Nellie

Nellie

by Princess Pervette

"You know, you'd look good in drag," Harriet told me one evening.

We had been living together for about a month, and she had never mentioned such a thing before.

"Have you ever tried wearing drag?" she pursued. "You've got the face for it, and that's half the battle."

The whole idea, as I thought of it, struck me as twisted and sick. But I was at the height of my rebellious period in those days, when anything sick and twisted had a certain appeal to me. So naturally I thought it might be worth a try.

"No, I never have. But it sounds as if it might be fun to try.... Sure, why not?"

I thought about it the next day at work, and the more I thought about it, the more it appealed to me. The idea of abandoning, or at least temporarily setting aside, my masculinity seemed kinky and captivated my imagination.

So that evening we tried it, or rather, I tried it. First, she gave me a pair of pink panties, and I put them on. Then she gave me a garter belt and showed me how to put that on. Then I rolled on a pair of nylons. The bra came next; she showed me how to fasten it and then rotate it so the cups were in front. We used handkerchiefs stuffed into the to give me a nice pair of boobs. Harriet's clothes weren't a perfect fit, but I was able to get into them pretty well. She found a dress that was loose enough about the waist to fit me, and she put makeup on my face.

After all that, you expect me to say I was thrilled to be dressed in women's clothes, right?

Wrong. It was a failure.

The clothes were uncomfortable. They were a little uncomfortable physically, because the fit wasn't as good as it might be, but they were terribly uncomfortable mentally, because I didn't feel right in them. I felt silly wearing them. And when Harriet had me look at myself in the mirror, I didn't see a pretty girl; I saw a damned fool. Here was this man, obviously a man, with a bunch of women's clothes on him and his face full of paint, looking silly and embarrassed.

"Well, this was an interesting possibility," I told her, "but it isn't going to work."

"How do you know? You've only tried it once."

"It just doesn't feel right for me. I feel ridiculous and I look ridiculous."

"Well, you would look more convincing if I had a wig...."

"No. I can tell; it just isn't going to work."

I got back into my regular clothes with a feeling of relief and, I must confess, disappointment. I had been sort of looking forward to becoming a crossdresser. Women's clothes came in such a wonderful variety and looked so great.... But, dull and uninteresting as my own clothes were, I was still relieved to get back in them.

And that would have been the end of it, if Harriet had been less persistent and resourceful.

The next evening, she said, "I wonder what it would be like if we went about this more gradually."

"Went about what?" The drag experiment was by that time a closed chapter in my own mind.

"Dressing you up. You really have potential. You could pass if you went out on the street. I hate to see that go to waste."

"Harriet, I'm willing to try anything once. Well, almost anything. But not twice. If something doesn't work, it doesn't work, that's all."

"I think we tried to do too much too soon. Too suddenly." She paused. "I wonder if you would just do a little favor for me."

"What?"

"Wear these under your clothes for two weeks." She held up a pair of white panties. "I got these for you today. They'll fit you better than the ones you tried last night. And nobody's going to know you have them on. Do it, just to oblige me. And after two weeks, you can stop if you want to."

I sighed. I already knew it would be hopeless, but I knew better than to argue. "Okay," I said.

So, the next morning when I got dressed, I put the white panties on instead of my regular briefs. They did fit me, and I noticed with surprise that they accommodated my male parts quite well. When I mentioned this to Harriet, she said, "Of course. I knew what kind to get. Do you think you're the only guy I've ever dressed? I put every boyfriend in dresses sooner or later." That was news to me. The panties felt funny going on, but I noticed right away how soft and smooth they felt. I had been too nervous to notice that the first time. They seemed...well, kind of neat. That should have told me something.

Once I had them on, I found I didn't notice them much. They didn't feel that different from my ordinary underwear. But I was conscious of them all day, and although, as Harriet had said, nobody could tell I was wearing them, I felt ill at ease, as if my trousers were somehow transparent--as if, at any moment, someone might come up and say, "Hey...are those panties you're wearing under your suit?"

She had gotten me several pairs, and the next day's pair were pale blue. I was surprised at how good it felt to put them on. My nervousness and discomfort were beginning to fade, which was clearly just what Harriet had in mind.

The third day's pair were pink with little red flowers on them. Lace around the legs. Harriet was carefully sequencing the panties, you see: first white, then blue, then pink with flowers: day by day, steadily more feminine. And her scheme was working: I realized that I was beginning to enjoy wearing them.

In fact, I came to enjoy them so much that by the end of two weeks I was ready to throw out all my jockey shorts. But I didn't. I was in two contradictory states of mind: part of me insisted that this was just a temporary experiment, just a silly little thing I was doing to please Harriet; another part of me didn't want the experiment to end.

It didn't end, either. At the end of the two weeks, Harriet unwrapped a garter belt and nylons.

"Oh no!" I objected. "I've done you a favor, and I'll admit that the panties feel pretty good. Better than I had expected. And I'll admit that nobody can tell I'm wearing them. Even when I pee, all I need to do is pull the waistband down. But I'm not wearing women's stockings to work! Those will show!"

"Of course they will, Bill, and I wouldn't dream of making you wear these to work. But just wear them around here evenings. To please me?"

So I took off my pants and put on the garter belt and the nylons. I noticed for the first time how they enhanced the appearance of my legs, shaping and coloring them. I had been too nervous that first night to notice this. I've never thought of myself as an Adonis, but I always thought I had pretty good legs--for a man; the nylons made them look great. But just the same, I was glad to put my trousers on over them so they wouldn't show.

So for the next two weeks, I wore nylon stockings around the apartment evenings. And it felt good to have them on my legs, I must admit. I should have seen the way things were going one evening when I stopped and admired how I looked for a few minutes before putting my pants back on. My legs were soooo sleek and smooth and shapely in them, and I appreciated how the colored fabric--they were taupe, I remember--darkened my legs and shaded them.

The following Monday morning, Harriet had a pair of opaque black nylons for me.

"If you wear these, the part that shows under your trousers and over your shoes will look just like regular men's dress socks. Nobody will be the wiser."

I put them on without a word. And once or twice at work, when I knew I was alone, I pulled up my trouser legs to see how the nylons looked on me. They looked really pretty. Then I realized that I was at work, in my office, with panties and a women's garter belt and stockings on under my suit. I blushed furiously, even though nobody was around, and let the trouser legs fall back into place.

I must have been another two or three weeks wearing these things under my regular clothes. Evenings Harriet would ask me to change into lighter-colored nylons, but during the day it was opaque black or opaque navy.

Then one evening she said, "That's a pretty boring-looking shirt you're wearing. Here: try this." It was a white silk blouse. I hesitated. Then I figured that I was already wearing panties and nylons under my clothes, so this didn't amount to that much of an addition to all the rest. And it didn't look that different from a shirt, except for the ruffles. I took off my shirt and put on the blouse. I had some trouble with the buttons, because the blouse buttoned the wrong way. I think that brought home to me more than anything else just what I was had on. And although I still had a T- shirt on underneath it, I noticed the cool feel of the silk on my arms when I put it on.

So now she had me wearing panties, nylons, and a woman's blouse. And I must admit that the uncomfortable feeling I had had the very first time she dressed me didn't return.

In fact, I realized that I was beginning to like wearing these things. A lot. It was about this time that I threw out all my jockey shorts. Something inside me said, "This means you're going to wear panties all the rest of your life." That bothered me briefly until I told myself that I could always go out and buy new jockeys if I wanted to.

Nothing changed after that for a month or two. Then the weather began to get warm, and one Saturday morning Harriet said, "You know, it's beginning to be shorts weather."

I could see what was coming. I said, as casually as I could, "Yes. I'll have to shop for some this afternoon."

She had anticipated me. "Here, try these on." She had gotten me a pair. Women's shorts, in a light blue color.

"Put your black nylons on first. They'll contrast nicely with the blue of the shorts. And they'll show off your legs."

She had almost done it. Except for my shoes, I was dressed from head to toe in women's clothes. (I had stopped wearing T-shirts under my blouses when the weather turned warm.) And I was liking it. Every weekend after that, I wore an ensemble along those lines. But Harriet wasn't finished yet, by any means. The next Saturday I was going to wear a pair of dark blue shorts with a pair of light tan nylons. But Harriet stopped me.

"Your legs look ugly in those."

"You said I had nice legs...."

"You have. You have terrific legs. They make me jealous. They would make any woman jealous. But all that hair...! Why don't you try shaving them just once, to see how they look that way? And don't tell me they'll notice in the office. They won't."

So I went back into the john and shaved my legs. It was a big job, because the razor kept getting clogged with hair. I'd make one swipe with the razor and have to rinse the hair out of it. But finally I was done, and I saw how strangely pale my legs looked with no hair on them. But when I rolled on the nylons....wow! What a sensuous feeling, with nothing between the hose and my skin! And the way they looked...I had never noticed before how the hair showed through the hose, but I noticed its absence now, and the improvement was striking. That evening, as we sat and read, I kept looking down at my legs and admiring how they looked. And at times I would run my hands over my ankle and feel how nice the nylon felt.

"You know, if you take your shoes off, you can put both your legs on the seat beside you," Harriet pointed out. "It might be more comfortable." I was on the sofa. So I tried that and noticed how it made my legs more noticeable. Then it struck me: this was the way women sat on sofas.

Harriet's plan was working. I had gotten to the point now where I wondered what she would want me to do next. In fact, I was impatient to know. And eager to try. I had come a long way since that time last Fall when she had dressed me and made me feel so foolish.

What she had next, a couple of weeks later, was a "skort." This was a pair of shorts made with a piece of material that went right across the front, so it looked like shorts from the back but a skirt in the front. It was her way of gradually getting me into skirts. I almost grabbed it out of her hand in my eagerness to try it on.

Along with the skort came my first pair of women's shoes. They were a pair of white pumps. Low-heeled, but unmistakably pumps. This was now a degree of feminization beyond even what we had tried last Fall, because back then she had had no shoes that I could wear.

Wearing my skort, a dark gray blouse, off-black nylons, and my new pumps, I came into the living room and said,

"How do you like your girl, Harriet?" Then I thought: Did I really call myself that? Well, yes, that was how I felt.

"You're gorgeous, Girl! Really terrific!"

And from that time on, whenever we were alone, Harriet always addressed me as "Girl." I realized that loved it. I had come to love being a girl. Well...looking like one, anyway.

Things moved swiftly after that. Harriet got me a wig, in a brunette color that matched my hair and my coloring generally. That evening she had me shave a second time and then applied makeup, very slowly and very carefully. Then she put on the wig and combed it for me.

I suddenly caught sight of myself in the mirror. This was the first time since last Fall that I had looked at my reflection carefully. Back then, I had seen a damned fool. This evening, I saw a girl. A pretty girl.

"You look fantastic, Girl! Now we need a name for you. Bill isn't going to do. How about Nell? Would you mind being Nell?"

"Er...well, the first thing that makes me think of is Nellie. And when I was in college a guy who was nellie was a fag."

"In those clothes you aren't a guy who is nellie. You're a girl who is Nellie. And now that the topic has come up--have you ever made it with a guy?"

"Uh...well...if you must know, I did have a sort of a, a bit of a...little fling with a roommate one term. But then I moved out," I added, hastily. It had been somewhat more than a fling, but I wasn't about to admit that.

"A sort of a bit of a little fling. I think we'll stick with Nellie. You never know what might come up. But I'll call you Nell. When I'm not calling you Girl."

Her plan had worked. It had taken eight months to do it, but it worked. I was completely turned on to women's clothes.

Skirts were a revelation. Harriet got me a light but fairly full skirt in a floral pattern...delicious! I loved the way it felt on my legs. I would never have dreamed the faint swish of my nylons against the skirt could be so lovely. I loved the way it would flair out as I turned back and forth. It was fairly hot weather just then, but for a week I wore nothing at home but that lovely skirt. And at work, I would sometimes shut my eyes for a moment and think of my skirts and how they looked on me and felt on me. A skirt and a pair of nice nylons...heaven for me. And I would wish I were home so I could wear them. I imagined a bumper sticker: "I'D RATHER BE WEARING A SKIRT."

I began to notice what girls were wearing--well, I had always done that, but now I would see something and wonder how it would look on me. And I began to appreciate the marvellous variety in women's clothes. I had a gray suit and a brown suit. I had sports jackets in various tweeds--blue, light gray, dark gray. I had a blue blazer. And that was it. The only real color in my male wardrobe was in my ties. And trousers...short pants, long pants, chino or denim, cotton or wool. Nothing more. Trousers in a print...? Unheard of! And, looking through the catalogs Harriet got from mail-order places, I saw how much wider a selection women had. Short skirts, long skirts, every width from hobble skirts to full skirts, even one, I noticed, that was completely circular if laid on the floor. Solids and prints of every color and every description. Dresses or skirts and blouses or sweaters. And underwear...! Every conceivable kind of panties and bras and slips. And shoes: loafers, pumps, boots, ballet shoes, you name it. There it all was: a wonderful world of style and fashion, waiting for me to explore it.

And explore it I did. I would see a dress or a skirt in one of her catalogs and think, "I wonder how that would look on me," or "That looks so comfortable. I'll bet it would be great for casual wear." And I started studying the fashion section in the Sunday paper. Harriet would guide me in my selections: "No, that won't work on you. Yes; get that; it's You!" I set aside a certain amount of money each pay period in what I called my "Drag Fund." I didn't dare go shopping in stores, but there was no problem getting things from Harriet's catalogs.

I would come home from work, and the first thing I would do was shed my boy clothes and put on something pretty. A dress, or a sweater and skirt.

For my birthday, Harriet got me a pair of breast forms. When I saw some in a Freddie's catalog later, I was shocked at how much she must have spent. "It's time you had some proper boobs, Girl. You'll never be able to go out on the street with a chest that flat, and hankies just don't do it." I had never thought of going out en femme; this was strictly fun at home.

That night, Harriet lent me one of her dresses to wear. I just felt so good in it! I was swirling it about me when she said,

"I hope you realize that's the same dress I put on you last Fall. Remember?"

I looked down at it. Yes. Except for the fact that the nylons and underwear were mine and not hers, this was the exact same getup that had made me feel so ridiculous last October.

"I was right. We tried to do too much too quickly. And Girl, do you look smashing! I've never had a boyfriend who dressed up as nicely as you do. You could go out on the street like that and nobody would read you."

That made me nervous. That was the second time--no, the third time, come to think of it--that she had mentioned going outdoors en femme. That was a little too public for me. I didn't like to contemplate what might happen if I were "read," as she put it, by a gang of tough teenagers.

We did go out together shortly afterward, but I was dressed in my regular men's clothes. Our errand was getting my ears pierced. Harriet had found a place where they did good, professional work. It was a bit painful, but not as much as I had feared, and my ears healed quickly.

Harriet's next step was to teach me to act like a girl.

"You make a better girl than any other boyfriend I've ever dressed up," she reminded me. "I think you should make the most of it. But that means acting like a girl and not just looking like one."

She had a point. I was a little like Eliza Doolittle in Shaw's "Pygmalion"; I looked like a girl as long as I didn't move or say anything. The moment I got up or walked, the illusion was shattered. The only girlish things I knew to do were smoothing my skirt before I sat down and sitting with my legs tucked up next to me. Training in femininity was going to be a long, slow process, but by this time I was seriously getting into looking like a girl, and I was also a little curious to see how far I could go. Surely at some point, I thought, I would meet with internal resistance from my natural maleness.

She started with the use of the arms and hands. How to hold things, how to reach for things. How to hold my head and when to tilt it gently to one side. Smiling more often. The use of the eyes: when to make eye contact and when to avoid it. Then how to sit down and stand up. I thought I knew that, but there was more to be learned. How to walk--smaller steps and less weight on the heels. We spent a lot of time on that, because you can tell a man in drag a block away from the way he walks. I had to learn to walk more slowly, with a sort of gliding motion (I have always been a fast and purposeful walker), and to suppress the slight swagger that almost every man has when he walks. She got me shoes with higher heels now, and I had to learn to walk in them. They changed the way I moved my hips, and that helped. The details were endless.

She also trained me in the use of makeup and how to apply it. She got me a book, called "Color me Beautiful," which showed me how to tell what shades looked good on me, and what and how much to wear at different times of day.

She had me talk at a higher pitch (but not a falsetto) and in a breathier voice. And she worked on my vocabulary and the way I phrased things. Less declarative, more tentative. But, in the end, always back to the way I walked and moved.

"Suppose we put you back in your boy clothes. Do you think you could pass for a girl wearing them? That's the ultimate test, you know. Not just being in women's clothes, but being a woman in whatever you wear."

Looking ahead for a moment, I can tell you that in fact, more often than not, I go out in what I think of as "boy-clothes femme," and if I just walk the right way and move the right way, people address me as "Ma'am" and "Lady" and "Miss." I routinely shop for my dresses and undies this way.

That evening, I thought this was what she had in mind: getting me to go out en femme. But she had something else in mind. A couple of days later, she said,

"There's a friend of mine at work who's curious about you." I turned pale. Had she been telling other people about my dressing? I didn't like that at all. She went on, "...and he wants to meet you." HE?? "Mind if we have him over for drinks and dinner to-morrow?"

I minded very much. But I didn't want to argue with her. We rarely argued, and in those days I was feeling too grateful to her for getting me into all this to want to fight. And, I must admit, I was a little curious myself how some other person would see me.

Bob and Harriet came straight from work the next evening. He was a tall, good-looking blond guy. I had had the afternoon off, and I used it to prepare for my debut. I had chosen a dark blue dress with matching pumps, light nylons, a gold chain around my neck, and gold earrings. I had shaved a second time that day before applying my makeup, and I finished everything off with a bit of Arpege.

I found out just how good Harriet's training had been when Bob, introduced to me, said, "How do you do, Nell?" and then turned to Harriet and asked, "Where's Bill? Isn't he here?" He hadn't known I was a man, and he looked genuinely shocked when Harriet said that I was Bill. He hadn't realized.

Drinks were nice, and dinner was nicer. After dinner, we lingered over coffee and brandy, when suddenly Harriet said, "I just realized--I have to get breakfast for to-morrow! I had completely forgot about it," and disappeared.

Harriet never forgot anything. I wondered what was in the wind. I quickly found out as Bob moved over to the sofa next to me.

"Nell, you're one good-looking girl, do you know that?"

I gave him my sweetest smile and batted my eyelashes, the way Harriet had taught me.

"How long have you and Harriet been together?"

"Oh...a little more than a year."

He proceeded to draw me out. How we got along, how close we were. Somehow, in the course of this conversation, his arm brushed my shoulders. I wondered: did Harriet have this in mind? But he was an attractive man, and I was feeling more like a girl than usual. Maybe that was the result of the cocktails, the wine at dinner, and the brandy we were sipping now. I leaned a bit closer to him, and he drew me to his side.

"You smell nice, Nell. Nice old-fashioned name--Nell. I like it. Nell. Nellie."

I cuddled up more closely. He put his hand on my chin (was I glad I had had that extra shave!) and turned my head to his.

The kiss was dreamy.

And it was followed by a second kiss. It was harder than the first one, and I felt his tongue. I opened my lips softly and welcomed him in. Things moved quickly after that, and it seemed like only moments later that I was welcoming something else into my mouth.

I had never done that before. When I had had my "fling" with my roommate back in college, it had always been he who sucked me off. My mouth was virgin (as was my ass, too, for that matter). I hadn't known how a cock would feel in my mouth. With Bob it was like sucking on a bar of steel. And I was thrilled when he ran his hands over my shoulders and called me his girl as I pleasured him.

Harriet took a suspiciously long time, considering she was only going for groceries and that there was a shop only a block away. She certainly chose an...interesting...moment for her return, though. She managed to arrive just as Bob was coming into my mouth. I was just gulping it down when I heard the door.

I was sure she had set this up. But even so, I was half worried that maybe she would make a scene. But no; all she said was, "Was she as good as you hoped?" and Bob said,

"Harriet, believe me: she was terrific! She gives the best head in the New York Metropolitan area!"

Bob left about half an hour later, but not without a farewell kiss at the door. Kisses, actually, but he gave Harriet just a polite, perfunctory buss, and then he held me closely in a long and lingering embrace.

"We've got to do this again," he murmured in my ear just before releasing me. I was breathless from his kiss and could only whisper, "Yes."

We talked about it, Harriet and I, for the rest of the evening. She was curious to know what it had been like, how I had felt about it, and what we had actually done together.

"Harriet, that's so indelicate!" I exclaimed. "What do you want?...a blow-by-blow description?" and then I blushed, realizing the double meaning of the word "blow." Harriet picked it up, too.

"Blow by blow?" She giggled. "Just how many times did you blow him, anyway, Girl? You're a fast worker, I must say!"

But the experience told me something about myself. Something quite unexpected. I had liked it. It was like night and day compared with my first try at drag a year or more previously. I hadn't enjoyed that at all, and it took Harriet's long program of gradual acclimatization to turn me around. But I had known I was going to like sex with Bob from the moment he drew me to him and cuddled me. Nevertheless, I was still worried about Harriet.

"Harriet...you aren't jealous...? I mean, you pretty obviously set this up, with that story about breakfast...."

"Yes, I set it up. And I set you up. And no, I'm not jealous. If I were, it would be my own fault, after all. But there's something I never told you. I told you once that I always put my boyfriends in dresses. I didn't tell you that all my boyfriends end up in bed with other men. It's something I like to make happen. If you're going to dress like a woman, you should have sex like a woman, at least once. So you can have the whole experience. I like to watch, too, when I can. You looked terrific kneeling before him in just your bra and panties. I wish I could have taken a picture of you."

"You've taken pictures of...guys?"

"No. That's still an unfulfilled ambition of mine. I wish I had a collection of photos of my various boyfriends doing guys, though."

Knowing Harriet was proving to be an educational experience, in more ways than one. Her last words, when we went to bed, summed up the entire evening:

"Welcome to womanhood, Nellie."

Harriet and I broke up about three months later. We had been drifting apart, especially since I had been dating some friends Bob had introduced me to. But it came as a shock when Harriet announced that she was moving in with Bob.

"Well, he's your successor, you see. We've been...well... seeing quite a lot of each other. And in any case, I'm sorry to say it, but you and I are through. It's fun turning my boyfriends into girlfriends, but once I've done it, I lose interest in them. And when I've found the new boyfriend, I like to see if I can get him to use the old one as his girl. It sort of marks the transition."

She pondered. "Some time, maybe I'll meet a man I can't feminize. Then I suppose I'll marry him."

I stared at her. "You're a monster, you know."

"Oh, come on, Nellie. Think what you've gained from all this. Learning to love dressing up, and learning to be good at it. Learning to pass as a girl. And discovering that you're a talented cocksucker, too. I don't think you have had your last gay experience, Girl, not by a long sight. Actually, most of my men thank me once they realize what I've done for them."

In the end, the parting was fairly amicable. And afterward, I would occasionally run into them at parties, and Harriet and I always hugged and kissed. (And, depending on the kind of party it was, sometimes Bob and I kissed, too, especially if I was there en frmme. And a few times we got together and did a little more than hugging and kissing.) And Harriet had been right. She had taught me how to be a girl. She had opened a whole new world to me: the world of skirts, dresses, blouses, pretty sweaters, lovely undies, makeup, costume jewelry, and sweet colognes. It's a world I've come to love.

And although women are still my first love and always will be, for me there's a special sweetness in being dressed and in the arms of a nice man who's using me as his girl.

Princess Pervette March, 1997