Favorite Sissy

After that first shameful minute I saw my mother’s face shift from a resolute thoughtfulness into that stern look she usually reserved for my brothers. I knew I was finally in serious trouble, but nothing could have prepared me for the punishment I was about to receive.

She approached the bed where I had laid out all the clothing and rope I had collected over the years. I shifted myself nervously about to see what she was doing. She ran her eyes over the collection, and then gingerly picked up some old, white nylon tights. “So you like wearing these clothes, do you?” she asked. “Y…yes,” I squeaked out. “Fine, then let me help you. Open up,” she directed as she held them up to my face.

Uh oh, I thought, here comes the punishment. She’s going to make me eat them. I was reluctant, but what could I do? I opened my mouth and in went the panty section of the hose. I had a slight gag reflex, but I managed to cough and sputter a bit and not get choked on the material. But I wasn’t shocked at this punishment until she wrapped the legs of the tights several times around and tied them tightly behind my head.

I had expected to have to suck the tights for a minute, but the tying seemed unnecessary since I was prepared to take this punishment. But my mom had apparently done some thinking about this since the last time I was caught. Somehow she’d gotten the idea that she could shock my deviant behavior out of me. That is what I surmised, anyway, when she picked up several lengths of rope and began wrapping them around my ankles, tying me firmly to the bedpost.

She was nothing if not thorough. She tied my ankles, knees, waist, chest, upper arms, elbows and wrists tightly to the bedpost. I was fully immobilized from head to foot with my wrists high up on the post. I was confused by this seemingly bizarre punishment, but I was also somewhat aroused. After stepping back and examining her work, she turned and said, “Good night,” just before she turned out the light and pulled the door closed behind her.

Needless to say, I was a little panicked. The tight bondage had left me pulled up to the post with only my toes touching the floor. I could sag in my bonds, but it was mentally difficult to give up that scant contact with the floor. I had never spent a night in full bondage before, and it was very scary. For what seemed like hours, I alternated between agony, guilt, and sexual ecstasy.

Luckily Mom couldn’t sleep either. She must have been thinking about thing over some strong drink. Mom was never much of a drinker, but when she came back in the room some time later she was a little shaky on her feet. I’m not sure she was fully drunk, but she was not exactly herself either. She just stood there, looking at me with bleary, tear-stained eyes.

I was soaked with sweat and the inevitable messy results of my stimulating situation. As the minutes passed, I awaited my next fate in anxious agony. She examined me with a sad look on her face. She said nothing until she noticed the large wet spot in the front of my ruffled panties. I just looked at her with ashamed exhaustion.

“No, no, no,” she muttered into her hands. Exasperated, she said, “I see that your punishment has had the wrong impact on you. I just don’t know what to do with you. I love you, but you have to learn that you can’t play like this.” She entered my closet and brought out one of my leather belts. The energy flowed back into my body as I realized I was about to get the first strapping of my life. “I’ve never had to raise my hand to you before, but I have to make an impression on you. I’m sorry Sweetie.”

It wasn’t so bad. In fact, after the first jarring swat, the stinging and my struggles only served to increase my pleasure. “Mmmmf!” I outwardly protested, but soon reached ecstasy again and there was no hiding the results. I just slumped in my bonds afterward, not even jerking when the belt rapped my silk-pantied rear.

The strapping slowed, and then stopped as my mother finally realized that the belt had also had an unintended result. Tears came to her eyes as she dropped the belt and slumped to the floor. All of the energy seemed to drain out of her as she began sobbing in earnest. Her sobbing eventually ran dry, but she didn’t speak for a long time. She just looked at me with her glassy eyes for a long time.

She must have come to a decision, because finally she let out a sigh and relaxed. “I’m sorry, my precious one. If you really want to dress and act that way, I have no right to change who you are. I’ve been stupid and selfish. I just really wanted you to continue to be my special little boy. But I love you no matter what you do. I’m sorry for everything. Now let’s get you out of those ropes.”

She sniffled a bit as she resignedly fumbled with my bindings. She couldn’t see that my eyes were filled with emotion now. I loved my mother, and I never wanted to disappoint her, but the draw of my fetish was too strong. And now I had been forcibly introduced into a world of new pleasures of bondage and pain. I was not angry with her in the slightest.

She finally managed to release me from the bedpost, and I flopped onto the bed, utterly exhausted – physically and emotionally. I curled up into a fetal position and must have looked truly pathetic and completely disheveled. My sweet mother took compassion on me then like she used to do when the other boys were mean to me.

She sat down on the bed and took my head into her lap. She brushed the wig hairs out of my face and gently caressed my cheek. I just lay there feeling spent but content. “I should have known I couldn’t change you,” she sighed. “You have always been my sweetest child, just like I imagine a little girl would have been. I didn’t think I’d ever have a daughter. But now I do, and it’s going to be just fine.”

“Mom,” I said, “I love you.”

Fresh tears came to her eyes and she squeezed my neck and stroked my shoulders. “I know you do, sweetie,” she replied. “I love you too, and I’m going to do whatever I can to help you be the person you want to be.”

I looked up at her with surprise. She had just given me her blessing to be the girl I’d always wanted to be without qualification, and was now even willing to help. It was a dream-come-true for me. I hugged her about her thighs and felt as if I could conquer the world.