Tight Grey Shorts
My name is Tony, I'm 21 years old, and I'm a houseboy. Before I came to work here, I was, to put it mildly, a bit down on my luck. I had no money, no job and was about to be evicted from my London flat. I had no escape route.
At least, not until I saw an advert in the back of the Gay Times, under the heading "Jobs Offered". The ad ran:
Wanted: Houseboy for domestic service. Busy City exec, 45, seeks man, 18-40 to keep house. Reasonable pay, accommodation, food and clothing supplied. Box ------.
This was the answer to my problems - housing, money, job solved all in one. I contacted the advertiser through the magazine, and we spoke on the phone, arranging an interview for 5pm the next day. His voice was warm and sounded friendly enough, I agreed. After all, there was nothing to be suspicious about; this was a busy City gent who needed help around the house, that was all.
Well I arrived at his (expensive) apartment the next day, perfectly on time. I'd managed to dig out a shirt and tie for the interview from my scant wardrobe; appearances matter, especially in these things. I buzzed at the front door and waited until I heard the same voice over the intercom as I had heard on the phone.
"Hello?"
"Um hello, sir, I'm here for the interview . . ."
"Yes of course," answered the voice. "Flat four. Do come up."
There was a buzzing sound and the front door unlocked. I opened it and went up the stairs until I found the flat, admiring the decor in the hall. This place must be expensive, I thought, looking at the plush carpets, tasteful furnishings and graceful mini-chandelier. And this was just the hallway. I knocked quietly on the door of his flat, feeling somewhat intimidated by the luxury of my environment. Was I - a poor post-graduate, on the brink of eviction - going to be the sort of person he was looking for.
The door opened, and I saw the rather stern face of my potential employer. He was wearing an expensive looking three piece suit, well-cut from a quality dark grey chalkstripe material. His face softened a little, and a small smile flashed across his face as he saw me. "Do come in," he said. His voice was undeniably upper-class, but in the way of the well-pronounced and educated, not because he had any pretentious airs. He introduced himself as Mr Braithwaite, and invited me inside.
"Sit down," said Mr Braithwaite, in a tone that wasn't exactly an order, but gave the impression that I should obey it anyway. He poured us both a cup of tea - Earl Grey, naturally - and we proceeded to discuss the job.
"I have my CV, if you want to see it," I said, proffering the document.
Mr Braithwaite raised his hand. "I don't think that will be necessary. All I need you to do is to look after my flat here while I am at work and on business trips. Fortunately, I am not away too much, but I am always busy and seldom have time to do all the things such as dusting, tidying." I mentioned that he seemed to have done a pretty good job.
He smiled. "I've managed so far, I do like to be independent. But I have a few special projects coming up and even when I am at home I will be working a lot of the time." "What exactly do you need me to do, sir?" I asked, the "sir" landing naturally at the end of the sentence. Mr Braithwaite was certainly someone that I felt I should "sir"; his features, while stern, were handsome and warm, his demeanour was charming and his clothes impeccable. He seemed to demand respect.
"Well, I expect the place to be kept clean and tidy, I have a rota referring to which rooms should be taken care of on which days, you will be expected to collect my regular groceries order, do my laundry, and generally be around in case I need you," said Mr Braithwaite.
"Like a cross between a valet and a housekeeper," I suggested.
"Hmm. In uniform, of course. I don't need your CV, but I will be needing your measurements so I can get you one."
I thought it a little strange that there would be such a requirement, but I could see no reason to object, so when Mr Braithwaite produced a tape measure I stood up as he measured my chest, leg, collar, and curiously, my head. I put it out of my mind; my working conditions were, after all, exemplary. If I was going to fit into this place, I'd have to smarten up! We chatted for a while, about nothing in particular, I suppose he was just trying to find out about me, my interests and my personality; and whether or not I was trustworthy. We finished our tea, discussed pay and other arrangements, and Mr Braithwaite told me I had the job, if I wanted it. I said yes, and asked when he wanted me to start.
"Can you begin tomorrow?" he asked.
"Yes, sir, I can," I said. All of the stuff I had in my flat that I would need I could probably fit into two suitcases, and I was due to be evicted at the end of the week so there was not a great deal to arrange. We stood up, shook hands, and I left, happy to have solved my problems.
The next day, I arrived at Mr Braithwaite's apartment at 4pm prompt as requested. I had all of my belongings with me in two suitcases, plus a rucksack. The furniture in my old flat belonged to my landlord so I couldn't bring any of it with me, and it would have looked very out of place in Mr Braithwaite's place. My TV was rented, and since Mr Braithwaite had an excellent home entertainment system I didn't need that either. Plus I had the feeling I was going to be very busy. Mr Braithwaite's stern handsome features greeted me at the door. Courteously, he took my cases from me and put them in a room off the hallway.
"We can deal with your bags later," he said, ushering me along the corridor. He opened a door and led me into a medium sized room, minimally furnished with a bed, a chest of drawers, some bookshelves and a wardrobe with a full length mirror in the doors. "Right now we have some matters to attend to." He indicated the bed.
On the bed was my uniform. It consisted of a grey blazer, grey shorts, a grey shirt, a red and green striped tie, grey socks, a grey cap and brown shoes, all my size. The socks and cap had a red and green trim. I stared at the items on the bed, then at Mr Braithwaite.
"I've been good to you, boy, and I hope you appreciate it," he said. "This is your uniform, which I referred to, and you will wear it while in my service here. I will be in my study, where you had the interview yesterday. Please don't be long, I do not like to be kept waiting." And with that, Mr Braithwaite left the room.
I stared again at the uniform, with a strange feeling in my stomach. It was very similar to my old school uniform, and made me think back to when I used to have to wear items like those. I had a sense of trepidation, and just stood there for a while, thinking about what I had got myself into. Then I thought of the money, the flat, the job, and the security. Plus, as Mr Braithwaite had said, he had been good to me, taking me in. I should do as he said. I gulped and tried to suppress the butterflies in my stomach. How humiliating to have to wear this uniform! I am an adult! I also tried, unsuccessfully, to suppress the perverse stirring in my groin. Now was not the time for a hard-on!
Right, I told myself. Try it, you can always leave if things get too weird.
Leave? said another part of myself. And where would you go, Mr Two-suitcases-no-money-no-job- nowhere-to-live?
I swallowed, and undressed, down to my T-shirt and briefs. First I put on the socks; they went up to my knees. Next the shorts, which fit okay across the waist, but were strangely hugging around my hips, groin and ass. Mr Braithwaite couldn't fail to see my boner in these, or my trim round ass. But that is probably the point, said that inner voice again. He's a dirty old man, and by putting these clothes on you're submitting to him. The thought made me stop, but only briefly. A strange feeling told me that I wanted this, an unshakeable feeling. Next came the shirt, which fit well, though the collar was ever so slightly tight. I actually enjoyed the feeling of the snug grey shirt collar, which I could feel had been starched a little. I tucked the shirt into my tight grey shorts. I put on the striped tie, tying it close in my collar. The blazer fit well also; Mr Braithwaite had searched for the right fit for this uniform - and he'd only had a day. I suspected he knew exactly where to go for it. I put the shoes on, and the cap. I was alarmed to find that my hard-on hadn't gone away, but was instead as big as I'd ever known it to be. My member was a little over six inches, average penis size, but no good if I ever wanted to be in anything pornographic. Guys in porn always had seven inches at least. Still, we'd had some good times together; and with other people. Now, it seemed, my cock had decided to get a bit rebellious and stubborn;
Thanks, I thought at it. Great timing.
I crossed the room and looked in the mirror on the wardrobe door. There I was, a 21 year old man dressed as a schoolboy. Of course, my body was filling the grey uniform out in ways a boy's would never have done, not only my cock, but my built shoulders and naturally trim waist looked good in it too. I was lucky in this respect - I hadn't been able to afford a gym membership since leaving university, so my inverted triangle physique had suffered a little since then - but my diet (the "I Can't Afford to Eat" diet; one that not even Pamela Anderson could sell) had kept me slim at least. Now though, my body was humiliatingly clothed in this schoolboy's uniform. And I had to see Mr Braithwaite.
I left the room and walked along the hallway to Mr Braithwaite's study. There was a mirror outside, and I checked my appearance again. I was nervous, so my knock was timid and quiet. I heard nothing from within; I knocked louder.
Mr Braithwaite's voice boomed from within: "I heard you, boy, wait there."
I waited outside the room for a few eternal minutes before his voice commanded me enter. I opened the door cautiously and steeped into the study.
"Close the door behind you boy. You were not born in a barn," said Mr Braithwaite. He was sitting at his desk, smoking a cigar. I shut the door quietly and turned back to face him.
"Come here, boy," he said. Boy! I was 21 years old, hardly a boy. Yet, in this uniform . . .
"You kept me waiting, boy. I told you I do not like to be kept waiting," he said. There was a pause. "You are dressed as a schoolboy because servants must wear a uniform, and this one makes it easy to discipline. I knew as soon as I saw you that you are a boy who needs discipline; I can give you what you need, and perhaps you will be grateful, you will certainly be better for it. This is a long term arrangement, boy. I do need you to look after my flat, and you will wear that uniform while you do so. At all times. It will build character."
`Build character': an old one from public schools, I thought. I had to do this, I told myself. I had no other option; it was this or the streets, and Mr Braithwaite knew it. But I had the feeling that I would have entered into this freely anyway . . . but where did this feeling come from? I had no time to investigate, for Mr Braithwaite rose from his chair and went to a cabinet that stood by the back wall of the room. While his back was turned, he told me to stand against the desk.
"Squash that hard little prick of yours against my desk," he added, with a strange tone in his voice. He'd seen my boner, I thought with embarrassment. Despite my increasing humiliation I didn't hesitate to do what he had asked, though.
"As I have said, I will provide you with the discipline a boy needs," said Mr Braithwaite. "And that will naturally take the form of corporal punishment. Though I doubt," he added, "that you even suspected it could possibly take any other form."
I said nothing - it was a rhetorical question, and he was right. I was not too young to have escaped the `era' of corporal punishment in schools. Though it had never actually been inflicted upon me, one of my teachers, Mr Woodhouse, had threatened me with a wooden yard-length ruler, and I had seen other boys on the receiving end of the same implement. I had also seen how it had affected these boys. It had been an effective punishment, at least in the short term.
Mr Braithwaite turned around from the cabinet and closed it. In his hand he held a long cane, lacquered, shiny, and thick. I gulped at the sight of it and began to shake a little. Mr Braithwaite moved behind me, and a little to the left.
"Don't be afraid, boy. I won't tell you that this won't hurt, because it most definitely will. But it won't take long, it won't damage you and you'll be better for it." And then in a much sterner tone of voice he said, "Bend over."
I bent over the desk, and Mr Braithwaite instructed me to place my hands behind my back. He gripped my wrists firmly, and swept the cane through the air a couple of times. It made me jump, but I noticed that my erection, pressed against my thigh, had not gone down at all. I could feel the big vein pulse against my leg. Why was this turning me on?
Again Mr Braithwaite gave me no time to ponder my feelings. He swished the cane again, then I felt it land with a crack on my shorts-covered ass. It didn't hurt as much as I thought it would; it did make me jump however, and I broke out in a sweat. The pain from the blow blossomed out into a little red line of pain, which soon had the company of another stroke. This blow hurt a great deal more, and I let out a small whimper. This stroke was followed by a third, and a fourth, each hurting more than the last as the blows criss-crossed each other. Two more followed, bringing the tally up to six exquisitely painful blows. I moaned, and tried to straighten up.
"No, boy," said Mr Braithwaite sternly. "I have not finished your punishment yet. Stay where you are." I felt him reach underneath my hips, his hand brushing my still-engorged cock absently before unfastening the waistband of my shorts. I felt them come down and drop to my ankles.
"What is this, boy?" Mr Braithwaite shouted. "Why are you wearing these briefs?"
"I - I . . ." I began, but Mr Braithwaite wasn't interested in hearing my excuse.
"This was not part of your uniform; it was not laid out for you. Naughty! I will have to cane you over these before your bare ass. A disappointing start to your discipline regime, isn't it? You have just earned yourself three beatings instead of two, and I will double the strokes on your bare bottom too. Are you ready, boy?"
"Yes, sir," I couldn't stop myself from saying. "Thank you, sir."
Mr Braithwaite grunted approvingly then turned again to my bottom. The cane swooshed, and landed with a streak of pain that made me jerk against the desk. Without stopping, the cane struck home again with a loud crack, and I cried out. The next blow was harder, and low on my buttocks - a tender area, as I discovered. I yelled out again at the pain, yet my cock stayed hard. Mr Braithwaite was right; this was good for me, and deep down I was enjoying my humiliation. Six strokes were delivered to my pants covered ass, my whimpering getting louder. The pain was bad, I think I was on the brink of crying. Mr Braithwaite had shown no mercy so far - this was my first time and he was being vicious enough already. Yet I deserved my punishment.
Before I knew it my briefs were joining my shorts on the floor around my ankles and I thought Mr Braithwaite was squaring up to continue my punishment. But no stroke came. I heard Mr Braithwaite move away from me, and I hazarded a glance up at what he was doing. He was back at the cabinet, putting away the cane. I sighed with relief, my ass was burning already, and twelve strokes like that on my bare bottom would have been too much. Mr Braithwaite heard my sigh, and turned around from the cabinet - brandishing another cane. This one was much thinner and more flexible than the first. I began to sweat again, and shifted my erection against the desk nervously.
"Better for naughty boys' bare bottoms," he said, swishing the cane through the air. The sound was sharper than before. I had no idea what to expect, except great pain. I felt the tip of the cane brush my bare ass, stroking it playfully.
"Please, Mr Braithwaite, sir, please . . ." I begged.
"No, boy, you will not get out of this, or any further beating, by begging me. You have it coming, you deserve it, don't you? Don't you?"
"Yes, sir, yes I deserve it," I said meekly. I thought I was going to cry.
Mr Braithwaite again moved behind me and gripped my wrists behind my back. I struggled, rubbing my penis against the smooth polished wood of the desk.
"And stop that, you disgusting naughty boy."
I froze, and the first stroke lit my ass up with a white streak of pain. I cried out, and choked back tears. Another blistering stroke of the cane, and the tears were flowing. Another sharp crack against my bare bottom, and I was whimpering. By the sixth stroke, I was sobbing. But Mr Braithwaite did not stop, the blows kept coming. The seventh landed with a loud crack, the pain flaring across my poor beaten ass. I didn't know if I could take it any more, my tears were unchecked, my cries and sobs uninhibited. And yet, my throbbing cock kept telling me that I was enjoying it, this punishment was satisfying something inside me. Eight, nine, ten, eleven, and a spectacularly cruel and painful twelve. I was beyond resistance, I gave myself in to my discipline. Mr Braithwaite ordered me, tenderly but with his customary firmness, to stand up. I did, and looked at him face to face. Again his stern features were betrayed by his handsomeness. He did not wipe away my tears, but instead pressed his mouth to mine in a kiss. I felt myself open my mouth to his probing tongue, before he pressed down on my head, gently forcing me to my knees. I wanted to rub my tortured ass, but instead my hands were at Mr Braithwaite's fly, opening his trousers, pulling his hard cock out from his briefs.
"You submit to my discipline, boy?" he asked - unnecessarily, as I already had his engorged member in my mouth and was sucking hard. He grabbed me by the back of the head and forced his cock deeper in my throat, bucking his hips in and out, his cock fucking my face.
"Keep those hands away from your ass, boy," he said, seeing my hands go down to soothe and rub my sore red ass. He kept fucking my face until I felt his cum spurt out into my throat. Like a good cocksucker, I swallowed all he had to give. It didn't take long, as our passions were high. I told him that I wanted to cum too, but he just smiled.
"Naughty boys don't get to cum when they want, boy," he said, almost kindly. I nodded, I had an idea that it would be that way. "Now pull your shorts up - after removing your briefs - and go and stand over there in the corner, with your hands on your head."
I stood up quickly, still tasting the cum in my mouth. I stepped out of my briefs and shorts, then put the shorts back on, the fabric roughly rubbing my sensitive red bottom. I went to the corner, faced the wall, and stood with my hands on my head in disgrace.
"Now I have work to do, boy, so don't you move or make a sound. Understood?"
"Yes, Mr Braithwaite," I replied.
"Good lad. Perhaps I'll let you cum later on, if you're good."
"Thank you, Mr Braithwaite," I said, but I didn't care. I didn't care because my ass was red hot and tingling and my cock was hard from the beating; though I stood in disgrace against the wall in a humiliating school uniform chafing my bottom, I smiled a little through my drying tears.
Mail the author: boyjack99@hotmail.com