kissing her firmly on her wonderful mouth, I parted her lips with my tongue and shared the cum that had been mine a moment before. She was close to bringing herself to an orgasm and so it was, with a deep kiss, she trembled with exhilaration and we fell together on to the sofa nearby.

We stayed there, she in the clothes she had been wearing, me in the nightie that she had insisted I wear. We lay there for fifteen or twenty minutes, both breathing shallowly and purring with pleasure.

Eventually, it was she who spoke first. "Now we have that obstacle out of the way, we have to do your transformation. And once we have done that, I want you all over again, my boy…….. my girl with a cock!"

"You're truly wonderful, you know that." I said, still breathless. "What a way to deal with a small obstacle like a cock, temporarily in the way."

"Temporarily….. hmmmm," she said thoughtfully. "We can't keep having that happen — and, in any case, I want to save you for later. Wait here a minute." Her words were an instruction. What I was to wait for, I couldn't guess. Soon, she was back with her hands behind her back. "Lift your nightie and close your eyes!"

I did so, and within a moment felt her hands cradling my cock — surely not more love-making, not so soon! "Eyes Closed!!"

I felt manipulation, I felt something being put under my balls and then over, from both sides, my cock. It was tight. It had a tightening feeling. Back over and under, behind my balls. Up and over again. This time further up the shaft of my cock. Tighter now. The third time, whatever this was went under my cock but not behind my balls — just around my cock - which was growing again. "No! You must not let that happen again — not now!!" she commanded.

It was evidently some material, something very stretchy, that was enclosing my balls and now my cock. Under her control. Finally, after another wrap-around, she passed the material down between my legs, pulling my cock down — very tightly - to where it would be out of sight.

Ginger moved behind me and pulled on both sides, taking the material behind my body. I was strapped tight. She tied the ends together behind my back, as if in a thong. "That's better — now I know where to find you when I need you!" she said, as if to my cock, without reference to me. "Hair wash, make-up, drying and styling, and then to try the last of the undies we bought you when we went shopping together!"

Over the next half an hour or more, my hair was washed, as before but with extra conditioner to make it shine. Ginger towel-dried it all over, and then added fewer rollers, but bigger ones, to make the style I was now getting used to. It was near enough a Pageboy Bob, with long sleek sides, a raised crown and the ends of the length turning under. To the back, the shorter hair at the nape of my neck was nearly covered.

It was the same colour all over, apart from the roots now, this did not matter at all but it did make me wonder, looking in the mirror that Ginger held to show me how the rollers had gone in. It made me wonder if I would ever have this "under-colour" effect put in. My hair was still brown, still rather dull if you ask me. I was beginning to want a little — no a lot — more exciting colour. The initial experiments had left their mark on my psyche.

When the rollers were entwined, and I had become transfixed with Ginger as she was now the one controlling what my hair would be like, we were ready for a glass of wine. With that, Ginger said, we should discuss my make-up and how best it would look — what colours did I fancy, what tones in the eye shadow and lipstick. She started with a liberal covering of base foundation, to prepare the skin. This covered my lips and I asked why this should be — "To make it longer lasting and more kissable….." she replied. "You do expect to be kissed after all this, don't you?" Her voice was teasing again, but in a gentle way. My love for her knew no bounds!

Ginger's next steps were to work on my eyebrows, which were lined in brow rather than black. She took a brush to the eyebrows, and decided that several stray hairs needed to be plucked to give better shape. Ouch! That hurt! Ouch! Again… and again. On and on, she went, until she was satisfied. I could not tell how much damage she had done there without getting closer to the mirror. I was later to find that she had been very gentle and reserved in the eyebrow plucking that she had done. I found this out the evening before the competition. That was when Margot's mother became a controlling influence in the "Models Make-up" practice.

Ginger's skills with make-up were remarkable and before long, my hair still rollered, I was facing a female in the mirror. My eyes had a wonderful blue haze of eye shadow. My eyelashes were curled and covered in blue mascara. I had not experienced the false eyelashes when we were last together but Ginger had come prepared with a wonderful long pair of spiky lashes for me. This took the longest time and caused the most discomfort. Eyes streaming, and mascara beginning to run, we had to pause — in fits of laughter.

Eventually, the lashes were in place and I was stunned by the change in the look of my eyes in the mirror! Absolutely stunned. Almost as much as the hair had transformed my looks, so the lashes added a wild sexiness that I hadn't seen before. Ginger was enraptured "I never thought they'd look so good! I must have a pair for the night of the competition!"

My cheeks were swept with crimson blusher. Most of all, I was fixated by the lipstick — the same Christian Dior shade that Ginger had used when we first kissed. The taste was unmistakable. I decided there and then that I should buy one for myself. All of the cosmetics were Christian Dior. Wonderful!

My hair was dried with a hand held dryer, in front of the mirror. The rollers were, again, quite huge on the top and crown of my head. This allowed my eyes never to leave Ginger's face. She knew how wonderful she had made me feel. Her hands soon began to remove the rollers after my hair had been dried and allowed to stand to cool.

Before starting on removing the rollers, she asked "Have you ever slept in rollers?" To which I answered "Not yet." There!… I was doing it now. I could easily envisage going to bed like this. Even having sex whilst in rollers — there would be a thrill! As such thoughts entered my mind, my cock again began to rise. Held within its sheath of elastic lace, there was nothing it could do — except swell, deep down between my thighs.

Ginger took the first roller and began to unwind it, her eyes stared directly into mine. "All of this is being done in secret and that means you're missing the experience of sitting in a salon having your hair styled. You should try that one day."

I think Ginger sensed my arousal, saying "The style will be simple tonight. I think it's time you had a beehive! Like my "Big Hair" that turns you on - why not!".

She was right. Larger rollers, my hair now reaching the desired length. It was ready for a change — and I could live with that. After all, the colour was going to be done next week. Why not an extravagant style now?!

She began to unroll the set and the other curls, that now looked huge to me, sprang into the places they had been dried. I felt an irrepressible desire to run my hands through the curls. They just invited a touch. But of course, I didn't! I had to leave them to her to deal with.

She began and, with what felt like increasing ferocity, Ginger created a wonderful cloud of hair around my head. At one stage, I swear it stood nine or ten inches above the scalp — in all directions.

She then swept the stray pieces into place. It was time for the lacquer. Clouds of spray were coming at me from all directions. Her brush began to sculpture the style out of this cloud of brown hair. How I wished it was RED!

As the style took shape, the pressure in my restrained groin was almost unbearable. She had tied me in very tightly, even when I was small down there. My cock was now much much aroused. The thought of her mouth around it came flooding back. The hair was swept this way and that, taking a wide and high outline in the mirror. It was very much a "Sixties" look that I loved within a moment. The nightie still clung to my chest. My nipples were doubly sensitive. All of this was becoming too much to bear. My heart beat faster and Ginger became aware again. Aware of my arousal, aware of my mild discomfort.

"Just take it easy." she advised. "We have plenty of time and this hairstyle needs care in the finish. You're going to look stunning!"

With the make-up she had applied so expertly, and now the hair back-combed and lacquered, there was time for a pause. I sat back in the chair and admired my brunette hair and make-up. There I was, sitting at the dressing table mirror, clothed only in the silky blue nightie and with a female face and hair adorning my picture of myself. Thoughts came to mind that said I could almost fancy myself as a girl. I had lost none of the masculine appreciation of the female form — except that now, that form was my own!

We never did get around to styling Ginger's hair that evening. We made love yet again — this time with my transformed vision of womanhood and her still gorgeous feminine form. Confusion could have over-whelmed me but everything told me that this was hat we both wanted — nobody could write a book about such an encounter — so early in a love-life that we were beginning to share. Ginger clearly wanted me as a male and also as a female — but both of her lovers had a cock for her! My dreams collided with eachother. I had never thought of such a situation. I was loving every minute and she, too, was as horny as hell because of the way I was able to take on board the transformation that I had. Deep inside her again, time and again, my lipstick found its way not only to her lips, but to her nipples, to her thighs and to her love nest. My hairstyle was so well set, I emerged it seemed hours later, with a perfect style — well, nothing that a brief comb-out wouldn't make perfect.

As we lay after making love again, I began to think about the walk home. I was dressed in female underwear. I was wearing full, and very colourful, make-up. My hair was now in the most dramatic style I had yet experienced. If I walked home like this, I'd be arrested! If I walked home in Ginger's outer clothes, I'd still be arrested — for soliciting!

There was no alternative - Ginger's family were away for a few days. I could not go out — I had to stay. It would allow me to sleep in what I was wearing, wake in the morning and, I hoped, make love again with Ginger……………. after removing all my femininity!

After all, there was the weekend coming — and the hairstyling competition!!!!!

TO BE CONTINUED……………………………….