She has been keeping me in chastity pretty much all of the time now. I was released from chastity Sunday night, but then spent the night chained to the bed by my balls. The ball stretcher does not fit on when I am locked in the chastity device we use.
When I get home from work, I am stripped down, told to go clean up and clean myself out, then I am shackled and kept naked for the night.
We have also restarted our ritual of me getting anally fisted or fucked at least once a day.
Last Monday, she was extra hard on me with the strapon, she fucked me until she came, and she had milked me. Usually I do not get milked from the strapon, but she was extra vigorous. When she was finished I was curled up in a ball on the bed. she left the room for a bit, then came back.
I felt something pushing into my ass and I figured it was the bigger strapon, but when the fist bump popped in and I felt the second bump, I realised it was something else. That plug is big, even by my standards, and no one else has pushed it into me before. It even takes me time to work it in usually. She was not forgiving, and just shoved it into me. She spanked and paddled me for a bit before deciding she wanted oral pleasures.
She pushed me off of the bed, and grabbed my head and shoved it into her crotch. I brought her off to a couple of wild orgasms, and then she pulled me back onto the bed.
She yanked the plug out of my ass, and shoved her fist into me and gave me a very rough fisting. It was at that point I orgasmed and came. In chastity, from anal stimulation.
My first orgasm from anal stimulation.
I have been milked many many times which I find painfully pleasurable. She loves to milk me. So I really do get milked a lot.
This time was way different. A whole body orgasm that lasted a while.
She was so happy with what she had done that the next day she wanted to do it again to find out which part of the whole thing brought me to the orgasm vs. just getting milked.
When I got home, I was stripped, showered, cleaned out and put back in shackles. She had written down notes from the night before of what she did so she could try to repeat it. I said that I believed it was the abject sexual objectification, how she used me for her pleasure, how she caused me pain with her pleasure.
THis time, we started out with a sensual strapon fucking, I am on my back, and she lays on top of me and fucks me, face to face, and we touch and fondle and caress each other while we fuck. She orgasmed from that a couple of times, and on the second orgasm, she caused me to convulse and milked me.
Then like a light switched on, she pulls out of me, flips me over and proceeds to pound on me mercilessly with the strapon. This time she had the big plug ready, and pulls out of my ass with the strapon, and shoves the plug into me. She took her hitachi and put it on the plug, then ground her crotch on the hitachi getting herself off again.
She pushes me off of the bed again, lays down with her legs hanging over the side and I bury my face in her crotch. She grabs my head and directs the pressure and placement of my tongue, like I am just another toy for her orgasms.
She builds up to a very large orgasm and when she comes she crushes my head between her legs. At this point I come and come hard, with an electrifying orgasm. It was like getting hit by lightening and having an epileptic seizure all at the same time. I came so hard I pushed the huge plug out of my ass. She said I was shaking hard, my eyes rolled back into my head and I was not breathing. I squirted a huge load of come onto the floor. More come than I have ejaculated in a very long time.
When she saw that I pushed the plug out of my ass, she pulled me up onto the bed by my collar and shoved her fist into my ass, deep, past her elbow and almost to her shoulder. she gave me a vigorous fisting and milked me a very painful milking.
That, is the most incredible orgasm I have ever had.