Chapter 50

With a slight forward thrust, I nudged my tip against his hole. He shuddered at that first touch, and I felt him tense. Not really what I wanted, I actually needed him to relax and open up to me. I pressed forward again, slotting my cock in to the crack of his arse and then rubbing. He pushed back and I took that as a sign for me to get on with it and cut the foreplay. I steadied my dick with one hand and guided it gently in to his hole, it went in smoothly. But immediately, I felt his arsehole tighten and grip my cock, it was divine.

As I eased in fully, he groaned. ‘Ohhhh ... yes ... that’s good ... that’s ... uhhh nice.’ Holding his hips again, I set up a gentle rhythm, slowly in and slowly out, he felt wonderful. Giles continued to moan softly as I tenderly pumped his arse. I have never been a huge fan of condoms, but these were especially sensitive and allowed me to feel the full splendour of Giles’ arsehole.

I was transported on a wave of ecstasy, the sweet sensations growing and swelling up from my crotch. I tried to hold my orgasm back in the old tried and tested ways, but then I thought, what the hell? I decided to just go with the flow, so to speak. In just a minute or so, I was ready to cum, and I just let it happen. I spurted one load after another, filling the condom up with semen.

Giles seemed a little surprised that I had cum so quickly.

‘Have you cum?’

‘Uhhh ... yes ... it’s cum.’

‘Was it OK?’

I withdrew my softening cock from his awesome arse.

‘It was terrific ... thank you ... really nice.’

‘You were quite quick, you must have been really horny.’

‘I was actually, and you were the reason.’

‘Thanks, nice of you to say that.’

I pulled away from him and slipped the dangling rubber off my dick. Holding the full condom in my hand, I said, ‘May I?’

He didn’t know what I meant at first and then he realised, I meant his as well.

He pulled the rubber off without spilling any of the contents and handed it to me.

‘Thank you.’

I went in to the toilet and flushed them both down the loo. I didn’t use the waste bin, the poor chambermaids had enough to deal with without two spunk-filled rubbers that had been up blokes arses.

When I returned to the bedroom, Giles was already putting his dressing gown back on. He looked up as I, completely naked, approached him.

He smiled at me.’You really are very cute, Carlo, it was really nice, well worth the money. When I am back this way, I’ll give you a call.’

The mention of the money, after the deed, somehow made it seem sordid. It was sordid of course, but I had come to look on the whole arrangement as a special service. Payment seemed to cheapen it. But, much as I loved what I did, I really couldn’t do it for free. Once or twice here and there maybe, but basically, I was a sex worker, I made money, lots of it, from selling my body. It was a self-conflict I struggled with all the time. I was a businessman and a whore, not your usual bedfellows, so to speak.