Wendy Swift
Registered On: May 11, 2020
Topics: 12
Replies: 816
Has thanked: 881 times
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My first time caught dressing was by my mom.  I remember it vividly; it was Sat. morning and my mom stepped out to check on my grandma.  I wore my mom’s pink dress with long sleeves, and was prouncing around the house.

I thought it would be fun to “underdress” so I wore my pjs, which also had long sleeves.  My mom comes home, didn’t suspect a thing.  She was going to drive my friend and I to a mall, so my mom and I were talking and I lifted my arm, well my pj sleeve wasn’t long enough and the pink dress sleeve was too long and it showed.

My mom exclaimed “take off my dress now”.  I was so embarrassed I ran into my room and locked the door.  My mom kept shouting thru the door to take off her dress.  Not knowing what else to do and being caught red handed, I took off the dress and handed it back.  I thought my mom would tell my dad but she didn’t, and after I handed the dress back my mom never brought up that subject again.

The second time I was caught was by a stranger, and this time it was downright scary.  Years ago way before covid, my wife would take evening courses at a university close by.  It was great because I didn’t introduce my wife to Wendy yet, and the course lasted about 3 hours.  So it was plenty of time to dress up.  Since she took the course in the fall, it got dark out much sooner.  One night after I ate, seeing how it was dark out, I dressed up (this was before I used make up and bought a cheap costume wig) and decided to walk around the block.

Things were going well, no one was on the sidewalk.  As I was approaching my house, this white 4 door Buick drives past me.  I then see it turn into an alley down the block.  I didn’t think much of it.  I return home, enjoyed being dressed.  When the time came close to pick up my wife, I changed back into drab.  She calls, I go out to the garage, pull out and that white buick was parked right behind our fence.  I couldn’t see who was in it because our back spotlight blinded me.  As I pull away, I see the buick turn on the lights and drive off.  God only knows what this person was doing in the dark alley behind my house.  Maybe I don’t wanna know.


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