He finds some really embarrassing underwear

Matt got off the phone and immediately went to his closet. He went through everything to find what he felt would be the dorkiest outfit possible. This included: high waisted khaki shorts that only went to mid thigh, a tight pastel pink button down and suspenders with loafers. Worst of all he had found in his underwear drawer what must have been the most humiliating thing he owned...a pink pair of frilly briefs with little kissy lips on them, given to him as a gift by an ex friend as a gag. He had put them on once and the very idea of putting them on and showing them to people now filled him with dread. And yet he did what Alan told him to do and put them on. He got everything else ready and left for the address. He felt very exposed as he walked along the street in his silly outfit, despite it being mostly normal clothes.

As Matt arrived at the address he saw a somewhat big house at the end of a small lane with a big front porch. It was the house on the address, but wow, Matt was impressed. This place was a mansion compared to his tiny little apartment. Even this made Matt a bit more self conscious about his dynamic with Alan.

The door bell stood waiting to be rung and as he did he saw Alan walk up. “Ah Matt, haha nice outfit” he laughed. “Welcome in, can I get you a drink?

"I hope this is what you wanted. It was the dorkiest I could find..." Matt gladly accepted the invitation for drink. needing to calm his nerves. He looked extremely silly next to the well dressed and confident looking Alan. He was in a smart white shirt and a pair of smart dress pants in black.

“Well I didn’t exactly think you would go this far, I meant maybe a silly T shirt but you do you” he laughed as he reached into a cupboard and pulled out a bottle wine. “Here,” he said pouring his new guest a glass.

Now Matt felt extremely silly. Alan had probably been testing him or something, and Matt had shown his true colors. He drank the wine, maybe a little faster than he should have, but he needed the courage