Stripper for Gay Halloween Party

When you're single being a penurious 21 year old isn't all that bad. But when you're in a relationship you want to make your lovely partner happy. You want to shower her with saccharine gifts and put a big smile on her face. Its difficult to do that when you're broke. Here is the true story of when I was young and desperate for cash.

The only thing I had going for me back then was my physique and athletics but those don't really make you money. Well at least not in any kind of legitimate way. I had an anonymous account on the app Grindr with just pictures of my muscular body. My morbid sexual curiosity oftentimes gets the best of me I must admit.

It was 10 days before Halloween when I received and intriguing message from a gay couple on the app.

"Every year we throw an elaborate Halloween party with drinks, costumes, music, games, dancing, the works. Naturally we hire a servers to serve drinks and entertain guests."

"Entertain guests... what does that entail?" I replied, my curiosity piqued.

"You would be flirting, dancing, playing games like Twister with the other servers and overall just elevating the mood of the party"

"Do I need to wear a costume?"

"If you are selected we will choose your costume but all the servers are required to wear this."

He sent a picture of a tiny thong jockstrap that covered only the dick and balls. My bare ass would be on display.

"I'm Mike by the way and this is my partner Lucas." he said sending more pics of them as a couple.

I replied with some photos of my own

"Wow you'll be the biggest strongest guy we've ever hired for this job. You'll get great tips with a bubble butt like that."

"Thanks I guess." I responded.

Four or five hundred dollars for one night of embarrassment seemed like a worthy trade off.

"The most important thing is to be chatty and outgoing. Last year the servers were too shy... no good. If you're comfortable with all this I'd like to offer you the job. Remember this isn't prostitution or anything like that. Think of it like being a stripper. The guests are all respectful and the most you can expect is a pat on the bottom or two. And you'll be taking home 100 dollars an hour... plus tips."

Reluctantly I agreed to take the job.

I didn't hear from Mike or Lucas until the night before when Mike texted me the address and what time to come over. We agreed to meet an hour early to go over all the details.

Tomorrow came and I was a nervous wreck. The things we do for love. I knocked on the door and Mike was standing there with Lucas right behind him.

"So you must be Max. I recognize you from the app. Please come in."

They were both on the tall side and in their early 30s. Their entire house was covered in Halloween decorations. Everywhere you looked there was something spooky. The room had a bar on one side and a bunch of tables and couches. I could tell that they took the whole Halloween thing very seriously.

They were standing in front of me and the other server who was a petite guy around the same age as me. Mike began his explanation:

"Feel free to have a drink or two during the party and enjoy yourselves."

"Guests may ask you for a lap dance since that is what our servers have done in the past."

"Lets strip you both down and see how you look in your jock straps."

This was the point of no return. I slowly began getting undressed.

I was now standing there naked as a Jaybird.

"Your cock will fill out that jockstrap nicely," Lucas observed handing us our respective garments.

I put it on. It felt like it was squeezing against my thighs and making my butt pop out more. The thong part disappeared between my butt cheeks.

"Mmm a perfect fit." Mike noted tapping my behind gently with his hand.

I couldn't believe I was really about to do this. A straight man with a beautiful girlfriend about to prance around a party, cheeks exposed. Getting ogled and getting my tush slapped or pinched. I never thought I would find myself in a situation like this. The humiliating nature of this job was arousing but that didn't stop my anxiousness in the moment. The costume I was given wasn't really a costume just a small mask that went over my eyes. So I was naked wearing only a jockstrap.

Soon the doorbell rang and guests began arriving. I counted about 20 people and I knew I was going to be introduced to all of them in some form or another. Mike and Lucas were standing close to the door greeting and mingling with the guests.

"Hey baby bring us 4 White-claws" One of the guests dressed as Robin requested.

Every time I reached into the mini fridge I had to squat down with my ass sticking out. I could feel the entire room's eyes on me. The other server was overly shy he hardly talked to the guests at all so I had to be the star of the show.

"Here you are gentleman." I handed out all the beers and to reach the guy on the far end of the couch I had to bend over almost all the way over.

"Thanks honeybuns." One of them said.

My face was bright red but with the low lighting no one could tell.

Once everyone began to get inebriated the fun started... fun for them at least.

Nearly every guest had given me a tip I didn't really have time to count it all or examine the bills to closely. Getting my bottom slapped by a man and called "Good boy" was a first for me.

A guy in a wolf costume said "Come sit on my lap." when I walked past him so I climbed up onto his lap. I was sitting facing sideways I could feel his dick getting hard and pressing up against my glutes.

"Are you the big bad wolf?" I asked trying to break the tension

"Yes sir, damn you're really strong." He said looking me up and down.

"Thank you." I replied laughing

He was grinning from ear to ear and looking me right in the eyes.

"I wanna see you shake that tight little booty of yours."

"I'm like Phil Collins... I can't dance" I hoped my attempt at humor would get him off the subject.

Suddenly Mike saved me.

"Hey Max come over here!" He shouted from across the room.

"Have you ever played twister?" Mike asked.

"Yeah when I was a kid I played it a couple times. I'm not very flexible though."

"That's ok you'll do just fine. It'll just be the two of you." He said gesturing towards the other server.

When he was setting up the Twister mat I considered just running out of there since at least I'd have the tips. But I thought if I did that it would have all been for nothing. So I stayed.

If you've ever played Twister you know how the game goes. Its super easy until its not. So after the first few rounds I was in the most revealing position possible. I was on all fours with my head down and butt elevated high in the air with the other server underneath me. Many of the guests were sitting on the couch a few feet away from my ass watching. I guess they enjoyed the view because they were cheering and making comments.

"Anyone ever tell you how pretty you look from behind?"

My entire body was shaven and smooth. Perhaps that is what he was referring to.

I ended up losing the game. Being as big and jacked as I am my slender opponent had a notable advantage.

"Alright lets see the punishment for the loser" Mike said as he rolled a giant foam die. It landed on six.

Lucas emerged from the other room holding a big pink paddle.

"Put both hands on the couch and bend over young man" He said barely containing his laughter.

I did as I was told. All the guests were chomping at the bit to get in on the action.

Mike gave me the first one.

WHACK

As loud as it was it actually didn't hurt at all.

Another guest gave it a go

WHACK

Then another

WHACK

Everyone was whooping and applauding.

Lucas who looked like he was the strongest of the group took the paddle.

"Ok these last three are going to be hard. Brace yourself."

I gripped the couch with all my strength.

WHACK WHACK WHACK

"Good job!" He said rubbing my cheeks with both hands.

"Awww look at that pink cake." Mike said.

"Looks better with some color huh?" Another guest added

I didn't know what was redder my face or my booty cheeks.

It was the end of the night and the guests were starting to go home. I breathed a sigh of relief. I was mortified at the idea of ever running into any of these people ever again. Sure I had my little mask on but my build was still recognizable.

Nearly every guy there had touched my butt and seen every crevice of my body. But like Mike and Lucas promised nothing sexual occurred so I took solace in that.

Before I left Mike counted out 400 dollars for the four hours I was there and then added an extra 100. With the tips included I took home 600 dollars.

"You did a good job tonight. You are a natural at this."

Him and Lucas were looking at me like they wanted to pop my cherry. Which I was of course not interested in.

"Thank you." was all I could think to say in the moment as I was leaving.

The next day I got a text.

"We will keep you in mind for any job opportunities like this that arise in the future."

I blocked the number immediately.

The next weekend I took my girlfriend on an expensive date at a upscale restaurant in the city. I wonder if she would ever guess in ten million years how her man got all that money...

Some secrets are never meant to be revealed.