This incident happened about 12 or so years ago at a Halloween party being thrown by some friends of ours. My sister April and I were both invited to this year's bash and we eventually agreed reluctantly. The two of us lead very busy lives and seemed to work endlessly at our jobs giving no thought to any kind of levity at all. It was to be a Halloween party and the additional notion of partaking in something as juvenile as showing up in a costume made us cringe even more so. But in the concept of NOT attending such close friend's gala seemed rude and made it even more difficult to refuse the invite. The two of us later spoke on the subject over the phone and agreed that we could both use a little break from the workweek.
"It could be fun!" April prodded and I agreed.
Maybe dressing up like a jackass and getting shit-faced for just one night wasn't the worst idea ever.
I had called my sister a few days before the event to pick her brain and discuss possible costume ideas. I had always been a slightly bigger fan of the holiday then her and my costumes in the past were always a bit more lavish then hers. We had considered a couples-costume theme but the concept might have been misconstrued by the other attendees. We were brother and sister not some married couple in their 60's after all. It seemed like the phone conversation took forever but to no avail. Neither one of us had any solid ideas for our costume conundrum. Before hanging up, we simply decided to just go our individual ways and just and chose something at random.
Uncertain as to what my sister had in mind to go as, I decided to peruse some of my costumes from the past. I had kept everyone so far through the years and there were plenty of items to mix and match. I still had a bevy of shirts, skirts, jackets, masks, capes, boots, wigs and make-up to choose from. The clock was ticking and I only had 1 day left to conjure something from the vast amounts of clothing set out before me. Inspiration had set in. The perfect idea and one my sister would never see coming. April always went overboard the few times she did actually dress in costume and I didn't want her to show me up especially now that we were adults.
I decided to go as a sexy female nurse. Nothing too slutty or revealing, just something a bit more on the traditional side. Nurse uniforms of the past seemed to be more alluring to me for some reason, so why not? I had a slightly more slender frame than most and I had dressed in feminine attire before. Somewhere down the line, I had acquired a white button-down shirt and a white skirt and pumps. All I needed now was the hat and a few props to complete the look. Purchasing the last remaining items from a child's pretend dress-up doctor kit at a local toy store, I rushed home to assemble the get-up and hurry to the party.
After several minutes of getting my red wavy wig situated and make-up applied, it was time to get dressed. I shoved some wads of tissue down the front of my sister's black and lacy bra I had borrowed some years back. It was a bit snug but it made for a bustier appearance. I threw on the shirt, slipped on the mini-skirt, sheathed freshly shaven my legs in the silkiest pair of white nylons I could find and headed toward the door. It wasn't until I had grabbed my keys that I realized I not only had to wear the white pumps out, but drive in them as well. It was kind of a turn on to be honest. Although I was a little concerned about explaining myself had I been pulled over for speeding or something.
Arriving at the party a little later than usual proved to be a bit more difficult to find somewhere close to park. I just knew I would have to walk down a block or two in a pair of 3 1/2 inch heels on concrete. I could have just taken them off and walked but I didn't want to take the chance of getting my beautiful hosiery ruined. I toughed it out and just walked, surprisingly well, all the way to the front door. I was soon greeted by the hosts who had clearly gotten the party going a little early already. It seemed like everybody in the room stopped and looked at me in amazement. There had to be over 4 dozen people there and no one knew who I was.
Later when my identity was finally revealed the entire house burst into laughter and applause. After accepting several flattering comments on my appearance, my thoughts turned on finding out just which one of the costumed attendees was actually my sister. We had planned to meet up outside at the same time to make our "grand" entrance.
After what seemed like an eternity of wading through the masses of drunken party people in outfits far sluttier than mine, I felt someone grab my rear end.
"I recognize those legs anywhere!" I spun around to see a small slender girl in what looked like some kind of sexy cat costume holding a large drink.
It was April and she was evidently celebrating early as well. We circled each other a few times checking out one another's garb grinning and admiring our choices. She hugged me and said "Is that my bra?" April started giggling maniacally as she compared our breast size.
The poor girl could hardly walk but kept shouting "We gotta get you a drink!" over the loud rock music. My sister grabbed my hand and expertly navigated me through the maze of people leading to the impromptu bar. I'm still not sure what it was, but she and another very busty gal, dressed as a slutty pirate, started pouring random liquids into a giant plastic cup and served it to me. I took a whiff of the brew and could feel my mascara starting to melt.
The two girls started chanting "Drink it! Drink it!" I took a nice sized gulp of the swill and it tasted like model glue with a hint of lime. It was terrible but it was doing the job. I was getting more wasted by the second.
My sister and I spent the next several hours of participating in the usual party activities. Several versions of classic and made up drinking games were being played in what seemed like every room in our friend's house. The loud music kept everyone dancing and gyrating around constantly. Colorful strobe lights and fog machines set in strategic areas gave the entire house a creepy, ominous vibe no matter where you went. There were people in an array of well thought out costumes drinking, eating, smoking and laughing from wall to wall. This party had all the typical earmarks of what could be labeled 'a good time'.
Once again, I had fallen victim to more of April and her friend the pirate girl Beth's inane concoctions as the night went by. Feeling pretty confidant after so much liquid courage, I decided it was time to set my focus on the female guests. Awestruck at the amount of insanely gorgeous women there, it was hard for me to set my sights on just one.
Every one of them was dressed in the minimal amount of clothing that passed as a costume. No matter where I looked there were large lace covered breasts being heaved upwards or long legs wrapped in fishnet stockings and stiletto heels. It was getting increasingly difficult to hide my apparent admiration for their attire in my mini-skirt.
For some reason the sight of all these scantily clad single women were just background noise to me and didn't seem to matter. Despite all the sultry garb worn by all the potential sluts, the only person I couldn't take my eyes off the whole night was April! I don't know if I was just infatuated with the sight of seeing her in such a seductive outfit but I couldn't stop starring at her petite little figure.
There was not much involved as far as the construction of the cat-like costume she donned. It was no more than a decorative leotard that encased her athletically tight body, a pair of high-gloss expensive looking dark pantyhose, and some simple black pumps. April's hair was long, dark, shiny, and seemed to bounce seductively whenever she moved. The light glinted off the sheen of her nylons just right and was almost hypnotic the way they contoured her perfectly sculpted legs and ass. I was mesmerized the entire time. I had always admired her enticing body, even when we were younger.
For a little while, I just made a few rounds and introduced myself to the ladies. Most of which I didn't even know and if I did, their identity was hidden. It seemed as if an alarming amount of them were intrigued in being hit on by a dude in a skirt and heels. Locking on to some of the girls who had way too much to drink, I began thinning out the herd. I engaged in a few brief make-out sessions, as well as some random heavy petting and groping. At one point even pirate Beth approached me and shoved her tongue deep down my throat. She had been friends with April since grade school where my crush began and I always thought she was smoking hot. Seeing her in that ruffled halter top and leather mini and thigh-boots was almost too much for me to take. It was a terrible costume.
I had to back off of Beth out of respect for my sister. I was quite sure that she would not be too fond of me fucking her drunken best friend at a party. There was no doubt in my mind that it would have been a sure thing. We were both hammered and it was definitely an excellent night for nudity and poor judgment. For years, Beth and I were always eyeing each other like hungry animals whenever we happen to meet up. In the summer, she would sometimes come by the house and go swimming in our pool with my sister. I could hardly wait to see her gorgeous bikini-clad body emerge from that water just soaking wet and watch the sunlight bounce from her curvy little frame in all the right places. I probably jerked off thinking of her my entire career as a teenager.
In that kiss with the slutty pirate girl, my only piece of solace was that I did manage to slide my hand under the back of her extremely tight skirt. I finally managed to feel her supple ass in my hand and it was everything I knew it would be. It was warm, very firm, and fit perfectly in my palm. We parted lips and just smiled at each other. Immediately after, Beth's face had a sudden look of intense concern. The girl then whipped around and darted towards the bathroom slamming the door behind her. What followed next were a series of noises and grunts that were unmistakable. Obviously, she must have poured too much liquid-celebration into her sexy little body.
I knocked on the door to see if she was okay and got a pathetic "I'm fine!" April pushed past me and went right inside. It was as if she knew exactly what to do and came to aid in her friend in peril. There was no doubt that this routine of theirs had happened before. Not sure what to do after that episode, I simply went back out into the crowds and began to mingle again. Somehow, another drink was put in my hand and I wandered around the place just enjoying the sights and sounds of everything around me. Despite the Beth's whole nausea episode, I found a bit of personal excitement that I had finally gotten my first taste of that sweet nectar I had been pining after for so many years. With any luck there would be more to come, just not this particular night.
I kept running into another random party guest that night. Just some guy with his date who appeared miserable the entire time. I didn't know him and never found out who he was, but he was ironically, dressed as a doctor. This guy was very, very interested in exactly what I was wearing right down to color, size, and how I put it on, The doctor kept firing a barrage of strange and personal sex related questions about my attire at me. I think I was to lit to see he was hitting obviously hitting on me. I made it very clear I was a male but it didn't seem to matter and I just couldn't shake this guy.
At one point, he lifted the back of my skirt and explained that he wondered if i was wearing pantyhose or stockings. For the rest of the night I just teased him in suspicion of him pulling me into a closet and fucking me in the ass. Admittedly, I had already consumed more than enough alcohol and began to entertain the thought of being violated while in drag by a stranger. I wasn't sure if I would have liked it but it had been something i wanted to experiment with, even once.
April finally caught up with me and she was giggling the whole time. I was almost afraid to ask. "What's so funny?" I sputtered already knowing the answer, "Beth told you we kissed didn't she?" April started to laugh harder. I was not amused.
