A first person account by Tanner K.
The worst punishment I ever received was my first and only spanking from my stepmom, Victoria. (Although she was my Dad’s fiance at the time). I secretly dressed up in her bra and panties when she was away on the week-long business trips she took every now and then. I loved to especially wear the ones I found in her laundry hamper cause they had been used recently and still smelled like her. Sharing intimates with her always got me rock hard.
One day I was watching TV in the living room, wearing nothing but her white bra and panties and touching myself. Suddenly I heard a key in the door and I panicked. I jumped up to run out of the room but my foot caught on the coffee table and I tripped. Just as she opened the door she caught me running away into my room. Before I could reach my door she screamed, “stop right there!!”
I froze and she grabbed me by the arm and spun me around. The look on her face was pure horror. She screamed at me and looked right down at my erection which was poking through her tiny white panties. She screamed “What the hell is this?!!” and looked me up and down in complete disbelief. My face turned red and I started to tear up from the absolute humiliation I felt. I hesitated for a moment and then she shouted, “answer me!” So I said “I’m so sorry…please, please, please…don’t tell anyone about this.”
She folded her arms and shook her head as she stared at me. She said I was a “dirty little pervert” and that she was tired of catching me doing perverted things (she had walked in on me masturbating to pornography twice before). I just stared at the carpet trying not to make eye-contact. She told me to “look at me when I’m talking to you young man!”
Then she went into a long tirade about how what I was doing was sinful, and immoral, and unnatural. She said that if she were my real mother she would take off her belt and give me “an old-fashioned butt-whipping…one that you would never forget.” She said that maybe if I had had some real discipline growing up I wouldn’t be a grown man of 19 years still unable to control his “disgusting impulses.”
At that point, I hung my head and started to sob. “You’re right, Victoria,” I said. “I’m so so sorry. Just please don’t tell anyone. Please. I’ll do anything.”
The next thing I knew she was removing her belt from her waist. “You got yourself a deal,” she said. “Now turn around and bend over!”
I was completely caught off guard and I looked up at her in disbelief. Then she put her hands on her hips and shouted “now!!” I did exactly as she said, just grateful to know that she wasn’t going to tell anyone about my little kink. Without any warning she pulled down the panties I was wearing and two seconds later the belt whipped across my bared cheeks. I jumped up and grabbed my butt. She pushed me back into position and said that if I didn’t “take it like a man” I was going to get it much worse. I believed her.
She stood there spanking me in the hallway in front of my room for a good half hour. It would have been over quicker but I kept moving out of position and so she would add strokes or start over from the beginning. The belt was braided leather and so it stung like hell. After a lot of crying (by me) and yelling (by her), I was able to take 25 consecutive whips without moving which I had to count out loud. She took a deep breath and said, “alright, you’re all done. Your secret is safe with me but if I ever catch you doing anything like this again, you can expect more of the same.”
I wiped the tears from my eyes and said “Ok. I won’t do it again, I promise.”
After that day I was a model stepson. She never had to use the belt again (although she got close and took it off a few times to make me fall in line). No one knows about either the spanking or the crossdressing except the two of us. Now for some reason, the only thing that gets me harder than dressing up in a woman’s panties is wearing them while I feel the scourge of a thin, stingy, leather belt. But that might make for another story, for another time…