Playing with the Thief

Story Info
Opportunity comes knocking at my door thanks to a thief.
3.1k words
4.62
11.3k
23
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Swear this day couldn't get worse. It was raining all day so my walk to work was miserable, someone dented my apartment door, and now my laundry was missing from the other floor.

What an utterly shit day at least I had my fem clothes to cheer me up, and while I didn't hide my fem side, it was nice to experiment with new stuff to see if it works.

I looked at the mirror to admire my current outfit, a black and crimson pleated skirt with a fishnet top and a sleeveless ribbed black high neck shirt, the outfit was completed by some high thigh black boots.

I believe I had accomplished on looking like a "bad bitch" and that was perfect. Now all I had to do is some hoity toity Karen or some perverted dude with my laundry.

I sat down on my couch and put the television on to give me a break.

Luckily I didn't have to wait long as I heard a buzz on the door, well I guess I'll surprise this person with my outfit. It was always so fun to mess with the straights.

I lazily walked over and opened the door to the "thief" of my clothes. Carrying my phone and a book in one hand.

The door creaked open and I saw the guest on my door.

He was a petite young white guy, he couldn't have been more than 5'5 and 140 pounds soaking wet. With just a basic white T Shirt and black jeans, he wasn't exactly high fashion. His strawberry blond hair hung in a "manbun" behind him, it framed his face well and gave it a rather androgynous look alongside his blue eyes.

I wasn't expecting a cute little twink but I imagine he wasn't expecting a femboy like me and it really reflected in his "deer in the headlights" sight. He struggled to find his voice as he stammered awkwardly.

I rolled my eyes but looked at his hands which held

"Uh, I think these are your girlf- or your clothes! Sorry about this."

I chuckled and thanked him but because of my phone and book in my hands I awkwardly tried to take the hamper of clothes.

"Oh I can put these inside for you, if that's okay uh dude?" He struggled to hold the hamper with both of his hands, so I gave him a miniscule smile and invited the twink inside. A few paces inside he placed the heavy hamper inside in the living room. He panted heavily for a moment and stared down at my more salacious options in the basket.

"Having fun looking at my girly stuff? Or did you happen to drop something in there?" He shook out of his stupor upon the sudden inquiry.

"No no, I'm not gay or anything I was just resting..."

I raised my eyebrows and walked forward to him, still towering over his lithe figure. I must have seemed threatening to him as he started to retreat until his back hit the wall.

A bit peeved I asked "Oh so I'm gay? I'm gay for what reason exactly?"

The cute twink meekly gestured towards my whole body, pointing at what I assumed was the feminine attire. "It's cause like, you're in girly gay stuff, and I saw like panties and stuff in the washing machine?"

His ill attempt of an answer was met with a sinister chuckle. I crossed my arms and glared at my new "friend".

"So if you were wearing some panties and a skirt, you would be gay? Not some perverted thieving thief?" I glowered and brushed off my top and skirt.

"Yes, no. Wait, uh I didn't mean to take your uh!" I'd say he looked cute like this if he wasn't so terrified.

"Tell you what, I won't go to our landlord and neighbors and tell them about some perv stealing women's underwear or..."

He was white as a ghost and audibly gulped at my threat. "O-or what?"

I gave the poor boy a heart attack with a smile so menacing that it could have killed him twice.

"Or, you try on some panties and tell me how gay you really are?" I dug my painted index finger into his chest.

"No no no, that's ridiculous! I'm not gonna wear some girly panties for someone?" I laughed and pulled out my phone and made him watch as I journeyed through my contacts, each press getting closer to our landlord.

"No no no, I'll...I'll do it, just please keep this a secret!" He pleaded to me in complete desperation. I let my arm drop to my side and showed him the shut off phone.

"Excellent! Now come-" I gripped his hand tightly and dragged the hamper into my room. I pushed him onto my firm bed and pointed towards my long mirror that was placed on the side of the room.

"So Mr. Thief, I'll give you 10 minutes so you can work up the nerve to wear my 'gay girly clothes' and don't even think about chicken out. Got that clear boy?" He whimpered and nodded as I pulled him up from the bed and threw my pink and white lacy panties into his hands.

I stepped out of the room and as I left, I told the twink that I'd come back soon.

So I sat on my couch in the living room and crossed my legs as I waited for the time to tick down...

But soon it was 12 min past and I was starting to worry that he just left through the window and welched on the deal. I started to walk towards the room and was about to push the door wide open, I heard some kind of shuffling sound and a soft "dammit" I heard.

I decided to play secret agent and silently cracked the door open and the sight was astonishing to say the least.

This fucking twink was struggling with something as he looked into his reflection at my full length mirror and admiring himself while he wore my clothes! And looking hot while doing so. Somehow he found a dark-blue skater skirt that draped just above his knees, His legs were clad with skull patterned fishnets that paired well with ivory hairless legs and met with a pair of black ankle zip up boots. Then I found what he was struggling with, it was my midnight black ribbed corset which was attempting to cling to his body. He was stealing my clothes but damn he looked hot doing it.

I realized I had an opportunity and slid into the room quietly, glad that he was so engrossed by the corset and leaned my back into the wall and cleared my throat loudly. I swear I could see ghosts less white than his face as he cried out in surprise, his eyes widened fully.

"It's not what it looks like!"

I gave him just a pointed look and sniggered, breaking my calm demeanor but switched to give him a smug grin.

"So what does it look like? Cause it seems someone wore a little more than the panties?"

His eyes darted to the door so I walked in front of it, closing the door and pressed my back against his only escape.

"I was just, find something to hide the panties, so I wouldn't have to show you my-"

"Cock? Ass? Oh please, I've seen it all. Now let me show you something."

He shuffled uncomfortably, pushing his skirt down as if to hide a secret and cast no suspicion on it. An effort that would yield no success of course.

My plan wasn't hindered and I stood in front of the half feminized twink as he trembled under my glare.

"I was just c-curious! I'm not gay or anything..." he trailed off, horribly trying to convince himself of the claim.

"I never said you were, but you do make a cutie with that outfit. I'm sure some guy would love the look of it." I left him a sinister smile, my suggestion causing him to gulp audibly.

"T-thanks, are we done? I think I've done enough. I'm really sorry about wearing the clothes though." He meekly said.

I playfully made a thinking pose and walked around him, as if judging him for his frozen pose.

"Well, I see you did well by wearing the panties." He yelped as I flicked his skirt upwards and enjoyed a view of his cute bulge pressing against the thin panties.

"Okay yeah, so?" He pushed his skirt in, trying and unsuccessfully to hide his excitement.

"But I don't know if I can let you leave without finishing this outfit! You have such a good eye for outfits. You sure haven't worn stuff like this before?" He shook his head violently at my words and stammered out pitiful disagreements.

I grabbed his wrist and positioned his lithe body in front of the as I fiddled with the loosened corset and tied it tight as his body was suddenly constructed by the piece.

"Now doesn't that look better?" I smiled at the reflection of the mirror and enjoyed his flabbergasted look, the whole outfit came together to accentuate his lithe but slightly curvy body, his chest tied together with the corset gave him a more feminine figure and gave way to the look making him look like a goth girl. I laid my hands against his girlish waist and continued to adjust the corset so it was in line with the other skirts.

"Ah, I out did myself with your fit! You look like a bad bitch looking for trouble!" He nodded absent-mindedly with him still admiring the feminine boy that was in the mirror.

"Oh wait!" I lunged inside a drawer on my desk rifling through until I found-" I lifted my prize up and then hid it out of sight from my dressed up guest and positioned him again in front of the long mirror.

I worked quickly as I laid the gift against his neck and let him observe the new piece that bound the outfit together.

The twinks' hands played with the gothic item on his neck and gazed on the surprise.

A black collar with several spikes and a heart shaped locket at the very middle adorned his neck.

"Perfect, you're a bad bitch now! Looking for some trouble. " I was having a great time playing with my doll, but I was excited to claim his body in a moment.

He nodded his head to the 'bad bitch' remark and gazed in the mirror. I let my hands gently glide down to his hips and left it there as I made adjustments to his body.

"What...what are you doing?" it was a valid question but I think I would let my actions answer him.

I let my hands grip the hips of my victim tightly. I felt his breath hitch as I leaned into him, my tongue playing with the shell of his ear. He moaned with his body shivering from my touch, eliciting the reaction I wanted.

"You look like a bad bitch, and it looks like you found some trouble." My hands split from his narrow waist as one hand brushed his nipple and the other lightly grasped his growing erection under the skirt. The panties felt divine in my hands, his precum mixed with lace was more than pleasurable for both of us and I couldn't wait to go further,

I whimpered from my caress, each hand slowly growing in pressure. His corset clad chest shot out with my hand pinching and playing with his nipple. My other hand in his cock grasped it harder and started to stroke it through my former panties.

"Now bitch," I made him flinch through the sound of my voice alone. You can just walk away here and no one will be the wiser. But-" I sped up my movements while holding his throbbing cock that was tenting the skirt and staining it with a familiar substance.

"God you're so fucking hard I feel like you're going to want this, now beg bitch, tell me what you want!" I grinded my own growing cock, through the panties, against his pale ass and left precum all over the spots I pushed against. I pushed off my erection and slapped his pale cheek with it, his groan of satisfaction told me all I needed to continue. My bare thighs rubbed almost violently against his own fishnets, him whispering my name and losing himself in the fugue was making my cock harder.

I slapped my dick so hard against his ass that he yelped and left a string of precum against his cheek. I could see in the mirror that his eyes were rolled upwards and his lips trembled as he bit them hard. I wanted so bad to push into his body and claim him like the bitch I was making him but I needed to hear-

"Please, P-please it's so hot!" I grinned at his confession and I grabbed the lube that was left on the bed from my last session.

"Good girl, now relax and become my bitch..." My voice was soft and sweet but I couldn't say the same for my fingers, I pushed my now lubed finger into his own loosely made asshole. He grimaced first and tightened against the intruder in his body.

"It-It's so fucking tight." I shushed his complaint and eased a second finger into him, and then a third. Each finger elicited a more than girlish moan from my new conquest. Soon I felt his body relax and then he started to push back against my fingers.

I was fucking this virgin and he was fucking me back with fervor.

I slowly pulled out my fingers as I saw his hole struggle without the previous invader, he cried out in both pleasure and pain from the attack from my lubed digits. I placed my throbbing cock against his hole and watched him gasp in surprise.

"God, you're fucking hot girl, now I want you to beg!"

"Beg for what!" His whimpers were just making cock even harder and he could feel my excitement rim his ass.

"You know what, I'm going to make you my bitch girl, I am going to fuck you so hard that all you'll be able to do Is think of my erection for years, I am going to fuck you so bad that you'll become a slut for being dressed up and giving yourself to me!" He cried out as my head continued to rim his hole and he nearly screamed in need of my promise.

"PLEASE FUCK ME, PLEASE FUCK ME LIKE A BITCH!" His voice echoed inside the room but I bet he would think that he would be heard from everyone in the apartment building.

"Good-" I placed the head of my erection inside the rim of his ass "-GIRL!" I pressed on and the head was easily swallowed by his wet arse. His gritted teeth and eyes rolling upwards was proof that I was making good of my threat. I started to saw my cock inside him, his hole so tight that I swear that it was made for my cock.

An evil laugh is all he heard over his own moans as every push was pressing the limits of his body and I drank in the satisfaction of my new bitch taking almost every inch of my cock. His 'O' face was the greatest thing I would say is the best thing I'd ever seen but seeing his cock bounce inside his skirt would top that slightly top that.

I slowed my assault on his previously virgin hole and I cooed in the slut's ear. "Oh look at you, it didn't even take 30 minutes to get you all dressed up like my whore. Look at the mirror Ms. Thief, look at how I fuck your pussy and how hard your cock is bouncing against your cock? I guess you're NOT-" I pushed in further "AS" I pulled back leaving him with emptiness causing him to whine in desire "STRAIGHT" I press back in going in even further and he cried out in pleasure. "AS YOU THOUGHT!" Finally my cock bottomed him out and he practically squealed in submission.

He simply responded by violently humping my cock back to take me in as far as he could, his g-spot fully hit and he was starting to spurt out bits of his cum from the fucking I gifted him. "More, please more! I need to be fucked!"

I watched his feminine body go even faster and I grinned in a way that would have made the most evil of villains jealous of it. I granted his request and sped up even faster and his moans mixed with the slapping of my cock against his ass told me that he was giving me everything.

He became my bitch and he was loving it.

His hole tightened so hard and I knew he was getting close to orgasming and watched him stroke himself so hard that he was about cum for an entire year.

"I'M CUMMING!" He hissed through gritted teeth and his tear stained face as he gazed in the mirror. His body shook in pure pleasure as violent explosions of cum filled his skirt and panties. MY erection still throbbed but I was smiling at his surrender to the pleasure and I gazed how his cum streamed down his feminine legs. I pulled myself out slowly and he grimaced of the removal and he was about to turn around, probably to accept the reality of what just happened, but I grabbed his arm and threw him onto my bed.

He could only lay in shock as I started to stroke my cock as fast as possible and he froze in shock as I came so hard that I roared in delight. The splatter of cum went all over his girly outfit and his face, he sniveled as he felt his prize stream down all over his body. He panted as his tongue snaked out and tasted the cum that landed on his face. He realized what he was doing and looked away and blushed like a schoolgirl from me.

"You were such a good girl, I'll give you a small reward!" I gleefully said through my own spread out breaths. "You can keep those clothes, plus more-" He started to refuse. "If and only if, you become my bitch for the next month. You were a good fuck but a shitty thief." He contemplated and looked abashed into the mirror to take in how he was riddled with the mixture of my and his cum.

He nodded silently and looked up like the bitch he became.

I gave him a sweet smile and lifted up my skirt where my growing cock expanded out of my own underwear.

"Now, let me teach you a lesson in how you suck my cock."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymous3 months ago

I know this is difficult to do well in this type of story, but the scene felt a bit creepy due to the lack of consent. But besides that the characters and writing are pretty good

4Leather4Leather3 months ago

Love crossdressing just wish I could find someone to push the envelope. Love it can’t wait for the next chapter.

AnonymousAnonymous3 months ago

I prefer josou seme from the bottom's perspective but we take what we can get.

Share this Story

Similar Stories

"But you're wearing a skirt" Girly clothes doesn't mean I'm a bottom.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
My Adorably Hung Summer Roommate Darren meets Danielle, a petite redhead w/ something extra.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
Teacher Surprise College student bumps into his high school teacher at a club.in Transgender & Crossdressers
More Stories