I looked at myself in the mirror. I was completely naked except for a pair of leopard print Speedo briefs. I wasn't sure if I was going to be able to go through with this. My stomach was in knots, but I was still pretty buzzed from all of the booze and that was going to have to be enough to make this happen.
How did I get myself in this position? Standing in the bathroom of Paul's apartment at 9 o'clock at night, wearing nothing but a small pair of underwear that was hugging my dick and balls like a glove?
12 hours earlier, I was pulling into the parking lot of Paul's apartment complex. Mark and Andrew were already there.
Paul was getting married tomorrow, and Mark, Andrew and myself were his groomsmen. We weren't going to Vegas, but we still had a day planned that involved the local casino, top golf, and plenty of day drinking.
When I knocked on Paul's door, Andrew was the one who opened it. We exchanged pleasantries and went to the kitchen, where Mark and Paul were standing in wait.
"There he is! Now we can get this party started!" Mark whooped.
Four shot glasses stood on the kitchen counter, each filled to the top with a clear liquid. A half empty bottle of tequila was standing next to them.
We each picked up a glass.
"To Paul!" Andrew said.
"To Paul!" Mark and I repeated.
We drained our shots, and soon after we were all in the mid-size SUV that was our Uber to the casino.
The four of us became friends middle school, and we managed to stay friends through high school and now into our mid-20's.
Paul had been dating Lisa for the last 4 years, and he popped the question about a year ago. Mark was getting pretty serious with his current girlfriend Sarah. Andrew and I had dated a few girls, nothing serious, and we were both currently unattached.
When we got to the casino, we had a round of shots before going to the blackjack tables. After a few hands, Paul announced he needed to piss. We told him to meet us at the bar when he was done. Time for more shots.
Paul walked toward the restroom, and the rest of us went to the bar, and that's when Mark and Andrew told me their plan.
Andrew, Paul's best man, leaned close and spoke in a conspiratorial tone.
"Carl, we have a great plan to fuck with Paul tonight after top golf," he said.
"Yeah, dude it's gonna be so good," Mark chimed in.
"What's the plan?" I asked.
Andrew continued, "Okay, so after we get back to Paul's place, we're going to tell Paul that we got a special present for him. We're going to get him undressed to his undies, with a blindfold. He's going to think we got him a stripper. But it's not going to be a woman."
"Oh shit, you guys got him a male stripper?" I said.
Andrew grinned. "Kind of. It's going to be you."
"Wait, what?" I was flabbergasted.
"Come on man, it'll be so funny," Mark said. "Just imagine the look on his face when he realizes it's you in a pair of Speedos."
"Jesus, now I see why you waited until I was a few shots deep before you sprung this on me," I said.
"What do you say? I think it will be hilarious," Andrew said.
"Why don't one of you guys do it?" I asked.
"Well, we thought about that and decided it should be you because you're skinny, like a girl stripper would be. It will add to the illusion."
This was true, I was 5'8" but only 140 lbs. Mark was about my height but with and average build. Andrew was a couple inches taller than Mark and me, and was already working on a beer gut, although he had muscle under the fat. Paul was the jock of our group, easily 6 feet tall and broad shouldered.
"I'll think about it," I said. "I might need a few more shots."
"Well that's no problem at all," Andrew said. "In fact, here comes Paul."
We spent a few hours at the casino. We had lunch there, and had a few more rounds of shots.
When the evening rolled around we took Paul to a steak house for dinner.
After dinner, we went to top golf.
We enjoyed a few rounds of hitting golf balls and more shots of course.
When Paul went to use the restroom, Andrew and Mark took the opportunity to again try and get me on board with their plan.
"Have you decided?" Andrew said. "I'm telling you, it will be hilarious."
My mind was racing. I was beyond tipsy at this point. It would be pretty funny...
"Alright I'm in," I said.
"Hell yeah!" Mark said. "Dude, it's going to be so great."
Paul came back, and I didn't think much about what I had agreed to.
After top golf, we took an Uber back to Paul's place for some video games to finish off the night. We were all sleeping at Paul's apartment. Lisa was out with her bridesmaids and would be staying in a hotel for the evening.
At some point, I was in the kitchen with Mark getting drinks, and Paul was in the living room with Andrew.
Mark handed me a plastic bag and told me to go put on the "outfit" and put my clothes back on over it.
And that's how I ended up in that bathroom, looking at myself in the mirror.
I put my jeans back on over the top of the ridiculous leopard print underwear. I put my shirt on, and went to face my fate.
I gave Mark a subtle nod when I came into the living room, letting him know that the deed was done.
He quickly told Andrew, "Hey, I think it's time for the soon-to-be married guy's surprise."
Andrew said, "You're right, I think they're here."
"Surprise? Who's here?" Paul asked.
"Yeah buddy, we got you something extra special. Since as of tomorrow you probably won't get to have something like this again.
"But in order to get it, you have to play by a couple rules," Andrew said.
"Okay, like what?" Paul said.
"First, strip down to your underwear and sit in the armchair," Mark said.
Paul quickly took off his shirt and shorts. Now clad only in a pair of boxers, he plopped down into the armchair. He had a silly grin on his face and it was clear he was thinking exactly what we wanted him to, that he was getting a stripper.
"And you have to put this on," Andrew said as he handed the blindfold to Paul.
Paul put the blindfold on. Andrew and I went to the front door while Mark stayed by Paul.
To me, Andrew said quietly, "Okay, when he takes off the blindfold, just do like a chippendale dance. Shake your junk and butt at his face."
Andrew opened the door and pretended to be talking to someone, loudly enough so Paul would hear and think someone just arrived.
He closed the door and motioned for me to undress. I stripped down to the Speedos, and we went to the living room.
Paul still had the silly grin on his face, his hands resting on his thighs as he waited for his present.
Mark was standing off to the side, and I saw he had his phone out. He was filming this!
I stood in front of Paul nervously.
"Okay Paul, you ready for your surprise?" Andrew said.
"Hell yeah!" Paul replied.
Andrew started some dance music on the Bluetooth speaker, and said, "Take off the blindfold!"
He took off the blindfold and look on his face was priceless. He was so confused by what he was seeing.
I put my hands behind my head and thrusted my hips forward, causing the package held by my tiny underwear to obscenely flap up and down.
Mark and Andrew were laughing hysterically, and Paul's face went from confused to an embarrassed smile.
"Oh you fuckers!" Paul said with laughter.
I turned around and put my hands on my thighs, bending at the knees and shaking my ass up and down in front of Paul.
"Yeah Carl, work that ass!" Andrew cheered.
I was basically twerking now, my shaking ass hovering just above Paul's lap. I was having difficulty keeping my balance and my butt rubbed across his groin. I felt something starting to grow there. I stood up with my back still to Paul.
"Hey guys, I think he likes it," I said to Andrew and Mark with a tone of exaggerated pride. "I felt a little something happening in his boxers."
"Well what can I say? You got a nice ass," Paul said. He gave a firm slap to my right buttcheek and we all laughed.
"Oh you like my ass do you? Well then how about this?" I said.
I put my ass directly in his lap and I started grinding around. I could feel his dick rubbing against my cheeks. Then I realized my own cock was getting hard.
I continued slowly moving my ass around in his lap, and both of our dicks were getting hard. I actually had to bite my lip so I didn't moan out in pleasure.
I looked over at Mark, who was standing nearby and filming. I looked over at Andrew, who was sitting on the couch. They were both watching Paul and me intensely. The atmosphere in the room was in transition. One of us could make a joke and break the tension and this would all end.
Or one of us could push this further.
I never expected to be turned on by this, but with my head spinning from the booze and my dick doing the thinking for me now, I decided to take action.
I stood up and made it obvious that my hard dick was trying to burst out of the Speedos.
"This is kind of uncomfortable, as you can see it's very restraining. Do you guys mind if I take this off?" I said, with my thumbs hooked into the waistband.
This was the moment of truth. How they reacted would determine how this night was going to go.
After a moment of awkward silence, Andrew said, "Well, I mean, you are supposed to be the stripper."
We all let his words hang in the room, everyone else afraid to say anything.
I slowly lowered my briefs, sliding them off my hips. My rock hard 6 inch dick sprang up as the material cleared it. I bent over to give Paul a good look at my ass as I moved the underwear down off of my ass and then let it fall to the floor.
He grabbed my ass, one cheek in each hand, and gave a firm squeeze.
"Get that ass back down here," he said.
I sat back down on his lap, and continued grinding. My hard cock was bouncing up and down and I moved.
He had positioned his dick in his boxers so it was straight up, and it was firmly between my butt cheeks as I moved up and down. The thin fabric of his boxers was the only thing between us now.
