The Fancy Dress Party

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

After dinner, Jess, said. "Can we practice getting your look right again tonight?"

After the wild sex of the previous evening, my answer came quickly. "Hell yeah."

I went into the bathroom to shave and I was nearly finished when she walked in. Her body snuggled close behind me as her chin rested on my shoulder. "Hhhhhmmm hey sexy."

She kissed my lightly on the shoulder, pushing aside my T-shirt. Her little kisses built up, and I sensed she wanted to say something. "All right Jess, spit it out. What is it you want to say?"

Hesitantly she whispered. "You'll think I'm weird."

"I will if you don't tell me what do you want."

"Promise not to get mad?"

"Come on Jess, you're driving me crazy. "

"Okay, would you shave your legs for me?"

"What."

She sighed. "I knew you would think I was weird."

"I don't think that. I'm just confused, curious. The question is why?"

"Well last night, was surreal, I absolutely loved it. I have always been curious what it would be like to be with a girl."

"Why the leg shave?"

"The only thing that spoilt last night, was your hairy legs."

She gave me that pleading look. "Please?"

Terrified I groaned. "No, sorry Jess, but that's too much. Gee, I let you put the bloody makeup on me."

There was that sulky pout again. "Please, babe. Think about how much fun last night was."

"No, look Jess, this is pushing the boundaries for me. Shit, I'm really uncomfortable."

"Please, what's the big deal? Divers, and cyclists, runners, they all shave their legs. It's not a big deal."

God knows why, but I relented. I decided to do it in the shower. If you've never done it you wouldn't understand. It's bloody difficult. Jess walked in a few times to check on me and laughed her head off. In the end I said.

"You wanted this, well come and help."

She smirked evilly and said. "Okay, you asked for it."

She stripped quickly and was soon in the shower with me.

She knelt down in front of me, with my dick bouncing around in front of her face.

"Will you get control of that thing." She laughed.

I shrugged. "Hey, this was your idea."

She ignored me trying to slap her cheeks with my swinging dick. God she even made me turn around while she shaved my bum.

When she stood up in front of me, her hand dropped down and she grabbed my dick, her fingers curling seductively around it as she gave it a squeeze and stroke.

I leaned back against the tiled wall as she played with me. I sort of zoned out, my eyes closed.

They came open quickly when I realised she was shaving my pubes.

"Hey, what the fuck Jess!" I spluttered.

She just gave my knob a big kiss. "Close your eyes again."

With a shake of my head I got my own sneaky plan.

When she finished, I grabbed the razor. She gave me a nervous look. "What are you doing?" She squeaked.

"Well you know the old saying, about the goose and the gander." I soaped up her pussy and let the razor glide over her short curly pubes.

"Bastard." She sniggered.

The sex that night was off the wall. It was everything the previous night was but more. She always liked to suck my dick, but never like this.

I repaid her hard work, and it felt different, she was so smooth, so silky soft. And the sex, oh my god. I thought I was going to have a coronary.

The next day we went through the whole process again and when she asked if she could shave my whole body, I put up no fight at all. It did feel pretty good actually.

It was Friday when I got home late. I always stopped off after work for a few drinks with the guys from work. It wasn't bad, just some drinks and a few laughs. It did however mean I was late home.

Jess was in a pretty happy mood. I had completely forgotten about the party and the fact she was supposed to pick up my costume.

She was in such a cheeky sexy mood that we ended up in bed early and the lovemaking seemed to have gone up another level.

Saturday was normally a work day for me, but Jess had pleaded that I take the day off, and just chill out with her. That would be fine but she headed off mid morning to get her hair done.

I took the chance to drag out my bike and go for a ride. Lately with long hours at work. The only day I got out on the bike was Sunday, so this was a treat.

I met up with a couple of mates and we went for a ride out through Maraetai, and back through Beachlands.

It was almost three PM before I got home to find Jess in a real tizzy. "Where the hell have you been?" She yelled.

"I went for a ride. What's the big deal. You weren't here anyway."

"But I was home hours ago. Now we will have to hurry."

"Hurry," I checked my watch, and it was only three PM. "What's the bloody rush?"

"Silly, we have to get you ready." She struck a pose and said. "Ta da. Do you like?"

I nodded. She did look very pretty. Her long golden blonde hair shone brilliantly in the afternoon sun. "Very nice." I nodded.

She leaned in close, stuck her nose into my armpit and waved her hand across her nose. "Phew, shower first I reckon."

I showered, and she poked her nose in and said. "Remember everywhere."

I was going to anyway, but her making it an instruction made me uncomfortable.

Once I was dried off she waved me over to the dresser where she started to apply long false finger nails. "Oh come on Jess. Is this really necessary?" I griped snarkily.

"Oh, don't be a sook. Humour me. If you're going to dress up, then lets do it properly. Wouldn't it be nice if you're the best looking hottie there?"

I laughed, that was a ridiculous statement, and I told her so.

She shook her head. "Don't undersell yourself. You look pretty convincing all dolled up."

She did my nails, putting on super long false ones. She applied coats of bright red nail polish.

I thought that was it, but no, then she started on my toenails.

That led to the next stage, my makeup. She had it down to a pretty fine art after four days practising.

When she finally finished I was even more shocked than usual. She had managed to make me look half reasonable. I mean, there was no hiding I was a man, but it looked pretty convincing.

As she sat back to admire her handy work she said. "Wow, Ru Paul, you better look out honey. Because Dan is coming."

As I stood up she quickly unpacked some white stockings, and passed them to me. "Here, put these on."

I can only imagine what I looked like as I stood there staring at her, my mouth hanging open. "Come on Hon. We haven't got all night." She groaned.

She got out her black fishnets and said, "Look, just follow my lead, okay."

She sat on the end of the bed and coiled up the stockings and then rolled them sexily up her leg. "Come on babe."

I followed suit and rolled mine up my leg. As the nylon slid up my leg, I got a little chubby on. It did feel sexy. I can't describe the feeling of those stockings sliding over my skin. It may be one of the singular most erotic experiences of my life.

We finished at the same time and she threw me a tiny little pair of white silk panties. "Oh my god. Surely you don't think I'm wearing them?"

She nodded, as she held up her own. "Look, they're the same as mine."

"Christ Jess, you're a bloody woman."

She sniggered. "Yeah, and so are you tonight." That made me flinch. God this thing was getting real. She pulled up her slinky panties. Damn, she looked beautiful. I did as she asked, but it was so embarrassing pulling up my panties. I could feel my manhood shrinking the further up my legs the tiny silky things slid.

The fact she watched on with a constant smirk on her face didn't help.

She handed me a tiny little white blouse thingy. I held it up against my chest as she giggled at my look of shock. It was so low cut. "Stop mucking around and button it up."

Shaking my head I did as she asked. With it buttoned she handed me a corset. It was black and looked like it was a lace up thingy. It dangled in my hand as I held it up. "Oh good god. Bloody hell Jess. What have you got me into."

"Shut up, and stop your griping. It's just a bit of fun." Just a bit of fun, god damn, I was getting sick of hearing that little gem.

She helped me pull it around my waist and started lacing it up. The laces were in the front. God talk about a stomach cruncher. With every tug from Jess, I could feel the bloody thing squeezing me tighter and tighter.

The corset fitted up under what was supposed to be a bulging pair of tits but of course I had nothing to hide. I was also getting nervous as this thing in no way resembled the costume I had agreed on. Where were the sleeves, and the long dress?

"Jess." I spluttered. Where's the rest of the costume?"

She winced. "Sorry Honey, that one was gone. This was the only one left. Sorry, but you're just going to have to suck it up."

If I was feeling nervous before, when she handed me the tiniest skirt I had ever seen in my life. I nearly freaked out.

Up until that moment I thought, yeah, I can do this, but right at that moment, all those thoughts went up in smoke. I was totally beat. I stood belligerently as I shook my head. "No way Jess, no bloody way. There's no way in hell I am going anywhere dressed like this."

She looked crestfallen. "Just pull up the skirt, please. Let me see."

I pulled it up and she knelt in front of me and hooked the garters up to the stocking tops. The garters had little black silk bows, which highlighted them even more.

She pushed me over too the wall mirror. I stood there feeling shocked, scared and completely ashamed. What the hell was I doing. I stumbled backwards, grabbing the wardrobe door for support.

Jess walked over. "Pretty sexy huh Dan."

"Pretty bloody stupid. I'm sorry Jess. I know I said I would go, but there's no way I can go anywhere dressed like this."

She spluttered. "No, no, no. Dan, I have been looking forward too this all week. Please, honey."

"Fuck, look at me Jess, I look like some kind of tranny freak. There's no fucking way I'm going out in public."

She gripped my hand in both of hers as she whispered. "Dan, every man and woman at that party is going to be dressed in the same way. You would stand out more if you walked in dressed in your normal clothes."

I could feel my heart pounding in my chest as I tried to get control.

Jess, still held my hand, her top one rubbing mine. "Dan, look at me. I feel just as nervous as you do. I have never in my life worn anything like this."

"Then why do it? We can stay home and keep our self respect. Why should we humiliate ourselves? Let Paul make a fool of himself if he wants to. Jess, we have nothing to gain from exposing ourselves like this."

"Dan, if we were going to be the only ones. I would agree, but everybody will be dressed the same. I know a lot of the men going to this party, and let me say this. You will be the best looking guy in the place."

"Oh lucky me. The best freak. Fuck that Jess."

I sat back on the bed, my head spinning. Jess came and flopped down heavily beside me. With a resigned sigh, she murmured. "Oh well, bugger. I just wanted to make some new friends, have some fun."

She looked so sad as we sat there silently. "Guess I got my hair done for nothing." She sighed.

Shit, she looked disconsolate. So damn sad. I watched as she gave me a sullen look. She stood up and started to get undressed.

God knows why I said it, but I whispered. "Oh damn it. Don't get changed, we can give it a try."

She jumped into my arms. "Oh thank you Dan. It will be fun, I promise. Some how I will make it up to you."

We finished getting ready and she knelt down and slipped on my shoes. Sparkly platforms, about three inches.

"Stand up babe."

I stood and walked. Being platforms they were at least stable, although it was hard to walk. My ankles ached just walking across the room. Jess finished putting on her costume and we stood side by side. She glanced sideways at me. "I think for tonight, I will call you Dani. Sweet sexy little Dani."

I practised walking while she rang a taxi. She giggled as she watched me stagger around the room. Her phone buzzed, announcing the taxi was downstairs waiting. "Are you ready babe?"

I nodded. "As I'll ever be, I suppose. Jess, you owe me for this."

She gave me a peck on the cheek and smiled. She swung back the door and we stepped out into the hallway. The taxi driver gave us quite a stare as we climbed in and Jess gave him the address.

The whole way there I could see him adjusting his rear view mirror so he could watch us. I felt like I was nothing more than fresh meat at the deli.

I realised, I didn't have my wallet. Jess saw my discomfort as she reached into her purse and pulled out some cash, to pay the driver.

We walked up the driveway to a very posh house in Remuera. It was big and flashy as were all of the cars in the driveway. Merc's Beemers, Audi's.

We stood at the front door and Jess gripped my hand tightly. "Here we go babe. Are you ready?"

She reached out and pushed the bell. I realised she was as nervous as me. We could hear the thumping drum and bass pounding out from inside.

We waited a few minutes before the door opened and there standing in the door was this massive guy dressed as Frank N Furter. His costume even skimpier than ours. He had a certain grace, obviously not embarrassed at all by his attire. "Jessica, how lovely to see you." He leaned down and gave her a kiss on the cheek."

When he stood up he turned to me. "And you must be Daniel." His hand reached out and we shook hands. I noticed, his fingernails were longer and redder than mine.

He stood aside and waved us into his home. He was a big guy, tall and muscly, athletic. He turned as we walked in. "Jessica, may I say you look wonderful. Fabulous costume."

Jess said. "Thanks Paul, you look pretty hot yourself."

He smiled in acknowledgement. "Daniel, I have to say you look absolutely gorgeous. Jessica said you were nervous. Well I don't understand why. You look divine."

Jess jumped in. "Paul, tonight, we decided Dan was going to be Dani."

With a soft girly voice, he said. "Oh wonderful choice. It suits you." He gushed as he stared at me. "Dani it shall be."

As we walked into the main room, the music hit us like a wall of noise. It hit you on the chest, reverberating through your whole body.

Paul walked us into the throbbing throng of about fifty people, some dancing. Some milling around in small groups. I was stunned. If I thought what we were wearing was risqué, well I was shocked to find we were probably the most conservatively dressed.

Looking around the room, I struggled to see whether some party goers were men or women. Jesus Christ. What a show.

Jess gave a squeal and ran over too a bunch of what I supposed were women. As they kissed and hugged, she waved me over and introduced me. I was wrong, they weren't all women. One was Another male dentist from the practice. I went to shake Andy's hand but he leaned in and gave me a hug and a kiss on the cheek.

He was dressed as a naughty school girl He wore a midriff baring white blouse, tied at the front. A tartan mini skirt that showed of his black seemed stockings. He steepled over me, in what must have been five inch stiletto's. His wig was long and glossy black. His makeup was incredible. Obviously professionally done.

He said in a very sexy husky voice. "Come on over and I'll get you some punch. You're going to love it."

Jess and I picked up glasses and dipped them into the punch bowl. I took a sip of mine, and shivered as the powerful alcoholic beverage filtered through me. "Bloody hell that's strong." I gushed.

Jess, who had taken a large gulp as well, was trying not to wince to hard. The fact her face was contorted into a deeply etched mask, made it hard to hide. Once she swallowed she said loudly. "Golly, that is dangerous." It didn't stop her from having another sip.

Andy picked up a plate that had little chocolate slices. "Have one of these as well, it takes the edge off."

I took a little nibble, god it was sweet, but it did make the punch a little easier to take. Jess leaned in close. "What's it like?"

I slid what remained of my slice into her open mouth. She chewed slowly as she delighted in the sweet raspberry and chocolate flavours. She had hardly finished when she reached for another. As we stood looking around the crowd I whispered. "Good god, look at this lot. I can't tell the men from the women."

"Yeah sorry sweets, but you are not the sexiest girl here tonight. Take a peek at the girl standing by the door. The one dressed as cat-woman. That is Desmond. He is the radiologist."

I was stunned, he was wearing a skintight latex suit, which covered his body showing off a very feminine curve. His arse stuck out, just like a woman's. The knee high patent leather black boots, must have had a four inch stiletto heel. God knows how he walked in those.

"Holy shit, that's a guy?"

"Yes and I notice he is giving you the once over."

Shocked at her blatant sexuality. "Stop it." I rasped sarcastically. "He's looking at you."

She gulped down her punch and dipped it back in the bowl for another. I mumbled. "Careful, that is bloody strong."

She smiled, leaned against me and whispered. "Relax, we are among friends. Let yourself go for once, enjoy."

Andy came back with a tray, on it were little coconut covered treats. They were only tiny. Jess took one and chomped it down quickly. Seeing the delighted smile on her face I decided to try one as well. I was finishing mine when Andy said, in a shocked growl. "Wow, slow down Jessica, those are pretty good."

She finished her second and said. "I'm going to go and talk to Paul for a while. Have fun baby."

Andy gave me a little smile. "Come on, you can help me deliver these."

I still felt self conscious, but followed him meekly as he wandered around the group. Well, he glided effortlessly, and I staggered behind him. He introduced me, as we went. I tried to look casual, walk tall, but the bloody shoes made it almost impossible.

On more than one occasion, I had to grab and hold Andy's arm for support.

We got to the other side of the room where, Desmond, the radiologist was standing. God he looked so much like a real woman. His figure looked so convincing, so shapely. I tried not to be to obvious as I let my eyes run up and down his body.

He was quick though and noticed straight away. He smiled almost sneeringly, his camp squeaky voice purred. "Hello darling, I'm Desiree, and who might you be?"

Andy replied laughingly. "This is Dani, isn't she divine?"

With a pronounced purr Desiree replied. "Very sexy, I love the costume my dear."

"Thanks." I stuttered. Suddenly feeling very intimidated and vulnerable. I kept tugging at the bottom of my skirt, trying in vain to keep my knickers hidden.

Andy chuckled at my attempts. He spoke to Desiree, "Seen anything that takes your fancy Hon?"

"Only this delectable little creature." he purred.

"Trust you." Andy replied.

Feeling very embarrassed I sunk what was left of my punch in one long gulp. Guess I was getting used to it. Andy saw my empty glass and said. "Stay here, I'll get you another." Desiree and I watched as he strutted like a supermodel to the drinks table.

"God, look at that arse. Beautiful isn't it?" Desiree whispered.

I swallowed hard trying to hide the shock. Desiree started some small talk about what I did, where I was from. The usual stuff. I was nervous, and feeling conscious of what I was wearing. All around the room there were couples, dancing and some of it was suggestive. Lots of grinding and close bodies.

There was laughter everywhere, the hub bub of conversation. Andy arrived with a tray of glasses. As he neared Paul and Jess arrived. I noticed that Paul was guiding her, with his hand resting on her arse. The smile on her face allayed my fears that anything untoward was going on.