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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Chapter 1: Things Weren't That Bad to Begin With

I gently shifted little Emma into the curve of my right elbow, shrugged the strap of my gown off my shoulder, and pulled the lacy bodice to the side. She was already searching for the nipple with her lips, so she started suckling as soon as I placed her mouth against my breast. Once she had gotten a good grip on my nipple, I started shifting around, tugging at the seat of my gown and robe to straighten them so I could sit comfortably. You would think that after all this time I would have learned to straighten them before I sit. But there's been so much to learn. Breastfeeding Emma, for example, I really didn't know what to do at first, and then my nipples got dry and cracked, and then my breasts got sore when I tried to put off a feeding. But she is my baby, and breast feeding is so much healthier. It's just that I always figured it would be the mom who nursed the baby, not me. As sweet as it feels to have Emma suckling at my breast, I still feel a wave of humiliation surge through me as she starts. And because I'm now awake, I can't help remembering, yet again, hochaw the father ended up nursing his baby.

It was the week between Christmas and New Years and I was enjoying the relative calm in a somewhat deserted New York City. The schools were closed and the kids and their families away on vacation. The center of the city was crowded with tourists, but the neighborhoods weren't. That's something most people don't understand about Manhattan, it's made of hundreds of small neighborhoods, each a few square blocks. Mine was on the upper west side. I had graduated from Brown University two years ago with a major in drama and I was in New York to make my career on Broadway. I could act, I could sing, and I could dance. Oh, I knew it wouldn't be easy, but I was young and had started off full of hope.

By the end of 1998, however, I was frustrated and beginning to get more than a little desperate. I was working full-time as a waiter in a small upscale bistro not too far from Lincoln Center. I was good at it and earned pretty good money. This paid my third of the rent and supported my lessons in acting and dancing. Oh, how I love to dance. But the performing jobs have been too few to support me, and not always the kind I wanted. People like me well enough, but I'm finally beginning to figure out that my size really is a hindrance. At not quite 5'7" (OK, I'm 5'6"), I'm not much bigger than most of woman dancers and smaller than many. And a small leading man just isn't what producers are looking for these days. In fact, most of the jobs I got were for parts as teenagers.

But I was getting by for now, loving my classes, and, I had a way with the ladies. There are plenty of ladies in New York City, let me tell you. At 5:30 in the afternoon when the offices are letting out, attractive women are streaming all over the streets of Manhattan, beautifully dressed, heads held high, and looking for Mr. Right, sometimes just for an evening, and sometimes for longer. A good-looking, aspiring young actor was a pretty good catch, even if he really was a waiter.

After awhile, I discovered that the combination of my good looks, natural friendliness, and university education was attractive to a slightly older, more successful group of 30_something professional women. I learned that I didn't have to play macho with them and that it was better if I didn't. They preferred to be in charge of their relationships. Maybe that's why they were unmarried despite their good looks and brains. No matter how pretty, or sexy, or sweet they were, before too long their dominant streaks would scare off any man who might be their equal in brains, drive, or business success.

While I was as smart as any of them, I wasn't successful in too many other things (just for now, I hoped), and I certainly didn't earn much money. So, while these women could afford to take me to the opera, the best I could offer was my personal guided tour of the Metropolitan Museum of Art, when it was open free on Tuesday evenings. They took me to fancy restaurants and clubs in SoHo, and I took them for walks in Central Park, where I treated them as if we were long separated sweethearts. They took me to Fire Island or the Hamptons for long weekends, and I was charming and deferential, and made love to them as if we were doomed lovers with only one night left together. In other words, they treated me pretty much the way an affluent guy might treat a trophy girlfriend. I, in turn, did what was expected of anyone whose date just bought an expensive dinner.

This didn't bother me in the least. I had no problem giving what they wanted. I was discovering a submissive streak in my personality that I hadn't really known about before, and I was slightly appalled to learn that I liked having someone else in charge. I was content doing what they wanted and simply adored the time I spent with either my tongue or my dick buried in a pussy. They loved the attention, and I had no responsibilities in any of these relationships expect to be bright, engaging, and attentive. And, when I needed to be, I could be a very good actor.

Eventually, I was being shared by a loose circle of friends, all successful professional women. Two of the women in this group who seemed to enjoy me the most were also close friends. Sheila was a hard driving Ob/Gyn to the monied women on the Upper East Side. She was a workaholic, practiced medicine with a passion, and was completely loyal to her patients. She completely dominated me and just about everyone else she knew. Her need to dominate was too much for my taste at times, but she earned a fortune and figured that she could buy my tolerance and attention with fancy dinners, expensive gifts (especially clothes, she bought me an Armani tuxedo that was the envy of almost everyone who saw it), and by placing no demands on me when we weren't together. I guess I was a hot date when we were both available. She was also gorgeous, but created an almost unapproachable aura with her clothes and makeup. She usually wore her long golden hair tied tightly in a bun, slightly overdid her makeup, and preferred severe clothes. She liked to show me off as a symbol of the sexuality she buried under that cool professional demeanor. She also liked to pin me on my back and ride my hard dick for all she was worth.

"Look what I have, girls, don't you wish you could have him?" And they did, too.

I met Sheila through her friend Amanda, one of her patients. Amanda was just adorable. Sweet face, loosely curled dirty blonde hair that fell to her shoulders, and a lithe body. In fact, she was just about my size, but where I had a typically thin male body (with none-too-road shoulders, I'm afraid), she had curves. She was awesome in a tight sweater and jeans, but she mostly preferred a more feminine flowing kind of look, with layered soft tops and longish skirts that looked just sublime clinging to her tall thin frame. She also liked to trap my head under those skirts and squeeze my face into her pussy with her muscular thighs.

Their personalities were as different as their looks. Amanda was so charming and kind, she actually made me feel a little gooey inside. I knew that I was mostly just a diversion for her, but she made me feel like her lover. When we were together, it was my job to make her feel special, so I pampered her when we were out of bed and worshiped her body when we were in it. She never seemed to take this for granted. Unlike most of the women who saw me, she seemed to exult in my attentions, which only made me more eager to please her. We could spend a rainy afternoon curled up on a couch in the eight room apartment she inherited from her first mother (what she did with an eight room apartment except to hire people to clean it was beyond me), or watch a romantic girly flick together. When I was with Sheila, I had the feeling that what I was doing was kind of an obligation, but when I was with Amanda, I reveled in it. She made me feel needed even though she was the one who was in charge of our relationship.

Of course, I only saw her when she wanted to see me. She worked for a fancy auction house on the Upper East Side and traveled frequently to acquire the costly art, antiques, and other stuff that they then resold. I heard that she was the last person you would want to have to bid against. She was absolutely ruthless when she had to do business with someone who tried to take advantage of her. She used her sweet disposition and soft good looks to put men at ease. If you were fair with her, you got a good deal. If you miscalculated and tried to take advantage of her, she ate you for lunch.

There were others from the group as well, ad executives, lawyers, even a plastic surgeon, but those mostly came and went. The two girlfriends, Sheila and Amanda were the most constant thread in my relatively brief life as a sort of male escort in New York City. So, I spent my time charming the affluent people on whose tables I waited five nights each week, taking dancing and acting lessons, which were making me broke, and dating well-heeled women when they wanted me, which is how I got to live the high life in New York City.

Then the roof fell in. I had made the final cut in three straight auditions, but didn't get any of the parts. I was depressed and angry. I even had fight with one of the directors, who suggested that given my size and long hair, perhaps I should be trying out for some girl's roles. Then he had security throw me out. Real tough guy.

Not long after that, I had to go to work. I was still pissed off when I walked in, and quickly lost my patience with a little old lady who simply couldn't make up her mind between the clam chowder and leek and potato soup.

'Oh, spare me your drama,' I thought, rolling my eyes. 'Just pick a fucking soup.' It might not have been so bad, but while I was standing there watching her dither, another table was desperately trying to get my attention. I was in a no win situation and when the other table finally caught my eye, I managed to make the worst of it by pointedly telling the woman I was waiting for her to pick a damn soup already, other people needed me too. While I was in the kitchen, she had a talk with the manager. So did the people at the other table.

"You little prick," he yelled. "Who the fuck do you think you are! You don't treat my customers like that! Get the hell out of here."

"Well, fuck you too." I was gone.

Next, I had a fight with Sheila. I was still angry and she was feeling bitchy after a couple of long nights on call. Since she was the one paying for my attentions, I guess she had a right to be put off by my pissy mood.

"You little whore," she spit out, with more anger than insight, "I don't pay you to be bitchy."

Well, what could be meaner than attacking someone with the truth? That's just how I had been feeling, like a whore. My anger, which I never showed her, flared up, fueled by her nastiness and my own despair at not being able to get work as an actor or dancer, and having been fired from my menial job as a waiter.

"The reason you have to spend time with me tonight, or any other night for that matter, is because no one else in their right mind would spend any time with such a domineering bitch." After a few more acid insults from each of us, she threw me out.

So I went home, only to be confronted by my two male roommates, who had decided that they were in love, and needed their own apartment. Since one of them actually held the lease, I was the odd man out (which seemed kind of odd since I was the only straight one there). They gave me two weeks to leave.

Usually, when I was angry, I would walk along Central Park West, and my anger would dissipate in the beauty and bustle of the city. On this night, however, it just got stronger and stronger. I was swept away by my failures. I couldn't get work as an actor or dancer, I was about to be homeless, and I had prostituted myself to a bunch of well-off, overbearing bitches for nothing but a few fancy suits and opera tickets. Shit, their idea of a relationship was to exploit someone too poor to fight back. Fuck 'em all!

That's when I ran into Amanda. She could see I was upset and tried to comfort me. She took me back to her apartment, gave me all the wine I wanted, and let me rant and rave for a while. Then, she tried to comfort me with hugs and caresses. Little slut that I was, I started to get turned on. As my penis stiffened, I decided that Amanda needed to get laid. She disagreed and told me not to be a jerk and that "no" meant "no!"

In the end, what it came down to was that I raped Amanda. She said no. I didn't stop. I've been through it in my mind a thousand times, and that's still the only conclusion that really makes sense to me. I knew better, but I didn't stop. Lots of men might have said she had it coming, or that "no" meant "convince me," but I knew what she meant, and I ignored her.

Really, I was getting even with Sheila and all the other women who had used me (and this did include Amanda). But surely, of all the women I had known, Amanda deserved it the least. On that night, however, I wouldn't let myself feel that. Even after I had left her sobbing on the floor of her antique stuffed living room, I wasn't really aware that I had done something wrong. I worked hard to convince myself that she had asked for it. What I didn't know then, was that I was the one who was going to get it. Actually, by the time I went to sleep (which is to say, passed out), I didn't know anything. I had gotten as drunk as I'd ever been.

So, when I awoke the next afternoon, I wasn't quite sure if I should be worried or not. I went out to run my errands, pick up some fresh coffee at the Starbuck's on the next block, and bagels at the bakery on the corner of 81st and Broadway. When I got back there was a message from Sheila. She wanted to make up. Maybe I was just too stupid to hear the menace in her voice, or maybe she just hid it too well, but all I heard was an invitation to meet her at her apartment that evening at 9:30 for a late dinner. I had plenty of time. I straightened the apartment, even cleaning up after the two love birds who were about to throw me out, went for a long run in Central Park, and then joined a late afternoon dance class at the studio. By the time I got back and started to get ready to meet Sheila I was physically exhausted, mentally drained, and too focused on my thoroughly tired body to be thinking about last night.

When Sheila greeted me at her door, I wasn't really paying attention.

"Hi baby?" I offered tentatively, suddenly realizing I didn't know if she had spoken to Amanda.

"Hiiiiii baaaaaby," she responded, a little too cheerfully for someone who had heard Amanda's tearful story three times already over the course of a long sleepless night. I followed her in, momentarily captivated as she turned her back, which was beautifully bare because she was wearing a halter top tied behind her neck.

"Grab a drink. I've got a great Merlot open on the bar. I poured you a glass."

Well, good deal, usually she makes me open and pour. I grabbed the crystal goblet sitting on the bar, sniffed briefly (like I really cared about its aroma), and took a big swallow, then another. Good stuff! I drained the balloon shaped glass, refilled it, took a couple of more big gulps, refilled it again, and joined Sheila in the kitchen. As I entered, I noticed that there was no food.

"No food?" I asked. "That's strange; I thought we were going to have a late dinner."

"Oh, you'll be better off with an empty stomach. Can I get you some more to drink?" Since she had drugged my drink and planned to have me unconscious as soon as possible, she wanted me to drink up. Well, I had already consumed enough of that great Merlot and whatever else she had added to it. The world was getting blurry very quickly. The last thing I remember was the remarkable sparkle of Sheila's golden hair, and strangely, the three piercings in her right ear lobe, the one I must have fallen past as I slid to the floor, unconscious.