Monday, October 18, 2010

"Have you ever worn women's silky underwear?"

"I want to ask you: have you ever worn women's silky underwear?"


"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.



Anonymous said...

Hope you someday post again...Had something of a similar nature happen. "are those GIRL panties...?"

Anonymous said...

Just in case you missed it.

Anonymous said...

Your keyboard ain't been rockin' so I've come a knockin'! Drop your cock and take us on a high heeled walk.

I hope you saw that link I left you before it disappeared. Leotard wearing strap-on sportin' serious lesbian action!

Chrisissy said...

Maybe telling her all or having her catch you in the act would have been more fun than just letting the relationship end uneventful!

Little Pantyboy said...

beckyNpanties, I'd love to hear your story!

graham said...

yes i wear panties all the time at home i wear panties bra dress blouse my girlfriend made me become her sissy wife and slave

graham said...

yes i have worn women silky panties and bra as im write this imwearing a pink bra and matching panties and i love them wend i go and clean house for a lady friend of mine she ask me if i would wear a maid out fit i said yes you can put me in it good i what you to wear it for me she said i think you will look cute she hand me the out fit and i put on the dress blouse apron and nylon she hand me some flase breast to put in my bra she said dos that feel better i said yes i look like a girl now then she put a wig and make up on she told me that the way i should dress for her from now on wend i clean house for her i said yes i will miss. becuse im your sissy maid and want to please you

silkydave said...

Nice story, well written. Let's have some more LPB. Very good stuff. I have had two understanding wives but probably wouldn't have revealed my penchant for (particularly)nylon slips to a girlfriend who may have then told the whole world. I mean, it is a bit embarrassing though very thrilling, our little fetish.

Anonymous said...

I wear silky bloomers with my stockings and suspenders when I visit my next door neighbour

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Anonymous said...

Ladies, great way to keep your man ( girlie man) in line? Is nylon panties, with pantyhose paint his toesy's too! I did this to him already. He doesn't like the surprise panty check I do to him? When he goes out with the boys? And he's dressed underneath his clothes as a sexy girl! " hee, " hee". Jennifer.

mk said...
This comment has been removed by a blog administrator.
Anonymous said...

I wear NOTHING but knickers