Sought After
A Short Story
By Maryanne Peter

“Seeking an older sissy” was the posting on that sissy site. “I'm done with flighty, younger, gold-digging fembois, I want an intelligent but servile older sissy to serve me.”

If I had been your average 60-year-old widower and grandfather, who claimed to be heterosexual and normal in every respect, I would not even have been on that site. If I had been there only because I was slightly curious, I would have laughed and clicked back. But that is not what I did.

Somehow the idea suddenly had appeal.

I had quit my job to care for my late wife in her last years, and when she died it seemed that she had been the glue that kept our family together. Our two children lived far away from our small town in any event, but without their mother to go home to, they stopped coming. It might have been me, being busy and distant for most of their lives. No, all of their lives.

But in caring for my wife I learned that there is true nobility in domestic work, especially if it involves caring for another. Not only did I cook for her and keep the house very clean to guard against infection; I fed her in those last months, and toileted her and washed her, but I felt her love. I needed no thanks, just knowing how happy I made her was enough.

It seemed to me that I had spent my whole working life doing something that made nobody happy, and then when I went home, I found my true calling.

The dressing just came by accident, or rather by progression. She had aprons which I wore for practical reasons. Her tops were more comfortable around the house too, and on hot days some of her garments seemed to serve me as ‘kaftans’ – practical and not necessarily feminine.

At my wife’s funeral my male suit hung off me like a coat on a scarecrow, as I had lost so much weight. Only her clothes seemed to fit. When my family had gone, I slipped into her clothes where I was comfortable.

Somehow that seemed right.

I had let myself go a bit during this period. My hair, which was full and grey, had grown, and my beard, which was not so full, was long too. Dealing with a beard is easy – just shave it off. But I did not do that. I pulled it off. I used the strips that my wife had given up using years before and I pulled out my beard. I might have said that it was just because I was turning out her stuff in the bathroom, but I did not throw it away, I decided to put it to use.

You will have noticed that there is a theme developing here, which I should have noticed. If I did, I told myself that I did not. Perhaps the wax strips and moisturizing creams, but not the cosmetics; not the hormone replacement drugs for her menopause. Why would I keep those? Why would I use those?

There I was living alone, in my small house on the edge of a small town, in the middle of nowhere, slowly becoming a secret sissy. In the evenings I sat in front of my PC and accessed sissy sites, to try to understand what was happening to me and why.

It appears that there is no answer. Low self esteem might be a factor, and that certainly applied to me at that time. Crossdressing seemed an early indicator, but to me that was coming late. Homosexuality seemed the resulting condition, and I was not sure that I could function that way. But I felt the need to try. Sissy sites do have instructions on how to engage in anal sex, alone.

“Seeking an older sissy” the post read. “I'm done with flighty, younger, gold-digging fembois, I want an intelligent but servile older sissy to serve me.” I just had to respond.

“I am a sissy,” my email began, because by that time I was. I was sure of it. “I am a 58 years old, but I can be as immature as you like. I am intelligent, but I can be silly if that is what you want. I can cook and I am good around the house. I am a caring person and I want the person that I care for to be the happiest person in the world.” Send.

I tried to forget about it. I shut down my PC for close to 24 hours. I was nervous about turning it back on, but I was not sure if it was fear or excitement.

Inbox. A message from Colin. A manly name, I thought. I trembled a little as I opened the message.

“Hi Miranda. You sound nice. Please send me a photo of you in something pretty”.

I almost orgasmed out of my limp penis. I cannot describe how excited that it made me feel to be addressed as Miranda, let alone be called nice. I was thrilled. But what next.

I wanted to respond immediately, but I had nothing. There was no blonde wig, no pink frilly dresses, no white stockings or stiletto heels. There was only what I had. Then I found one of my wife’s few hats.

I could use my own hair swept across in front. I could wear the sweater I was wearing, and the black skirt, and a bit of jewellery, but the make up job would need to be second to none. And I was new to all of that.

I put a smock on, put a mirror beside my PC screen and I trawled through make up sites all over the web. I tried and failed a few times. It is much harder than it looks. Even
lipstick. I had watched my wife put it on so many times, and it looked easy, but it took me a while to master it.

I set my web cam to take a series of shots and with a bedsheet hanging behind me I struck a series of poses until I had an image that I was happy with. I emailed it to Colin.

After I had sent it, I started to think about all of the sissies in pink who must have sent him images. They would be wearing pink frilly outfits, maybe with bondage straps, perhaps with shots of their naked rear ends, begging to be fucked. There was no chance that he would go for me, fully clothed, not a shred of lace or ribbon in sight.

“You look so beautiful and sophisticated,” the email began. “Do you really serve? You look ready to take charge. If I wanted bumptious, I would choose a woman. I want a sissy. Are you really a sissy?”

I sent a two word reply: “Yes, Master”.

“Can we talk?” he asked. He sent me a voice link.

“Tomorrow night,” I replied. I did not have a voice. I looked at myself in the mirror, still wearing the hat and looking fantastic, but my voice could not come out of that face. I had work to do. I would need to go back online. I would need to record my voice and modulate it. Being a successful sissy was proving more difficult than I thought it would be.

24 hours later I made the call.

“Hello.” Colin’s rich baritone made me shiver. It was so manly that I knew in the moment that I had made the right decision. He was a man. I was not.

“Hi Colin,” I simpered in my Miranda voice. “How can I help you?”

“Miranda,” he breathed. I could sense the desire in his voice from the one word. It energized me. “I hope that you can help me. I am in desperate need of a sissy girlfriend. Could you be that person?”

“Maybe,” I teased. “Would you look after me and tell me what to do? I really don’t want to worry about deciding what to do.”

“If you were mine, you would never have to worry about anything,” he said. “I am rich, and I live a comfortable life but a lonely one.”

“Oh dear,” I sighed, sounding so feminine that it scared me a little. “But why would you choose an older sissy?”

“I am done with young ones. They are too like girls. They are greedy and stupid and think that sex is the answer to everything. Do you think that?”

“Sex is the answer, but not to everything,” I said. “Sometimes adoration is all a man needs.”

He was silent for a moment, and I wondered if I might have said the wrong thing. He wants sex, and that is all. But then he said softly: “You sound very wise. Wise and servile. Can they co-exist?”

“In me, yes,” I said.

“I think that you are just what I want,” he said. “Would you come to New York to visit me? You would be my guest. No obligation. Just to meet and talk. Give me your name and address and I will send you airline tickets. First class of course.”

That was it. A monumental change. A paradigm shift, as they say. Or at least the chance of one. I just needed to agree, and I could try it. Could I really leave all of this behind and take a look into this world? Leave what behind? This house? This town?

“Ok,” I said. I gave him what he wanted, and I always would.

The FedEx guy arrived in the morning. He gave me the pouch and said: “You have a nice day, Ma’am”.

I was wearing my wife’s robe, but I had been playing around with hair and makeup that morning. He thought I was a woman, and that made me feel good. I looked down the road towards town and wondered if I could ever walk in there again. Not looking like that, I could not.

I packed a few things (feminine only) and I got a cab to the airport. In the mall inside the terminal I went into a salon to have my hair done. I was wearing another hat, with wisps showing.

“Don’t tell me … you want something soft and feminine?” The salon lady had discovered my secret at a glance, which was a little demoralizing. “It’s not the look, it’s the movement,” she explained, and in the time we had she was to explain a whole lot more about appearing as a woman.

“You have very good hair for somebody your age,” she said. “Many women would be proud to have hair this good. And it is long enough to put some curls in. It will be unmistakably female by the time I am finished”. And it was.

I walked the length of the terminal with my wheelie bag behind me and a handbag over my shoulder, paying special attention to everything I had learned. I was ready for doubting stares, but all I sensed was a few admiring glances. The salon had done well: My hair looked great, my freshly waxed legs even better, and best of all, a professional makeup job. If only I could look this good every day.

The plane got into Newark close to 7:00pm. Colin had promised that I would be met. It was not him. It was a limo driver holding up a sign which just said “Miranda” and the name of my little town. It seemed like a good description for me at that time. Small town miracle.

“I’m Toke,” he said. I’m your driver”. it seemed unnecessary to say, but then I did not understand that he was my driver. “I’m to take you directly to the restaurant.”

Traffic was good. It only took 45 minutes. It was 8:00pm. I was nervous. I checked my makeup in the mirror. Toke opened the door. I got out as I had practiced in the salon. Toke escorted me inside.

He was waiting at the bar. Up until that point I had never been interested in men - being a sissy was about me - but I was certainly interested in this one. He was tall and stood without age, although he was clearly in his mid-sixties or older. His hair was white and hardly thinning at all. His skin was tanned and slightly rugged looking. It showed an active life well lived, and the smile showed that it had been a happy one, so far.

“Miranda,” he said, taking my proffered hand and pulling it up to his lips. He was much taller than me, but my heels were low. “Every bit as beautiful as your photo.”

“I am here to please,” I said with a smile. But I meant it. If he wanted me, I wanted to please him. That was my purpose as a new sissy. To find the object of my need – somebody to serve. I wanted it to be him. I wanted that so much.

“I have a table in the corner,” he said.

“Would you like me to follow a few steps behind, or hold your arm?”

“So thoughtful of you to ask,” he said. “Please, take my arm.” So I did.

The restaurant was French and looked expensive. It was probably the most expensive restaurant I had ever been in, but the menu was not unfamiliar to me. Still, I handed it over to him, saying: “I eat what you will have me eat.”

He smiled. He observed: “Sophisticated yet servile. Just what you promised.”

I smiled back. I was happy because he was happy, but I was happy anyway.

He ordered a bottle of expensive wine too, which he shared with me. I sipped only, to ensure that most of it went to him.

He asked about my town. He had never been there. That is no surprise. Who would want to? He seemed to want to avoid talking about my past, which suited me. It struck me that he was testing my intellect, by using some uncommon words. Did he want me to be a bimbo? Did he want me to say: “What does that word mean?” and pull out my compact to check my lipstick? I decided that the better policy was honesty. This is me.

“Do you know what this is?” he asked, when the appetizers were slid onto the table. “It is one of my favorites.”

“Pork jowl rillette,” I answered. “I can cook it for you if you like.” Which I could.

He said: “I have a cook, but that’s wonderful to know.”

“It can get messy,” I said. “Pulling all that meat off the head. It can get on my fingers. Some might even splatter on my face, or my cleavage.” That was a lie. I did not have a cleavage at that time. But why I was talking like this was a mystery, maybe to both of us. I guess that I was just trying to justify him spending money on me at the restaurant. That was not how a serving girl should be treated.

“Maybe you should make it for me,” he said. “And I could watch, and maybe help you clean up afterwards.”

“I would like if you would watch me serving you,” I said. “But only if you want to.”

“I think I could spend a lifetime watching you,” he said.

I wanted to ask him about himself. He was obviously rich. But why me? Why a sissy? Why not a real woman? If I could find one, he certainly could. But I waited until dessert before asking.

“With your permission may I ask one question?” I said, waiting for his approval before posing it in a whisper: “Why would you be interested in a sissy, and an old one at that?”

“I have had two wives and two families. I love women but I cannot live with women. Women are cyclical and temperamental, and that is not to my liking. I took on a transwoman mistress just before my second divorce, simply because she was uncomplicated. No risk of pregnancy. No demand for marriage. But still everything that I wanted in a woman with the libido of a man. But she wanted something permanent when I did not. But I got a second femboy partner, and that went very bad. I recognize now that what I want is somebody who will belong to me but can provide me with companionship. Your priorities change as you get older.”

“Don’t I know it,” I said. “If you told me ten years ago that I would be sitting in a restaurant in a dress and curls, offering myself to a total stranger, well … it could never have happened.”

“Yet here you are,” he said, dabbing his mouth with a napkin. “And I am accepting the offer.”

We were not picked up. We seemed to be in the heart of Manhattan, yet his home was only walking distance away from this restaurant, where he was clearly a regular. He did not even have to pay. It went on his account.

The evening was mild, and the air pleasant, as I held his arm again, and felt the strength in it, compared to my weak, pale, hairless sissy body.

“This is it,” he said. It was not a block of apartments but a whole building, an old brownstone. He could see that I was amazed, so he added: “I have a place on the beach on Long Island and a cabin by the lake upstate, but this is my principal residence.”

The house appeared even larger from the inside. He led me upstairs by the hand.

“That is your room there. Stay as long as you like. There is an open return air ticket on the dresser. The choice is yours. This is my room right here. Where would you like to go?”

“Where you tell me,” I said.

“Tonight, you get a choice,” he said. “But if you choose to enter my room, it may be the last choice you ever make.”

I have never been so sure of anything in my life. I almost barged past him to enter his room.

“Get undressed,” he commanded. It really was the first command I received from him. I loved it.

“I really do like breasts on a girly boy,” he said. “But your penis is suitably small, and shaved clean. I like that.” I wanted so much to have the body he wanted me to have. I put my hands up to cover my nipples in embarrassment.

“Bend over the bed, Miranda,” he instructed. I complied. I was ready. I had been working on this. There should be no pain, provided he used lubrication. But he might be bigger than my dildo?

“I have an enema kit in my bag.” I said.

“I don’t think that I can wait tonight,” he said. “But I do like a rosebud to smell like a rose.”

I turned my head and I could see that his pants were off and his underparts too. He was still wearing a shirt and tie, and a monstrous erection. It was the first that I had ever seen in the flesh, except my own, which was flickering into life.

Yes, he had lubrication, around and a little … up – ooh. I had to tell myself again: I can do this.

I felt the soft head of his hard penis kiss me and probe my back door. Then I let him slide in. It was nothing like the dildo. It was warm and pulsing. It was everything that I hope that it would be, and that was before he started to work it in and out.

I swear that in seconds I had a semi-orgasm, but he wanted to change positions. I wanted to comply. That was me now.

“Let’s turn you around,” he said. “I want to see your pretty face.”

I lay on the bed with a cushion underneath my buttocks, and I watched myself being fucked by a man. How had this gone so far in so little time? It should have felt so wrong, but it felt so right. Colin was inside me, pumping me, a look of happiness on his face that gave me joy. My soft body jiggled with every stroke. He was doing the work. That was the way it should be. I was just a scabbard for his sword; a vessel for his seed. His.

That is what came next. Well, him, that, and then me, in quick succession. He exploded into me and I exploded all over my own face. It seemed so strange and yet so wonderful, that I could only giggle. A squeaky girly giggle as if that semen had destroyed any manhood left inside me.

He looked down at my giggling cum spattered face with a huge grin.

“I think I’m in love,” he said.

The End

© Maryanne Peters 2020