[shiftyj]

From 18 to an age I'm almost embarrassed to admit, "Halloween" for me meant going out to a club with friends, dressing up and hoping to get laid. I assume I'm not alone.

I succeeded only once, and it was a weird, weird, night. Since it's Halloween, and costumes play a part in my tale and the theme of this site I'll share, and start the ball rolling if anyone else wants to share their best Halloween story. The essentials of this are absolutely true, dialogue is as near as I remember it, some details changed to obfuscate till I decided fuck it- none of the people involved are ever going to read this site.

I was living with a male and female roommate, and I convinced them to have a Halloween party. I think it was my idea anyway. I mean, c'mon, my house - I can get drunk and have a place to get laid at and crash, right?

Jason was all over the idea. The other roommate, Mindy, was initially opposed but gave in.

We were pretty drunk when we talked this all out. Jason decided he wanted to go in drag and said he'd be a hooker.

Wait, did I mention we lived in a terrible neighborhood, and we actually had hookers on our corner at night? Some were even still out when I'd go to work in the morning. Yeah, we were all three pretty clueless whitebread kids just out of college and were still elbowing each other about hookers actually existing in this real world place.

Our roommate Mindy said she'd dress up and be his pimp. There was nothing for it then of course, but for me to be a hooker as well.

It was the 90s, I was goth (at least on weekends), all my friends were goth and I'd just read Gaiman's Sandman series. I decided I wanted to go as a goth hooker, looking like "Death," from those books.

I started asking around my larger, lady goth friends for costume pieces. I eventually settled on a costume of a tight black corset, long black skirt slip very high, stompy goth boots which I already owned, a black wig and an ankh necklace. I was fairly muscular back then, and the corset made my pecs…well, I had cleavage. I had good cleavage. I had nice legs too. I even shaved the top half of my chest, and the leg where the slit was.

I didn't shave the parts that wouldn't be showing because you know that would just be weird and getting into the part a bit too much. That's beside the point though.

Between the three of us we had slightly overlapping groups of friends so we expected it to be a big night.

The night of the party came. Mindy did my makeup early on. As an aside, if you've never had to stay completely still for 20 minutes while a gorgeous girl stares intently into your face from what seems like 3 inches away…well, that was a fun experience too.

Jason ended up looking like a blowup doll brought to life, and not in any sort of good way. I, on the other hand, was told I looked hot.

About an hour into the party I was very happy and confident. I'd also gotten a lot of double takes, compliments, and even several pinches and spanks on my ass from both females and males. The avowed man-sl*t of our group of friends kept giving me sidelong looks that frankly scared the shit out of me.

Let me tell you though, I got a lot of attention from girls I'd never gotten it from before. Some of it very confused attention.

We noticed fairly early that diagonally across the street another party was going on. I loudly proclaimed that I'd form a committee and investigate. I gathered a few people and we left to explore. Looking back, I can't believe I left my house at my own party. Stupid.

The other party was of course also a Halloween party, and though I didn't know the hosts I knew a few people there. I mingled, checked out the girls, took my compliments and got drunker. One group I was talking to mentioned there was another party on the block over, given by some other people I knew. I didn't realize they lived so close, and I set out.

The short of it was that from about 8pm to 1am I wandered between no less than four different Halloween parties. I got to a certain level of happy, confident drunkenness and was able to maintain it. You know, where you're certain you're twice as charming as you really are; or if you think for a second maybe you're not, what the hell does it matter?

It was one of the weirdest nights of my life. I randomly made out with one girl who just came up and started in, then left just as abruptly.

Looking back again, I can't believe I was stupid enough to walk around in that neighborhood, especially dressed like that. After a while I was walking between the parties by myself. I'm lucky I wasn't shot or worse. I did get catcalled by one of the real working girls on the block, which pleased me.

Other people were doing the party walk as well, and I kept running into a trio of girls whom I kind of knew. They were a perfect set: tall, medium and short. Tall was a gorgeous vampire and I hit on her every chance I got. Short was dressed as a Mario with stuffed overalls. It wasn't as obvious what Medium was dressed as.

I'd known Lisa forever, tangentially through other friends. She was a lesbian, tough acting, acerbic, and arch. A b*tch. Very intelligent, sometimes funny, but a b*tch. We'd bonded a few times at events by sharing a corner and mocking people. She was medium height, medium everything, short red hair, freckles and glasses.

She acted like that she didn't expect anyone to understand her costume. As I was writing this just now, I wracked my brains trying to think of what I could change this to instead of what it really was, but still keep to the essentials- but in googling I see lots of people have had her same idea since then (she probably wasn't the first to do it either) so I'm not going to change what she was wearing:

It was a one-piece item of white lingerie. The cups were lacy and semi-transparent. It made me look twice because I could plainly see her nipples through it. It was held up by straps on the shoulders, and it ended about mid-thigh. From the cups down it was opaque and had a mother of pearl shine. She'd written on it in magic marker a few disturbing things like, "I wish I had your cock," "let's kill dad," and then the dead giveaway, "and sometimes it's not a cigar."

Even in my drunken state, that last bit made me blurt out, "it's a Freudian slip!" Then I backfilled and out loud made the association with penis envy and Electra complex for the other things she'd written. She acted surprised and said I was the first to get it.

She gave me the once over from head to toe. By the way, I learned that night from her and other people how it feels to be constantly undressed by eye, or to want to say, "Hey, my eyes are up here buddy!"

"And what are you supposed to be?" she asked, taking in my corset, slit skirt and makeup; sure my costume must be an equally witty puzzle.

"I'm a wh*r*!" I proclaimed with the biggest, sappiest grin I could manage.

She looked me over, I swear she sniffed, and said, "Good job."

I gamely smiled and tottered off. I'd been trying to slink seductively earlier in the night but that ship had sailed after the fourth beer.

I crossed their paths later. The girl dressed as Mario told everyone around that Lisa wasn't wearing anything under her slip. I said neither was I (not true).

I wandered again through a circuit of the parties. There were a lot of good costumes and a lot of flesh on display. Even an honest to god coconut bra and grass skirt.

Eventually I made my way back to my house. No one was around except a small group having a smoke on my front porch. As I made to go inside, a werewolf with a cross-chest bandolier of Budweisers put his arm in front of me and said, "Party's over dude, the guys that live here said it was getting out of control."

I asked where Jason and Mindy were. He didn't know, but I found out later they'd hooked up for the first time.

I thought I'd have trouble getting into my own house. I didn't have my keys because I'd refused to carry a purse. Lordy, what would have happened if a cop had picked me up without ID? I didn't have any way to prove I lived there. I thought a bit.

I said, "Hey, I live here," and Beerwolf (as I found out his name a day or so later) let me in.

I walked in and tiredness hit me and I realized I just wanted to go to bed. My mission of getting laid had been a flop yet again, but I had had a good time, and I'd made out with that one girl.

It was a small, older shotgun house with lots of additions, and the living room flowed into the dining room into the kitchen.

Sitting at my dining room table, drinking (my) whiskey on the rocks from a tumbler, was Lisa. My only bottle of hard liquor was sitting by her at the table. She was leaned back in a chair, legs crossed like a man, idly turning left and right, without a care in the world.

I was too tired to be surprised. She raised her glass at me, and I plopped down across from her. I took my whiskey bottle and drank a swig straight from the bottle. Which was stupid, I hate whiskey, and was already drunk.

We made a bit of small talk about the night, and I think I finally asked where her friends were. I knew by now I really didn't have a chance in hell with her gorgeous vampire friend.

"They wanted to leave, I stayed. Mindy said I could crash here," she said.

I don't recall what I said, but I remember eventually she said, "Your makeup looks like shit."

I doubt I had anything witty to say to that.

"Here, get up, let me get it off you," she said. We got up, I followed her into my room, into my bathroom. I could see in the mirror I was a mess. All the black crap Mindy had put on me had ran, and the little eye curlicue that was supposed to look like Death from Sandman was just a streak down the side of my face. I think I made a joke about it being my party, and I could cry if I wanted to.

I let her wet a washcloth and she started cleaning my face. She tut-tutted a bit. On the one hand it felt so normal. She was doing me a favor, taking my makeup off. On the other it felt bizarre, like there was something kinky about it.

I also took the opportunity to look down her slip for a better look. I wondered now if she really wasn't wearing anything except the slip. I know she noticed my peering.

I was drunk. I asked without a second thought.

She answered "Yup," very matter of factly.

She finished washing the makeup off and said something like, "there we go," and walked back into my bedroom. I followed her.

As we passed by my bed she stopped so I almost ran into her. She turned around to face me, reached up and flipped her shoulder straps down, one at a time. The slip did not just fall off, she had to work at it a bit.

My mouth was wide open. She had the hairiest pussy I've ever seen, before or since. I know I stared probably too long. Her boobs were just slightly on the saggy side, and she had very hard, eraser type nipples.

It took me a second to completely switch gears and realize the situation was vastly different than I thought. I played for time a second.

"What's with your nipples?"

"It's lipstick," she said.

While I was still processing all this, she turned me around and started by unzipping the skirt and pulling it down. Then the corset hooks. While she was stripping me she said, again so matter of factly, "if you do a good job eating my pussy, we'll fuck."

"I thought you were a. . .I thought you hated guys?" I asked.

"I hate everyone."

She then, I shit you not, laid back and drank my whiskey with one hand while holding the back of my head with the other.

I apparently did a good enough job because then we fucked. She was pretty demanding, she knew exactly what she wanted, and how. The next morning I got her dressed in some of my workout clothes and took her home. We awkwardly hugged goodbye (probably not her idea) and never spoke of it again. She's been married twice. Once to a man, now to a woman. Mindy and Jason got together, I moved out, they're divorced.

Your turn.