It Started At Christmas Pt. 01

When I started work after graduating, times were tight, and nights out were expensive, most of my money went on rent and bills, so nights out were very much a premium and those of us who started with the company at the same time tended to have cheap nights in a lot of the time. As a result of one of these nights in, Kate (a colleague with a boyfriend overseas) and I started a FWB relationship, sharing a bed every now and then and on one particular occasion sharing stories of our past.

She therefore knew I'd had the odd experience while dressed at University (1 with a female hockey player and repeated nights with my female manager at the nightclub I worked at,@# well as a New Year's Eve dalliance with the owner of the club, which repeated itself twice).

Kate being a size 16/18 and me being just a bit bigger, we'd had a couple of evenings in her lingerie, and she made me up on one occasion too... these were our nights out. Most of what we did was vanilla, though she did use a vibrator on me once, which I enjoyed, but it was mainly reciprocated oral, or normal sex in a variety of positions, and rooms!

We'd also had a giggle, as she told me that there was someone she worked with who had the hots for me, but wouldn't tell me who it was. I eventually went through all the females, including the 60 year old secretary, before she eventually put me out of her misery and told me it was a guy called Damien.

So it came that on a Friday two weeks before Christmas, her housemate was away and we were having one of our dress up sessions, and she told me that Damien had broken up with his boyfriend and as a result his +1 for the department Christmas party was free if I was interested. It was a Dinner Dance at the local Holiday Inn, and while the night out was not to be sniffed at, I wasn't ready for the ribbing at being Damien's +1.

"What if I made you up and you went in one of my cocktail dresses?" Kate said, and I laughed... but noticed she was deadly serious. "Me, you and Damien will be the only 3 who know, and even though you'll probably be twigged as a crossdresser, no one will know it's you, I can promise you that. So what do you reckon?"

"OK, if you can make me over tomorrow and I agree that I don't look like me, I'll do it." I said "but we will need to get a wig and I'll need a pair of shoes that fit me."

"We'll hop on a train into London tomorrow morning and we can get what we need and then have a proper dress-up session tomorrow evening" Kate said, before noticing this chat had got me hard as a rock, and cutting off the conversation for some animal sex.

The next day we were up early, and Kate made me shave my legs and wear ker knickers and a pair of tights, as she wanted me to try on shoes. We jumped on the train and hit the department stores, looking for a size 9 pair of heels. 25 years on, size 9s are everywhere, but back were not easy to find, and we found a pair which would do, but Kate, having told the lady it was for fancy dress, asked if there was anywhere that did a bigger range of large shoes, and the lady sent us to Evans, where we found a pair of 3" heeled black stilettos in a size 9 wide fit, which Kate said would be perfect with the dress she had in mind for me.

Shoes purchased, we found a brunette bob wig, and headed home on the train. Once there, I was dispatched to shave legs, chest and arms, and Kate came and completed the hair removal, before starting the full makeover. Fully made up, she put out lingerie, which I slid into. She then came in with the dress she had in mind for me, and while a little tight, it fit reasonably, though I needed to pad the bra somewhat as she had a D cup. I'd also need to wear a different bra, so Kate suggested I shop for strapless bra, thong and suspender belt in my size in the week, as there was no trace of me and I merely resembled a tall slightly masculine girl, so I began to think I could do this. The dress was black and sparkly. It had a halter neck which tied behind the neck, and diamanté's in a pattern across the chest are and down the right leg. There was a very high clit up the left leg (to mid thigh) which made my legs look amazing, though I'd need to be careful not to give a flask of stock8ng and suspenders.

Kate had me out of the dress so as not to spoil it, but I popped on another dress and we opened a bottle of wine and chilled for the rest of the night, me getting used to walking up and down in heels initially, then having a bit of a dance later.

We collapsed in bad at about 11, excited at the thought of next Saturday.

When we woke, we were both incredibly aroused and spent a hot day just enjoying each other and thinking about the weekend ahead. Kate sent me packing with the heels and tights, telling me to practice each evening (I lived alone) and reminding me I needed to get a strapless bra (40D), thong and suspenders, preferably in black and some black stockings as well. We finished off the weekend with Kate giving me a blow job then coming up and sharing my cum with me (my first taste since the last NYE party at Uni) before she sent me packing before her housemate came back from her boyfriend's.

I nervously drove to a big Marks and Spencer's after work on Monday, and armed with a hastily scribbled list, I managed to pick up everything I needed without blowing the budget. I rushed home and couldn't wait to try the bra and thong on, noting how they fit slightly better for being a size 18 and 40D, rather than the 16 and 38D that Kate wore. The memories came flooding back and it wasn't long before I was on the bed, still in the lingerie, and cumming intensely from a rapid orgasm.

I ate the bare minimum all week, desperately trying to lose a tad of weight before Saturdays party, and have to say that the week itself didn't see much productive work done, as my mind just raced away thinking of the weekend. I had a coffee with Kate on Tuesday, and another with Kate, Damien and a girl called Seema on the Thursday, where they excitedly talked about the dinner dance, and I bemoaned the fact that I'd be bored at home. I had a chuckle to myself that night as I paraded round the flat in my high heels, getting properly used to them now.

Friday morning, I packed my girlie things in a small bag and went to work as normal. Again, not very productive, but 4 o'clock came round quickly and I drove round to Kate's via the shop to pick up a couple of bottles of wine. Kate was a little late, as she had been to pick up some glue on nails that we had forgotten, so I was sat outside in the car when she got there. She told me she was going to do a final trial of everything so we spent the first 90 minutes getting me dressed, then at 7 the doorbell rang, and she ran downstairs. She shouted me and I went down, to find Damien standing agog.

"Wow, you do look good" he said, "we're going to have fun tomorrow I can see." He'd brought round a bottle of wine, so after slipping out of the dress into another one, we chilled and had a couple of glasses of wine before he headed home, giving us both a peck on the cheek, though I noticed the hand that rested on my backside, and stayed there a little too long, never went near Kate's.

Kate and I opened a second bottle and watched tv, before I took the chance to open her legs and dive between, messing my makeup up as I tasted her at length. We decided on an early night at that point, as we had a busy and long day the next day, though not before I stripped the dress off and took Kate from behind on all fours. She said she'd never seen me so horny, and she was right. I flashed back to the times before in lingerie and stockings and remembered that when dressed my sexual appetite went through the roof. We collapsed in a heap and Kate made me take the make up off with some wipes before we hit the sack.

Saturday saw us lie in and enjoy each other's bodies a couple more times. Kate got her vibrator out again and teased me, and we had 2 orgasms each before a scented bath was drawn and I soaked and shaved all over again, with Kate doing the bits I couldn't reach. For some reason, and don't ask what made me, I shaved a landing strip above my bits as well (Kate had one and I thought it added that bit extra). I put on a robe of Kate's and she filed and painted my toenails a dark red colour, she also tried the stick on nails for size and painted 10 of those in matching red while they were on blobs of blue tack stuck to an A4 folder (funny what you remember isn't it?) Once the toenails were dried, I slipped into some shorts and a t-shirt and made us a light lunch.

After lunch, I shaved my face and Kate put a face mask on us both. We chilled with a coffee before peeling it off, and then the real hard work started. Kate made me up first, even better than the trial run, and then started to get herself ready. I started putting on my base layers, stockings and suspenders first, then thong and bra. We had spent some time with the face masks on stuffing old tights with tissue paper, balling them up to make reasonably shaped breast forms to fill the D cups. I slipped these in, then put the robe back on and finally slipped the wig on. My Mum wouldn't have recognised me!

Kate was ready soon after and she looked stunning in a basque, thong and stockings, her hair in ringlets. She gave me a necklace and bracelet and some clip on earrings she had from the days before she was pierced, and we squeezed a couple of rings on with the help of some lube. She then added another layer of mascara really making my lashes stand out, played with my hair and applied some hairspray and some lip gloss, before getting the glue out and attaching the nails to my very unfeminine bitten fingernails and spraying me with some perfume.

6:45 and all that was missing was the dress and the heels. Kate supplied the dress and zipped me up, and I returned the favour. Wow, she looked good, and I kind of wished I was taking her on my arm, but then I looked at myself and realised I was going to have so much more fun. A clutch bag was placed in my hand, with lipstick, a compact mirror, a tiny bottle of perfume, and a purse which I stuffed about £40 in. Kate wrapped a throw around my shoulders and that was that.

Damien picked us up at 7 and was mightily impressed. He reminded us that Kate and I didn't really know each other as far as everyone else was concerned, so we should not start the evening as bosom buddies. I was a little put off by this, but Damien told me he'd be there for me, and off we went.

We met up with the other department members at the hotel bar and I was introduced, Damien called me Michelle, and it dawned on me we hadn't come up with a name. I smiled sweetly and tried to put on a neutral voice, but I think everyone knew I was male, but wasn't surprised by it as Damien was completely out as gay. I was accepted though, and we chatted (me playing ignorant about the company and asking dumb questions about it). Dinner was nice, and the wine flowed. As the evening went on, Kate and I "became friends" and danced a little together, though we were both getting male attention from other department members and from other companies there.

At about ten, Kate was barged by a guy on the dance floor and went over on her ankle. It came up like a balloon and she needed an ambulance, which was called, and which left me there with Damien. I felt awful leaving her to go alone, but as I "barely knew her" what could I do. A single guy from the department ended up accompanying her, and Damien and I danced away the evening and had as great a time as we could.

The department head was the only person with a mobile phone (different times) and he got a call saying Kate had broken a bone in her foot but given she had been drinking and lived alone they were keeping her in overnight. Nothing for it, I'd have to go home with Damien and work the rest out the next morning.

We called a cab, chattered excitedly all the way home, and Damien opened a bottle when we got in. His housemate Cathy was away so we put some music on and talked while drinking the wine. Then he kissed me, and much to my surprise I kissed him back. When we eventually came up for air, Damien said he wasn't expecting that. "This isn't the first time" I said, "but I only have a thing for guys when dressed."

"I'm fine with that" said Damien "but no pressure, there's Cathy's room or you can come in with me, your call." I kissed him again, finished my wine and told him to take me to bed.

I removed the dress and shoes, but showing my naivety, didn't think about removing makeup, I just jumped into bed in my lingerie, and was waiting for Damien when he walked naked into the room. His was bigger than any cock I'd ever played with, and as he lay down next to me and we kissed I began playing with it, trying my hardest not to stab him with my red talons. He certainly responded to my touch, getting hard quickly, and I slid down to take him in my mouth. As I refamiliarised myself with oral, Damien caressed my legs and bottom, and he was soon ready to burst, which I encouraged him to do. He filled my mouth with three pulses, which I managed to swallow, before a couple more spurts covered my lip and cheek, but I tidied that up, and moved up, kissed him and lay on the pillow next to him.

"Wow, unexpected!" He said. "But fantastic" and he kissed me again. He stroked the front of my thong, sensing me getting hard as he touched me, but I moved his hand away and said maybe later. "Beauty sleep" I said, kissing him and turning over, letting him snuggle into me in the spoon position, and feeling him twitch into my back, gradually hardening and rubbing against my bottom, before we both fell into a deep sleep.

We were woken by his phone ringing at 10am and he ran downstairs to answer. I nipped to the loo and realised my make up was a state, but didn't know what I could do. I found a couple of wipes and removed what I could, but for some reason put some lipstick back on when I got back to bed. Damien returned with 2 coffees and we sat cuddling in bed drinking them. "That was Kate" he said. "She's likely to be discharged after rounds early this afternoon and she wanted to know if we can collect her. I said we could."

"Sounds good" I said and sipped my coffee before pulling a face.

"What's up?" He said.

"Well, I've an evening dress, high heels and nothing else, so what am I going to put on to pick her up?"

"Well, we can leave you in the car, or could be more fun if we found something in Cathy's wardrobe for you."

I said I'd think about it, and we kissed. Damien asked what I wanted to do, and I told him I'd love to feel him inside me. "Hoped you'd say that" he said, and reached into a drawer and fished out some condoms. He took his time lubing me up and opening me with first one, then a second and finally a third finger. Come this point, I was begging him to slide into me, which he gently did inch by inch. As he did, I felt myself stirring and before long I was as hard as a rock. He started moving in and out and within about 12 gentle thrusts I came floods without touching myself. Damien was getting thicker inside me and I could tell it wouldn't be long, and he also came buckets inside the condom before falling forward and putting his arms around me. We fell asleep again before waking and realising we needed to get moving, but not before I sucked him to another creamy finish.

So, 2 hours later, decision made, I'd removed the rest of last night's make up, showered, and was looking through Cathy's wardrobe (we'd cleared it with her saying Damien's friend who stayed over needed to borrow some things), and I ended up with a red satin feel shell top and a calf length black pleated skirt. I managed to find some of Cathy's make up and having remembered roughly what Kate had done, I scrubbed up not too bad, and we headed to the hospital. I said very little on the way I recall, as I was nervous, and I nearly bottled out, but a hug and kiss from Damien filled me with confidence.

Kate's face when she saw me was a picture. A high heeled Michelle pushed Kate to the lift and to reception while Damien brought the car round. Once home, Kate was on the sofa and I began the task of looking after her. We both had a fortnight off with Christmas being round the corner. Kate had lost her mother two years ago, and didn't speak to her father, and was due to be flying to see her partner for Christmas in the US, going on some walking trail, which she wouldn't be able to do. He wasn't happy and said he was still doing it and they had a massive argument while I skulked in the kitchen, and there was a distinct feeling of breakup in the air......