A Dress up Party with the Girls

I stood there in the mirror, contemplating what I was about it do. Do you have what it takes to do this? I asked myself. At this point, it didn't really matter. I could hear the four giggling girls downstairs and despite only having arrived a few minutes ago I knew they had started the party quite a while ago and had already had a fair amount of wine.

But this is what dreams are made of isn't it? I smiled to myself. Sure, it was a bit of a strange predicament but there was no changing the fact that every one of these ladies was extremely desirable. I ran through the girls in my head. First there was Janelle: petite, quiet Janelle. There were rumors that the small quiet girls were the raunchiest but let's just say Janelle's history in that category was much less than rumor. Then there was Terri who despite her tomboy attitude was easily the hottest in the group. I reminisced briefly back to the time I had seen her at the Stampede dressed like a farm boy's dream in a red plaid shirt tied just below her sizable breasts leaving her belly button exposed to the world. And those daisy duke shorts with that ass... I felt myself grow a little harder just thinking about it. Then there was Lucy who had answered the door in a cute little tigress outfight with a tiger print bra and ultra short pink mini skirt, complete with a black tail that emerged suspiciously from under the skirt. Lastly, Kelsey who had invited me tonight in the first place. Kelsey was one of my best friends but I knew that she also had a mischievous side to her and had no doubt in my mind that she was the one that had orchestrated this whole thing.

And did I mention that these girls were all single and, from the looks of it, very ready to mingle?

I smiled once more as I gathered my nerves and opened the bedroom door.

================== Earlier in the day ==================

I'm a senior in college. You probably don't care about what I'm studying so we'll skip that whole part. Long story short I'm mainly still here because of my amazing friends that I've made over the last four years. Plus, quitting now wouldn't be worth it with graduation coming up in just a few months. At least, that's what my ECON 101 prof had assured us in first year.

I look up from my work in the cafeteria as I hear I familiar voice behind me.

"Hey you! How's it going?" The voice said. I turned around to greet it's owner, Kelsey.

A less informed person might think that Kelsey and I were dating, but unfortunately that was far from the truth. Although I had certainly started my relationship with her looking for more than a friend it never worked out. In fact, that was basically the story of my life. Most of my friends were actually great women like Kelsey who had befriended me while bouncing between boyfriends like pendulums. I loved them all dearly and wouldn't trade them for the world but just once I would like a girl that didn't see me for the gay friend they never had. Of course the worst part was that I'm not gay - I'm just really good at being friends with girls. Unfortunately despite my insistence on this matter I hadn't managed a single girlfriend all throughout college.

"Hey! What are you up to?" I replied. I hadn't expected to see Kelsey so late in the day. Usually she left after her two o'clock class.

"Oh not much, just about to head home actually but I wanted to find you!"

"Oh really, and why's that?"

"Well does a girl need a reason to find her best friend on Halloween?"

"Oh my god!" I exclaimed. "I completely forgot! Man with that mid-term this morning I wasn't even thinking about it."

"Well that's shitty, how'd the test go?" She asked.

"Eh, you know. The standard fair." I replied while miming a rude gesture. "But hey! Just one more semester right?"

She burst out laughing. "You got that right. Any plans for all hallows eve?" She asked, suddenly looking a little coy.

"Not that I know of. I usually hang out with Todd and the guys for Halloween, but.. Yeah not this year." She nodded her understanding. Todd was one of my best guy friends but ever since he had broken up with Janelle I had quickly learned that I was better friends with her and the way it had ended they had both made it obvious that I could only be friends with one of them at a time. "How about you? Anything planned?"

"Actually yeah!" She said, giggling again. "We're having a little dress up party for just us girls."

"Oh that sounds fun" I said, smiling despite the fact that I was hoping for an invite. Oh well. Halloween was overrated wasn't it? Honestly after that test today I wouldn't mind a quiet night home alone.

"Oh don't look at me like that!" She said, pretending to be offended. "Of course you're invited!"

"But didn't you say it was just you and the girls?"

"Well yeah, but you're basically one of the girls!" She winked at me, then checked her phone and stood up suddenly. "I've gotta run! But we're meeting at Lucy's place at ten! Don't forget your costume!" And with that she was gone, off running towards the bus stop.

I stared after her and started packing up my stuff. I'd have to run home and get ready if I was going to make it. It was almost seven and I'd have to eat, shower, and put together a costume.

A few minutes later I was on the next bus home. On the way I grabbed my phone and looked up costume shops but none of them were even close to my bus route and I didn't want to go far. Oh well, I thought to myself, I'll just throw something together at home.

I got off at the fifth stop and walked up to my apartment, dropping my stuff just inside the door as I got in. I quickly threw some water in the kettle to make some ramen (I know, how stereotypical college kid) and got in the shower while it boiled.

Coming out of the shower I sat at the kitchen table wrapped in my towel and started eating my ramen when my phone buzzed. It was Kelsey asking me to pick up some booze on the way. I replied that I would.

Having finished my soup I threw the bowl in the sink and went to look at my closet. The only costume I had was a pirate costume from freshman year. Oh well, not bad for a last minute costume.

I got dressed and came out to the kitchen to find that I had another message from Kelsey: "Don't come sober either! It's gonna be a fun night :)" I chuckled to myself. Kelsey always wanted to pre-drink. I decided to humor her and had a few beers while I watched some Netflix and waited for a half an hour.

Feeling a decent buzz I went out and hopped the bus. I got off a few stops later at a small convenience store and went in and bought a bottle of wine. I then walked the two blocks to Lucy's house and knocked on the door.

I could hear music and giggling inside but nobody came to the door. I tried the handle only to find it locked. I knocked a little louder. A few moments later I heard footsteps inside and the door opened.

I was greeted by Lucy who was giggling. She said something. I didn't hear it. I was too busy staring at what she was wearing. It was a little tigress costume with a black tiger print bra showing off her cleavage, and a tiny pink and black short skirt that I doubted really hid anything if she got walking. Topping it off was a cute pair of black cat ears that blended in with her black hair and a black tail that curved around her leg and appeared to originate somewhere under her skirt.

She was still giggling.

"Wha-" I started to ask, only to be interrupted.

"I said, it's not THAT kind of costume party silly. Didn't you get the memo?"

"Uh wait what? What memo? Kelsey invited me!"

"Well jeez don't make a scene! Come in Mr Pirate!" She said, still giggling. I acquiesced and stepped past her, trying not to touch her exposed form which she didn't even attempt to move out of my way. As I did so I could smell the sweet taste of Moscato on her lips. That explained the giggling.

"Follow me!" She shouted giddily and ran deeper into the house.

I slid my shoes off and followed her, unable to take my eyes of the tail emerging from her backside and holding her skirt up just enough for me to see the curve of her bum.

I caught up with her just as she turned the corner into the living room. The sight at the door hadn't prepared me for what I had just walked into. Sitting around the living room staring back at me, each with a glass of white wine in their hands, was Kelsey, Janelle, and Terri. And they were all wearing lingerie.

Kelsey was wearing a black lace halter dress that accented her tall tan body beautifully, with ties attaching down to black stockings that matched the dress. Terri on the other hand was wearing a schoolgirl outfit that left her ample cleavage tied together with a white shirt over a lacy red bra. The outfit was finished with a plaid short skirt and white thigh-high socks with red ribbons that matched the ribbons in her hair. Lastly, Janelle was wearing a black lace teddy with red trims and bows around her breasts. I followed her sensual hour glass shape down to her hips, but it wasn't till she turned slightly that I noticed she wasn't wearing black underwear. It was in fact a black strap on with a veiny black dildo anchored securely to her crotch. My eyes widened and seeing this she gave me a sly wink.

I couldn't help but stare. My mind was reeling. What the hell was happening? Was this some kind of joke?

Lucy turned towards me and placed her hands on my waist. "You look super confused Mike, but it's really quite simple. For the last four years you've been our very best friend. You've sat there and listened while we complained about all the assholes we dated and all the silly stuff that happened, meanwhile we didn't do a good jump of listening to you!"

"What do you mean?" I asked in a daze.

"Simple! We all assumed you were gay and were always introducing you to guys! But you're not gay are you?" I shook my head. "See! We didn't realize until too late!"

"But we did realize" she continued, "it took us a while, but we realized. And now look at us. We're all single because our boyfriends were jerks and here you are, still our best friend."

I tried to to digest what she was saying, but was having trouble thinking. All the blood in my body certainly wasn't in my head.

Janelle stepped up to me, standing so close that I felt the dildo brush against my trousers and her lacy breasts against my chest. "So we decided to have a little fun with you as a thank you. Well actually, first we had a little fun with Lucy" she said, and reached behind to give Lucy's tail a quick pull. Lucy closed her eyes and moaned, widening her stance a little, but Janelle didn't pull again. "But now it's your turn. And all you need to do is dress up a little because it's Halloween! Can you do that Mike? For all these beautiful girls?"

"I uh, I'm a pirate though.." I said, confused. They all laughed.

"Follow Lucy" Janelle said sternly and proceeded to sit back at the couch, where the three girls continued gossiping like nothing was out of the ordinary.

I felt Lucy's hand grab mine and she lead me out of the room and up the stairs. We arrived at her room and she opened the door. There was clothing scattered all over but what caught my eye was the three pairs of lingerie laid out on the bed.

She turned around. "Remember your reward Mike, it's really not much to do." She said, while her hand reached out and grabbed my bulging dick. "Not much at all for us beautiful girls."

With that she turned tail (literally) and walked out of the room, closing the door as she left.

===================================

I surveyed the three pairs of lingerie on the bed, still trying to comprehend what was happening. Did these girls really want me to crossdress in order to have sex with them?

Considering this, I instantly tore off my clothes. This was a simple decision. Honestly, four beautiful girls come to you wearing only lingerie and want to have sex with you, and all you have to do is dress up? That's a no brainer.

I stood naked in front of the bed. Now I just had to decide what to wear.

The first option was the classic french maid outfit. I disqualified it immediately for the fear that the girls would then try and get me to be their maid for the night. The next two options were very girly though. The first was a bright pink ensemble that seemed to include a lot of mesh material and straps. From what I could tell it was some sort of teddy. The last option was a white and red getup with a frilly white top, red short skirt, thong, and stockings. I decided to go with the latter option as pink felt a little out there.

I pulled the top over my head and, though it was tight, it fit. I then reached for the skirt and pulled it on. It didn't even fully cover my ass. Next up was the red thong. I slid it on and felt the strap settle in between my cheeks. It felt weird and... kinda good. As I had picked up the stockings I realized there was also a candy red collar with a bow on it, which I put around my neck. Lastly I slid on the stockings on each leg and attached the straps that emerged from under the skirt.

I stepped up to the floor length mirror. I looked a little ridiculous. There was an obvious bulge barely contained by the thong and my ass wasn't nearly covered. I turned to the side and noticed that the top somehow made it look like I had a bit of cleavage.

And this is where you came in. I stood there for a few minutes, gaining my composure, and preparing myself for what was about to happen. Growing up I'd heard about all the crazy shit that happened in college. Little did I know that I'd get my fill of it in one night.

With one last deep breath I walked to the door, opened it, and walked downstairs. I heard a hush fall over the group as I turned the corner and, deciding to be fun, struck a pose.

They all gasped and were on their feet in a minute. All of them except Lucy who was face down on the carpet with her ass in the air pointing at me with her hands handcuffed behind her thighs, revealing the tail but plug she was wearing. I could hear a faint buzzing sound as she sat there moaning.

They circled for a moment when Janelle spoke up. "I'm impressed! You're a sexy little bitch aren't you."

I blushed for a moment and felt my dick start to expand. The girls giggled and pointed as the bulge under my skirt slowly grew. The attention only made me harder.

"And she likes it!" Janelle exclaimed. The girls giggled more. "Now, stand up straight... Yes like that. Puff out your chest, and spread your legs a little." I complied. Instantly the position made me feel exposed. I could distinctly feel the thong between my ass and knew that everything was visible

Janelle circled me and tapped my ass. "Good girl! Now Kelsey, isn't there something you should be doing?" Immediately Kelsey knelt down, reached for Janelle's black strap-on, and began licking it.

"Well your intentions are good, but right now that's not the right one." Janelle said. Kelsey turned to me, looked up at me with wide eyes and a smile from the ground, and put her head underneath my skirt. She immediately pulled my dick out and started licking it.

"Now Mike, do you like what Kelsey's doing for you?"

"Mhmm" I moaned, trying to keep the pose I had been told to maintain.

"Good. Don't you think you should share?"

I looked down at her with pleading eyes. I didn't want this to end. She returned my gaze sternly.

"On your knees" she said. I complied. "Have you ever given a blowjob before?" I shook my head no. "Well every good girl has to start somewhere! Kelsey just showed you how it's done."

With that she extended the dildo towards my face. I looked up at her, unsure about what she was asking. Was this something a straight guy would do? I thought about the four girls in the room, all in lingerie, one the floor moaning from her butt plug. Yes of course! Suck a fake dick to have sex with four beautiful women? Just so long as there's no guys I decided it was still straight.

I tentatively started licking the dick but after Janelle prodded a little I started taking it in deeper. Porn stars certainly made taking a whole dick look a lot easier.

After a couple minutes Janelle pulled the dildo away and ordered me to lay on the ground on my back. She then ordered Terri to get me ready.

Terri came up to me and started jacking me off slowly.

"Now Kelsey," Janelle started. "Do you like having your nipples played with?" She nodded yes. "Well don't you think Mike would like her nipples played with?" Kelsey nodded again and kneeled over head, reached down, and started tweaking my nipples.

I unconsciously started moaning. Fuck that felt good. Why hadn't I known that nipples could produce this kind of feeling?

Janelle said something else but I didn't hear, then Terri's hand stopped stroking me and as I opened my eyes I saw Lucy with her hands now cuffed in front of her standing over me. Slowly she lowered herself onto me and we both gasped as I felt myself enter her. She started moving herself up and down and I was in heaven. I laid there and watched her beautiful body move up and down on my dick as her handcuffed hands rested on my chest just below my bra to hold her balance.

Then my view was eclipsed by Terri's uncovered crotch. "Sorry Mikey, but you can't just receive the whole night." Then she lowered her pussy onto my face and my vision was obscured as her skirt blocked everything else off. I inhaled and smelled her musky sex. I wanted to lick her so bad.

Immediately I started running my tongue between her lips, spreading moisture around. It wasn't long before everything was wet and I found her clit. I started playing with it with my tongue which took all my attention as Lucy continued to go up and down on me.

Terri started moaning loudly and felt another body lay across me and a tongue start to play with my left nipple. Shit that felt good. I stopped licking Terri for a moment but she squeezed my head and forced me to continue. I then felt a hand on my right hand which guided me up and behind someones thigh. I felt a pair of underwear with a big wet spot and realized that I was touching Kelsey's pussy!

Fuck this was a good day.

I pulled her panties aside and started fingering her. She must have liked it because the licking intensified on my nipple.

Then everything slowed down. The licking stopped and Lucy pushed me deep and stopped going up and down. I tried to look out and see what was happening but Terri grabbed my hair and pulled, telling me to keep going. I obeyed but then I felt a pair of hands inside my thighs pulling my legs apart. Then a hand grabbed my thong and pulled it to the side while Lucy started leaning forward onto Terri.

I realized what was happening just as the wet tip of the dildo touched my asshole. I tried to push the girls away but the three of them held me quite easily.

Slowly, painfully the dildo pushed in. Then it kept pushing. The pain was building and I couldn't imagine how much more I could take. How deep was the damn thing inside of me? I started squirming but just then I felt a pop and suddenly the pain stopped as the dildo sunk deeper.

Muffled by Terri's pussy, I moaned like bitch. It was like a switch was flipped. Suddenly it felt great and as Janelle started slowly pulling in and out I felt my dick twitch with every thrust.

I came. It was so sudden. I had never felt anything like it. It felt like suddenly an eruption had overtaken me and I experienced the longest orgasm of my life. I felt Lucy coming on top of me, which caused her to squeeze me and only made me come harder, longer.

Then it was over and Lucy stood up, my cum dripping onto my chest. I heard Janelle say something and Terri's crotch pulled away from my face giving me a wonderful view of her pussy and asshole. I craned my head to look above me and between Terri's breasts I could see Lucy's cum covered pussy and tail on the ground above me as Terri bent down at Janelle's instruction and began licking Lucy's pussy.