A Submissive Sissy

Here you'll find my favorites Sissy & Femdom stories, the best one I've ever read over the net since many years and believe me, that's a lot ! I'm also a wool fetishist, so you may come accross this type of topic around here too... Hope you'll like it !

Kelly Ann Rogers

The Boy Nanny

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I missed the spring, when the dogwoods and cherry trees flower in Central Park, because I was in bed recovering. By the middle of May, however, I was equipped with a cute new face and a very slim but rather curvy little body. Although I was weaker than ever, I was ready to go. Sheila and Amanda had planned my summer for me, and I wasn't going to spend it at the beach in the Hamptons. I still had too much to learn.

First, I was signed up to work for Sheila's hair dresser. "You need to know how to fix a young girl's hair if you are going to be her nanny," Sheila explained, "and Amanda's hair as well, so you can take care of her properly." So I became a part-time apprentice to Roberto, at his rather upscale salon on Columbus Avenue.

At first, I was treated as a worthless, albeit decorative teenager. I answered the phones and swept the floor. I was now dressed in a more trendy way, but still with short skirts, tight tops, and heels. I especially liked a pair of chunky, high heeled Maryjanes that made me feel very stylish. One of the operators instructed me as I did my own hair first thing in the morning, and then I sat up front, acting as receptionist and gofer for most of the day. But during the second week, I was taught to wash hair, and then to roll it, dry it, and blow it out. Combined with the lessons Mrs. Spinner had given me, I became pretty good pretty quickly. The operators soon came to appreciate the help I was able to give them.

While at Roberto's I also got intensive lessons in makeup. It's one thing to put it on yourself, another to do someone else. I became proficient at both, and, just like I had under Mrs. Spinner's tutelage, I changed my face, or did one of the staff's, several times a day. I learned I had a good eye for color and shading. I kept trying to figure out what Tommy might like and decided to make myself look more mature, figuring he didn't want to go out (go out!?) with a kid.

I learned something else in that salon too. Roberto found me in the storeroom early on the third morning, as I was beginning to stock the workstations for the day. I had stopped for a moment to check my lipstick. This was now a well ingrained habit, thanks to the way Mrs. Spinner's used her crop on the backs of my thighs when I didn't keep myself perfectly groomed. Fact is, I looked terribly cute. I had on a short, red tartan plaid skirt, white knee socks and penny loafers. On top I had a twin set in soft, white, angora. It consisted of a slightly cropped, sleeveless top with a scoop neck cardigan. I had a matching white ribbon in my hair.

As I stood at the mirror, lip pencil in hand, the cardigan slipped off my shoulder, leaving it deliciously bare. Actually, I was practicing, letting the shoulder slip and then trying to slide it back up to look sexy. I was searching for the move that makes men pant; innocent and provocative at the same time. Sheila thought she was embarrassing me by sending me out in provocative clothes, and here I was trying to look even sexier. Hey! I was a teenage girl, what do you expect?

As I looked in the mirror, pouting at myself to be sure the pencil line I was making on my lower lip was even, Roberto appeared suddenly, with a strange look on his face. As I turned, he simply stepped forward, pinning my back to the mirror, and kissed me hard.

"Listen Missy," he sneered, "you do what I want or I expose your little charade. Then I'll tell Sheila that you won't cooperate. I hear she's just dying to find an excuse to take you to one of those meat market bars on 10th Avenue. A sweet little boy like you, dressed all femmy," he flicked at my skirt, "won't last 10 minutes before some big old brute stuffs his fat prick up your ass."

I had sort of forgotten that I was a 24_year_old male, and I was strangely offended to have Roberto remind me. I struggled briefly, but he was far too strong for my now feeble body. He reached under my skirt and grabbed my dick through my panties, pulling painfully at both rings,

"I'll yank this off, you little bitch. Stop struggling!" He gave another brief yank. "I want you to change our attitude, now! I want that hot little valley girl inside you to beg for my cock, and then I want you to suck it like it was the most important thing in the world to you!" My eyes got wide for a second as I tried to understand what he was saying. Smack! Right across the face. "Now!" he growled and pushed me down.

I cowered in front of him, on my knees. I was stunned, more from the situation than the slap. Events had overtaken me. I was a powerless teenage girl. Worse, I was a boy, who was a powerless teenage girl. Thoughts of how I had forced Amanda down on her couch rushed into my head as humiliation roared up within me. I was overcome with remorse now that I understood how Amanda must have felt as I betrayed her trust with my own strength and need for sexual domination. I started to cry. What a worthless sack of shit I am. I have nothing to lose. He wants a valley girl? He's got one.

I straightened myself, wiping the tears with the back of my hand. "Can I, like, please, like, suck your dick, Mr. Roberto, sir?" I peeked up from under my eyelashes before raising my face toward his with my most pleading look. "I know it will be like, just sooo yummy. I do so want to, like, lick and kiss and like fondle it. Please Mr. Roberto, can I like take it out now? I don't want to wait any more." And I pouted like a six year-old who didn't get her ice cream.

"Now we're making progress," he taunted, "of course you can suck it Ashley, sweetie. I would never keep you from having something you want so much. My sweet little pansy."

Stung with the shame of being called pansy, I lifted both my hands to his crotch, fingers spread on either side of his penis. My nails were really red this morning and they somehow looked right being there. I brushed his covered penis with my nails and watched it grow. Wow, did I do that? I turned my head sideways and planted a kiss right over the head, which was pointing almost straight up.

"Take the zipper down with your teeth," he ordered, breathing more quickly now.

I moved the flap of his fly with my lips to uncover the zipper, lifted the tab up by working my tongue under it, and grabbed it with my teeth. His pants were tight; it took me a number of tries to get the fucking thing down, and because I was rubbing my mouth all over his dick while I was working, it kept getting harder. Once I had the zipper down, I started to work on his belt. But Roberto couldn't wait. He pushed my head away and quickly unbuckled his belt and the top button of his slacks, and let the pants fall to his knees. He was wearing black nylon jockeys that were bulging with his erection. I licked its maybe six inch length with my whole tongue flattened hard against it. He moaned.

I reached up and pulled his underpants down and his erection started to swing out into my face. I lurched up before it came all the way out from his body, and grabbed it with my lips, sucking it in as if my life depended on it. I slid my hands up the backs of his thighs until I was cradling his ass. Then I pulled myself up and licked all around the head with my tongue. His precum tasted salty as I tried to stick my tongue right into the tip of his penis as if I wanted more. I tentatively tried to draw more and more of his penis into my mouth while I licked and sucked. After sliding it in and out only three or four times, Roberto grabbed my head and pushed. I gagged and he backed off a little. Then he came. Just like that. I swallowed some of his cum, and some ran out of my mouth and down my chin.

His dick quickly softened and he ordered me to lick it clean. I licked it from the base to the tip a couple of times and then concentrated on swirling my tongue around the tip for a few moments. "That's enough," he pushed me away. "Get cleaned up and go back to work." The whole episode couldn't have taken even three minutes. I wiped his cum off my chin with my fingers as he walked away. All I could do was sigh, fix my hair, and lipstick, and go back to work.

I never told anyone what happened, and he fucked my face almost every morning after that. I made believe I was like the many other women whose bosses had used their power to demand sex, but who felt too ashamed or trapped to admit it. Like many of them, I blamed myself. The good news is that he could barely last a minute before he came, so I was always done quickly. It even made me feel a little superior to him, in a deluded kind of way.

The bad news is that it made me feel like a whore again. And I got some kind of perverse pleasure from that too. I reveled in my shame. So, I tried to be "professional" with Roberto, practicing my technique and giving him a little show of moans and seductive body language, writhing around at his feet like I was in heat. This wasn't a whole lot different from what I used to do for the women who took me out. Except, of course, that with the women I was engaged in normal heterosexual sex and this was more like . . . , like . . . , what else can you call it, homosexual sex. Well, it wasn't like homosexual sex, it was homosexual sex, and I did my best to act like I enjoyed it. I told you that I was a good actor.

I didn't say a word to anyone because I felt sure that Sheila had given Roberto permission to do this and because I believed that I deserved what was happening to me. I was a victim now, and being a victim was restorative for me. For months I had been consumed with guilt because of what I had done to Amanda. Being punished like this helped to relieve that guilt. This was another component of my penance.

At 2:00 on Tuesday and Thursday afternoons, I went to cooking school. Actually, it was more like a school of culinary arts. This was fancy stuff, advanced techniques in kitchen skills my mother had never even heard of. Here I wasn't the frivolous teenager. I took this seriously, and I loved it because they took me seriously. They worked with lots of people in "domestic service," so I wasn't really a novelty, except maybe for my apparent age. But I am smart, and Mrs. Spinner had already taught me many basic techniques. I learned quickly, and I flirted with the teacher in a sophisticated way that he enjoyed. He was nice enough to flirt back without doing anything else. So, all in all, things went fine. By the end of the summer, I could have cooked in the restaurant where I used to wait tables.

At 4:00 was dance class. When Sheila told me I would be going I was elated. I had been working out again with Tommy and my body felt fine, although I was much weaker than I used to be. At 5'6" and now 115 pounds though, I was very trim and athletic looking. My tits (yummy) where growing along with my hips, but I was a long way from what you would call "womanly." The studio was up the street from Lincoln Center where I had trained before. Then it hit me.

"I can't go there," I stammered, always afraid to question Sheila. "Aunt Sheila, please, I used to dance there when I was . . . was . . ."

She cocked an eyebrow at me questioningly, but I couldn't say it. "A man?" She finished for me. I reddened with shame and broke down in tears. God, I cry like a baby at the least little thing.

She laughed, "Yes, you did, and I hope your friends there remember you!" She smiled at me brilliantly." I do so hope they'll make fun of you. But dancing again was your most fervent wish. I've arranged it, and you're going! And I'm sure you'll love it, won't you?" She cocked her head and arched that same eyebrow at me.

"Oh! Yes Aunt Sheila!" I lit up with forced glee despite the dread in my heart. I knew the look on her face all too well. "I'll. . . like. . . just love it. It's . . . like the best thing that could like happen, like, ya know? Like, for me?" I took a deep breath, feeling a little less panicky than a few moments ago. Falling back into my teenybopper persona somehow helped me to calm down, sorta like being with a familiar friend. Oh well, I might as well get something out of this.

"I saw some darling leotards in the store last week, can I like get some new ones? And like leggings to go with them? And I need ballet slippers! What colors should I get? Pink, I want pink, and white . . . Pleeeaaaase Aunt Sheila? . . . . Pleeeaaaase?"

I stared with big round eyes, tried out my new pouty smile (I really did like the way my lips curled up in the corners now), and swayed my upper body back and forth with my feet turned in and fixed in place, like a six year-old. It always startled me when I threw myself into one of these little girly scenes. It's like I'm possessed . . . , or that I had no shame. Well, I guess I proved that already with Roberto. It's just that I'm getting so good at this 'act,' I don't even have to think to do it anymore. It's my natural response.

For her part, Sheila always loved to see me debase myself when she forced me to act so intentionally girlish. Usually she would ask, "Where's our big bad rapist now, little girl?" This time she started to laugh instead, and then hugged me. "You're so sweet Ashley. Yes we'll get you outfitted properly, and buy some adorable leotards and a darling little bag for you to carry all your things in. I just love to shop for you." And she gave me a big hug.

I'm sure she didn't realize it, but that was the first time she had shown me any emotional or physical intimacy since this whole affair had started almost six months ago. She had been a major part of my life before, and when she emotionally threw me away after I had raped Amanda, a big hole was left in my heart. Her small show of affection on that day filled my heart right back up again, so quickly it almost burst. I hugged her back like I was clinging to life itself.

And so I found myself doing hair (and being forced to give blow jobs) in the morning and dancing ballet, en pointe, in the afternoon. I had variety in my humiliations. Like most ballet classes, this one was almost all girls, nine of them. But there were three young men in this class as well; it's just that one of them, me to be exact, was on of the girls. For the first class, I showed up in a pink leotard, white tights, and pink toe shoes. I had matching ribbons and barrettes in my hair, and although it was pulled back, Sheila demanded that I always wear it down and loose in back. The other girls, of course, were groomed for function. They wore their long hair up in tight buns or pinned up braids.

Sheila had set everything up with the teacher ahead of time, so I was introduced as Ashley, but everyone was told who I really was. That would have been bad enough, but not bad enough for Sheila, who saw to it that I also wore a long "Juliet" skirt. It was several layers of the thinnest white organza that slipped around my waist and went down (Thank God!) to mid calf. It flared out beautifully when I turned and flounced when I raised my legs. I was by far the most feminine looking person in the class. I also had one of the biggest sets of tits; my B cup bras were very full by that point. Ballet dancers are almost all small, and they all wear sports bras. I was still in a pushup, with a low-cut leotard, so all of a sudden, I felt like I had gigantic breasts. I was so embarrassed when they jiggled and bobbled while I danced. The other girls teased me unmercifully at first. You know, those cutting little comments tossed out of the side of the mouth as we danced side by side, or when we were changing.

"Nice tits honey, they make you look sooo graceful," or, "Hope all that jiggling doesn't hurt 'em," or, "Tits on a rapist. What a good idea. Yours are just right for you. They will keep growing, won't they?"

And then there was, "What a darling little skirt, sweetie. You are decked out to attract the guys aren't you? Or is it Janey, the redheaded dyke over there you're after?"

Janey had her own reason to look down on me, "What kind of faggot are you? You try to be a girl but you're not one everybody knows it. You're pitiful."

But after a couple of weeks most of the nastiness stopped. First, I think they just got bored, especially because I never rose to their bait. Second, my dancing improved rather rapidly, once I got the hang of the posture and lines required of female dancers, and once my feet got used to all the toe dancing.

At first, simply because she wanted to humiliate me, the ballet mistress worked especially hard with me on my feminine presentation and movements. And even though I wasn't really in the same league as the best of the other girls, I was pretty graceful before too long. And then, she began to enjoy teaching me because I actually listened to her and tried to learn what she was teaching. I threw myself into it. Being forced to be a girl was bad enough. But if I had to be one, I certainly didn't want to look like a boy in a dress, or a tutu, to be more exact. Besides, I had already learned that by throwing myself into my role, I could actually get some enjoyment out of it. I needed approval in ballet class just as I did in the rest of my life. If I had to get it by being the best female dancer I could be, so be it.

I guess that after a few weeks I just became another person in the class. Although I sometimes longed to dance some of the boy parts, just dancing was enough for me. I simply loved it, I adored it, I cherished it. There is a real thrill and a visceral sense of freedom in using your body in an athletic way, throwing yourself into a movement and feeling the joy of completing properly. So, unlike the other girls, who just wanted to get through practice with the least amount of effort, so they wouldn't get exhausted or hurt themselves, I threw my whole heart into it. I always tried hard. I think they admired me for that too.

Then, there were the guys. One was obviously gay. But strangely, both seemed to be attracted to me. Since I always tried so hard, they both wanted to partner me, which drove the other girls a little nuts. So I figured what the hell, the girls had been mean to me, why not I rub it in a little. I started to flirt gently with both the boys. I was subtle at first, but when Brent, the straight one, started rubbing his hands on me, I picked up my own level of enthusiasm a little. And the strangest thing happened, Jared, the gay one, who was much better looking than Brent, got jealous. He started to compete for my attentions. I wasn't quite sure what was going on, but it was kind of fun.

So that's how things went as we moved into the second half of June. I was learning to do hair, nails, and makeup at Roberto's. Oh, and I had become a really good cocksucker by then. Once I learned that he couldn't control himself, I started to do everything I could to get him to cum as quickly as possible. I started to time myself. I once got him off in less than 50 seconds. I didn't really understand why, but I felt kind of proud of myself. And what did it mean if I felt proud of myself for giving good head?

More normally, I was learning to cook, which I now thoroughly enjoyed, and some of my dinners brought me the most wonderful praise from Sheila, Amanda, and the others. Plus, I was allowed to dance. I was still Sheila's attentive, deferential personal maid on the evenings she was home alone, the demure, submissive dinner companion when Amanda visited, and Mrs. Spinner's assistant house keeper all the rest of the time. But things weren't that bad; they had almost settled into a comfortable pattern.