The Spinster's Exploits

As said – I have a new lover who is an ex into cross-dressing; and is on an interesting  excursion from vanilla monogamy into bi-sexual TV territory and swinging. Having confirmed the chemistry, and both passed the compatibility test we arranged to meet again.  He is also quite spiritual and a crystal lover. Despite his height, there is something quite elfish about him. And so I met my Spiritual Elf again – this time with some of his hidden wardrobe!

After a pleasant meal out, we got back to mine for a cuppa and chat when magician-like he revealed a very cute and very short little black and white, pleated, plaid skirt and stockings and suspenders under his jeans!

So I reaffirmed that he’d like to do a Headmistress/schoolgirl roleplay in reality and discussed consent and safewords, and he was eager to go.

I got into role, told him off for his bad behaviour and vaping and ordered him across my lap and attacked him with my hairbrush, firstly over his barely-there skirt, then over his silky knickers which I attacked for their inappropriateness, then I finally attacked his now red bare bottom. And I kept telling him how naughty he was, and got him to agree to deserving the spanking, the seriousness of his misdemeanours, and what should happen next due to said transgressions.

When spanking his bare bottom quite hard with my hairbrush I commented on his penis and its unsuitability and called him a naughty girl/boy. He took the spanking well and agreed to be taken upstairs for further punishment on my bed. I gave him some further whacks with ruler and paddle and added a few stripes with my easiest-to-use cane!

I then decided the headmistress needed rewarding, for her exhausting efforts and he happily provided suitable breast worship while I praised him as my good boy/girl and happily vibed myself to a delightful orgasm.

Not sure when I can award myself that capital D, but I am really enjoying bossiness, beatings, and – with my lovely “Established lover-etc…” – bondage-lite, pinwheel play and nipple clamps! The proof is a very damp fanny after my “bossiness” and an absolute delight on inflicting measured amounts of pain and submission – hmmm…