Caught For the Last Time Ch. 04

He nodded as he stood there in disbelief.

"If you are good with these and don't touch anything else, we can keep this as our secret. But, if I ever find anything else missing or moved, you will regret it. Are we clear?"

Again, he nodded in agreement.

"Now before we leave my room, do you have any questions?"

He thought for a minute and asked..."Can I have a nightie as well?"

"Seriously, a nightie?" He barely got red and said "Yes. I would really like to wear one at night."

I took a deep breath and went to my nightie drawer and laid out every one of them all on the bed. I had no idea I had so many of them. From baby dolls to full length...quite a collection if you ask me.

Tommy eyed them all over and said "These two fit the best."

He used the past tense which means he probably had tried all of them on. I rolled my eyes.

One was a baby doll and one was a chemise, both very soft. The good news was that I hardly ever wore either of them so I "reluctantly" agreed to part with them.

And what was fun for Tommy is that the baby doll had matching panties he was not aware of. I added them to his little collection. We moved them to that special drawer as well.

Then I said, "Look, mom and dad are away. Let's do this. Bring the bras, panties, nighties...everything into your room for the weekend and we can move it back Sunday afternoon."

"What was not to like with this arrangement and we carried everything over to his room."

"I excused myself to go downstairs to watch some TV and he asked if he minded if he stayed in his room. That made complete sense to me and we said goodnight."

"That first night went fine. I asked him in the morning if he slept in the nightie and in which one. He was still a bit nervous talking to me about it but was pretty open and said the baby doll. After a few chores he retreated to his room and I did not see that much of him the rest of the day. When Sunday afternoon came, everything went back into my room as planned."

"For weeks, this arrangement worked very well. In fact, I was so pleased he was staying out of my stuff that one day while shopping with mom I specifically bought two extra pair of panties that I earmarked in my mind for Tommy and placed them in his drawer. He was so surprised."

Sally continued..."As the months rolled into years, he would sometimes beg me to let him wear certain dresses, which was a hoot. He especially loved all the new ones I bought and I would let him slip one on just to get it out of his system. He was like a sister!"

"To this day, he keeps a separate area in his apartment for just his female clothes and other than a few friends, no one knows. If anyone asks, he just says they belong to his sister who visits him on occasion."

Then my wife cut in and added, "I hope you can now understand why I asked Sally over. She had shared with me her stories years before I fully knew about you and I always kept them private. Even though I knew about your crossdressing before I met Sally, her sharing this with me allowed me to process my feelings."

"It wasn't until earlier this year when I found the panties, again, that I needed to confide in her. I did not know where else to turn. She has been a big help to me and I'm so glad she has been there for me."

Sally continued, "And when I was over in the late summer and saw you in the bra at the kitchen table, it got me thinking about Tommy, a lot."

"I had been going through my fall collection and had a number of long skirts that were no longer fitting my fancy, as well as some tops, light sweaters, and other items and thought that maybe you would be interested in at least taking a look them."

My head was still spinning from all this, but as reality took over I muttered a "Yes, and that sounds like a wonderful offer. I'm not sure what to say." While Sally was not exactly my size, she was a relatively tall woman and wore great clothes.

With that, Sally stepped outside to her car and brought in three large bags of clothing. She placed them on the living room floor and said, "You don't have to go through them now, but please, take your time and keep what you like." Sally turned, gave a big hug to my wife and left.

I was still in shock and was running all kinds of scenarios in my mind. I was happy and embarrassed all at the same time. My wife then apologized to me repeatedly for not saying anything earlier, but felt that this was the best way.

She moved the bags into the other room, walked over and gave me a big hug, and said..."Let's do this in the morning...it'll be Saturday and we have the whole weekend ahead of us. I think we will be in a better state of mind in the morning. I'm curious to what she had brought you as well."

All night long I mulled this in my head until I finally dozed off.