Caught! - Sex Stories

Caught!

... If you’re still sure you want to do this, come back and we’ll go. Deal?” I said, wondering whether I should get myself involved in what could be a very volatile situation.

“Deal,” Nathan shouted, struggling to remove the corset as quickly as possible.

I helped him get the corset off and he ran toward the door, pulling his shirt on as he went.

“I’ll be back,” he shouted opening the front door.

“Wait, don’t forget the last box,” I called, grabbing the box and rushing after him.

Nathan ran back, grabbed the box, and ran out again. I stood in the doorway, watching him drive away and wondered if I had just made a bad situation even worse. If Christa found out I was teaching her little brother to become a crossdressing sissy like me, I shuddered to think what that might lead to. Still, Nathan was clearly having a hard time and needed someone who understood what he was going through to be there for him. I couldn’t just turn him away, even if it did end up causing more problems for me.

I debated with myself over how best to help Nathan while waiting to see if he would indeed return. I understood the feelings he was having and the trouble he was having accepting who he was but, wasn’t sure I was actually qualified to give advice on how he should handle it, considering what had just happened in my life.

I thought of my own early experiences, sneaking panties and hose from my sister’s drawers, feeling sexy and posing in the mirror, how good it felt to stop ...

... fighting the deep seeded urges in me and take a cock in my mouth for the first time, and the fear of being found out afterward. My cock twitched at the memory of sucking my friend’s hard cock in our tent and him exploding in my mouth.

I also remembered how he had refused to talk to me for months afterward and threatened to tell everyone I was gay if I came near him again. I remembered it all, the pleasure and the pain, it would have been nice to have someone to help guide me through those early years. Hell, it would be nice to have somebody who understood to talk to about what just happened with Christa.

Unsurprisingly, Nathan did return, just as excited to start his journey as he had been when he left. There was no doubt in my mind, this is definitely what he wanted. We jumped in my truck and I took him to a little boutique downtown with a discrete backroom dedicated especially to crossdressers. They didn’t have a large selection but, everything they had was high quality and very sexy and the staff were very friendly and helpful.

Elaine, the gray-haired proprietor, was helping a customer when we walked in and smiled pleasantly over the woman’s shoulder as we slipped quietly through the door to the backroom.

“Hi Dani, looks like you’ve brought a new friend,” Linda, one of Elaine’s assistants greeted us as we entered.

“Hi Linda, hi Jenna,” I said, greeting both Linda and the customer she was helping who I had met on previous visits to the store. “This is…” I paused ...