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Meeting Sir as a Cross dresser
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I started dressing when I was 19 in some cheap stuff I bought from Asda. At first it was just the dressing that excites me but I found myself fantasising about being with a guy whilst dressed. I was a bit confused but eventually decided to act on my urges and find a guy. 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”. |
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The next couple of weeks come and go with me visiting Sir for at least a couple hours each day. The format is the same; quick inspection, some housework, some corrections for poor cleaning or other infringement before being allowed to wank Sir off and I’m sent on my way with his creamy goodness in my belly. I really want more now but don’t want to push it and scare him off. Guess this is all part of why he does this.
I arrive once again at 9am on the dot, strip and stand for inspection. This time Sir grabs my bum and tells me “I want this grown. You’ll follow this workout plan daily to grow it and I expect results”. After this instruction I start my daily chores.
I am sat next to Sir with numerous shoes that I’ve been tasked to polish to a shine. “So boy how much do you wank when you’re not with me?”. I’m a bit taken back but the question but answer honestly stating about 3 times a day. “What do you think about?”. This is easy I answer. I dream about serving him! “Mmm good answer but you wank too much”. Sir sits back and continues to read his paper, “yes far too much” you repeat. At the end of our time again I am allowed to wank Sir and take more if his cum in my mouth.
I arrive eagerly again the next day. Strip and inspection as normal. This time once inspection is finished Sir walks off and comes back with a suit bag.
“You’ve been such a good boy I think it’s time for more of a reward for you. Remember the first day we met and you described the girl you fancied and how you liked what she wore. Well I went and bought the exact outfit for you. Of course I told them it was for my granddaughter but how will they know! I Also bought some diamond tights and pink socks and underwear so you can copy your idol exactly! Do you like it?”. I thank you profusely but you stop me.
“Girls don’t have little dicklets like you though. If you dress up in this you have to wear chastity for a month. Sounds fair? Stop you wanking quite so much too!”. There’s so many questions in my head but the first one is what is chastity. To this Sir shows me this little steel cage which will cover my cock. He says again if I want to wear the dress then I need to pay the price. I nod and allow him to fit it without any more questions. Sir padlocks the cage shut and places the key in his pocket. “Good girl, you can go and write release date on the calendar a month from now”. I do as I told walking awkwardly as this piece of steel swings between my legs. “You can wear the dress once you’re done with your chores. You don’t want to ruin them now so you?!”.
I work through my chores as quick as possible whilst paying close attention to the quality of work eager to get my dress. Sir has laid my clothes out neatly on the bed and tells me to get dressed before coming out to him.
First I pull on the tiny pink thong that just covers the front of the cage and the pink socks. Next I put the tights on being careful to not ladder them. Next i put on the tight bright pink bodycon dress that hugs my body tightly. The hem line is already quite high but my idol rolls them up so naturally I rolled my hem up too. On my feet were a pair of 6 inch black patent heels which had been highly shined.
I walk out to Sir as feminine as I can although I really struggle in the heels. I find him sat back naked in his chair. “I think it’s time we explored your mouth. Crawl to me and show me what you can do. If you do badly it will be back to wanking though!” |
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I drop to my knees, put out my hands and crawl over to you on all fours. I kneel before you, sitting down on my heels with my hands behind my back waiting for your approval. “Now girl, I’m going to give you 5 minutes to prove you’re a cocksucker worthy of being called a girl. You may begin”. With this you start a stop watch and lean back to watch me go to work.
I’ve never sucked a cock before but think back to my favourite porn films and how the girls in them did it. I take your balls in one hand and lick up and down the shift as I caress your balls. I start licking only around the head of your cock and slowly introduce my lips to the end of your cock. I slowly rock my mouth forward and back, up and down your cock. I think I’m going really deep but in reality it’s probably only an inch or 2. “Not a bad start girl but you’re missing the other 3/4 of my cock!”. I take this as a prompt to go deeper but I can only get half way down before I start gagging and wretching a little but I persist.
The 5 minutes is up far too fast as you count down the last 10 seconds. As you reach zero I continue sucking but you force my head up and push me back until I’m sat on my ankles starting at you with a mix of drool and precum drilling from my mouth and down my dress. “That was ok but you definitely need work. You’ve lost the rights to be called a girl and dress as one. Stand up and strip back down again. You made a mess of your pretty dress so you’ll need to wash that before you go”. I go to argue back but I realise that would be a bad idea so stop myself and do as I am told.
I’m dejected and feel like a bit of a failure as I drop back onto my knees and perch on my ankles again. You notice this and gentle caress my hair. “don’t worry boy. I know it was your first time and these things take practise. We’ll get you there. Now stop feeling sorry for yourself and wank me”. I do as I’m told and wank until you cum in my mouth again. It was a nice comment of yours but I still can’t help feel bad but I’m determined to improve. “Ok boy back again, 9am sharp tomorrow as normal”.
Before I leave I ask about the chastity and do you want to remove it before I go. “No! You agreed to wear it for a month in exchange for the clothes. That’s not a month whilst you’re here, that’s the full month! Treats have prices boy. Now again, 9am sharp tomorrow boy”.
I spend all night watching porn, paying close attention to how the pornstars do it determines to do a better job next time! The disappointment turns into excitement and I am keen waiting at Sir’s house as 9am arrives.
I enter, strip and inspect as usually but this time I don’t receive a list of jobs. “Boy I’ve been thinking about how we can improve your blowjobs and what I expect of you. I’ve come up with a sissy training area for you to practise. Come boy”. You point to the floor meaning you expect me on all fours as we walk through the house. We stop at the cupboard under the stairs which is a bit odd but everything soon becomes clear as you open the door.
As the door opens I see that the floor has been covered with foam and on the wall is a large 8” realistic looking dildo. Just above the dildo is a counter which counts each time it has been pushed. Just below the dildo is a ring with a chain attached to it.
“I had a think about how we can train you and rather than waste both our time whilst you improve I think it better for you to train alone to master your skills. I think a nice round 1,000 sucks should get you there based on your performance yesterday. That’s not 1,000 small sucks like yesterday. That’s 1,000 balls deep sucks which is what the counter is for. Each full length suck makes your nose hit the counter adding one to the count. You’ll do that until there’s 1,000 on the counter. To make sure you don’t cheat your hands will be cuffed behind your back and this chain will make it so that you can’t fully remove the dildo from your mouth. Don’t worry about safety as a good friend of mine came over last night and set up a little webcam for me so I can keep an eye on you. He knows all about our little arrangement so don’t worry about that. Our meets going forward will be; arrive, strip, inspect, work and then the rest of the time in the cupboard until you hit your quota”.
I must look a bit shocked but I get into the cupboard on all fours and meekly accept the dildo into my mouth as you connect the chain and cuff my hands. No escape now! As you leave me to my task you flick the light switch off stating “you don’t need to use my electricity, you can’t miss the dildo. Don’t worry about the camera, they work in the dark”. With that the door is shut and I hear a lock engage, not that I will be going anywhere! |
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The dildo appears to be a clone of Sir’s as it has the same width and veiny appearance. I push my head forward and quickly find myself gagging after just a couple of inches just like on Sirs. This is hopeless, i’ll never make 1,000! I decide to persevere but 2 hours later when Sir returns and flicks the switch on my score is still 0! There’s a lot of slobber and I’ve only made it to the halfway point!
“Oh boy, that is very disappointing. Looks like you and the cupboard will be getting well acquainted! Same time tomorrow”. I ask if I can take the dildo home but all I get in return is “I’ll think about it”. Im also a bit surprised as usually I’m allowed to wank you off but I’m not even allowed that! “When you stop disappointing me I’ll let you touch me again!”.
Again I spent the night researching desperately how to improve but the next day I fail again and I’m still on zero after 4 hours of trying. Again I’m not allowed to touch you! I’m getting so frustrated.
Just before I leave you grab a bag off the side and hand it to me. It’s another dildo for me to practise on but you’ve kindly wrapped it in a see through bag! I walk home quickly with it stuffed up my top and spend all night practising, even turning down a trip to the pub with my friends. I’m desperate for 2 reasons; firstly I’m really missing my daily cum deposit and secondly I really want to get out of the cupboard! What a little slut I have become!!
The next morning I arrive and carry out the jobs given to me before I am locked away. After about 20 minutes I feel my nose contact the switch and a satisfying click is my reward, just 999 to go! I get into a bit of a groove of easing myself down the stiff plastic cock until I hear a click and then withdraw to give myself some time to breathe. Doing this every few minutes I’m now getting some progress with much less gagging. This time when Sir turns the light on the counter says 55. “Good boy, that’s much more like it! Same again tomorrow”. Frustratingly I’m still not allowed to touch you!
Again I spend the night practising and turn up early the next morning. I’be really got the hang of it now and when you turn the light on I’m now at 120! “Excellent boy, you really have turned the corner”. You undo the collar and walk off which confuses me a bit. “Aren’t you following boy? Don’t you want your reward?”. My hands are still cuffed so I can’t walk on all fours as normal but I follow as quickly as I can. You pull your trousers down and stand in the middle of the room. I get on my knees before you and look up in hope. “Show me what you’ve learnt boy”.
I eagerly take you into my mouth, feeling your cock swelling to its full size as I suck. This time with no gagging at all I suck your whole length reaching your balls time after time. You take my head in your hands and thrust as I push my head forwards. It doesn’t take long before you grab my head pull it into your crotch where you hold it. I finally receive my reward of a very thick creamy load straight down my throat. You pull out and use my boxers to clean yourself. “Well boy that was fantastic! You really have learnt how to suck properly! Imagine how good you’ll be by the time you reach 1,000!”. The look on my face must give away my confusion. Why do I need more training if I’ve satisfied Sir!
“You’ll come to learn boy that I follow through with anything I say. So if I say that you’ll give me 1,000 blow jobs then you will give me 1,000 and no less! You will get rewards when you reach certain milestones as that’s only fair. Now same time tomorrow”.
Over the next couple of days I continue to make progress with each day finishing with a cuffed facefuck. By the end of the 4th day I just tick over 250. After my facefuck you return with a bag full of various types of women’s underwear; thongs, boy shorts, g strings and t strings. “You’re really starting on your journey so I think it’s time for the next step. Tonight you will go home and put all your current underwear in this bag and bring them to me tomorrow. You will replace them with just the underwear in here. This will be your daily wear. I also want you to start growing your hair, something about grasping pig Tails as i facefuck you. Can’t do that with a wig”. I really don’t know what to say but I’m infatuated with you by now so will do anything you say!
The next day I bring the bag of my old boys underwear to you and pick a pretty pink g string to wear. You strip me down but leave the g string on and beckon me to the garden. The garden is very secluded but I can’t help feeling exposed stood outside in just some pink underwear. You instruct me to put my underwear in a bin placed in the centre of the patio before lighting a match and passing it to me. “If you want to continue with your training drop the match into the bin”. It doesn’t even take me a second to think before I drop it. It takes a few seconds to catch but soon all of my boy underwear is gone ready for a fresh start.
I’m really on a roll and It only takes another 3 days for me to reach 500 which is the next milestone. This time Sir makes me crawl to the centre of his room. I feel a cloth or similar wipe over the base of my back just above my bum. I then feel you apply pressure to my back and wipe side to side and up and down before I hear a peeling noise. I hear the click of a camera before you reappear In front of me and show me your handiwork. You have applied a tramp stamp tattoo of a butterfly to me! I must look horrified as you simply say “you’re lucky it’s not worse!” |
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The tattoo that you apply is a semi permanent tattoo which takes a month to wear away but you really enjoy seeing your mark upon me and everytime we meet i’m bent over on all fours with you rubbing and caressing my ass and lower back. One day you slowly rub a finger over my ass making me jump a little. You rub around the hole slowly but never penetrate me with your finger.
“I bet you really want me to fuck you and make you a proper woman don’t you?”. I moan and nod begging you to fuck me. In return I get a hard spank on both cheeks. “I will fuck you in my own time and not when you request it”.
You walk off and grab something from the side. I hear a slight squelching noise and you are positioned behind me again. You stick a black object in front of my face. “This is a butt plug. We’re going to start your anal training so that you’re ready for me when the time comes. As your throat knows I’m quite large. This is only a small plug, far smaller than me but you will wear it daily at all times. You will remove it to go the toilet and to reapply lube but that is all.”
I feel the coldness on my hole as you push the plug up against it. It won’t slip in that easy so you apply quite a lot of force. “Relax boy”. I try to relax but continue to struggle. Eventually with a large relief I feel the plug pop into place. “Wow boy you’re tight, that plug is half the size of me so you need this training badly!”. You make me stand up and do some squats in front of you to make sure it won’t pop out.
You turn me round and just grab at my chastity cage tugging at it as you speak to me. “This is feeling a bit loose boy. What’s it been now? About a month since you last cum? Shame.”. You walk off and return with a key, unlocking me from my chastity cage. My hopes soar that I’m going to be allowed to cum before they crash to the ground again when you pull out a smaller cage. It is a struggle to fit but eventually the lock slides into place. You then pull out a tiny flat cage and tell me “this is the goal to get you into”. It is an absolutely tiny cage, by the time I fit in that my cock will be almost none existent.
With that you take the Lacy pink boy shorts I arrived in and pull them up for me. You sit back admiring the view and just simply tut. “No boy these are too similar to boxer shorts. You’re to not wear thongs from now on. Bring all the other underwear which aren’t thongs back to me and I’ll get you some replacements”. With this you grab the boy shorts and rip them off me. Before allowing me to get dressed again ( minus underwear) you grasp my bum and squeeze complimenting me on the peachy appearance, “those squats are working aren’t they, keep going”
As I leave you whisper in my ear. “I expect you to reach 750 blowjobs on the trainer tomorrow. Don’t disappoint me”. I get a slap on the ass and am sent on my way |
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The new cage is a bit uncomfortable to begin with but by the time I go to bed I’m sort of used to it but I struggle to sleep thinking about how I don’t want to let you down. The morning arrives and I’m around to your house eager to work to get as much time in the cupboard as possible. By the time I have to leave the counter has ticked over to 769. I’ve done it and I think you’re please as I simply get, “good, you didn’t let me down as I’ve got a nice day planned. 9am as normal boy”.
The morning is a bit different for a couple of reasons as firstly I’m put into the cupboard first before I’ve done any work and secondly halfway through my sucking training you stop me to hood me so I can’t see anything.
I have no idea how long has passed but eventually I hear the cupboard door click and a number of people burst out in laughter. “Oh my god, he does have a little cock sucker under the stairs”, says one. Another simply says “what a fucking sissy”.
I’m unattached from the blowjob trainer and a lead attached to my collar. I’m walked on all fours to the living room as I’m heckled on all sides. As we get there you explain to me. “Now boy you know I go the football on a Saturday and these are the lads I go with. They know about my previous playthings but they know you’re a bit different and put simply they want to get in on it. You haven’t got a problem with that have you?”. I shake my head.
“Good boy I knew you wouldn’t but just wanted to make sure. They all live in the area so you probably know some of them or see them around so we’ve decided to keep them anonymous for their sake, not yours. They think the hoods are a bit degrading and uncomfortable though so you’ll be wearing it”. Now boy we’ve got 2 hours until we’ve got to leave to go to the match. Until then you will orally pleasure everyone who puts their cock in your mouth. I’ve been bigging you up a lot and telling them that you’re trained to deepthroat only so that is the expectation. Do not let me down”.
Before we start you ask the group “shall we allow the boy to use its hands or not? No? Ok so be it”. With this my hands are cuffed behind my back and I am manhandled into a kneeling position in front of my first cock. I eagerly take him in my mouth and suck as hard as I’ve sucked before. Before I make him cum I’m pulled off him and thrust upon another cock to which I do the same. Around and around I go for ages without getting any yummy cum as a reward.
So far all of the Cocks have been of a decent size but manageable until I get to the monster. I go as deep as I can but I don’t feel my nose against his stomach as I did with the others. I keep pushing but start to gag and struggle a little. A loud laugh goes out around the room. “I knew you’d struggle with that absolute monster! A lot of the local girls have tried but none can manage it either so you’re in good company”.
I have no idea how long has passed nor how many guys are in the room but I still haven’t had any cum by the time I’ve reached my fifteenth cock. I’m getting desperate to not let you down and also to get my reward so suck like I’ve never sucked before. I’m trying all the tricks I know; moaning and groaning as I suck, licking the sensitive parts of the cock extra hard, vibrating my mouth a little but nothing.
I get warned “You’re running out of time boy”. As I’m warned I get my first thick, warm spurt of cum straight down my throat. The first cumshot is closely followed by a second spurting cock. One by one I’m making them cum. I reach the monster cock again for about the 3rd or 4th time before I make him cum. He almost drowns me the amount of cum that bursts out of him! I don’t get any time to recover before I’m thrust upon the next cock.
I’m almost relieved to hear you announce time is up as my jaw is so so sore. I must look a state as my hood is coated in a mix of cum and spit with the rest dropping all over my body. But I feel like I’ve impressed.
“Right boy. We’re off to the game now. Your list of chores is on the board. I expect them all done by the time I get home. I want you to stay where you are with your hood on for 5 minutes after we’ve gone. Once the time is up you are to remove your hood and start working. Do not take a shower or clean yourself up though!”
Is that it? No well done or even a reprimand? I don’t know what to make of it and spend the next 4 hours fretting over my performance. There’s not much I can do apart from do all of the jobs to a high standard as normal. The last one is a different chore though as it says to cook tea for two and gives me your ETA and says to have it ready for then. I check the cupboards and decide to make a simple bolgonese which is about the only thing I can make!
To impress you I layout the table and put a candle on the table, with a wine glass and a bottle in a wine cooler on the table top. I’ve set out 2 plates and 2 chairs ready for your return.
You arrive on the dot alone in a great mood as your team won. “Ooo spaghetti bolognese, very nice. Dish it up and pour out two glasses of wine. Very nice touch btw”. I do as I’m told and you take your seat. I stand and wait to be told to sit as trained.
Suddenly the door bell rings. “Ahh that’s my dinner guest, go and let them in. They’re expecting you”. I’m shocked. firstly I was expecting the dinner to be for us and don’t have enough for a third person. Secondly I’ve never seen any of your friends and nor have they seen me as far as I know. My nerves are fraying so I rush to the door and open it before I can chicken out and disappoint.
“Ahh hello there, good to see you”. OMG it’s my running coach! The coach passes me his coat and shoes which I hang up and put in the shoe rack. I close the door and follow behind.
“I bet that was a surprise. Your coach is a friend of mine who also comes the football. You got well acquainted earlier”. I look at my coach who laughs and simply says “I hope it was yummy”. You continue; “he said he suspected it before you and I met but when I started telling everyone about you he had a better idea. What gave it away was the butterfly tattoo which he got a fleeting glance at”.
I’m still in absolute shock but you push me to my knees besides the table. “I bet you’re wondering what you will be eating”. I nod my head as you get up and walk to the cupboard. To my horror you return with 2 dog bowls and a tin. You plonk the bowls in front of me before opening the fan and dumping the contents in my bowl before filling the other bow with water. “Don’t worry it’s not dog food, although it looks very similar. It’s beef stew but unheated straight out of the can. You’re to eat and drink without your hands”.
You both proceed to eat your tea and drink your wine as you have a conversation about the football and other items as if I wasn’t even there. I really struggle with my food but again I don’t want to let you down to the extent of licking to bowl clean. Without my hands this is difficult so I use the table leg to help. You both laugh and say “Good boy”.
After dinner the coach thanks you for tea and you tell me to walk him to the door. On leaving he simply says “see you in the week” with a big grin on his face. I could die!
I walk back to the kitchen and clean up before joining you in the lounge. I’m still coated in cum and spit but now have gravy around my face too. “Well boy you’ve had a good day and done very well. I truly am impressed. Would you like to stay over?”. You can barely finish your question before I’m saying yes. “Good I hoped that would be the case. First we will shower you and then I’ve got you a present”.
You lead me to the bathroom where you tell me to get in the bath and kneel down. You run only the cold tape until there is about 2” of water in the bath. “You weren’t expecting warm water were you?”. You take a sponge and sponge my whole body down before taking some girly shampoo and lathering me with that. To finish you take the shower head and hose me down with cold water. You stand me up and help me out of the bath before towel drying me all over. You clearly enjoy this as you’re rock hard. “Get on your knees and thank me”. I do as told and give you a nice deep blowjob.
On completion we return to the lounge where you make me kneel. You leave the room and come back in with a pink fluffy onesie and some slipper boots. Not what I was expecting but I’m cold and tired so thank you for the gifts and put them on. You sit on the sofa and I take my normal position as your feet. “Go and pour us both a glass of wine and you can join me on here tonight”. I’ve never jumped up as quick and eagerly follow your instructions and end the night cuddling up to you on the sofa. I try to play with your cock but you slap my hand away and say “you’ve had enough cock for one day”.
Just after midnight you tell me it’s time for bed and to follow on all fours. I can’t wait to sleep in your bed tonight, maybe tonight or the morning is when you make me a woman? My heart is racing as I enter your bedroom for the first time for it to then sink rapidly as I spot the dog cage in the corner and know what’s coming. You stand by the cage and point saying “get in. Only women sleep in my bed and you’re not one yet”. You shut the cage behind me and padlock it shut. “Good night boy” |
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A loud rustling of the cage startles me awake. “It’s 6am lazy, we don’t sleep in here”. It wasn’t the worst night of my life. Even without a blanket I was toasty and warm in my onesie and spent all night leaking in my cock cage thinking about yesterdays antics. “I’ll have a bacon sandwich for breakfast and a strong black coffee. Bring it up with my iPad and I’ll eat in bed”. I’m half asleep but turn to go to get started on breakfast when I hear “STOP. You don’t work in clothes. Strip off and put them in your bed”. It’s freezing in the house but I do as I’m told, folding them nicely to avoid a punishment and get to work on your breakfast with my nipples hardening in the cold.
I’m very hungry but I know better than to make myself one or even have a nibble of anything without permission. Before long I return to you with your food and drink on a tray and present to you. “Where’s yours?”, you say as you chuckle knowing full well I wouldn’t have done that. “Go make some plain porridge and put it in your bowl. You’ll bring it here first”. Again I do as I’m told.
By the time I’m back in the room you have finished breakfast and are stood up naked waiting for me. “You need to earn breakfast” you say to me pointing at your hardening cock. I suck greedily to earn it but just before you cum you pull out and cum all over my breakfast. “Some extra topping for you”. You put my bowl in the cage and shut it behind me, telling me to eat.
“You made a big impression yesterday. I’m very impressed with you. There was some disappointment in how you struggled with the monster cock so we’ve decided you need some further training. We’re going to increase the size of the dildo in your cupboard to 9. What do you think would be a suitable number of sucks?”. I’m really torn here as I don’t want to stay in the cupboard and it could take me a lot longer with the big cock but I don’t want to annoy with with an undersell. 1,000 I reply. You guffaw, “you silly boy, I would have accepted another 250. But as you wish, you have 1,000 sucks of the big one. Next question for you is whether you want to spend the day in the cupboard sucking or do you want a nice day out? You’re close to 1,000 and that’s when you’ll get your next reward”.
Again I am so conflicted as I really want a nice day out with you but I decide to impress and go for the cupboard. “You really are a glutton for punishment. Cupboard it is. Only after your chores are done though”. I complete my chores and spend the day in the cupboard but succeed in getting above 1,000 to your clear delight. “Well done boy you’ve earnt your next reward next weekend”.
The week goes by slowly with our usual visits of sucking and work but nothing else to mention. Even the running club is uneventful as the coach just blanks me, continuing as normal which drives me wild.
Saturday morning arrives and I’m like a kid at Christmas, so excited! But weirdly I arrive and it’s just another day for you. I’m in the cupboard sucking before being let out for chores whilst you go to the football. You get back and sit in the living room calling me to you. I crawl in to find you sat by a pretty young lady probably in her early 20s and behind her a a German women’s Oktoberfest outfit hanging up with some thigh thigh white suspenders and black highly polished 6” patent heels.
“This is Jessica, she is going to be the croupier for this evenings poker and draft picking. She has also kindly agreed to do your makeup for the first time ever to make you a pretty girl. What do you say to her?”. I thank Jessica before you continue. “What I’ve decided is that you will receive your first ever fucking in front of the group and then your will have your first gangbang. How good does that sound?”.
OMG that sounds amazing and what I’ve dreamt of for months but absolutely terrifying at the same time. All those lengths of cock up my ass! I’m a bit confused about the poker and draft part of the night though which you messy realise as you continue. “We have the odd poker game but tonight is a bit different. We’re playing for cash but the position they end up in is also their draft pick number.”
I must still look really confused as you continue. “In the NFL, another sport we love, the teams take turns picking the best players and will make offers and trades to get the best draft number. In our case the guys will make offers to each other to trade their number in the queue fucking you. It may be cash or other stuff they offer to get as high up the list as they can. Should be a fun night and of course you’ll be on hand giving out blowjobs all night long and supplying us with a constant beer feed. I don’t expect to see any empty glasses! |
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Jessica and I go upstairs to one of your spare rooms where she gets me ready. She is told to go heavy with the makeup to make me look really slutty and pulls my hair into two braided pigtails, “the lads love them” she tells me. Finally I pull on my octoberfest outfit included the thigh high suspenders (with my pretty white thong on) and the patent high heels. I look in the mirror and simply don’t recognise myself, I look like a beautiful woman!
We go back downstairs and I kneel before you in the living room whilst Jessica sets up the poker table. The door bell rings and it is our first guest. “Go welcome them in then, no blowjobs you dirty slut”. I do as I’m told and welcome in the first guest, taking his coat and shoes before guiding him through to the front room where I supply him with a cold beer. The door bell rings another 13 times until the full compliment is here; just the 15 of you!
I am instructed to kneel in the centre of the room before getting into the downward dog position showing off my ass to everyone. “Us lads have decided that when you’re dressed up and looking as fantastically feminine as you do now that you deserve a female name. We have decided upon Chloe. Just to remind us of that later when we’re fucking you we’ve got a little present”. You pull up my dress, showing my whole bottom half to everyone before carefully yet firmly sticking another tramp stamp on me. This one simply has the name Chloe with some decoration around it.
Next time told to stand up and remove my thong before handing them to you. “That plug you’ve been carrying for a few weeks now is a large one but you need bigger”. You pull out a huge plug and show the whole room. The plug I have in already is firmly pulled out and you start the process of fitting the huge plug. It really is a struggle and takes a lot of pressure, lube and heckling until the plug pops firmly into place. I feel so incredibly full already and can’t wait for it to be removed!
“Right then guys let’s get started on our poker night. Remember you’re playing for cash and position in the fucking train that’s coming up so you want to do well!”. The next 2 hours for me is spent either under the table sucking every single one of you one by one or delivering beer to the table ensuring no one runs dry. It is an exhausting couple of hours but we finally reach the last 2. It is yourself and the guy with the monster cock.
Your cards are dealt and your lack of a poker face really shows with you struggling to hold back a smirk. You clearly hold some excellent cards but unfortunately the monster calls you out until you reach your limit. He still has a few hundred to go before his limit so you loudly announce. “Ok how about we both go all in. Obviously I don’t have the same amount of cash as you so how about I throw in Chloe’s anal virginity too”. I’m both shocked and horrified. Shocked firstly that you’d offer me up as a prize and secondly that there is a chance that my first cock will be the monster cock who will surely split me in two!
The monster calls your bluff and flips his cards. The shock is across your face, your fantastic hand has lost and with it my chance of losing my anal virginity with you! |
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“Pass me your lead Chloe”. I sit still staring at you in shock. *slap*. “I said pass me your lead bitch”. The slap wakes me out of my shock and I pass my lead to the monster who tugs on it sharply pulling me to his heel. He walks/drags me through to the other room where a fucking/spanking bench has been setup in the middle of the room whilst the game has been taking place. The only difference with this one is there are two scaffold poles which go vertically either side of where my head will go. The monster sees me looking quizzically and answers for me “that’s for me to hold onto to help get really really deep!”.
There are 15 seats in a circle around the bench but the monster points to you and says I want you in this seat. The seat he points to is directly in front of where my face will be. You take a seat looking very annoyed but there’s nothing you can do about it now.
The monster stands in the middle of the room and has me remove his jeans and boxers springing out his semi hard cock which is already enormous. Certainly fair bigger than I can handle. He makes me lick and caress his cock with both my hands due to the size. “Tell your Dom all about my cock and what it’s about to do to you”. In between licks I tell you how hard it is, how I can’t wrap my hand around it fully, how even with two hands I can’t cover the full length. I tell you how it’s going to split my little virgin hole which he has taken all this time to train in half and that I may not be useable afterwards.
The monster lies down on the floor right in front of you and beckons me to him. I crawl to him. He passes me the lube and tells me to get both of us ready. I lube myself first before turning attention to his rock hard length lathering it with as much lube as I possibly can. “I want you to straddle me and impale yourself slowly”. I do as I’m told. I position the monsters cock at my hole and start to lower myself down. Straight away I feel the resistance even with gallons of lube and simply can’t get even the head in. The monster sees this and tells me to stop turning to you and says “you can see this will destroy her. Want to make me a deal and you can have her virginity again?”.
You just look blankly so the monster shrugs, pushes me aside and grabs my lead again. He walks me to the bench and makes me climb on board. He straps me down by the ankles, around the thighs and around the waist. My hands are cuffed to the legs of the fucking frame so I can’t move.
“Now I can dictate the pressure and speed of the fucking. We’ll get you opened don’t worry about that”. The monster stands behind me and spanks me hard making me cry out. I’m begging you to make a deal, “please sir, make any deal with him”. The monster chuckles, grabs a gag and stuffs it in my mouth. “Well we know what she wants”. He repositions himself at my ass, grabs the vertical poles and starts pressing against my hole making me whimper. Before he can penetrate me you stand up and say “fine, what do you want?”.
You both stand there bargaining over me like a piece of meat whilst I’m strapped down in the fucking bench. Eventually a deal is struck. The monster confirms the details, “Ok we have a deal. She will visit me at least once a week to do as I say and will be at my beck and call anytime of the day. In addition to that you will pay for next years season ticket. Oh and another thing whilst I think of it. You did such a good job with this one and I want my own sissy fuck toy. You’re going to find me one, train her and then hand her over to me. Deal?”. Begrudgingly you shake his hand and I’m yours to break in again. You whisper in my ear “you better be worth it Chloe”.
You take the gag out of my mouth, “I love to hear my girls squeal”, before positioning yourself behind me. A hand is brought down hard on my ass cheek followed by 9 more on the one cheek and then 10 on the other for a total of 20 hard spanks, “that’s for making me have to make a deal with him!”.
My ass is already dripping from the amount of lube the monster applied but you take even more and finger it deep inside me starting with one finger, then 2, then 3. “Lads, I reckon she could take a full fist already”. I definitely couldn’t and shudder at the thought as 3 fingers was already stretching me. The anticipation is killing me as the eyes of 15+ people, some of whom are also filming, watch as you build up the tension. Jessica is on her knees now as well servicing everyone to keep them rock hard ready for me although with the sight in front of them I’m not sure she’s really needed.
I feel you grasp the vertical poles either side of me and as I try to look up at your hands I feel your head pushing against my tight asshole. You keep applying pressure slowly but firmly before my ass gives way and the first inch of you slides into me with an audible gasp/moan from me. “Now you really are a girl aren’t you!”. You don’t stop applying pressure, slowly inserting your full length into me inch by inch. The noise in the room builds with lots of heckling and comments but all I can concentrate on is your rock hard cock slowly filling me. With every inch I moan and squeak a little harder until I feel your stomach on my back and your balls against my body.
You stop and get everyone to take pictures with me fully impaled. Some getting close ups of my ass and some concentrating on my face which is now in ecstasy as finally having you deep inside of me. Then to my surprise you fully withdraw before plunging straight back in hard and fast. Wow that does make me moan and scream out in pleasure. I moan please Sir, give me more, harder, faster. After about 5 mins of this you slap my ass hard and shout out “will someone plug this sluts mouth with their cock”. There’s a surge and almost a fight to do so before a cock is plunged deep in my throat.
I’m spit roasted hard for another 5 mins before I feel your cock tensing up and then a very wet feeling as you cum, flooding my insides. Oh how I’ve longed for that! You whisper in my eye “now the night begins slut”. With this the next cock is rammed straight inside me. |
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"Fantastic story, I love it.
I wish that this had happened to me at the same age.
My cock is hard and leaking pre-cum just from reading the 1st installment  "
Omg i have to agree only was craving this kind of training and use by my early teens to be honest.
And ohhhh fuuuccckkkkk did i luv my first cum training. |
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