Caught

Caught by the Boy Next-door! (Mm, Sissy, Cross-dressing, Humiliation)

From Urban Dictionary – “A sissy is a biological male; who acts really feminine, slutty, horny, also really bimbo like, etc. They tend to be really submissive but not all of the time. Most sissies are into men, but some are into women, some are Bisexual or Pansexual as well. Most of them like to play with other sissies as well.” Fair warning. If you don’t like, don’t read it.

Note – This is a work of fiction, make-believe and sexual fantasy. It is not based on real people or actual events. You must be 18 or over to read these stories. The author does not condone any sexual activity among persons under 18 in real life. Also, the author does not condone unprotected sex in real life. It is OK to have fantasies, but turning a fantasy into reality can destroy lives. Don’t fuck with other people’s lives!

Michael Miller pulled the box marked ‘Christmas lights – broken!’ from the top shelf in the garage and carried it through the empty house to his bedroom. He set the box on the floor. Then, he stripped off all his clothes and dumped the contents of the box onto the bed. He smiled as he looked down upon his hidden stash. He picked up his favorite pair of panties and smoothly slipped them on. He felt the softness against his ass and felt the thin material cradle his balls. His cock immediately began to swell in anticipation. Wearing only his pink panties, he cleaned up the breakfast dishes in the kitchen, poured himself another cup of coffee, and contemplated his day.

Michael, or Michelle, as he called himself when dressed as a woman, was looking forward to a full day and a half in drag. It was Saturday morning and his wife had just left for the weekend to visit her mother. He couldn’t wait to get dressed and strut around the house all day wearing makeup, high-heels and a sexy dress. Then, after sexually edging himself for hours watching sissy porn and playing with his extensive dildo collection, he would finally masturbate once or twice, and then fall asleep wearing his soft, black, baby-doll lingerie set.

‘Michelle’ first took a warm, sensual, bubble bath and shaved his balls until they were smooth and hairless. He used his wife’s sweet smelling shampoo and conditioner on his hair and gave himself a facial. Then, after drying off, he applied lotion to his nearly hairless legs, his cock, balls and ass. He then curled and blow-dried his hair, brushing it slowly and lovingly, and applied some hairspray. He smiled as he put on his sexy black lace panties, thinking of his wife’s repeated encouragements to cut his shoulder length hair much shorter. He glued D-cup lightweight falsies to his hairless chest before putting on a matching bra.

After cooling off, he sat in front of the make-up mirror in the bedroom and expertly applied foundation, red lipstick, mascara, eye liner, eye makeup and blush, matching his skin tone. He blew a kiss to the sexy woman in the mirror. He then painted his toe-nails and applied glue-on acrylic fingernails to both hands before applying matching nail polish. He waved his hands in the air until they were dry.

Michelle put on a short, sexy, one-piece dress, and fish-net stockings. Then, he added the finishing touch; a pair of open-toe high-heeled shoes. He was proud of his small shoe collection. The black stiletto heels he was now wearing were his favorites, and they matched his bra and panties perfectly. He knew he was overly dressed for mid-day, but he didn’t intend to go anywhere. Being at home was not the same as visiting Las Vegas for a business conference, after all; he wouldn’t dare go out dressed like this in his own neighborhood.

Michelle turned on some dance music and strutted around the house, dancing, shaking his ass and sucking on one of his large, cock-shaped dildos. His cock grew hard in his panties. He edged himself for over an hour, playing she-male videos on the big-screen TV while he walked, twerked, wiggled his ass, and deep-throated his life-like silicone cock, knowing he had all day to cum and all weekend to play his favorite sexy games.

He strutted into the family room like a queen. He danced sensually in the bright daylight. He licked his lips, sucked his toy, and flirted with all the imaginary men gathered around him. Responding to a pretend wolf-whistle, he turned around and gave a long, sensual lick to the phallus in his hands before plunging it down his throat. ‘What a perfect day!’ Michelle thought to himself. He felt so pretty, sexy, and desirable. He twirled around in black dress and heels. Then he froze.

Michelle had sensed movement out of the corner of his eye. He quickly jerked his head around and looked again. He saw a human figure framed in the huge, glass, sliding-doors that exited onto their patio. It was the neighbor boy who mowed the lawn. He was watching his slutty behavior with a large, goofy grin on his face. In his hand was his phone. It was pointed at Michelle.

‘Shit! How long has he been there? What was the boy doing? He was taking pictures! Oh no!’ His mind raced.

Realizing his predicament, Michael Miller turned away to gather his thoughts. He saw the large dildo in his hand and quickly shoved it under the couch cushions next to him. He realized he was giving the teenager a nice view of his shapely ass.

He was screwed! ‘What should he do? Run? Hide?’ No, it was too late. He had to act, and quickly! He had to angrily confront the boy, chastise him for spying on him, and convince him it was all in fun, just pretend, a silly dress up game. And, he had to get those pictures!

Michael Miller marched to the door, his heels clicking smartly on the tiles, and forcefully slid open the door.

“Get in her, now!” he demanded. He decided to bluff the young man with feigned rage. “What are you doing out there Kevin? Trespassing? Spying on people? You are in so much trouble, young man!”

Kevin stepped inside. “Hi, Mr. Miller! Nice outfit! I was just getting ready to mow the lawn and wanted to tell you that you’ll need more gas soon.” Kevin smiled at Mr. Miller, chuckling softly at his girlish outfit.

“Give me that phone, and don’t you dare say anything to anyone. Kevin, I’m warning you!” He took a step towards the smirking young man, intending to scare him and snatch the phone from his hands. Michael suddenly realized the boy was taller than he was, even wearing stiletto high-heels. The boy was also more muscular than him, and stronger too.

Kevin took a measured step back and held out his opened hand in warning.

“Don’t come any closer, Mr. Miller,” he said.

When Michael took another step, Kevin then raised his fist and took a fighting stance.

“When was the last time you were in a fight, Mr. Miller? I’m on the wrestling team at school and I’m the fullback for the football team, so I’m in pretty good shape. To be honest, you look pretty weak, especially in your slutty little dress, so I wouldn’t try anything.” He smiled evilly. “Even if you somehow did take away my phone, I’ll have the cops here before you can take off your fucking panties.”

Michael realized he was beat. Kevin was right. He had never been in a fight and hardly ever worked out. He only dieted to keep himself thin so he looked good in his girly cloths. Kevin was much stronger than he was and would easily win a fight, even though the boy was much younger. He noticed the boys’ muscular legs, large chest, flat belly, and bulging biceps. He was at the boy’s mercy.

“Dammit, Kevin,” he said, ashamed and wishing he could crawl away and hide. “I need those picture deleted. Right now!” Michael pleaded.

“I don’t know, Mr. Miller,” Kevin said smiling, reveling in his complete victory, “What’s in it for me?” This was going to be fun, Kevin decided. He liked dominating smaller and weaker boys in school, and now, he had the unique opportunity to humiliate a grown man. The possibilities were endless.

“What do you want? Money?” Michael asked, as he considered how much cash would keep the boy quiet. “Look, I have a hundred dollar bill in my wallet I keep for emergencies. I’ll give it to you if you delete those pictures and never mention this to anyone. Deal?”

“Well, I don’t know…” Kevin began. “Seems like a picture of you wearing woman’s clothes is worth more than that. What if your wife saw it, or it somehow was sent to people you work with? You work at the Shaftman offices downtown right?” It would be a shame if they found out… They might think you are a sissy or something?” He smiled at Mr. Miller’s shocked expression.

Then he added, “Are you a sissy, Mr. Miller?” Kevin smiled, watching his victim squirm.

Michael mind whirled as he furiously considered how to answer Kevin’s surprising question. He always told himself he was not gay; that he only had a simple fetish. But Kevin’s question shook him. Michael couldn’t lie to himself; he dressed like a slutty girl to fantasize about attracting horny men. Secretly, he wanted to become a submissive, sexy woman. Yes, and even pleasure a man with a long, sensual blowjob, and fast, hard, fuck sessions. He had purchased cock-shaped didoes to practice sucking and fucking. He had a large butt-plug shoved up his ass this very moment. He was a sissy.

“No, of course not!” he finally said, denying the obvious truth. “This is only a simple fetish! I never…! I mean, just because I…” He looked down at his tight, black dress, high-heels, and red, pointed fingernails. He didn’t know what else to say.

“What about that, then?” Kevin asked, pointing to the couch. Michael turned as saw his eight-inch cock-shaped dildo sticking out from under the couch cushion. The light reflected off of the wet slobber that still glazed the fat-cock head.

“Err… I know!” he said, thinking quickly. “How about if we pay you more for mowing the lawn? How about that?” Michael said. “Then, you’ll get more money every week, and we can forget all about… this…,” he opened his manicured hands and gestured downwards to his dress, pantyhose, and heels. “OK?”

“Hmmm, I liked that idea,” Kevin said. “Double my pay, and I’ll delete the pictures.”

“Double?” Mr. Miller exclaimed.

“Double.” Kevin stated. “And the hundred bucks… or else”

Michael thought about it for only a moment. “OK.” It would be worth it, just for his piece of mind. “Now delete those pictures!”

“I think I need some insurance first.” Kevin said.

Michael looked at him expectantly. He was very concerned.

“Where is your wife?” Kevin asked. “She has to agree to pay me more too.”

“She out of town until tomorrow afternoon, visiting her mother,” Michael said.

“OK. Text the both of us, and tell her I’ve been doing such a great job, you are going to double my pay.”

“Then you’ll delete the pictures from your phone?” Michael asked.

“I promise,” Kevin said.

Michael walked to the counter to grab his phone. His heels clicked loudly. His butt plug itched, but he dared not scratch his hole.