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(C) 2006 Nick B All rights reserved

Chapter 3

The next day, Chris woke to find the bed beside him empty. He sat up and let his eyes become accustomed to the light. He’d not been there for long before Jess came in.

"So you finally decided to join us?"

"I was tired."

"Well don’t lie there all morning, we’ve got shopping to do."

"Shopping?"

"Look, I’m willing to admit that I got you into this mess, but I’m not prepared to let you ruin all my clothes getting you back out of it."

"I'm sorry. I hadn’t thought about that."

"I didn’t think so. I wonder how you keep that company going without a thought invading your head."

"Luck and charm, I guess Jess!" She poked her tongue out at him.

"Just get up! I’ve put you out some stuff for the trip." she said.

Once breakfast was over with, Chris sat in a short denim skirt (above the knee anyway) and a t-shirt that came to just above the navel. Again, he wore the ankle boots and wig, but had made a choice that shoes were going to be on the list as he didn’t think the boots were appropriate for all occasions. Of course Jess didn’t see fit to point out that he would happily wear the same shoes for months or even until they wore out completely in his masculine guise.

"If I’m going out like this, you’ll have to pay and we’ll sort the finances out afterwards."

"What’s wrong with yours?"

"It says here "Mr C Burton". Don’t you think that might be a problem?"

"Ah. Fair do’s."

The first shop they went into was for what Jess termed as the staples. The thought of little bits of bent wire amused Chris, but he kept it to himself. Now staples were work panties, tights, and bras. The panties were generally simple and could be any colour, providing they weren’t visible through the material of the outerwear. One pack of colourful panties was bought, along with a pack of white ones.

Next were tights, which was simple, being a ‘one size fits all’ kind of affair and were bought in tan and black.

Thirdly came the bras and sports bras according to Jess were best for work. They weren’t so obvious through semi-transparent blouses and were above all, supportive and comfortable. Chris tried one on and agreed. On and off over the head and no stiff bits to pinch.

It only seemed fair that Jess should have some new bits and pieces too and Chris nearly had heart failure when it was all totted up, but Jess paid it and Chris had to keep the good of the project in the forefront of his mind as they wandered on to the next shop for some outerwear.

"You’ll need a couple of suits like mine, some skirts, blouses, jumpers [sweaters], cardies and we’ll steer clear of trousers."

"Why?"

"Well, unless we get you one of those gaff things, however well you think you’ve hidden your bits, they’ll be noticeable. Plus you’re not really the right shape."

"What’s a gaff?"

"Panty type things, to keep you flat in the nether regions." Chris blushed.

"Like a girdle you mean?"

"That sort of thing only thinner and it’s designed to hide thingies. For now though, stick to skirts."

A number of skirts were bought and it angered Chris to think that he bought four skirts for the same price as one pair of his trousers (which didn’t even fit that well). Anyway, he nearly had another coronary when along with some more stuff for Jess (of course) the cost was measured in astrological terms as far as he was concerned.

Next came cosmetics and that very nearly gave him a nervous breakdown. There was exfoliating cream, foundation, blush, eye liner, mascara, lipstick, lip gloss, pads for removal and moisturiser for before and after, brushes for application, hair gel, mousse, tools, such as tweezers, nail files and buffers, nail conditioner, nail polish remover and several colours of polish and that was just to get him started.

It didn’t stop there though. Jess had stopped at the perfume counter and was spraying various different scents around and sniffing.

"Try this." she said. Chris sniffed the air, but could discern one from the others she had sprayed. She sprayed the smallest amount on the underside of his wrist and told him to rub it on his other. He rubbed and sniffed (like scratch and sniff, only softer). It was a spicy, flowery scent that he found most intoxicating.

"You like?" she asked.

"Yes I think it suits you."

"It’s not for me, idiot, it’s for you."

"Me?"

"Of course! Don’t you want to smell nice as well as look nice?"

"Well, I suppose, but I’ve got stuff for that at home."

"You have underarm spray and some Paco Rabanne, neither of which is particularly appropriate for a woman."

"But I’m not a …" he stopped short as the fact he was wearing a skirt, stiletto-heeled ankle boots, a bobbed wig and breasts hit him in the soft bits. "Ah!"

"Exactly!" she said nodding and the perfume joined the other purchases.

He was as white as a sheet when he left and was struggling with most of the baggage too.

They visited a couple more shops on the way to get some shoes, apparently to get some ‘weekend wear’ as Jess put it. Once in the shop, he knew exactly what she meant. He actually had to handle the goods and he spent the next half hour or so in an almost constant flush, suffering an aching groin!

On the way to the shoe shop, Jess had Chris go into a jeweller’s to get his ears pierced.

"Isn’t this going a bit far?"

"Not if you want to look the part."

"I do, but I didn’t think that extended to poking holes in me."

"Trust me it won’t hurt and you’ll be out in no time." Out of earshot, Jess spoke to the girl behind the counter and asked whether the navel could be pierced too while he was there. There didn’t seem to be a problem and within five minutes, Chris had three holes two of which were filled with small gold studs with aquamarine inserts (his birthstone) and one crescent-shaped stud through his navel, which he wasn’t expecting and was actually quite angry about. When he stood up however, he had to concede that it did look in keeping with the image he was trying to portray, though just how many times he was going to expose his midriff at work hadn’t crossed his mind.

Shoes next and he had just about had it. He was well and truly knackered [tired out, all in]. It was all he could do to summon up the enthusiasm to go in to the shop at all and then when he saw the plethora of styles, colours, heel-heights, boots, shoes, sandals, mules and Lord alone knows what else, he didn’t know whether he could be bothered.

"It’s so much easier buying men’s shoes." he said. "There are only about a dozen to choose from and two-thirds of those are brown."

Three pairs of shoes (one pair with nearly four-inch heels), one pair of sandals with a somewhat more modest heel and one pair of knee-length boots later (not to mention Jess's 'extras'), they left the shop, but this time, the goods were a little more evenly distributed between them.

They got home and Chris was all in. He flopped on the sofa and gasped.

"You did really well." said Jess encouragingly. "You got some real bargains."

"Doesn’t feel like it." he grumbled. "It cost a bloody fortune and my belly-button’s sore."

"Yes, but now you’re set for most any occasion aren’t you?"

"And more besides, probably. I need a drink."

"Oh don’t be so stuffy. I want to see what you look like in some of your new things."

"Must I?"

"It is customary." she said and dragged him upstairs to the bedroom, telling him to bring his bags along too.

He’d never played ‘dress-up’ like this before and with the exception of the party costume (over which he had little or no control) the things he’d done over the last three days, were kind-of out of necessity. He had no time to actually enjoy what he was doing, always keeping the objective in view, not the journey to it.

He watched transfixed while Jess emptied the bags of his new purchases onto the bed, not stopping her running commentary as she picked up blouses or cardigans and expressing her opinion as to what she thought that would go with what.

"Here." she said. "Put these on and let’s have a look."

He took off his clothes down to his underwear and slipped the skirt she handed him on, followed by a roll-neck cotton knitted jumper.

He liked the feel; liked the freedom around the legs and the way it flared slightly. He twirled and Jess smiled.

He WAS getting the hang of this, she thought.

They spent the rest of the afternoon and up till about seven in the evening playing ‘dress-up’. This consisted of both of them taking it in turns to try on a new outfit. Now and outfit, is a collection of clothes. Whether they were bought to go with one another is beside the point, so there was a lot of pulling off and putting on and some things were put on again and again depending upon the other stuff that was there to go with it.

Chris had to admit that this was something very new for him. For a start, he'd never had so many new clothes at once and only ever thought of his clothes as either work or best. Crappy stuff for gardening or doing work on the car didn't count. It was something to do with the position he held on the corporate ladder. Many men get it when they reach the giddy heights of directorship and employ staff. It seems that their dress sense dribbles out of their ears and they become blind to fashionable clothing, heading instead straight to the suits and Farrah trousers!

The 'dressing up' continued a-pace and culminated at about six, with a display of Chris’s new weekend wear, the last being something he didn’t even know was there. Chris had no idea how she did it, but Jess had managed to buy a few things he didn’t see probably while he was otherwise engaged. It was a red and black half-cup bra and panty set with a suspender belt that doubled as a waist cincher, but the panties and bra were sheer aside from some red detailing in places other than where it would hide anything, making everything inside perfectly visible.

He picked them up and could feel his ‘interests’ rising. He was actually trembling as he looked at his very smug-looking wife.

"Wow!" he croaked.

"I got you these to go with." she said looking even more pleased with herself and handing some stockings to him, telling him to be careful when he put them on.

"I’ll put them on in the bathroom then come in. That way it’ll be more of a surprise."

"Oh goody!" she chirped, bouncing up and down clapping her hands together. "I LOVE surprises."

He disappeared before his trembling turned into the shakes and sat on the toilet to put his new lingerie on and despite his trembling, he was okay with the bra, which incidentally, WAS as sheer as the panties and though it covered the nipples (just barely), they were perfectly visible.

He sucked in his tummy, pulled on the suspenders and did them up, all the while, more ‘interest’ was being shown which would make getting the panties on with all of him inside them, without them looking like a tent, nearly impossible.

He pondered that for a moment, trying hard to think of things like ‘lead time’ or ‘programme procedures’ or ‘Classes and functions’, perhaps changing a wheel on the car, but all of it was useless, his manhood was actually winking at him as it swayed and throbbed in time with his heartbeat.

What was he to do?

"Er, Jess?" he called.

"Trouble?"

"Well not exactly…" he said, but she was there at the door before he could finish.

"We need to do something about that. It’ll never fit in those." she said, "But can’t you put the stockings on first, she said picking them up and pulling one out to its full length, displaying the fact it was a fishnet. With more of a sensory overload, his thing was actually getting painful and he fervently wished that she hadn’t picked up that stocking.

"I don’t think I can wait that long." he said blushing beetroot.

"Ah!" she said understanding completely and started running her hands softly down the length of his iron-hard tool as his head started to swim and his legs went to mush.

Seconds later, he had dropped to his knees, his shoulders shaking, his breathing ragged. Jess’s eyes went very wide indeed as she had to quickly move to one side, while moving ‘it’ to one side too for obvious reasons.

"Wow. That was fairly immediate." she said as she wiped the floor. Chris coughed uncomfortably and started to giggle, setting Jess off in the process. He shoed Jess out of the bathroom so that he could finish with his ‘surprise’.

"You mean it gets more surprising than that?"

"Possibly not, but…" he said shrugging and pushing her out of the bathroom.

A few minutes later, he entered the bedroom.

"Oh my." she said as he advanced, taking her in his arms and kissing her. She ran her hands up and down his stocking-clad leg, up past the panties, feeling the silky texture of the bra and the cheeky way the nipples stood proud through the translucent material.

She stroked across his tummy, tracing around and over the little piercing that stood from his navel, her blood-pressure rising and her heart pounding out a beat that could be measured on the Richter scale!

He stroked Jess, sliding his hands under her jumper, feeling the satin of her new bra, sliding his hands down and into the top of her skirt, to find her thong, tracing round the tiny ‘V’ that protruded from the cleft of her buttocks, finally allowing his finger-tips to follow the narrow piece of material down between.

She gasped as she felt his fingers so tantalisingly close to her womanhood and she pushed him back onto the bed in amongst all the clothes that wound up being cast aside as they got down to the business at hand.

It surprised Chris that even so soon after having ‘finished’ on his knees in the bathroom, he was still able to regain the ‘interest’ and at seven, they looked awfully mussed and otherwise dishevelled as they descended the stairs to the lounge.

"That was a surprise!" she said.

"You’re not kidding." he replied and they sat on the sofa like a couple of giggling schoolgirls.

 

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Sunday, was a long and at times very tense lesson in makeup application, but by the end of it, he was definitely making progress. It was getting used to actually poking things almost into his eyes that gave him the most trouble and at times, he felt like throwing it all up in the air and walking away.

He needed to learn though. There was no guarantee that he wasn’t going to have to do this for some time and there was equally no guarantee that Jess was going to be there or able to do it for him everyday either.

He was only learning the basics of daytime wear currently. The more advanced evening look would have to be covered later and as and when there was more time.

"You have to do much of it by feel." she said as he was trying without much success, to squint out of the eye he was trying to put the shadow on.

"It’s impossible!" he exclaimed and tears started to leak from the corners of his eyes. "I’ll never get this."

"Yes you WILL!" she assured him.

"It’d be easier if I was a real woman." he said.

"Why?"

"Well, I’d have learned from an early age and this wouldn’t be necessary."

"That doesn’t mean it was any easier to learn though." He thought about that and had to concede that no, it probably wasn’t at that.

At the end of her lesson, Jess decided to give him a real sultry and vamp look, to go with his new lingerie, accentuating the makeup round his eyes and darkening his lips. At the end, she couldn’t resist planting a big kiss on them.

Chris responded and soon, what few clothes were being worn, were flying hither and thither as the two of them writhed and squirmed on the bed, Jess making a point of concentrating on his breasts again.

As if that was a hint, Chris paid attention to hers and all the time through, his head was the thought that maybe one day he would be able to experience what it was like to have his own breasts and not the rubber forms that were currently glued to his chest.

The thought scared him and he didn’t know whether that was a case of him getting caught up in the moment, or it was a real cry to take this whole cross dressing thing one stage further.

"Play it by ear" Jamie had said and that’s just what Chris planned to do. There was no sense in rushing anything as if he did decide to go ahead the procedure was likely to impact on more than just his breasts. He didn’t think from what he’d seen and experienced that there would be much in the way of opposition from Jess…

 

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He couldn’t sleep that night.

He had now had the party, the entire weekend and a day at work as a woman and the short space of time he had been en-femme, didn’t seem to upset him; far from it. He actually seemed to be fitting into the persona of Pippa and was having a whale of a time with the sex side of it.

He’d been shopping in a short denim skirt, which made him feel like one of the girls he would ogle, had his ears and his navel pierced (that was still a bit sore), bought more pairs of women’s footwear than he owned in men’s including his trainers and had almost as many women’s clothes as he had men’s, not to mention half a shops-worth of makeup.

It all seemed rather a lot since the project wasn’t actually finalised yet and he didn’t know whether all this was really necessary. All that aside, he was already contemplating breasts – real breasts and that would at least require hormone therapy and probably a very understanding doctor. On top of that, he was also turning over the thought of having his body hair zapped with a laser to save him having to shave or use that awful-smelling cream – all in less than a week!

He got up, put on his dressing gown and headed downstairs to the kitchen.

Jess joined him sometime later and asked what was wrong.

"I think I’m starting to lose myself."

"You’re here now."

"Yes, but which ‘me’."

"There’s only one."

"Ah, now that’s what I thought, but it seems that I was wrong."

"Huh?"

"Chris gets treated differently to Pippa."

"That’s because one’s a woman and one’s a company director."

"Not to you."

"I don’t treat you any differently whatever you look like."

"You didn’t ask Chris to play dress-up did you? You didn’t play with Chris’s nipples the way you play with Pippa’s did you? Would you have got Chris to get a navel piercing or pierced ears?" Jess looked a bit embarrassed.

"No." she said quietly.

"That’s what I thought." Tears started to roll from Chris’s eyes. "I really like the way I’m being treated at the moment. I like the way we are together when I’m Pippa and I don’t know whether I want it to stop, but it doesn’t end there."

"Why not?" Chris took a deep breath.

"Because, when I’m Pippa, I want to be Pippa and not a facsimile. I think about having my facial hair zapped by laser so I don’t have to shave again and admit that I have thought about the rest of my body in the same way. I think about having real breasts and about having a real woman’s body."

"Wow."

"Now the only way I can keep Chris real and Pippa fictitious is to keep the fact that at the moment it’s all novel (no pun intended); a bit like having a new toy, but sooner or later the novelty is going to wear off. By doing that, I know that sooner or later, I’m going to be plain old Chris again and it helps not to get too carried away. The problem of course is that the longer I’m Pippa, the further away Chris seems to get and the more I want Pippa’s personality and her body."

"There isn’t THAT much difference."

"There is; well, there’s enough difference to make you treat me differently."

"I didn’t realise. This is serious isn’t it?"

"Moderately so, yes. I may just be over-reacting, but I’m scared of losing the contract, of my staff hating me because I’m different and most of all, I’m scared to death of losing you."

"You won’t lose me. I won’t leave you, whoever you want to be."

"You might if Pippa took over completely. ‘She’ might want to go further than just breasts and want to be a whole woman."

"I see." she said, her brow furrowed in the thought of the seriousness of the matter. "Is that what you want?"

"No, but the longer I stay like this, the less I seem to see Chris in me. I can’t seem to help it. I see you having more fun with Pippa than with Chris, but I’m not sure it will last. That doesn’t stop me clinging to it while it IS there though. I definitely don’t want to lose you or what we have because of getting too involved with the fantasy."

"I don’t want to lose us either. Now come back to bed, I get lonely without you there."

 

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Continued in Chapter 4