Charles is someone who I normally wouldn't have anything to do with. I might say hello or politely wave my hand towards him as he passed me on a fairway, or around the clubhouse. But his financial and social levels are not what I operated around.
However that hasn't stopped me from taking his large thick cock up my arsehole, twice a week for the past eighteen months.
He's a very wealthy man who probably could afford to buy the club where I work as a Greensman. It was at the golf course we first met and had sex. He hurt his ankle, and I gave him and his golf equipment a lift back to the clubhouse.
Basically on the way back, it absolutely poured down and we took refuge under a very thick set of trees. I saw his huge cock bulge and he saw me looking. One question was asked, and I found myself sucking on a very long fat cock as Charles fucked my mouth. He came fairly quickly and I was literally forced to swallow his cum.
A couple of days later, I got a message in work thanking me for the help I'd given Charles. And was asked to go and see the club secretary. He handed me a very nice expensive bottle of whisky and a sealed envelope. Opening the envelope was a pair of executive tickets to football match, a hundred pounds in money and a small note. The note which I read outside, simply said "My home Thursday afternoon this week three o'clock, I know you finish at two, Charles". The club secretary smiled at me and made only one comment before I left to read the note "Charles will look after you, if you look after him".
Ten to three I knocked on the largest set of front doors I've ever seen. Charles opened the door and five minutes later I was naked and receiving Charles wonderful cock in my mouth again. He told me his wife was out playing bridge with some of the other lady golfers (But later told me the truth) Sucking on his cock for quite some considerable time, he got me to stand up and took my hand. Leading us up a very wide impressive stairway, we entered the largest bedroom I've ever been in. I'm not joking, it's as big as my whole flat and then some. (Or should I say the one I used to live in). Asking me to lay on the bed face down, I felt him pulling my arse cheeks apart and then felt his hot breath on my hole. Moments later his tongue was lapping at my arsehole and only for the second time in my life, I knew I was about to have anal sex.
In between tonguing my arsehole and then gently fingering it, Charles asked me if I was safe, if I was clean. He took a risk when I said I was, which I was, as he moved up my body and I felt his cock slowly, ever so slowly enter my rear fuck hole.
Unlike the first time I was fucked, it only hurt for a short time. The first time I had anal sex, it was in a parks toilets and I was fifteen. The man a much older man didn't take my feelings into account and basically fucked me for all he was worth. Thankfully with his sheer size, his cock wasn't that big and he only lasted about a minute, if that.
Charles moved further up on top of me sending his cock deeper up my arsehole. Turning my head towards him, he kissed me and I kissed him back. We fucked in that position still kissing for a long time. He didn't once raise the rhythm or force of how he fucked me and I and my arsehole eventually relaxed. He knew the moment it did and had us move around. Spooning me, Charles began to thrust into my arse much harder and with greater depth. Soon he was fucking me the way I liked to fuck my girlfriend, roughly and with real passion.
At the same time he was pounding into my arsehole, he occasionally kissed me and also pinched my nipples hard. The feeling of the three interactions, kissing, having my nipples played with and my arsehole so expertly fucked, had my cock twitching and without once having had it touched once since I entered his home, I came all over the duvet below us. Yet Charles just carried on fucking me.
Spinning us over, he lay on his back and told me to mount his cock. Facing him, I slid down and accepted his gorgeous cock back into my rear hole. It was my turn to do the work and I watched his face intently as I fucked him. Charles let me do all the fucking at first, then with my cock rising again he took hold of it, tossing me off as he began to thrust upwards. Grunting and groaning about needing to cum, I sank down hard once more and then felt his cock explode up my arse. And his cock just kept on pumping load after load deep into my bowels.
Moving me off of him, he gripped my arse cheek and pulled me up to his face. Forcing me downwards, my cock slipped into his mouth and I enjoyed the next ten minutes of a sixty one year old sucking on my dick. Telling him I was going to cum, not once did he try to get me to pull out. Sucking even harder, I came and Charles sucked down and swallowed the lot.
We lay next to each other panting for minute or two, before Charles asked me if I'd like to make our first meeting a regular thing. I must have looked a bit doubtful, but he said "Don't worry the club secretary has guaranteed me, you'll get the appropriate hours to visit me each week, but only if you want".
The following week, the secretary walked into the area where we keep the machinery. Then told me, Charles and his wife had made a significant beneficiary payment to the club. He then said "Finish early today and say thank you for the club if you like".
I've now been saying thank you for over eighteen months. And enjoying Charles cock twice a week, every week, deep up my arsehole.
Knowing what I do now, I know his much younger wife understands Charles needs, and also has needs of her own. Needs I'm lead to believe the forty two year old club secretary takes care of.