Me, Justin, & Halloween

I had a feeling my brother's Halloween party was going to be lame. I was right. Geek friends and high school drama club kids. I suppose that's why my parents even agreed to let him have it. He was a senior in high school and they knew by now that the kid couldn't get into trouble even if he fell head first into it. It was a chilly October so most of the costumed party goers were inside sipping apple cider and talking about Star Trek. I being the cool 25 year old I was at the time, stayed out on the deck chain smoking and drinking beer by the brazier. The fire was starting to die down and I debated my ratio of remaining beer versus the effort it would take to put another log on, when I noticed someone open then shut the patio doors. I was hoping they wouldn't come up but they must have noticed me smoking and like smokers tend to do, they decided we needed to smoke together.

When they got to the top of the steps of the deck two things struck me. First that this person was tall, nearly six feet tall. The second detail I noticed got my semi chilled blood a little more then slightly interested. Whoever this was, it was a her. I decided to play it cool but still sat up a little straighter and as I'm prone to when I talk I mumbled out a "hey." She was wearing a pair of black low cut Doc Martin boots, and further up her long legs she had on a pair of white and pink striped leggings. Her legs were skinny, but the pink and white rings around them made them look sexy. Above that she was wearing a pleated black short skirt, black tee shirt with a band I'd never heard of on it, and a old scuffed black leather jacket. I noticed she was pretty flat chested, barely seeing any breasts at all. As she got closer I noticed her start to take exaggerated steps and swing her hips as she walked. She had long curly dark hair and looked like she was wearing too much make up. She wasn't really pretty, her nose a little too long and her jaw a little too square, but she looked really familiar to me.

"Hey Jay, how have you been?" Her voice was deeper then I thought it should be and I started to sit up a little further in my chair.

"Do I know you?" I asked stupidly as I took a nonchalant swig of my beer.

"Yeah." and when she laughed I knew "she" was really a "he". "It's me Justin."

Justin had been my brother's friend all through high school until he turned 18 and dropped out midway through this year. I knew the guy had home issues and felt bad for him but at the same time I had always warned my brother to use his head around Justin. Justin wasn't a bad guy really, he was just immature and usually ended up doing something stupid. Secretly I had always thought he was gay, but that was never a factor in my opinion of him. I have my own "interests" but with Justin is was probably just another layer of stuff the guy had to deal with. He and my brother had pretty much stopped hanging out once he dropped out of high school. I was actually surprised to see him here.

"Man I didn't even recognize you dressed like that."

"Yeah well it's a costume party I figured why not." He cocked his head in exaggerated pose, shifted his hips and batted his fake eye lashes at me.

"Well for what it's worth I thought you were a chic coming up here."

"You'd have liked that wouldn't you. Some under-aged drama chic to warm you up."

"Not really. Her mom maybe." I laughed nervously and covered it with a swig of beer. I watched as his long skinny white fingers fished a cigarette out of a crumpled pack. He moved like a woman sometimes. He stuck it between his red painted lips and looked into my eyes and asked for a light. I could tell he was testing me. Seeing how comfortable I was with him in drag. I leaned forward with my lighter, lit his smoke, and he looked into my eyes for a brief second as I did it, before he leaned back in his own chair and crossed his legs.

"I can't believe I used to hang out with those people in there. They all seem so weird now. They look so young."

"Yeah well that was you a few months ago you know." He must have noticed a bit of an edge in my voice.

"Oh I'm not talking about your brother. We've always been cool. I mean the rest of them."

"Yeah. Yeah we'll people change you know." He looked depressed for a split second before flashing me a huge smile and jumping up theatrically to his feet and twirling around.

"Change like this?" He said and for the first time I noticed he was trying to pitch his voice higher.

"Well a Halloween costume isn't exactly what i was thinking of but yeah that's a change."

"Oh I don't do it all the time. Just now and then for fun." He turned around and flipped his skirt up a little in the back and I saw the bottoms of his pale white but cheeks.

"Uh dude. Please tell me your wearing underwear."

"I am silly. I've got on a nice black thong." He was pitching his voice even higher now and he must have noticed I was slightly uncomfortable. I knew he was doing it on purpose. I had absolutely no idea what else to say at this point, so I finished off my beer and reached down for another.

"What you don't think I look good? A few minutes ago you we're hoping I was some young girl that would be all impressed by your cool twenty something act up here. Thinking that maybe she'd come up here and you could get a hand job or something." As he spoke he moved his hips around a bit and walked towards me. I have to admit there was some truth to what he was saying.

"Justin..." I started when the next thing I know he spun around and sat down right in my lap. He arched his back and I felt his butt push down on my crotch. He put his head on my shoulder and spoke into my right ear. "A few more beers and you wouldn't even have known it was me. You can't tell me that my ass doesn't feel good right there." He was right. It did. My cock thought so to because it started to get semi hard.

"Dude..."

"Shhh." He put his left hand on the back of my head and spoke softly into my ear. "It's okay. You can pretend I'm a girl if you want. I like it that way." His breath was hot in my ear. His other hand went down and took my one of my hands and put it on the top of his thigh. It was cold, but smooth. He shifted his ass again and I felt my cock stiffen even more. "See you do like it. You like my ass sitting on your cock. I bet those drama club girls wouldn't do that."

"What if someone sees us?"

"I could barely see you when I came out. Besides you'll notice them as soon as they open up the door." He got off me and turned around and unbuttoned and unzipped my jeans before trying to slide them down over my hips. I pushed my hips up and he slide them down to my knees before sitting back down on my underwear. My cock fit perfectly between the length of his butt cheeks.

"Man your ass is cold."

"Is it?" He started rubbing it up and down the length of my cloth covered dick. He ground against it for awhile before leaning forward and sliding his thong to one side and sitting back down. "Is it still cold?" I immediately felt the heat from his asshole as he worked it up and down my underwear. My cock was rock hard at this point and leaned backwards into me and placed his hot butt hole of the tip of my fabric covered dick. I could feel the heat from it.

I mumbled out a stupid "Yeah", before he got off and knelt down in front of me and pulled my shorts down. Without any preamble he launched himself on my cock, taking it halfway into his mouth, biting it slightly then sucking it as he pulled off it. Then it was back in his mouth and his hand was around the base of it pumping it as he sucked it. I looked down at him in the dim light given off by the fire and he looked beautiful with my curved dick sliding between his red lips. He looked up at me and stared into my eyes and for the first time I noticed he had blue eyes that were actually pretty. His other hand rubbed the top of my hairy thigh with his smooth palm for a few moments before it dropped between my legs and started touching my balls. I started to moan a bit at this and he slowly and gently started pulling on the skin and pinching it.

Then he abruptly got up and sat back down on my dick facing away from me. He jerked his asshole up and down my dick and I noticed his arm was in front of his crotch before I felt this heavy warmth on my inner thigh and nut sack. He had taken out his huge semi limp cock and it bounced against me as he jerked my cock off with his ass.

"I want to fuck you." I told him.

"No. Not tonight." He replied breathlessly while he ground his asshole against me.

"Just let me stick it in once." I hated to sound like I was begging but my cock was straining for release.

He leaned his back against my chest and whispered into my ear, "Tell me before you come." He moaned with the sly feminine voice ever now and then, but it didn't take long before I was mumbling at him.

"I'm gonna cum." He immediately sat up and grabbed my dick and lifted up off me. He put my cock head right against his asshole and for just a brief second I felt the tip almost push into him. Instead I came and splashed a huge load against his hot asshole. I could feel it tense with each jet of cum.

He stood up and leaned against my shoulder to steady himself.

"Sorry. Legs are tired."

"No problem. Man. Jesus that felt good."

"Uh huh." he replied. "Messy though."

"Sorry" I mumbled. "Here." I took off my jacket and peeled off my flannel and offered it to him. Then I got myself put back together.

He took it and cleaned himself off. While he was doing this I saw at least half his cock stick out from under his skirt. It had to be nearly 11 inches when it was hard. He sat down in a heap and tossed my soiled shirt on the deck. Then he pulled a compact out from the pocket of his leather jacket and a tube of lipstick. After he fixed the damage to his make up he bummed a cigarette off me, which I lit quickly, and he blew the smoke out between his pouty lips.

"That was fun. I've been wanting to do that for awhile. I used to jack off thinking about you when I used to stay the night." He blew another puff of smoke out.

"Well I'm up for it anytime, especially if we can go someplace more private."

"Sure. Now that I'm 18 of course." he replied sarcastically.

"Yeah. Otherwise that would be perverted."

He looked at me seriously with those blue eyes for a long second before we both started laughing. I didn't know it then but Justin would be in and out of my life for the next 15 years.