I’m not using my real name here and I have no publicly visible photos. With that anonymity in place, I will tell you the story of my nine-year relationship with my houseboy. The names and places have been changed. But the rest of the story is told exactly as it happened.
I had recently turned 50 years old. Most of my life had been focused on my career but I had dated and worked towards having a long-term committed relationship all of my adult life. It never really happened. I had been in a few 2-3 year situations but things would fall apart for one reason or another.
While reflecting on this I decided that if that relationship I wanted hadn’t happened by now, it probably was not in the cards for me and maybe I should consider a different path. I decided to lower my aspirations and shoot instead for a relationship that is a little more transactional, one that served my physical and practical needs, if not all of my emotional needs.
I figured a houseboy situation might work. I could find a sweet and genuine young man who had made a few bad choices in life and found himself in need of a safe port from the demands of life, and someone who could benefit from mentorship and eventually find his way. In exchange, I would have some companionship, help around the house and satisfaction of my physical needs.
All of these lofty thoughts were boiled down to a single line number 37 on my todo list as;
• Find someone to suck my dick
This comes back into the story later….
I found Santino on Houseboy.com. He was 26 years old, living in a houseboy situation with an older couple half-way across the country. He was unhappy there for a number of reasonable but not immediately dangerous reasons and he was looking to get out. Santino had come to the US under a student visa. He had flunked out of his first year of college and living in the shadows unable to work since his visa had expired and he was now in the country illegally.
I had flunked out of collage also, but then picked myself up and eventually worked my way up to a Senior Vice President position in a publicly traded tech firm. So I believe in the ability to turn your life around.
I chatted with Santino for several weeks. He was sweet, self-deprecating, and had a genuine and warm personality. After getting to know each other, we decided to have him come out for a week and see how things go.
Santino never asked me for a cent. He took a 3-day bus trip to see me and paid for it himself. This served as a strong indication that he was legit and not looking to pull a scam.
We had a great time. I got the impression that Santino was willing to put into the relationship as much as he was looking to get out of it and wasn’t expecting a free ride. He is also a natural born cock sucker who has loved to taste and swallow a man’s seed ever since a friend of his mom fed him cock when he was 8 years old.
Santino moved in and everything was perfect in the beginning. But of-course everyone is on their best behavior at first before things settle down to reality after the first few months. Santino greeted me with a cocktail every day when I arrived home from work and obediently sucked me off while I relaxed in front of the TV.
The normal routine that would come later was fine. Sex was good and mutually enjoyed. Santino started becoming lazy though and ended up doing about 10% of what he had agreed to. I held him accountable to pick up his part of the deal, and he would get back on track after a serious conversation.
This is probably a constant feature of every houseboy relationship. There is a reason someone is a houseboy instead of being in a successful professional career. The employer has to be pragmatic about this and maintain a careful balance to be tolerant and accepting of the reality that his houseboy is going to come with some issues. At the same time, you have to be firm enough to maintain accountability.
This is what we did. For years, things would slowly decay to Santino goofing off entirely, we would have a big conversation about it. He would get back on track for a good while before things started to decay again. This became such a constant in our lives that we invented a name for it. We called it “The loop”.
Santino was bright and needed a job to help him engage with the world and develop marketable skills. I didn’t want to see his potential wasted. But without a green card, he had no way to have legal employment. So, I started a home business he could work in.
We made and sold products on Amazon. The first week we sold four and made $48. It was fun. I worked on it night and weekends, and Santino worked on it full time.
Fast forward three years…. The garage business grew to $2.4 million revenue though profit was very minimal. We had eight employees and Santino was running import/export, sourcing, and manufacturing while I ran marketing and finance full time, after quitting my real-job.
Santino was flourishing though the loop was a constant factor. It always took getting to the point where we were going to end thing. This is the only thing that would wake him up and get him back to being responsible.
Our personal relationship had flourished despite the loop. We were very much in love and three years into the relationship, yup, I married the houseboy.
We had a great life, with travel, shared experiences, warmth, love, companionship, really everything you would want from a long-term relationship. It was the long-term companionship I had always previously been trying for. And ironically, I finally found it after having given up looking for it.
One day, Santino shared with me that he had stumbled across my todo list with the line item “Find someone to suck my dick”. We joked about how far we can come from that crude origin.
Over the years, the loop remained an intractable problem. Often, I had to relieve Santino of some of his duties because he just wouldn’t do the work. While he really wanted to be successful, he continued to struggle immensely with self-discipline.
Around our seventh year together the business started to fade. It became too difficult to make a profit on Amazon and it was time to shut down the business and do other stuff. I went back to my previous career. Santino, now with green card, was able to be employed. He looked for work, but not with any vigor.
Meanwhile, our togetherness slowly faded. I suppose this happens in any marriage after several years, but Santino’s struggle with self-discipline made it worse. He tended to spend more and more time alone, with his computer games and Reddit. The loop had spread to our relationship. He made several genuine attempts to get back in the groove but the loop was never to be defeated.
Eventually our relationship became like long-term roommates who care about each other from so much live lived together, yet having separate lives.
The relationship, no longer serving the needs of either party, had come to its natural end. We separated on good terms and he now has an apartment and looking for a job. He is 35 now and knows it’s time for him to stand up on his own two feet and put himself in a position where he can get by in life without being dependent on anyone else.
I don’t know if he will make it. I hope he does, I know he can. He is a stronger, better, more capable person than he was 9 years ago. I made a difference in his life as he has made in mine. We will always mean a lot to each other so long as one of us still lives. But now it’s time for me to think about what comes next for myself.
If you’re an employer reading this, I don’t know how common my experience was, my gut tells me this doesn’t happen more than one in a hundred times.
If you’re a houseboy reading this, maybe you are a genuine guy who sees this as ideal. If you’re a scammer looking for an easy mark though, just be aware I will see you coming a mile away. I knew who Santino was down inside and I chose him with open eyes. I will see who you are for better and worse with the same clarity of vision.
