I remember a moment in the past with the starkest clarity. It was back in the days when I had a maid. He was also the first boy I fucked. I’d never really wanted a boy in that manner before. We had a similar sense of humour and I was jealous of his legs in stockings. He was significantly taller and bigger than me, could easily overpower me if he so chose. But we both knew he wouldn’t dare!
One day after we had been out buying lingerie I was in the mood to remind him of our agreed dynamic. He was beginning to get too comfortable and despite his love of female underwear he was still very much a bloke in public. He was wearing holdups under his trousers and one of them was falling down as he hadn’t paid enough attention to putting them on. The whole taxi ride home he complained about feeling uncomfortable and wishing he was more of a vanilla boy. I laughed and told him to stop being such a baby, to which he sulked.
As soon as we got inside and the door closed behind us, I took my panties off, rubbed the wet fabric in his face and shoved them in his mouth. I kept my dress on and told him to remove his clothes.
Then I took both his hands and attached them to the arms of the chair. I wonder what was going through his mind when I left the room and returned with the strap-on he bought for my birthday. I’m sure he thought I’d forgotten about it as I hadn’t mentioned it since, which was quite a few months ago.
I slap the dildo around his face and stroke his cheek with it.
‘Did you think I’d forgotten about this?’
‘No Miss’ He replied ‘I know you’ll use it when you decide to and it will be your choice’.
‘Thats right maid, and instead of sulking the whole way home perhaps you should have asked what you will be making us for dinner and what I’d like to drink. Since you failed on both counts I’ll have the rest of the wine and you will have my nectar, its not really a punishment for you though is it?’
‘No, Miss Eve, I enjoy tasting anything thing from you’.
‘How can I resist such a sweet statement. I slide the length of the toy between my legs until its nice and wet then remove the panties from his mouth and place them around his neck like a collar.
With that, he licks from the base to the tip and I almost wish I was wearing it, given his dedication to the task.
I rub the tip around his lips and he chases it with his tongue.
Slowly I push it into his mouth. I can tell he wants to redeem himself and would have allowed me to take him on the spot if I wanted to. But thats for another day.
‘No dressing up for you tonight’
I can see the disappointment in his eyes, but the boys got to learn.