The truth came out today.  Guy #5 earned his nickname.  We spent another day on Yahoo IM while we worked at our desks miles apart.  I encouraged him to share his secrets with me, tell me what he really wants me to do.

He trusted me.  I have always been the one a man could talk to, tell his secrets to and feel safe.  He took me into uncharted territory.  He told me that he wears women’s underwear!  Every day… to work.  Under his khaki trousers!

So if I had been bold during our meet on Friday, unzipped his fly?  I would’ve found silk and lace and flowers!  No wonder he was so nervous!!

I poked around in his head, asked about how he got started.  He told me about playing in his mother’s underwear drawer as a small child, enjoying the feel of her slips and panties.  Trying them on.  Getting caught.  Being yelled at and called bad names.  She told his father and there was hell to pay.

He was very clear that he is not gay, doesn’t want to be a woman.  Though he is bi-curious.  He mostly just adores the silky fabric against his skin and the pretty colors.  Hey, fabric.  No big deal right?  I could deal with that.

He used a term I had not seen before – sissy.  He showed me web sites, filled with men in women’s clothing, being dominated, serving women and wearing various contraptions to deny them orgasms.
Check out some of these video clips if you dare.
http://mrslovings-sissy-feminization.com/What-s-New/whats-new.html

Hmmm… interesting.  It’s strange how I can think “Yikes!  I could never do that!” and “Damn, that’s hot” at the same time.

Then he said he wanted to be humiliated, dominated, called a sissy and forced to do degrading things.  He wanted me to be mean to him.  He said he was embarrassed.  And he likes that.

That’s where our train went off the tracks.  I told him I could not do that.  That I found it all fascinating but I was not going to be able to help him.  I made up my mind not to see him again.  I was very sad.  He asked if we could be friends, play in other ways.  I was hoping I would not have the time, that I would spend my time finding someone whose needs match mine.  But I agreed to keep talking.

I talked to my online pals.  All of them said to run screaming.  Except one.  A very kind man offered some suggestions, ways that both of us could have fun.  He said to give him little tasks to do for me.  Tell him photos I’d like to see or a story I’d like him to write for me.  Try domming him just a little.  If it didn’t work I could back away but it couldn’t hurt to try.  That appealed to me.  I felt bad that he trusted me and was so used to rejection… I would explore a little.  It seems worth a try – he is the nicest, most considerate friendly man!