His Strap-On Training: Seven Days to Obedience

I have always believed that anything worth doing is worth doing with a plan, which is how my boyfriend ended up enrolled in a formal strap-on training program with yours truly as headmistress, coach, and entire faculty. He signed up willingly. That is important. He practically begged to enroll. I just made it official.

It started because he got curious. We had been together a while, things were great, and one night after a particularly good round, he got this thoughtful look and asked me if I had ever thought about switching things up. I asked him what he meant, and he turned the most adorable shade of red and mumbled something about strap-ons. I laughed, kissed him, and told him that if he wanted training, he was going to get real training, not some rushed one-night experiment.

Day one was orientation. I sat him down on my couch, fully clothed, very businesslike, and laid out the syllabus. The program would run seven days. Each day had a lesson, a drill, and homework. He would address me properly during all training sessions. Complaining would add extra drills. Enthusiasm would earn rewards. He agreed to everything so fast I barely got the words out, which told me exactly how badly he wanted this.

Day two was anatomy and preparation, which is the unsexy part that makes everything else work. I taught him about relaxing, breathing, and why rushing is the enemy. The drill was simple: he wore a small plug while we watched a movie, and every time he fidgeted I paused the film until he settled. By the end of the night he was squirming for entirely different reasons, and I sent him home with homework to practice on his own. He texted me at midnight to say he couldn't sleep. I told him that was excellent progress.

Day three was rhythm. This was his first real session with the harness, and I kept it slow and instructional, narrating everything like a very dirty professor. I showed him the difference between shallow teasing and deep steady strokes, and I made him tell me which he preferred at every stage. He could barely form sentences by the end. His homework was to write me a paragraph describing his favorite part. He wrote three pages. I gave him extra credit.

Day four I introduced positions, because a well-trained boy should be versatile. On his back with his legs over my shoulders. On all fours. On his side while I spooned up behind him and took him slow and deep. Each one got a grade, and I was a tough grader. He failed the first attempt at the new angle and had to repeat the drill until he got it right. He did not mind repeating it. Not even a little.

Day five was the hard one, literally and figuratively: edging and control. I brought him right to the edge with the strap-on, deep and perfect, and then stopped. Made him breathe. Made him wait. Did it again. And again. Four times I took him to the brink and pulled him back, and by the fourth round he was actually whimpering, begging me to let him finish, promising to be good forever. I let him come on the fifth, untouched, just from being taken so precisely, and he shook for a full minute afterward.

Day six was the practical exam. No instructions, no coaching. He had to show me everything he had learned: how to present himself, how to ask, how to take it, how to thank me after. He passed with flying colors. I rewarded him by letting him return the favor, and let me tell you, a week of being denied and trained had made him the most attentive lover of my life. He worshipped me like I was the entire syllabus and the final grade.

Day seven was graduation, and I made it ceremonial. Candlelight, my favorite playlist, the works. I took him slow and deep and told him how proud I was, and he came harder than he had all week, and then held me afterward like I was the best thing that had ever happened to him. Then I handed him his diploma, which was a note I had written that morning, and it said he was officially my favorite student and that refresher courses would be scheduled regularly.

Last month he requested a refresher all on his own, completely unprompted, which tells me the program worked exactly as designed. We skipped straight to the advanced material, and he performed flawlessly. I am considering adding an honors track, but only for students who truly apply themselves. He has already started studying.

That was months ago, and I am happy to report that the training stuck. He still asks permission. He still says please. And every now and then, when he has been especially good, I announce a pop quiz. He has never once complained about homework.