Here is a real story that happened about a year ago to me..
When Courage is not enough...
For the last 14 years, I only wear women´s jeans. I have dozens and they range from all styles but most in common, stretch, fit snug in the hips, not too tight in the thighs, and boot cuts for lower legs.
I have one pair that wear only when my wife is not around and only out on the street when I have a windbreaker or shirt not tucked in. Here in Brazil, where most women have a beautiful hind end (bubble butt in other words) they are the most popular with all. As I kind of fall into that category even as a guy, I have always wanted to wear them out in public, unhidden but I have always lacked the courage to do so.
My business partner called me end of the afternoon, said get ready, we need to fly ourselves to Natal (northern Brazil) tonight which is a trip of about 1,600 miles or 4.5 hours in his turbo-prop executive plane. Client of ours had to go back earlier than plan to France, and wanted to meet with us on our project.
I called and asked my wife to quickly just pack a suite, shirt, tie, good shoes and throw in a pair of jeans and t-shirt for the trip back. I worked on the flight plan, got their project loaded on my laptop and headed to the airport near our home here in Sao Paulo. My friend got there shortly after; and we took off. On the way up, I worked on the presentation in back.
Well after midnight, we checked into the hotel, he took the project to review for the presentation and I went to bed. That morning we had a great 3-hour meeting, presentation was well received, and a few months later closed the contract.
That afternoon, we figured, if we hurried, we could check-out, get to the airport, and fly back to Sao Paulo. I changed quickly, grabbed my hanging bag, computer and we got a taxi back to the airport.
My friend said, on the way back you are going to be PIC (pilot in command) and he was going to take a snooze in back, as he spent a few more hours up at night, reviewing my work. Said OK.
All during this time, period of about 2 hours from hotel to airport and getting plane refueled, flight plan and weather checked, nobody said anything to me, including my business partner.
As we did not have lunch, and a 4-hour flight back, I called the FBO (Service Company) and asked them to stock our frigo-bar with coffee, sandwiches, water and some fruit juices. Shortly afterwards a woman in her mid-40s appeared and I said please put the coffee in out termos bottlw and rest in the refrigerator for me inside by the door, while I finish the preflight.
Some time later, as I was still going through the preflight, and busy, I did not notice anybody around me, when I suddenly jumped with surprise. She had come up behind me, and gave me a hard squeeze and pull on one of my buns. (jeans I wear, do enter the bun separation (jean wedgies) but as this is the way I normally wear my jeans around the house, and it feels great that way. All this time I did not pay attention really what I was wearing.
I just twisted around at the waist, hand felt good there of course, and she was still pulling on my buns and sure I turned red. I said with a smile, hi again! She then let go, chuckled smiled, and said, "I just had to grab you! I knew that you are the type that would not mind." I said wow, you are right, not every day a MILF fondles me, but how do you know that I would not mind you doing that?".
She said it is not every day you see a round butt in a pair of pocket-less jeans! I just stood there, wondering what she said, passed my hand over my back-side, and said, oh my God, I did not even pay attention that I was wearing these jeans, and I almost never put anything in my pockets as think it looks bad. I said, I never wear these out in public. Her reply, "You should only wear these; you look so hot in them".
I said, well follow me in, I will get the credit card in the cockpit to pay you. She followed me up the 5 steps to inside, and at the top she goosed me very hard and well. I said next time I come up we are going out to dinner. You are a MILF and very hot.
Well, those jeans, still do not have courage to wear them out in public.
As to my friend, already in the back sleeping, I told him when we were about 30 minutes out, when he came to the cockpit, what happened. He smiled, and said; yea I noticed them, knew you never like to use pockets in jeans, so I just figured you liked this type.