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

"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.

The Jackoff Show

Before much of what I've written about previously happened, I came out to two girls named Jill and Tracey. We were just friends and would pal around together, often going out to dance. Jill was a lesbian, not necessarily butch but she never really wore feminine clothes. Jill had the hots for Tracey. Tracey was very feminine, girly, and mostly straight although later she "dated" other girls. I came out to Jill first. By coming out, I'm referring to my crossdressing. I guess because she's gay I figured she would understand, and she did. We often went out for drinks, and we would notice the same women together. Over time, there were other aspects of my sissyness that I would reveal to her.

While we had become close friends, Tracey had no interest in me romantically. She was younger than me, and she had boys that she would date. We often talked, and she confided in me about them. I guess it was a form of cuckolding to hear about her dates. I tried to encourage her to give me all the details about what she did with her boyfriend. I secretly wanted her to tell me how he fucked her real good so I could know that I couldn't provide her with the satisfaction her boyfriends gave her.

Somewhere along the line, I told Tracey about my crossdressing, too. Jill was a bit of a gossip, and I figured she had told Tracey anyway. She was fine with it, and we'd often talk about clothes and things, just like two girlfriends. The three of us would often hang out at my place before or after dancing, and I'd often relax into something more comfortable. They both thought it was cute that I'd be wearing girls jeans. They knew I wore feminine underwear most all the time, and they'd see my pantyhose on my ankles or they'd see my bra through my shirt. It was fun to hang out with the girls. Sometimes they'd gently tease me about what I was wearing.

Jill was a bit of an instigator in trying to get things naughty and sexy. My theory is that Jill thought that if everybody got turned on, maybe she could get into Tracey's pants. I also found Tracey attractive, so it was a weird triangle.

Once, Tracey ordered a nightgown as a gift from one of my many lingerie catalogs. When it arrived at my place, Jill teased and suggested that maybe I should model it for them. Tracey agreed, and I went into my bedroom, put the nightie on over my pantyhose, walked shyly out into the living room and did a couple twirls for them. I was going to take it off right away, and they both encouraged me to leave it on for awhile. This was very arousing, wearing a silky full length nightgown and pantyhose in front of both of them. After some time, I was standing in kitchen talking to Tracey when Jill came up behind me and pulled up the nightie above my waist. Tracey stood there grinning while looking at my very hard dick encased in control top pantyhose. After about 20 seconds (seemed like an eternity), I acted embarrassed and pulled the nightie back down.

Over time, little teasing events like this eventually led up to one night in particular when Jill and Tracey asked me to put on a little lingerie show for them. "We want to see more of your collection," they said enthusiastically. It was almost as if they had schemed this. Since they had seen me in a nightie before, I put on one of my own and modeled it for them in the living room. “That’s OK, but let’s see something sexier!” My next trip out of the bedroom was more revealing. I have tons of stuff, so it could have been a very long night. Each time, they encouraged me to wear more and more revealing things for them. I thought I had reached their limit by wearing sheer panties, but they were trying to goad me into the full monty. So I finally came out wearing a bra, garters and stockings and my only pair of crotchless panties.

“That’s much better!,” they gleamed. I was actually embarrassed now, and I felt objectified as a woman would be exposed in front of group of men. They had me walk around for them, and whenever I tried to cover my dick, they told me to take my hand away. I was sticking straight out, and after a short while, I started to lose my hardon. “Don’t let it go soft!” Both of them were enjoying looking at my hard dick. I stroked it to get it hard again. “Yeah! We want a REAL show now!” I couldn’t believe this. I was standing in front of these two women wearing sissy clothes and rubbing myself.

One thing I learned rather quickly is that it is very difficult to maintain an erection in front of an audience. They were clearly enjoying the show, and they made it clear they wanted to see me masturbate in front of them. I felt embarrassed stroking fast as I normally would, and yet it felt so sexy to stand in front of them stroking while they grinned and watched.

I knelt on a stuffed chair and tried to concentrate on the feeling. Eventually, they turned their attention to a music video on the TV and gave me a bit of a break from the performance anxiety I was obviously exhibiting. I was relieved for the break but felt puny because I couldn't entertain them enough to keep their attention from the TV. I felt like the little boy wanking in the corner while the adult girls watched TV, ignoring me.

After what seemed like a very long time with them looking away, I finally got up to the edge, and started making noise like I was going to cum. They returned their attention to me. I’ll never forget the amused look on Tracey’s face as she turned her attention back to me smiling and watched as if I was an entertainer.

I started to get nasty. “I’m gonna fuckin’ cum!” Tracey grinned and coyly replied, “Yeah, fuckin’ cum.” I moaned and started to scream as I shot my wad. I felt as though I needed to show the goods, so I came proudly into my hand while they watched the puddle build. Both of them laughed as I shuddered and gave out that last sigh. They finally gave me a round of applause, and I must have turned bright red. The inevitable post-orgasm shame of wearing the clothes came over me, and I was in a hurry to run back to the bedroom and get more decent.

When I came back, they both told me it was great fun for them. I was still a bit embarrassed. Tracey asked, “You really like to masturbate wearing women’s underwear, don’t you?” I admitted I did. “You obviously enjoy it!” The rest of the night was light. They assured me they enjoyed the show and didn’t make me feel like a complete pervert.

Believe it or not, dear sissies, this really did happen. What may be even harder to believe is that there is a Part Two to this story. Sorry this has taken so long to write, but now that I’ve set the stage, hopefully I can write the second half a little quicker.

Do You Cum Like a Girl?

Whenever I play with my little clit, I moan and whimper like a girl. One time on a phone sex call, and the domme said, "You cum like a girl!" Then she proceeded to mock me in an obviously faked orgasm in the same tone. "Oh my! Oh my! Oh my!!!" It only served to make me even harder and jack off even faster, whimpering all the more and cumming like a girl while she laughed at me calling me a loser.

So, do you cum like a sissy girl?

Putting On A Show

I once dated a nurse named Toni. As I think back on it, I’ve dated a lot of nurses, and I’ve found them to be pretty open minded and some downright kinky. I’ve written about Carla who was a nurse. After our first overnight encounter, she gave me a pair of her panties to wear home, and thus begun a long, kinky relationship.Here are the posts from that relationship:

http://sissyhumiliation.blogspot.com/2008/02/carla.html

http://sissyhumiliation.blogspot.com/2008/02/carla.html

http://sissyhumiliation.blogspot.com/2008/02/carlas-first-lesson.html

http://sissyhumiliation.blogspot.com/2008/02/house-dressing.html

http://sissyhumiliation.blogspot.com/2008/05/carla-takes-me.html


Toni was a real go-getter. After our first date, Toni was stripping of her and my clothes and fucking on the couch in the basement .

I revealed to Toni pretty quickly that I was a crossdresser, and on the second visit to her condo, she gave me a tour of her underwear drawer. She showed me all the matching panties and bras that she had explaining that she always wore matching things under her clothes. Picking out a pretty pair of silky panties, she handed them to me and said I could borrow them. She thought it was sweet that I would be wearing her panties. I was already wearing a pair of my own, and she knew it.

The next day, we were talking on the phone, and I told her I was hard as a rock wearing her pretty panties. Toni was amused by all this. The real fun came when I returned the panties to her several days later. I had laundered them, and put them on the kitchen counter. She asked me how I liked wearing them, and I told her I enjoyed the silky feeling of her panties against my cock. “Show me,” she said. “Rub yourself with them.”

I unzipped my pants and wrapped her silky panties around my cock. I started to stroke myself with them, much to her delight. I was getting visibly turned on as I continued to stroke myself. “Cum in them! I know you’ve been wanting to!” I quickened my stroking as she watched with an amused look on her face and her hands on her hips. She said, “I’ve never had a boyfriend jack off with my panties.” Well of course she hadn’t. She’d never dated a sissy before.

I felt a bit objectified standing before her in the kitchen masturbating as she watched with a sly grin and her hands on her hips. Just as I was getting close to cumming, she cheerfully said, "Squirt, squirt, squirt!" That did it. I let myself go and came loudly while Toni stood there watching.

“Did that feel good, honey?” she purred. I nodded. “Let me see…” She wanted me to open the panties and show her my load. “Ooooh… good boy…” The tone of her voice made me feel small, like a little boy. Good little sissy made a puddle.

But this hadn’t been the first time I had put on a masturbation show. I’ll tell you about a show I put on for a small group of women.