Nothing hotter than a guy in panties!
Guys should only wear baggy jeans if they’re wearing underwear they don’t mind showing off. Jeff was picking up his backpack off the ground and I noticed a flash of pink. Now most guys I know wouldn’t be caught dead wearing pink, especially pink underwear. I got curious and asked if he’d give me a ride home. He said he would and on the way there I asked him why he was wearing pink underwear. He acted like he didn’t know what I was talking about and I went along with that until we got to a red light.
As soon as the car stopped I reached over and undid his jeans. He tried to push my hands away but I was too quick for him. I popped the button open and pulled the zipper down. Busted. “Do you wear lacy pink panties often?” I teased him and he blushed then told me to mind my own business. He really should know me better by now. I told him we were going back to his place; I wanted to see what his underwear drawer looked like. He kept going to my house so out came my phone and I threatened to tell all my girlfriends about his pink panties. For some reason, he suddenly changed his mind and turned the car around.
I headed straight for the dresser and opened it but only found boxers in it.
I asked him where he kept the good stuff and he went to the closet, taking out a garbage bag that looked full of stuff. “So I kind of like wearing women’s clothing,” he muttered as he handed it to me. No kidding, I found a ton of panties, bras, pantyhose, skirts, and dresses. I dumped it on the bed and separated the things, putting lingerie in a pile and stuffing the clothes back in the bag. I asked him to show me his favorite lingerie and he picked out a matching bra and panty set that was all lace and ribbons. Damn it, it was really cute, I wanted to keep it for myself.
I told him we were going to do a little fashion show and he was going to be my crossdressing angel that walked the runway. I put the pile of lingerie in his arms and pushed him into the hallway, telling him that he would put some on, come in and walk around the room then back out to put on another set. So I sat on his bed and waited.
Jeff came in wearing the cute red set and walked past me. I told him to do a twirl and then strike a pose. He gave me a look but did it anyways then quickly walked back out. The next lingerie set was blue and the bra had a little bow on the front. Actually, a lot of the bras had bows on them. I asked why he had a thing for bows and he told me that they made him feel more feminine. I told him they are sexier and he smiled and then went and tried on a different set.
After three or four outfit changes he started to get comfortable, took his time showing me the clothes, and actually seemed to have fun.
He even talked about little details on them, like saying he chose this pair because he liked the hearts on them or this pair because the fabric was softer against his skin. I think it helped a lot when he saw that I was actually supporting him and not making fun.
He seemed to really like showing off his collection to me. Maybe when he’s a bit more confident we can go shopping together.