A nagging doubt crossed Roy's mind for a moment as he marched back to Ashley's room. He hesitated for a second before deciding to reach into Ashley's dresser to find the aforementioned "PJ's" that Stacy wanted him to wear. Of course, when he thought that his chances of staying with Stacy overnight were over after the last incident, Roy opened the drawer to see what he could find.
Bras, panties, stockings, lingerie of all types met his eyes. A quick dread of being a pervert crossed his mind, but then he reminded himself that technically, these were all his at the moment. Roy searched the dresser high and low, but it seemed like most of the things in there were either workout clothes, which wouldn't count, or lingerie that would make any average boy blush. As he pulled out one number that more closely resembled dental floss than underwear, he felt himself do just that.
"Doesn't this girl have any sense of moderation?"
A quick knock came at the door breaking Roy's concentration. "Are you finding everything all right in there?"
"Yeah, just a minute, sorry."
Roy finally settled on the most modest thing he could find that even resembled a nightgown. He couldn't have told anyone what it was accurately. To him, it was a short, light blue, kind of dress that was see-through for the most part with the exception of a few rows of lace that crisscrossed his chest. He still didn't know how it worked with his male parts
Roy noticed that the "nightgown" just barely covered his privates, and even then, he we need to wear some sort of underwear underneath it other than the red ones that Ashley had originally been wearing. Not far from where the nightgown had been stored, he found what had to be a matching set of panties; if you could call them that. Besides two triangular patches that covered his nether-regions on the front and back, there were only two small string on opposite sides of the underwear to hold those patches together. This was definitely a skimpy outfit.
Roy wandered over to Ashley's full length mirror in the corner of her room. He seemed girlier than he expected, but he still looked stupid. He looked like a grown man dressed as a girl. His face really gave it away. Closing his eyes tightly, Roy tried to imagine what the real Ashley would have looked like in his place. An unusual feeling stirred in the pit of his gut, and he felt warm in places that he knew by all rights that he shouldn't have. Roy opened his eyes before his thoughts became any weirder than they already had.
"Alright. Here's the moment of truth..."