A New Sissy's Inspection

[[Inspired by the Locked in Lace forum - specifically the 'Inspection' course]]

My first inspection.. I felt so powerless. Being the man I always felt so safe, aware that I had full control and that - even that time I played the submissive - I would always have the final say.

I came to the academy because my partner decided she liked me as the submissive, she wanted me to understand how it felt and had realized that she liked being the one in control. I didn't mind, being submissive was kind of fun and the feminization stuff got me excited long before she was involved - not that I'd ever admitted that openly to anyone. And as far as she told me this would just be like that, a little trip to explore my submissive side and become a better lover for her. I jumped at the offer, I would have been crazy not to.

When we reached the academy though, she told me she wasn't staying. She said that the nice girls here would take care of me. And to remember that everything they wanted me to learn here was for her. I told her I would do it for her but that I didn't want to cheat, I only wanted her. I thought she lit up at the time but maybe that smile was a muffled laugh. Because she was the one who sent me here. She knew everything.

The academy was much more extreme than I realized. I had to sign a contract, I thought it was just a little novelty to make me feel more submissive, so I signed it. My mind was elsewhere still unsure exactly what this place was.

I was put in this infernal chastity device, the constant pleasure making it impossible to think of anything but release. They removed all of my hair below my head, which they extended. They meticulously scrubbed at my body until it was softer than I knew possible, and gave me a full makeover. It was humiliating being pushed around and changed without any autonomy but I was okay until they started with the injections. I was tied down for those and I tried relentlessly to talk sense into them but all I got back was talk of the contract and condescending reassurances that 'It will all be okay, sweetie' or the like. So now I have plump feminine lips, breasts and a booty.

This was for my partner, it was all for her.. did she really know what was going on here? Did she want me to be a girl?

I had a choice of clothes at least, three uniforms to be exact. I chose the one they called 'school girl' which was somehow the least revealing of the choices. I had played with feminization before but only to the extent of trying on girly clothes and makeup but this, I looked.. and felt, like an actual girl I was genuinely attractive. This was the first time I had ever wanted myself in that way and with the chastity device constantly pleasuring me I wanted it badly.

After my transformation I was left with just a pen and paper, told to write a letter to my sponsor. I wasn't sure what a sponsor was and they told me in my case it would be my ex-girlfriend. EX-girlfriend. I was terrified. Alone. And writing to the person who before today I trusted most in the world. It wasn't an angry or accusatory letter, it was almost completely ordinary, the sort of thing I would have written in a long text if I still had my phone. But the overarching question was 'why are they calling you my EX-girlfriend?'

It wasn't until my first class on how to curtsey that I realized that 'The Academy' was a legitimate name they really did intend to teach me, and in my schoolgirl uniform, going to class felt weirdly normal. Until I actually got there and was punished for improper etiquette seconds into the class - immediately being put on display and spanked in front of a class full of beautiful girls. The embarrassment, pain, and pleasure were all too much to handle and left me bawling harder than I ever had since childhood.

After what felt like the longest day of my life they were finally letting me go to my room, not that I would have been able to sleep had they intended to let me. It turned out 'my room' and indeed my very small bed would be shared, it also turned out that every one of these beautiful students is in a very similar if not identical situation to me.

So, I shared my bed with a beautiful, stranger g̶i̶r̶l̶ sissy, as they insist we are called.

Me and my bed-mate had an obligatory thirty minute kissing session, not that we could have kept our hands off of each other the way our chastity devices were running on overdrive I was on fire and she was gorgeous and irresistible and it was becoming more and more obvious I wasn't going to feel any kind of release today but I stayed wrapped in her arms and hanging from her lips all night. It was both a passionate bliss of raw sexual tension and the most frustrated and denied I've felt in a lifetime but we couldn't stop for a second exploring every part of one another's body trying to get even an ounce of release from this encounter, but morning came first and we were sent to the showers and then went our separate ways to classes.

I felt awful, like I had cheated. I know she was only my ex now but the last time I spoke I told her I would never cheat and on that same night spent the night with someone else.

After that day I started to know what to expect and I did everything I could to stay out of trouble and do well in classes, perhaps they would let me out if I do everything right. Perhaps I could see my ex and find out why she sent me here.

It's only been a few days, they told me that I could be stopped and inspected at any time. I wasn't exactly sure what that meant, but I managed to avoid it until today. It was surreal, I'd never done anything with a man before - unless you count the sissies I sleep with each night.

Mr. Jones stopped me on my way to class and before I had fully understood what was happening he was already reminding me I was supposed to curtsey! I felt my heart jump up into my mouth and immediately followed orders. I pulled off a flawless curtsy, apparently the maid curtsy was appropriate so I followed orders again and he seemed pleased enough. I was so relieved that I hadn't seemed to have messed up yet. Mr. Jones was so much bigger than me, I always thought I was quite tall, even for a man, but he towered over me and his arms were practically the size of my torso. He made me feel like I would do absolutely anything to stay on his good side and that's what I intended to do. I greeted him as I had been taught to greet all adults by asking 'How may I make your day better?' and was prompted into my first inspection.

I twirled around like a ballerina for him before taking an inspection position with my hands behind my head.

He toyed with me readjusting my position.

Then he asked me to spread my legs. No man had ever asked that of me, why would they? I obeyed unquestioningly allowing him to stroke his finger under my skirt fully saturating his finger in my ever-flowing juices seeping from around my chastity device. He guided his finger towards my mouth and told me to taste myself I wrapped my lips all the way to the base of his finger making sure to suck every last drop of my juices from his big masculine finger - there was no room for error here no matter how shameful I had to be I wasn't taking another punishment - I let out an almost inaudible moan as the intoxicating taste filled my mouth. I tasted it with every sissy I had slept with over the past few nights and it was becoming addictive it was the taste I most associated with sex since becoming trapped in this device and I couldn't get enough.

I had accidently relaxed my position, he prompted me back to my inspection position and told me to cross my eyes and clear my mind which was easily done, this place had me aroused and thinking of nothing but sex since that first night. Since my transformation I had even caught myself thinking about men - how my new plump lips could wrap around a long veiny cock, how my pink lipstick would leave a line around the base of his cock as a sign of my achievement showing how much of his length I could take. I mean, I had become my ideal woman. How could I not think about being taken by a man? How it would feel to be pushed up against a wall, to be completely at his disposal obeying his every desire. I was lost dreaming of being fucked.

He must have liked how I looked daydreaming because he roused me by pinching my nipples which, since being locked up, have become my most sensitive parts. I let out a full breath of air with a loud quivering moan and almost dropped my arms from behind my head before remembering my place and weakly staying in position trying my very hardest not to disappoint the huge man in front of me.

He looked at me with desire, it was strange to be so closely looked at like this by a man outside of my dreams but it was flattering nonetheless. It would be a lie to say I didn't like looking sexy at this point. It was almost becoming a competition - I wanted to be more desirable than the other sissies, to be the object of everyone's desire. If I was going to do this I would do it well, I've always had a bit of a competitive streak. But when Mr. Jones told me to drop to my knees I think I would have resisted, I want to believe I would have resisted had I not felt so weak, so ready to collapse.

The words were still lingering on his lips as my knees sunk to the floor and I was left in front of a man staring towards an unbelievably large bulge in his pants it pressed out against the fabric coming down his inner thigh and beating with arousal. I was proud of what I had done. Genuine pride. I sat, staring at another mans erect cock wrestling with his pants with a feeling of pride because I made that happen. I was also terrified. Thinking about this stuff was one thing but actually committing to doing it? Was he really going to make me put it in my mouth? I was undeniably a man, with a girlfriend, less than a week ago and now I was here. I was absolutely undeniably more intimidated than I had ever felt in my life. Whatever this man wanted me to do I would do it. I knew that without any question in the matter and even if I tried to resist there was nothing I could do to stop him from helping himself. It wasn't even illegal everyone at this academy had been given written consent to have their way with me. But that didn't matter because in this moment I was his, I would have followed any order he gave.

So I sat, hands behind back with my arched back and my little tits pointing up at him staring directly towards his throbbing member beneath his pants and my mind goes blank - almost blank

Cock...

Cock..

Cock.

Cock, I have visions of sliding it out of his pants and teasing the tip before really showing off my abilities and thrusting it all the way down my little throat and gurgling on his precum. How I could lick all the way up his shaft and suck on his balls to bring him closer to the edge. I imagine the thick load of creamy cum dripping all over my beautifully made up face and I imagine the sweet and salty taste, I wonder how much better it would taste than my juices, how real cum would taste, from a real man.

Then he tells me to open my mouth. Suddenly this is real. I'm about to suck a cock in the middle of a hallway on my way to class. It looks even bigger outside of his pants, how do I fit THAT into my mouth? But there's no time to think, to falter, he wants me and I obey. I wrap my plump pink lips around the head of his cock and it practically fills my mouth, I struggle to keep my mouth open wide enough to stop my teeth from pressuring his shaft and experience the taste of his precum dripping directly on to my tongue as I swirl it around realizing how inexperienced I am but putting my all in to trying to get a reaction.

I hear a quiet moan as he tells me to suck, I did it! My concerns start to fade as I start sucking more enthusiastically bobbing my head up and down taking as much as I can without choking. Eventually his moans start to match the pace of my own gargled mewls of pain, fatigue, embarrassment, and pleasure. He pushes harder into my throat making me choke and struggle but I keep wrapping my tongue around his length and trying to perform as well as I can right until the end. I feel the warm smooth cream coating the walls of my throat and pushing all the way down to my core as he grunts words of encouragement. He makes sure I drink it all but I didn't intend to waste it anyway. This is so much better than the juices from me and my fellow sissies. This is better than anything I could have hoped for. I gulp and suck trying to get every last droplet of his cum from the monstrous shaft now slowly softening in front of me. I lick inside all of the curves ensuring there's nothing left before displaying my prize with an open mouth full of cum looking up into the eyes of my first true male sexual experience. He tells me to swallow and I close my mouth and swish the cum around with my tongue savoring the taste before letting it all slide down my throat in one smooth motion.

He praises me and tells me to get back to class, he even promised another inspection tomorrow. This experience made me late, I knew they were going to punish me.

As soon as I got to class my teacher scolded me and gave me a thorough spanking in front of the whole class. This seemed like a mild punishment compared to others I've experienced in the last few days but when I got back to the sissy dorms I saw myself in the mirror and realized how much my makeup had run. Everyone had to have known what I was up to, even those who didn't walk past it happening on their way to class.

That must be why the teacher went easy on me.