TRAINING BEN

BY TOMMY

[ part 4 ]

It was just after eight thirty when I came down the next morning. Ben was awake and his eyes followed me anxiously as I placed the breakfast things on the table. “Time to get up little one.” I said, untying his hands and feet. Examining him all over in the shower, I removed his butt-plug and was pleased to see that he was almost back to normal. The powerful spray I used had turned his pert buttocks back to their normal silky white smoothness. I decided not to put his cock stretcher on, but ensured that his genital ring was nice and tight. When he was dry I gave him a plate of stale bread and a glass of milk which he devoured within a minute. I sat down at my chair, had a few sips of tea and waited. Had he got the message? I didn’t have to wait long. Holding the paddle nervously, he came to my chair. “Please sir, may I warm your toast please sir?” I smiled. “How kind of you to offer Ben.” I took the paddle and he climbed onto the punishment bench, gripping the bar down in front, and pulling himself forward so his buttocks were in the correct position. I didn’t waste time restraining him but started the spanking immediately. I saw him grit his teeth and grip the bar even tighter, but apart from a few short yelps, he managed to get through it without crying. “Your bottom’s nice and warm now Ben,” I said, feeling his red posterior. I smiled. “However, I really would like my toast a little hotter this morning. What do you suggest?” I heard him swallow and choke back a few sobs. “P..please sir, please would you spank me again sir?” he asked quietly. “Of course Ben, if that’s what you want. How hard Ben?” “Very hard, please sir.” I heard his shrill voice say. This time I spanked him really hard, the paddle making his backside bounce up and down like jelly. He squirmed and yelled as each blow fell but didn’t alter his position or let go of the bar. I stopped, my arm aching. “I think that’s probably hot enough now!” The toast was delicious.

Having received a few emails from clients requesting me to phone them, I decided to devote the rest of the morning to this task. I settled myself down in a small armchair and ordered Ben to kneel in front, between my legs. “You know what you have to do Ben. Nice and slowly.” I started dialling, watching Ben’s little hands fumble with my zip. Discussing with the clients what Ben could and couldn’t do and what they could do to Ben in intimate detail while being sucked by the boy in question, was incredibly exciting. The last name on the list was the Headmaster, and I saw little Ben tense as I said who it was. “Yes, yes of course Headmaster….didn’t bother to check you’d signed it….I agree….needs a sharp lesson…would you….so kind.” Ben looked up, his large innocent brown eyes glistening. “A new cane just arrived?….of course….sure he would love to be the first……yes he told me…in bed…dirty thoughts…absolutely……” I pushed myself down in the armchair. “of course a boy will have erections….you didn’t notice?…obviously hiding them from you….yes, of course….probably masturbates in secret…...investigate…..severely punished…..yes, I agree…as soon as he arrives…..goodnight Headmaster.” I finished my phone call just in time. I couldn’t have lasted any longer. Rolling my head back I came in Ben’s mouth. He tried hard this time and managed to swallow everything, though not without making a great deal of noise.

Now fully relaxed I put Ben on my lap and stroked his head, my hand playing with his cute little penis, slowly pushing his foreskin back. “Well my little schoolboy, it looks like you’ll be quite busy soon. Lots of people want to play with you, especially the Headmaster.” I paused, stroking his balls. “So you better start getting this willy nice and stiff pretty soon. They do like little boys to have erections you know.” I took his soft willy in my hand and began to rub it. “Most clients enjoy sucking a little boy’s cock and they get very disappointed if the boy can’t keep it hard!” Ben sat still and watched what I was doing to him. “B..but sir, “ he started, in a puzzled voice. “But sir, if my willy goes hard at the Headmaster’s house, he’ll cane me sir.” I smiled. He still hadn’t fully understood. “Yes, Ben of course he’ll cane you, that’s the point!” I held him closer. “Ben, the Headmaster is a very good and respectable man who enjoys two things, fucking and caning naughty schoolboys. He likes to have a reason for caning you, and if you have an erection, that will be another reason for him, and he’ll be very happy. Do you understand Ben?” Looking at his worried expression, I wasn’t sure he did. Concentrating on the task at hand I managed to get his penis sticking up slightly, but it was clear that his anxiety was hindering my efforts. “Not to worry though,” I said cheerfully. “I’ll start you on a course of viagra today. That ought to help.” I’d only just said this when the phone rang. After a lengthy discussion, I replaced the receiver and gave Ben a cuddle. “That was the Headmaster again Ben. Seems you’re going to be famous.” I started to push my finger down between his legs. “He’s just bought a very old cane in an auction-over one hundred years old! On of the first rattan canes to be used in a school-and it’s in perfect condition.” Opening my legs slightly I stuck my finger up between his buttocks. With my other hand I started to play again with his willy. “The Headmaster wants to organise a ‘Victorian evening’ next week for a small group of important guests and he’d like you to come dressed as a victorian schoolboy,” I prodded his hot little bumhole. “There will be two other little boys there as well, a little younger than you, but you’ll be the first one to feel the cane, and that’s a great honour! You’ll have to be on your best behaviour and entertain them for a few hours, passing round drinks, sitting on their laps, letting them put their hands down your trousers, feeling your hole, being a sweet little schoolboy.” I eased my finger into his sweaty anus and explored further. “Then the Headmaster will make a speech and call you forward. You will take the cane round for everyone to examine and return it to the Headmaster.” I stuck a second finger up into his bum. “He will then order you to strip naked, he’ll bend you over a genuine victorian school desk and give you six strokes with the cane.” I felt his little prostate and poked it. “Then, after showing everyone your stripes, you go off to a room with one of the guests for twenty minutes or so. While you’re gone he canes the other boys, then you return for another caning and so on all evening.” I noticed that his willy was starting to rise a bit more, and massaged his prostate harder. “When the party has gone on for long enough, he wants all three of you boys to stand side by side and bend over in front of the guests so they can examine your backsides and vote on which is the best thrashed bottom. Then finally, the Headmaster begins the stamina competition where you mustn’t make a sound while he continues to punish you. The first two boys to cry both receive twelve strokes with the birch and the one who’s left wins a prize. The prize is the chance to be the star of a real film!”

Ben was only half listening. His head on my shoulder, his breathing seemed to be a little faster. I didn’t elaborate on the prize. The Headmaster had asked everyone not to tell the boys for a very simple reason. He was going to make a film about corporal punishment and sexual abuse in victorian boarding schools and intended it to be as authentic as possible. Ben’s little penis was now fully erect and I felt him squirm as I rubbed it, my other hand busy teasing his prostate. His buttocks clenched and his hands held me tightly. “Stand up Ben!” I ordered quietly, keeping my fingers up his arse. In one movement I had him standing in front of me and took his throbbing willy in my mouth. My tongue played with it for only a few seconds before he squealed and shook slightly. His orgasm was intense but he was too young to ejaculate. I continued to suck his shrinking willy while he gazed at me in bewilderment. “Some clients will want to do this Ben,” I explained, licking the tip of his glans. “Some of them like your willy soft, some prefer it to be hard, and some like to bring you to orgasm-like I did now. You must do exactly what they tell you!” I tickled the sides of his balls. “Because you’re a young fit boy, you should be able to have your willy hard again in a few minutes.” I had an idea and quickly slipped my pants down. Bringing the boy to orgasm had made me horny as hell. “Go get your arse ready for fucking Ben!” I whispered, settling back in the chair. Ben ran to the table and took a tube of lubricant. One lesson he’d learned was to prepare his bumhole by himself. I saw him rub plenty inside and out, then skip back where he stood meekly, hands by his sides. I sat him on my lap, facing me and jiggled him about till my cock was nudging his bumhole, then lifted him and started to lower him onto it slowly. As usual he bit his lip and flinched as I pushed inside, but I didn’t stop till I everything was in, my thick cock stretching his tight bumhole and buried deep up his rectum.

“Why are you crying Ben?” I asked, seeing tears run down his cheeks. “Sir, i..it’s hurting sir…s…so tight sir.” “Really Ben, you should be used to being fucked by now.” I told him, closing my eyes. I showed him how to move himself up and down on my cock, while I just lay there. He leaned forward more to get comfortable and I felt his buttocks clench, gripping my cock as he jiggled up and down. I held his sides and pulled him down hard, coming in spasms. After the usual licking me clean I allowed him a few minutes to go and wash himself. When he returned, I smiled and stroked his tiny willy. “You know Ben my little bumboy, there are people who like to smoke after sex.” He looked down at my fingers teasing his foreskin. “But personally, I prefer to thrash a lovely backside. It’s so fulfilling!”

I pointed to the desk. “Bring me the small cane Ben.” Nervously Ben obeyed and handed me the rather short light whippy cane I reserved for occasions such as these. Although it could sting like crazy it wasn’t quite heavy enough to bruise easily. Ben looked at me pouting. “P..please sir,” he began. “Please sir, I did what you said sir and I tried to be a good boy sir.” “Yes?” I asked, interested. “Please sir, why are you going to cane me sir?” he asked pitifully, his eyes full of tears. I looked puzzled. “Why?” I repeated. “Because Ben, you’ve got a beautiful bottom and I enjoy caning it.” I answered. “No other reason Ben.” I looked serious for a moment. “Don’t you ever ask me again why I beat you! It’s nothing to do with you. You just do as you’re told and concentrate on getting that backside of yours as high as possible!” Pulling him gently over my lap I relaxed and with one hand firmly on the small of his back, I flicked his buttocks playfully with the cane. I played with him like this for about fifteen minutes, most of the strokes not even painful, a few hard ones sometimes getting a small yelp from the other end.

Suddenly remembering the school uniform that the Headmaster had sent, I stood the boy up and unfolded the clothes. “Let’s see how you look in these Ben.” I said, putting the little white shirt on him. “Don’t think though that I’ll allow you to wear them for very long. For you, clothes will only be allowed when clients request them! Can you do the tie yourself?” I asked, placing it around his collar. “Yes sir” he replied, tying it himself, though rather badly. I grinned. Just one more excuse for the Headmaster to use his slippers and canes! I held up the grey shorts. They were made of thin stretchy material and had no pockets or zip. I pulled them up tight and smiled. Slightly see-through when stretched, they hugged his bottom tightly, disappearing deep between his buttocks like ballet tights. At the front, his little genitals, already pulled forward by his ball ring, made a provocative bulge in the shorts leaving nothing to the imagination. It was clear that even a slight erection would be noticed immediately and I made a mental note to ensure that Ben would arrive next time with his bulge twice as large. Our best client must be kept happy! I picked up the cane.

“Right Ben, let’s see what they look like with you bending over in them, come on!” I ordered, flicking him with the tip of the cane. He touched his toes and looked round. “Is this okay sir?” he asked sweetly. Good boy, he was learning. The shorts looked gorgeous on him.. I didn’t think they’d offer much protection and decided to find out. “Legs open a little more, bum up!” I adjusted his position until it was just right. “Right Ben, keep still while I cane you!” I gave him six strokes, not too hard, but enough to make him yelp and sniff as he fought back the tears. “Stand up and take those shorts off!” Squirming a little he obeyed, putting them gingerly on the chair and glancing at me to make sure he’d done it correctly. “Bend over!” I ordered, brusquely. The next six strokes I aimed lower down than the previous six, but using the same force. Ignoring his little cries I examined the thin red marks in great detail. “Well Ben, it’s clear that the shorts do give some protection so you will only wear them when visiting the Headmaster.” I ordered him to stand. “Take off the shirt and tie!” I said, flexing the cane. “I want to see you with nothing on! That’s how you’ll stay!” He obeyed and within a few seconds was completely naked again.

“Before your next session with a client Ben, I want to make sure you can do everything expected of a little cuntboy.” I stroked his balls gently. “I want that willy up again-come on , you’ve managed it once already!” I teased his small cock with my other hand. His penis stirred and rose slightly. “You see Ben, it’s getting bigger-and no injections either!” I said, smiling. If you can get it stiff now, I think a course of viagra will keep the clients very happy-especially the Headmaster!” At the mention of this name, I saw his willy start drooping rapidly. I sighed. “Okay, we might as well start straight away.” I went over to a cupboard and returned with some small pink tablets. “Take these”, I told him, handing him a glass of water. “You take two of these three times a day and your cock will be sticking up like a flagpole!” I held his waist lightly.

“Another thing Ben. When you’re with clients, I want you to flirt with them and be ready to do anything they ask.” He looked at me with his big innocent eyes. “Please sir, what does flirt mean sir?” I laughed and pulled him closer, my hands fondling his soft chubby buttocks. “I mean Ben that you tease them a little and act like you’re desperate to be fucked. Look I’ll show you.” I sat him on my lap. “You put your head against the clients chest and let him cuddle you. If he wants to play with your willy, you open your legs wider-like so. If the client takes your hand and moves it to their privates, you slip your hand down their trousers-or up their dress if it’s a lady-and play with them.” I showed him carefully what to do. If the client plays with your bottom, you must wriggle a bit and smile nicely all the time. Usually they like to examine it and see how tight your bumhole is. If they stand you up, you lean forward, hands on your knees and stick your bum out-like that, yes. Look round and smile sweetly at them-that’s right.” I placed my hand on his head and pushed him gently down to his knees. “If a lady or gentleman client shows that you should be down there it means they want you to use your mouth to make them happy. Some might allow you to use your hands as well, but many clients like to see a boy using only his mouth. ” I stood him up. “Sometimes there are other little boys and girls there and you might have to play with them as well.” He looked up puzzled. “The clients sometimes have several boys or even girls at the same time and they like to watch you do things to each other.” I stroked his wavy hair. “If you’re lucky you’ll be made to fuck each other. Some clients like to see you fighting. Some want to see the boys fuck the girls, others want the girls to tease the boys.”

I looked at my watch. It was almost lunchtime. “Right Ben. I have to go out for a while and while I’m away I want you to clean the room, then do a bit of exercise.” I led him to a door, unlocked it and switched on the light. This was a small but well equipped gym. I showed him the equipment, the running machine, weight training apparatus and rowing machine and demonstrated how to use it all. I pointed to the clock. “When I come back at six o’clock I want to see you covered in sweat from your exercises. When you hear me arrive you will take the little bat and ask me very nicely to warm your balls. You’re seeing a client tonight so I don’t want to thrash your bottom any more.” I paused for a second. “Remember what I said about a change in your behaviour Ben! “ I left him a few plates of cold meat and bread for his lunch, two viagra pills, a glass of water and went out.

It was almost half past six when I got back. I ran down to the gym and found Ben on the rowing machine, his thin arms trying to pull the seat forward. He saw me and jumped up, running to the table and picking up the small bat. “P..please sir, w..will you warm my balls for me please sir?” I smiled as I saw the effort he’d put into this request. “Oh of course I will Ben, if that’s what you really want.” The strenuous exercise had warmed him up and his testicles hung down, swinging freely between his legs. I prodded each small testicle in turn, pretending to examine them as I would a squash ball. “Okay Ben. Let’s get you ready shall we.” I swiftly secured his hands and then his legs with the separating rod. I didn’t have much time so I gave him about thirty hard slaps, hardly allowing him time to get his breath back after each blow. He squirmed and cried his eyes out. I gave him a couple of injections, a quick drink with painkillers and a few more viagra tablets. “Tonight Ben, you’ll meet a very nice lady who’s very interested in art,” I said, untying him when his crying had ceased. “She likes photographing boys and girls in funny positions so you have to do whatever she tells you!” I’d noticed it was quite cold outside so I gave him a small dressing gown to wear.

It was early in the morning when I picked him up. My colleague hauled him out of his car and into mine. “Poor boy’s exhausted!” he muttered as I closed the door. “Did you get my message?” he asked anxiously. “Yes,” I replied, smiling. “The Headmaster really has taken a shine to him, hasn’t he!” He laughed. “Well I promised the boy would be there just after lunch, in his school uniform-don’t forget!” “Don’t worry, I’ll meet you here at one o’clock.” I said. “I’ve started him on viagra, so that should please the Headmaster.” I added, laughing.

Back at the house, I washed the small boy under the shower and gave him something to eat. “So what did the lady do then?” I asked, examining his little penis and pulling the foreskin back. “Sir, she took lots of photos sir.” He replied, flinching slightly as I examined his uncovered glans. Pouring a glass of water, I made him take his viagra pills. “What did you have to do?” “She had some little girls there sir, and they had their photos taken as well sir, and she made my willy hard sir and I had to put it in their holes sir, then some men came sir and she told them to f..fuck me sir.” I turned him round. His bumhole was red and sore. Wasting no time I sprayed it liberally and put him to bed. “You can sleep for a little while now Ben, I have to wake you up in three hours.” I switched off the light.

Late as usual, I woke Ben and thrust the little boy, half asleep into the shower. Drying him quickly, I dressed him in his uniform, Ben looked up, rubbing his eyes. “You’re going to stay with the Headmaster again.” I said, grinning. His expression was a sight to behold, a mixture of horror, disbelief and dumb resignation. I handed him four pills and a glass of water. “Take these Ben!” He obeyed, and I pulled his thin grey shorts up tightly. Smiling, I rubbed his little bulge. “With the help of a small injection and these pills Ben, your willy will be pushing a hole through these shorts for the rest of the day. “B..but sir, the Headmaster will…” “Yes Ben, the Headmaster will be angry and he’ll probably spend the rest of the day playing with your willy and caning you, and that will make him happy!” I stroked his hair and gave his buttocks a hug. “Ben, don’t forget that he can’t fuck you and cane you at the same time. Try and flirt with him a bit, wriggle your bum and look sexy. It may save you from a beating.” I picked up an envelope and the small wooden bat. “Since you won’t be back until tomorrow I’ve written another letter asking the Headmaster to warm your balls later today.” He looked at me, devastated. “If I were you Ben I should try to be very obedient today. The Headmaster sounded very angry with you on the phone!”

Half an hour later, I handed him over to my colleague. “He’s all ready.” I said, preparing a syringe. Swiftly I gave him an injection in his penis. “One should do it.” I explained, shutting the door. “He’s had plenty of viagra and I don’t want to exaggerate.” I laughed. “This Headmaster’s going to be busy today!” “Anything planned for the next few days?” he asked. “No, I’m giving him a break for two or three days.” I explained. “My sister’s coming to stay and she’ll want some time with him!” I suddenly laughed. “You met her a few years ago, don’t you remember?” He chuckled. “Oh yes, I remember! She’s quite a disciplinarian as I remember.” “That’s right, the boys really love her!” I said. “Hard work, regular beatings, exercise, obedience tests, hygiene, cock and ball torture, anal examinations- and that’s just the mornings!” I added jokingly. We chatted for a few more minutes before finally driving off.

When I picked Ben up the next morning I could see instantly that the Headmaster had been very busy. He didn’t make a sound during the ride home apart from a few quiet squeals when we drove over bumps in the road. Back at the house I saw that his buttocks had been the focus of much attention.. There was not one place that wasn’t bright red or bruised. After treating his scorched flesh and giving him a drink of orange juice, I discovered, on questioning him, that the Headmaster had not been the only teacher this time. Apparently he’d had a student teacher who’d assisted the Headmaster in his lessons. Having heard stories of the Headmaster’s gay lover, I assumed it was the same man. Certainly Ben’s small bumhole was red and sore from constant use. “Was the Headmaster pleased to see you?” I asked, continuing my examination. “A bit sir,” he replied meekly. “But my willy was sticking up sir, and the new teacher thought it was funny, but the Headmaster was angry sir.” I told Ben to continue. “He let the other teacher spank me but it wouldn’t go down sir, so the Headmaster gave him a slipper to use.” Ben looked up. He didn’t spank very hard sir but then the Headmaster told me to take my shorts off and they examined my thing and the Headmaster showed him how to use the cane and he practised on me until my thing went down sir.” He wiped a tear from his eye. “Then they took me to the gym sir and I had to do exercises sir, then they made me lie over the big bench while they f..fucked me sir.” His voice trembled. “After my shower I had some lessons and the new teacher made me learn poems and say them but he kept putting his finger in my bottom sir and the Headmaster said I wasn’t trying hard enough sir, so he caned me sir, then he made me bend over a desk and s..suck his thing while the new teacher caned me again sir, then…” I allowed him to continue for a while.

“So Ben, did you get some sleep this time?” I asked, rubbing a mild corticosteroid cream into his anus. “No sir, sorry sir,” he replied sleepily, flinching as I treated the worst bruises on his buttocks. “The new teacher slept with us sir,” he explained innocently. “He kept playing with my willy sir and making it go hard, then he sucked it, then told the Headmaster and I had to fetch the cane sir!” He wept at the memory. “The new teacher kept fucking me sir and then the Headmaster woke up and blamed me for making a lot of noise sir, so I had to go and get another cane, then he made me suck his thing sir while the new teacher fucked me.again” He looked so distraught at this and spilt his orange juice. “He was angry with me because I didn’t swallow everything sir, but it wasn’t my fault –really sir. The other teacher was pushing so hard sir! They were both angry with me and they both gave me six really hard strokes each sir. Then I couldn’t sleep because of the pain sir, and I was just falling asleep when the Headmaster said it was time to get up.” Ben looked down and sobbed. “He said I needed my balls warming before I left and he used your bat sir, and then his friend said he wanted a go so he did it as well sir!” I felt his little testicles and he flinched. “So you got them warmed yesterday and again this morning did you?” I asked, preparing a syringe. “Yes sir,” I heard him say tearfully. “Please sir, he read your note when I arrived and did it at lunchtime sir.” I injected some antinflammatory drugs into his balls and wiped his eyes. “Well Ben, you won’t be going to the Headmaster’s house for a little while. We have a visitor arriving the day after tomorrow and I want you here.” I tousled the sleepy boy’s hair and got him something to eat. “As soon as you’ve finished eating, I want you on your bed ready for fucking!” I said smiling. “Then you can sleep till the afternoon.”

The next morning I was pleased to see that his behaviour had continued to improve. As soon as he’d had his shower and I’d tightened his ball ring, he asked me sweetly if he could ‘warm my toast’. Tiring of his usual position, I tried something different. Lying him on his back I made him hold his legs up and wide apart while I paddled both his bottom and the insides of his thighs. Ignoring his crying I made him bring his knees up to his chest and hold them tightly with his hands. “There, you see,” I said, slipping a few pieces of toast between his thighs. “I can warm my toast and play with your willy at the same time.” I ran my finger over his anus, smiling as he shivered. “I can keep an eye on your bumhole as well!” I added, laughing.

Most of the day I kept the boy extremely busy. Adjacent to the main chamber were several other rooms used only when visitors arrived. Not just spare bedrooms, but a smart living room, dining room, kitchen and various other rooms that I hardly ever used. I unlocked the doors and got him cleaning and polishing. Due to liberal application of sprays and creams, the bruises on his buttocks had disappeared by the evening and the continuous high doses of viagra meant his penis was almost always half erect. Taking him around the rooms I showed him how to pour drinks, lay the table, serve food and generally how to behave as a little slaveboy. “Ben, the lady coming tomorrow will expect good behaviour and total obedience, do you understand?” Ben, nodded meekly. “Yes sir.” He replied, his naked body covered in a film of sweat from his work. This was the first day when I hadn’t beaten him and I also gave him a break from his daily ball warming sessions. I smiled and tickled his balls lightly. His penis started to rise immediately. “Good!” I said laughing. “Just how it should be.”

That evening I sat in one of the deep leather armchairs in front of the living room fire. A glass of brandy in my hand I smiled contentedly as the small panting boy straddling me moved himself up and down on my cock, his buttocks clenching and unclenching rythmically as he’d been shown. The feeling as his tight anus gripped my throbbing cock was amazing. His little willy flopped around, sometimes tickling me. Unable to hold back any longer, I came deep inside him but he didn’t dare stop what he was doing until I ordered him off. He knelt between my legs and was soon busy sucking my now-soft cock, licking it clean and attempting to get it hard again. I stroked his head. He was learning. I took another sip and thought about tomorrow, suddenly shivering as his tongue found a particularly sensitive spot. Feeling myself getting hard again, I quietly ordered the boy back on top and closed my eyes.