The first time a guy fucked my arsehole, I was seventeen. My flat mate had done a runner and I wanted to stay in the flat. The landlord who was an older man gave me a ultimatum. Pay him the rent money (I didn't earn enough), leave the flat (I hated my mums new boyfriend) or once or twice a week, let him unload his cum in my mouth and pay only a fraction of the rent. The next day after the ultimatum I sucked on my first cock and allowed the fifty something year old, to cum all over my tongue.
The following night he called round and gave me another option. Let him fuck me as well as sucking his dick and he'd let me live in the flat rent free for however long I allowed him to fuck me. The weekend after he stayed for two hours. In those two hours I sucked his cock, had him lick and tongue my arsehole and then I took his relatively small but thick cock up my arsehole. It hurt so much at first, but I wanted the flat and the free rent. So I gritted my teeth and let him get on with fucking my arse. After ten minutes my arse just kind of gave way and he began to fuck me much harder and faster. Five minutes afterwards with my legs on his shoulders as I lay on my back, I ejaculated all over myself, closely followed by him shooting his cum deep inside my arse. Twice more over the next hour and a half he fucked me. Both times he fucked me in different positions and both times I enjoyed being fucked more than the last time.
It became a twice weekly thing and I soon found and worked out, it was when his wife was at her gym classes. The deal changed when I found out he was married. Not only did I get to stay rent free, I also began to get an allowance, which I saved.
I moved out eighteen months later with enough money to sign for a much nicer flat. I'd been promoted at work and my life was definitely looking up. I'd also began to date a stunning looking girl. However it wasn't the end of my anal drilling's. That's because to get the promotion, I'd given up my arse to a gay company director. He loved younger guys and I fitted his sexual brief. Every Friday lunchtime we'd go over to his private weekday flat, rather than eat lunch. He'd have me perform all sorts of gay sex acts with him and then before heading back, he'd fuck the shit out of me, always in his huge walk in shower and always very forcefully.
Life, especially when I started my own business, became a series of gay liaisons after that. With a series of girls taking my fancy too. I married one five years ago and we live a good life together. I love fucking her a lot and get great satisfaction from our relationship in every way (She is a dirty bitch in and out of the bedroom). But every now and then I seek out older men to annihilate my arsehole. Each one now, is somebody I know who will fuck me as hard and as deep as I like it. And each one has to be well endowed.