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.
