A Sissy's Breakthrough

I took a deep breath and sank to my knees just inside my front door. I didn't know exactly when the man I had recently returned to calling Sir was going to show up, and he liked it that way. The door was unlocked, and any time within the next hour it was going to swing open.

I had been warned that when it swung open I needed to be on my knees, hands behind my head, mouth open, tongue hanging out. If I was not, Sir was going to turn around and I would never see him again.

I couldn't blame him for being strict with me. I had recently flaked on him, stopped answering texts and messages and just buried myself in my embarrassment and shame. Any sissy can tell you what it's like or what it's about. What am I doing, is this what my life is going to be, I just want to be a real man, on and on it goes.

Well, I had done the purge cycle before and this time I just shoved everything into a box and shoved the box in the back of the garage, which in retrospect was more or less setting myself up, wasn't it? I chewed on the shame for a few weeks before the box was out again, and a little while later I was dressed and had locked myself in chastity, and as the dildo sunk home I realized I wanted, badly, for it to be Sir's cock in me. Unable to resist how horny I was I had unlocked myself and stroked to an orgasm, which had me surfing a mini-PNC wave and putting off texting Sir for a few days, but it was only delaying the inevitable.

He responded quickly when I finally got in touch, which added an additional layer to my embarrassment. He could have been childish and ignored me, but instead he just directly communicated his thoughts and feelings. I had broken his trust, he said, and he wouldn't do anything before we met in person and talked it out.

We met at a coffee bar halfway between our houses. He was less Master than I'd ever seen him, and more hurt and disappointed than anything else. He liked what we had, he said, he liked me, and it was a real disappointment when I disappeared. He understood, he stressed. He had dealt with his own shame and guilt about being queer, about his urges to dominate, control, humiliate and hurt others. He had flaked on people, which was a big reason he didn't consider it an unforgivable sin. "Plus," he finally said, "I still want you."

I must have been blushing as I looked down, and I think that flipped a switch in him. He was Sir again. He had said what he needed to say, I had apologized a few dozen times, and my little sheepish turn to looking at the ground allowed us to pick up more or less where we had left off.

"Look at me," he said to me. I did. "Stand up, go outside, and wait for me in front of whatever is next door."

"Yes Sir," I practically whispered. I did so and could hear him standing and exiting behind me. As I turned to stand in front of what turned out to be a closed dry cleaner he was right on top of me, gently pushing me against the window and taking my hands in his and curving them back behind my back.

Moving to the street had given us a bit of public privacy - people were walking by, but nobody really cared about two guys who looked like they were about to make out, even if one of them was clearly 10 years older than the other.

He held my hands behind my back and kissed me, equally forceful and sensual. I was getting "I'm glad you texted" in the kiss, while his hands found their way into my waistband at the back. As he felt my ass, he couldn't help but notice the satin thong I was wearing. One hand drifted around to the front, where it felt the hard plastic of my chastity cage.

"You're locked?" he asked. I nodded and he smiled at me. "Good girl. Give me the key." I hung my head and dug in my pocket to hand it over. This was exactly what I'd been hoping would happen, and the fact that it unfolded just like that made me feel incredibly submissive. Dominance and control was exactly what I needed, and I was incredibly grateful I was getting it.

"I'll text you instructions," he said, and walked away.

We had met Thursday evening, and we had a habit of playing on Saturday nights, so I had two miserable nights in chastity to get through. He had texted me shortly after I got home, telling me that he wanted me to spend at least an hour each night with a plug in, and to send him photo proof at the beginning and end of the hour. That was easy enough, and honestly knowing he wanted me stretched had me incredibly excited for Saturday.

In response to the picture I sent at the conclusion of Friday's hour, he texted back a set of instructions. I was to make sure I was hairless below the eyes. I was to clean myself inside and out and do my makeup to the best of my ability. I was to outfit myself in my heeled stockings, my garter belt, thong, corset and bra, paired with a blonde wig and shoes of my choosing. And then I was to get on my knees and wait. It only being an hour that I had to wait was something of a mercy, but I spent that hour with my heart beating pretty fast.

I don't know if it was minute 59 when I heard his footsteps on my front steps, but it must have been close. I opened my mouth as wide as it could go and tried to get my tongue out even farther. I didn't just want to avoid disappointing him, I wanted to impress him.

If he noticed my efforts, I did not see him notice. Instead the door swung open, he took a big step in, threw a small duffel bag on the couch, and then slammed the door behind him as he took out his cock. Stepping forward, thrust his cock into my face and said only one word: "Suck."

I took his cock in my mouth and as I felt it begin to harden I let out an involuntary moan. I had missed this, and as he began to pump it back and forth over my painted lips I knew he had missed it as well. Before long he took to working it as far back in my throat as he could, pulling back a bit to let me breathe, then trying to go a bit deeper. I sat back and gripped my heels with my hands, not wanting to instinctively try to grab at him or stop him. I wanted to be his cock hole and he was happy to oblige.

After a few minutes of that he pulled all the way out and slapped me across the face, hard. An honest, forceful cock slap was always stronger than I remembered and I loved every second of remembering. He pulled me to my feet and spun me around, pulling my hands behind me. I felt him squeeze them together, then felt a handcuff encircle one wrist, then the other. I pulled at them just because, but they didn't budge. Police issue, the ones with the hinge in the middle rather than the chain.

He took my elbow and marched me down the hall to my room. Giving me a final shove, I fell face down on the bed. I felt his hand on my neck, pinning me down as his other hand started pulling my panties off. I squirmed out of them for him and he immediately used his feet to spread mine apart. "Do not move," he told me and I heard him walk back to the door for his duffel bag. A moment later he was tying each of my feet to a bedpost, leaving me spread wide. He stepped back for a moment to admire his work and I squirmed for him.

His admiration warmed the part of me that I didn't like to admit existed. To be his sissy, the object of his desire, of his intense lust, was incredibly and intensely fulfilling. He was going to take me, because I was his, and there was nothing I could do about it.

"A few final touches," he said, first going into the duffle bag for a blindfold and a ball gag, both of which went on. Then he crouched at the foot of the bed and pulled my locked up cock from beneath me, positioning it so it was draped over the edge of the bed, pointing down. I heard him pull out a key ring and a moment later I could feel the tube sliding off of my chastity device.

I was a bit stunned by this - I thought his taking the key was an attempt to push chastity forward in our relationship, and I had assumed that he was here to use me and ignore my pleasure. I realized this evening might have more dimensions than I had first assumed.

My thoughts ceased and I let out a long, low moan as I felt his finger slip into my ass. It was quickly joined by a second and then a third, and I could feel him gently stretching me. The previous nights with the plugs had paid off, though, and both of us could tell that I was already ready for him. I heard him take off his clothes behind me and a moment later I felt his hard cock at the rim of my ass.

I moaned again as he slid it in, louder. He worked back and forth shallow for a moment before sliding in his full length, which was generously above average. I was in heaven. {(MORE ON THAT MAYBE)

With his full length buried in my ass I felt him pause. Instinctively I turned my head, though I realized as I was doing it that I couldn't see what was happening and also couldn't say anything remotely understandable. I felt him shift around while maintaining his depth and heard a squirt from the lube bottle, and then I felt his hand around my little sissy clit.

My breath caught in my throat. He had never done this before - I had earned his attention to my sissy clit before but he preferred to make me vibrate it like a good girl and not pretend I was a real man, stroking away. I felt myself quickly get hard in his hand and thought it might make for a more interesting experience getting fucked, but then I processed that he wasn't pumping away, he was focused on stroking. I made a "what's happening?" grunt behind the gag.

He took his hand off my cock and leaned down to whisper in my ear. "This is for your own good," he said. He resumed stroking. It felt incredibly good, being full of his cock and also getting the sensations of what was honestly an expert level hand job. I was moaning behind the gag every other second, drool soaking into the duvet under my face.

And then it happened. I exploded in orgasm, grunting loudly into the gag and feeling my whole body contract around his cock and spasm outward. I took several sharp breaths and slumped into the bed, and then it descended on me.

Every sissy knows the feeling. "PNC" is a bit crude as an acronym, but that's what it is. You orgasm and all of a sudden you realize this isn't what you want, it's ridiculous to go this far in pursuit of a fetish, you look terrible in whatever getup you've got on, you're never going to build the life you want like this.

The exact specifics of what the moment says to any individual tend to vary but the overall vibe is the same, and it can drive some pretty substantial feelings of regret, self-loathing, and shame. And one thing that really came through for me in this moment, is that it's something of an old friend. I don't need to think each individual PNC thought for them all to be there. It's just a heavy blanket that I'm under all of a sudden. And, I realized as I lay there, I was under that blanket with Sir's cock up my ass, handcuffed and tied to the bed, blindfolded and gagged.

Whatever noise I made must have given some inkling of what was happening with me, but Sir's first response to this was to take his hand, which was covered in lube and the load I had ejaculated, and smear it across my face. His second response to this was to start taking long, deliberate strokes, his cock almost leaving my ass and then coming back to full depth.

I made another noise, something between distress and desperate confusion. He paused in his pumping and leaned down again. "You have a safeword and you can use it," he said, "but I am really hoping that you trust me." And then he resumed his moderate tempo but thorough fucking off my ass.

I got lost in my head for a few minutes. "I feel ridiculous," I know I thought, and my head went through my outfit. The size 14 heels, the empty bra, the corset I had to wear upside down because I didn't have the hips for its normal orientation, the heavy, hot wig. His cock in my ass wasn't painful, I was experienced enough with ass play for that, but it was awkward and uncomfortable.

I knew my makeup was going to smear on my duvet and I reflected, not for the first time, that for some men that happened because they were fucking a woman. "Real men do not do this," I thought. Then the smell of cum re-asserted itself and I did another round of "real men do not do this."

I'm half convinced Sir can read minds, because he leaned down again to whisper into my ear. "Real men don't exist," he said, "and all you need to be is a good whatever it is you happen to be." And with that he put one foot up on the bed, angling himself forward, the effect of which was to make his strokes connect directly with my prostate.

So now I felt ridiculous, was nauseated by the smell of cum, and was wrestling with the potential implications of "real men" vanishing from my concept of existence, and on top of all of that I had waves of pleasure building in me. "At least there's that," I thought.

"Okay," I thought, "real men are a fake idea. All I need to be is a good whatever I happen to be." Was I a good whatever I happened to be? What did I happen to be? The obvious answer was "sissy," and I felt like that fit. I didn't really choose it, not in any original sense. I chose to explore it, to indulge in it, but the idea itself was, more or less, dropped on me.

A teenage me saw a friend's panties and thought "I wonder how those feel" and conspired to try them on (sorry Jess!) and they felt good. And I looked good in them. And it was a straight line from a stolen moment while the pool party raged outside to this moment here, where Sir's cock was building a rhythm and really hitting me.

So "sissy" is what I happened to be. Was I a good one? Not when I flaked on Sir, certainly. But what about when I did my eyeliner three times because I wanted Sir to like it? What about when I bothered to email the corset company and ask which model was going to work best for my decidedly male dimensions? If I wasn't a good sissy, I thought, I certainly could be. What was stopping me?

What was stopping me? It was a good question. Just the feelings I was feeling, I realized. The ridiculousness. The shame. But who was responsible for those? I didn't look ridiculous to Sir. Nobody who thought I should be ashamed of myself for my kinky acts of depravity was in the room. So what was stopping me was...nothing? I sat with this idea as Sir picked up the pace, and another involuntary moan escaped me.

"There she is," I heard him say, and I blushed behind the cum that was drying on my face. I moaned again, intentional this time, but reflective of very real feelings that were building. "Lean into it, baby," he said. I felt my hips start to rock, trying to match the rhythm of his strokes. He grunted, which I took as encouragement. "Are you my good little sissy?" he asked me.

"Uhhh," I moaned. The gag was still in my mouth so I'm not sure how comprehensible I was, but I gave "I just want to be your good little sissy, Sir" my best shot.

"Good girl," he said, and he picked up the pace even faster. He certainly knew what he was doing back there. The angle was just right, and the constant on/off of direct prostate stimulation was building and building.

"God," I thought, "it feels good to be a sissy." The thought stuck with me. Why overcomplicate it? Life is short. Everything that made me feel bad about it came from outside of myself. Everything inside of myself was busy enjoying getting railed by a sexy, experienced dom. I moaned again.

I could feel the waves building now, and I quickly called out to Sir before I got too close. "I might have to cum Sir" turned out to be completely unintelligible behind a gag, so SIr unbuckled it and let it fall out of my mouth. I tried again.

"Do you think you deserve to cum?" he asked me, not missing a stroke in his fucking.

"No Sir," I said. "I already got one orgasm and I just want to be your good little sissy fuckhole."

"Good girl," he said, and I melted into the bed. The only issue was he was still giving me an expert fucking and I could still feel the orgasm building. I squirmed to try to change the angle or get him off my prostate for a second. He put a hand on my neck and pushed me down into the bed.

"No," he said. "I want you to fight it. Focus on being a good little fuckhole. I'm close, you fight it until I cum."

"Yes Sir," I said, "ohhhhh, thank you Sir. Thank you thank you thank you." For the fucking, for pushing me, for everything else. I tried to relax, let my body go limp, knowing contractions would probably hasten my orgasm. His hand tightened on the back of my neck and he got even faster, really slamming into me. A short bit of that got him there, and I heard him explode in a grunt and felt him cum inside me. God, I loved that feeling.

He collapsed on top of me and lay there for a moment, still inside me. Standing up again, I could hear him grope around for the duffle bag and then felt him slide out of me, instantly replaced by a butt plug. He untied my feet and picked my panties up off the floor, sliding them up my legs. He helped me stand up and pulled me to my feet. Picking up the chastity cage from where he had dropped it, he took my little sissy clit in his hand and quickly, expertly slid me back into chastity. It felt like home.

"Go wash up, get ready for bed" he told me as he spun me around to unlock my hands. I left, and as I wiped the makeup off and dried cum off my face and washed up I tried to remember if he had ever spent the night. I had at his place, but he had never stayed here. I was delighted that was where we seemed to be heading.

I finished up in the bathroom and took off my clothes, thinking I would head to my dresser and grab the shorts i usually slept in. Instead I exited the bathroom and found him lying on the bed, an elegant black satin slip dress with white lace at the edges lying next to him. I smiled at him and he sat up over the edge of the bed, picking up the sleepwear and helping me put it on. I turned a small circle to show him.

"Do we need to talk?" he asked.

"No Sir," I said.

"Think about it for a minute," he said. "It's OK if we do." He excused himself to get ready for bed, pulling a toothbrush out of the duffel bag. When he came back he asked me again.

"Genuinely, Sir, No. I've never felt more like a pathetic failure of a man, a complete sissy, than in that first moment. And I survived."

"Good girl," he said, and he hopped into bed. He pulled me in and settled me into little spoon, one arm under my head and the other draped over my hips, his fingers just grazing my chastity cage. He fell asleep instantly, but I tried to savor the moment as long as I could before finally drifting off.