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Sissy Stories - Caught by the Boy Next-door!(Sissy, Mn, Cross-dress, Humil)

UndeniableUrges · 1396

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Offline UndeniableUrges

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Sissy Stories - 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.”

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 bed. 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, babydoll 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. He also had a little trouble texting properly with his bright red press-on fingernails getting in the way. This was a small price to pay, he decided.
“What’s your number?” Michael asked his young neighbor, who slowly responded. After a very long moment he pressed ‘Send.’

“There, now delete those pictures!”

“The hundred bucks first.”

Fuming, Michael stomped to his bedroom to retrieve his wallet. As he returned, his phone chirped. Then Kevin’s phone chimed as well.

“Debbie thinks paying me more is a great idea,” Kevin said, reading Mrs. Miller’s text. “That’s your first name, Michael? I bet you like Michelle better though.” He pocketed the hundred dollars. “I always did like your wife, Michelle, she’s so fucking hot!”
“Please leave my wife out of this. Delete, them please, now? You promised! Please, Kevin!”

Kevin gloated a moment and then showed Mr. Miller the pictures on his phone. Michael watched as Kevin displayed photo after photo of Mr. Miller in drag and then made an exaggerated effort as he deleted them. A half dozen photos were displayed before they disappeared and Kevin finally put his phone away. “There, happy now, Mr. Miller?”

“Yes!” Michael was so relieved. You could definitely tell the pictures were of him in drag, even if some were blurred by his dancing. However, the pictures clearly showed this room, his house, and the pictures of him and his wife on the shelf behind him. Debbie would have divorced him for sure! He just had to get Kevin out of his house, get rid of all of his girl clothes, and pretend this never happened!

Just then, Michael heard Kevin’s voice again. “Oh my Gawd! I can’t believe it! Mr. Miller is dressed like a chick and dancing around like a fucking slut!” Michael looked at Kevin’s face – his lips weren’t moving. The voice was coming from Kevin’s phone!

“Look, he’s sucking a fucking rubber cock!” Kevin’s voice nearly chocked, suppressing laughter. “What a fucking weirdo!” Kevin showed Mr. Miller the image on his phone. The image showed Michael dancing and sucking on his rubber phallus. “I bet he shoves it up his ass too!” Kevin’s voice continued.

Mr. Miller knew what happened next. He watched himself turn around, notice Kevin at the door, pull the rubber cock from his mouth in panic and stuff it under the cushions. He then heard his own voice confronting Kevin and hearing Kevin call him ‘Mr. Miller.’ The video ended just after he threatened Kevin.

“Delete it! Delete it, Kevin! We had a deal!” Michael pleaded. Oh shit this was terrible. There was no doubt the video was of him. He could never deny it now!

“Well, I agreed to delete the pictures…,” he said smugly, “But, we never mentioned anything about the video. Wanna see it again?” Kevin played it again. Mr. Miller tried to grab the phone but Kevin held it up high, laughing at his predicament.

“Now, now. Behave yourself, Michelle, or I might have to send this to your wife. Thanks for giving me her phone number, by the way.”

“Kevin, please…., please don’t do this. Don’t ruin my life. Please don’t make me suffer anymore…” Mr. Miller looked like he was about to cry. “Haven’t you already humiliated me enough?”

“Oh, poor little girl gonna cry?” Kevin taunted.

“Oh, please?” Michel added again, hoping to convince Kevin by any means necessary. Even if he had to beg and cry like a baby. “I’ll do anything! Just delete that video!”

“Oh, OK,” Kevin said, as if upset his fun was over. “If…, you do one more thing for me…, I’ll delete this video from my phone.”

“How can I trust you?” Michael said. “You could have more videos and pictures for all I know.”

“I promise, if you do one more thing for me, I’ll delete this video from my phone. There no more images or videos or any likeness of you on it. It is the last one.” He smiled. “Cross my heart and hope to die.”

“On your mother’s grave?”

“On my mother’s grave.”

Michael had to trust him. Kevin appeared to be honest. Right now at least.

“OK, what do you want now, more money?” Mr. Miller asked.

“Well,” Kevin began, “It’s like this. When I first saw you dancing, I thought you were a real girl.”


“You make a very pretty girl, Mr. Miller, I mean Michelle…,”

Michael waited, tapping his pointed toes on the floor impatiently. He did not like where this conversation was going.


“And, I was watching you dance, and I started to get a little horny…”

Mr. Miller’s eyes widened in shock. Was this young punk really going to say what Michael hoped to god he was not going to say?

“Get to the point, Kevin!” Michael said, his voice rising in anger and fear. He started to tremble. “And you better not…” he managed to squeak before he was loudly interrupted.

“I want a blow-job.”


“Right now.”


“Suck my cock, right here, right now, or I send this to your wife.”

Michael crossed his arms under his fake breasts in an act of defiance and to stop himself from shaking. Unknowingly, watching his fake breast press against his tight dress only inflamed the boy’s desire.

Kevin began pressing buttons on his phone. “There. The video is attached. ‘What a little sissy-faggot you have for a husband, Mrs. Miller.’” he read as he typed.

“Ready? One…, two…, thr..”

“STOP!” Michael’s lower lip trembled. Suck this boy’s cock or lose his wife and marriage..? And, he’d probably lose his job as well too!

“I’ll do it,” Michael whispered softly.

“Do what?” Kevin taunted, “I want to hear you say it.”

“Suck your cock,” Michael stuttered. “I said I’ll suck your cock, but you have to delete that video!”

“I said I would, didn’t I?” Kevin said, and added, “Don’t ya trust me?” He smirked again.

Kevin pulled off his t-shirt and quickly kicked off his shoes. He plopped down on the couch. The dildo fell from its partial concealment. It hit the floor, bounced once, and rolled for a moment. Kevin looked at it and laughed.

Michael’s lower lip trembled again. He bit his red, painted lip and willed it to stop.

Kevin started to pull down his short, but stopped. “No, you do it!” he said happily. “I want to pretend you are a fucking slut who wants my cock. Get it out and start sucking it!” He jumped to his feet, kicked the dildo out of the way and stood in front of Michael menacingly. “On your knees, bitch!” he sneered.

A tear fell from Michael’s face. He slowly fell to his knees, totally defeated by this young, alpha male. He glanced up at Kevin, to beg for mercy once again. His butt-plug started to slip, and he clenched his ass-hole tightly to pull it back in.

“Don’t look at me!” Kevin spat. “It ruins the fantasy if you look at me. Just suck my cock like a fucking slut. I swear, if you look at me again, I’ll send this mother-fucking video! All I have to do is press the button!”

Michael sniffed, his nose was running and his throat was tight. He pulled his eyes downward and after quickly glimpsing Kevin’s muscular chest and flat abs, he looked straight ahead to find himself staring at Kevin’s jogging shorts,. He looked down to the floor. The tile made his knees ache. What had he gotten himself into to? How could he had been so careless?

“Listen, I want a great blow-job from a total, cock-loving slut – it turns me on, OK? Like wearing women’s clothes and sucking cock gets you turned on. I don’t want you to ruin it by looking at me. Ever. Just look at my fat, fucking dick.

“And, if I ask if you like my cock, you say, ‘Yes, Kevin, I like your cock.’

“If I ask if you are a total cock-whore, you say ‘Yes, Kevin, I’m a total cock-whore.’

“Whatever I say to you, you say, ‘Yes, Kevin, and repeat it back to me, with feeling - like you mean it! Got it?”

“I…, uh…, yes…?” He almost started to glance upwards, but quickly looked down at his pantyhose encased legs and knees. He would probably ruin these stocking, he thought sadly.


“Huh? I mean, ‘Yes, Kevin.’”


“Uh, and…? And I’ll repeat what you say…, with…, feeling!” He added. Whatever gets the jerks to finish sooner, Michael thought, and get that video deleted forever!

“Good, now, get busy, whore, and, you better do a good job, or else…,” the young man threatened.

“Yes…, Kevin,” he choked. “I’ll.., do a good…, job!” he repeated, staring at the floor.

“And if I even think you and your faggot eyes are trying to look at my face, I’ll fucking send the video!”

Michael wanted to burst out crying, but he knew it wouldn’t help. Resolved, he decided to do what he had to do and trust his young neighbor would keep his word. He reached up to pull down Kevin’s jogging shorts.

“You like cock, don’t you, Mr. Miller?” Kevin prodded.

Michael kept his eyes straight ahead. It was a good thing he was a little near sighted. He knew Kevin has his finger on the send button, ready to expose his secrets.

 “Yes…, Kevin…, I like cock.” Michael said, with as much feeling as he could muster, under the circumstances.

Michael gripped Kevin’s shorts and slowly pulled them downwards. Ashamed and apprehensive, he tugged the shorts down a little more. Michael could see the hefty bulge of Kevin’s penis through the thin shorts and found himself marveling at the soft, brown, pubic hair that grew from his crotch. He pulled the cloth down further before noticing Kevin’s boxer shorts and jogging shorts bunching up at the base of his penis. Impatient, he tugged firmly and Kevin’s virile, young cock sprang out.

Michael couldn’t believe it! Kevin’s cock was already bigger than his own penis, and it wasn’t even hard! He finished pulling down Kevin’s shorts and underwear and pushed them to the floor. When Michael leaned forward to pull the shorts all the way down, it forced his face to be mere inches away from the boy’s groin. He could smell fresh soap. At least Kevin had showered this morning, he thought. And, while Michael was feeling very ashamed and totally humiliated, part of him looked forward to actually sucking a cock. After all, he had been fantasizing about it for years. This wasn’t gay, he reasoned, he was being forced to do it. It’s not like he went do downtown gloryholes to suck cock in his spare time.

Kevin kicked off his shorts and waved his cock in front of Mr. William’s face.

“Do you like my cock, Mr. Miller?” he taunted.

“Yes, Kevin.., I…, like your cock.” A strange feeling washed over Michael. He realized he did like Kevin’s cock; and his balls too. Kevin’s cock was admirable, almost perfect for a boy his age. Hell, it was perfect! Circumcised, with a large, flared, reddish-pink cock-head. The shaft was long and thick with a big set of testicles hanging beneath it. His crotch and balls were hairy, but not too hairy. It put Michael’s own smaller cock and to shame. No wonder the boy was so confident!

“Lick it.” Kevin demanded.

“Yes, Kevin.” Michael said obediently. He stuck out his tongue to lick Kevin’s cock-head. He had to chase Kevin’s still soft cock about with his tongue, he pushed it around a bit with his face, and soon he was able to give it a big, wet lick from the underside of Kevin’s frenulum and across the bottom his flared glans. Michael felt oddly pleased as he saw Kevin’s cock swell a bit.

Michael realized it was his first taste of cock. Maybe his last…, or maybe not…. It tasted so much better than his rubber one. It was real.  Spongy and salty and it smelled so good.

“Does my cock taste good, Mr. Miller?”

“Yes, Kevin, your cock tastes good,” he admitted.


More silence.

What was Kevin waiting for? Michael dared not look up at him. Why wasn’t he making him lick it again, or forcing him to suck it? Ah-ha! He knew what Kevin was waiting for. Kevin was waiting for him! He said he wanted Michael to beg for it! Fine. If that is what it takes to get this whole ordeal over with. Besides, he always wanted to suck a real cock, he might as well enjoy it. After all, it might be his only chance.

“Uh, Kevin, may I lick it some more?”


“Kevin?” he asked again, and added, “Please, may I lick your cock again?”

Why was he denying him? Didn’t he want his cock sucked?

“You can lick it again, but only once!” Kevin teased.

Michael quickly reached out his tongue and licked all around Kevin’s cock head, making his single lick memorable. Kevin pulled away all too soon.

“Kevin? Don’t you want me to…? I mean, can I…, please?”


“Beg for my cock, Mr. Miller.” Kevin giggled.

How humiliating this all was to Michael! But then he remembered Kevin wanted him to be a slut, a total cock-slut! He could do it. He could beg for it. He could act like a cock-whore, since he had to. Besides, he had a lot of practice in his bedroom with his rubber cock up his ass, acting like a sissy-cock-sucking-ass-fucking-slut. All the better to get this over with! He decided to whatever he had to get this ordeal finished. If he went along with it and encouraged the boy’s fantasy, it would be over that much sooner.  

Michael raised his voice higher, trying to sound feminine. “Please let me lick your cock, Kevin. I love it! Oh, yes! I love your cock, Kevin. And… and I need it! Yes! I need your pretty cock! Kevin, please let me lick your big, fat cock again. ... I want it Kevin, Please let me have it?” he begged. As he spoke the words, Michael realized he did want this boy’s cock. His own little cock was rock hard in his panties.

“Tell me why you want to lick my cock again.”

“Oh…! Uh…, I want to lick your cock because you have a big, hard cock and I’m a slut; a cock-slut! And, I want to taste it again! I love the taste of your cock, Kevin. I want to feel it get hard on my tongue and see how big it is. I want to suck it too, I want to suck your cock and lick your balls, Kevin!”

“Man, you really are a cock, craving faggot, Mr. Miller, I mean Michelle!”

Michael jerked at the mention of his real name. He almost looked up again.

“Close your eyes and raise your face. I want to see those pretty cock-sucking lips, but no peeking!”

Confused, Michael closed his eyes and turned his head upwards.

“Tell me your name slut, and tell me you are a cross-dressing-cock-sucking-faggot.”

A little confused, Michael did as he was told. He was in this far already. “Uh, my name is Michael Miller, and I’m a cross-dressing-cock-sucking-faggot.”

“Good girl, Michelle,” Kevin snorted. “Now, tell me your name is Michelle Fuck-Face, and you are a cock-loving cum-slut!”

Getting into Kevin’s fantasy now, Michael smiled and said, “My name is Michelle Fuck-Face, and I am a cock-loving cum-slut!”

“You can suck my cock now, fuck-face.”

“Thank you, Kevin,” he said, and meant it. Michael reached out and grabbed Kevin’s cock at the base. He lifted it up until it was pointing at his face. He began to lick it up and down and all over the sensitive head. Michael was thrilled when Kevin’s cock began to get hard. He opened his mouth, licked his lips, and put the cock-head in his mouth. He closed his eyes and made love to this bully boy’s cock. He licked and slurped and suckled and swallowed, reveling in the thrill of sucking his first cock.

“Oh, yeah!” Kevin moaned. “Damn, Michele. You are a good cock-sucker! Suck it some more! Suck it good, or else! Suck my balls too!”

Michael did just that. He licked Kevin’s cock down to the base and then crawled under his balls to slurp on them too. He knew they were full of hot, teenage splooge, but just then, he didn’t care. He briefly considered the sperm inside of the balls he was sucking might end up in his mouth, but it didn’t faze him. He was too focused. He made love to Kevin’s cock as best he could. Now, Kevin was hard. Rock hard. The boy’s cock-head barely fit in Michael’s small mouth.

Finally, Michael paused and opened his eyes again. There in front of him was a magnificent piece of flesh. It was straight and pointed upwards. The veiny shaft pulsed and throbbed with need. Kevin’s cock-head was fat, and flared, now a deep purple color. He couldn’t take his eyes off of it.

“Do you like it, now that it is all big and hard?” Kevin asked.

“Yeah!” Michael gushed. “I mean, yes, Kevin, I like it. I like it a lot!”

“Are you glad you seduced me?”

Huh? Is that how he wanted to play it now?  Kevin must be feeling guilty and was trying to blame him for this mess. “Yes, Kevin,” he sighed, “I’m glad I seduced you.”

“Do you like seducing little boys and sucking their cocks?”

“Yes, I love seducing little boys and sucking their cocks,” he said, all too easily.

“You are a dirty old man, Mr. Miller. You make me feel all funny inside. Are you are going to suck my dickie again until I shoot my stuff?”

“Yes, Kevin,” he said, wondering at the boy’s odd behaviour. “I’m going to suck your dickie again and make you shoot your stuff.” Michael went back to work on Kevin’s cock.  He gulped the hard, thick shaft nearly to the base. Thankfully, he had a lot of practice on his rubber cock. He slurped on Kevin’s cock and wrapped his lips around the sensitive glans. He tickled his balls and began to deep-throat Kevin’s cock, sucking his shaft deeper and deeper, until Kevin’s balls rested on his chin. Again and again, over and over. Michael bobbed his head up and down. He twirled his tongue around Kevin’s wide, flared glans. He felt Kevin’s cock swell even more in his mouth. He heard Kevin groan.

The boy’s cock suddenly erupted, coating the inside of his mouth with warm, thick, salty cum. Before he could comprehend what was happening, another, even bigger blast coated his tongue. Michael’s eyes grew wide. He swallowed, nearly choking on the copious amounts of teenage splooge. Another blast of sperm and then another! He started to gag. It was more than he could swallow! He pulled his mouth away and felt another blast and then another splash on his face and splatter his eyes. He clenched his eyes tight and felt another warm strand land on his forehead and stream down to his cheek. He dared to peek, and saw Kevin jacking off his cock in front of him. Another shot landed on his lips. How much more can he shoot, he wondered?

Finally, the boy finished, and squeezed the last few drops out of his cock and let them drip onto Mr. Miller’s forehead.

“You are a great cock-sucker, Mr. Miller! Let me look at you, but keep your eyes closed!” Kevin breathed. “Let me see your face!”

Michael turned his head upwards again. He felt Kevin rubbing his spent, slimy cock on his face, cheeks and lips.

“Do you like my cum?” Kevin asked.

“Yes, I like your cum, Kevin,” Michael said, tonging the gaps between his teeth and gum and then realizing Kevin’s cum was much sweeter than his own. Eating his own cum was one of Michael’s many shameful activities. And, Kevin’s sperm did taste pretty good. Even better than ‘good,’ he decided.

“Is it delicious?” Kevin snickered.

“Yes, your cum is delicious, Kevin.” Michael said, actually meaning it. He was tasting another man’s cum! He felt some cum dripping from his lips and automatically licked it with his tongue.

“Are you a cum-slut, Michelle?” Kevin taunted, giggling. “Are you a cum-loving, faggot, cock-sucker?”

“Yes, I’m a cum-loving slut; a cock-sucking, ball licking, cross-dressing, sissy, faggot, cum-dump.” Michael didn’t care any longer. His ordeal was over. He would say anything now to get the boy to leave. His tongue searched for more sperm.

“Thanks, for the blow-job, Mr. Miller! It was great!” Kevin slapped his cock firmly across his neighbor’s pretty face, as if marking his territory.

“Can I open my eyes and get up now, Kevin?” Michael asked humbly. His knees hurt. His butt-plug itched. He needed to wipe the sperm off of his face.

“What the fuck do I care, faggot?” Kevin laughed, then snorted. “You look like a fucking porn star, Mr. Miller! Ha ha ha ha!”

Michael stood up on wobbly knees. He looked down. He knew it; his pantyhose were torn at the knees. It was so embarrassing to buy more at the drug store. It was as if the clerks knew they were for him.

“OK, now delete the video, like you promised,” Michael asked eagerly.

“OK, OK! Don’t get your panties in a bunch!” he snickered. Kevin already had the phone in his hand. Michael waited while Kevin pushed buttons. He watched as Kevin deleted the video.

“Wheew!” Michael breathed.

“Thanks for the blow-job, Michelle.”

“You’re welcome, Kevin,” he said automatically, then felt like a fool. “I mean, let’s just forget it ever happened, OK?”

“Sure, Michelle. But hey, can you do me one more favor?” Kevin asked.

“I doubt it, Kevin,” he grumbled.

“Will you wear your sexy clothes while I mow your lawn, and then you can pay me, dressed up all pretty and sexy like that again?”

“We’ll see, now get out of here and leave me alone, please?”

Kevin collected his shorts and underwear and went out to mow the lawn, chuckling to himself.

Michael breathed a sigh of relief as the back door closed. He took off his high heels, noticing the scuff marks, and also picked up his cock-shaped dildo. He walked into the bathroom, dejected but oddly satisfied. He looked in the mirror and was shocked to see his cum covered face and smeared lipstick. His appearance reminded him of a cheap whore after a long night of hot sex.

“Oh, Michelle, what have you done?” he sighed to himself. Then, he grudgingly smiled, reflecting on his recent fate.

“You are a slut, Michelle. A cock-sucking, cum-dump slut, aren’t you?” he said to his reflection.

He looked for another moment, hesitated, and then ran a long fingernail into the thick gob of teenage splooge stuck to his cheek. He smiled and placed it into his mouth, tasting another male’s sperm once again.

“Yep, I’m a cum-slut,” Michael said, then cleaned the rest of the cum from his face and slurped it up. No sense in wasting it, he reasoned. Besides, he would never get another chance. He savored the last drops, smacking his lips appreciatively.

The thrill of his recent expectance and the fresh taste of boy cum on his lips made his cock hard in his panties. He had been edging all morning and needed relief. He was even hard while suffering Kevin’s abuse, and was thankful his panties and dress hid his arousal. His panties felt tight and confining. He reached up under his dress and pulled his panties aside, letting his hard cock free.

He considered removing his itchy butt-plug, but liked the feeling of having his ass stuffed as he came. Her readjusted it and then washed his manicured hands before smearing his pre-cum over his cock-head. He began to stoke himself gently.

Michael walked into his bedroom, intending to jack-off on his bed, but the growing sound of the lawn-mower caused him to pause and look out the window. There was Kevin, smiling and happily mowing the lawn with his shirt off. And, why wouldn’t he be smiling, Michael thought, after the wonderful blow-job he had given the boy. Probably the kid’s first blow-job ever, he realized. Michael stared at his strong arms and bare muscular chest, as he admired his build. He licked his lips, still faintly tasting the boy’s sperm tinged with lipstick. He glanced at Kevin’s crotch, now knowing what was hidden within his shorts.

He relived Kevin’s thick cock slapping against his face. He remembered the taste and scent of his freshly washed balls. He recalled the hard spongy texture of the boy’s cock within his sucking mouth.

He began to fantasize about Kevin as he stroked himself with his index finger and thumb.

“No, Kevin,” he said aloud, “Please, don’t make me suck your cock again!”

His little cock hardened even more.

“Yes, Kevin,” he breathed, talking to his imaginary teenage lover, “I know I’m a cock-sucking, sissy.”

“Yes, Kevin,” he said, “I love your big fat cock.”

“Oh, Kevin, please let me suck your cock again!”

Michael began to suck on his dildo as he stroked himself, slowly going faster and faster.

“What, Kevin? What did you say?” he said, watching Kevin mow and actively lusting after the dominating boy and his thick teenage cock.

“My ass?” Michael said. “You want to fuck my ass, Kevin?” Michael moaned and stuck out his butt, wiggling it back and forth.

“Please don’t fuck my ass!” he whined, stoking his little cock, “Your cock is too big for me, Kevin!”

“OK, OK! Just do it! Put it in and fuck me! Hurry!”

“Unnnh! Oh! Unnnh! Oh, yes, do it!” he said louder, “Fuck me, fuck my ass!” He imagined the naked Adonis gripping his shoulders and thrusting repeatedly as he took his anal virginity.

Consumed in his fantasy, he shot his stored up cum forcefully against the bedroom wall. His face contorted as he came. He looked out the window at the object of his desire and saw Kevin looking directly at him from the yard with an amused sneer.

“Unnngh!” Michael moaned as his orgasm rolled over him. He shot another blast onto the wall as he ducked from the window, cupping his spurting dick with his other hand so he wouldn’t make a further mess.

Humiliated at being discovered, but surprised at how horny it made him feel, he finished his orgasm and stood trembling on shaky knees, his spent cock dripping and his cum cooling in his palm. He dared to peak out the window and saw his lawn-boy walking away from him, pushing the mower for another pass. Even in his exhausted and humiliated state, he admired the boy’s firm ass as he worked.

Walking into the bathroom once again, Michael slurped the cum from his hand and squeezed his cock for the last few drops. He took some tissues and wiped down the wall. Then, he gently wiped his face, brushed his teeth, and began to reapply his make-up.

It wasn’t for Kevin sake he was fixing his make-up, he told himself, it was for his own. He wasn’t going to let some obnoxious kid keep him from having his cross-dressing fun. He blew a kiss at his reflection, knowing he looked sexy as hell. No wonder the kid wanted him! He’d give the boy one last glimpse of his pretty face and hot body, he decided. He fussed with is make-up a little more, lying to himself that he was not trying to look good for his teenage neighbor boy stud. In a strange way, he was almost sad their tryst would be a onetime event, as he caught himself daydreaming about another engagement.

“Nope, It’s best he forgets about me,” Michael said out loud, knowing it would be a long, long, time and many jack-off sessions, before he forgot about Kevin and his gorgeous teenage cock.

He heard the lawnmower turn off and knew Kevin would soon be knocking on the back door to get paid. As the spinning blades slowed down, he heard Kevin putting the mower away in the shed and close the door with a loud slam.

Michael waited nervously, tapping his pointed shoes on the floor, money in hand. “Double pay, just for mowing the lawn?” he said to himself. “Hell, he should be paying me, after the great blow-job I gave him!” He smiled, proud of his first-time cock-sucking skills.

He watched Kevin walk to the back door, tired and sweaty from exertion. Michael slid the door open a bit, intending to press the money into Kevin’s palm, and then give him a sexy sounding ‘Thank you’. But, Kevin pushed the door open and stepped inside.

“Here you are Kevin, thanks for mowing my lawn!” Michael said nervously, in a high pitched, girlish, voice.

“Damn, you look even prettier, Michelle,” Kevin said, while lusting after Michael with his eyes. He stared at the cross-dresser, first looking at his shoes, then his nylons, to his crotch (no discernable bulge) then to his chest and pretty painted face. He looked at Michael’s red, cock-sucking lips and said, “You are too damn sexy to be a guy.”

“Thank you, Kevin,” Michael said, blushing. “Here, please take your money and go.”

Kevin took the wad of cash and shoved it into his pocket. With his other hand, he gripped Michael’s wrist. He admired Michael’s painted fingernails and delicate hands.

Michael tried to pull away. “Please,” he said, pleading with the boy.

“I want another blow job, Michelle.”


“And, I want a blowjob every time I mow your lawn from now on. Before and after.”

“No, Kevin, we had a deal! One time only. Now, please leave!”

“Sure you won’t reconsider?” He slowly pulled his phone from his pocket. He opened it, flicked his finger a few times and smirked, holding up the phone so Michael could see the video playing. Kevin’s familiar voice began emanating from the small device.

“Oh my Gawd! I can’t believe it! Mr. Miller is dressed like a chick and dancing around like a fucking slut!”

“You promised to delete that!” Michael whined.

“And I did. I promised to delete your pictures and video from my phone, and I did! But, I have terabytes of data storage on the cloud. I still have all the pictures too.” He fumbled with his phone. “Oh, and this too….”

Michael heard his own voice again “Uh, my name is Michael Miller, and I’m a cross-dressing-cock-sucking-faggot.”

Kevin showed him the phone. Michael saw his own make-up wearing face, in extreme close-up, with his eyes closed, saying, “My name is Michelle Fuck-Face, and I am a cock-loving slut!”

‘Damn-it! What a fool I was,’ Michael said to himself, as his whole world crashed around him. ‘That’s why he made me close my eyes! How could I have been so stupid?’

“I got it all, faggot. I have the whole video of you begging for my cock and then sucking it! Then, admitting that you seduced me and that you like to suck on little boys’ pricks! So, unless you want to go to jail for the rest of your life, get on your fucking knees and suck my cock! Now! You are such a fucking idiot, letting me film you. What a moron! Start sucking!”

Michael Miller shed a tear as Kevin pushed him to his knees. He looked up to see his antagonist gleefully filming him once again. He realized there was no sense fighting anymore. He was at Kevin’s mercy and could only try to please him; Kevin owned him and could make him whatever he wanted to anyway. His only hope was that Kevin might someday get a girlfriend and eventually tire of him. But, he knew he lived next door to a horny teenage boy. There was no telling how many times Kevin would make him suck his cock, or worse…. He could get through this, Michael told himself, as long as Kevin kept this between only the two of them.

Disheartened and humiliated, he pulled down Kevin’s shorts and underwear. He noticed the dampness on Kevin’s balls. He could no longer smell the delicate fragrance of soap; only a sweaty male’s funky ball-sack. He stared at it dejectedly.

Being impatient, and wanting his cock sucked again, Kevin grabbed Michael’s head with one hand and pulled his face into his crotch. Michael quickly opened his mouth to accept Kevin’s cock. He could taste the stale sperm and sweat. Resigned to his fate, he sucked on Kevin’s swelling cock-head and then lapped at his sweaty balls while he stroked Kevin’s thickening shaft. He felt himself get hard in his panties.

“Do you have any beer in here, Michelle?” Kevin asked.

Michael shook his head no, looking up at Kevin while keeping his cock in his mouth, as he moved his head from side to side. He then stuck out his tongue and licked around Kevin’s cock-head before sucking Kevin’s cock once again.

“Get some before I come back tonight,” Kevin grinned. “And wear something really slutty for me.”

Michelle considered his options.

‘Maybe my school-girl outfit, or that pretty red dress with the slit up the side? That would go great with my red high-heels… Oh! And my new lacey red panties and bra! Perfect!’

© Copyright Undeniable Urges, 2020. Unauthorized use and/or duplication of this material without express and written permission from the author is strictly prohibited. Excerpts and links may be used, provided that full and clear credit is given to Undeniable Urges, with appropriate and specific direction to the original content.
« Last Edit: August 16, 2020, 10:27:59 PM by UndeniableUrges »

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