Caught Snoop Forced To Crossdress! (M/M) | NEW CHAPTER 03.25

[WrappedUp]

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?”

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?”

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.”

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.”

[Snozzberry]

He certainly is done when the pictures get out. I love your first person stories, they seem more real. I'm wondering how my kidnapping idea is coming along?

🖐🖐

[WrappedUp]

Chapter 2 : Getting Roped Up

As he opened the door he took a step back and braced himself.

Instead I was there, blushing and trying to cover my body with one arm.

"Now see, that wasn't so bad." He said, grabbing my wrist.

He led me back to the bedroom. He stood me in the center, turning me around to face the window. I held my breath, hearing him open the drawer and grab something.

Suddenly I felt his hand pulling my wrists back, I could feel rope rub against my skin.

"Hey! You don't have to do this!" I moan, feeling the rope wrap around my arms as he got my wrists behind my back. He locked me in a box tie, arms parallel with the right wrist tied to the left elbow and vice versa.

I groaned in pain as he securely tied my arms, making me completely immobile. I realized my body is fully open now and I'm unable to hide my bare skin.

He wrapped a few lengths of rope around my upper arms and chest, securing them even more. As the rope binds me I feel a hint of arousal creep in. The skirt began to rise as I got hard, trying my best to resist the feeling.

Finally he turned me around to face him. I hunched over, looking down to the floor. I could see a tent pitching from my erection.

He reached down and lifted the skirt, ensuring I was actually wearing the satin panties. I knew that the tip of my cock visible as it threatened to burst out.

I saw his eyebrows raise as he eyed my bulge, lightly rubbing his finger up it.

"Ahhhh", I moaned as he robbed the front of my crotch. I couldn't help but make noise, even as I bit my lip. I tried to struggle but the bindings had me completely secure. My cock sprung up fully as he looked me over. I tried to look away but the embarrassment in my face was too obvious.

"Good, I thought for sure you would try to get away with not wearing them." He let the skirt fall back down. He walked around me in a circle for a moment and then led me to the bed where I sat down on the edge.

"Is this enough for you," I said, "does this make you happy? Can't you just let me go now?"

“Not quite.”

He grabbed more rope, tying my ankles together. He wrapped the rope around them four to five times and then pulled the ends between the legs, cinching it between the ankles. He threw my legs up and swung me onto the bed.

"This is too much!" I whined. "Come on, you don't really have to do this...I'm not going anywhere."

I groaned, trying to wiggle my legs around but finding there to be no slack. I could only wiggle my toes uselessly. I let out a small gasp as he threw my legs up and swung me onto the bed. He quickly flipped me onto my stomach. I feel the air on my behind as the skirt lifts up. He gave me a light playful slap.

"Ah!" I groaned. My cock is rock hard, I unintentionally begin to rub my crotch on the bed, closing my lips to suppress my moans.

He pulled up my bound ankles and with another length of rope, bent them back and secured them to my forearms. He stepped back and looked at me, helplessly hogtied.

"Hmm something is still not right. What am I missing here?”

"What are you talking about!" I cried out. "Isn't this enough you sick creep! This is overkill. It hurts! Can't you loosen the ropes a little bit? You don't have to do this man!"

"That's it!”

He walked over to a different drawer in the dresser. I tried to look but I couldn’t see what he put in his hand as he hid it behind his back.

"What are you doing?" I said. "What are you holding...what is that?"

My heart pounded in anticipation. I instinctively clenched my cheeks, fearing something would be entering me from the rear.

As he sat on the bed next to me he stroked my hair slightly. I felt a tingle across my scalp. It was then he showed me his hand, a large red ball gag dangling from his fingers.

"This is what’s missing." He said.

"No! No! No don't gag me please, please don't gag me! Come on ple-mMMMMMMMMMPH!"

I screamed as he pushed the gag into my mouth, realizing I'd invited it by firing my big mouth off. I felt the ball invade my mouth, pushing deep as my teeth wrapped around it. I felt him strap it around my head, pitching my hair slightly.

"mmmmmmmph!" I cursed, feeling my jaw stretch open as far as it'll go. I could feel myself starting to drool. I whimpered, unable to form coherent words with the gag in my mouth.

He pushed me on my side to face him as he knelt next to the bed.

"Mmmmmph!"

I groaned, drool pouring out of the corner of my mouth as I slumped over on my side. I saw his face as he got level with me, pure amusement in his eyes. I could only imagine how pathetic I looked to him with the gag in my mouth.

He slowly ran his fingers over my body. Up my legs, along my arms, across my chest, over my exposed midriff.

"mmmmmmmph!" I sobbed into the gag, closing my eyes and feeling his fingers all over my body. I squirmed around more, feeling sensitive as he got closer to my belly button. I couldn’t help but let out a muffled laugh through the gag, anticipation building up as I felt the blood rush to my crotch.

He touched the ball between my lips, lifting the front of the skirt again. I was fully erect now.

"MMMMMMPH!" I shook my head. I tried to turn around and thrust my body into the sheets to hide my erection. It was no use, he began to rub the bulge, watching my face.

My eyes went wide and I let out a loud moan through the gag. The slightest touch of his fingers on my cock was enough to make it twitch, the entire head was sticking out from under my waistband.

[Snozzberry]

Great story. Somebody sure sounds like he's having fun being in a dress. I wonder how he would a fringed leather one piece bikini no top.

🖐🖐

[Jeffpa1967]

Hi everyone that is enjoying the story.
It's been great RPing with WrappedUp on it.
If you have ideas, outfits etc. that wants us to consider post it on here.
We are a little more chapters along in the RP so you might not see it right away. WrappedUp is working hard to getting it ready and posted.
Thank you for reading

[WrappedUp]

Chapter 3 - There Can Be No Denying

"Well somebody must be enjoying this more than they thought." He said.

He continued to rub along my satin covered shaft, his hands going up to fondle my erect nipples, visible from under my sports bra. The combination of feelings started to overwhelm me, I wanted to pull away but part of me wanted more. I looked at him with pleading eyes, unsure exactly what I was begging for.

He grabbed by the shoulders and thighs and pulled me closer to the edge of the bed. He leaned in, lifting my skirt up again as he touched the exposed tip of my cock with his tongue.

"MMMMMMPH!" I screamed through the gag. I was confused, I didn’t know what to feel anymore. My sensitive tip was tingling, I tried to pull my hips back but part of me wanted to move my cock forward into his mouth. I battled with my emotions, more drool pouring out of my gag as I whimpered and moaned.

He pulled the panties down, fully exposing my six inch unit and the clean shaved base. I screamed through my gag, desperately trying to break free of the ropes. I realized how much my struggling and noises were turning him on, seeing a tent forming in his pants.

He put the tip of his tongue back on my penis and started swirling it all over the head. I felt an electric shock through my body, the ticklish sensations making me quiver and moan.

He licked the shaft starting at the base. He ran his tongue up to the head, giving it a little triple lick on the tip.

"Mmmmmmmph!"

My cock continued to twitch, my moans getting louder and as he wrapped his hand over my already gagged mouth. I felt even more helpless, completely at his mercy. This show of dominance makes me hot behind the ears, my whole body is shaking.

One of his hands went along my shaft and stroked as he moved his tongue around the head.

"MMMMMMPH!" I whimpered, muffled by his palm. Pre-cum spilled out of my penis. I was close, I could feel it. I began to convulse involuntarily.

Everything in me wants to thrust my cock forward and have him swallow it completely, but somehow it felt like I would be submitting the last bit of control I had over myself. I was almost totally dominated by him, but I felt the need to keep resisting, as hard as it was.

I didn’t even last ten more seconds.

I closed my eyes and tried to thrust my cock forward.

He took it all in, moving his tongue around. I screamed out. I felt his nose hit my lower belly. The pleasure was unbelievable, I had never felt anything this good before. The ropes no longer hurt, I got lost in them realizing I was his in this moment. I had no say of what happened to my own body, and I loved it.

He slid his lips up and down, sucking with every outward slide. He sped up, feeling me quiver. He pulled me closer, getting as much of me in his mouth as possible. He slid a hand behind me and grabbed my ass. He began pushing me to help my thrusts. More and more pre-cum spilt out. My cock was twitching, it was like I was already orgasming. The feeling of pleasure extended further than I knew possible. The feeling of his mouth tight around my shaft left me moaning and wiggling around.

After it all I moaned loudly through my gag as I began to shoot blasts of hot cum at the back of his throat.

"Mmmmmmmmph!", I threw my head back and moaned. I couldn’t believe how much it was turning me on to cum in the mouth of the man who'd captured me and made me into his little crossdressing slave.

He put his hand on my chest to feel my pounding heart.

As I finished he licked my dick clean, pulling my panties back up and removing the ball gag, a long trail of saliva following. I breathed heavily as I finally took air in my mouth again.

He let me sit in the feeling for a few minutes and then brushed my hair aside.

"It seems we both enjoyed that, not sure who enjoyed it more.” He said.

I looked at him with my mouth open, eyes doe like, cheeks red.

"So do you think you learned a lesson about breaking in and going through other people's private things or are more lectures needed?" He said.

"Mmmh", I nodded my head, unable to string together a sentence. I almost felt sad to think it was over. Maybe the post nut clarity hadn’t hit yet, or maybe this had awakened something in me that I never knew about myself.

He looked puzzled, unable to read my face. He sat me up in the bed, leaving me in my ropes as he left the room. I looked all around, wondering if anything else was going to happen. He returned with a glass of water, setting it down as he untied me.

I saw the rope marks all over my body. I rubbed my wrists, I had nothing to say. I wanted to crawl into the bed and hide. I felt embarrassed after the display I had just put on. I had never been so vulnerable in my life. Still, I didn;t feel the urge to take off the feminine clothes, maybe because it was all that covered my body, or maybe for some other reason.

"Drink this so you avoid getting dehydrated. You spent a lot of fluid between drooling and cumming.” He said, handing me the glass.

"Thank you." I said meekly as I drank the water. My hands were shaking.

"You look lost. Makes me think you didn't learn anything with that lesson and that worries me. I have other interests here outside of my dressing fetish that you haven't found. What happens if you come back and start snooping again?"

"I um...", I tried to think of how to reply. More fetishes? Did I really want to know what else he was into? Wasn't this enough? Why did it feel like I wanted to take him up on this offer? I had a gut feeling that even if he freed me I’d just come back.

"If there is even a chance of you sneaking back in here again then we might need some more lessons to work it out of you, or into you."

Although already spent, I felt my cock twitching, begging for more. I thought I'd feel nothing but disgust after my orgasm, but instead I felt warmth. The way he untied me, cared for me by giving me water. I was still afraid, but I didn't feel unsafe. I didn't feel violated.

I didn't know what exactly I was feeling, but it was just nice to feel something this strong again so I chose to stay quiet.

I leaned over and nested my head in his chest. He softly stroked my hair, letting me stay there for a little while. I had no idea how to feel but I did enjoy the warm touch. I wouldn’t have expected this when he first bound my wrists, I feared much worse than this.

For now I figured I would just enjoy this unless I was given a reason not to.

[Snozzberry]

He will be back for future lessons I'm sure. He enjoyed it so much.

[Jeffpa1967]

Maybe many lessons.

[Bradstick]

Got the chance to read this story and it did not disappoint! I loved the gag and the torture of him learning that he enjoyed being bound and cross dressed. Great work!

[tiemetakeme]

Wow, great story. Is there more? Interested to see where it goes.