Sissy Cuckold Story

Her Boy Wears Satin When He’s Bad

by Sandi’s Boy

She knew just how to push my buttons for maximum effect when she wanted me to feel embarrassed, humiliated and submissive. Lucky for me, she didn’t feel this way often but when I misbehaved or she felt that I needed a little humbling to get me back in line she wouldn’t hesitate to put me in my place. In general, my bad behavior would find me bent over the bed and depending on how much I disappointed her, my butt would be turned various shades of red with one of the paddles, hairbrushes, whips or other spanking implements.

However, every once in a while she found the lesson was more effective and long-lasting if she included some humiliation in the punishment. One of the best ways to do this was to make me wear feminine clothing. Usually this meant I was put into a pair of panties and would be required to wear them under my clothes for the rest of the day or sometimes for several days.

The feel of the panties were a constant reminder that I was her bad little panty-wearing boy that will do anything for his Mistress and the fear of being discovered only added to the embarrassment of wearing the panties. She would always make me pull my pants down to show them to her because she knew this reinforced my humiliation and my obedience to her. Yet, wearing panties was mild humiliation compared to actually wearing a nightie, bra, pantyhose or other feminine attire. Being made to dress in women’s clothing caused me to really feel the full impact of humiliation and almost always brought a red flush of shame to my cheeks. She didn’t particularly want me to look like a woman (we found out long ago that I make a really scary looking woman!), her intent was to embarrass me and ensure that she got into my head where she could get the submissive attitude she was looking for. One of her favorite punishments was to put me in a sexy nightie while I cleaned the master bathroom. She would check on my progress every once in a while and apply a paddle to my ass for encouragement to speed things up and do a better job.

As I sat at my desk wearing panties under my dark suit and still feeling the sting of the whipping I got in the kitchen with the dreaded wooden spoon before coming to work, I glanced over at the ringing phone and cringed when I saw my home phone number popup on the caller id. I hoped that she wasn’t still mad at me but I knew she was still fuming when I walked out the door this morning to hurry to the office for an early meeting.

It all started this morning as I was getting coffee in my travel mug for the commute to work. She made the comment that she was surprised her hairdresser didn’t call back to confirm an appointment for today. She had a date with her boyfriend to celebrate their six month anniversary tonight and really wanted to look her best. I looked at her sheepishly and said, “I forgot to tell you – she called yesterday and said she only had one opening and it was the first appointment today so you needed to call back yesterday if you wanted it.”

I could see the look of shock on her face. “And you didn’t tell me?” she asked incredulously.

“I was right on the middle of something and just completely forgot,” I replied with eyes downcast. This wasn’t the first thing that had slipped through the cracks due to my busy work schedule and she was really getting tired of coming second to my work issues.

She stared at me for several seconds before storming across the kitchen and grabbing the wooden spoon from the kitchen drawer. “Pull your pants down.” I looked at her with pleading eyes and she immediately added, “NOW!” I knew there was no way to get out of this so I unbuttoned my dark blue suit pants and pulled both the pants and my underwear down to my knees.

Her eyes were bright and angry as she glared at me. She pointed to the counter top saying, “Bend over.” I reluctantly turned around and put my hands atop the counter while exposing my backside to her and the evil wooden spoon. She wasted no time putting her left hand squarely in the small of my back and with the wooden spoon in her right she began a rapid staccato of firm swats onto the cheeks of my ass. As I started to squirm from the rapid-fire sting of the spoon, she shouted, “Stay still and don’t move.” She continued to beat my ass with the spoon as I twisted around trying to stay still but finding it impossible. She must have delivered 40 or 50 hard cracks with the spoon in less than a minute. I was beside myself with the stinging in my cheeks as it seemed a thousand bee stings had just been delivered.

When she removed her hand from my back and stopped swatting me with the spoon she said, “Get upstairs and put on some panties. You’re lucky that you are running late and have a meeting or I’d beat the crap out of you right now.” I scrambled to pull my pants up from my knees as I rushed up the stairs to change my underwear into a pair of panties from her drawer.

When I came down she told me to pull down my pants and show her my ass and my panties. I pulled my pants down to first show the bright red satin panties and then lowered the panties to show her the welts on my ass that were already changing from bright red to shades of blue. There was little doubt that my ass would have some bruises tonight. I started to say that I was sorry but she shushed me with her hand and said “You’re going to be late for work. Go.”

I pulled my pants up, grabbed my suit jacket and left for work with a burning sensation giving off heat in my backside.

I picked up the phone and said, “Hello sweetie,” in the sweetest voice I could muster.

I was surprised when she responded in a relatively nice voice and asked “How’s your butt feel?”

“It still burns and tingles,” I answered honestly.

“Good,” she said obviously pleased. “It will give you something to think about the rest of today. I was hoping to tease you today about my date tonight and how you could help your Mistress get ready by bathing me, shaving my pussy and helping me to get dressed.”

I had a little frown on my face and asked boyishly, “You’re not going to let me do that?” I was disappointed that I might not get to participate in this little ritual.

“Oh no, you’ll still be doing that. But, I think you’ll be more distracted today thinking about the other things that you’ll be doing tonight.”

Now I was beginning to get a knot in my stomach. Her voice was developing a more sinister tone and I realized that her anger had not passed. I waited for her to continue but she paused to let her comment sink in. Finally, I asked, “What things do you mean?”

“I mean that you will come home, hang up your clothes, and strip to your panties before you get me a glass of wine and bring it upstairs to me. Then you will look on the bed where you’ll find your CB-2000, a butt plug, and pretty girlie clothes. You’ll put on the CB, put the plug in your ass and put on the clothes and you’ll get all of this done in less than 15 minutes because I’ll be waiting for you to begin taking care of me. Also, I don’t want you to say a single word from the time you walk through that door until you go to bed unless I tell you to speak. Do you understand me?”

I gulped and quietly said, “Yes, maam.” I could feel my little weenie making a tent in my pants.

“Oh, and one more thing,” she added. “When he arrives you will go downstairs and let him in wearing your pretty little nightie and see if there is anything that he needs to drink. Once he is comfortable you will tell him that you’ve been a bad little boy and that you must stand in the corner until I come downstairs to join him. You’ll go to the corner of the living room and put your nose against the wall while pulling down your panties to just below the cheeks of your ass and pulling up your nightie to showoff the spanking that you got this morning and the butt plug filling your ass. You’ll stand there like that until I come down. After I’ve properly greeted my guest, I’ll call you over to lie across the loveseat so that I can finish the spanking that I started this morning. Once I’m finished, you will be dismissed to the spare bedroom where you will close the door, get in bed and stay there until tomorrow morning. You can remove the butt plug once you get to your bed but the CB will stay on until I decide you can take it off. Got it?”

I was in shock and didn’t know what to say. She had never done anything like this before. Although he knew she was my Domme, he had never seen any overt signs of our relationship other than me responding to her orders to get drinks and mild things like that. He certainly had never seen me dressed in women’s clothing or even being spanked in front of him! This was a real escalation in things and I was terrified!

It was quiet on the phone line for a moment before she asked insistently, “Boy?”

I choked out a stunned, “I understand.”

“Okay, have a good day at work honey,” she said in a cheerful voice and the line went dead.

I was completely distracted the rest of the day and didn’t get anything accomplished at work. When the day finally ended, I drove home in rush hour traffic but barely noticed anything that was going on around me. I pulled into the driveway and opened the door of my house to the sound of my wife’s iPod playing upstairs where she was beginning to get ready for her date. As she requested, I hung up my suit, stripped off the rest of my clothes with the exception of the panties and got her a glass of white wine. When I got to the bedroom I saw the components of the CB-2000 on the bed next to the jelly butt plug. There was also a bright red satin nightie and red women’s shoes sitting on the bed. I couldn’t believe that I was going to do this. I took the wine to the bathroom where my wife was brushing her teeth. I wanted to say something but I remembered that I was not allowed to speak. She said, “Thank you,” as I sat the wine on the sink top and then said, “Hurry up putting your things on. I’m ready for my bath.” I walked back into the bedroom and quickly began to put on the CB-2000. It seemed like it took forever to get the butt plug in my tight asshole. Even with a lot of lubrication, it hurt so badly but I was afraid what might happen if I didn’t hurry. Once it finally popped in, I put on the red nightie and shoes. I felt absolutely ridiculous and the shame and humiliation were burning throughout my body. I felt like the world was spinning in my head but once I was dressed I went to the bathroom where my wife was just starting the bath water.

“Don’t you look cute,” she said with a devilish gleam in her eyes. “Let me see your ass,” she said with a twirl of her finger to indicate that I should turn around and display my ass to her. I turned around and lifted the hem of the nightie as I lowered my panties. She looked for just a moment before saying, “Mmmm, there are going to be some nice marks for a few days.” She then raised her arms over her head and said, “Undress me.” I immediately pulled my panties back up and began to help her undress.

I helped bathe her by washing her back and her hair. I started getting an erection as I ran the wash cloth over her nude body in the bath but the CB-2000 quickly put an end to that as the cage blunted any further growth of my little penis. This was made worse when she had me shave the parts of her pussy that she could not easily reach. It was painful and I tried to will it to go back down but to no avail. After she was finished bathing, I used a big fluffy towel to dry her off and then put powder all over her body. She dried her hair as I ran an iron over the clothes that she laid out for herself. Once she was dressed, she sat at her makeup table to begin putting on her makeup.

“He’s due to arrive any minute. You can go stand downstairs in the foyer and wait for him so that he doesn’t have to wait too long when he arrives. I’ll be down when I’m finished putting on my makeup.”

So here I find myself – standing in my own house, next to my front door, waiting for someone to arrive that will be ravishing my wife all night. He was going to see me dressed in women’s clothing for the first time and would be witnessing the most humiliating thing that has happened to me up to this point in my life. My mouth is dry, my knees are shaking and I just want to run and hide. I feel foolish standing here and I keep trying to tell myself that this is crazy and men don’t do this.

However, I continue to stand here …… waiting.