After a three day weekend in Vegas the cross I wear around my neck and my wedding ring became the costume of a character I had always pretended to be. I hadn’t been there previously and when I got the chance to travel there for work I was psyched to do it. My wife thought it was nice they were trusting me with the opportunity and thought it could lead to a big promotion in my company. I was wary of what I knew was ahead of me though.
Men could get raunchy, and business men were the worst. I had taken clients out to strip clubs and bars, got them laid but had always avoided cheating on my wife for the most part except when one stripper forced her tongue in my mouth once but then I got out of that pretty quickly.
Guys talk. They brag about anything and everything they did and didn’t do. I had learned the cadence and the vernacular to fit in any situation but I didn’t really mean it. Even though I said all these things I thought of myself as being sexless and committed.
So three days would be hard but I had gotten through lots of situations before. And really once I committed I wasn’t backing out.
It was a long drive from L.A. with my assistant and he had come prepared as he had been there before with his previous boss. We loaded a rental car at my house with our bags, snacks and a cooler for the road.
He was casual about the whole situation. He kicked off his sandals as soon as he was in the passenger seat and reclined with a sleep mask and a family size bag of Cheetos that he rested in his lap. He ate whatever he wanted but he was skinny. And young, much younger than myself. So capable at his job I wondered why he hadn’t been promoted.
We listened to Sirius radio half of the time until he grew bored and pulled his MP3 player from his pants pocket and told me he’d put on some tunes. “Just hit shuffle,” he said. I adjusted the cruise control and worked to plug in the player. I hit shuffle and obnoxious rap began to play. Stuff I wouldn’t really listen to but I couldn’t deny it sounded good.
Even if it was obnoxious it seemed appropriate and I went along just like with every other situation. When we got to the city it was evening and the sun had begun to set. My assistant, Brad, pulled off his sleep mask and sat up. He grinned at the neon lights and said it was his favorite city in the whole wide world. I asked him if he had been to very many cities of the world sarcastically and he shook his head at my cynicism and said that he had. I was impressed.
He knew the place well enough that he gave me directions to the hotel. When we got there he was quick to find someone to help with the luggage and told the valet just to park the car on the side because we would be back out in five.
Five what? I thought. But it didn’t matter. It was his show so I went with him to the counter where we checked in and then up to the room with the bagman behind us.
When we got to the room he pushed open the door and began to turn on every light. I walked in to find that he had gotten a suite for us. But then I was instantly disappointed when I found there was only one bedroom then when I went in there I was shocked to find only one large master bed.
The bell hop right behind me smirked at my shock but when I turned on him he cleared his throat, setup the bags and held out his hand for a tip. Brad had already begun to strip down and was in his underwear before I could get the money from my wallet. In my anxiety I handed the man a five dollar bill.
The bellhop pulled the door closed and I looked back to Brad who stood at the window in a pair of briefs scratching at his side lazily. He was as skinny as I thought and I could make out his ribs and spine easily. One foot went up against his other calf to scratch at it and I could see the cleft of his buttocks easily.
He was my assistant but I was shocked by his brazen attitude and decided that I was still the boss so I told him to get dressed.
“In a minute,” he said. “Come here and look at this view.”
I walked to where he stood and was instantly taken with the view.
“Tonight we go out to have some fun in this city,” he said. “Get dressed in your second best suit while I go shower.” He dropped his underwear right there and walked away from me.
I looked after him partially in shock but also a bit angry only to see his buttocks jiggle nicely as he walked. A skinny man with a nice ass, I thought, such a weird sight.
I looked around the room and suddenly became embarrassed about the way he treated it like a locker room. It was too nice. I was about to pick up everything when I thought it would make me look like his assistant instead of the other way around.
His casual nudity and being inconsiderate was a new thing for him. He was never like this at the office so I decided that when he got out of the shower I would talk with him. My second best suit, I thought. I went about unpacking all of my clothes and hung my jackets in the closet before I remembered there was only the one bed and a couch out in the main room to sleep on.
Maybe we’d flip for the bed or else I could pull rank and make him sleep out there. I finished unpacking and stopped to listen to see if he was still in the shower. When I heard the water still running I decided it was the best time to change. What kind of night did he have planned?
Gambling, drinking, and girls all came to mind. I made quick work of putting on my second best suit and had time to check my hair in the room’s mirror before I heard the water stop.
I remembered that the last time I saw him he was naked and not wanting him to think I was waiting around in the room to check him out or else see him naked I decided to head to the main room. I looked over the amenities. Five dollars just for a bottle of water!
I was reading the room service menu and looking out at the city when I saw his reflection in the window. He had a hotel towel wrapped around his waist and his body was still partially wet. His hair wasn’t dry. He went to the mini bar and got two glasses and a bottle of Scotch that he brought over to me at the desk by the window. He went back for ice and quickly poured two drinks. I still had the menu in my hand and looked at him with suspicion as he handed me the glass of liquor.
“Sorry for being such a jerk but I just get so excited when I get here. Don’t worry I’ll clean up before we leave because it’s always nice to come back to a clean room.” He raised his glass and I was taken with his sincerity so we clinked glasses. “Here’s to new times and fun.”
“To new times and fun,” I replied.
We each took a deep drink, then he went about the room, as he had said he would, cleaning up after himself. He even took our glasses to the sink and put away the bottle. He was taking so long that I turned on the television.
Things were fine again until he stopped in front of the screen while I was watching the news report and pulled his towel off, then began to dry his hair, patted at the rest of his body. I could see him from the side and make out his limp dick, a few inches flaccid, and his black pubic hair that gleamed with dew.
I told myself it wasn’t gay to look. I had checked out guys all the time and they checked me out too. It was a guy thing ever since I was in high school to see what the competition was like.
It gave me comfort to know that there was this thing that God made different for everyone in length and girth when limp or hard as a rock. And dicks didn’t look like the people they were attached to. I knew many handsome men with small ones and average guys with big ones. He slung the towel over his shoulder and walked from the room. I saw his muscled ass and I rolled my eyes.
It didn’t take him long to get dressed after his little show. By the time he was ready though I felt like I was being dragged along, though the feeling vanished when we got to the first bar in our own hotel. We had a few drinks but the place wasn’t very busy so there weren’t many people around. He looked like he was on a mission and I wasn’t surprised when he told me we were going somewhere else. The second bar at the hotel next door was a little more lively with a karaoke machine and amateurs trying to sing their favorite tunes. We only lasted a few drinks there before he said he was calling a taxi for us. I tried to protest but his youth, his enthusiasm, was overwhelming.
That’s how we ended up at the bar that would change my life. The place was crowded, a mix of heterosexual couples and gay men. I thought it was a little odd at first for him to bring me here, especially when I saw the drag show, but then he gave me a drink and we found a table near a group of men and women. I looked them over and figured there were at least a few women who might be heterosexual, especially when they took note of us, well Brad.
“I signed you up next, the guy behind the bar said it wouldn’t be difficult to get you a dress and some makeup,” he said.
“Very funny,” I replied. “A few more of these and I might just do it.”
I was feeling pretty drunk by the time I took another sip of my drink. I knew I had to eat something so I looked around for a menu. There wasn’t one. Impulsively I got up from my seat and headed to the bar to ask the bartender. He handed me a few bowls of snack food. I wanted something more but took them anyway.
When I got back to the table with Brad I almost walked past it because two other people were sitting there with him. He motioned for me and I looked at him confused before I realized the place was crowded. I moved to the empty chair and sat with them. Brad leaned close to me, his lips at my ear.
“These are my friends Tucker and Pete,” he said. “They just stopped by for a drink. Do you mind?”
I looked to Tucker and Pete who seemed preoccupied with the show. They looked harmless. Boy, was I wrong. They talked with Brad and drank. I started eating my snacks. I felt like a glutton and selfish so I offered them to the table. Brad slid my drink to me.
“Finish this and I’ll get you another,” he said.
I picked up my drink, looked over the amount inside, braved myself to what I would feel, and downed it. Brad left for the bar and I looked to the two men at my table. They looked back to me and for a moment I thought one of them was going to speak but they didn’t. I was thankful when Brad returned and broke the tension.
Despite my snacks the next drink began to hit me hard, or else it was all the ones before catching up with me. I asked Brad if we could leave and he said we could. He told Tucker and Pete, both of whom looked disappointed and whispered something back to him.
“Do you mind if they come back for a drink?”
I just wanted out of there and anything sounded good as long as it meant I was getting to my feet and back to my room, back to my bed.
“It’s fine,” I said. “Let’s get out of here.”
I looked around at the table as they finished their drinks, then began to get up. I thought about sobering up so I decided to down my last drink. I got my feet and started to follow after them. I was okay until they stopped and I ran into Brad. He laughed me off, put my arm around his shoulder. He escorted me out to the parking lot where Tucker said he had a car. Brad led me to the backdoor and helped me inside before going around to the other side. He helped me buckle my seat belt before I stretched my head back against the rest. Tucker seemed to drive fast, hug the curves. I let out a moan and closed my eyes.
It wasn’t really sleep and when they pulled up to the hotel I sat up and opened my eyes, smiled at the sight. When I struggled with the buckle Brad released it for me. I got out slowly, closed the door and leaned against it. Tucker handed over the keys to the valet and Pete looked to me with concern.
“I’m alright,” I said.
“Let me help you,” he replied.
I started to push away from the car but realized I didn’t feel good. Pete and Brad on either side of me moved in and took hold of my arms, wrapped them over their shoulders. I didn’t resist as they walked me from the car and into the hotel. I hung my head though, afraid I would see anyone and hoped no one would recognize me. They got me into the elevator and Tucker stepped in with us, pressed the button for my floor. The elevator was quick but I managed to hold myself together and not get sick. It was a slow walk to our room. Brad let us in with a key. They led me to the bed where I tried to sit but they insisted I lay on my stomach.
Hours later I awoke to the sound of the television and the guys talking in whispered voices. I rolled onto my back, my dick stuck out against in my pants as I realized I had to piss. Luckily, I thought, I was in the shadows. I looked to them in the corner of the room around a small table. They seemed to notice I was awake but I didn’t want them to really notice me, notice my erection, so I slid to the bed and put my feet over the side. I looked to the clock and noticed it was two o’clock in the morning. I shook off the annoyance and headed to the bathroom once my erection subsided.
After I pissed I washed my face with some water and dried off, combed my hair and looked myself over in the mirror. I looked tired but I didn’t feel like sleeping. I hadn’t drank like that since college and I remembered whenever I did that I only slept a few hours to let the alcohol wear off. I went back out to the room and started to walk towards the guys when I noticed something peculiar on the floor. It was clothes.
There were pants, socks, and shoes. I looked up the table where I realized Brad was down to his undershirt while Pete and Tucker were probably missing some pants. Why the pants before the shirts? I shook off the thought and went to them. They looked up to me and I smiled back.
“How are you feeling?” Brad asked.
“Fine,” I said. “Not really, I’m not used to this.”
“Get yourself a drink at the bar,” Pete said.
“That’s a good idea,” I replied before I headed to the mini-bar.
“Want in on the next game?” Tucker asked.
I rolled my eyes at the thought, but to be polite I asked what they were playing.
“Strip poker,” Pete said.
I nodded to myself at the obvious answer as I poured myself a drink. I downed it and picked up a second bottle, headed back to the table with my glass in the other hand. There was an empty chair so I took it. They each looked at their cards before they looked at me or around the room. I laughed nervously before I emptied the second bottle into my glass.
“Read ‘em and weep,” Brad said before he laid down his cards.
The other two moaned in frustration as they threw their cards on the table in defeat, then they both took off their shirts and tossed them out onto the floor far from the game. I laughed a little at them and started to feel confident. If I joined now I would clearly have an advantage.
“Well?” Pete asked.
“I don’t know,” I said.
Brad collected the cards and started to shuffle them. I could see by the way he manipulated them that he was a little drunk. They were all down to their undershirts and underwear. It could be easy to beat them. I shook my head a little to try and get myself to stop from joining but an impulse rose up from my stomach. A quick game, they’d lose and then be gone, I told myself before I started to speak.
“Sure, I’ll play a hand or two, but I’m not taking anything off to make it even. I start with all of my clothes.”
“No problem,” Tucker said.
The other guys agreed and Brad dealt the cards. I had a pair of fives so I decided to stick it out. I lost the first hand to Tucker who had a pair of Kings. I slipped off my shoes but actually relaxed when I got them off. The games slowed down after that as we all talked and joked with each other. Tucker lost his socks, Pete lost his undershirt, and eventually Brad lost his as well, but in turn I lost articles of clothing as well.
In just a few rounds I was down to my underwear and undershirt. Unlike them I took off my socks and shirt first, then my pants. It was kind of embarrassing to lose them but after I sat down Pete poured me another drink.
“Looks like the last bottle,” he said.
“No problem, I got something in my suitcase,” Brad said.
He got up from the table. I could see he had on white briefs. He crossed the room to his suitcase. The movement caught my attention and in my drunken stupor I followed him with more than my eyes. He had a great ass, I thought. I could feel myself getting a little excited about the prospect of seeing him naked. That’s when I realized I had relaxed in my chair and my knees were far apart, my hard dick poked out of my underwear.
When he got back and the guys seemed distracted by pouring drinks I sat up, put my knees together and tucked my dick between my thighs with one hand. I thought no one noticed and decided to join them in another drink. Why not? Now we’re playing for serious stakes, I thought.
Tucker dealt the cards and I felt renewed confidence as I had two Kings and Jack. Pete folded easily. Tucker wasn’t far behind him. It came down to me and Brad. I wanted it all. I wanted everything to be decided.
“I’m all in,” I said.
“I just have my underwear,” he said.
“Sounds like you need to add something then,” Pete said.
I looked at the two of them who laughed and leaned onto the table.
“What could you add?” Tucker said.
“Something important,” Pete said.
“What do you think?” Brad asked.
He leaned forward into the light and I could see his small, muscled chest clearly. He had perfect nipples, just the right amount of development. I wanted to give them a twist. My dick hardened between my thighs. It reminded me of the hazing at a fraternity, just some good, nasty guy fun, but then I worried it would be too much. Would they all think I’m a pervert?
“I say you have to give us a little dance,” Tucker said.
“I nice little strip tease,” Pete said.
I thought my face went red at the suggestion so I leaned back a little, made sure my dick was secure especially because it felt a little slick. I coughed and looked around the room hoping some other idea would occur to me. Something occurred to me.
“How about a wedgie?” I asked.
The guys laughed. Tucker clapped me in the shoulder and said, “now he’s getting into it.”
“I don’t know,” Brad said.
“It’s a wedgie,” Pete added.
“How about it?” Tucker asked.
“I guess.”
Brad looked over at me. How could I have come up with such an idea? Why did I want to humiliate him? A wedgie didn’t sound worse than a strip tease. Lots of guys get wedgies for lots of different reasons.
“There we go,” Tucker said.
“I don’t know though. We’re talking about all his clothes versus a wedgie,” Pete said. I could tell he was trying to instigate something. “How about the loser gets a wedgie?”
I shook my head.
“Come on,” Tucker said. “It’s a good thing to bet.”
I liked the idea of giving him a wedgie better than getting one. I shook my head again and sat back. Both Tucker and Pete looked at me, kept at me. Brad covered his eyes and I started to think I really had him. He didn’t have the cards. I sat back up.
“I’ll still do the dance,” Brad said.
“That’s good,” Pete said.
“Now it’s getting good.”
“Well?” Brad asked.
“Okay,” I replied, “you have to dance for all of us though.”
Brad nodded his head. Pete and Tucker sat back laughing, adjusted themselves, took a drink. I had another myself. Brad did too.
“We should make this really good though. A strip dance doesn’t sound too bad now with a wedgie on the line.”
“Guys,” I said.
“No, come on, you guys are going to be here all weekend. We should make this good,” Tucker said.
“Come on guys,” Brad said.
“Oh, he’s getting nervous,” Pete laughed. He looked to me. “How about you? Are you feeling nervous? Do you think you have the cards?”
I looked at my hand, then up to the guys and smiled.
“He’s got it,” Tucker said.
“How about you?” Pete asked as he looked to Brad.
Brad shifted in his seat, then looked at his cards. He smiled back at them, looked to me.
“What about the loser has to do whatever the winner wants for the weekend?” Tucker asked. “It’ll be fun. Winner doesn’t have to worry about chores.”
I shook my head. Brad laughed a little.
“Ew, this is good,” Pete said. “I wish I still was in the game.”
Was this some kind of setup? Were they trying to see if I was some kind of pervert who got off on humiliating someone? After all they all knew each other.
“Guys, I think this is going too far,” I said.
“A weekend is too much,” Brad said.
“How about a day?” Pete asked. “Maybe one night.”
“One day,” Brad said.
“Come on guys,” I pleaded.
It was too much. I wanted it. I wanted him. The odds were high but I was confident I had the better hand and I was eager to gain something on Brad ever since I shook his hand. I could get my revenge on him. He’d have to strip down in front of me and the other guys, then he’d have to do whatever I wanted. I wouldn’t have to lift a finger the rest of the weekend. I’d could teach him a thing or two. He’d have to respect me. He’d respect me after this weekend.
“Deal,” Brad said before he laid down his cards.
For a moment I worried that I’d lost. He had such confidence, but then I leaned in to set my cards down and quickly recognized I had the better hand. I laid down my cards and the guys laughed as they looked to Brad who covered his face with his hands. He turned away from us and let out a moan of agony.
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