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Christmas Shopping Outing 2017 – Part 1

November 17, 2017

Part 1  <– You are here
Part 2
Part 3

Once again, it was time for my annual Christmas shopping outing!  For this year’s Christmas shopping outing, I planned to take only two outfits.  My first outfit would be a patterned dress, black cardigan, nude pantyhose, black flats and high heeled wedge sandals.  I had bought this dress at a consignment store and altered it myself to make it fit me.  I am rather pleased with the fit and look of this dress.  My second outfit would be a purple top, a navy blue cardigan, a royal blue and white striped patterned skirt, and white Keds sneakers.


I told my wife of my plans to go Christmas shopping.  Of course, she knew without me telling her that I would be doing it while dressed pretty.  Interestingly, this time, she never seemed scared.

Read more…


October Haircut and Shopping


It was time for another hair cut.  I decided to get a haircut and go to the “fashion store” (Nordstrom) that I had visited recently.  I wore a patterned dress, with a black cardigan, black flats, and nude pantyhose.

About the dress: I bought this dress at a consignment store several outings ago.  I did not like it at first, but I still tried it on (I think it was recommended).  I thought it looked bad.  Then, I drew up the fabric behind me and realized it had a lot of potential.  I bought it for the experience of altering it.  It sat untouched for months.  Finally, I had some time and I took it in about 2-3 inches (5-8 cm) on each side.  Now, it fits me rather well.  I am pleased! Read more…

Fashion Store


On a recent trip I went on, I traveled on an airplane.  I was seated near the back near two flight attendants.  I bashfully admitted to them that I was a crossdresser.  (I was not dressed pretty at this point in my journey.)  I asked them what brands of pantyhose did they recommend.  One said hers were from Nordstrom.  I believe she said they were the store brand.  They were very pretty.  I decided to drop by a Nordstrom and try some of their pantyhose.

I went to a nearby Nordstrom.  I wore ladies black shorts, my red men’s polo top, nude pantyhose, short white socks and my men’s running shoes.  Beautifully dressed women were everywhere!  Fashionable women shop here.  The clothes on the racks were beautiful.

If you have ever seen the episode of Seinfeld where George Costanza goes to a nightclub full of beautiful women and models, it felt kind of like that.  I had found some secret, mystical world! Read more…

Flying Pretty Outing – Part 4


This is part 4 of a series of posts about a trip I went on.


College Campus
I decided that I should change back into my skirt.  I walked around the college campus.  I visited the department where I would have been a student.  I passed only a few people.  I asked a couple students for directions at one point.  They helped me without hesitation.

I drove the long distance back to the airport.  Near the airport, I stopped at a gas station.  I was unsure how to get to the airport rental lot.  I asked a man at another pump.  He told me what he could. Read more…

Flying Pretty Outing – Part 3


This is part 3 of a series of posts about a trip I went on.


In the morning, I put on a black skirt, a red top, my black flats, and off black Leggs Sheer Energy Active Support pantyhose.  These were not as tight or as pretty as the Hanes Smooth Illusions pantyhose.  (But they were still tight and pretty.)  I felt good about my outfit.

I went downstairs to go to breakfast.  I passed that man in the hall again.  In the lobby, I found the “continental breakfast” was not very inspiring.  I wanted something more significant than cold cereal, fruit, and waffles.  There were two men eating breakfast.  I basically ignored them and filled a cup of orange juice.  I returned to my room.  On my way, I passed that man again as he came down for breakfast.

I collected my belongings and checked out, without incident.  I might have passed that man one more time.  I am not sure. Read more…

Flying Pretty Outing – Part 2


This is part 2 of a series of posts about a trip I went on.

On the Airplane
On the plane, I sat in a window seat beside a man who owns a business.  The man worked almost the whole flight.  Late in the flight, we spoke some.  We had an off-and-on conversation for the rest of the flight.  We talked like normal.

At one point, a flight attendant visited to give out drinks, pretzels and cookies.  She was also wearing a dress and pretty support pantyhose.  (She was doing it better than I was.)  When she was talking to us, I noticed her take a few glances at my legs which happened to be crossed at the time.  If I may, let me take you back with me…  I used to only underdress (wear pantyhose under my pants).  When I would be around a woman who was also wearing pantyhose, I would be joyfully screaming in my heart, “Me too!!!”  That seems to have stopped happening.  Instead, this time, I merely took some pleasure in knowing that I was not the only one dressed like this.  I did not have any “Me too!!!” moments.  I kind of miss them. Read more…

Flying Pretty Outing – Part 1


This is part 1 of a series of posts about a trip I went on.


“Flying pretty” is a term that I believe Kimberly Huddle coined.  It is what a crossdresser calls it when they dress up and fly in a plane to somewhere.  I had the excellent opportunity to fly somewhere this week and I did it while dressed pretty!

My Wife
My wife is not very supportive about my crossdressing.  It makes her uncomfortable.  She does not want our children or friends to know about it.  She does not want me to go out in public and be found out.  However, she also does not like it when I wear pretty stuff around the house after the kids are in bed.  Her ideal solution would be for me to forget about crossdressing altogether.  That has not happened, yet. Read more…