A Strange Friday Night

It was 7 pm on a Friday evening. I had just finished dinner and was relaxing on the couch watching TV when the doorbell rang. I opened the door to find Jane standing there. Jane! Ever since our last encounter, I have been avoiding her. Being around her makes me feel awkward. She takes charge of me; although it feels like a dream come true, it is still strange. “Hi, aren’t you going to let me in? It’s pouring outside.” I stepped aside and closed the door behind us. When I turned back, I was stunned! She had removed her raincoat, revealing an amazing figure in a latex minidress and black high heels. I felt like I knew what was coming next. “Well, my favourite slave. Why are you wearing those ugly male clothes? I hope you have at least some girly underpants on beneath them?” When I get home from work, I often slip into a thong and sometimes add more feminine attire. Wearing them feels… right, as if they were made for me. They are much nicer than regular men’s clothing. However, today I ate first after returning from work and hadn’t had time to change. I never dare wear any female clothing out at the office. Standing there unsure of what was happening, Jane pulled down my pants. “Oh my, you’re wearing plain boxers. We will punish you for that later. First, let’s dress you properly. Luckily, I came prepared.” She handed me a large bag that I hadn’t even noticed before and led me toward my room. She made me strip off all my clothes. Meanwhile, she opened the box containing my secret stash. Although I had changed the combination lock on it, she blackmailed me into revealing the code using photos she took during our last visit. She pulled out a g-string, stockings, and my 4-inch heels. She helped me put them on and led me downstairs to the basement. Once we arrived at the basement, she guided me to the table there. Taking some rope, she tied my legs to the table legs, then had me bend over and secured my hands to the opposite sides of the table. “So, let’s discuss your wearing girl clothes. I know you enjoy it; otherwise, you wouldn’t have bought them. So why don’t you wear them?” she asked. “I suppose one can’t be too obvious about it in today’s society,” I replied. “However, you can still wear certain items that remain hidden from others.” As I spoke, I heard her going through the bag of things she had brought along. “Panties, stockings, even a bra can be worn without people noticing.” I heard the tapping of her heels as she moved closer. Because my hands were tied to the table, I couldn’t look up at her directly. Then she stood beside me. She placed a ball gag in my mouth and fastened the straps. “We don’t want you making too much noise,” she said. I noticed she held a paddle in her other hand. Ouch! She slapped my butt hard. “That’s for not wearing any girl clothes today,” she explained, delivering several more slaps. “From now on, I want you to wear girl panties every day. I will check on you at random times. If I find you without them, you’ll receive the same punishment as right now.” She continued her rhythmic slapping of my rear end. Damn, that hurt! The ball gag prevented me from making loud noises I might have otherwise made. I definitely don’t care for pain games! But she made her point clearly enough.

Monday morning came and I woke up to take a shower. Friday was still fresh in my memory—not just the spanking Jane gave me, but also what happened that night! As I reached for the underwear I would be wearing today, my heart started pumping… They weren’t my normal boxers; they were some girly thongs. I felt really nervous, yet the memory of Friday night was still vivid, and I didn’t want to endure another such spanking. So I put on the thong along with the rest of my regular clothes and left for work—a day where I got very little done.