A Christmas Party - part 2


Bob gets invited to his office's Christmas Party. His colleagues convince him that life is more fun in a dress.

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Christmas party 2
When we got to Cathy's house we got out of the taxi like the genteel young ladies that we were. Which is to say, we woke the entire street with our shrieks of laughter and drunken giggling.
It took Fiona and Cathy a couple of minutes working together to get the door unlocked. Jordan was clamping her legs together with crossed ankles by the time they finished and she pushed past everyone else with a heartfelt cry of “I need the loo, so bad!”
I don't know how she knew where to go but the door had hardly closed and I'm sure there wasn't time to lock it before the tinkling sound started.

On hearing the sound all four of the remaining girls looked at each other with the dawning realisation that they too, desperately needed the loo. Bags were dropped, belts were loosened and there was some half-hearted and quite careful jostling for position at the door. Cathy apparently decided she didn't need to go so badly that she was prepared to fight everyone else, or maybe she was just playing the good host, but she wandered off muttering something about “putting the kettle on”.
I wandered into the kitchen with her and soon we were organising cups, milk and a teapot on a tray.

“What about coffee?” I asked.
“Hmm, I hadn't thought of that. I know most of us will want tea, you might want to ask your girlfriend”.
“Girlfriend!?”
“That Jordan girl?”
“Oh, her…girlfriend?”
“Well I guess she might just be keeping tabs on her dress, but she seemed very friendly in the shower with you?”
“Oh” I was blushing, in the skimpy dress it felt like every square centimetre of skin was pink now. “We… . yes, I guess I have a girlfriend now?”
“I guess you do. Although, it's strange, she didn't seem that interested until she saw you in her dress…”
Jordan chose that moment to walk through the kitchen door.

“Were my ears burning?” Jordan asked brightly.
“I guess they were” admitted Cathy “We were trying to figure out your intentions with young Bobbi here.” She pointed at me.

Jordan walked over to put a possessive arm around my waist as she learnt against the worktop next to me. It might sound strange but it only struck me as she crossed kitchen that she was wearing my suit jacket, but she didn't have my suit trousers on.

“Mmmm, 'intentions’, eh?” She looked at me like I was a bowl of chocolate ice-cream. “So many possibilities” she grinned and turned to Cathy “you know, I've never had any cause to question my sexuality, at all, until I saw Bobbi in that dress. Now I find it hard to think of anything else. Such a delicious surprise in such a yummy little package!”

Jordan's obvious interest in me was surprising and made me a little uncomfortable, even if it hadn't been for my constrained plumbing.
Cathy turned to me and said, with some concern in her voice, “It looks like the ball is in your court, Bobbi, how do you want to proceed?”
“Proceed?” I was worried, it felt like I was standing on the edge of a precipice and I wasn't clear what we were talking about. It seemed like a good time to change the subject. “Er… Jordan, where are my trousers?”

Cathy lost it completely.

She barked out a laugh like the braying of a donkey.

Jordan looked at her with a gentle smile.
When Cathy finally paused for breath Jordan said “It's fine, I left them with Julie, we can get them next week when Julie is back in the hotel. They didn't really fit me right and I feel better in a dress”.
She opened my jacket to reveal a black dress with tiny spaghetti straps and a plunging neckline that was completely covered when she had had the jacket done up, she left the jacket open now.

“Where did you get that dress?” Cathy asked.
“It was in Julie's box of dress up clothes, I had a rummage while you were doing her make-up”.
Becky came in then.

“Nice dress” she mumbled, I'm not sure if it was aimed at me or Jordan. “Any chance of that cuppa, Cathy?” She continued in a clearer voice “I'm that parched”.
“Coming up” Cathy said “we were just trying to figure out whether Bobbi has a girlfriend, or trousers, for that matter”.
“Ooh, could I have a coffee?” Jordan asked.
“Me too?” I said.
“Heathens” said Cathy, “there's instant in the cupboard there.” She pointed above our heads.
“Instant!” Jordan said indignantly, “and she calls us 'heathens’!”
Nevertheless she started taking the coffee jar down and making us both coffee.

Jordan looked at me and asked “How do you take it, sweetie?”
“Huh?” I answered, I was having trouble concentrating with the full intensity of her charisma focussed on me, especially now her cleavage revealing dress was unleashed from my jacket.
“She means your coffee, silly” Cathy hissed at me, she answered for me “Bobbi likes it sweet and creamy”.
Jordan smirked “Not dark, wet and bitter, like his woman?”
Claire came in then. She asked “What was all the laughing about?”
“Cathy thought it was funny that Jordan has lost my trousers” I said.
Claire peered at Jordan and took in her skimpy dress, then she looked pointedly at me and my skimpy dress, without saying a word she raised a quizzical eyebrow.
“Fascinating” she said, absolutely dead-pan.
Cathy cracked up again as Claire struggled to keep an impassive expression.

Finally, Claire couldn't hold it any longer and just gave a very unladylike snort before she too cracked up.

“ She may have lost your trousers, but at least you got into her dress!” Claire said.
“Ah, but did you get into her knickers? Enquiring minds want to know!” Cathy asked me. Before I could think of a response Jordan came back:
“Oh, I never wear them, myself. But Bobbi has enough knickers for the both of us!”
Cathy gaped like a fish, I grinned and nodded and Claire giggled like a lunatic. Becky came through the door and stared at the three of us as if we had escaped from a lunatic asylum. Cathy suddenly stopped, I guess she did the math and worked out that Fiona was the last one left in the loo. With that thought clearly the urgency of her need to prepare was back with full force.
“For F***'s sake, don't make me laugh again!” She warned darkly as she minced towards the bathroom.

“What was she laughing about?” Becky asked. Claire giggled as Jordan replied, “Situational comedy”.
Becky looked baffled.
“You had to be there” I offered, my voice rising slightly at the end to turn the statement into a question. Jordan grinned at me.
“Exactly” she said, and stepped in to kiss me.

I don't exactly remember what happened for a while after that. Her lips were red and glistening and her mouth claimed mine with a finality that brooked no denial. She was very strong. Or maybe I was weak. I didn't know it was possible to get someone else's tongue so far down your throat.
I don't remember much from then on for… well, a while. I stopped thinking. I think I stopped breathing. When Jordan pulled away I think I whimpered.

My entire body tingled like I'd had an electric shock. I blinked and looked around. Claire, Becky and Fiona were staring at the two of us, gaping. Cathy came back in then.
“What did I miss?” She asked, seeing the three women's stunned expressions.
“Pure porn…” Becky said, visibly pulling herself together.
“Wow…” breathed Claire, who looked a little flushed.
“You've never seen two girls make out before?” Jordan asked with an impish grin.
“Nu-uh” said Fiona.
“Right, I think it's clear you two won't be sharing a bed in my house tonight!” Cathy said firmly. She had a twinkle in her eyes, but she meant what she said.
She continued, “Bobbi, you can sleep in my room. Fiona, are you alright keeping an eye on Jordan? Becky and Claire, you can have the sofas in the living-room.”

Jordan pouted then she suddenly became more conciliatory. “Thank you for letting me stay, I know you don't know me yet, but I would love to get to know you all, not just Bobbi”, she gave me a wink as she said my name, “I have never had as much fun at an office Christmas party as I have had with you guys!”
Cathy's stern demeanour softened slightly. She said; “You're welcome to stay, but Bobbi is, I think, very vulnerable tonight, with emotions running high, and the alcohol has been flowing. I don't know who would be taking advantage of whom, but I don't need the drama on a work night.”
“You lot didn't take the day off after a Christmas party?” Jordan asked incredulously “wow, you really are hardcore party animals!”
“We may be, but Bobbi isn't. I think we better drink up and get to bed”.
“Wait…” I said, something was bothering me but I was feeling a little fuzzy now… “Work? What am I going to wear? How do I get my boobs off? Lucy stuck them to me! I can't go to work looking like this!”
“Let me have a look” Cathy said. I went over to her and she started to investigate my chest area. She realised the other four women were staring at my chest. “Ladies. A little privacy? Please.”
Jordan pouted but turned away, the others reluctantly followed suit. Cathy had pulled the top of the dress down and had my boobs on display when Jordan turned around again to look. Jordan held her finger to her lips as she looked me in the eyes and I kept quiet as Cathy prodded and poked. Cathy was so intent on figuring out how to get my attachments off that she didn't notice Jordan.

It made me feel strange, seeing a beautiful woman staring lustfully at my tits. Shy, proud and aroused. I stood a little straighter but kept my head down. Cathy noticed my change in posture and looked round. By the time she looked all the women had turned and were looking at me.
“Hmm, doesn't look as though we need to worry about you being embarrassed, you tart!” Cathy said.
“It doesn't feel like it's really me” I admitted “it's like I'm a puppet of myself or a game avatar, just role playing or something”.
“So, what role are you playing, exactly, when you are standing round with your tits falling out?” Cathy asked with a wry expression on her face.
“Ooh, I know, I know!” Said Jordan “my sissy girlfriend, trying to tease me into becoming a lesbian!” Jordan's eyes became enormous as her face took on a shocked expression “and it worked dammit!”

Cathy cracked up again, and I couldn't help laughing at Jordan's antics. It was an odd sensation, the breasts that were firmly attached to my chest jiggled in time with my chuckles.
“They're quite firmly attached, aren't they?” Claire observed, “very realistic!”
Fiona was looking a little flushed and Becky was starting to look bored. I'd got the impression that she was often bored if she wasn't the centre of attention, a bit like Jordan, though a bit less 'in your face’ about it than Jordan.

“It's quite simple, go into work dressed as a girl. With Claire and I both here you know you are going to get the full backing of HR, so there's no way you can get into any trouble. Plus, everyone has already seen you in that dress…”
“And so much of her is on show!” Fiona inserted her comment quickly into the flow of Becky's words.
“Quite.” Said Becky.
“I could just get up early and go home and get a suit?” I said.
Cathy said “No, I don't think that would work, actually. You don't have a shirt you could do up over that chest, I don't want you flashing more cleavage than Jordan at work… ” that got a “Hey!” from Jordan, which wasn't very compelling given how she was dressed, Cathy continued “... and I don't want you at work in baggy leisure wear, we have a dress code, after all and HR are keen to enforce it.”

“Yes, we are!” Becky agreed, Claire nodded too.

“Ok, so what can I wear then?” I asked, a little annoyed. I had thought I would wear a hoody and hide in the corner.
“Well, it can't be anything of mine, it would swim on you!” Cathy said. Cathy wasn't fat, but she was very curvy and certainly not as skinny as me.

Becky and Claire looked at each other and Becky said “Well, we didn't bring a wardrobe with us, we only have the clothes we were going to wear ourselves.”

“Sorry, sweetie” said Jordan, “I don't have even that much, in fact, I have as going to ask Fiona if I could borrow something tomorrow?”

We all turned to Fiona …

“Well… my trousers wouldn't be any good to either of you, they'd be far too short and look like culottes! But I do have a smart pinstripe skirt suit for Bobbi and I'm sure I can find a dress for Jordan that would show some cleavage!”

Jordan stuck her tongue out at Fiona.

“Ok, we'll do that. Bobbi and I will need to be up at 6 so I have time to sort us both out.” Cathy said.
“6.00a.m., in the morning?!” I tried to convey the full horror I felt at having to wake up in just a few hours time.
“Oh yes. If your going to be a woman in my team, you'll be the best damned woman I can make you!” Cathy said with relish, she went on; “Fiona, can you give me the suit, two pairs of tights and some underwear, so I don't have to wake you in the morning?”
“Sure, I guess. Why two pairs of tights?” Fiona asked.
“Bobbi's never put tights on before…” Cathy said and waited for Fiona to figure it out.
“Got you, high derniers it is then!” Fiona said.
Cathy turned to Jordan next.
“Are you ok with me turfing you out at eight?” She asked.
“Oh sure, I guess it's a bit much letting a stranger sleep in unsupervised after you go to work. It's not the first time I've had to slink home in the morning. It would be nice if someone could lend me a change of clothes in the morning, I'll have them washed and returned before you know it. Oh, and if you have a spare toothbrush?” Jordan said, smiling brightly.
“I'm sure Fiona can sort you out” Cathy said as she looked across at Fiona who smiled and gave a slight nod. “Come with me, young Bobbi” she told me.
“But… my coffee!” I protested.
“Will be cool enough for you to drink when we get back.” Cathy said.

“Wait!” Jordan cried out when Cathy went to lead me away “We need selfies to capture this moment!”
“She's absolutely right” Fiona said “There has to be pictures.”
“What? You don't have enough blackmail material already?” I asked.
“Humph, you try giving someone a simple makeover, and this is the thanks we get” Becky said. I wasn't sure if she was serious, but I thought it probably wasn't a good idea to antagonise her as my safety tomorrow could depend on her.
“Ok...wait...where's my phone?” I asked, suddenly panicked at the thought of losing my phone.
“In your handbag, silly, like all of us!” Jordan said as she handed me the little bag I'd nearly forgotten when we'd left the hotel. I looked inside to find my phone, two condoms, two tampons, a sanitary towel, a purse and some lipstick. My face must have shown my confusion.
“Well, you had to have somewhere to put your stuff, and I wanted it to look convincing.” Jordan said.
I shrugged and got my phone out, unlocked and handed it to Claire.
“Can you take some of Jordan and me?” I asked.
Claire got us to pose together and pull a few faces as she took a few shots then Becky took the camera from her and ordered her into the shots, too. We were goofing around with Fiona and Claire when Cathy came back. I don’t know how many shots Becky took.

Cathy took a few shots with Becky in them and then gave the camera back to Becky and got a nice photo of just her and me together. I still have it in my gallery. I think it makes us look like a mother and daughter.

Becky said “I don’t know what you’re doing, Bobbi, but the camera really loves you. Step aside, Cathy, and let’s see Bobbi strut her stuff...Show me ‘vulnerable’!”

Cathy moved away and a thought for a second and turned puppy dog eyes to the HR bitch who could ruin me with a thought.

“Show me ‘Happy’!” Becky said, just as Jordan stuck her tongue out to me and waggled her tounge piercing, I couldn’t help giggling at her antics.

“Show me ‘Love’!” Becky said, getting into her role of camera-woman, she sounded a bit like Austin Powers from the movies, I half expected her to say ‘and… I’m spent!’. I thought about what the tongue-piercing might mean for me, if Jordan was my girlfriend and I gave her a big smile.

“I said ‘Love’, not ‘Lust’!” Becky said “But… close enough. You could be a model, you know. Fashion loves that androgynous, flat-chested look.”
“Bobbi’s not flat!” Jordan leapt to my defence “We stuck a nice rack to her!”
“You goof!” I said to her fondly, “I am too, flat. At least, I would be without these prosthetics”. I hefted a double-handful to make my point.
“C’mon” said Cathy “Enough goofing around, we have to get ready for bed”.

She led me off to the bathroom upstairs and gave me some wipes to take off my make-up.
“Er… I think I need to pee” I said.
“So, why don't you, then?” Cathy asked.
“I can't feel my willy, or my balls.. “ I said “I'm a little nervous what I'll find 'down there’”.
“Well, there was no time for surgery and no blood, so I think we'll be fine. Do you want to try by yourself, or do you think you need assistance?”
“I'll try it by myself, I guess. But, please, don't go too far.”

“Do you mind if I take a look at how you are trussed up? I didn't get too good a look at what watsername, was up to when you were getting done up and if we are going to keep you from having an obvious outy where you should have an innie I may need to learn some new tricks”.
“I guess not” I sighed, as I started pulling my dress up so I could see for myself what Lucy had done.

We both said “Wow”.
I was wearing pretty lacy white panties over a flesh-coloured pair of elasticated shorts of some sort. But the shorts were kind of padded or moulded. In the same way that Batman's outfit in the latest movies made him look like he had muscles and a six-pack, only these “spanx” as Lucy had called them made it look like I had a lady's butt and no willy.
“Pretty sophisticated for a hotel's 'lost and found’” said Cathy.
“Julie said that they were samples for an event that they hold sometimes” I said, “I think, maybe, there are a lot more men dressed as women wandering around than we think”.
“Well, if they look as good as you and Lucy then no one would ever be able to guess that you weren’t 100% female. I never guessed about Lucy and, dammit, you look too good to be true. I’m going to find it hard to ever see you as a guy again!” said Cathy.
“Thanks, I guess. Still it should be easier to see me as male once I get these spanx off and get my willy out!” I said with more bravado than I really felt. It was ridiculous to be trying to channel my machismo under these circumstances, but I was about to drop my pants, well, panties anyway, in front of my boss. Not something I would have believed if you would have told me yesterday morning.

I eased the spanx down and found my willy, looking quite shrunk and shrivelled. My testicles looked odd, like someone had hollowed them out and pressed the wrinkly skin into my body. Which I guess was almost what had happened. Cathy looked a little confused, so I explained…
“Lucy made me press my testes back up into my body.” I told her.
“You can do that?” she asked, seeming a little shocked.
“Well, I guess I can. Maybe some guys can’t? Mine didn’t actually come out of my body until a few years ago.” I said.
“Really? Maybe that late development is why you look so good as a girl?” she said.
“I don’t look good as a guy?”
“Oh, you look very pretty as a guy, too, I guess - a lot of the young women are into that kind of thing these days I think.”
“Really? Not the rugged, hairy chested macho men?”
“Not so much… most of the younger girls I talk to want someone who’s not a massive dick. Everything else is gravy. Still, every girl is different, and we can all change our minds! Ok, I think we need to leave the spanx off tonight and let things breathe. I’m guessing that will mean your balls drop again in the night and we’ll try and stuff them back inside you in the morning, what do you think?” Cathy asked.
“I’m not very keen on ‘stuffing’ any sensitive bits of me anywhere, but they slipped in once, I guess we can get them back in the morning, unless there’s some swelling or something. Do you have any boxer shorts?...” I trailed off as I saw Cathy’s face.
“Do I strike you as a ‘boxer shorts’ kind of girl?” she asked.
“No ma’am!” I said hurriedly.
“Hmph! ‘Ma’am? Anyway, I have a sleeping shirt and some sleep shorts. The shirt will swim on you and the shorts will fall down… I’d better ask Fiona. Will you be alright getting the rest of that makeup off while I ask?” Cathy said.
“Sure, it won’t take long. Do you have a toothbrush, too?” I asked.
“We have some manual ones, don’t worry. I’ll go and get them.” she said, and left.

This was the first time I’d been alone since I had been dressed as a woman. I took the opportunity to look at myself in the mirror before I took the makeup off. The makeup was a bit smeared, I guess from kissing Jordan. So I looked a little trashy, but I looked a lot better than I was really comfortable with. Lord knows, I looked out of Bobby’s class.

I got to work wiping the make-up off and I was astonished how much stuff came off my face and got left on the wipes. When I looked in the mirror again I looked very different and a bit washed out and pale in the harsh light.

But, I still looked like a girl, to my eyes. Not just because of the incongruous breasts hanging from my chest but because of the shape of my eyebrows and, I don't know, something indefinable about the way I carried myself. Perhaps the oddest thing was that I felt happy about that. I don't recall ever feeling like I was a girl before. I was acutely aware of my deficiencies as a man. Too short, too slender, too graceful. But those things that marked me out and held me back as a man were positives if I were only a woman.

Maybe...maybe, I should make the most of this opportunity? How many men had the chance to see life from the other point of view? What had I got to lose? My manly reputation? Pshaw. My love life? What love life? I got more female attention, dressed as a woman, than I had ever got in my whole life before. Except from my Mum, of course. I wasn't sure how she would take this, but there was no need to let her know, at least, not immediately.

Cathy came back to find me staring at myself in the mirror. She didn't say anything for a while, she just watched me.
Eventually she asked “So… what do you see?”

“Me… a me I have never met before.” I said.

“Hmm, I think we are all going to enjoy getting to know the new you” said Cathy, as she handed me a toothbrush and a very small bundle of dark green satin and cream lace.
I unfolded the bundle to find a pair of lacy green knickers and a beautiful dark green satin nightdress with cream lace detail, thin straps on the shoulders and a plunging neckline.

“It is beautiful, but not very comfortable?” I said.
“You may find it's more comfortable than you think...Jordan asked if you could say goodnight before you head to bed. You may want to wear this peignoir, or she won't leave you alone!” Cathy said as she handed me a kind of lacy dressing gown. “I'll leave you to get ready, come through to the kitchen when you’re done. Then my bedroom is the one at the top of the stairs. See you in a minute?”
“Sure…” I said.
Cathy left and I slipped on the nightie. It was warm, where it touched my skin, which I didn’t expect. I thought the lace knickers would be scratchy and uncomfortable but they were smooth on the inside and touched my skin so lightly that they almost felt like they weren’t there. I shuddered, suddenly overcome by the sheer sensuous pleasure of wearing these pretty clothes and my willy started to stiffen. I remembered that I would have to go out and face my work colleagues, who might have their cameras out (on their phones) with no makeup and this short clingy night dress and the problem went away.

I wrapped the dressing gown thing that Cathy had called a ‘peignoir‘ around me and tied the ribbon tie in a bow at the side. Unlike the towelling dressing gown I was used to this was not opaque, not warm and it did more to frame my nightclothes than cover me up.

I cleaned my teeth and returned to the kitchen, walking softly on bare feet. The girls were talking as I slipped in…
“... damn if he isn’t the prettiest girl among us!” Claire said.
“Not the sexiest, but the camera loves her” said Becky.
“You’re a very lucky lady!” Fiona said to Jordan.
“I think Bobbi will feel that she is the lucky one, if you give me half a chance!” said Jordan.
“Please, go slow Jordan” Cathy warned “I think Bobbi is going to find things very strange tomorrow and it may cause….Oh! Sorry sweetie, I didn’t see you there!”
I had been discovered.
“Sorry, I didn’t mean to sneak up on you… What do you think it might cause?” I asked.
“Hmmm? Oh… yes, sorry, talking about you without bringing you in on the conversation. I was just going to warn Jordan not to break your heart, dear!”
“Grrr, that’s NOT what you were going to say!” I answered hotly.
“Oh my god! You are so CUTE when you get angry! I may have to tease you. A lot” said Jordan.
“Cathy?” I said, as I waited for a reply.
“I know it’s a big deal for most men, dressing like a woman. I’m sure it will cause… ripples?” Cathy said. She sounded vague, lame and apologetic at the end.
“Ripples?” I said flatly.
Becky jumped in with both feet, “When you turn up looking like you went from an underdeveloped boy to a stacked Lolita it’s likely to be noticed! You are gorgeous as a woman and that will change how people react to you and, most likely, how you will react to them.”
“It’s one day in drag, what’s the big deal?” I said “Can’t we just say it’s for charity or something? Justin wore a pink dress for Breast Cancer that day and no one thinks he’s… anything.”
“Anything?” Cathy asked.
“I don’t know, gay, trans, weird, whatever!” I said hotly “I wear women’s clothes for a laugh for a few hours and people are trying to pigeon-hole me!”
“Oh.” said Jordan, like someone had stolen her ice-cream “This isn’t a permanent thing?”
She had the strangest expression, half mocking, like she was in on the joke that we were playing on the rest of the world and half wistful, hoping she would convince me to become her lesbian playmate.
“So” I said, desperately changing the subject “ You still think I look pretty without the makeup?”
I posed slightly in the green lingerie, casting my eyes downwards, shyly.
“Oh yes! My pretty peach blossom.” Jordan said, leering at me, “very nice!”
“You are a pretty, pretty Princess” said Becky tiredly, “So, can the rest of us get ready for bed now?”
Cathy said “My dibs on the bathroom first! Bobbi, go on up to bed, dear, you must be exhausted.”
I kissed Jordan goodnight, then headed up to bed. I don't remember taking off the peignoir, I was asleep before my head hit the pillow.