tagTransgender & CrossdressersHalloween Agreement

Halloween Agreement


Halloween was fast approaching. This made me nervous as my new girlfriend had gotten me to agree to a costume I would never have thought I'd wear. A school girl. She said it would be fun, and that nobody judges on Halloween. Not that she had to try convincing very much, I cave in to her every whim pretty much all the time. I guess you could say I have a fairly submissive personality. The days sped by and Halloween was upon us. I knocked on the door to Kate's apartment that evening equal parts timid and excited. I'd always had a fascination with women's clothing; the skirts and dresses; the ruffles and lace; it all seemed so much more interesting than bland men's clothing. I blinked away my thoughts as the door opened to reveal my girlfriend Kate. She clapped in delight, grinning at me and grabbing me by the arm, practically dragging me inside and slamming the door.

"This is going to be so fun!" she exclaimed while herding me into her bathroom.

I half-heartedly mumbled something about "fun for her," trying to downplay my own eagerness to dabble into femininity.

"Strip slut!" she ordered me abruptly and slapped me hard on the ass. I couldn't recall her ever talking to me like that and I was taken aback a bit.

"What part of 'strip' didn't you understand bitch?," she went on as I gawked at her wide eyed and open mouthed. She reared back as if to slap me and instinctively I flinched and scrambled to get my shoes off. She smiled and lowered her arm as I fumbled about, hopping on one leg to get out of my jeans and quickly pulling my t-shirt over my head. I stood there facing her in my boxers finally and she simply cocked an eyebrow at me and glanced down at my underwear. I grinned sheepishly and dropped them to the floor. Despite my momentary confusion, my cock was standing out rock hard. It clearly approved of this treatment, and Kate appeared quite pleased at this discovery. She stepped closer to me and reached down to grab my cock, squeezing it tight and looking up at me.

"So...it seems someone gets turned on being ordered about." She squeezed hard, digging her nails into my cock and I winced, my knees buckling a bit, allowing her to look down at me.

"It's pretty hot," I gasped.

Kate leaned forward and gave me a peck on the forehead before releasing my cock, allowing me to stand back up, and reached behind to slap me on the ass. "Now cover yourself from the neck down with that nair in the shower and wait for 15 minutes before you turn the water on. Make sure to rinse it all off then. Can't have my slutty little school girl covered in ugly hair. I need to attend to some things in the apartment."

With that she walked out of the bathroom and closed the door, assuming that I was going to do as I was told after my display of submissiveness. I stepped into the shower and began covering myself with the bottle of nair. Once this was accomplished I was left standing there in the shower with only my thoughts to keep me company. I had read about dominant/submissive relationships a bit on the internet, never realizing Kate might be into something like that, or myself for that matter. Kate was right though, being told in no uncertain terms what to do in that tone she had used was definitely exciting. Myriad thoughts raced through my mind as to what this could mean as far as our relationship went. Would this be just tonight? Or would we do this every so often? The tingling of the nair started to invade my thoughts, slowly turning into a burning sensation. I glanced at the clock by the sink and realized the 15 minutes was up, I had completely zoned out. I slid the shower curtain closed and turned the water on, letting it get warm before turning the shower head on. As the water cascaded over me, all my body hair to include my legs washed off of me and into the drain. I glanced about the shower, taking in all the feminine soaps and shampoos. I shrugged and started washing up. Might as well use girly body wash, I would be dressing as a girl tonight after all.

Clean and hairless I turned the water off and stepped out of the shower to towel off. I was amazed at how different, and good, that felt with smooth hairless skin. Once dry I looked to my clothes so I could get dressed, only to find they were gone, and a frilly pink satin baby doll with matching panties had taken their place. My cock started to rise as I reached out to pick up the panties and slide them up my smooth legs. Wow did that feel good! The baby doll settling onto my body felt almost as good. By this point my cock was again rock hard, tenting the pink panties.

I exited the bathroom and stepped into Kate's bedroom, where she was sitting on her bed wearing a black leather corset and long black velvet skirt. She had one thigh high black booted leg crossed over the other and was tapping what appeared to be a riding crop in her hand.

"Good girl! I expected you to come out naked and confused." She stopped tapping the crop in her hand reached down to slap it twice on the floor in front of her.

I chuckled and said, "was pretty obvious what I was supposed to do. Didn't even hear you come in the bathroom," I smiled at her.

She just frowned at me at slapped the floor with the crop again. With a start I moved over to stand in front of her, figuring that's what she wanted. She was really getting into the whole Dominatrix thing, really quickly too! She sighed, sounding vexed swung the crop full force against my smooth, bare thigh. I squealed in surprise and jumped back a bit.

"What was that for?," I asked rubbing my thigh where she had struck.

She repeated the same motion with the crop for a third time, but before I could react, said "that means you are to kneel there bitch. Not quite as smart as I thought. Ah well, that just means I get an excuse to use my crop."

She looked at me expectantly and I realized i she was still waiting for me to kneel. I did so, a little gingerly. Too gingerly it turns out, for as soon as I had settled in place on my knees before her the crop slashed through the hair to sting my shoulder, right across one pink satin spaghetti strap. I hissed in pain but stayed in my position. She was taking to this REALLY quickly. She looked at me kneeling before her, a tiny smile at one corner of her mouth. I opened my mouth a couple times to say something, but I had nothing so I just waited to see where this would go.

"Good girl," she whispered to me. I didn't even know why. "Now that you know your place, and mine, we'll establish the ground rules. More will be coming when I decide, but some basics have to be gotten out of the way."

"Ground rules for Halloween? Didn't know there," WHAP. The crop stung my other shoulder and I winced in pain.

"First, you will speak when spoken to. Second, all your statements directed to me will end with Mistress, k?"

"Alright, alright," I said, rubbing my newly stinging shoulder. WHAP. The crop slapped against my unprotected shoulder.

"What did you say slut?"

"Ouch! I meant yes Mistress."

"That's better. Third, if you have a need to speak but haven't been spoken to you are to ask me, 'may i speak, Mistress?' If I respond no, then you are to remain silent until I say so, and will not ask again." She looked at me, and I thought I detected a twinkle in her eye."

I was pretty sure she was waiting for me to say something, but the last thing she said wasn't a question, and didn't seem to require a response, so after brief consideration and I decided it would be wise to stay quiet.

"Good girl!" she patted me on the head and I felt myself smile at that. "I knew you'd be trainable! Lastly, you are to obey me at all times. If you feel any of these rules are unfair, there's your clothes," she pointed to my clothes stacked neatly near a dresser, "and you know where the door is. Understand?"

This sounded very serious. Was she for real? Seemed to be going a bit far for a Halloween night out. Her dominant personality she'd slipped into was definitely turning me on, despite the whacks I'd received from her riding crop. I imagine this is all a character she's decided to play for Halloween, and what harm could it do? If I left I was sure she'd call me back and tell me what a party pooper I was. A quiet clapping noise interrupted my thoughts and I realized she was slapping the crop against her palm again, awaiting my reply. It dawned on me that my inner monologue did not pause time in real life. What the hell, I though, may as well go for it.

"I understand Mistress," I smiled up at her.

"Splendid!" she beamed. "You passed all your tests with flying colors!" She sounded pretty happy, which made me feel I had made the correct choice. "Now let's get you ready my submissive little princess."

She got up and directed me over to her vanity where I sat obediently as she began to apply make up to my face. The entire time she instructed me as to what she was doing, why she was doing it, and told me in time it would be second nature to me. I simply sat still as she worked on me, glad to have the attention and wondered why it would matter if I learned about make up or not. When she was done I started into the face of a pretty girl. Just the face however, she had a decidedly boyish haircut.

"I know sissy," Kate replied to my unspoken thought, "luckily I have the cutest thing for you." She disappeared briefly into her closet and emerged with a honey blonde wig, which had two red ribbons catching it into pig tails. She situated it on my head and fastened it into place with a couple hairpins and nodded to herself.

"What do you think, princess?"

"Wow, it's almost like I'm looking at the reflection of a real girl!" SLAP. I let out an unintentionally girlish squeal as Kate's hand spanked my ass three times in rapid succession. I realized my mistake. "Mistress! I like it Mistress!"

"Much better slut." Again Kate disappeared into her closet and returned, this time with a red plaid skirt, white satin button up blouse, white stockings, bra, and panties. "I know you love your cute little baby doll princess, but it's time to get ready, strip."

No hesitation from me this time as i pulled off the baby doll and panties, letting them puddle around my feet before I stepped out of them. Kate handed me the panties first, followed by the bra. It had false silicon breasts sewn into it i noticed and I struggled to snap it behind my back. Kate didn't say a word, but rolled her eyes and stepped behind me to do the clasp herself. Next came the stockings which I carefully rolled up my legs at Kate's instruction. Then the short plaid, pleated skirt, which once zipped on my hips hung just over the floral patterned tops of my stockings. I slipped the blouse on and buttoned it up and I was complete. The definition of a slutty school girl fantasy. Almost I learned as Kate returned one last time from her closet with a pair of 4 inch heeled black patent mary janes. I buckled them onto my feet and stood for inspection.

Kate walked around me a few times, sizing me up, squeezing my ass, caressing my arm. I shivered a little as she slid her finger up the crack of my panties.

"You are one hot slut. And all mine." She started stroking my arms as she started walking me backwards. I backed slowly, completely under her power as she locked her eyes on mine. I didn't even flinch as my legs hit her bed and I sat down hard. She climbed up to straddle me and grabbed the back of my head, kissing me deeply. As our lipstick smeared together I natually started to attempt to control the kiss, but she squeezed against me and pressed me back, forcing me to submit. It was the most amazing kiss I've ever had. I was completely under her control and I loved it. She pulled away from me, gazing at me with lust filled eyes and whispered, "who's slut are you?"

She began biting my ear gently and breathing softly into softly as I whispered back, "I'm your slut Mistress..."

She bit harder and into my ear breathed, "and what will you do for me slut?"

As she moved to bite down hard on my neck I gasped, "anything you say Mistress."

She then slid off of me and pulled me to my feet. I leaned in to kiss her but she intercepted me with a finger, which she then pointed at the ground. I knew right away what my Mistress expected and dropped to my knees before her. As I knelt, looking up at her, Kate reached behind her and I heard a zipper just before her long skirt slid down her legs to puddle around her feet. Much to my surprise a long, think cock sprung from her crotch. It was a very real looking flesh colored and veiny strap-on.

"I think you know what to do slut."

I did indeed, without a second though I parted my glossy red lips and slid Mistress's big cock into my mouth. I could never have imagined doing something like this mere hours ago, but now I was only eager to obey. I began licking around the head of her thick cock and the slid it into my mouth, trying to suck Mistress as I liked to be sucked. I gazed up at her as I bobbed up and down and she grabbed a hold of my pig tails and started fucking my face, driving her cock into my mouth as she pulled my head towards it.

"Suck that cock you little whore. Get it nice and wet."

Her words encouraged me to suck and lick even more eagerly. Abruptly she pulled the cock from my mouth and I almost fell over leaning in to suck it back into my mouth. She jerked upwards on my pig tails.

"Up slut." I quickly got to my feet and she reached under my skirt and started stroking my cock through my panties. I moaned with lust as she leaned in to kiss me, biting onto my lower lip and keeping me like that as she forced me back into her dresser. Still half biting, half kissing me she reached down to grab my legs behind my knees. I sensed what my Mistress was after and helped her lift me up partially onto the low dresser. She leaned into me more heavily, pressing me back against the wall, lifting and spreading my legs apart. She moved one hand to a drawer and I vaguely heard a drawer open and close, drowned out by the sounds of our lust. I felt my panties being pushed to the side and something cool and slick sliding down my ass.

Mistress bit my ear and whispered, "time to take my little slutty princess's cherry."

I was so overcome by this incredible situation that it didn't even register. I simply moaned as I caressed Mistress's shoulders with my hands as I rubbed one leg along her body. I felt the head of her cock start to press against my hole and whimpered softly.

"Shhh, it's okay my slut, it only hurts at first."

I squealed and gasped as her cock popped into me but was silenced with another kiss. Mistress slowly slid her cock in and out of me, and the pain started to diminish and was replaced quickly by pleasure I had never imagined. Before long I was clutching fiercely to Mistress as she started to pound me hard and fast. I squealed. I moaned. I cried out. I heard myself screaming, "oh god yessss fuck me! Fuck me harder!"

"I knew you'd be my sissy slut, I knew you'd love getting fucked. Such a good little whore. You are mine now, you will beg for dick, mine, or any I will allow you to have."

"I'm your slut Mistress! OH god fuck me, i'm going to cum!"

"Cum for me you dirty slut, fill your pretty panties as you fuck my cock!"

I screamed out again, unintelligible this time as I felt my orgasm rip through my entire body, filling my panties with cum as I was ordered. Mistress slowed until she was just pressed against me with her cock all the way inside me. I clung to her, gasping.

"It was even easier than I imagined to turn you into my personal cock hungry sissy slut," Mistress laughed at me. "Such a good slut!" She caressed my face as I panted, then quickly stepped back, her cock popping out of me. I let out a small whimper at the empty feeling. Mistress chuckled at that.

"Time for us to get cleaned up, you've made a mess of us you naughty girl! It's time to parade you around so I can show off my new prize! What do you say princess?"

I wobbled on my feet and replied, "yes Mistress." That seemed an odd thing to say, but at this point I would've agreed to just about anything she asked after that amazing sex. Who knew getting fucked felt so good? Kate smiled knowingly at me, as if she could read my thoughts. I followed her into the bathroom to clean up, then to her vanity to fix our make up. When all was ready as Kate saw it she locked a collar around my neck, snapped a leash to it and tugged me with her towards the door.

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byprincess_nicole© 16 comments/ 229713 views/ 68 favorites

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by Anonymous

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by Bicdman0509/24/18


this story is hot as fuck. what the fuckis up with all these comments lol? this is for erotic fantasy. the author doesn't have to stick to preconceived relationship ideas that plague our reality. if youmore...

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by Anonymous07/19/18

Don't Need a Mistress

For me this would have been a very erotic story if not for the domination angle. Just don't understand why so many readers get turned on by that fetish. For those who feel the need...enjoy.

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