"I want to ask you: have you ever worn women's silky underwear?"
Silence.
"What?" I responded, curiously. This phone conversation had just taken a very rapid turn.
She repeated slowly with more insistence, "Have you ever worn women's silky underwear?"
Cindy was the original Miss Priss. Well educated, prim, proper, and fussy. We'd been dating for about six months, and I don't know what really attracted me to her.
As with many women I dated, I dropped hints here and there... like how I "had to" wear pantyhose under my pants to do some work outdoors on a particularly cold and windy day. Or how I dressed up as a girl for Halloween. If it got the right giggly response, I would tell them how my girlfriend at the time had dared me wear EVERYTHING including bra, panties, pantyhose, girdle, heels, etc. Well, OK, that's not entirely true because Terri, the girl I was living with, knew full well of my crossdressing, and she just helped me dress up one Halloween. She provided some of the outer wear, and I already had more lingerie than she did.
Most women would find it amusing and think of me as a more evolved man because "now you know what we have to go through," and I would engage them in an extended conversation about wearing such underthings and navigating in high heels and a girdle (I wouldn't mention that I particularly like girdles because they hold a butt plug firmly in place). Maybe I'd throw in a little tidbit about how I wore a silky nightgown to bed that night after the party. (OK, I wore a nightie to bed every night with Terri.) That might get a real rise because I would be hitting the edge of concern. One girlfriend giggled and said, "I'm beginning to wonder about you!" and then I'd back down and say, well, it was an interesting experiment.Cindy wasn't amused by this, although she wasn't immediately repulsed. And while I didn't go so far as revealing the "nightie" night, I continued to bring up the subject gingerly until it must have reached critical mass for her. Perhaps she had a consultation with a female friend or her mother, expressing concern over these things that I mentioned. "Just ask him outright! Ask him if he ever wore women's silky underwear. After all, that's what 'those men' like to do!"
I was a bit bemused by the nature of her question. I toyed with retorting, "You're worried about 'silky underwear?' Women's cotton panty briefs don't count? What about pantyhose? I wear them almost daily. I have some bras that aren't silky per se. Are dresses, blouses and skirts OK?"
But I could tell that Miss Priss was launching an investigation here. She had to get to the bottom of this crossdressing issue, and she was intent on how I answered. I figured I'd stall for time and fall back on known issues.
"I told you I dressed up for Halloween..." I don't think I had told her about the extent of my underpinnings, but now I was essentially admitting to the dread "women's silky underwear."
"Yes you told me about that..." Her tone said she was demanding more. "What other times?"
"And I wore them the night before..."
"You did?" She was beginning to become alarmed.
"
Yes, of course, we had to see if everything fit, so I had to try on all the underwear, too." Again another admission with "all the underwear." Let her imagine what that meant. As in, full blown lingerie. As in "WOMEN'S SILKY UNDERWEAR!!" She didn't quiz me about the details. I wished she had. I would have given her details about the lace underwire bra and the satin panties with the lace at the leg openings.She remained on task, "Okay, other than that?"
"Well, I told you about wearing pantyhose. I guess you could say they were silky."
She quickly returned, "Other than those times, have you worn women's silky underwear?"
Time to bail. She isn't going to ever accept it in any way, shape or form.
"No." I lied.
"Why this concern about silky underwear?" I asked.
She explained, "Well there are men who do that."
Yes, I know. I remember my girlfriend in high school explaining that fact of life to me. She gave me one of her slips to help me with a made up hazing thing where I supposedly had to dress as a girl and wear girls underwear.
I never brought up the topic with Cindy again, and I knew we were done. I wasn't going to get a sympathetic giggle out of her. She wasn't going to accept me in panties.
Ever.
