tagTransgender & CrossdressersProperty of Master Ajax Ch. 01

Property of Master Ajax Ch. 01

byTightandWhite©

I headed down to the community swimming pool glancing furtively left and right to make sure no-one was around. It was midnight on a Tuesday so there shouldn't be, but I wanted to be sure. I clutched my bag tightly as I reached the changing rooms. To the left, the lady's and to the right, the men's. After glancing over my shoulder one last time and taking a deep breath I went to the left, committing myself.

Ever since I had been young I had had a fetish for dressing up in girl's clothing. It started small, stealing a few items from my sister's draws when she wasn't in, but escalated to trying on dresses and even shoes. Eventually I started wearing little things under my normal clothes out in public. I had thought leaving home and going to university would give me more freedom to indulge in my habit, however living with 5 room mates in university dorms proved to be even more restrictive than living at home. Now it was the summer holidays and my parents were headed to India for two months to do some weird spiritual thing they had read about. With my sister having decided to take a gap year to travel across Europe I had the house to myself. My parents probably thought I would be inviting people over for parties the whole time, however I had very different ideas. With my sister's old wardrobe at my disposal I would finally be able to play out my desires.

I quickly stripped down and pushed my clothes into a corner. Reaching into my bag I first pulled out the towel and then reached in for the swimsuit I had chosen. It was a black spandex one piece with a full back and light foam padding at the breasts. I lifted it up to my face, feeling the material play between my fingers. My cock twitched; I had always had a thing for stretchy, nylon type materials. Smiling into the mirror I held the costume low, stepped into the leg holes and began to pull it up. It brushed against my thighs making my already semi hard cock fully erect. I began stroking it slowly but stopped myself. There would be plenty of time for that later. There was no way I would be able to tuck it away as I had meant to do, so instead I put it vertically against my stomach and brought the swimsuit up between my legs and up my back. After slipping my arms through the holes and tidying up the costume (especially around my bottom where it had bunched up between my cheeks) I stood straight and looked in the mirror. I gasped at what I saw. The skin tight black material hugged my hips and accentuated the small curves in my body so that they appeared extremely feminine while the pads on the front gave the impression of budding, teen-aged breasts. Turning to the side I saw how it plumped up my bottom and dove inwards between my legs. The only thing I was missing was long, luxurious hair cascading down my back. That and a way to hide my throbbing erection which was outlined perfectly against my stomach.

After peeking out the door of the changing room to check if the coast was clear I nimbly tiptoed out to the pool and into the water. Quickly submerging myself I swam out towards the deep end enjoying the freedom the costume provided. Hugging my skin it followed my every movement rather than constantly brushing back and forth against my legs like boy's swim shorts did. Each time I moved my arms I felt it flex against my nipples and I soon settled into doing laps of breast stroke.

After finishing my swim I headed back into the girl's changing room to shower, grabbing my towel as I went. Tossing the towel onto a bench I went pick up my clothes from the corner I had put them in but stopped dead in my tracks. My clothes, and my bag, had disappeared! I stood there, still for a moment, when I heard a creaking sound behind me. Someone else was coming in! Panicking I dashed into one of the toilet cubicles and slammed the door shut. 'Christ!', I thought, 'If a woman walks in on me here wearing nothing but a girl's one piece costume I'll be labelled a pervert for the rest of my life!'. I regretted dropping the towel on the bench, at least with that I could have covered myself and pretended that I had mistaken this for the men's.

"I know that you're in there." The deep voice echoed around the tiled room. "Why don't you just come out so I can see you, there's nothing to be embarrassed about."

My heart was throbbing in my chest. That was a man's voice! What was a man doing in here? And had he really seen me?

Knock knock! He knocked on the door my my cubicle. "Come on sweetie, come out now." Slowly he pushed open the door, revealing my an inch at a time. I stood there frozen in terror and shame. Before me stood a large man, around 6'2 with broad shoulders, wearing a business suit. His tie was undone and collar open, revealing the top of his chest. His steely eyes worked their way over me, taking their time to savour every detail. I shrunk away, ineffectively trying to cover myself with my arms. Seeing this he chuckled and beckoned me forwards.

"Come out here, I already had a good look at you as you were enjoying your swim." Drat! I thought I was alone! Seeing now other choice now I walked forwards, cringing as he put his thick arm around my shoulders and guiding me to the middle of the room in from of the mirror. I noticed he had put a sports bag on the bench. Not mine though, this one was white with a pink Playboy logo on it.

"So," he said, "you like to dress up as a little girl." It was a statement not a question yet his eyes still seemed to be searching me for an answer. I lowered my head and looked at the floor.

"Does anyone else know?" he asked.

"N-no", I stammered. "P-please don't t-tell anyone, p-please, I won't d-do it again I s-swear."

He looked at me intently and said "Well, we'll have to see about that. Go over there and empty your bag."

My bag was nowhere to be seen. The only bag in the room was the white and pink one on the bench so he must be talking about that. I stepped over to it and began to unzip it, painfully aware that he had a perfect view of my spandex covered bum as a reached forward. I opened it up to find a small dress. My sister used to watch Sailor Moon when she was younger and I realised this was a dress based on the main character. The top was white with short puffed sleeves barely going over the shoulders. A blue collar in the style of a Japanese school dress wrapped the neck and a large red bow hung from the front of the collar. The pleated skirt which looked like it would barely get to the mid thigh was blue to match the collar. I laid it out on the bench and emptied out the remaining things: a pair of white over the knee socks and red 5" heels, a blonde wig and hair band, a red collar, a bottle of hair removal cream, two jelly-like breast forms, matching white panties and bra, and a strange plastic device I didn't recognise.

As I turned back around to face the mysterious man who had caught me at my most vulnerable there was a snap and a flash. He had taken a photo of me!

"H-hey! You need to delete that I can't have anyone seeing me like this!"

"Do exactly as I say and no-one will ever have to see this, or the others I took of you in the pool. Now, take off that costume and get in the shower."

"What do you want from me? I don't have very much money I'm a student"

"Money? Do I look like I need more money? No. We're going to go back to my house where I will explain your future. For that you have to be appropriately dressed. Now get in the shower"

"Where are my clothes? Give them back I'm not going to dress in this stuff! I'm a boy!"

Casually he started pressing buttons on his phone. "Ah yes here we are, Mr and Mrs Foxworth, picture message. Are you sure you want me to send this?" he asked.

"No! Don't please don't. OK I'll do it as long as you promise not to send that to anyone!" I pleaded.

"Take off that costume, get in the shower, then cover your body with the hair removal cream. I want you nice and smooth."

Defeated I began to strip off the bathing costume, peeling it off and standing naked before him. After washing off all the chlorine from my swim applied the hair removal cream. After waiting the prescribed time I washed it off again, leaving my skin silky smooth. I couldn't help but run my hands over my skin enjoying the sensation until I noticed him looking at me again and stopped abruptly. I didn't even know his name.

"What's your name, and who are you?" I asked.

"My name is Master, or Sir if you prefer, and I am you new master", he replied. "Come."

He handed me my towel to dry myself and then stepped forward with the strange plastic device I had taken out of the bag earlier.

"What is that thing?" I asked nervously.

"Something to remind you of your place" he chuckled.

Kneeling down he reached for my penis with one hand. I stepped back, pushing his hand away. "No!" I exclaimed, "What are you doing!?"

"Step forward and move your hands away", he commanded.

"N-no", I squeaked backing further away.

In two strides he reached me roughly grabbing me by the arm and dragging me over to the bench. "Don't you dare defy me sissy!" he roared.

I cried out as he sat down on the bench and pulled me down across his knee leaving my freshly shave bum totally exposed.

"I see I'm going to have to instil some discipline in you!"

His hand came down swiftly and the sound of the slap echoed around the room, only to be drowned out by my sharp yelp. Smack! Smack! Smack! He spanked me aggressively, each stroke coming down in exactly the same place on my bare bottom. I squealed and struggled but was helpless under his iron grip. Smack! Smack! Smack!

Then it was over. The spanking stopped. He drew several deep breaths and my squealing reduced into sobbing. Tears were running down my cheeks and my rear was burning.

"Now, are you going to be a good little girl and do what you are told?"

I sobbed incoherently.

Seeing him raise his hand again I spluttered "P-please don't, I'll do what I'm told, p-please!"

"Please, what?"

I hesitated for a moment, then sobbed "Please, Sir, I'll do what I'm told."

"Good." He lifted me to my feet and then picked up the plastic device that he had dropped on the floor. Holding me firmly he took hold of my penis and put the device around it. I heard the click of a lock and he straightened up. Feeling down there with my hands I could tell that my manhood was completely trapped, reduced to a small bump on my smooth skin.

Master gestured over to the panties, bra and breast forms. "Those first."

Not daring to disobey I slipped my feet into the white cotton panties, brought them up my legs and over my still smarting rear. With my cock and balls locked away they fitted very snugly. As I stood up I saw him spraying something onto the backs of the breast forms. He brought them over to me and pressed them against my chest. It must be some kind of adhesive, I thought. I stood there wordlessly until he removed his hands, leaving the breasts in place. I could feel their weight on my chest as I picked up the bra, slipped it over my shoulders and fastened it behind me. I wish I could say that I was familiar with it from all the girls I'd been with, but in truth it was from playing with my sister's bras.

"Very good", he said as he picked up the dress and lifted it over my head. I slipped my arms into the sleeves and he lowered the dress over me, pulling it down around my body until it fitted properly. He got down on his knees with the rolled up socks so I could put my dainty feet into them. I put a hand on his shoulder for support and could feel his muscles move as he unrolled them up my legs. They finished just over my knees leaving a gap between them and the skirt which only cover half my thigh. His fingers stroked my bare thighs for a moment before he reached over and picked up the blonde wig.

"In front of the mirror", he ordered. I meekly complied. He quickly fastened the wig on top of my head completely covering my short hair and giving me beautiful tresses which spilled down my back. While I was admiring how my new hair looked he had retrieved a make-up box and nail polish from a side pocket of the bag. Swiftly and silently he applied the make-up to my face, first concealer, foundation and highlighter, then a little blush on my cheeks. He then carefully applied eye shadow and eye liner to my eyes, finishing them off with a small amount of mascara. I was shocked at how much my face a changed in such a short period of time. He completed the picture with a dash of red lipstick.

"You'll have to learn how to do that yourself, Grace will teach you. Now hold out your fingers."

Somewhat dazed I held them out and he applied a coat of red nail polish. I gazed at the reflection in the mirror. I had been totally transformed! The knee socks drew the eyes up over my sheer legs towards my thighs which were covered with just enough skirt to be tantalising. The dress hugged my body in at the waist and out at my breasts giving me a very feminine figure. I could see my chest moving in and out slightly as I breathed. My blonde locks spilled down over my shoulders and back, the red hair band keeping it in place. My face had always been somewhat oval and feminine, but the skilled application of make-up made me look unbelievable! Master set down the red heels in front of me and I stepped into them without question leaning on his shoulder again as I did so. He showed me the red collar he was holding, grinning as he did so. On the front was a small metal tag which read "Property of Master Ajax". At the back was a small but strong looking lock and a D shaped ring. He put it around my neck, tightened it and fastened the lock. I gulped, shocked at what was happening to me.

"You're mine now, do you understand? I am your Master and you are my little Sissy girl", he said.

"But I'm not a girl, I'm a boy", I pointed out.

"Really?" he said, smiling. "Don't boys have dicks? Show me yours."

I lifted up my skirt, showing him the small plastic encased bump that was my penis.

"I don't see a dick, all I see is a little sissy clitty. What do you see?"

Dejectedly I mumbled, "A little sissy clitty."

"A little sissy clitty, what?"

"A little sissy clitty, sir"

He stepped closer to me, making me even more uncomfortable. "And what are you?"

Lowering my head in submission, I admitted, "I'm you're little Sissy girl, sir."

"Good, good. Now get down on your knees. Put your towel on the floor so your socks don't get dirty", he commanded.

"W-what? Sir? Why?" I spluttered.

"Do I need to discipline you again?" he thundered.

"N-no, no sir!" The memory of what had happened last time I had questioned him was still painfully fresh in my mind, and on my bum too.

Once I was kneeling on the floor he began unbuckling his belt. "You see, this is what real men have down there instead of sissy clitties like you've got." He dropped his trousers and boxers to his ankles letting his large penis flop out before me. He too was shaved, but that only served to make him look even more masculine as it showed every detail of his manhood. It was rapidly getting hard, expanding as it did so. I gasped. "Yeah you'd better get used to having your mouth open like that", he laughed.

"What are you doing!?" I exclaimed. In truth I already knew having seen enough porn to know what was going to happen next, but I couldn't believe it was happening to me.

"What do Sissies do when presented with a real man's cock?" he asked.

"Umm... Umm... I don't know..." I mumbled.

"You do know, slut. Hold it in your hands."

Gingerly I reached out and grasped it in my petite manicured hands. It was a whopping 8 inches long so I needed both to hold it. He was uncircumcised so his foreskin rolled back to reveal the bulbous head. I was entranced. I held it up in front of my face unable to take my eyes off it. It's impressive girth was laced with popping veins. I could tell that he was really turned on.

"Now lick it."

I was unable to stop myself. I did it without question, extending my tongue from my red lipped mouth and licking the head of his enormous member. It spasmed slightly and he let out a small groan. I continued, licking around the head and the down the side of the shaft. Feeling the heat of it radiating onto my beautiful face I picked up the pace, licking back and forth and round and round on the head. He placed a firm hand on top of my head and guided his meat towards my waiting mouth.

"Look up at me", he ordered.

I turned my eyes up to look at him. I knew what this must look like for him. I'd cum myself many times to just this look in porn films. The hulking man standing erect, the girl on her knees in submission. Her eyes upturned begging him for his cock, the look of absolute pleasure as she received it and got to work.

I gazed up at him. This was it I guess, I really was about to become his Sissy girl. Gently, almost tenderly he pulled my head forward, pushing his penis between my lips. I opened my mouth to take him. The head was very warm and covered in pre-cum and saliva. I had to open my mouth as wide as I could to accommodate his impressive size. He groaned again, louder this time, and pushed his cock further and further in. It reached the back of my throat and I choked, trying to push him back. His held my head firmly however and I was unable to move him back.

"mmMMMhhhMM ... hhHHhhhMMM ... mmMMhhhhhhhMMmm!" I tried to cry out but all that escaped my cock filled mouth was a series of pathetic muffled moans.

"Take it Sissy, take it all", he moaned back and pushed his monstrous member deeper into my throat.

"MMMMMMMMMMMMMMMMMmmmmHHHHHH HHHhhhMMMMMMMMMMMMM!! HHHHHHmmmhhhMMMMMMMMMMM!!" I was gagging and could barely breathe!

"Ohhh I had forgotten how cute new girls are on their first time. You're going to swallow every inch of my cock, Sissy, so listen carefully. Lean forward and lift up your back a bit, arching it, to open up your throat. Try to relax you muscles. Your first few times will be hard but you'll get used to it. You'll be getting a lot of practice."

He pulled back a little allowing me space to breathe. I began licking and sucking his head in an attempt to buy more time. He moaned erotically and I swirled my tongue around and around, sucking it with my glossy lips. I felt the pressure again as he moved my head closer. I tried desperately to push him away, but even with both hands I was no match for his strength.

"HHHHHHHHHHHHHHHHHhhhhhhMMMMM MMMMMMMMmmmHHHHHH!!" I gagged again.

"Relax yourself!" He again drew himself back out but only for a moment before thrusting in again. This time I felt him go further before I gagged. Saliva and pre-cum dribbled out of my mouth onto the floor. He kept going, pulling out just a little then going in again, one inch back two inches forward. I choked and spluttered on his enormous cock and tried to relax. Soon I could feel his head opening up my throat so I had to take breaths in short bursts between thrusts.

"Yes that's it", he moaned and began thrusting faster. My face was getting close to his body now and I could now longer look up at him. My vision was filled with his ripped stomach until eventually I had taken all of him. He now had both hands on my head, moaning and groaning as he face fucked me. I was so concentrated on stopping myself from gagging I don't know how long he abused me like that. Eventually though his thrusts sped up and he let out a cry. His hands and his cock tensed as his semen spurted into the back of my throat. I choked on the musky taste coughing it up, but he again pushed his penis deeper into my throat. My whole mouth was filled with cock and semen. He held my face buried in his crotch preventing me from breathing. I choked and grabbed at him trying to cry out.

"Swallow it Sissy, swallow it all!"

I obeyed swallowing his seed, swallowing and swallowing. There was so much of it I felt it running down the sides of my mouth onto the floor. When he had finished ejaculating he withdrew his penis and let go of me. I dropped down gasping for breath, more semen and saliva running down my chin.

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byTightandWhite© 16 comments/ 39472 views/ 48 favorites

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