In Debt to Sir
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 started 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, and in my experience are often best left as fantasies, and certainly only engaged in with a trustworthy Sir.
The boy amused me. He was respectful and 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 judgment. Our connection was growing and mutual and developed 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 coffee. Before long, £3.80 was sent to me via an app. I sent him a picture of my coffee and 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, on 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 lunch time 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 it felt right to treat me in this way, it just felt right for both of us.
A couple of weeks later I was out for drinks at my club with some friends. I’m 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 all a bit of a pain having to get everyone to pay money, etc, and the usual issues of how to split the bill. My boy apologized 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 with our usual conversation and got into a routine together until he wrote and said he’d had something to ask me and that he was a bit scared to ask. I reassured him that as my boy, he could ask whatever he wanted without judgment 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 in my day. He really enjoyed the connection with me as he went about his day. The amounts in themselves were small, but consistent and this built our bond closer and closer each week.
Natural Progression
From this early and natural start, things progressed. I’d asked him if he was ok with my level of spend and whether he was managing financially. He admitted to me he was hopeless with money, and that everything was fine. As our relationship had developed, I’d come 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 set up some pension savings, ISA accounts, cancelled endless subscriptions and prioritised his credit card payments. My boy dutifully followed my instructions and I chose his investment strategies etc. 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 had been stressing him out. He knew for years he needed to do something, but just couldn’t get to it.
Some weeks later he asked if I would take over management of all his money. He said it felt quite 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’d manage everything else. I’d have access to all accounts and able to change the passwords so he had no access apart from the debit card with his weekly 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 gifts he wanted to buy me. From new shoes, to the expensive suits I enjoy wearing, he began paying for them for me. 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 £1000 which I’d 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 and tie and beautiful shoes and it gave him purpose knowing that he’d provided it for me.
Deeper and Deeper
About a year into our relationship his car lease came up for renewal and decisions had to be made on a replacement. I’m not one for spending money on new cars, so determined that a 5yo 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 and he said it felt right for him not to have a new car. We chatted more deeply about this, and he explained spending on me gave him so much more pleasure than spending on himself. He was saying that he feels guilty the size of his allowance and wants to reduce it. He said that he wants to live like a monk, so that he can spend more on his Sir. We explored this thought pattern some more until such time 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 he sent to me directly as he says his sacrifice is for my luxury. In return I sent him pictures of the luxury coffee maker, new TV etc. 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 really unnecessary. I found him a room to rent on Spare Room, and had him move in there while he secured tenants for his home. My boy had gone from living in his own 3 bed new build with a new car on the driveway, to living in a share house with a 5 year old Polo on the driveway and couldn’t be happier.
With his income and bonuses, together with his reduced consumption, money was piling up in his accounts. I knew this of course, but he didn’t. Although he’d been spending on me, and I’d enjoyed my expensive gifts, I’d not in any way abused his trust. His credit cards were all paid off, his ISA accounts 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 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 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 £10k completely free and open to spend. He was confused. He didn’t see the gift in giving him 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 that 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
