Halloween - Cover

Halloween

Copyright© 2006 by NickB

Chapter 4

Erotica Sex Story: Chapter 4 - The Halloween party is here again and as usual, Chris hasn't got a costume. He asks his wife to help and is not prepared for what ensues...

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   CrossDressing   Halloween   Slow  

Jess snuggled up to Chris hearing his breathing change as he drifted off to sleep.

It was a sticky situation, no doubt about it. She had jumped on the situation without a thought for what it would do. She thought it was just a bit of fun. She knew he enjoyed it, but she never once considered that it would ever be anything more than that.

The fates, situation, whatever, conspired to make it more involved, more difficult than a bit of fun. She really hadn't meant to forget the solvent and was probably a bit harsh expecting him to go to work in the guise of a woman. She hadn't realised the implications of these actions, the ramifications with regards to the up coming meeting and what influence that would have on him.

He had gone through with it only because the company needed him to and then had wound up deeper in it when he was held over a barrel with the customer wanting to deal with Pippa rather than being passed onto others who may not have the knowledge and the feel that she had.

She felt terrible for taking advantage of the situation. She had indulged a fantasy with Chris, playing with his breasts, pretending he was a woman, feeling the soft, smooth skin, clad in nylon, being turned on by the thought that underneath it all was her man, but what was left of that man and how long could he continue to be one all the time she was treating him like he was anything but that man?

Pippa was different. As much as she didn't want to admit it, he was right and she got on much better with Pippa than Chris, especially where the sex was concerned. She didn't know what it was about how Chris did things as opposed to how Pippa did them; it was just that with Pippa, she got the best of both worlds, getting sex with both a man and a woman without having to cheat on her man to do it.

Chris's admission that he was starting to get lost in the whole fantasy/reality situation was something that now she came to think about it, was probably inevitable the way things were going. He was showing more than a healthy interest in being treated as, as well as acting the part of a woman and Jess knew that she wasn't doing anything to discourage that, in fact it would be true to say that she was actively encouraging it.

This was a definite turning point. It seemed that while Chris was willing to make the sacrifice to fulfil the requirements of the customer with regards to being Pippa, it was having a confusing effect on him. For her part, she was probably willing to go back to the way things were, but she had to admit that it wasn't nearly as much fun.

Jess's head was becoming crowded with all the things going on, but after more or less facing the fact that she was going to have to accept that while it was fun while it lasted, Chris was going to have to make the decision of what to do about Pippa. She hoped that Pippa would stay, but whatever happened, she didn't want to give Chris up even if he wound up as Pippa with only overtones of Chris remaining.


Monday morning, Chris got up and felt like a weight had been lifted from his shoulders.

The issues had not gone away, but he now felt that now that Jess understood that he was nervous and scared of what was going to happen, he didn't feel so alone in those fears.

Jess was still asleep and he dressed in a jumper and skirt, brushing out the wig in front of the mirror in the bathroom after he'd had a shave and applied moisturiser, ready to apply makeup himself for the first time.

When he'd finished, he was satisfied that Coco wasn't staring back at him and he went downstairs to make a couple of cups of tea.

He returned to the bedroom and placed the tea on the bedside table.

"Jess?" he said shaking his wife gently.

"Huh?" she said sleepily. "Morning gorgeous." she said, pulling his head towards her and kissing him soundly on the lips, snaking her tongue into his mouth and grinning wickedly when he stood up.

"Now, now, there's no time for that. It's time to get up."

"Spoilsport!"


He got to work and was surprised how many people actually greeted Pippa, saying how nice it was to see her again and it set his mind to wondering just what he'd been like before. He got to know more of the staff as Pippa than he ever did as Chris and by Wednesday, he was sure that there were fewer people there that he didn't know than those he did.

Wendy appeared shortly after his arrival.

"I didn't think you'd be staying." she said.

"Yes. Chris is going to be away for a while longer yet." he replied.

"So you don't mind coming to work like that?"

"Come in Wendy and close the door." he asked. She had a slight smile on her face and sat in front of Chris. "You know?"

"What? You think I'm blind?"

"The others?"

"I don't think some people pay attention, but mostly, yes."

"Alright. Do you know why I'm doing this?"

"Yes."

"How did you find out?"

"I could already see what was going on, but Jamie confirmed it."

"What?!" Chris was gob smacked. "Why didn't you tell me?"

"I like you better like that. You're easier to get on with."

"I don't believe this."

"I shouldn't worry about it. I don't think anyone's going to give you any stick about it.

You're the boss after all."

"If you knew, do you think Bill will have spotted it too?"

"Probably."

"Oh God, I'm doomed. We're all doomed."

He felt as though the world had just dropped out of his bottom (sorry, I think that SHOULD have been the other way round). He thought that no-one noticed and took his explanation that he was his sister, but it appears that he couldn't see the wood for the trees. His whole plan had backfired.

For the rest of the day, he stayed in his office. He had plenty of work to be getting on with and had little or no reason to speak to anyone outside. He just couldn't wait to get home. He waited until everyone else had gone before he left the office.

He was rolling drunk by the time Jess got home, sitting in his dressing gown, wig askew and needless to say, she was angry before she even knew what had happened.

"What the fuck's going on?" she hissed.

"I's had a bit of a jink." he said, one eye in the pot and the other up the chimney.

"I can see that. Why."

"Why not?" he said, raising his glass. She took the glass away from him and put it on the side.

"What happened?" she said with that tone that implied that she knew something had happened and doubtless she wasn't going to like it.

"They know."

"Who knows what?"

"Know I's Chris."

"Oh shit."

"'S funny. Thash what I said."

"What's going to happen?"

"I sink I's goin' a burp." he said, belching loudly, then keeled over sideways and proceeded to snore almost immediately.

"Oh bugger." said Jess.

It was about eight when he resurfaced, head pounding like Neal Peart's kick drum. The wig hair was plastered over his damp face; ironic, since only a short time before, he was the one that was plastered. Jess was on the phone and it sounded like it was to Jamie. She wasn't happy and by the tone of the conversation, neither was Jamie.

Chris couldn't listen anymore, not that he could hear much. He could only hear what Jess was saying to Jamie about the state he was currently in. Anyway, he had other more pressing things to do, like calling God on the great white telephone.

He arrived back downstairs looking extremely green and dishevelled.

"How are you feeling honey?"

"Like someone else has been using my brain and not put it back right."

"It doesn't solve anything, you know, drinking."

"Thanks. I'll bear that in mind."

"Jamie told me all about it."

"So what happened?"

"Seems they all know and why too, more or less."

"Yes. I got that from Wendy. I feel like crap."

"I told you drinking wouldn't solve anything."

"Not from the drinking; from work."

"It's not over yet. You don't know what's going to happen there do you."

"No, but if everyone at work could see through the disguise, then it's likely that Bill did too and I don't think it's going to sit too well."

"Try not to think about it yet. Let's go to bed and perhaps you can sort it out in the morning."


The next day, Chris was up at the crack of dawn using the solvent to remove the breasts from his chest and getting ready for work. When Jess joined him downstairs, he was in a business suit and looking like Pippa never happened.

"Don't worry, Chris. Just take it as it comes." she said. He smiled back at her wanly.

He arrived at work and went to his office. Some time later, a very shamefaced Jamie entered his office.

"I know you're not happy with me, but it looked like so many already knew something was going on, I felt it was their right to know what it was."

"I know. I was angry yesterday, but today I'm not. I was silly to think that I could pull the wool over everyone's eyes. I must have looked stupid."

"No. I didn't know it was you until you said who you were, or that you were anything other than female. I think here was just too close to home perhaps. Maybe Bill won't have guessed."

"I'm putting Bill straight today."

"Don't. If we lose the contract, we lose the contract, but don't go putting your foot in it any further than it already is. Some of the people that have spoken to me, feel that if you've got to go to those lengths, then it isn't worth it."

"Yes, but do they know their jobs are at stake if we don't get this contract?"

"Er, no. I was a little selective about how much I told them."

"Probably wise."

No-one said anything about seeing the boss there as the boss and the rest of the day passed as though nothing had ever happened. Chris went home no lighter across the shoulders than he arrived. He was hoping to find out one way or the other, but obviously, SolTech were at liberty to consider all their options for as long as they wanted and anyway, Millennium had failed to get contracts before, what was the difference with this one?

They desperately needed it. That was the difference.

There was more on Chris's mind than the possibility of losing the contract for whatever reason. The fact was, that despite the short period of time he had been Pippa, he missed her, or rather missed being her.

The morning had been almost solemn between him and Jess and he rued that. He missed the closeness Jess had with Pippa already, missed the fact that they told each other things that they didn't as Chris and Jess and they shared so much more that wasn't said.

It felt like from the moment he expressed his feelings to Jess, everything changed. He probably didn't do the situation with his getting rat-arsed any favours, but it felt appropriate somehow although afterwards, he wished he hadn't. He knew that Jess felt at least partially responsible for the fix he found himself in and she was probably feeling just as bad as he was.

The rest of the week went steadily down hill from that point. He was so wrapped up in his own problems that he failed to see that Jess was having a bad time too. She was hoping that he would be able to pull himself together, hoping that he would be able to draw from his experience as Pippa and bring that into his male self, although she didn't know how that would work.

It was only a few days but it felt like an eternity. It was so difficult being with someone, but not at the same time. It seemed as though in taking off the breast forms, Chris also took off Pippa and not a trace of her remained. Sleeping with Chris didn't even feel the same anymore.

Chris was having the same issues. He had taken off the clothes and the falsies and with them went the personality. He tried to be what he thought was the same with Jess, but it just didn't work. The snappy comments came out as though they were delivered with a machete in stead of a wry smile and he didn't know how he could change that.

They say that clothes maketh the man, but in this case they were right. Well it made the girl, so they were nearly right.

By Thursday, Jess and Chris weren't even speaking to one another. Being close in bed was a complete joke. They were both using mental guy ropes to keep from falling off the respective edges of the bed, leaving a space about the size of a football pitch in between them. Neither of them knew why and neither of them had the nerve to ask.

Friday morning, they didn't speak and he went into the office feeling like the last man alive. He felt lonelier now than he had ever done in his life. After his outpouring of emotion and admissions the other night, he felt that he had pushed Jess away. He knew she liked him as Pippa. He guessed that if she could keep her instead of him, she would and it hurt. The fact that the two people were one and the same (well, sort of), didn't figure for either of them.

It was like the way an actor can turn on the personality of someone else for a part and not even think about how they do it, but then afterwards, they take off the costume and the character disappears with it. Even if they can get the voice or the look, the costume does more to them than cover them with a disguise; it implants the character deep into the soul of the actor, making it believable. Who would have thought that Han Solo could be played by a man who when off the set could be the complete opposite to the character he was playing on it. It's the costume.

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