Caught Snoop Forced To Crossdress! (M/M) | NEW CHAPTER 03.25
Posted: Tue Mar 18, 2025 12:22 am
This story is based off of a roleplay I am currently doing with Jeffpa1967.
It was written in first person so this is a combination of his writing and mine put together in my perspective. I hope you enjoy this little bit of erotic fun!
Chapter 1 : I Came In Through The Bedroom Window
It should have been an easy job, nobody was home.
This wasn’t my first rodeo, I’ve been doing this petty crime for a couple years. Sure, most would consider breaking and entering a little more than petty but I never hurt anybody. I only snuck into houses when I knew no one was there and took a few things to go pawn.
Maybe they’d notice, maybe not. I still haven’t been caught this whole time.
Tonight was just like any other night. I put on my thick black hoodie and tied the string tight on my grey jogging pants. I hid half of my face with a red bandana and put on a pair of cheap black shoes. With a large duffel bag over my arm I crept into the bedroom window, left open on the second floor of the house.
Maybe the homeowner was stupid, or maybe he didn’t think anyone would have the guts to climb up his wall. It didn’t matter much.
I took out my flashlight and looked around the room. A bed, a desk, a dresser, some video game posters on the walls, a mess of clothes on the floor, yup this was a guy’s bedroom. I quickly crept over to the drawer and slid the middle one open.
My eyes nearly burst out of my head as I saw an arrangement of colourful panties.
"Huh? I thought this was a dude's room," I mumbled, looking around. I shrugged, holding a black lace thong in my hand as I pushed around to look over the other pairs. I smiled, my robbery had turned into an unexpected panty raid.
Before I could get too happy I looked over my shoulder, thinking I heard something.
In an instant I was grabbed by the top of my hoodie and put up against the wall.
“HEY!†I screamed, feeling someone grab my wrists. They were forced behind my back and strapped together. I felt velcro slide along my hands as I was locked in a pair of cuffs. I’m barely able to process what’s happening as the attacker binds me in a few seconds.
"Ah!"
I drop the panties to the floor and begin to wiggle around.
"What's going on! Let me out of these!" I whimper, trying to look back to get a glimpse of the person. I pull at the cuffs, finding no slack. I wonder if I’ve been caught by the homeowner, a cop or even worse, a fellow burglar.
My hood is pulled back and the bandana around my neck is lowered.
"Who are you and why are you here going through my stuff?â€
The man spoke, turning me over and shining the light in my eyes. I squinted, struggling to catch a glimpse of him.
I feel like a bug that just had its stone turned over.The man looked me over, seeing my clean shaven face, shaggy dirty blonde hair and glasses. My green eyes dilate.
I can’t see him but he looks thin and a couple inches shorter than me. I looked over, seeing the open door.
"Nevermind!" I said, "Just let me go and we'll forget this ever happened okay?â€
I tried to muster up a smile, noticing how the man blocked the door. My heart was beating fast as I continued to fight the restraints, feeling them grow tighter with each attempt.
"Let you go?" He let out a slight laugh. "First you broke into my house."
He took a step forward, cornering me.
"Second, you were going through my stuff.â€
He put his hand against the wall, preventing me from moving towards the window.
"And third you discovered my fetish that I have only shared with a select few."
He put the flashlight down on the dresser, keeping it shining on me as he grabbed my chin.
"How can I just let you go?"
"You psycho!" I cried out. I looked at the drawer of panties again, shaking my head.
"I'm not trying to...exposure whatever weird shit you're into! I was just checking windows okay, I was only going to steal a few things and go. Please, I don't care about all this stuff, I won't say anything I promise!"
I can finally see the man’s intense eyes. He’s clean shaven like me, his light brown hair falls close to his shoulders. There is something oddly effeminate about his features, but the force he projects on me is strong. I can’t make out what he’s wearing but I can see that his midriff is exposed and he’s wearing awfully short shorts.
"Come on pal, I don't want to go to jail. I'll do anything, just let me go!"
"Anything?" There is a barely suppressed grin on his face.
"Here's the deal, you do what I say and we will see if you can earn your freedom to leave."
He looks me over, top to bottom.
"You might as well face facts, you're going to pay for your mistake, one way or another."
"Earn my freedom?" I titled my head, "Come on, what kind of stuff are you thinking about?"
I felt my cheeks go red, noticing the way he was looking me up and down. I looked back down at the panty drawer and back up to him. My eyes adjusted and I could see he was wearing a low necked white top with strings across the chest. It was cut below his navel. He had on a microscopic plaid skirt with white knee high socks.
Oh my God, I broke into a crossdresser’s house!
He quickly snapped a picture of me, turning it over to show me. I looked like a wreck, my eyes were neatly watering. I was more scared than I knew. My bottom lip trembled, knowing I was in deep trouble.
"Any problems and this goes to the police.†He spoke calmly. "Since you seemed to be fully engrossed with my lingerie collection, enough for me to walk up behind you without you even realizing, let's see about getting you more intimate with them."
He gave a slight grin as he went to the dresser and pulled out some clothes.
"No! No no no! Oh come on, you're not serious," I whine, watching as he dug through the dresser. I looked at the clothes he pulled out, feeling a sinking in my chest.
On the bed he laid out a white shiny spandex sports bra, a short white pleated tennis skirt and a pair of red satin panties.
"What are you planning here, you're not gonna make me...wear them are you?" my voice dropped, "You're not serious right?"
"That is exactly what is going to happen." He grabbed my arm dragging me down the hall.
"You sick fuck," I sobbed as he led me along, "You really get off on this shit? What the fuck is wrong with you!"
My words were weak, my voice cracking as we entered the bathroom. He uncuffed my wrists and stood in the doorway. I wanted nothing more than to bulldoze him and run, but I knew I was outmatched.
"You are going to put these on. I'm going to allow some dignity and let you change clothes here, but if we have any issues that privilege will be revoked." He said. "There are no windows so leaving is not an option. Stop crying and get dressed."
"I can't believe this", I groaned, looking around the small washroom. It was a small square shaped room with a toilet, a sink and a mirror.
"A word of warning, any time you're taking too long to change just gives me more time to think of outfits to dress you in.†He said, looking at the clothes and back at me.
"You aren't going to get away with this you know!", I said as he began to close the door. It was no use. As I was left alone in the washroom I looked at the lingerie.
It took me a while to build up the courage. I thought maybe I could grab something and whack him in the head when you opened the door again but there was nothing heavy in here. I also thought of the picture, stone cold proof that I broke into this house.
I lifted off my sweater, revealing my soft slightly pudgy stomach. I had just recently shaved, getting my belly hairs "just for fun". I dropped my pants and stripped naked, looking at the clothes again and sighing deeply.
I pulled on the red satin panties, barely able to contain my manhood. My tip was showing from the waistline. I quickly put the skirt on, pulling it up just under my belly button, the shadows around the waist making my innie appear deeper than it really was.
The skirt was so small, it felt like my balls could dangle out from the bottom. I was blushing, looking at myself in the mirror, hardly able to believe what I was seeing. I finally put the sports bra on, struggling to fit in over my chest.
"Oh my God", my eyes watered as I looked at myself. I covered my stomach with one hand and shook my head.
I tried to speak but it was hard to get the words out. I sighed, licking my lips as I swallowed my pride and called out.
“I’m done now.â€
It was written in first person so this is a combination of his writing and mine put together in my perspective. I hope you enjoy this little bit of erotic fun!
Chapter 1 : I Came In Through The Bedroom Window
It should have been an easy job, nobody was home.
This wasn’t my first rodeo, I’ve been doing this petty crime for a couple years. Sure, most would consider breaking and entering a little more than petty but I never hurt anybody. I only snuck into houses when I knew no one was there and took a few things to go pawn.
Maybe they’d notice, maybe not. I still haven’t been caught this whole time.
Tonight was just like any other night. I put on my thick black hoodie and tied the string tight on my grey jogging pants. I hid half of my face with a red bandana and put on a pair of cheap black shoes. With a large duffel bag over my arm I crept into the bedroom window, left open on the second floor of the house.
Maybe the homeowner was stupid, or maybe he didn’t think anyone would have the guts to climb up his wall. It didn’t matter much.
I took out my flashlight and looked around the room. A bed, a desk, a dresser, some video game posters on the walls, a mess of clothes on the floor, yup this was a guy’s bedroom. I quickly crept over to the drawer and slid the middle one open.
My eyes nearly burst out of my head as I saw an arrangement of colourful panties.
"Huh? I thought this was a dude's room," I mumbled, looking around. I shrugged, holding a black lace thong in my hand as I pushed around to look over the other pairs. I smiled, my robbery had turned into an unexpected panty raid.
Before I could get too happy I looked over my shoulder, thinking I heard something.
In an instant I was grabbed by the top of my hoodie and put up against the wall.
“HEY!†I screamed, feeling someone grab my wrists. They were forced behind my back and strapped together. I felt velcro slide along my hands as I was locked in a pair of cuffs. I’m barely able to process what’s happening as the attacker binds me in a few seconds.
"Ah!"
I drop the panties to the floor and begin to wiggle around.
"What's going on! Let me out of these!" I whimper, trying to look back to get a glimpse of the person. I pull at the cuffs, finding no slack. I wonder if I’ve been caught by the homeowner, a cop or even worse, a fellow burglar.
My hood is pulled back and the bandana around my neck is lowered.
"Who are you and why are you here going through my stuff?â€
The man spoke, turning me over and shining the light in my eyes. I squinted, struggling to catch a glimpse of him.
I feel like a bug that just had its stone turned over.The man looked me over, seeing my clean shaven face, shaggy dirty blonde hair and glasses. My green eyes dilate.
I can’t see him but he looks thin and a couple inches shorter than me. I looked over, seeing the open door.
"Nevermind!" I said, "Just let me go and we'll forget this ever happened okay?â€
I tried to muster up a smile, noticing how the man blocked the door. My heart was beating fast as I continued to fight the restraints, feeling them grow tighter with each attempt.
"Let you go?" He let out a slight laugh. "First you broke into my house."
He took a step forward, cornering me.
"Second, you were going through my stuff.â€
He put his hand against the wall, preventing me from moving towards the window.
"And third you discovered my fetish that I have only shared with a select few."
He put the flashlight down on the dresser, keeping it shining on me as he grabbed my chin.
"How can I just let you go?"
"You psycho!" I cried out. I looked at the drawer of panties again, shaking my head.
"I'm not trying to...exposure whatever weird shit you're into! I was just checking windows okay, I was only going to steal a few things and go. Please, I don't care about all this stuff, I won't say anything I promise!"
I can finally see the man’s intense eyes. He’s clean shaven like me, his light brown hair falls close to his shoulders. There is something oddly effeminate about his features, but the force he projects on me is strong. I can’t make out what he’s wearing but I can see that his midriff is exposed and he’s wearing awfully short shorts.
"Come on pal, I don't want to go to jail. I'll do anything, just let me go!"
"Anything?" There is a barely suppressed grin on his face.
"Here's the deal, you do what I say and we will see if you can earn your freedom to leave."
He looks me over, top to bottom.
"You might as well face facts, you're going to pay for your mistake, one way or another."
"Earn my freedom?" I titled my head, "Come on, what kind of stuff are you thinking about?"
I felt my cheeks go red, noticing the way he was looking me up and down. I looked back down at the panty drawer and back up to him. My eyes adjusted and I could see he was wearing a low necked white top with strings across the chest. It was cut below his navel. He had on a microscopic plaid skirt with white knee high socks.
Oh my God, I broke into a crossdresser’s house!
He quickly snapped a picture of me, turning it over to show me. I looked like a wreck, my eyes were neatly watering. I was more scared than I knew. My bottom lip trembled, knowing I was in deep trouble.
"Any problems and this goes to the police.†He spoke calmly. "Since you seemed to be fully engrossed with my lingerie collection, enough for me to walk up behind you without you even realizing, let's see about getting you more intimate with them."
He gave a slight grin as he went to the dresser and pulled out some clothes.
"No! No no no! Oh come on, you're not serious," I whine, watching as he dug through the dresser. I looked at the clothes he pulled out, feeling a sinking in my chest.
On the bed he laid out a white shiny spandex sports bra, a short white pleated tennis skirt and a pair of red satin panties.
"What are you planning here, you're not gonna make me...wear them are you?" my voice dropped, "You're not serious right?"
"That is exactly what is going to happen." He grabbed my arm dragging me down the hall.
"You sick fuck," I sobbed as he led me along, "You really get off on this shit? What the fuck is wrong with you!"
My words were weak, my voice cracking as we entered the bathroom. He uncuffed my wrists and stood in the doorway. I wanted nothing more than to bulldoze him and run, but I knew I was outmatched.
"You are going to put these on. I'm going to allow some dignity and let you change clothes here, but if we have any issues that privilege will be revoked." He said. "There are no windows so leaving is not an option. Stop crying and get dressed."
"I can't believe this", I groaned, looking around the small washroom. It was a small square shaped room with a toilet, a sink and a mirror.
"A word of warning, any time you're taking too long to change just gives me more time to think of outfits to dress you in.†He said, looking at the clothes and back at me.
"You aren't going to get away with this you know!", I said as he began to close the door. It was no use. As I was left alone in the washroom I looked at the lingerie.
It took me a while to build up the courage. I thought maybe I could grab something and whack him in the head when you opened the door again but there was nothing heavy in here. I also thought of the picture, stone cold proof that I broke into this house.
I lifted off my sweater, revealing my soft slightly pudgy stomach. I had just recently shaved, getting my belly hairs "just for fun". I dropped my pants and stripped naked, looking at the clothes again and sighing deeply.
I pulled on the red satin panties, barely able to contain my manhood. My tip was showing from the waistline. I quickly put the skirt on, pulling it up just under my belly button, the shadows around the waist making my innie appear deeper than it really was.
The skirt was so small, it felt like my balls could dangle out from the bottom. I was blushing, looking at myself in the mirror, hardly able to believe what I was seeing. I finally put the sports bra on, struggling to fit in over my chest.
"Oh my God", my eyes watered as I looked at myself. I covered my stomach with one hand and shook my head.
I tried to speak but it was hard to get the words out. I sighed, licking my lips as I swallowed my pride and called out.
“I’m done now.â€