Halloween

I know Halloween has been and gone, but I'm always late to a party.

Me and my girlfriend had been together since we were in secondary school (or high school, depending which way you look at it), we were now almost 20 and obviously living the high life of students. We were out every weekend we got chance, sometimes together and sometimes on our own. We also tried to attend as many parties as we possibly could. Working part time jobs and having to attend university lectures along side this weren't fun, but what can you do? Little did I know though, that attending a Halloween party this year would change me.

You see, despite us both staying local at university in the North of England, we were both attending different universities. I was at Newcastle university whilst my girlfriend Claire attended Northumbria. So we had our separate friendship groups at Uni whilst having a shared friendship group from when we were in school. As the October half term approached, by now we'd normally had started making plans for our night on the town. Everybody dresses up, gets really drunk and then you end up in a pizza shop at the end of the night, trying your best to eat a pizza whilst falling asleep. Only this year we were in for a change.

We were laid in bed one night, a couple of weeks before Halloween. Snuggled together as we normally would be. Me naked, whilst Claire was in just a pair of panties and a vest top. We often stayed over at each others houses on a weekend. Studying local meant we didn't have to pay for student accommodation. Claire was gorgeous, blonde hair, petite, lovely ass and a great pair of tits. I was a few inches taller than her, which was good... it meant I could throw her around the bedroom. I had a thick cock but no bigger than average in length.

'Fancy doing something different this Halloween?' She asked me, her head resting against my chest.

'What did you have in mind?'

'Well rather than going out into town for Halloween, a few people from my class at Uni are throwing a party in their halls. Most of my friends are going so I thought it might be a nice change.'

'Yeah, sounds good.'

'We also need to start talking about costumes... I was thinking of something completely different for you this year.'

'Well, every year we do it, you always go dressed as a footballer or something daft like that, and it's just not very creative.'

I looked at her puzzled about where this might go next.

'So I thought for a change, we could really spice things up... and maybe you could go as a cheerleader?'

'Ermm... I'm not quite sure how to respond to this love. Isn't that a bit weird?'

'Oh come on,' she moved her hand and begin to stroke my dick, causing it to wake up, and within seconds I was fully erect. 'It'll be fun, no-one will know you anyway so there's no-one to take the piss out of you afterwards.' She said with a giggle.

She took a hold of my cock and began to slowly stroke it, I closed my eyes and rested my head on the pillow as I felt Claire's head leave my chest and then quickly felt the warm sensation as she took my cock into her mouth.

She worked her tongue up and down the shaft of my cock causing me to moan. 'Oh fuck babe, that feels so good.'

She quickened her pace, swallowing my cock whole. But she knew exactly how to make me cum quick and she slowed down. Using just her tongue she teased the head of my cock whilst working her hands around my shaft. Within minutes I could feel my orgasm building.

'Oh yeah... keep going. Don't stop... I'm gonna cum.'

She stopped suddenly, I tried to grab a hold of my cock but she slapped my hand away.

'You can only cum when you agree to dress up for Halloween...' she said.

'I always dress up.' I replied snapping, wanting her to finish what she started.

'No, no. Only if you dress as a cheerleader.' She slapped the head of my cock and then licked it.

'Fine, fine.' I agreed. 'Just finish me off.'

'Pinkie promise?' She reached out her little finger which I matched.

She almost jumped for joy when I agreed to it before going back to work on my cock. Within a minute or so I was past the point of no return and my cock exploded, filling her mouth with cum which she swallowed without missing a drop.

Once she got back into bed after cleaning up she said, 'I'm so glad you agreed, considering I'd already bought the outfit... so you were wearing it no matter what.'

The thing is, I've always had a fetish for crossdressing. I started out when I was younger wearing my Mum's things and it escalated from there. I've always had lingerie on and off but keep having to get rid of it in case people become suspicious. Claire doesn't know about my secret little fetish, but it's been a couple of years since I last dressed.

The next week flew by before I saw Claire again. Getting to her house, she was already awaiting my arrival and quickly whisked me off upstairs to her room. Laid out on the bed was the costume I'd be wearing next week for Halloween. There was a short red crop top, a short red skirt and a pair of white knee high socks. She quickly had me out of my clothes and down to my underwear before chucking the outfit at me to try on.

Once I got it on, Claire walked around looking at me, then she asked me to give her a twirl which I did.

'Okay,' she said. 'A couple of things aren't going to work. We need to get rid of all that hair on your body. I can see it sticking out through the uniform and the socks. And those boxers aren't going to help. There too bulky, you can see them from a mile off.'

Claire smiled at me mischievously.

'I don't think any of my knickers will fit you, so I'll sort that during the week. Everything else I've ordered is due to come this week so you'll have to get yourself here extra early to get ready. Don't worry, my parents won't be home.'

'What do you mean... other things?'

'Don't you worry about it. I've got it all sorted.'

I'd always wanted to go out all dressed up at some point but I didn't think it would happen in this way. I had to play it cool though, make it look like I didn't want to do it, whereas deep down, I couldn't wait for Saturday night to come.

Work and Uni seemed to drag throughout the week, whilst all I kept thinking about was how I would look at the weekend. Claire sent me pictures throughout the week of the outfit she had planned to keep me on my toes. Before I knew it, it was early in the afternoon on Saturday and I was knocking on Claire's door.

She opened, 'come on, quickly, we haven't got time to waste.'

She ushered me upstairs into her room, had me strip down and handed me a razor.

'Right, get yourself in the shower, and I want you completely smooth from the neck down, and the facial hair has to go as well.'

I was in the shower for a good 15-20 minutes and that was after I'd spent a good 10 minutes shaving my face. I'd managed to remove most of the hair from my body, I now had the most difficult parts to do... my ass and balls. It was probably another 15 minutes or so, but with the help of a mirror, I was as smooth as I was going to get.

There was a bathrobe on the back of the bathroom door, which I threw on and fastened before heading back to the bedroom. Claire greeted me with a smile and stroked my face, telling me how much she enjoyed me not having any facial hair. She then undid the robe and had a feel around my body, grabbing my dick, stroking my legs and chest.

'Jesus', she said when she stroked my balls and felt my ass. 'I didn't think you'd go that far but I appreciate the commitment.' She laughed and dragged me over to her make up table and had me sit down.

She took out some red nail polish and began to paint my fingers.

'You seem so relaxed about all this?' She asked me.

'It's 2020 babe, I imagine there's lots of guys who go out dressed as girls on Halloween.'

'Yeah, but I bet they don't shave every hair on their body.'

I laughed. 'You told me to. Plus, if I'm going to do something, it needs to be done properly.

We continued to chat whilst she painted my fingers, she told me all about her friends from Uni and who I would be meeting tonight. After she'd finished, she jumped in the shower to get ready whilst the polish dried before coming back to finish off the rest of my makeover. Whilst Claire was showering, I was just lounging around on the bed looking through my phone. I felt so feminine, the feel of the robe against my hairless body was amazing. It made me question why I'd waited so long to do this.

Claire soon came back and had me sit at the dressing table once again, facing her and away from the mirror. For the next 10-15 minutes she put copious amounts of make up on to me, I had no idea what I looked like, but I trusted her. Just as she was finishing the makeup, she went to a bag inside her wardrobe and pulled it out. From inside there, she pulled out a long blonde wig, the hair was probably just longer than shoulder length.

She placed the wig onto my head and secured it in place, luckily I had quite short hair to begin with so it was an easy fit. She tied two pigtails into the wig with some red ribbon, and once she was done, she spun me round in the chair and unveiled what she was calling her 'masterpiece'.

I couldn't believe my eyes when I looked in the mirror, I didn't recognise myself. The work she had done was incredible. I almost looked feminine and I think unless you were up close and in my face, I don't think you could tell.

'Happy?' She asked, smiling in my direction.

'You've done amazing, I don't even look like me anymore. How have you managed that?'

'Plenty of makeup practice over the years, plus I've watched a few tutorials on YouTube. But less chit chat, we haven't got long. You wait there, whilst I get the outfits ready.'

'Erm... babe.' I looked at her. 'What about underwear?'

I think she heard me, but pretended to ignore me. Instead she continued to rummage through the cupboards, chucking various items of clothing over her shoulder like something from a cartoon. Next thing, she pulled out a blue cheerleader outfit for herself and then the red one for me.

'Here, try these on for size,' she said, chucking a tiny pair of underwear to me. They were bright pink and looked like they showed a lot of cheek but weren't a thong.

'You serious?' I said laughing.

'Of course I am.' She looked at me like I was the daft one. 'I've got you the matching thong for your little bag as well. A girl can't go out without a spare pair of pants. You never know what might happen. Plus, I thought these might provide you with a bit more coverage.'

I stepped into the knickers and slipped them up my legs, they felt incredible against my shaven body and they were all lace. My cock fit snugly in the front of them. Next came the bralette, same colour and once again, pretty much all lace. There was no clasp to this though, so I slipped it over my head into place.

'You've either been eyeing me up or measuring me in my sleep.' I said laughing. 'Everything fits like a glove.'

'Oh wow! Check you out with your little peachy bum,' she said laughing. 'Hopefully these will fit as well.' She reached into the bag and pulled out a couple of fake breasts. 'I thought you'd look good as a B cup.'

She wandered over to me and slipped the two breasts into the bralette, there was some sort of adhesive on one side as they stuck to my chest when she put them in. She left me to get the rest of my outfit on whilst she finished getting ready. I filled my tiny purse with my phone and other essentials as Claire came out the bathroom wearing a matching lingerie set, just hers was in orange. We were both ready and after calling an Uber, we were arriving at the student accommodation less than 20 mins later. Ready for a night of fun.

I was lucky that when I got out of the Uber that there wasn't any paparazzi hanging around, forgetting that I was dressed as a woman, I left the car in the most unwomanly way possible before Claire scolded me and told me that I needed to act more feminine.

We finally got into the house, and it was a lot bigger than I imagined. It seemed to be spread across 3 floors. When we arrived we were shown around quickly by one of Claire's friends. The ground floor seemed to be one giant communal area where the majority of the party would be happening. It had a large seating area and a small kitchen. Upstairs on the first floor, there was the dining area and 3 bedrooms, one of these was being used as the coat room, so we took off our jackets and left them there. I felt weirdly nervous but excited at being dressed like this in front of other people. And up on the top floor was another 5 student rooms. All in all, it seemed like a great place to live for Uni students.

We headed back downstairs and there was already quite a lot of people here. The drinks were flowing and Claire introduced me to all her friends from Uni and some of their friends. She always seemed to introduce me as Steph as well, which was confusing but then she smiled at me and winked. So I tried my best to keep up the female persona by trying to act more feminine. I was crossing my legs when I sat down, smoothing out my skirt. All of it was turning me on a lot. I had to stay seated at one point for a good 10 minutes whilst I waited for my erection to go away.

The party went by for a few hours, with lots of drinking and lots of talking. Eventually someone got the shots out which just added to the situation. Luckily I'm quite good at handling my drink, so by now I was only slightly tipsy. I'd also lost Claire at some point as the party began to spread out across the house. I was left with a few of her friends and we were chatting, they were eyeing up the guys in the house. Me on the other hand, I was keeping my eyes on the girls, hoping to catch any glimpse of their ass or their panties.

I could hear the girls talking about the different guys that were walking past, thinking about how big their cocks would be. Whether or not they'd fucked many girls. 'So what do you think Steph?' One of the girls asked me.

I was completely lost in my own world and also forgetting that I was actually called Steph this evening. 'STEPH?' She shouted again.

I quickly turned and apologised. 'Sorry, what was that?'

'Any of these guys take your fancy?'

'Ermm...' I stuttered. 'I can't say I've been taking much notice really.'

'Oh come on...' She playfully slapped me on the arm.

'I haven't.' I said laughing at her. 'Call me a Halloween nerd but I've been looking at the costumes more than anything.'

They all laughed. I mean it wasn't a lie. I'd always been fascinated by what girls at Halloween and I know I'm not one to talk considering how I'm dressed, but they all tend to go for the sluttiest costume they can find. Wearing bodysuits and stockings, nurse outfits, maids and the rest. There was a few times some of the girls bent over and the skirts were that short you could see the tiny thong that was resting perfectly in between their ass.

I was once again snapped out of my trance when the girls grabbed me by the hand and told me I had to dance. The furniture on the ground floor had been moved around so that there was enough room to have a bit of a dance. There wasn't a D as such but somebody had their laptop set up and was controlling the music. I wasn't much of a dancer so I'm not sure what quite came over me when I started dancing with the other girls.

We were grinding on each other, I was slapping the other girls on the ass when they were bending over in front of me. If Claire could see me now, she probably wouldn't even recognise me. I think the only reason I didn't have a raging hard on was because I was focusing on the dancing that much, I didn't have time to think about what was going on.

I was dancing very closely with one of the girls, we were trying to look sexy but being really silly at the same time. We kept shimmying ourselves down each others bodies, I was rubbing her stocking clad legs whilst trying to keep my legs as close together as possible. Then she did the same thing to me. It was fair to say that most eyes around the room were on me and the girls. As we carried on dancing, Claire's friend dropped into the squat position once more, only this time on her way up, she thought it would be a good idea to flip my skirt up to everyone and flash my panties.

I looked down and in a panic and her eyes went as wide as they possibly could. She was literally millimetres away from my cock and balls. She jumped back up and made excuses to leave the dancing and dragged me away to get another drink. I was really hoping Claire would come back and explain the situation.

'OH MY GOD' she said. 'You're actually Claire's boyfriend aren't you?'

'Yes, but please keep your voice down.' I pleaded with her.

'Oh my god, this is amazing.' She said, getting all giddy and clapping her hands.

After that, we discussed how Claire had managed to get me to dress up and how she convinced me... although I didn't need much convincing. Then Claire returned from wherever she'd been, chatted with her friend about my dressing and then she took a drink back upstairs where it was quieter whilst I stayed to chat to her friends.

We continued to drink and dance and before long, couples started to pair off. Guys and girls were all over each other. Kissing, dancing, some weren't even bothered about their surroundings. I headed over to the kitchen for another drink, where there was one guy who seemed to be on his own.

We got chatting and he seemed like a lovely guy. All the time we were talking, he seemed to be moving closer to me. It was getting late, and there was a lot of different noises that seemed to be filling the room. I had a quick look round and when I turned my head back towards the guy, he pressed his lips to mine and locked me in a full on kiss. I'd never kissed another guy before. But tingles went throughout my body and I thought I was going to melt underneath him.

I tried to break the kiss off as quickly as I could to see whether or not Claire was hanging around. She was still nowhere to be seen and I no longer knew what to do. I always used to fantasise about being with guys when I was younger, even more so when I used to dress. Was this a chance to live out this fantasy?

The guy leaned in and kissed me once more, only this time he had his hand around my waist and pulled me into him. His hand was roaming around the bottom of my back before he eventually gave my ass a squeeze. He began to feel my ass through the lace panties I was wearing before he tried to move his hand around the front. I patted him away quickly.

He broke the kiss and leaned in to whisper in my ear, 'don't worry, I know your little secret.' And he put his hand on my now rock hard cock in the front of my panties. I moaned into his shoulder and felt my knees start to go week.

'Should we go somewhere more private?' He asked me. I could only respond with a nod before he took me by the hand and led me towards the stairs. As we passed through the ground floor, there was various people in different states and it seemed like it was going to be a race to get a room before there was students fucking in everyone of them.

I let go of his hand as we made our way up the stairs in case Claire was sat chatting but as we got to the top, she was nowhere to be seen. I had no idea where she was or what she was up to. We tried the first room we came to, there was noises coming from the inside but he opened the door anyway. Seems like somebody had already beaten us to this room. It was still in darkness but you still make out what was going on. There was a guy hammering away at a girl in the missionary position. We couldn't quite make out who it was but could see the girls panties dangling off her ankle while she almost screamed from the pleasure. The guy I was with, quickly closed the door before they had chance to see us.