My sisters share a bathroom with me and I saw how they would but on their make up so I was sure I could do it myself as well. He went to his bed I co...pletely undressed and sat in the make up chair. I put on her wig, started with the cover girl for base, put on rouge, eyeliner, lipstick, a spritz of perfume and slipped into one of her dresses which was on the tight side. Looking further I put on her stockings and was surprised her shoes fit, I'm a mans shoe size 7 1/2. There were white gloves. I was embarrassed.Riya: Thank you!Me: You are welcome. (still hard-on)She smiled in a kinky way and went out. Before she went she gave me her number and we started chatting! So it was a daily routine. We would meet each other at the park in the morning and frequently chat. Then gradually our chat started turning naughty.Then once she asked me about when I had hard on watching her? I told her I couldn’t resist my boner watching her tits jumping and ass bouncing. Then it was my turn I asked her. Others were staring and pointing out the window so he glanced that way as well.A tall masted sailing ship was entering the bay, it's pale sails reflecting the moon's glow. A murmur started in the crowd, then a few people whistled and began to clap. When the band finished a song about seeing black sails at midnight, the lead singer laughed and called out, "Looks like the hotel pulled out all the stops! There be our pirate kin comin' to visit."Zach laughed at himself for being spooked by the old. .." she replied, "If you want to try it with me, I don't mind..." With that and as if to prove her point, she stood up in front of me and began unbuttoning her jeans. She wiggled them past her shapely hips, down her thighs and past her knees, then stepped out of them and stood with her feet a little wider than shoulder width apart, hands turned toward me and asked, "Will these panties work..? Or would you like me to change into those?" She nodded to the pillow still in my lap.I was speechless..