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Slave tom Day 5 - Pleasure & Pain 05/23/11 Today, the Mistress and I decided to mix domestic discipline with the fun we’ve been enjoying in our BDSM dynamic. I agreed to her terms for total submission rather than the intermittent commitment I had shown before. I realized that both of our lives would shift significantly, meaning not everything would be pure enjoyment for slave tom (me).

Today I challenged the Mistress’s authority (a big error) by actually documenting my masturbation session. I knew this was a blunder and expected to face consequences. My reasoning for admitting my selfishness to her was that I knew it had to end and she would handle it. If only I had known exactly what actions she planned to take, I might have reconsidered.

The evening began pleasantly enough. We joked about the masturbation video I showed her and discussed how our relationship is evolving from role-play into daily submission. She asked if I was truly ready for this, and I said yes. Little did I know that my sincerity would be put to the test that night.

Mistress instructed me to retreat to my room between 9:00pm and 9:15pm. I got distracted by a basketball game and arrived at 9:20. She entered, handed me a glass of wine, and told me to undress completely. She laid a towel on the bed and had me lie down, allowing me to keep watching the game. At 9:40, she reminded me to use the bathroom and insert my butt-plug (which I did quickly as I was catching onto her emphasis on strict scheduling). I have a large but comfortable plug that fits well; it causes some initial discomfort when filling the cavity before becoming pleasurable.

I returned to bed. She came back in, poured me more wine, then guided me to her side of the bed for a deep muscle massage. Here I am thinking I’m about to be punished for masturbating, yet she is rewarding me instead. Honestly, I felt wonderful. As she rubbed my back, she said she understood why I needed to masturbate but was concerned it took time away from us and didn’t like that I was watching other women online. Her verdict: no sex with her (duration unspecified) and I must watch her masturbate while connected to another man on the internet. I wasn’t thrilled but accepted her logic and obeyed.

Next, she put on her favorite strap-on and pleasured me well with a 6-inch cock. Shortly after, she grabbed a large dildo and began thrusting it in and out of my rear. This marked the shift in the evening’s tone. She pushed it inside firmly, ordering me not to touch my own cock. I said I needed to release, but she insisted, “don’t touch.” It became quite torture-like, which she knew full well. To me, it felt like driving over a speed bump…a pleasant rise at first, but when repeated endlessly with no escape, it feels QUITE agonizing.

The Mistress then swapped in her massive 12-inch cock strap-on and fucked me hard yet nicely. Finally, I was allowed to climax! I ejaculated all over myself, ready for sleep. But Mistress wasn’t done. She took the mess from my chest and smeared it across my face, making me swallow some of it. It was truly revolting. “This is what you get for masturbating,” she said.

Once cleaned up, I found myself highly aroused (truly) and asked her to please sit on my cock—she refused, stating I couldn’t touch her. She did allow a brief lick at her breasts though.

To my slight surprise (I expected more action), she told me to remove the CB-3000 chastity device and place it back over my cock. I hadn’t worn this apparatus in well over a year, so putting it on again was disappointing. After locking my cock inside, she retrieved her canes and ordered me to bend over—I received at least 40 strokes for my masturbation offense. She then told me to go to bed—which I did happily.

Mistress woke me early the next morning (05/24/11) and changed the lock on my chastity device. She instructed me out of bed for more cane strokes—I wasn’t sure if this was discipline or punishment. Initially, I called my safe word because pain lingered from the previous night’s activities. This made Mistress both sad and angry. However, remembering my commitment to her, I got up to receive the caning—I realized the fun was fading rapidly.

I then went for breakfast and noticed a letter on the counter. Mistress requested that I clean my office and make my bed. She also needs me to order some clothes online during the day.

Mistress and I welcome community feedback and information sharing. We want to learn from each other and share knowledge with those interested. As two hardworking professionals, we are striving to elevate our relationship further.

So have we gotten the message now???:rolleyes::blink: