A Halloween Tale: Candy or Consequences

M, Public, Crossdressing. Aaron was sitting alone at home, watching football re-runs as he usually did this time of year. He never went out for Halloween and often put up signs outside his house telling the neighborhood kids that he had no candy, so those little trick-or-treaters wouldn’t bother him late at night while he tried to sleep. It wasn’t that he disliked Halloween; on the contrary, but crowds, parties, and noise simply offended his senses. So he stayed quiet, enjoying his lonely serenity indoors.

Despite these reservations, Aaron was also a very avid cross-dresser, though only in front of one person: his mistress. He knew her first name—Hope—but because she was his Mistress, he had to call her “Mistress H” regardless of where they were or what the situation was.

This particular Halloween was about to become very interesting, as Aaron hadn’t planned for anyone to visit, yet suddenly there came a familiar rapping sound at the door. He rose from his chair in his dressing gown and trudged to the front entrance, expecting to shoo away some small costumed children. To his utter surprise, however, he opened the door to find a busty blonde bombshell dressed entirely in a kinky black leather catsuit and a matching black leather mask: Mistress H, holding several sports bags she had just retrieved from her car.

She briskly brushed past him with her bags and dropped them onto the floor before the television. She turned off the TV then faced Aaron, who stood jaw-dropped at the door in his dressing gown, the wind occasionally flapping inside it during the light breeze. “Close the door!” she snapped. He stuttered back to life quickly, closing the door and hurrying into his living room as she ordered him onto his knees.

He complied without hesitation, bowing his head toward the floor while she began her monologue. “Year after year, my pet, you have always been cooped up in your little house watching boring shows alone. This might be acceptable, but regrettably, you don’t even offer so much as a scrap of candy to the nicest children who approach your door… Tonight, all that will change, and this routine shall continue next year if you do not satisfy me this one. Now, first things first: get undressed, go upstairs, take a shower, and shave everywhere. Make sure you are perfectly smooth from head to toe—eyes down. Go on now; you have half an hour while I prepare your punishment.”

He looked up at his Mistress and nodded briskly before scurrying upstairs, nearly tripping over the trailing belt of his dressing gown which flapped between his still-quite-hairy legs. He reached the bathroom and climbed into the shower after removing his dressing gown and boxers. His mind raced with possibilities about what Mistress H had prepared for him on this auspicious night as he stripped himself of every bit of hair while rushing to meet his time limit. Just as he reached his upper thigh, he accidentally nicked himself with his razor, causing a wince as the hot water blasted against his supple, shapely body.

After attempting to dry off quickly, Mistress H yelled up the stairs, “Time is UP! Get down here NOW!”

Aaron rapidly wrapped his towel around his waist and rushed downstairs. His mistress stood in the kitchen doorway, riding crop poised in her hands. His hair was still dripping wet down the back of his neck, and his towel hung loosely off his waist, covering his manly hood.

She slapped the crop onto her palm and demanded he drop the towel to present himself for inspection spread-eagle. He hesitated slightly before complying. Recognizing this, Mistress H gave his ass-cheek a sharp crack with the crop as punishment. She then proceeded to feel around every part of his body for any stubble, probing and rubbing slowly from his face down to his legs. There she found his small razor cut, paused briefly to run her hand along it firmly (causing him to wince slightly), before continuing on to his ankles.

She rose from inspecting Aaron with a very stern look on her face and spoke sharply and directly. “Go and bend over onto the sofa. For every area of stubble I found, you will receive three hits from this lovely riding crop of mine. For that cut caused by your lack of care, I will give five hits. And finally, since you are not quite dry yet, you shall receive a further ten hits. Is that clear?” He mumbled a “yes mistress” before beginning to move toward the sofa. Before he could get far, she stopped him.

“I didn’t quite hear you; say it LOUDER,” she commanded.

“Yes Mistress!”

“Much better.” She said this while pushing his torso over the arm of the sofa. He began counting the strokes in his head as each hit landed, quickly reaching the 15 he had calculated. Then, tears rolling down his face, she sharply rested upon a final total of 24 strokes. This made him wonder where he had been negligent about his shaving—though to no avail, as he had no idea which areas were missed, but Mistress did know, and that was all that mattered.

“Now dry yourself completely,” Mistress said, placing the hair-drier on the table and throwing his towel at him before disappearing into the kitchen. “I don’t want you to damage your wig and new Halloween outfit.”

Aaron hurried to dry himself before she returned, rubbing as fast as he could while blasting his short brown hair with the bright pink hair-drier Mistress had provided.

A few minutes later, she returned from the kitchen brandishing perfectly white panties with more frills than most people can imagine, along with a bra that was just as frilly and seemed weighted. Aaron knew these well; they were his own. The bra had significant weight because it featured large, full breasts built into them. Mistress laid them on the table next to him before instructing,

“If you’re dry enough, put these on, now!”

He jumped at putting on the panties first, nearly falling over after almost missing the second leg hole but managing to stay upright. As his mistress vanished back into the kitchen again, he had just grabbed the bra and began fumbling around his back to attach it comfortably. When Mistress appeared once more this time carrying a terribly frilly black-and-white maid’s outfit and a rather large ball gag that he imagined might not even fit in his mouth—nevertheless, she carefully laid them on the table and left him to dress while she tottered off into her smooth, sexy catsuit.

He watched her go and was sure she spotted him looking but certainly didn’t make it obvious. He quickly hurried himself into the dress with its biggest built-in petticoat he had ever worn. He also noticed the small straps at the bottom of the dress meant for stockings. As he put on the ball gag—not surprisingly completely trapping his mouth—Mistress once again appeared from the kitchen, bringing black lacy stockings and a pair of prissy black 6” high heels with small locking buckles around the ankle.

Mistress insisted she would help him with these final touches, since such a big sissy surely couldn’t do it on his own. Pouting while saying this added more weight to his current humiliation. She slipped on the stockings for him, clipping them into the built-in suspenders before rubbing her hands all the way down his sissy legs, causing him to gasp slightly at the surprising amount of pleasure it gave him. Then, just as he calmed from receiving the second stocking’s attention, she locked his heels in place. With no escape possible, he stumbled to his feet.

“Oh how cute,” Mistress said, standing there proudly admiring her confused and aroused little sissy tottering on his small heels before adding,

“Hmmmmm, just two more little presents for you, and you’ll be absolutely perfect.”

She dashed back into the kitchen.

She returned with a triumphant air, carrying a long blonde wig and a white mask that had only very small eye-holes cut into it. She quickly placed the mask over his face, then after some minor tucking and wrangling, managed to secure the luscious blonde wig on him. “Go ahead and look in the mirror, my little sissy maid,” she said, pointing toward the full-length mirror on the back of the kitchen door. He slowly teetered over, bracing himself against various pieces of furniture, until he finally saw his reflection. The large wig hid most of his broad shoulders, while the dress and bra created a delicate female physique that looked so appropriate for a maid. The stockings and shoes completed the outfit perfectly, and then there was the mask—a pale white porcelain piece with an antique look. It featured exaggerated full red lips on the front, along with massive eyelashes and eye-shadow surrounding the tiny eye-holes, allowing him enough vision to move around capably. If his mistress could have seen his expression, he would have looked blissful, though she likely guessed as much. She hurried him toward the door with her next instructions: “Now you must go outside your house and take down all those signs telling little children not to come by for candy.” He shuffled out nervously, peering through the tiny eye-holes to ensure no one spotted him. His mistress dragged him into the glow of the streetlight before surprising him with a small glowing plastic pumpkin. “When you’re done taking the signs down,” she told him, “put this little lantern on your fence so that the kids know you’re a generous little sissy. I’ll be waiting inside for when you’re finished.” Mistress strolled back into the house and slammed the door shut behind her while Aaron stood in the cold air, panicking slightly. To prevent further humiliation, he hurriedly took down his signs and placed the glowing lantern on the fence-post before scuttling back inside, his heels clicking with each tender step. Once inside again, his heart was thumping harder against his breasts, making him feel light-headed. He went into the living room to try sitting down, but there on the sofa, holding her crop, sat Mistress. She rapidly gave him a swat across his thigh with it. “That,” she said, “was for looking at your mistress without permission. Now I have one last thing for you.” Grinning as she spoke, she stood up and retrieved what seemed to be a pair of full-length opera gloves from a bag on the table. Attached to one glove was a bowl, positioned in a fixed pose like an arm serving something out. He noticed that the other glove was also in a fixed pose but remained simply straight. She slipped his arms into them, locking them tightly in place. As he began to get comfortable, Mistress pulled lots of sweets and candies—jelly beans and all sorts of sugary items—from the bag and dumped them into the bowl attached to his arm. For a moment, he stood there surprised, trying to regain his balance. He managed to compensate for the weight of the sweets but found it difficult with one arm fixed in the serving position and the other permanently straight out, unable to bend at the elbow. No sooner had he gotten used to the arm bindings than the doorbell rang. He looked around in panic toward his mistress, who simply said, “Well, go on, answer it!” He hesitated again but managed to will his sissy-heeled legs totter toward the door. Standing before him were about four eight-year-old children dressed in cute little costumes, all waiting at his doorway. In unison, they yelled, “TRICK OR TREAT.” Not knowing what else to do, he bent over slightly to offer the sweets from the bowl. They reached up, nearly touching it, causing him to almost topple over as he lost his balance again. Quickly after, they all scurried off yelling, “THANKS MISSUS!” He barely managed to close the door with his straight fixed arm since the bowl completely occupied his other hand. If not for the mask hiding it, his face would have been bright red, and once more, his heart was nearly jumping out of his chest after this brief encounter. But the night was still young, and there were certainly more than four trick-or-treaters in this neighborhood. TO BE CONTINUED