Coach had caught Kenny using his hands too often at practice and several times had made him take off his top and tied it around him trapping his elbows to his sides. Of course, we all teased him about being helpless, grabbed his ass and tweaked a nipple when he least expected it. Was it any surprise that I was now looking at a photo of Kenny in just a jockstrap, helplessly bound in a sling while surrounded by a group of leather men?
Had Coach somehow managed to detect hidden kinks that some of his players unknowingly harbored and nurtured them under the shroud of training or had he just exposed a group of sexually naïve jocks to a series of homoerotic triggers and sat back to see which ones would take root?
Either way, I had to find a way to put an end to Coach’s twisted game. I locked the contents from the binder for my team in the firesafe in my apartment and put the rest in my storage locker in the basement. I had a small lockable file cabinet down there and just as I was about to stuff it with all the lewd files and pictures, inspiration struck. I took out the bottom drawer and laid the files on the floor under the space below the drawer. It was an admirable hiding place. If anyone broke into the filing cabinet, they would just find old tax returns etc. and quickly move on. I had a bunch of heavy stuff piled on top, so lifting the cabinet would require removing all that junk first.
I headed back up to my apartment to contemplate my next move. I had barely gotten in the door when my phone pinged. I panicked for a second thinking I was busted. I checked my phone and saw a text from Jim.
Jim…? Jim Who…? I opened it anyway and froze when I read it…
“Hey Chris. I hope you are well. You may not remember me, we hooked up a few months back.”
OMFG! It was my Papa Bear!!! How could I forget the big burly older stud who popped my virgin cherry and turned me into a total bottom boy?!
“I was hoping that you would be free later for me to stop by your place just to chat. TTYL.
Jim”
Ohmygod Ohmygod Ohmygod Ohmygod Ohmygod Ohmygod Ohmygod Ohmygod
Papa Bear wanted to see me! I almost squealed like a cheerleader over a hunky quarterback.
I tried to get my enthusiasm under control and just play it cool. I took a deep cleansing breath. My hands were shaking with nervous excitement as I tried several times to type out a reply that didn’t sound too lame.
“Oh, Hi Jim. It’s good to hear from you. I totally remember you and would love to see you again, even if it’s just for a chat. Chris.”
After I hit send, I started second guessing my response. Was it too fawning? Of course, it was. The not-so-subtle subtext was, “Please get your hunky self over here and make me your bitch again”.
Ping. C’mon, Chris. Play it cool.
“Cool. I’ll swing by in about an hour. How about I bring a pizza and beer?”
“Sounds great. But no anchovies! 
”
“See you soon!”
Oh my God. This was really happening! OMG! I only had an hour! Fuck!
I cleaned myself out and pre-lubed just in case and took a quick shower. I agonized for a few minutes over shaving. A little stubble could be sexy but decided that I wanted to be smooth for my Papa Bear. While I was shaving, I noticed my pink fingernails. Shit! I had to waste a few more minutes cleaning the cocksucker pink off my fingers. Jim was expecting to be greeted by a man, not a sissy boy.
OMG! Panties! I had NO male underwear left, only nylon panties to wear! OMG. What WAS I going to wear?! I spent the next half hour in a blind panic. I changed my crusty sheets in record time and tore through my closet and drawers trying to find something proper to wear. I finally decided to wear a pair of black nylon short shorts as underwear. At least they weren’t ladies’ panties…
I decided on a light blue polo shirt that was a bit tight in all the right places and looked great on me. I grabbed the same khaki shorts I wore when I first met Jim and hoped he would take the hint that he could have me again. I slipped into my boat shoes to top off the preppy look. I checked my look in the mirror and decided I needed to take it up a notch, so I rolled up the cuffs on the shorts about two inches to mid-thigh. Hmm… I took another inch off. Perfect.
I presented the image of a conservatively dressed young male in a polo shirt and khaki shorts, but with my shaggy hair highlighted and my shorts rolled up to expose most of my smooth thighs it was obvious that I was telegraphing my sexual availability. Hmm… I decided I needed to take it up yet another notch, so I rolled up the cuffs on my polo shirt to just above the bulge of my bicep.
I smiled at my look…early preppy street hustler. Maybe it was too slutty for married, mostly straight Jim. I didn’t want to scare him off by looking too slutty…but what else did I have to wear that was LESS slutty…?
I almost jumped when the doorbell rang. I was out of time. good, bad or indifferent…this was it. I slipped on my mask as I opened the door and there was my Papa Bear, holding beer and pizza, oozing even more sex appeal and pure masculinity than I remembered. Suddenly I felt small, exposed and vulnerable standing before a real man in my little shorts.
“Chris…?” His blue eyes twinkled above his mask with a mix of surprise, amusement and a hint of lust.
I nodded dumbly and held the door open for him to enter. I could feel Jim’s eyes rake over my body as I closed the door.
“You look even prettier than I remembered.”
I blushed furiously at the compliment, “Thanks!” My voice actually cracked and it came out like a squeak. I tried to cover by taking the beer from him and said in my normal voice, “Let me put these bad boys on ice…”
Jim dropped the pizza on the counter while I stowed the beer in the fridge. The cool air hit my bare legs and gave me a chill while Jim checked out my butt. Like the cocktease I am, I took my time putting the beer away and taking two bottles out of the six pack. Another blast of even colder air hit me when I stood up and opened the freezer to retrieve a couple of frosty pint glasses. When I turned around, I noticed Jim looking at my chest. I looked down and saw that my nipples had popped up hard from the cold air and tented my polo shirt like pencil erasers.
I relaxed and took my time pouring the beer into the ice-cold glasses, because I already knew that Papa Bear was going to take me tonight. But I needed to behave myself. Jim had texted that he wanted to talk, so if this was to be our first semi-official date, I wanted it to be more than just a sleazy hookup. Jim noticed that I had left paper plates and napkins on the dinette, so he dropped the pizza on the table and popped the lid, releasing the glorious aroma of oven fresh nirvana.
“Ahh…smells fantastic,” I drooled as I brought in the beers and grabbed a seat.
“Yeah, thank God that Gino’s is still open. Covid caused a lot of places to close.”
We pulled off our masks and dove into the pizza. We covered the usual topics over the next hour or so; Covid, work, sports, beer, until Jim took it to a more personal level, “So you’re going smooth now…?” It was half statement and half question. I understood exactly what he wanted to know.