Because of a stupid and embarrassing financial situation I got myself into, I took a loan from a senior manager at work. At first the hundred bucks I paid him back each week wasn't too bad, but I began to struggle to pay him it back. Staying back on a Friday evening after work, the day I gave him the money, I explained my dilemma. Not even breaking to pause when I let him know my predicament, he said I could always pay him back in kind.
When I asked him what he meant he said "It's simple, you let me fuck you once a week, say Friday for instance and we'll call it one payment made". I instantly told him to fuck off and walked out. The following Monday he called me into his office and said the offer was still there, but if I didn't want to accept his offer, then to continue to make the payments each week.
I knew and he knew I couldn't afford to, so the same day at lunch time after thinking about what he'd said all morning, I approached him.
That Friday I waited like he did until everyone had gone home. In his office locking the door behind him, he dropped his trousers and boxers and I dropped down to see the fattest fucking cock you'll ever see. It isn't that long at seven inches, but it is extremely thick. Smiling down at me he said "Time to pay off this weeks debt".
For the first time in my life, I opened my mouth a let my boss slide his fat cock over my tongue. And surprisingly I took nearly all of it into my mouth. Over the next five minutes or so I sucked on his dick and found I was actually not only good at sucking cock, but also that I enjoyed it. But I wasn't in his office to pay him just with oral sex.
letting me stand up, he told me to strip. Stood naked in front of him sporting my own erection, he had me bend over his desk. Walking around his desk, he brought a new tube of anal lube and smeared my asshole with it. Asking me if I was sure I wanted to pay him back this way, I gritted my teeth and nodded.
Pain isn't the word for it. My asshole felt like it was being ripped in two and it hurt so much I thought I was going to pass out. But my boss just carried slowly thrusting his cock into my ass. I'd just got past that initial pain when I had a thought. Turning to him I asked him why he wasn't wearing condom. Grinning back at me he said "Because I hate fucking young guys assholes with my cock smothered in rubber". No sooner than he'd said what he did, he really began to fuck me. And everything changed.
The pain as quickly as it arrived, went. And was replaced by a growing feeling of anal joy. It was so nice, I told him to fuck me harder. Hearing my voice, he gripped my hair, yanked my head back and slammed his dick into me as hard as he could. The whole scenario I'd envisioned altered. Not once in my mind did I think I'd like being fucked, but there I was almost begging him to fuck me deeper. And without any warning my cock erupted beneath me, sending my cum all over his desk. With a renewed effort after hearing me cum, he himself began to moan loudly and then after one final deep thrust, his cock exploded up my ass sending his hot cum deep inside my body.
When he slid his cock out, I didn't want him to. Telling him how I felt, he said "No matter son, I'm going to be fucking every week from now on until you pay off what you owe me".
And for the next six months that's what we did every Friday in his office. I soon learned how I liked to be fucked to orgasm the hardest and strongest way I could. And that was mounting his cock as he sat on his leather office chair. My manager preferred to have me bent right over his desk, and most weeks fucked me that way. But occasionally he did fuck me missionary, and during those fucks we kissed like true gay lovers.
The loan was paid back nine months ago, but we still fuck every Friday. He now pays me a bonus each month on top of the wonderful fucking's he gives me. Nobody knows about the Friday evenings I stay back, or the weekends I stay over each month at his home. His wife enjoys golf and once a month plays over an entire weekend, staying overnight near to the golf course she's playing. It's not a rushed quickie when we're at his home and I get to experience a whole new side to his character there too. At work he plays and is the dominant person. He's still dominant at home, but our nights are more often than not more passionate in a loving sense.
I'm so glad now that I went to him for help, because it's helped me realize just who and what I am sexually.