Full Scholarship

"Mr Hurwitz, I brought a second lot of boxes up. Thought I'd save you a journey. I can't leave them here though."

I was fighting with the clasps on the heels. They were too tight! I couldn't get them undone fast enough. I scrabbled around for something to cover myself with. In a panic, I grabbed one of the floral Kimonos and pulled it on. Taking a deep breath, I opened the door a crack.

"Hi Adrian, just leave them th..."

However, Adrian had taken the opening door as a as a sign to come in, and pushed passed me with an armful of parcels. I stumbled backwards and collapsed onto the sofa. He set down the boxes in the centre of the room, and stood back up slowly. He was looking in the direction of the bed. He turned to me confused, as if about to ask why my bedsheets were piled high with girls clothes.

"Am I in the wrong ro..." Adrian stopped mid sentence, and then snorted in laughter & surprise.

I pulled the kimono tight around myself. As that could possibly hide my shame!

"Nice outfit." Adrian had a dangerous look in his eye, but extended a hand out to pull me to my feet. Hesitantly, I took it.

"I'm sorry, this isn't a great time..." I couldn't look him in the eye. I was almost paralyzed with embarrassment.

"Looks like perfect timing to me."

He pulled me to my feet. Still unsteady, I wobbled towards him. He reached out and steadied me, his hands on the bare flesh of my hip. He took a step forward and suddenly our bodies were pressed together.

"I.. I'm not gay" I managed to stutter.

"Neither am I".

I could feel a bulge in his trousers against my stockinged leg, and fear rose up inside me. I tried to push away but his big arms held me tight.

"This... this isn't what it looks like. I.. I can...".

Adrian cut me off.

"They said every little white boy has a girl inside trying to get out, but I never really believed it."

"I am a boy!"

"Really?"

He turned us to face the mirror. His eyes were looking me up and down, drinking me in. I was a slim sissy slut pressed up against his dark, muscular, fully dressed body. Adrian slipped his phone out of his pocket and took a photo of us before I could react. I redoubled my efforts to escape and tried to grab the phone.

"I'll call the police!" I threatened.

Adrian was holding both my wrists tightly behind my back with one large hand. He laughed. "And say what? You opened the door dressed like this. You knew it was me outside. That sends a man a certain kind of message."

"It wasn't intentional! I don't want this. Please delete that picture."

"Your little dicklet down here suggests otherwise." He pulled roughly my panties down to my ankles to expose my stiff penis, and I stepped out of them before they could trip me up. "This thing is tiny. Girl, you were born to be a woman."

I started to tear up, but somehow the humiliation made me harder.

"Little blond sluts have walked past me for years now, making eyes at me, smiling, teasing me. Giving me a show in those tight jeans and short skirts." Adrian growled in my ear. He spanked me once, hard on the ass. "Isn't this what all you girls want? A big man to come and take care of you?"

I shook my head frantically, and when I opened my mouth to object, he stuffed the panties in.

"mmmmmm! mmm." I moaned through the gag.

He laughed at my helplessness.

"Ok, I'll cut you a deal. I'll leave, and I'll delete the photo."

I exhaled, visibly relaxed.

"If you let me cum on that pretty face of yours."

My eyes went wide. But I stayed silent.

"If I you blue-ball me, I'm afraid of where this photo might end up... might somehow get printed & left all over the dorms..."

Slowly, resigned to my fate, I nodded.

Adrian released me, and I sank to my knees, looking up at him. He unbuckled his belt, and released his throbbing cock. It was large, maybe 7 inches long, and much thicker than mine. So girthy. He held it above me, and slowly rested it against my face.

"What a sight. No real man would have agreed to this" said Adrian.

Adrian began jerking his big cock directly in front of my face. I could tell that the power trip he was on had him riled up, and that I wouldn't have to endure this for long.

"Jesus you're such a dirty little slut. Red lingerie, high heels. Man, I'd love to fuck that little sissy hole of yours."

He gave me a gentle slap. My cock jerked. I didn't realise I was still so hard. Was I enjoying this!?

"Such a sissy girly whore."

He put his hand under my chin and forced me to look up at him, wide eyed. He was taking his final strokes.

"You ready for this load you little slut?"

I nodded, and closed my eyes, expectantly. Quick as a flash, Adrian whipped the panties out of my mouth, and replaced them with the head of his cock. I squealed in surprise, and tried to push him away but he held me tight, forcing his cock to the back of my throat. Immediately, he started pumping cum into my mouth. I was gagging and choking, but some of it I couldn't help but swallow. He pulled out and spurted the last heavy ropes of cum over my face.

Released, I rolled backwards onto the carpet. I lay there, head-spinning, legs akimbo, a mixture of cum and spit running over my cheeks. Adrian shook the last drops of cum from his cockhead over my prone body, zipped his fat cock back in his pants and then took out his phone. I thought he was going to take further photos with which to blackmail me - I must have looked like a used little doll drunk on cum - but he was simply showed me the screen as he deleted the incriminating photograph.

"T-thank you" I managed, and propped myself up on my elbows.

"Any time" Adrian said. I watched as he turned and left, closing the door behind him.

Gradually, I regained my composure, and pulled myself up onto the sofa. I freed my feet from the vertiginous heels and placed them flat on solid ground. I took a few deep breaths and, on autopilot, licked my lips. I regretted it; the sour taste of his drying semen on my face brought with it a wave of shame.

"What the fuck am I doing." I said quietly to myself. I had just had a dick forced into my mouth and hadn't even had the first session with Arthur yet.

I washed my face in the bathroom basin, and stripped off. The stained lingerie went into the laundry hamper, and I pulled on my jeans and a t-shirt, keen to feel manly again; easier said than done with freshly shaved legs and the aftertaste of cum in your mouth. Mechanically, I categorized the outfits that Arthur had bought me and stashed them into my wardrobe. The newest set of packages I left unopened, and pushed them under my bed.

Then I went grocery shopping.

I blushed deep red when passing Adrian in the lobby.

*

Evening approached quickly.

Whilst I wasn't exactly looking forward to our meeting, I was determined to keep the gig, and that meant making sure Arthur got his moneys worth.

The French maid outfit was straight out of a party slut's Halloween wardrobe, and every guy's favourite fantasy. The dress was so short it barely covered the white lace thong that ran between my pert cheeks. Long white socks, complete with frilly cuffs encased my legs up to my thighs, and a frilly headband, and lace gloves and choker completed the look.

I placed a pair of tall black Louboutin's next to my chair in case I'd be required to wear them, and took some time to apply some light make-up. This time I used a YouTube tutorial to properly contour my face and highlight my cheekbones. I wanted a fresh faced look, and so held back on the heavy eyeliner. Just some mascara and some lip gloss. I couldn't believe it was me in the mirror... perhaps there was some truth to Adrian's comments. There was something captivating about the girl version of myself. I shook my head to clear the thoughts, and moved back to my laptop. I had it positioned so the webcam looked out over my bed. There I curled up and waited for Arthur's call.

I didn't have to wait long.

"Hi there" Arthur's voice filled my dorm room.

"H-hi" I responded nervously.

"Wow, you look amazing! You've really done a fantastic job with the make-up. I'm very impressed!"

Arthur's voice was animated and kind. It immediately put me at ease. I beamed at his compliments. He continued: "and that outfit... You're one hot piece of ass. I can barely believe you're a guy."

I blushed, a bizarre mixture of pride and shame.

"Thanks, I guess?"

"You've really nothing to be ashamed of. So what, you've got a slim build and a girly ass. This is your chance to make the most of it." Arthur's positivity was infectious.

"Ok," I replied steeling myself.

"That's my girl. Give me a twirl? I want to see the full ensemble. "

"Sure!"

I bounced up and spun around for him a couple of times. I was quite glad that Arthur didn't want to have any strange, awkward small talk. He was clearly keen to get down to business.

"I think I can see a bulge in those panties. This getting you excited?" Said Arthur.

Embarrassed, I gave a small nod.

"I don't blame you. I know what you're seeing in the mirror, and its fucking hot. A sexy French maid that you get to touch and play with. And everything she feels, you feel. Not many guys get to appreciate just how intoxicating it can really be to give into their desires and play the submissive woman."

A flash of concern entered my mind, but Arthur interrupted my train of thought:

"Take off the panties" he ordered.

I complied, and slowly slid them down my smooth thighs.

"Now put on the heels behind you."

I slipped the black Louboutin's onto my stockinged feet and tottered slightly upon straightening up. I was having trouble hiding my stiffening cock under the skimpy maids apron.

"Ok, now we're going to do a cat walk. Can you position the camera so I can see you walk around?" Asked Arthur.

Arthur had me sashay up and down the length of my studio apartment until I was was swinging my hips like a real slut. Occasionally he would ask me to bend over and spank my ass, or crawl towards the camera on all fours. Eventually, when he felt like I was totally in character, he let me sit back down.

"and what did you think about the toys?" Arthur asked.

"Toys?" I was puzzled. "Wait, that might be the boxes I haven't opened yet." I jumped up and grabbed the boxes from under the bed. It turned me on knowing my ass was pointed straight down the camera. Sitting back down, I put the largest of them on my lap. It was heavy compared to the clothes parcels.

"Go ahead. Open it up."

I ripped of the tape and opened the box. I removed the protective plastic stuffing, and uncovered a sizable collection of dildos. My stomach dropped. Arthur must have seen the alarm written across my face.

"Show me what you've found" he said.

I lifted up the largest of the dildos. It must have been over 9 inches long, with big heavy balls and a bulbous head. The shaft was detailed and veiny. It has a soft, almost skin-like texture.

Arthur laughed. "Does that frighten you?"

"What do you expect me to do with this?" I asked in disbelief.

"There should be smaller ones in the box. Grab one of those."

I picked out a 5inch smooth blue dong. Much less threatening.

"We can start you off with this one." said Arthur.

"You didn't say I'd have to put things in my ass!" I whined. "This wasn't part of the arrangement."

"Think of it as a constantly evolving relationship. I promised to introduce you to knew things. You'll love it, I promise."

"I doubt it. I'm not gay."

"You're a good little girl. And you're going to do as daddy tells you. Otherwise he's going to stop paying your bills." There was a hard edge to his voice now.

I gave him a sour look.

"Great. Glad I managed to talk you round. Now lube that up." Instructed Arthur.

Reluctantly, I squirted some lube into my hand and started rubbing the dildo as if it was my own, jacking it up and down.

"Oh yeah, that's it babygirl, get that dick hard." Arthur's approval came from my speakers. I blushed at his dirty words.

With Arthur's encouragement, I started masturbating my own dick as well as the plastic blue one. I lay back on my bed, and propped myself up facing the camera, like I had seen camgirls do online, legs spread so Arthur could get a good view of my smooth hole. I kept a hand jacking the dildo, and rubbed lube into my tight asshole. It opened to accept a finger easily enough. After a while I could get a second digit in.

"That's it. Keep stretching yourself out. You'll know when it's ready." Came Arthur's encouragement. His breathing was laboured, and I could tell he must be masturbating to me.

After a few minutes and some more lube, I was finger-fucking myself.

"This feels really good." I moaned, surprised.

I lined the head of the dildo up with my asshole. It was slick with lube, but I could feel the stretch as I pushed it in. The head opened me up and popped in, and it penetrated me a few inches, pressing against my prostate.

"Fuck!" I groaned. This was dangerously good, and Arthur could see that.

"Let me see you bounce on that cock you slut" said Arthur.

I reddened in shame at his dirty words, but climbed up on my knees.

"I want to see you side-on"

I turned so Arthur could watch me in profile. Now the dildo was below me, the tip still inside me. I positioned a cushion below the dildo to raise it slightly, and started bouncing.

"Now we're talking" said Arthur

The pressure on my prostate never let up. The constant ribbing as the dildo fucked me was bringing stars to my eyes. My weight was on my hands and I was almost twerking on it, taking its full length each time. I made sure to lift my dress and apron so Arthur could appreciate my slim waist and the dildo sliding in and out of my hole. I was lost in the moment and the sensations, just a horny girl fucking a pillow on camera.

"Fuck, it's so good." I moaned like I had seen the girls in porn do. "I love it deep."

I put a finger in my mouth and posed for the camera arching my back and moaning enthusiastically. I heard Arthur cumming on the end of the line.

"Fuck yeahhhhh...You're such a good little dirty girl. Jack yourself off, I want to see you cum too."

Whilst riding the dick, I frantically rubbed my the head of my dick as if it were a clit. That was enough to set me off, and I came hard. My orgasm was so intense that I collapsed on the bed, my asshole spasming around the blue dildo as I drenched the bedsheets in cum.

Once my legs had stopped shaking, I shifted to the edge of the bed. My asshole was now incredibly tight around the dildo, and I was scared to pull it out. Groaning in guilty pleasure, I pushed it in up to the hilt so that it was completely inside me except for the flared base. Quickly, I pulled my thong back on, and swung my legs over the side of the bed.

I looked into the camera in disbelief.

"I think...I think that was the best orgasm I've ever had. I never would have known ass-play could be so good" I said, disbelievingly.

"Not bad my end either. I appreciate your hard work" said Arthur.

"I guess I've had worse jobs." I replied. I took a few deep breaths, and my level headedness started to return.

"We all have to make a living." Laughed Arthur. "Ok so do you want to know about the bonus scheme?"

"Sure?"

I was nervous at the mention of this, but my head was swimming in the afterglow of my orgasm. What was another new experience after today?

"Look inside the toy box. There should be a chastity cage inside" said Arthur.

I rummaged around, and found the hard plastic contraption in protective wrapping at the bottom. I held it up to the camera. It was intimidating. A small hard plastic cage.

"Is this it?"

"Yes. Every day you wear it, you earn an additional $50."

Wow. That was nothing to sniff at... But it looked like a tight fit. Even with my tiny dick I wondered if it would be possible to even get it on.

"Does it hurt?" I asked.

"No, I ordered you a top of the range model. It's designed for long term use, and easy to clean. The reviews were excellent. But you won't be able to masturbate. Not in the normal way you're used to. That's the real sacrifice."

"Ok, I'll think about it."

"No problem. Go grab a shower and I'll see you tomorrow. Thanks for the show."

Arthur signed off, leaving me alone.

I stood up and padded into the next room to get a glass of water, still dressed in my white knee socks and sissy maid outfit. The blue dildo was still firmly inside my butt, and I felt it shift with each step. I passed my mirror and again was surprised at just how hot I was; a fit pixie blonde girl flushed red red with sexual excitement. I could feel the urge to masturbate returning.

Curious about my newfound prostate sensitivity, I revisited the toy box and found a dildo in the next size up. This one was slightly more realistic, and longer and fatter. It also had a suction cup base. I stuck it to the bed frame, where it swayed comically.

This time, I removed the black and white dress, but re-tied the pinafore apron around my waist, like the worlds sluttiest waitress. I got down on all fours. I tugged out the resident blue dildo from my grippy ass, and tentatively backed up against the bigger dildo, the cool head pressing against my aching rosebud. Slowly, I began started stretching myself out. I struggled to take the extra girth, and gasped when the head made it past my sphincter. It felt amazing to be full again, and I slowly worked it in until I found that sweet spot where my prostate was, and could be repeatedly rammed. This time, I rode it with a real urgency, desperate for the high of an orgasm. My hand was a blur as I frantically worked my cock.

When my orgasm came, it hit me like a freight train; again I slumped to a shivering wreck on the bedroom floor, the dildo slowly sliding out of my gaping ass.

The haze of my second orgasm began to clear, and I picked myself up. A thought crossed my mind: maybe being locked in chastity and unable to masturbate would be a good thing? I could see myself wasting a lot of time experimenting with these dildos otherwise. Chastity could be good for my studies, keeping me focused etc. Its not like I had much luck with women, so I wouldn't be missing out there.

I showered for the third time that day, and once towelled off, I carefully locked my shrinking package into the plastic cage and clicked the small pink padlock into place. It was pretty comfortable. If I found I didn't like it, I could always unlock it, I told myself.

I took a full length photo showing off my cage to let Arthur know I had entered the bonus scheme. It was only after sending it that I realized I was still in my heels and thigh socks, with my lace maid gloves and headband in place. I pouted at the mirror. I looked every inch the sissy. The response from Arthur came immediately:

"Extra 100 bucks if you wear the some lingerie under your clothes tomorrow. Photograph yourself in a public washroom."

Easiest money I had ever made.

"Deal" I wrote back.

*

When I woke the next morning, my normal morning wood was tightly restrained by the plastic cage. I lay back in bed and tried to think about other things to take my mind off the uncomfortable pressure, but it made no difference. My mind felt prickly and hazy as memories of the last night's cam session swam though my head. The sheets were so soft against my smooth skin, and was reminding me of the thigh socks I had slid down my legs before climbing into bed... Goddamn it Eric, focus!

I made breakfast, and had a coffee. I was feeling better, but I was incredibly conscious of my trapped little cock the whole time. I had thought that the chastity would remove these feelings, but instead, it seemed to be amplifying them. All I wanted to do was cum, but I couldn't.

I took a cold shower and changed. Instead of pulling on boys underwear like I might do usually, I laid out a set of cute Calvin Klein white underwear. It wasn't too feminine, and the bra straps were wide & flat, which would minimize the chances of anyone seeing them though my clothes. The quality was great, and it cupped my small cock perfectly. I couldn't believe Arthur had bought all of this for me. I straightened up and posed in front of the mirror. Again, I looked almost unbearably hot. The white looked clean against my pale skin, and the sporty bra suited my flat chest. My breathing was fast, and I could swear it was possible to see my heart beating hard between my narrow shoulders. My cock was crying out for attention, as stiff as it could get within the confines of the cage, tucked into the pristine panties.