tagTranssexuals & CrossdressersWhatever It Takes? Ch. 02

Whatever It Takes? Ch. 02


"Every thing all right?" Penny asked.

She was standing there wearing a baggy rugby shirt, loose fitting boot-cut jeans and a pair of timberland boots. She looked very sexy, even though her clothes were not particularly feminine. Then in stark contrast, there was me.

I was standing in her flat wearing a tight, fluffy pink v-necked sweater, over a fitted, white t-shirt and one of her sports bras stuffed with cotton wool balls and scrunched up tissues. On my bottom half, over knickers and tights, I wore a pair of her tight fitting blue jeans with brown mid-calf boots. To make a proper job of my transformation I had allowed Penny to apply a layer of foundation, a dab of eye shadow, a quick flick of mascara and some lipstick. As a finishing touch she had used heated curling tongs to get some shape into my hair.

She was now waiting for me to go out like this, with her, to a firework display! If I refused she would probably dump me on the spot. If I agreed I was letting myself in for a step into the unknown, followed by who knew what else.

Did I want to be with her that much? I thought for a moment and caught a glimpse of myself in the mirror. I was totally in love with her, I did like what I saw in the mirror and I did like how I felt...

"Everything's fine Penny, lets go!" I said much more confidently than I felt. Soon we had left the safety of the flat and were walking, arm in arm, along the street. We were just chatting about things, but the time allowed me to do two things; to get used to her calling me 'Daniella' and for me to get used to talking in as feminine a voice as possible. Luckily I've got a fairly high tenor voice anyway, so not much effort was needed!

I was too nervous to remember much about the evening, just a few bits and pieces really. My fear of being out-ed as a man in drag proved groundless. I was convincing enough not to be noticed in the crowd. No small children ran up shouting 'it's a man' as they were all too busy looking at the fireworks or eating sticky candy floss. The guy taking the admission money told us to 'have a good time girls!' Unlike many stories about cross-dressing that I've read since, I didn't prove irresistible to every man I passed -- no one seemed to notice me, probably as I was next to the beautiful Penny. Not that their indifference was a problem; I was glad!

I had never seen Penny so happy or animated. She clearly loved the whole experience as much as I did. Half-way through the evening there was a break in the display.

"Do you want to go home now?" Penny asked.

I took both her hands, squeezed them tightly saying "Why would I want to leave when we're having such fun?" My reply delighted her. When we finally left, arm in arm, I walked along as if floating on a cloud, I felt so happy. We hadn't even closed the door of her flat, before Penny took control, pushing me against the wall; she kissed me passionately, virtually tearing off her own clothes in the process. I tried to undress too, but she stopped me; I realised that she wanted me to stay in my feminine attire and was happy to oblige.

We kissed and I began to fondle her, sliding my hand between her legs -- I had never felt her so wet or so open. I teased her clit with my thumb and plunged my fingers deep inside her. She pushed so hard against me she nearly sprained my wrist! Eventually she removed my jeans, it seemed appropriate to let her take the initiative, slid my tights down, but only far enough to allow her to slip my cock out the leg of my panties. With Penny on top and so aroused I thought she might cum first. She didn't, so she moved up to allow me to lick her, the taste of my cum mingling with her juices, until her climax.

We showered and got ready for bed. I decided to keep up my new role and asked Penny if she had a nightdress I could borrow. Again she seemed delighted and lent me a red baby-doll, with matching panties. She wore a longer white silk nightdress and we fell asleep cuddled up together.

The next morning I awoke to find her gone, leaving a note. "Had to go into work -- back about 2 -- love u x". I had an idea. In a rush I got dressed in the same jumper and jeans outfit, bra, tights and all. As I did I surfed the web on my mobile, planning my morning. Carefully I put on some foundation onto my freshly shaven face, a bit of eye shadow and some pink lippy. I didn't look great, but I'd do for now. As I walked to the high street, I felt very exposed; out, en femme, in the daylight and alone, but once again I was ignored. I got cash from a cashpoint, then went and bought myself a handbag to carry all the stuff that didn't fit in the pockets of the tight jeans. Checking the address I wanted one more time, I hailed a taxi and set off on my shopping spree.

The taxi dropped me off and I went into an ordinary looking shop, but inside it was an Aladdin's cave of wonderful items. Plucking up my courage I approached the shop assistant. She was taller than me and a few pounds heavier. She turned and asked "Hello 'hunny', what can I do for you?" in a deep but quite sexy voice. Her make up was thick and rather over the top and then I realised; like me she was a he. This put me at ease, and I explained that I was just starting out as a transvestite and needed some false boobs. "Quite big ones" I added, blushing at my own forwardness. Delores, the shop assistant, persuaded me to try a C-cup as well, rather than the D-cup I tried first. Well they were both fabulous, made of the same silicone as implants, but in a durable flesh-coloured coating. In the bra that she also recommended I walked about the shop, revelling in the feel of bouncing boobs! She was right too about the smaller size, with my slim build the D-cup was just too much. I bought the boobs, two bras, (one white, the other black) and pairs of matching knickers. I would have loved to stay longer and chat, but I was on a schedule. Like a kid with a new toy I insisted on wearing the boobs and the white bra right away. We hugged as I left and Delores gave me her mobile number 'in case I ever wanted to go for a drink or something'. Blushing I left and headed, by bus, for a nearby chain store.

I had seen an outfit on their website I thought might suit me. It was a black blouse and waistcoat, worn with a short red skirt, opaque black tights and black high-heeled boots. I quickly selected the items and bought them without trying them on, hoping that they would fit! Next I nipped into a chemist and stocked up on make-up. I'd made a list of all of the stuff Penny used on me last night. The girl at the checkout looked at me a bit too closely for my liking and I realised how odd it must have looked buying all of the items in one go! To be honest I was already beginning to get a bit nervous; my make up wasn't holding up well and I started to feel conspicuous. I hailed another taxi, gave him my address and sank back, relieved into the seat.

On the way I got a text from Penny; she was home and had expected me to be there. I had lost track of time and was now late. There was no time to go home to change, so I redirected the taxi driver to Penny's.

I let myself in. Penny turned and gave a classic double take as she saw what I was wearing and then noticed the effect of the boobs! I told her about my shopping spree. She started to cry.

"What's the matter Penny; don't you want me to dress like this?"

"No," she sniffed, "It's that you're so beautiful and that you'd do this all for me!"

I pointed out that I was doing it for myself too. We hugged in a timeless embrace.

I changed into my new outfit and Penny helped me fix my hair and make-up. We headed out for a shopping spree at a nearby mall. Penny was set on buying me things to match my new persona and I couldn't stop her all of the time. In a jewellery shop she insisted on buying me a watch and then she arranged for me to have my ears pierced!

I was admiring my beautiful new earrings, simple small hoops, in my newly pierced ears when I realised that the girl had said I needed to keep them in for six weeks to stop the holes healing over.

"Penny, I'm back at work on Monday. I can't wear them to work!" I wailed.

"Daniella, we'll worry about that on Monday; let's enjoy the weekend first."

Then she insisted that I had my hair styled. Again I protested that it was not a good idea; with the earrings and a new feminine hairstyle I'd be a laughing stock. She wasn't happy, and for a while it looked as if we'd have a row. Instead for half an hour I got the silent treatment. I convinced myself that it'd be okay. So long as I could pull it back into a pony tail as usual no-one would notice. I told Penny I'd changed my mind. It worked; she regained her smile and bounce in her step.

There was a hairdressers in the mall and they had appointment's available. I sat bemused as Penny and the stylist discussed what style I'd look good with. Her story was that I was her friend who needed a make-over and needed serious advice. To cut a long story short I ended up with a stylish bob, with blonde highlights. My first reaction was delight; I looked great with my new look. Then reality struck; there was no way I could pass it off as a male haircut. I could have been upset but Penny's happiness and positivity were infectious. Monday was a day and a half away; enjoy the moment, carpe diem and all that.

Penny insisted on us having lunch at a trendy bistro in the mall. The Italian waiter was overly attentive to us, using cheesy lines like, 'hello beautiful ladies'. He soon lost interest when Penny leaned across the table and said 'kiss me now, Daniella'. We kissed and an old couple at the neighbouring table muttered something disapproving about 'lesbians kissing in public'.

Penny was so happy. We finished our meal, paid the bill and embarked on more shopping. I tried loads of stuff on. In every store Penny would try to sneak into the changing room with me. It worked once and we kissed passionately until the assistant knocked on the door, asking if everything was alright. We bought that dress and a couple of other things. Just before heading for home, Penny said we needed to loo.

"We? I'm okay."

"We both need to go," she insisted.

On the way in we passed someone leaving but inside the toilet was empty. Suddenly Penny took my hand and dragged me into a cubicle with her. Putting our bags on the shelf at the back she took off her skirt, folded it neatly and placed it on the bags. She took her panties off, throwing them casually on top of her skirt. I followed suit taking off my skirt. She pulled my tights down just far enough to reveal my knickers. I sighed with pleasure as she stroked my hardening cock through the silky material. Then she slipped it out through the leg and pushed me back to sit on the toilet seat lid. Facing away from me she carefully lowered herself onto my erect penis.

She was so wet I slid in easily as she virtually bounced up and down whilst rubbing her clit with one hand. It was so intense, so raw and passionate I came, squirting my cum into her; seconds later she made herself climax and I felt her pussy muscles spasm around my softening erection.

Then she stood up, wiped herself, and redressed. I did the same, tucking my cock back between my legs, adjusting my panties and pulling up my tights, before putting the skirt on. Redressed, Penny kissed me again, then we left the cubicle. The woman from the restaurant saw us.

"You young girls have no shame," she scolded. "Freaks!" she shouted after us as we hurried to the car park to leave.

Back at Penny's I modelled my purchases, to her general approval.

"You've chosen some great stuff. Your legs are fab, so short skirts are a must and those false boobs give you a lovely curvy shape. Daniella, you are stunning!"

That evening we made love again. I kept on my bra, with falsies, and knickers; Penny stripped naked. I admired her magnificent body -- she was truly stunning. It was a privilege to be able to worship at the altar of her beauty. Again the sight of my feminised appearance had made Penny wet. Gleefully I licked her pussy, before I lay back and she positioned herself on top of me. Again she rode me as if possessed, every second was precious. This time she didn't orgasm when I did. She moved onto her back and once more I licked her clean of both pussy juice and my own cum. We slept well after that.

Sunday was like one of those scenes from a cliché-ridden, made-for-TV love story. We walked in the park, we fed the ducks, we went to an art gallery and mimicked the poses. I had never been happier; Penny seemed elated too.

Evening arrived. It was time to face up to Monday and a return to work. Penny took the bull by the horns as she opened our second bottle of wine.

"Did you enjoy this weekend?"

"Yes, obviously."

"Did you enjoy the chance to be Daniella all the time?"

"Yes, more than I expected," I replied honestly.

"There's one question though; are you doing this just for me or do you enjoy it for yourself too?"

I thought carefully. Pleasing her was a big part of my motivation; after all until I met her I'd never dreamt of wearing panties, let alone going out dressed as a woman. Now I had started, I had to admit I was enjoying myself. Penny listened intently as I told her this.

"It's settled then. What would you say if I told you there was a way you could spend more time with me and spend all the time as Daniella?"

I assumed it was the wine talking.

"I think that would be brilliant," I said knowing that would please her.

"That's sorted then," she announced, "I'll make some calls on first thing tomorrow."

She would say no more except to say I'd find out on Monday.

I wondered just what I'd let myself in for.

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