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....

Dirty weekend part 3

So I had my boy's undivided attention. Bound to the chair, exposed and gagged. I forgot to mention in my last post about the other stop we made whilst shopping. Readers from the UK will have heard of Ann Summers; a high street shop specialising in racy knickers and sex toys. I find them incredibly cheap and nasty usually and prefer much better designed toys, but I had other plans for this stop. I found a vibrating cock ring made of a jelly like material which was inexpensive and smiled at my good fortune that they have started selling prostate massagers. I handed them to my boy and pointed him to the cash desk. He hesitated. I'm the only one who knows about his kinks and he knew there was no disguising what I would be using them for. To emphasise it I was going to the desk with him. I offered to let him off if he submitted to 10 cane strokes. So far I think the most he'd ever had was 5. Being the diligent boy that he is he confronted his embarrassment head on and completed the purchase. I wished the cashier had made at least one little comment to increase the torment, but sadly they were the epitome of discretion.

I'm sure he was thinking of our shopping trip as I opened the bag and got out the cock ring. Turning on the little vibrating bullet I ran it down his engorged cock and rather enjoyed his moaning and attempts to wriggle free. His cock twitched and strained until I stopped suddenly. It was nowhere near time for him to cum.

I busied myself in the bathroom fixing my makeup and refreshing my perfume for a short while. On returning his cock was much reduced in turgor but his eyes very much betraying his lust. As I changed from my day dress (a black linen sun dress with leopard print belt that nipped neatly in at the waist) into my black silk dressing gown on full view of him. I wanted him to see clearly that I was naked underneath and he couldn't even move a hand. Of course he had gone hard again, so fully erect that it pressed against his belly. Clear fluid dripping from the head and enticing writhing as soon as I touched the tip. I slipped the jelly ring over him so it sat at the base of his shaft. Waiting.

I unlocked his gag and removed it momentarily. I asked him how many days he had been locked for. It was a question he couldn't answer correctly as I was being unfair. He had been chaste for 29 days under lock up, but I last removed the cage 10 days prior to tease him at great length. He answered "29, Miss" and I smiled. I told him he was incorrect. The score was now 2.

I never tell him the punishment but he always knows the score. He knows not to argue as I have been known to double it if challenged. I was saving this up for later.

I unchained his legs and told him to stand. Stand still! I switched on the vibrating bullet and sat on the edge of the bed. He was struggling but managing not to move his feet. I knew vibration is never enough to make him cum but it will arouse him strongly. His hips kept trying to pull away but the bullet was firmly strapped to the base of his shaft.

Once he had wriggled enough for me, and sadly not given me excuse for another penalty, I turned the vibe off and removed the ring. "Thank you, Miss". He is always so good at remaining silent even when not gagged and I had almost forgotten that I hadn't replaced it.

It would have to stay out for what I planned next...