Partially true, partially story.
It all started for me when I was 18 turning 19. I was always a bit shy around girls so was still a virgin. I noticed that I found myself looking at what they were wearing more than the girl themselves. My sister was a couple years younger than me so I kept wearing her stuff when I was on my own and experimenting like that. Eventually I found myself on a chatroom chatting with gay and bi guys as I assumed as I liked to dress as a girl that I must be gay.
I went on a local board and got chatting to a much older guy who was in his 60s. I wasn’t sexually attracted then but he was really sweet and complimentary. He encouraged me to send a few pictures of myself semi naked to him. At the time I was a runner so had a very slim and athletic build. Again he was very complimentary and soon sent me a shakey webcam video of him stroking himself. I was a bit surprised to find myself getting really hard watching him wank to my pictures. “I think we need to meet to show you some appreciation!”. In my horny state I agreed and he sent me his address to go around to now. To my surprise it was only 2 streets over!
Before I could talk myself out of it I had walked out the house and found myself knocking on his door. A well built (but not fat) silver fox answered the door and invited me in. I sat on his sofa, clearly very nervous as he offered me some tea. He sat beside me as we sipped our drinks and he questioned me about my sex life which was a very short answer! “So you’ve never been naked in front of someone?”. I shook my head. As I did he rubbed his hand against my cock which was now rock hard and trying to burst out of my shorts. “I think someone wants to say hello. Why don’t you stand up and strip off for me”.
I stood up and turned away as I took my t shirt off. “No boy face me”. This was the first time he had called me anything but my name and I found “boy” such a humiliating way to address me but it turned me on a lot. Next were my socks before I slipped my shorts off to be stood in just my boxers. “Boy, I did say strip naked. Not just to your underwear. Now continue please”. Shaking a little I grasped the top of my boxers and rolled them down until my cock sprang out then continued down my legs before stepping out of them. I threw them into the pile of clothes and stood there awkwardly trying to hide myself with my hands.
Sir stood up and walked over to me. He grasped my two wrists and made me get into position holding my head with my hands showing off my whole body. Then then nudged my legs until they were at shoulder width sort. “This is the inspect pose. When I say inspect you get into this position. Do you understand boy?” I nod my agreement.
Sir walked around me, looking me up and down nodding in approval until he settled in a position behind me. “So if this is the first time you’ve been naked in front of someone. Would I be right in saying no one has played with that small dicklet?”. Im a bit shocked at being told I have a small cock but I nod my head. Sir hugs me from behind slowly caressing his hands from my nipples down to my cock. He grasps it in one hand and starts to stroke up and down. I go to stop him but I’m told firmly to leave my hands where they are.
“So boy tell me about some of the girls you fancy”. I tell him about some of the girls and what they wear that turned me on. I mentioned one particular girl who used to wear diamond pattern tights with pink socks underneath them who really turned me on and how she used to roll her skirt up. He then made me tell him about my favourite clothes that I had worn so far. I was getting really close to cumming so told Sir, “Boy you will cum when I say”. He Continued stroking hard but then suddenly stopped just before I erupted. My cock didn’t stop and lots of cum trickled out the end but I didn’t feel anything except extreme horniess and frustration. “That was your first ruined orgasm. My boys don’t have orgasms unless they’ve really done well and you haven’t impressed yet”.
Sir wiped his hand in my hair and walked off returning with a chair which he placed just behind me. He sat on the chair and told me to lie across his lap whilst still holding my head. I did as I was told in the hope of getting a proper orgasm later (my first programming it seems!). Sir starts to stroke and caress my flinching bum as he talks “Now boy those clothes you’ve just dumped on the floor. Your mother may allow it but not in my house. In the future when you arrive here you will strip in the hall. You will then fold your clothes and pass them to me for safe keeping. Naughty boys like you receive spankings when they’ve been bad. How many spankings do bad boys deserve?”. I have no idea what number he’s looking for so say 10. “Incorrect and for trying to escape punishment I am going to double your spankings. In this house I punish in multiples of 25 so you will now have 50 spanks for 2 infringements”.
Sir raises his hand and brings it down hard against my left cheek with a loud slap. I wriggle and shout owe trying to block the next one. “That’s your 3rd and 4th infringement. Firstly the etiquette is to count the number then thank me and ask for another. For every spank. Secondly you must never remove your hands from your head. You will now receive 99 more spanks, remember the rules”. I start to beg and plead with Sir to be lenient but he just shakes his head and starts again saying if I continue speaking he will call it a 5th infringement. I shut my mouth. He brings his hand down again and I do as I’m told counting, thanking and asking Sir for more. Sir is quite the expert and switches from cheek to check ensuring an even coverage until my whole bum is red. He gets to 50 and says “as you are new we will save the rest for later. We don’t want to scare you off so we! Now up you get. Fold up your clothes and then go and back us some more tea. Mine is milk and 1 sugar”.
I do as I’m told and go to sit down on the sofa. “No boy. Only men and ladies sit on the sofa. Do you think men allow themselves to be spanked? No, boys sit on the floor”. I sit down and Sir encourages me to scoot closer to him. Eventually I am between his legs as he strokes my hair as he watches some tv. As The episode of Sir’s show finishes he sits up and tells me to lie across his lap again to continue with my punishment spanks. He goes slower this time but spanks much harder than before really pushing me to my limits. My bum is red hot and very sore by the time Sir reaches the 100th spank.
“Well done boy. Now I’m sure you’ll be a better boy going forward now that you know what is coming. I know you need to leave soon but I’d like to see you again if you agree? Perhaps we could make this a regular thing?”. I look at Sir and nod in agreement. “Good you will come back tomorrow at 9am. If you’re good you will get a reward”. Sir passes me my clothes and shows me to the door.
The night goes by really slowly as I cannot wait for the morning to arrive. I’m up and at Sirs door however I’m a minute late, I’m sure that’s ok.
Sir opens the door and simply states “you’re late”. He beckons me in and stares at me. I remember what I was told and strip right away folding all of my clothes carefully and nearly before handing to Sir. “You have learnt boy but you need to learn timekeeping as you were 1 minute late. Time is very important to me so that requires a more severe punishment than normal so that is 50 hard and slow spanks”. He walks me to the sofa and sits down laying me over his knee again. My bum is very sore and has started to bruise a little but that doesn’t stop Sir slowly but firmly spanking each cheek until I count to 50. I’m holding back the tears which is pathetic as I’m nearly 19 and here I am holding back tears!
“Right stand up in inspection pose”. I do as I’m told standing up straight with my hands on my head. As he did yesterday he runs his hands all over me inspecting every square inch of my body. By the time my inspection has finished I am rock hard and dripping.
“You’d best lose that erection quickly boy. I have my Saturday papers to read but you need to get them first”. The shop is only a mile away which is ok but Sir has some other ideas. “Have you had anything in your bum before?”. I shake my head although he already knew the answer. He holds up a large black plug and tells me this is what you’ll be wearing. Sir then explains that I need to be douched first and what it was as I’d never heard of one before. He took me to the bathroom and helped me to douche warning me to pay attention as this is the last time he’d do it for me.
Once freshly douched Sir takes me back to the front room and makes me get into doggy style position. He grabs the plug and covers it in a gel. Next he dollops some more gel onto his finger and slowly inserts it into my bum filling me with gel. I feel Sir push the plug against my hole. “Pucker up boy, this will feel tight and maybe a bit sore at first but you’ll get used to it”. I feel Sir pushing with what feels like a fair bit of pressure but eventually with a satisfying squelch the plug pops into position making me feel really full! Sir wipes the excess from around the plug and my hole before standing me up. I am handed back my clothes, given some money and directed to the shop.
The walk is only a short one but I feel the plug with every step and it feels like I’m adjusting my walk although I’m sure it’s all in my head. I’m soon back at Sir’s house with his order and stripped as is now normal. Sir sits back in the sofa and beckons me to lie in doggy in front of him so he can use me as a foot stool.
As he sits back reading he tells me of his plans for me. “So boy. I had a boy around your age for a couple of years before he moved away so I’m looking for someone to replace him. So far you’re doing well and I think you could be the one. He used to come here daily and see to not only my sexual needs but also my domestic needs. In return I provided him with the training he desired. What do you think?”. I cannot say yes quick enough to this offer to Sir’s obvious delight. “Excellent, I’m off to watch the football in a few hours when you’ll have to go but until then you have a long list of chores to do. You can find them on the wall in the kitchen”.
I get up and find the list detailing the hoovering, dish cleaning, bathroom and toilet cleaning that Sir wanted done. I spend the next couple of hours cleaning as Sir comes and comments on my work. I just finish my last job as Sir comes in and says “boy it’s nearly time to go. You’ve worked hard so I think you’ve earnt a reward. Have you ever touched a cock other than your own?”. Again this is a question Sir knows the answer to but he wants to hear me say it. “Well get on your knees and wank me”. I do as I’m told and sink quickly to my knees. I undo Sirs belt and ease his trousers to the floor. I peel his boxers down and see his cock for the first time.
It’s flaccid although starting to get a bit harder. It’s a big size even flaccid, far bigger than mine! I take his cock in my hand and rub the head with my thumb to make it twitch into life. I lick the tip but as I do I get a hard slap to my face “I said wank not blowjob you stupid boy!”. I work his cock hard working the precum into his cock as lube. It’s not long before Sir slaps
My hands out of the way and takes over “open your mouth and stick your tongue out”. I do as I’m told and eagerly await my reward.
Sir is a very heavy cummer and shoots a strong stream into my nose/eye before adjusting and sending the rest onto my waiting tongue. Sir scoops the cum off my nose and around my eye and puts it into my mouth and tells me to swallow. I’m not sure what to make of the taste but I’m mostly thinking about what a slut I am now that I have another man’s cum heading to my belly. Sir rubs his cum and precum covered hands on my hair as he tells me “good boy. Now get dressed and be back again tomorrow at 9am again”.
