Tonight Mistress had a lovely orgasm on my tongue, after which she got me nice and hard before mounting my cock. She was wearing a vest top again, and like I described before she lifted it up to expose her bra. Needless to say I eagerly begged to see her gorgeous breasts and Mistress pulled her bra down to allow me to cup and suck her tits as she rode me.
Eventually Mistress dismounted and knelt beside me stroking my slippery, wet cock. After some stroking I told Mistress that I was close and she stopped, telling me that she wasn’t going to let me cum today. But then she changed her mind and stroked me some more, asking if I was really close. She loosened her grip and it became clear that the only orgasm I was getting today was going to be ruined, if that.
Mistress gave me a few more proper strokes before loosening her grip again and slowly easing me over the edge. I think it was definitely the most frustrating ruined orgasm I’ve had yet. I was trying so hard to cum, and it felt like the pressure was so great that even Mistress’s delicate stroking would result in an initial huge spurt of cum, but it didn’t at all. Mistress continued her feather light strokes throughout but my cock merely leaked a huge puddle of cum without a single ‘spurt’ in sight. It was a perfectly ruined orgasm, and afterwards Mistress fed me quite a bit of cum from her fingers.
So now I’ve had four ruined orgasms and two proper orgasms to Mistress’s twenty eight proper orgasms since the start of this chastity year. It definitely seems like there’s some major progress being made here now. 🙂