I had a girlfriend named Terri who was surprisingly accepting of my crossdressing. The first night we got it on, I somehow worked up the nerve to tell her about it, and she let me wear her pantyhose the next day. We had a two year live-in relationship. While she accepted anything to do with my wearing lingerie, she didn't want me in drag which was fine by me.
Our little secret was to stay under my clothes or in the bedroom, and we had a lot of fun with it. I wore panties and pantyhose every day with her approval. I would wear bras around the house and in the bedroom. I would sleep in a silky nightie. We would share sexy lingerie. She would often borrow some of my things.
While I tried to lead her into it, Terri could never get into the humiliation component I craved. This was even before the cum eating and anal phases that I eventually evolved into, but I still had this part of me that needed exposure. Once at a party while drunk, I told a woman that I wear panties. When she went off to Terri for confirmation, she was quite nonchalant about it and explained that she washed my panties in the sink with hers.
Terri was willing to take me shopping for lingerie at Frederick’s on a few occasions. She knew that I loved embarrassment, but she didn’t want to be embarrassed herself, so she had limits.
Every once in awhile, she would surprise me. Once we were shopping at a department store and passing through the menswear section. There was a bin display of men's nylon bikini underwear. This style was very similar to a plain bikini panty. Now, this was somewhat advanced for the time as there wasn't much available for men other than the typical boring cotton briefs or boxers. We stopped and noted the style and make of the bikini. She teased me that I'd still rather wear ladies panties. "Of course," I replied with a sly smile.
About that time, another woman happened by and noticed the display with a raised eyebrow. She made a remark about the style and the fact that they were made of nylon, and I said that I thought nylon was much more comfortable than cotton. Then she said to me, "Really? But these aren't much different than women's, are they?" Terri replied, "No they're not, really, and they're much more expensive than women’s." The woman agreed. Terri went on, "That's why I just buy him ladies'…"
There was an uncomfortable pause as we both looked at her with shock.
"You buy him ladies panties?" she asked. I looked at the floor and said under my breath, "I can't believe you're telling her this."
Terri was completely matter-of-fact. "Sure, he likes the feel of nylon. And there are many more styles and colors to choose from. And he actually looks pretty cute in some of them." She giggled. I crossed my arms and scratched my forehead. With wide eyes of disbelief, the woman said, "Well I might get a pair of these for my husband to try, but I don't think I'd ever get him into panties. That’s for sure!"
That sent a wave of humiliation through me. Her man wouldn't wear panties. A real man wouldn't wear panties.
They were finishing the conversation, and my face was red hot by then. I said to Terri in an incredulous tone, "Oh great, just tell her I'm wearing women's underwear!"
She giggled, and said, "Well, you are! Maybe you’d like to tell her about your pantyhose!"
I sighed out loud in desperation. The woman laughed as I pushed Terri down the aisle. I was embarrassed, red faced, and totally turned on. I couldn't believe her guts to expose me to this perfect stranger and tell her that I wear panties. I was completely befuddled the rest of the afternoon.
Situations like this were rare, but I’ll remember the embarrassment forever.