Dirty Weekend part 4

So there he was, standing there, going nowhere. I told him to kneel at the end of the bed, which he was quick to do, as I took up a position in front of him. Given the luxurious height of the bed his mouth was at just the right height to pull his head between my legs and have him pleasure me for a while. Knowing that he likes the feeling of being smothered I was careful to make sure I held him hard! (I'm sure sometimes he regrets letting little hints slip). He was eager to please, which he always is, and it wasn't long before I had my first orgasm of the day. I let him rest a short while with his head on my thigh whilst I thought of what to do to him next.

Using the chaise longue at the side of the room (which incidentally was an absolutely awful colour of grey!) I got him to lie over the bottom end so that he was supported under his belly. I removed his armbinder to give his shoulders a rest, but made sure that he was securely fastened to the feet of the chaise meantime. This left him on all fours with his bottom enticingly exposed.

I got the prostate massager that I had sent him to pay for earlier and made sure it was well lubricated. My boy is reasonably new to anal play and I have been rather enjoying training him up to be ready for my strap-on. The massager was slim and went in easily although I do have to say I didn't make too much of the position of the switch for the vibrator which was in an awkward to reach place and becomes very slippy in the presence of lube. I persevered however and I watched him do the shuffle of trying to get away from the probe but then retreating back onto it when I told him to stop wriggling. In all honesty, I like the wriggling, but it's so much more fun watching him try to stop! I reached round to give his semi-hard cock and few strokes. He's still at that stage where anal play is somewhere between aversive and pleasurable, but he keeps trying and practicing for me. He knows I own him and he can't be keeping anything from me. If he truly decides that it's not pleasurable to him then I can always add it to the punishment list.

When I decided he had had enough I withdrew the massager, undid his bonds and prepared him for the most devilish thing of the day so far! We stopped, ordered room service and a bottle of wine and cuddled under the duvet to watch a movie! Oh the horror!!!!!

But that was just the first few hours. It was nowhere near bed time and there was always tomorrow too....