Two weeks, three days

She came to me with a small glass and the key to the lock. My instructions were to jerk off four times into the glass. I obeyed.

Later she came into the room, bound me with a restraint I had made some time ago with my face down, ass up. She got out one of her dildos and used the cum to lubricate it before and while she shoved it in my hole.

Now, I have played with plugs before, but this was the first time I had been "penetrated" per se. The experience wasn't entirely unpleasant, but my virgin ass burned for a while. If this were to become a common thing (which in this house, nothing is really common), I will certainly be in need of more stretching and training.

Honestly, the least pleasant part of the evening was her spanking. She used a hard rubber spatula that she likes because "it's pink, and says Love.".  Well, the only thing I loved about it was that she quit using it. The light slaps and taps she used were nice with just a little sting. But when she would put a little more arm into it, it would lay me flat on the bed.