The Transformation of Paul Ch. 03byTheGentleman©
After breakfast, we drove into the town. As Gerald had suggested, I had left the stockings and the majority of the lingerie on underneath my clothes. Only the bra had been left behind since it would have been very noticeable under my thin summer shirt.
I sat in the passenger seat and leaned my arm on the sill of the open window. The breeze was channelled into the short sleeve of my shirt and if I pulled the seatbelt away from my chest, I could funnel it to blow directly across my nipples. Whenever he didn't need both hands on the wheel, Gerald would drop his left hand down onto my thigh and gently stroke my right stocking top and suspender through my trousers. Each bump in the road caused the elastic in my undies to tug and as we went round corners, my satin covered buttocks slid sensuously from side to side. Unsurprisingly, my cock was semi-hard and lolled around heavily in my panties. The precum was obviously in free flow as every few minutes, my cock would encounter a cool wet spot on the satin. There was a box of tissues on the dashboard and having pulled one out and sucking in my stomach to give myself access, I stuffed it into my panties to mop up. Gerald was grinning broadly.
"Getting over excited again?"
I punched his arm playfully.
We drove for about 10 minutes and finally parked on the side of the road by a short parade of small shop units. This part of the Old Town had narrow streets and had long since been deserted by the everyday shoppers who sought quicker and easier shopping under the roofs of the out of town hypermarkets. What were left were the small specialist shops that relied on a steady flow of regulars.
"What size are your shoes?"
For a moment I was taken aback by Gerald's question.
"Err.... Size 7".
"OK" he said, "you wait here while I do some shopping.
I sat in the car and watched the world go by. It seemed so strange to watch ordinary people doing ordinary things. Yesterday, I had been ordinary, looked ordinary, behaved in an ordinary way. I realised that of course I knew nothing about the people who strolled down the street. I took them at face value but really their private lives were as mysterious to me as mine was to them. After all, for all intents and purposes, here I was, a normal looking 18-year-old male, just sitting in a car waiting for the driver. They could not possibly know that underneath my everyday clothes there was a body that had been completely depilated from the neck down and from the waist down was clad in the most feminine lingerie and stockings. I realised that Gerald was right, again. My secret was exciting.
My revere was interrupted by him opening his door and sliding back behind the wheel. He leant into the back of the car and deposited a fistful of carrier bags on the back seat.
"You weren't long," I said.
"No, I only had to go back there". He turned in his seat and pointed out of the back window to a small shop on the other side of the road.
I twisted my head round to look and I could see a tiny shop with iron grills at the window. Above the shop a sign in gold lettering on a black background read Narcissus.
I was curious about his purchases.
"Wait and see," he said.
He started the car and we drove through the sunshine to the seafront.
"Let's walk for while".
We strolled along the promenade, for all the world looking like uncle and nephew. Little did anyone know!
The late morning sun worshippers were busy applying lotion and oils and arranging their towels to get the best angle to the sun. I eyed the girls appreciatively but I soon became aware that my interest was as much academic as lecherous. I was comparing breasts and legs, watching the way that buttocks moved inside tight bikini bottoms and checking out hair colours and styles.
Gerald was mind reading again.
"What do you fancy?"
I realised that he had said what not who or which one. He had taken it for granted that I had fully embraced my new girlie lifestyle and I was only slightly surprised to realise that he was right. There was no doubt now in my mind that I really wanted to be a girl. Even as I looked on I was wondering how it felt to have a heavy pair of breasts attached to me, how it felt to feel them wobble and bounce in the confines of their lacy suspension in bras and other lingerie. How it felt to have men stare at them and even rub their stiff cocks between them and how it might feel to run my hands up over my smooth stomach and cup them in my palms, feeling their softness and fullness, stroking my nipples into hard points.
"Nothing too big," I replied eventually. I nodded towards a girl in a jazzy yellow and blue bikini. "Like those".
"Good choice. Not too big, not too small. They'd look really sexy on you," he said.
He reached out and casually brushed the back of his hand against one of my nipples.
"Can you imagine it?"
There was no doubt I could. My balls and my asshole were involuntarily contracting at the thought.
"Oh yes, can I".
"So can I," he said "but I promised you that we'd work on your nipples first. What do you say we go home and make a start?"
We walked back to the car in silence. The idea of having real breasts had really excited me and Gerald's promise to a start making my nipples bigger, both combined to give me yet another throbbing hard-on. I slipped one hand into the pocket of my trousers in an effort to keep it less obvious but even this proved not to be easy. As well as feeling my hardness through the lining of the pocket, I could of course also feel the stocking top, the taut suspender and the gloriously soft satin panties. In the end, I finished up half trying to hide my erection and half stroking it into a bigger and harder length of flesh. Gerald watched my obvious discomfort with amusement.
Maddeningly, he insisted that we stop for drink whilst on the way home and pulled in to a public house near the seafront. We sat on a terrace overlooking the beach and watched the sunlight sparkle on the water. I knew that he was teasing me, prolonging the agony of anticipation for the next part of my education.
"There's someone I want you to meet," he said. "His name's Charles and apart from the fact that he's just about the biggest Queen I've ever met, he and I have been friends for years. He's bit of a shock at first but I know you'll like him".
"A shock in what way?"
"Well, lets put it this way. He's quite tubby, very, very effeminate and in every way imaginable, totally larger than life. Anyway, you'll see soon enough. I've invited him over after dinner".
At that moment, "after dinner" wasn't very high on my list of priorities. By now I was itching to know the contents of the carrier bags in the car and to get back for my nipple treatment
"Can we go yet?"
Gerald checked his watch. "Yes, OK, Mrs Warren should be finished by now".
I'd forgotten about his housekeeper and felt a brief rush of embarrassment at the state in which we had left his bed.
"Doesn't she ever ask about your, er, guests?"
"No, never. That's one of the reasons I employ her," he said. "She gets paid above average and I get complete discretion on her part. It's a good arrangement".
Despite his assurances, I was glad to find the house was empty when we got back. It had obviously been cleaned and the smell of lavender furniture polish hung in the air. Gerald had taken the carrier bags from the car and had started up the stairs.
"Come on," he said, looking over his shoulder.
The bedroom was clean and tidy and the bed was freshly made. Gerald threw the bags onto it and walked across to open the windows.
He came back over to me and stood close, looking down at me.
"You know, you really are lovely", he said and bent down to kiss me.
His lips brushed mine for a moment and then he continued to give me little kisses across my upper lip and on my cheeks. His gentle hands held my face as he softly kissed my eyelids and eyebrows and then he kissed his way down the slope of my nose. He licked gently across my lower lip before he pushed his tongue into my mouth and kissed me properly.
He pulled back and started to unbutton my shirt.
"I hope you like what I've got for you".
The shirt slipped from my shoulders and he spent a few moments stroking his long, elegant fingers over my back and chest. Next, he knelt in front of me and slipped off each of my shoes amd then he undid my trousers and pulled them down. I raised each foot to help him and when my nylon-covered legs were free, he sat back on his heels and looked at me.
"So, beautiful," he murmured.
He leant forward again and pressed his face into my panties. I could feel his cheek pressing against my erect cock and his hands travelled up the back of my stockings to clutch my satin covered buttocks.
Gerald rested like that for several minutes, rubbing his cheek across the hard outline of my shaft.
"You feel so good," he said at last. "I wish you could stay here".
I brushed my hands through his hair and held his head to me.
"Me too," I said and added "I mean it, I really do".
A few moments later I felt him undo the suspender clips and then he rolled the stockings down my legs. Then he undid the suspender belt and finally dropped my panties around my ankles. I stepped out of them and leant down to pick them up. The tissue I had used to soak up my precum was sodden and the wet patches on the satin had dried to a white crust.
Gerald took them from me and scooping up the rest of my things, dropped them in the laundry basket.
"Mrs W can take care of them. They'll be good as new".
He walked over to the bed and sorted through the bags. He handed me a long black silk robe. It was trimmed with red lace and fastened with a red silk belt. I put it on and shivered with pleasure as it caressed my skin. My slightly wilted cock pulsed back into full hardness.
"I don't think this is ever going to go down", I said pointing at it.
Gerald took a tissue from the side of the bed and came over to me.
"Mmm, goodie", he smiled.
He took me into his mouth and gently licked the sticky coating of precum from my shaft and helmet before wrapping the end of my cock in the tissue.
"Don't mess this robe up," said with mock sternness. "At least, not yet!"
I tried to concentrate on deflating my cock. It was hopeless. I was as aroused as I had been all day and not only was the silk robe slithering exquisitely over my nakedness but I was now desperate to know what other surprises Gerald had in store for me.
He reached into another bag.
"Ah, yes," he said, "a little something for those lovely tits of yours".
In his hands were what looked like two elongated thimbles. Each looked to be about an inch and a half in length and perhaps half an inch in diameter. From the closed ends, small clear plastic tubes ran down to a sort of control box. It was made of black plastic and was about the size of 3 packets of 20 cigarettes, placed edge to edge. It was attached to a wide black elastic belt. Gerald slipped a panel from the back of the box and started to insert a number of batteries. When he had finished, he snapped the panel back into place and motioned me towards him. He reached round me and fastened the belt behind my back so that the black box lay flat against my stomach. He held out the two thimble ends.
"Hold these a moment," he said.
He went back to the bed and returned with a small tube. He squeezed a small amount of jelly-like substance from the tube and applied it to each of my nipples and the surrounding areolas. It felt like an ultra slippery lubricant.
"Now for the best bit," he said. "Press the cups over your nipples and make sure you push down firmly.
He reached for a switch on the control box and stood back.
For a moment, nothing happened. Then I heard the box start buzzing and the next thing, my nipples were sucked gently up into the thimble-like ends. The little box continued to buzz and then hiss, buzz and then hiss and each time, the suction pulsed through the tubes and encouraged a little bit more of my flesh to be sucked up. It was a strange but pleasant sensation and I could feel my nipples engorging as the blood was pumped into them.
"We'll try an hour to start with," said Gerald. "Come downstairs with me while I get the dinner ready. There's bound to be some cricket or something on the telly".
I belted my robe over the nipple machine and went down to the sitting room. Gerald headed for the kitchen and after a while, the clunk of pots and pans and the sound of chopping and mixing, mingled with the laconic commentary that accompanied the Golf tournament that was showing on the television.
After a while, he brought me through a huge glass of red wine.
"How are they doing?" he asked, nodding in the direction of my tits.
"Fine," I said. "It feels nice".
"You wait till you take them off," said Gerald. He was grinning again.
He returned to the cooking. I sat on the sofa listening to the buzz and hiss of the little box strapped round my waist, the noises from the kitchen and the occasional muted excitement of the commentator as somebody managed a "birdie" or strayed into a bunker. It seemed to be totally bizarre. I was sitting on a sofa, in a comparatively strange house, dressed in another deliciously feminine item of clothing and having my nipples sucked by a machine. Yet the ordinariness of everyday life was continuing around me as though nothing was happening. Most bizarre of all was the fact that I didn't mind. In fact, I was loving every minute of it.
A couple more glasses of wine later and Gerald announced that dinner would soon be ready.
"Before we eat, let's go upstairs and complete today's transformation," he said.
He preceded me up the stairs and into the bedroom.
"I should think you're about done now," he joked.
I loosened the belt on the robe and let it swing back. The little machine continued to buzz and hiss but I had got used to the sensations and for the last half an hour or so, had hardly noticed them. Even my ever-erect cock was only slightly swollen. Gerald switched the machine off and unbuckled the elastic from round my waist. Gently, he detached the thimble-like cups.
It was an incredible sight. During the time that I had been attached to the nipple sucker, my teats had completely changed shape and size. They had grown to at least a half inch in length and had fattened proportionately. They were a deep pink in colour and stood stiffly away from my chest.
"Not bad for a first go," Gerald said. "They're bound to go down a bit but with plenty of practise, you should be able to get them to completely fill those little cups. Then, if you like, you can go up to the next size and so on".
I tweaked them gently between my fingers, marvelling at their fullness and sensitivity.
"You mean I can get them bigger than this?"
"Much, bigger. Wait 'till you see Charles'".
I had forgotten all about Charles.
"Are his large?"
"Like I said, everything about Charles is large".
Gerald stooped and sucked each nipple in turn into his mouth. He rolled them around his tongue.
"God, my darling, that's so sexy. Just wait 'till I've finished dressing you".
I didn't have to wait long. He sat me down on the edge of the bed and took some styling gel from one of the bags. He rubbed some into the palms of his hands and then smoothed it into my hair. I had never gone for the fashionable haircuts and although my hair was regularly trimmed, the overall length covered most of my ears and rested on the back of my collar. Taking a brush, he spent some minutes giving me a new parting and pulling the majority of my hair back across one side of my head. When he was satisfied, he reached into the bag again and produced a can of lacquer.
"Don't worry," he said, "it looks great and if you don't like it, all you have to do is wash it again".
From another bag he produced a make-up case. Foundation, eye shadow and mascara were followed by lipstick and lip-gloss and a final dusting of face powder completed the picture. Next, he took out a little clear plastic box and extracted a short tapered tube. On to the narrow end, he rolled a small transparent rubber "O" ring. He placed the larger end of the tube over one of my nipples and rolled the ring down it. It snapped off the end, trapping the base of my nipple. He repeated the action for the other one and then holding the rings with the tips of his fingers, he used his other fingers to pull the nipples through the rings as far as they would go. The effect was to trap some of the blood supply and engorge my teats even more. I could feel them throbbing in time to my pulse.
"They wont go down for a while now. Are they comfortable?"
The penultimate carrier bag contained even more lingerie. This time, the stockings were black, with seams up the back. A black satin suspender belt was trimmed with red lace and my black satin panties had a red bow at each side. A see-through panel in the front showed off my shaven cock and balls. The bra was also black satin with red bows but also like the panties, it had see-through panels in the cups. My fat nipples were easily visible and poked seductively at the covering.
Gerald opened the last bag and produced a pair of red high-heeled shoes. He knelt in front of me and put them on my feet. It felt as though I was standing on tiptoe but they fitted me perfectly. He slipped the robe back on me and without doing it up, helped me over to the mirror.
I had truly never seen anything so exciting. The girlie that gazed back at me was stunning. The high heels accentuated the length and shape of my legs and the stockings and suspenders drew my eyes straight to the vee of my panties. My cock was bulging obscenely against the front panel. My hard nipples were clearly visible through the bra and as I looked up, a face that was almost unrecognisable looked back. The make-up and the hair bore no resemblance to the male me. I was looking at a beautiful slut, dressed to kill and dressed for sex.
Gerald stood behind me and my heels made me tall enough to feel his erection pressing against my rear cheeks. I was so horny that a part of me wanted to drop my panties, bend over and beg him to fuck me. I could imagine his hard male rod ramming into me while I rested my hands on my knees and thrust back at him. Another part of me though wanted to prolong the suspense. In the end I reached up and back with my hands and half twisting, pulled his lips down to mine.
"Thank you," I said, "thank you".
He clasped my breasts and nuzzled into my neck.
"No," he said, "thank you. You're perfect, better than I ever dared hope. I've waited for someone like you for so long, I'd almost given up hope".
I turned fully round and pressed myself against him grinding my satin-covered hardness into his crotch.
This time it was me that whispered seductively in to his ear.
"Do you want me now?"
"There isn't time...dinner..."
I was fondling his hard cock through his trousers.
"You do, don't you?"
I knew I had the better of him and unzipped his flies before edging my hand in and seeking out his bulge.
"Wouldn't you like to be in my mouth now?" I whispered as I undid his belt and tugged his trousers down.
"Wouldn't you like to fill my mouth with your beautiful cum?" I pulled his underpants over his swollen knob and down over his shaft.
"Shall I lick it for you, just a bit?"
In answer he gripped my head in his hands and thrust his cock between my lips.
"Oh yes, my darling, suck me, make me cum".
Almost immediately he started thrusting into my mouth. I held on to his legs and allowed him fuck my face, wrapping my lips as tightly as I could around him. Each time he pulled back, I used my tongue to flick across his pee hole and as he pushed back in I pressed my tongue up as hard as I could against the underside of his cock.