Panties For Men

After what seemed like an eternity, Mrs. Winters had me back over for the day.  She had a special plan. 

I went over after breakfast and she had me head up to the bedroom right off, in order to get dressed.  I got undressed and took off my underpants right as Mrs. Winters walked-in.  I was given a new pair of pink nylon panties that had white lace trim around the legs and waist.  She helped me fasten a new pink bra around my chest.  I slipped on my dress and put on my shoes.  I was led to dressing table where I got some light makeup. Rouge, eye shadow and lipstick.  We headed downstairs where Mary had me practice my walking and had me sit down a couple of times to make sure I remembered to act like a little lady.

After we talked for a little while, she got up, grabbed her purse and called me to follow her.  We went out to the garage and got into the car.  I thought for sure everyone would see me when we pulled out into the street but no one was around.  We drove out of town to a shopping mall; the one my parents often took us to when we needed new dress clothes.  While we were driving out, Mrs. Winters said we were going clothes shopping.  We got to the mall and she told me not to be nervous, we would be together the whole time.  She took me by the hand and we walked into Sears.  We looked at dresses and skirts and blouses while other ladies and their daughters (?) looked too!  I was so embarrassed because I could never be mistaken for a girl, just a boy with makeup and a dress!  A sales lady came over and asked if we needed any help and Mary told her, that I, her niece needed to try on a couple of dresses.  The sales lady took the clothes over her arm, took me by the hand and we walked to the changing room.  She complimented me on my dress and sandals and said, that I had picked out some real fun outfits.

We got to the dressing rooms and there was another girl and her mom in there too.  The girl went into a room before I did and before I closed the door, I heard her call her mom, saying she couldn’t get the outfit she was trying on, to zip up.  When her mom went in to help, the sales lady leaned down and said, “my name is Lily and if you need any help, just call out and I’ll come in and help”.  I got out of my dress and tried on a skirt and blouse.  The skirt was shorter than the sundress, falling above my knees.  As I was putting on the blouse, Lily walked in and clearly saw my bra.  She said that girls’ blouses button on the other side from boys’ shirts so she thought I might like a little help.  The blouse had a lace stand up collar and a little ribbon tie at the neck and she tied it for me.  I tried to tuck the blouse in but Lily said it’s supposed to be worn loosely and not tucked in.  She took me by the hand and led me out of the room saying “let’s show your Aunt and see what she thinks”  We stepped out and there was the other girl, showing her mom and looking in the 3 mirrors.  The other girl said she liked my blouse; she said it was really pretty on me.  Lily and Mary said the blouse was too sheer and that I needed a camisole because they could see my bra.  They sent me back in the room to try on the rest of the clothes.  Long story short, I came out to model the rest of the clothes and we ended up with the blouse/skirt and 2 dresses.  One had regular shoulders/short sleeves in pastel pink with white lace around the collar and sleeves.  The other was pastel yellow with long sheer sleeves.  Both had zippers up the back that I had to have the sales lady help me with.  She was very nice and kept saying how pretty in was.  The other girl said how pretty I looked in the dresses too, when I came out to model them.  After we gathered up what we were getting, Mrs. Winters took me to the panty section and she picked out some panties, holding them up to look closely and I think to make sure the other girls who was there with there moms, saw what panties I was going to be getting.

We left for lunch and the lady who waited on us said how pretty I was too!  Mary told her how we had just come from shopping and that the sales lady there, had said the same thing.  The waitress asked me what we got and I told her a couple of dresses, and a skirt and blouse.  Mary then added “we needed some new panties too, so we should be all set” The waitress said, it’s always fun when you get to go shopping!