Strange Feelings

This is my first story about my life as a sissy.

To be specific, it's the first story I'm writing for my Mistress knowing she is going to have me share it with the rest of the world. I've written plenty of journals, stories, and research papers for her, but always with the understanding that they were private, shared only between the two of us. Mistress recently decided to change the rules.

Today is Wednesday, the middle of the work week. I am still holding down a job, though I think those days may be numbered. Mistress has told me several times that she doesn't need the money I bring in. And, if her home and lifestyle are any evidence, it's true.

My room is one of thirty in a palatial home that sits on ten acres just outside of Chicago. I moved in three weeks ago. I still have my place in the city, but I don't expect I'll be renewing the lease when it runs out in the fall. If our relationship continues the way it has--that is, if she decides to keep me--I won't ever be allowed to go back.

Which is fine. Because I don't want to.

---

The impetus for the story--the reason Mistress is having me write it--is that I told her I'd noticed something very, very strange today. Strange and scary. I asked her if I should go to a doctor, but she just laughed. She told me she'd been waiting for this day to come and that I should be proud of myself.

What it was--the best way I could describe it to her--was that I was having 'strange feelings'. Between my legs. Inside my belly. Across my chest and nipples. Let me explain.

I've always liked sex, always looked forward to it, always gave myself to it one-thousand percent. But, when it was over, it was over. I wasn't one of those men who thought about sex every time they saw a pretty girl or a big set of jugs. I knew where the lines were between fantasy and reality, between work and play, between sex and the hundreds of other things we have to do to get through the day.

That is, until today.

The lines blurred and vanished. I couldn't get my head out of my pants. I thought about sex every minute--from the time I left Mistress' home until I returned at the end of the day. It was an indescribable feeling. I wasn't hard, I was aroused. I was on edge. The kind of feeling you have just before a good cum. But there was more to it. I didn't get hard. And, my ass was hungry.

That's something else I never thought I'd say. But it was true. 'Hungry' is the only word I can think of to describe the feeling. I needed something in there. My memory kept going back to last night, to my first prostate orgasm. I'll tell you about that later.

Five times at work today, I found myself slid all the way forward in my chair, grinding my ass against the hard wooden edge. I went into the bathroom several times and tried to jerk off, but I couldn't get hard. If I took the head of my cock between my finger and thumb and rubbed, I'd feel tingly all over. I could see a drop or two oozing out, but I couldn't get myself to orgasm.

At the end of the day, Mistress' driver was there to pick me up, as usual. I spent the whole ride home leaning against the door, crying with frustration. I wondered what was happening to me. Was it permanent? And was it the result of what happened last night?

---

Last night was one of the best nights I've had since Mistress let me move in with her.

It was the first time she allowed me to entertain her friends. It was a small group. Three women, each of whom had brought a long a partner--though 'partner' may not be exactly the right word. They were submissive slaves. Like me.

Mistress Katherine, a tall, attractive German woman with short, brown hair and a sturdy build, was accompanied by a girl named Annie. Annie was slim and looked to be just barely legal. She had long, jet black hair and a boyish figure. I don't know what she was wearing when she arrived, but now she was naked. Except for black high heeled shoes and an iron collar that was heavy enough to make me wonder how she managed to stand upright.

Mistress Erica was short and muscular. She appeared to be eastern European, with long brown hair and bright green eyes. Her slave was named Edward. He looked like a body builder--broad shoulders and narrow hips--and was naked except for a stainless steel cock cage and a leather hood that left only his eyes and mouth exposed. His flesh was tanned and oiled and shone under the lights.

Mistress Jane was tall and heavy. I disliked her immediately. Her skin was pale, her hair a dirty blonde, pulled back in a pony tail. She was wearing oversized jeans and a flannel shirt, unbuttoned halfway down her chest, showing a heavy amulet that hung between her huge, sweaty breasts. She had loosely laced work boots on her big feet and was holding a rope. The other end was wrapped around the neck of a man who was even heavier than her. He must have weighed just under 400 pounds and was completely naked. He walked on all fours behind her, his bald head down, his cock and balls swinging between his flabby thighs. I never did learn his name. All night long, she just called him Pig. He looked uncomfortable, his eyes were slightly closed, like he was focusing intently on solving some problem.

I was wearing my maid's outfit. White stockings with lace tops, held in place by a beautiful garter belt Mistress has brought back from New York for me. My shoes were white with four-inch heels and ankle straps. My corset was laced very tight, the way she liked it. Laced tight so I would be short of breath all night. The bra gave me a respectable cleavage, even without saline injections or hormones. I wore shoulder-length gloves with open fingers and a white ribbon choker. The outfit itself was low cut to show off my chest, the skirt flared and so short that my ass and transparent cock-cage were clearly evident.

"You've all been invited because this is a very special night for pet," Mistress said, running her fingers through my long, blond hair.

"She has something to show you, don't you, my dear?" she asked, pulling me closer and giving me a kiss on my neck.

"Yes, Mistress, I do."

"Do you want to tell them? Or should I?"

Mistress slid her hand slowly down my side and I closed my eyes. I loved any tiny bit of attention Mistress showed me. My breathing slowed down and I moved my feet a few inches further apart. I opened my eyes just a bit.

"I'm very excited, Mistress. May I tell them?"

Her hand ran over my skirt, then I felt her nails touch the outside of my thigh. My cock started to stir. I felt the chill of plastic on flesh and held my breath. Even after weeks of chastity training, I still started to get hard when I felt her touch me. I opened my eyes slightly, tried to focus on one of the beautiful blue designs in the inlaid tile floor. It didn't help. My cock strained.

I looked up slightly and caught Pig looking at me. His tongue was between his lips and he was rocking his hips forward and back. I could see his nostrils flaring as his breathing got heavier. His movements were subtle but he could tell I noticed. He looked me in the eyes, his face a complicated mixture of arousal and some kind of anxiousness.

"Mistress is going to show me how to cum without touching myself," I heard myself say.

Two months ago, it would have been impossible for me to say something like that. Even now, I didn't know which part I thought was hardest: that I would say something like that to six complete strangers, or that I would be looking forward to such a thing, or that I would be calling my prick a 'clitty'.

But, I didn't care. Not any more. I was completely committed to Mistress. Nothing else mattered.

"How exciting for you," Mistress Jane laughed.

"You're gonna be another faggot perv sissy," she continued. "Oh boy. Just what the world needs." She nudged Pig gently, the toe of her boot against his belly.

"Maybe we'll fatten you up and you can look like this one, hmm?" Pig stopped rocking and lowered his eyes. I saw his shoulders shake and wondered if he was crying.

"Bring my friends their refreshments, pet."

I nodded.

"Yes, Mistress."

I went to the kitchen and opened the big, expensive fridge. Mistress had had me memorize all of her friends' favorite drinks and I knew the refrigerator would be stocked. I poured Champagne for Mistress Katherine, Montrachet Grand Cru for Mistress Erica and opened an ice cold can of Budweiser for Mistress Jane.

I carried the glasses--and can--into the front room on a silver tray. I moved from woman to woman, letting them take their drink, then put the tray on a table near the door.

"Come here, pig," Mistress Jane said. Pig crawled to her and settled back on his feet, raising his hands up into a 'dog begging' position. Mistress Jane tilted the can and slowly emptied it into his open mouth. She patted his belly and threw the empty can to me.

"Bring him another," she said. Pig trembled.

As I walked back to the kitchen, I realized what Mistress Jane must be doing, why he was looking so anxious. Poor Pig. I brought the can back and handed it to Mistress Jane. She leaned down and kissed Pig on the mouth. Then, she gently pressed his forehead. He lowered his arms and tried to relax.

Mistress took another sip of her scotch then handed the glass to Mistress Erica. The room was quiet, I could hear Pig's strained breathing.

"Pet? You have a choice to make," Mistress said to me. She nodded her head and I saw Annie and Edward take a step toward me. Pig crawled toward me, stopping when he was a few feet away. Annie and Edward stood on either side of him.

"You get to choose who will be helping you have your first hands-free orgasm." Behind me, I heard Mistress Katherine, Mistress Erica, and Mistress Jane giggling and clapping their hands like teenagers. They were laughing and guessing which of their slaves I would pick.

"And while you decide, why don't you tell us all what you've been doing to prepare for tonight?" Mistress said, taunting me. She took her glass of scotch back from Annie and took a sip.

"I think it will help get our little pets all turned on and ready, don't you?"

Edward was the first in line. I stepped in front of him and ran my fingernails up and down his shiny, oiled chest.

"Mistress started off making me masturbate for her several times a day. I lay on the floor, or on my mattress, or on Mistress's soft, soft carpet, and lubed my hands so they were so, so slick..." I leaned forward and kissed Edward's left nipple, wrapping my lips around it, sucking gently.

"Mistress sometimes let one of her other girls suck my titties, just like this..." I moved my mouth to his right nipple, licked and sucked.

"Then, when I started getting stiff, I would reach down and slide my skirt up..." I ran both of my hands up and down Edward's thighs, from his knees to his crotch. I saw how hard he was working to not get aroused, knew he would fail. He and I both knew it. And we both knew what it was like to feel our clitties swell inside those metal cages. But I didn't care. I'd played with other caged men before and I knew that I liked it. I liked the feeling of power it gave me--a slave--to tease another man like that.

"And I would jerk and tug and pull my long, hard cock until finally..." I slid my hand between Edward's legs, ran my nails along the underside of his sack.

"...I couldn't take it anymore..." I leaned forward and kissed him genty, ran my tongue along his upper lip.

"I stroked faster and faster until, finally..." Edward was starting to shake now, the way I'd seen other men shake when it got to be too much. I saw how swollen he was getting, how his cock strained against the metal bands, and smiled.

"I'll bet if you're the one I pick, you'll fuck hell out of me, won't you?" I stroked his cage with my fingertips.

"You'll love being in my tight little ass, won't you? You'll fuck me good, won't you?"

Edward leaned toward me just slightly and gave a sneer.

"Fuck. Yes. I. Will. I'll destroy that little ass of yours..."

"Good," I said, as sweetly as I could. Then, I knelt down in front of Pig.

"Well, I did that for a while. Several days, in fact..." I stroked Pig's cheek gently with the back of my hand.

"I came a LOT, quite a lot, before the first time Mistress introduced me to the beads. The first time I used the beads--a string of six--I pulled them all out at once. Imagine!..." I inched my way around Pig's side, my hands lightly gliding up and down his spine.

"Mistress taught me to grind those beads up inside of me while I stroked my clitty. She taught me to pull them out slowly. One. At. A. Time..." I pushed my finger up inside Pig's ass, just an inch or so. I couldn't have Pig pissing all over the floor. That was Mistress Jane's prerogative. Pig, of course, didn't know what I was up to and was scared I'd make him unload his bladder right then.

"Please, please don't," he whispered.'

"Shhh...shhh..." I whispered as my hand slid underneath his belly. I closed my fingers around his tiny, flacid prick and gently stroked.

"Am I exciting you, Pig? Where was I? Oh, yes, the beads. After I got used to cumming with the beads in me, Mistress started me using a dildo..."

Pig whimpered as his little prick got stiff. It was only about five inches long and thin, but hard as a steel rod. I could feel that Mistress Jane had had him surgically altered. His cockhead was huge, nearly the size of a small apple. And there were bumps every inch or so along both sides of his cock. I'd heard of things like this before but had never actually seem them. She'd had steel balls surgically implanted just underneath the poor thing's skin. I felt my own prick stir when I thought about how that would feel up inside of me. How funny that I'd been telling him about how much I liked the beads and here he had his own set.

I stroked Pig a few more times, watching his face, seeing how hard he had to work to control himself and not wet the floor. When he started twitching in my hand, I let go and stepped in front of Annie.

"And you, my dear. I suppose you'll be wearing a strap on?" I slid my hand between her legs, felt that she wasn't very wet.

"When was the last time anyone has been inside your cunt, dear?" I slid my finger between her dry lips, pressing at her opening.

"No one wants to use me that way, Ma'am," she said.

I looked into her eyes and smiled.

"Yes, I can understand that. You don't have much of a girl's body, do you, Annie?"

I pushed my finger into her mouth.

"Get me wet."

She licked my finger, forced up some more saliva, licked it again.

"You have such small titties, and such slim hips," I said as I pushed my wet fingers into her cunt.

"You're more a boy than anything else. No wonder they brought you here tonight." I let my thumb slide across her clit while I pushed my fingers deeper inside her. She came very quickly and I smiled.

"Oh, I think I like you best of all," I said, stepping back and wiping my fingers on a towel. I turned to Mistress.

"Yes, Mistress, she's the one."

Mistress Katherine smiled. She'd won the bet. She collected $50 from each of the other two, then took Annie by the hand and walked her to the cabinet where Mistress kept all of the dildoes. Annie took the harness from its peg on the wall and pulled it on, adjusting the buckles until it fit snugly around her waist and thighs.

Meanwhile, Mistress and the others discussed which of the dildoes would work best on me. I was excited and anxious. I felt my belly churning. I watched and listened while Mistress picked up and described the different dildoes she'd had me use on myself these last few weeks and how I'd reacted to each one. I felt myself blushing, embarassed as she described how I would lock the dildo into its mount, lube it up, then straddle it, lowering myself slowly until I'd taken the entire thing up inside of me.

"And then, the girl would ride it up and down, sometimes for 30 or 40 minutes, all the time, jerking herself off with one hand and playing with her titties with the other. Isn't that right, pet?"

I nodded, my face bright red, my eyes looking at the floor.

"When she came, I let her stop fucking herself. The first few times, she coudn't stand up after that. Her legs were exhausted. But it was good exercise for her, wasn't it, dear?"

"Yes, Mistress. Thank you, Mistress." I said.

Mistress showed them the biggest and longest one I'd taken so far - eight inches long and a full two inches around. It was curved and had a series of small ridges just where it would hit my prostate. I remember how excited I'd been, the strange tickling feeling I'd had.

Evidently, Mistress Jane noticed the way I was staring at the dildo because she started stroking it slowly and walking toward me.

"You love this one, don't you? You hungry cunthole. You nasty little fuck." She slapped me, then grabbed my hair and pulled my head back.

"I'll be you'd love this one in little Annie's harness, wouldn't you?" She let go and pushed me away.

I stood trembling, unsure what to do, wondering how Mistress would like me to react. I wanted her to be proud of me, but I wasn't sure what she would expect me to do.

"Thank you, Mistress Jane," I said. I saw Mistress smile and a warm feeling went through my body.

Mistress ended up choosing a shaft that was slightly shorter and curved a bit more sharply about a third of the way from the tip. She helped Annie secure it to the harness then smeared it with lube.

"Open your legs," she said, stepping toward me, her hand scooping up another load of the slick silicon gel. I immediately spread myself and felt her hand slide up between my cheeks, then her slick fingers were deep inside me.

"I think you're ready," Mistress said to me, pulling her hand out of my and wiping it on a towel.

"Get on your knees."

I got down on my hands and knees and raised my ass in the air. I felt Mistress' fingers inside me again, pushing more of the lube into my open ass, her fingers twisting and turning as she pushed deep then pulled back out.

Mistress squatted in front of me and took my face in her hands.

"This time, we leave your cage on. It's going to feel very, very different for you. But I promise you're going to enjoy it." She gave me a gentle kiss on the forehead.

"And it's important you learn to cum like this. The odds of you being told to put your prick in someone's mouth or ass ever again are not very good. You're much too femme a sissy for that."

I felt a cold fear go through me and bile rising in my throat. I thought I was going to be sick. The thought that I would never fuck or be sucked off again was like a death sentence. I didn't imagine I could live like that. I felt tears welling in my eyes and could tell my lips were trembling.

"See? This is how I like my girls to behave!" It was Mistress Jane. She was standing next to Pig, holding his head with both hands, making sure he was looking at me.

"This little whore knows her place. No more fuckkee. Ever. See how happy she is? Crying tears of joy."

Pig just nodded.

"Yes, Mistress. I will try to do better."

I felt a flood of disgust go through me. Pig must have been a man like me. Once. A long time ago. Now, he was just a toy for this pale, fat bulldyke looking woman. Would I end up like that? Would Mistress hand me off to someone else at some point?

My thoughts were interrupted when I felt Annie kneeling down behind me. She pressed her thin thighs against the backs of my legs and I felt the head of that big strap-on prick sliding up and down between my ass cheeks. I tried to look up at Mistress but before I could, Annie slid the cock into me in one quick stroke. It went in easily, all of Mistress' work stretching my ass paid off.

Annie slid the dildo slowly out of me, then froze in place for a few seconds. When she slide back in, she tilted her hips. I felt the edge of the dildo pressing against my prostate and moaned loudly.