Booth Babe Pt. 01 - Sex Stories

Booth Babe Pt. 01

... that I was a crossdresser.

"Can you tell me about you dressing up? I promise I won't judge, honestly, I have been really curious to hear about it since I found your stuff on Tuesday. I had to fight not calling you and asking about it the last two day." She said as she gently rubbed my arm.

"Can we go sit in the family room? Being around all her stuff... well it is kind of sad and depressing. I really do appreciate you doing this, not sure I would have ever been able to do it myself. Thank you." I told her.

"Of course, and you are welcome. It wasn't easy for me either but it... well it helped me to accept that she really is gone." Casie said as her throat caught, and she started to tear up.

I took her hand, and we walked out to the family room. I asked if she wanted a water bottle, and she told me yes so, I grabbed two out of the fridge and brought them out to the family room. She sat on the love seat, and I took a seat on the couch. Neither of us spoke and the tension built. It finally broke when she smiled at me.

"I started dressing up when I was a teenager, I don't really know why I felt the need to do it but sometimes it was an almost overwhelming desire or need." I told her, shocked I could say that out loud to her.

"Did you have your own things back then also?" She asked me.

"No... I borrowed stuff from my mom and sister... your grandma and aunt. I am not sure if grandma ever knew but your aunt figured it out and black mailed me. She made me dress up ...

... in front of her and her best friend and put makeup on me." I explained.

"Oh... that wasn't very nice of Aunt Lisa." Casie frowned.

"No... I hated that she knew and forced me to do it, but they didn't make me look clownish, they made me look..." I couldn't finish my statement, so Casie did.

"Pretty... and you liked looking pretty?"

"Yes... very much." I said quietly. "Lisa was furious. She wanted me to be humiliated but her friend thought it was great that I looked so good. I was scared that was going to make Lisa go through with her threat to tell everyone, but she didn't." "Did they ever do it again?" Casie asked.

"No. I wanted them to, but Lisa just told me that if she ever caught or suspected I had worn her stuff again after that she would tell everyone, so I stopped, well I stopped wearing her stuff." I said.

"How did mom find out about it? Did she catch you wearing her stuff? Wait... did you ever wear any of my things?" Casie asked alarm.

"I never wore anything of yours, I promise. I had one moment of weakness when I thought about putting on your cheerleading uniform but fortunately, I was able to stop myself from doing that." I told her.

"Oh... well... honestly, I could see why that would be tempting. I mean what is more girly than a cheerleading outfit. I still have them and... well if you want to you are welcome to put one on." She said smiling at me.

"Really? Seriously?" I asked surprised.

"Yes... so what about mom's stuff have you worn ...