In Debt to Sir
This is a true story, originally published by me on Reddit.
It all started with a DM on my Twitter feed. This was not an unusual occurrence, as I get many messages from Sirs and boys who enjoy my popular D/s account. It began in the usual way with a, “Hi Sir, I really like your account,” etc. We began chatting and I learned that he was a 35-year-old IT guy—quiet and shy—with a real interest in financial domination and blackmail. These are both fun fantasies, but the reality can often be devastating for a boy if not handled in the right way; in my experience, they are often best left as fantasies and certainly only engaged in with a trustworthy Sir.
The boy amused me. He was respectful, considered, and clearly intelligent, which always attracts me. It felt to me that our conversations became his safe space, where he could express his innermost thoughts and desires without judgement. Our connection grew, becoming mutual and developing naturally over several weeks.
Started Slowly
One morning, we were chatting as I sat at my local coffee shop having my morning coffee when he asked if he could buy me another. Before long, £3.80 was sent to me via an app. I sent him a picture of my coffee and my surroundings, and he thanked me for allowing him to pay. Our conversations continued in the usual way until the next morning, when I saw another £3.80 had arrived on the app together with a message: “For your morning coffee, Sir.” Again, upon ordering my coffee, I sent him a picture, and life continued as normal between us.
This continued for a few days until, one day, I was in London for business. At lunchtime, I received a message saying, “I’d really like to buy your lunch today, Sir.” I sent him a picture of my Pret sandwich and coffee and, almost immediately, funds were sent. Our new routine continued, with my coffees and lunches being reimbursed by my boy. He told me he loved doing it and that it felt right to treat me in this way; it simply felt right for both of us.
A couple of weeks later, I was out for drinks at my club with some friends. I am a member, so the bill came to me as the host. My friends all reimbursed me, but I was complaining later in my chat with my boy that it was a bit of a pain having to get everyone to pay, along with the usual issues of how to split the bill. My boy apologised that I had to deal with that situation and immediately sent me reimbursement for the entire bill. He said that he didn’t go out much, so it felt right that he should pay for his Sir’s enjoyment with his friends.
We progressed in this way, maintaining our usual conversation and falling into a routine, until he wrote to say he had something to ask and that he was a bit scared to ask it. I reassured him that, as my boy, he could ask whatever he wanted without judgement or sanction.
“Sir, would you do me the honour of having my credit card on your Apple Wallet so you can more easily charge your daily necessities to me?”
Our relationship became more free-flowing from here. He enjoyed the daily notifications on his phone as I bought my coffee, lunch, or various other items during my day. He truly enjoyed the connection with me as he went about his business. The amounts in themselves were small but consistent, and this built our bond closer each week.
Natural Progression
From this early and natural start, things progressed. I asked him if he was okay with my level of spend and whether he was managing financially. He admitted to me that he was hopeless with money, but that everything was fine. As our relationship developed, I came to play a more instructive role in his life generally and required him to send me a statement of his assets, liabilities, income, and expenses. I instructed him to write everything down and send it to me.
After a bit of back-and-forth, we were confident everything had been accounted for. My review suggested that he was right: he was rubbish at money management. He had a good income but had no idea where his money went. I set him up with a financial plan. We established some pension savings and ISA accounts, cancelled endless subscriptions, and prioritised his credit card payments. My boy dutifully followed my instructions, and I chose his investment strategies. He was so thankful for my help and couldn’t stop saying what a relief it was to have everything sorted. Money management comes easily to me, yet it had been stressing him out for years. He knew he needed to do something but just couldn’t get to it.
Some weeks later, he asked if I would take over the management of all his money. He said it felt natural and right when I was dealing with things, and that he’d really like me to do it permanently. I asked exactly what he had in mind. He said he knew he couldn’t be trusted with his money; he wanted a weekly allowance, and I would manage everything else. I would have access to all accounts and be able to change the passwords so he had no access apart from the debit card for his allowance. I love control and find it the best aphrodisiac so, after some discussion, I agreed. Account access was set up for me on everything, and we settled upon a weekly allowance to meet his needs. We both enjoyed the level of control I had over him, and we continued in this vein.
As our relationship deepened, so too did the size of the gifts he wanted to buy me. From new shoes to the expensive suits I enjoy wearing, he began paying for them. It was always at his request, and always when he felt he wanted to. The most expensive gift to date had been a new suit for £1,000, which I had bought anyway and he wanted to reimburse me for. A quick transfer from his savings account and it was done. He said he loved seeing me in my suit, tie, and beautiful shoes, and it gave him purpose knowing that he had provided them for me.
Deeper and Deeper
About a year into our relationship, his car lease came up for renewal and decisions had to be made regarding a replacement. I’m not one for spending money on new cars, so I determined that a five-year-old VW Polo would suit his needs. I found one at a dealer, paid for it, and sent him to collect it. He was so happy and thankful; he said it felt right for him not to have a new car.
We chatted more deeply about this, and he explained that spending on me gave him so much more pleasure than spending on himself. He said he felt guilty about the size of his allowance and wanted to reduce it. He told me he wanted to live like a monk so that he could spend more on his Sir. We explored this thought pattern further until I was happy that this was what he needed to feel complete. I set him the task of selling everything that was superfluous to his new, monk-like life: technology, clothes, bikes, and all the toys of his previous existence. We left him with suitable and functional essentials, but all luxuries were gone. All the funds raised were sent to me directly, as he says his sacrifice is for my luxury. In return, I sent him pictures of the luxury coffee maker and new TV that I bought for myself. He was so happy.
In time, we determined that his biggest expense was his mortgage and that the space he enjoyed for himself was unnecessary. I found him a room to rent on SpareRoom and had him move in there while he secured tenants for his home. My boy had gone from living in his own three-bedroom new-build with a new car on the driveway, to living in a shared house with a five-year-old Polo, and he couldn’t be happier.
With his income and bonuses, combined with his reduced consumption, money was piling up in his accounts. I knew this, of course, but he didn’t. Although he had been spending on me and I had enjoyed my expensive gifts, I had not in any way abused his trust. His credit cards were all paid off, his ISA accounts were topped up, and I had doubled his mortgage payments. He was in a much better financial position and so much happier. He kept thanking me for being his Sir and telling me how happy it made him to sacrifice for me. He said he found a new purpose in life knowing that all he did was for me.
Life Transformed
Without all his toys and fancy technology, my boy had more spare time to fill. I set him up with a gym membership and a PT, and we got him into better shape. Each step on the journey we have together is about improving his lot in life. He now finds going to the gym natural and is motivated to show me the progress he is making. I’m very proud of how he has blossomed into an obedient boy—motivated and with purpose.
My Christmas present to him last year was handing him back his fully paid-off credit cards. His limit of £10,000 was completely free and open to spend. He was confused. He didn’t see the gift in being given spending money until I advised him that his job for the year was to max out his credit cards completely on me—to think deeply about what luxuries I need and how he wants to treat me. It’s June now, and the cards are maxed out. I love my new watch and, of course, my private club is so much more fun now that I don’t have to pay the membership. He loves the fact that he’s completely in debt for me.
It’s his birthday next month. His gift will be the instruction that he needs to get a second, part-time weekend job to pay the debt off. I know he’ll love it.
Let me know what you think. Would you like to be this boy?
