A Christmas Party - part 1


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

Hi, I'm Bob Smith, and I want to tell you about an unexpected thing that happened at my works Christmas party this year.

I started my new job as a software developer in early November. It wasn't my first job, I had worked for the local council for a few years once I left college and they had sent me on various training courses, but it was my first job in the commercial sector and I found it hard meeting all the new people and trying to find my place in the company.

I didn't really want to go to the office Christmas party, but my Mum had convinced me that it was a necessary evil when I'd called her after I got the details in an email at work. The girls in HR had set it all up. It was going to take place at a local hotel that had conferencing facilities and did wedding receptions and the like at weekends. It seemed a bit swanky to me. We got several reminders via email telling us where and when it was, asking people to confirm their menu selection and the dress code. The dress code seemed to be aimed specifically at the men. It was clearly stated, for the avoidance of doubt that, although the party was not a formal black tie dinner, tuxedos would be appropriate, jeans, t-shirts and trainers definitely would not be. We would be representing the company in public and anyone not dressed appropriately would be asked to leave.

I asked my boss about it and she told me that, a few years ago, some of the younger male colleagues had turned up in jeans and leather jackets and the HR girls had been so infuriated that they had given them a hard time for the rest of the year. There was nothing specific done, but the atmosphere of simmering resentment to those guys kind of infected the whole company somehow and they had all left eventually.

Oh, and my boss? The development team leader? She's the only woman in the IT team. Her name is Cathy and she's the smartest person I've ever met, I think. I've been impressed by Cathy since I arrived at the company. I think I must have impressed her too, during the recruitment process. They interviewed dozens of candidates and I was the only one that they took on. Cathy has told me that it's very hard getting good junior developers in our area.

So, the big day finally arrived. Work was very quiet, a lot of the female staff left early to start getting ready and there was an air of expectation which was vaguely disturbing.
Once my day was finally finished I rushed home to get ready. I say “home”, but it didn't really feel like home yet. It was a house where I rented a room with 3 others, 2 girls and another guy. I hardly saw Emma and Joe, Emma spent most of her time at her boyfriend's place these days and Joe stayed in his room playing computer games and snacking all the time. Andrea was the third person and she was kind of the “house mother”. She organised joint shopping deliveries for us all, including toilet roll and milk, and bathroom cleaning rotas. The landlord used her as an unofficial deputy and gave her a discount on her rent because she kept everything running. Andrea worked as a paralegal for a local lawyers company. I had agreed with Andrea that I would have exclusive use of the bathroom that evening to allow me to get out on time, but I needn't have bothered because there was no one else around. I could hears muffled explosions from Joe's room, so I guessed he was home already. So, a quick shower and shave later and I was nearly ready to go. Shaving was a little optimistic, I guess, I'm small and blond so I can't really manage the dark 2-days worth of stubble that Mark at work could manage. He was tall and dark and managed to look slightly disreputable to me, a little like the guy in Poldark. I could never see what women saw in him…

So a white shirt, a dark green tailored fit suit ( being small has its advantages in the sales) and a midnight blue tie with a snowflake pattern and I was done. There was no way that this outfit would get me in any trouble with HR!

As I arrived at the hotel I was beginning to wonder if I was a little over-dressed if anything. There were several young ladies wearing not very much trip-trapping into the hotel on vertiginous heels. When I got through the door I discovered why… although the hotel would easily cater for everyone in the company only the younger colleagues and senior management were present. Also, a lot of the male colleagues had not come, I guess they couldn't be bothered to dress-up for a work do. The ladies seemed to have made up for it, the ones who were present had really gone to town, hair, makeup, sequins, silk and satin with slashes up to their armpits and down to their navels, as my dear old mum would have said.
But, what I hadn't realised was that we weren't the only company joining the Christmas party tonight. There was a local car dealership, the local council and a few other companies there was even one old couple on a table by themselves as “the Jones party” and a larger group as “the Smiths” that I assume was a family and friends group.

There were drinks on a table near the entrance, sparkling wine on one side and a “mocktail” on the other. I didn't want to make a fool of myself at my first social event so I went for a mocktail and I wandered into the crowded lobby trying to find someone I recognised…

There was one girl who caught my eye, not because she was pretty. She was attractive enough, but nothing spectacular, looks-wise. No, the thing that caught my attention was how she was sat, how she held herself. She was sat in the middle of a three-seater sofa with a crowd of men, young and old, around her. She looked like she was a queen and they were her court, even though she was a young woman, early twenties I would guess, in a tiny red sparkly mini dress that looked as though it was demonstrating the limits of the tensile strength of lycra (she kept adjusting it, as I watched). She held the attention of all the men around her. She was spectacularly vivid in her looks and mannerisms. But I didn't recognise her or any of the men she was with, so I carried on with my search.
A short time later a found Cathy standing with Becky and Claire from HR. I said 'Hi’ and stood around, trying to figure out what their conversation was about. It was a, sometimes hilarious, careful and detailed critique of everyone within view of the corner they were in. To call it “bitching” would be unfair, as some of the comments were quite positive, especially about some of the more attractive guys. But the most shared glee was clearly obtained from the shared quiet dissection of other womens’ outfits and appearance.
“Did you see the redhead 'holding court’ on the way in?” I heard a voice say. I was surprised to realise it was my voice. Clearly, so were all the women, they turned to look me up and down and then, not all at once and so subtly that I thought no one would figure out who they were looking at they looked back towards the entrance to find the vivacious redhead on the sofa.

“Oh. Her.” said Claire, in a flat voice.
“We saw her on the way in, like you did.” said Becky. “She clearly loves to be the centre of attention, alright.”
“She has no self respect.” said Cathy.
“You have to give her her due,” Claire said “she’s showing a lot of body-confidence. I don't think I'd dare to wear a dress that tight!”
“Or so short.” muttered Becky.
“If she so much as sneezes she'll be showing a lot more body and a bit less confidence!” Cathy said.
“Surely, she's wearing shorts or knickers under that?” I said.
“Hmph!” said Claire “a girl like that will only wear knickers on certain days of the month!”

That seemed to break the ice. After that they seemed to adopt me as an apprentice bitch. Correcting my misapprehensions if I failed to realise just how skanky a young women really was and exactly how clueless the men following them round were.

After about 20 minutes, during which time we were joined by three other women from the company, we were called into the 'Blackdowns Suite' for dinner. Our company had 3 large tables booked and we had to figure out where we were going to sit on our tables. I sat between Cathy and a girl I'd never met before called Fiona, who worked in the training team.

I had worked with someone from training at the council, for a while, so I was fascinated to find out what kind of training they were providing in my new company. I was surprised by Fiona, she was very chatty, not guarded or affected at all. It was almost child-like in the way she just chatted away saying, apparently, the first thing that came into her head.

We hadn't been sat down very long when a guy from the hotel with a microphone came out and introduced himself as Andy, our MC and DJ for the night. Before we could eat, he told us, we were going to play some party games to get us in the mood. First of all, we were going to play a game called 'heads or tails’. Everyone had to stand up and touch either their head, for 'heads’ or their bottom, for 'tails’. There were a few giggles when he said 'bottom’, I can only assume that some of the girls had had some wine already.
The DJ would then flip a coin, call out whether it was heads or tails and whoever was wrong would sit down. Within a couple of coin tosses we were left with only 5 people still playing, one guy and four women. The DJ called them out into the open area on the dancefloor in front of the DJ’s booth and got them to introduce themselves. The guy was called Mark, and he got a cheer from the guys at the car dealership. The girl who had been holding court earlier was called Jordan and she got a bigger cheer from the guys from the car dealership, where she worked, and a few guys from the other tables too. She was fiddling with her dress a lot, I noticed, every time she pulled it down to cover her bum her boobs threatened to pop out and every time she adjusted her cleavage the dress would ride up. But with her brightly dyed red hair, red dress and nails and her huge smile she certainly attracted attention.
Sandra and Alison were slightly older, one was from the NHS table and one was from the local council, I think. Alison’s dress was black lace with a plunging cleavage. She was very short, with serious curves, she wasn't fat, but she went in and out a lot. The last woman was called Tracy, she had a black dress, black boots and very dramatic dark makeup. She looked slightly predatory. When the DJ got to her he said “Oh no! I know Tracy. The prize for this is a bottle of wine and the last person who needs another bottle of wine is Tracy!”
Tracy just laughed and they carried on with the game. Mark was out straight away, Jordan went next and then Tracy won. She blew the DJ a kiss and went to the bar to collect her prize.

The staff started setting up for the next game as the DJ started explaining. They put eight chairs in a row facing away from the dance floor. Then they put 8 reindeer models at the far end of the dance floor, each on a weighted tray. Each tray had some string tied to it and the string was wrapped around a stick. Each string was more than long enough to stretch across the dance floor, which the staff did, to leave a stick about 30cm long wrapped with string leading back to a reindeer on each chair. They were careful to ensure the string went under the chair and came up in front of the chair leaving a string wrapped stick in the middle of each seat.

“Ok” said the DJ “We need a volunteer from each table!”
Cathy shoved my hand in the air and pushed me forward.
“Take him!” She yelled. Fiona and the other girls on our table joined in…
“Take him! Take him!” They cackled like hyenas as they shoved me forward.

Some other tables had people arguing over who wanted to go up. I noticed Jordan just came forward as if it was her right.

I accepted my fate with a cheery grin and sat down between Jordan and another woman. There were only 2 other guys and 5 women on the chairs. The DJ got us all sat down facing away from the reindeer with the stick in our laps. He told us turning around was a disqualifying event and that the first reindeer to reach the chairs, with all the string wrapped around the stick, would win a marvellous prize.

While the rules were being stated I racked my brains for the best way to do this. The obvious way was to have a hand each side and twiddle the stick, but that struck me as way too slow. The fact that the stick was so long and the string was wrapped in in middle made me think that rolling the stick on my thighs was the way to go. Thinking quickly I realised that rolling the string up my thighs, towards my crotch, which was the direction each of us was currently set to do, would put me at a disadvantage, because I was wearing trousers that would wrinkle up and catch on the stick if I did that. I surreptitiously twisted the stick round while the DJ was talking so the string came up on the back edge of the stick, rather than the front edge, so I would be rolling the stick down my legs to wind it onto the stick. Quickly lifting the stick up to my crotch again would allow me to start the process again and I figured I would quickly wind the reindeer in.
I noticed Jordan glanced at my crotch and I guess she did some calculations of her own because she moved her stick to her knees to roll it in the opposite direction, for the same effect. With her tights being anchored to the opposite end of her, very shapely, legs that seemed like a good idea.

The DJ went down the line and got everyone to introduce themselves, then he checked that everyone was ready. I noticed Cathy and Fiona had come to stand by the chairs, I guess for support, or maybe to have laugh at my expense. A number of other people from the other tables were by the line of chairs to support their colleagues, although most people were content to sit at their tables and cheer from afar. It wasn't that afar, we were in in the same room, after all.

The DJ counted down “3, 2, 1! Go!” and we were off.

Jordan was putting more passion than skill into her movements, and her skirt rose up further than ever, proving Claire's assertion to be true, which was rather distracting. The girl next to me was doing a weird exaggerated twiddling motion, which, with her low cut dress and ample bosom was also very distracting. Meanwhile I got into my own groove and keeping my movements clean and precise I managed to bring my reindeer in first. I fact, it smacked into the back of the chair with some force. Cathy screamed “We won! We won!” while gleefully jumping up and down and gesticulating at our reindeer. Which was also quite distracting. Especially as, with the chair placed where it was and her legs either side of mine so she could get a closer view of the reindeer I got a very up close and personal view of her ample charms. Bouncing up and down a few centimetres from my nose. With all this stimulation, it wasn't surprising that I felt a stirring in my trousers. Fiona, from her vantage a little further back, noticed my predicament. But instead of helping me, she talked in Cathy's ear. Cathy's eyes went wide as she glanced down. Jordan caught on to the fact that something was going on as she saw where Cathy's glance alighted. Cathy fell into my lap with a whoop and ground herself against me, thus making a mountain out of a molehill. Well, it felt like that anyway. As she got back to her feet, Jordan reached across and gave my manhood an appraising squeeze through my trousers.
“Well done!” she said, with an odd smile.

The DJ came over and said “Congratulations, Bobby! Stand up and give everyone a wave!”

Thinking dark thoughts about flagpoles and waving I got to my feet gingerly. Cathy took pity on me and strategically positioned herself so that I didn’t embarrass myself too badly.

By the time we made it back to our table with a huge bottle of prosecco I was pretty much back to normal. Fiona winked at Cathy, so she had probably figured out something was wrong but, what the heck? I was a young guy and it happened, especially if older, busty, women rubbed themselves against me, I had nothing to be ashamed of, as several women now had cause to realise.

“Are you going to open that?” Cathy asked, looking at the bottle.
“I’m driving” I said, ruefully.
“Nonsense! Share a taxi with us, you can crash at our place!”
“Your place?” I’d never really had a chance to figure out Cathy’s living arrangements.
“Me and Fiona share a house over in Park Street, a bunch of girls are staying there tonight. Why don’t you join us? You clearly have a sense of humour and you aren’t such a stiff shirt as we were starting to worry you were!”
I thought for a moment… “What the hell! No one is expecting me home tonight.”
I cracked open the bottle with a Pop! of the cork and several eager hands thrust forward empty glasses.

The rest of the night was a bit blurry for a while. Despite my bravado, I wasn’t used to drinking sparkly wine and it went to my head a bit. I remember the meal, 3 courses, pate and toast, roast turkey and christmas pudding for dessert. Then the DJ kicked off the disco, the lights went down and the girls dragged me to the dancefloor. Every time one lot of girls flagged and sat down, another group would drag me up. I’m not sure when I became the designated dance partner but I think I spent something like 3 hours dancing. I must have danced with every woman in the room.

There was one woman I remember, that I hadn’t noticed before the meal. She looked a little like Daryl Hannah from that old mermaid movie they keep showing on Sky. Long blonde hair, very tall. I thought she was wearing heels, at first, because she was as tall as any of the guys, and a good deal taller than me, but I found she was wearing ballet pumps, black tights, a tiny, tiny tight grey mini skirt that was only decent because the tights were so black and a white blouse that was so sheer you could see the outline of her lacy white bra though it. She moved so gracefully, it was uncanny. She had amazing long legs and she ground herself against the men from her table, and, eventually against me, in a shockingly provocative way.

Oh, and there was another girl, well a pair of girls really, who were dancing together. The short blonde in the black sparkly romper was a good dancer and kept egging on the other girl who was in a red dress showing an extraordinarily ample cleavage. The girl in the red dress was, I think, very drunk and very coarse and making suggestive gestures in my direction, which was kind of awkward.

There were lots of other girls who danced that night, of course, but those were the ones that stood out for me for some reason.

At one point Cathy and I were on the dancefloor and Cathy grabbed my hand like we were doing some form of ballroom dance and pulled me close. I let her lead me in the dance, frankly grateful for the support as I was feeling a little tired by then. I looked over and saw the girl in the red dress and the girl in the black romper mimicking us.

“You have inspired us!” shouted the girl in the romper as she dipped the girl in red, nearly tipping her out of her dress in the bargain then pulled her up for a passionate kiss.

As the evening wore on, more of the men vanished, leaving mostly women left. Cathy took me off to one side of the dancefloor with Fiona and explained that I had to go home with them because I was too drunk to drive.

“Well… “ said Fiona “I guess that’s ok, but he can’t come with us like that?”
“What’s wrong with my suit?”
“Nothing, for a guy, but we’re only allowed to have girls stay the night, our landlord is a real stick in the mud. Our neighbour will see you and shit-stir for the hell of it. We’ll have to disguise you.”

I thought for a moment, there was no way I would be able to order a taxi now, and I wasn’t about to risk driving drunk. It seemed like I had very little choice.

“Sure!, How will we do this?”
Fiona grabbed my hand “Come with me! Cathy - grab the girls and get an outfit together! Meet us in the ladies!”

Cathy’s eyes lit up and she was off on a mission. Fiona dragged me into the ladies. I put up a token struggle but I was too drunk to really care.

There was no one else in there, when we first got in, but that wasn’t the case for long. It seemed like every woman at the party had heard of the plan and decided to ‘help’. Jordan came in first, offering to swap her dress for my jacket. Fiona readily agreed and I was stripped so fast I didn’t have time to complain. Jordan followed suit and was down to her bra and tights in seconds. She handed over a tiny scrap of red glittery fabric as Fiona handed her my suit. I have to say, Jordan looked very sexy in my suit, her hips and boobs stretched the fabric in interesting ways. Pulling the ‘dress’ up my hips it became obvious that it would hang a little more loosely on me, particularly around the boobs. The only area where it was not loose was around the crotch. Once again, the attention of multiple women was triggering my ‘galant reflex’, but in the tiny mini dress it looked positively obscene. Jordan guffawed and offered to ‘take care of that’ for me. At the same time various girls were plucking at my eyebrows, pulling off my shoes and generally falling over themselves to ‘girlify’ me. This felt like it had got completely out of hand.

Suddenly there was a shout - “What is the meaning of this!” a woman’s voice roared with unmistakable authority.
There stood Julie, the hotel’s event manager, the woman who had organised the party on behalf of the hotel. Beside her stood the tall girl in the grey mini skirt I had danced with.

Fiona and Cathy rapidly tried to explain. Julie heard just a little of this and then said loudly.
“Ok! That’s quite enough! I will not allow this party to descend into chaos! You, you and you, Lucy - stay - everyone else - out! Off you go! Back to the party!” Julie had pointed out Cathy, Fiona and the tall girl. Jordan piped up “Hey, that’s my dress! I think I should stay, too!”
“Ok…” said Julie through gritted teeth “the four of you stay, everyone else, out!”
Everyone else vanished, it was eerie how the place went from chaos to silence in a few seconds.
“Right, now we can hear ourselves think. What’s going on?”
Cathy explained that I had to go home with them but they were only allowed to have women. There were going to be a lot of women there and no funny business, but I couldn’t go home with anyone else and she had promised to look after me.
“And you are ok with this?” Julie asked me, with concern in her eyes.
“Sure! It may be the wine talking, but I honestly can’t see the big deal. It’s just…”
I looked at the reflection of myself in the mirror and gestured…
“I look a little ridiculous like this.” I turned sad eyes to Julie and she smiled a warm smile back at me.
“Oh, you don’t realise it, but you have come to the right place, sweetie… come with me, girls!”

Julie led us to an office behind the reception desk. She grabbed several boxes, pointed out several other boxes for Lucy to grab, a bag for Jordan and we all were led to one of the hotel rooms near reception.

Julie led us in and told me to shower and shave my legs and armpits and arms. She handed me a ladies razor and some flower-scented body wash, toiletries and shaving gel. I looked at her, slightly baffled. Julie looked at Lucy and Lucy shook her head slightly and then glanced at Jordan.
“You…” Julie looked at Jordan…
“Jordan” Jordan supplied.
“Jordan… right, go with her and see she does it right.”
Jordan eyes lit up and she saluted Julie before dragging me into the bathroom.

I’m not sure what happened next, we were both naked in the shower and there was some rubbing and squelching that didn’t last very long and we came back out, wrapped in hotel towels, I didn’t have any body hair below my neck and I was much less inclined to tenting the front of my dress. Jordan had a smile like the cat that got the cream.

Jordan had insisted that we wrap big towels around our bodies covering our chests and small towels around our hair.

When we came out the other women gave us a knowing look and I was dragged over to the bed. Laid out on the bed was a bewildering array of flesh coloured rubber, women’s underwear and clothing.

“Lucy, dear, can you help… Bobbie, was it? With her bits and prosthetics?”

“Sure.” said Lucy “Don’t worry, I know what I’m doing.”

“That’s great, what are you doing?” I asked.

Lucy lifted a thing like a flesh-coloured pair of padded shorts.

“This will help hide what you have and show what you don't have. Let's call them 'spanx'…”
She lifted two detached boobs.
“I think it’s obvious what these are...these ones will look like they have always been part of you, when I’m finished.”
Ladies knickers, “panties”,
Tights, “tights”,
Bra, “bra”,
Jordan’s dress, “and whatever that is…shall we?”

Lucy helped me get into the stuff while the others talked about makeup and shoes. I felt a little awkward as Lucy strapped me into the spanx, especially as her deft fingers tried to show me how to reposition my testicles.

“Is that really necessary?!” I hissed at her, very quietly.
She looked at me, stood up, smoothed her tiny skirt and did a little turn to show me all sides of her.
“I don’t know….what do you think?”
“You mean…. You!?”
“Yep!” she was smiling now.
“No fucking way!”
“Well, I’m touched that you don’t believe me, really I am, it’s quite a compliment, but I have been doing this for a while. It’s how I know Julie. The hotel runs sessions for cross-dressers and trans-women.”
“First session is free!” quipped Julie from the other side of the room.

As all the women in the room turned to look at me and Lucy, trying to force my junk into the spanx my nads shrivelled so completely that they suddenly slipped into place with a disturbing ease.

Lucy stuck the breast forms to my chest and helped me to put on the bra and knickers, which were lacy and cute and felt strangely scratchy on my newly shaved skin.

I was starting to sober up very fast now, or I thought I was, but there was a weird electricity in the air, a kind of excitement, that almost felt like someone had slipped me some drugs. I was flying under the influence of so much adrenaline and so many conflicting emotions.
Lucy helped me slip into Jordan’s dress, only this time I filled it a lot more convincingly.

Cathy and Fiona came over and Fiona fussed with my hair as Cathy did my face - she plucked my eyebrows, a bit, glued on fake eyelashes, fake nails (Fiona painted them, Jordan did my feet), I don’t know everything they did but soon Cathy put on some lipstick and got me to purse my lips then they strapped sandals to my feet, pulled me into a standing position and pulled me over to pose in front of the mirror.

Fiona and Cathy were stood either side of me, thank goodness, because I nearly fainted.
It was a startling transformation, I wasn’t gorgeous, I didn’t project the kind of sexiness or confidence that the other girls did. But I definitely didn’t look like a boy!

I looked pretty, in a girl-next-door way, like a young woman dressing in her older sister’s clothes.

“Right!” said Cathy “we have half an hour of the party left, then we have to get ‘Cinders’ home. Let’s show her how to party like a real woman!”

Julie had tears in her eyes - “Oh, my dear, you look so good! Go, go on! I can clear this up! Have a magical night, and I hope we see you soon!” she tucked one of her business cards into my handbag (I don’t know where I got a handbag!) and handed it to me as she shooed us out of the door.

We trip-trapped our way back to the party. Everybody turned and stared when we came through the doors together and all the conversations stopped for a moment before they roared back in louder than ever. Cathy and Fiona dragged me onto the dancefloor and Jordan and Lucy started trying to get me to dance like a woman.

I hadn’t realised that there was so much difference between dancing as a man or a woman, but they both showed me how to move differently. It certainly felt very different, trying to balance in high heels. Cathy and Fiona got some more drinks in and I was giggling and wobbling by the time the DJ called the last tune. When the tune ended, and Lucy’s friend and Jordan (who had both grabbed me for a last dance and come up with an impromptu ‘Bobbie sandwich’) untangled themselves from me, the girls dragged me out to the black cab before I could go back for ‘one last kiss’ with Lucy’s friend and we were whisked back to the shared house. There were 6 of us in the cab, Jordan was sat on the floor, I’m not sure the driver had realised she had snuck in.
Fiona, Cathy and I were on the back seat together and Claire and Becky were in the seats facing backwards.

“I bet you never thought that you would get Jordan out of that dress!” said Claire darkly.
“I know for a damned fact that you never would have imagined Bobbie getting into that dress!” Becky said, laughing.
We were all shrieking with laughter as the taxi dropped us at the house.