My Step Mom's Punishment

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Caught by Step mom while cross-dressed.
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raj2842
raj2842
201 Followers

Editor's note: this story contains scenes of non-consensual or reluctant sex.

*****

Kyle's POV

I waited to see if the coast was clear. I could hear the clacking of her heels as she walked around the downstairs hall. It was 8PM - she would be gone until 11PM. Her friends had invited her over to a dinner party that evening. Since both of my younger siblings were out of town I would be left in charge of the house.

Heather called up to tell me she was leaving.

"Okay, see you later!" I shouted.

I heard the bang as she shut the door. I now had the entire house to myself.

I am 19 years old, skinny and relatively tall. I have a younger brother and sister, both of whom are 16. Heather was my stepmother, although I barely knew her. I had never really seen her as much of a maternal figure, especially given how attractive she was. At 34 years old she still looked amazing, with gorgeous blond hair and a curvy body.

It was the weekend and I had nothing to do. The weather was cold and most of my friends had been busy with their studies. I was completely free.

I had a secret fetish that I was very ashamed of. I had it throughout my teenage years. I loved wearing women's lingerie. There was something about the slightly taboo feminine nature of it all that I found alluring. My stepmom masses of sexy outfits in her drawers. Whenever I was home alone, I would often sneak into her room and try something on. It was especially sexy knowing that I wasn't supposed to be doing this.

I had always been careful not to give away my secret. I covered my tracks - always making sure to keep everything in her room the same. One time I was particularly proud of myself when I had been wearing a lacy bra and panty set and she had come home. I had pulled my own clothes over the undergarments when she entered the house. She was clueless as to what was under my clothes. I then carefully returned them to her drawer while she was in the kitchen.

Today I had all the time in the world. I decided to get a takeaway for dinner - pizza while watching TV. I spent some time playing video games as well. After over an hour of anticipation I decided to venture upstairs.

I crept into the room. Everything looked perfect: the bed was made; the drawers were shut; the floor was clear. There was a faint unusual smell in the area. If figured it was some new sort of perfume she'd bought.

I cautiously opened her bottom drawer. This drawer was filled with an assortment of clothes; mostly exercising stuff. There were also a few night slips. I took one out, trembling with excitement. It was a rose-red satin nightie, just the right size for my body. There was white lacing on the bust.

I'd worn it before once, but only briefly - it was a new slip. I stripped off my clothes and slipped into it. The material felt amazing on my body. I spent a couple minutes looking at myself in the mirror, feeling it on me. While I gazed at my reflection I felt slightly drowsy. I couldn't quite tell why.

I decided to go back to my bedroom and lay down under the covers. I left my clothes lazily strewn about the floor of my bedroom. I was too tired to properly tidy up, so I just fell right into bed. The soft fabric brushed against my skin. I knew I shouldn't fall asleep like this - I might be caught. But for some reason I felt so tired and weak that I couldn't help my slumber. I tried to fight it - but sleep was too tempting. My eyes slowly fell shut.

Heather's POV

I made sure to leave the party early. I checked my watch as I climbed into the car. It was 10PM - perfect. The drug usually lasted for about 3 hours. It would take 20 minutes to get home. Hopefully, if everything had gone to plan, he would be fast asleep by now.

I drove back as quickly as I could. This was important. I needed to teach him a lesson for what he'd been doing. I knew Kyle had been wearing my underwear for a long time now. I cringed thinking of the time that he'd decided to wear my underwear under his own clothes. I had clearly seen the outline of my bra under his shirt. At the time, I'd pretended not to notice out of sympathy. But now I'd had enough.

I'd placed a particular gaseous scent within the room. The gas could cause unconsciousness for roughly 3 hours. If I arrived just before 11, whatever the case, Kyle would be asleep.

I wanted to really shock him. Another person in my position might've only confronted her son about the situation. However, Kyle was different. He wouldn't simply stop doing something with a few words; he was stubborn. I needed to really teach him a lesson.

I'd initially planned to simply catch him in the act of wearing my lingerie. However, this seemed a little difficult given that he would have time to conceal what he was wearing and think that he had deceived me. In addition, the shock and humiliation would be instant - I wanted to draw it out. I wanted to teach him a lesson that he would never forget.

I reached the house, driving slowly and quietly, though I knew he was in a deep slumber. I left the car and walked up to the house, entering as quietly as I could. Creeping up the stairs, my heels clacking on the floor, I anticipated the worst. Kyle's welcoming voice would tell me my plan had failed. Fortunately, I heard nothing.

The door was ajar, I could hear his light snores. Clothes were strewn about around the entrance to his bedroom. I crept in, switching on the light. I could see him lying under the covers. I quietly cursed him as I saw what he had chosen to wear. My new nightie: a beautiful satin rose-red slip. He was wearing one of my newest nighties. I wouldn't have been as angry if it had been an old one. But this was too far.

I checked the time: 10:25PM. I checked the sturdiness of the bed again. It was just as strong as before. A metal frame with bars at the foot with a beautiful headboard on the other side. It was very strong and did not shake easily. Good.

I walked back into my bedroom, picked up the various restraints that I'd been hiding and set to work. So far, everything had gone to plan. Kyle would be in for a very big surprise...

Kyle's POV

I woke up feeling dizzy. My eyes were not adjusted to the darkness. It had clearly been a while since I'd drifted off. I shifted slightly. I noticed that I'd spread my limbs out on the bed and had somehow kicked off the covers. I felt exposed with the nightgown against my bare skin.

My heart stopped. The nightie - she might already be home. I panicked and reached for my alarm clock. Only I couldn't.

My arms seemed to be fastened down by some sort of restraints. As my eyes adjusted to the light, I could see the leather straps on my wrists. I gently pulled on them to test their strength - they were secure. I noticed my ankles were cuffed as well, spreading my legs on the bed. I struggled against them, finding that they were just as secure as the restraints on my arms. They looked as though they were connected to the bed posts, yet also linked underneath the mattress for extra security. I looked down at my helpless body, bound in my stepmom's nightie. My heart began to race.

My first thought was thieves. Perhaps someone had entered the house, found me asleep and tied me up. But if that were the case, why would they go to the trouble of getting expensive bed restraints. A simple handcuff or roll of duct-tape would have sufficed. My mind began racing through anyone who would have access to the house. Perhaps my younger siblings had returned home early and decided to pull a prank? If that were true, they would know about my fetish. My heart began to beat even faster.

Suddenly, I heard footsteps. High heels clacking on the landing. I immediately realized they were my mom's and went into a panic. I began shifting on the bed, desperately trying to escape my restraints. But the tight bonds refused to budge. Slowly, the door began to creak open.

I saw Heather enter the room. She was wearing a beautiful red dress that clung to her body. The dress reached down to just above her knees, accentuating every curve. She was wearing stockings underneath.

I closed my eyes, not daring to look at her. I could hear her walk up to the side of the bed. My face went scarlet, feeling the sinful satin against my body. The mattress shifted as I felt her sit beside me on the bed.

She tutted. "You should have known I would catch you at some point." I felt her hand feeling up and down my chest. I tried to twist away, refusing to look at her. "Always so cautious... of course you would have had no way of knowing that I'd hidden a gas capable of knocking you unconscious inside my room. Although I expected you might have noticed the bed restraints I'd hidden underneath your mattress."

My heart continued to pound, I felt like I was about to faint again. My own stepmother had tied me up. The fact that I was in her nightie made it so much worse.

"I'm sure you're wondering what's about to happen to you," she said. "You won't like it."

I groaned. My mind still struggling to process what had just happened. I was trapped. I had nowhere to run, nowhere to hide; completely exposed and vulnerable; tied down in the most humiliating way. All of this by my own stepmom. Worse still, she'd known about my dirty habit. I cringed at my own foolishness.

I croaked. "I'm so so sorry..."

"Look at me," she commanded.

I looked at her; the gorgeous woman sitting next to me and stroking my chest.

"Your apologies are long overdue. This is the price that you will have to pay now. You crossed the time a long time ago - and wearing my new nightie pushed you even farther out."

"I won't do it again," I pleaded. "Just please let me go... don't tell anyone..."

She chuckled. It was a dry chuckle - no humor. "That's a lot of demands for someone who's tied up. You want me to untie you AND keep my mouth shut?"

I felt like crying. "Please I'll do anything."

She looked down at me. "We'll have a compromise. I'll let you decide which punishment you get. Either: I let you go but take pictures of you and tell everyone I know about your disgusting fetish. Or I tell no one but you have to stay tied up for... a little longer..."

I groaned again. "The... the second one..."

"Say what it is."

"You don't tell anyone... about my habit..."

She nodded. "Your disgusting habit. And?"

"And... you keep me tied up for a while."

"Excellent," she said, smiling. "I'm glad you picked the second option because, to be honest, I was going to keep you tied up anyway."

She felt up and down my body, kneeling beside me. Her hands felt down the fabric, stroking just over my private parts and then down my legs. It felt good - I would've enjoyed it under different circumstances. But now I just felt disgusted. Disgusted partially with how she was punishing me but more with my own stupidity. She then dragged her hands down to the hem and straightened the nightgown out - my struggles had crumpled it.

She then got up and headed to the door. "I'm just going to get some toys for us to play with. Don't go anywhere." She winked before leaving.

Heather's POV

I knelt beside my bed, looking through the various objects I had to torture Kyle with. He was still sleeping. I'd strapped him down well enough. The restraints I'd bought were strong and durable. However, they needed to be underneath the mattress in order for them to work. Therefore, I'd had to hide them on Kyle's bed the day before in order for them to work. I'd made a lot of preparations for this - but hopefully it would all be worth it.

I scratched the inside of my thigh, irritably. The lingerie I was wearing underneath my dress was hardly comfortable.

I heard shuffling coming from the other room. Kyle had woken up. It was time for the big reveal.

I slowly walked down the hallway. I could hear the shuffling become more frantic. I gently pushed the door open. He was still on the bed, spread-eagle, looking utterly humiliated in my sexy little nightie. Kyle looked away and screwed his eyes shut.

I sat down next to him on the bed. I stoked the fabric that clung to his chest, almost feeling sorry for the scared boy.

"You should have known I would catch you at some point," I began to explain. I felt a great sense of power over him - my guilty little victim. "I'm sure you're wondering what's about to happen to you. You won't like it."

I heard him whimper an apology. I didn't like how he refused to even face me - still avoiding the consequences after all he did.

"Look at me," I commanded. "Your apologies are long overdue. This is the price that you will have to pay now. You crossed the line a long time ago - and wearing my new nightie pushed you even farther out."

He began to plead. "I won't do it again. Just please let me go... don't tell anyone..."

I liked the sound of his pleading. I ran my hands up and down the satin on his body. "That's a lot of demands for someone who's tied up. You want me to untie you AND keep my mouth shut?"

His begging continued.

I gave him an ultimatum. I liked exercising the control that I now had. Whatever he chose, I would keep him tied up anyway. "Either: I let you go but take pictures of you and tell everyone I know about your disgusting fetish. Or I tell no one but you stay tied up for... a little longer..."

He chose the second option, greatly pleasing me. I got him to ask to be tied up. I was beginning to enjoy this. I shifted my position on the bed so that I could kneel over him. The teasing began with me running my fingers down his body. I felt over his cock, making him shuffle uncomfortably. My fingers worked their way down to his legs. I straightened out the nightgown to make him look nice and neat. I then climbed up from the bed. Time for the real fun to begin.

"I'm just going to get some toys for us to play with. Don't go anywhere," I said, playfully.

Kyle's POV

The wait might have only been a minute, but it felt like hours. I began to tremble, wondering what torment she had in store for me. This was already bad enough.

I considered calling for help. Likely though, no one would hear - it was nighttime in a relatively secluded suburban area. Our house was large and detached from the surrounding buildings. I doubted I would be heard. But even if I was and they decided to intervene... would I really want that? For them to see me like I was? No. If I wanted to escape, it would have to be by myself.

Suddenly, I heard her walking back to the room. My heart began racing, fearing what was about to happen. She came in, still wearing that sexy red dress, holding a purse. She reached in and pulled out a blindfold. I shook my head vigorously.

"No no no. Please, let me see," I begged.

She ignored me and carefully placed it over my forehead. I struggled as she wrapped the material around. Then she pulled it down over my eyes and tightened it at the back. I continued to shake my head, trying to get it off. But to no avail.

"I would gag you as well," she explained. "But I wanted to play a little game with you. It is where you guess what object I am touching you with."

I recoiled. The last thing I wanted was a gag. Timidly, I nodded, still fearful of what was about to happen.

"I'll start out easy," she said. I heard her reach into her bag and pull something out. I then felt a tingling sensation on my satin-clad chest. It felt soft and feathery. The feeling went up and down me, then onto my arms and neck. It tickled slightly and irritated my face. "What do you think it is?"

I gritted my teeth as I felt a hand on my thigh, slowly creeping up towards my private area. The feeling was soft and feathery.

"Is it..." I stammered. "A... a feather duster?"

"Good. You are correct." She took the toy off my body. "Oh, and I should mention, if you guess wrong, I will be harsher on you."

I groaned. Of course, it had to get worse.

Another fabric began to tickle me, on my leg this time. It wasn't feathery yet still rather soft. There was a sudden stab of pain on my thigh when she cracked it. I winced slightly. "Is it a whip?"

"Yes, you're doing well."

I heard her rustle about inside her bag for a few seconds, waiting in anticipation. I then heard her turn something on, chilling me. It was a low electric hum. I knew exactly what that was and did NOT want her to use it on me.

"That's a vibrator!" I said, sharply.

"Huh?" She said, sounding confused. She untied my blindfold and pulled it off my head. I was grateful for the freedom to see again, before realizing my mistake. She was holding an electric toothbrush. She smiled triumphantly. "You're not going to like this."

I looked up at her, terrified. "W... what are you going to do to me?"

"Oh, I can't tell you that," she said, sifting through the items in her bag. She paused, reconsidering for a moment. "Well actually I can tell you since you're tied up and can't do anything about it. But I think I'll just keep you in suspense."

I shuddered, watching her slip on a pair of satin gloves. They were black and tight-fitting, reaching past her elbow. She strutted across the room and stood in front of the bed, swaying her hips. The tight dress made my mind start to race with titillating thoughts. She then crawled onto the bed in-front of me grabbing my nightgown. She pulled it up my body to my chest area, exposing me completely. My only protection was now gone. She looked down at my privates, smiling as it twitched.

She crawled up to me, kneeling in-between my thighs. "I'm flattered that I turn you on. I'll leave the gag off for now, but if you get too loud it's coming on."

I looked at her, terrified of what might happen next. I was right to be scared.

She dug her vicious fingers straight into my ribs, wiggling them. I cried out, holding in my laughter as best I could. The silk gloves only made it worse. That feeling of violating irritation that you feel when tickled was too much to bear. She wiggled and twisted her fingers, going into every nook and cranny on my ribs. I tried to hold out as long as I could, but it soon became unbearable. I burst out laughing.

"Aw... are my fingers just a little too ticklish?" She cooed, stroking those awful fingers up and down my abs.

I almost felt like crying. The tickling was becoming too much. Her fingers gave me no relief as they wiggled up and down my sides and between my thighs. I couldn't stop the painful laughter. It hurt so much.

Eventually, after what felt like hours, she stopped her torment. I gasped, trying to catch my breath. It was too much. My face was hot and red. Tears were streaming down my cheeks. I must have looked like a mess.

"Poor baby. I'll give you a little break," she said, patting me on the thigh. "This is far from over."

I strained my neck to look up at her. "W... why are... y... you doing this?" I panted.

"I think we both know that" she said, ruffling the lacy fabric on my chest.

"No... you're... you're being so so... cruel."

She placed a hand on my chest. "Poor baby. I'm only giving you what you deserve," she said with false sympathy. "But if you like I could give you a little reward. Before we get back to the torture."

"Huh?" I said, confused and slightly scared by what she thought was a 'reward'.

She climbed off the bed and reached for a couple of pillows. The she helped lift my neck to place the pillows underneath, propping my head up. I now had an easier view of the room in front of me. She reached over and placed a satin-clad hand on my cock. It was completely soft.

"Hmm... I may need to warm you up," she said, cheekily.

I wondered what she meant by that as she got up off the bed and stood at the foot, right in front of me. She started swaying her hips from side to side, feeling herself up and down. She turned her back to me, swaying her ass.

God she looked sexy, I thought to myself. That tight dress was almost too much. I tried to calm myself down given the situation - this was my stepmom.

raj2842
raj2842
201 Followers