Final chapter of Jame's perverted conversion into a submissive, sissy- cuckold.
James' Descent into Cuckoldry 5 (MF, M+FF, Spanking, Anal, Cum Eating, Forced Feminization, Humiliation, Orgy)
Summary – Jamie falls completely down the rabbit hole.
Previous Story Summary – James and Karen find another friend.
Note – This is a work of fiction, make-believe and fantasy. It is not based on real people or actual events. You must be of legal age to read this adult story. It is OK to have fantasies but turning a fantasy into reality can destroy lives. Don't be a dick with other people's lives!
Jamie woke up to the sun shining through the window blinds. He was overly warm and found he had limited freedom to move his arms or legs. He tried to sit up and realized the reason for his discomfort. He was pinned between Karen and Sheila in the big bed. Sheila had her arm around Jamie protectively, and Jamie was cuddled up to his Mistress Karen. He wiggled and snaked his way out from under his strong lovers’ limbs, doing his best not to wake them. He went to the kitchen to get the coffee started.
Feeling cum leaking from his loosened ass, he quickly went to the toilet. He was still wearing his sexy, pink outfit. He relived the memories from last night as he relieved his bladder and wiped his boi-pussy.
Sheila certainly was a girl with something extra! And he had that extra bit up his ass and in his sucking mouth more than once yesterday. What a load she could shoot too! He licked his lips remembering how he had cleaned up his wife’s sperm-filled pussy.
Sheila soon joined him in the kitchen wearing his wife’s bath robe. She had found it hanging on the bathroom door.
“Good morning, sexy,” she said. Jamie quickly got up and poured her a cup of hot coffee. Shelia took it from him, set it down, and embraced Jamie, grabbing his ass and kissing him passionately. Sheila fingered his little dick and pinched his nipples playfully.
“You too at it again all ready this morning?” Karen asked. She had come into the kitchen just in time to watch her lovers making out. Jamie’s little sissy’s cock was hard and Sheila’s cock was slightly engorged, hanging low and thick.
Embarrassed, Jamie quickly fetched his Mistress her coffee. Karen was wearing a simple pajama top that barely covered her round ass and tasty cunt.
The three drank their coffee in near silence. Their conversation consisted of slurps, swallows, quick glances and shy smiles.
“Care for breakfast, Sheila?” Karen asked.
“Sure,” Sheila said, “What are we having?”
“We can do eggs and toast, or maybe pancakes and sausage?” Karen stated.
“Pancakes and sausage, please,” she said, and then added, “With a creamy, white sauce?” She looked at Karen and Jamie and they all giggled, remembering their joke from last evening.
“That’s exactly how Jamie likes his pancakes, isn’t it faggot?” Karen said sweetly.
Jamie nodded his head, ashamed.
“Would you like some too, Sheila?” Karen asked.
“Sure, if there’s enough for both of us,” Sheila said. “It sounds delightful, a little salt to go with the sweet.”
“Yes, exactly.” Jamie said.
“You heard the lady,” Karen said to Jamie, “Get busy!” She pointed to the stove.
“Yes Mistress,” Jamie said automatically. He jumped up and began to cook. Sheila shook her head in amazement and Karen smiled, proud of her public display of control over her submissive, sissy husband.
Jamie soon had breakfast ready and placed three hot plates of pancakes before them.
“Aren’t you forgetting something, Jamie?” Karen asked. “The lady asked for some creamy white sauce, so start jerking that pathetic little thing and give her what she asked for!”
“Yes Mistress,” Jamie said. He stood up and began to tug on his soft, little dick. He darted his eyes from his penis to his Mistress and Sheila, and then to the plates of pancakes before him. Karen began putting butter and syrup on hers and began eating.
“Hurry up faggot, before our guest’s breakfast gets cold,” she added sternly.
Sheila watched Jamie whacking his tiny, limp dick a while, thoroughly amused. She put butter on both of the remaining stacks and prepared them for Jamie’s sperm. “Maybe I can help,” she said, not wanting her food to get cold. She opened her robe to show off her breasts and thick cock, stood up and then knelt before Jamie. She began sucking on his puny dick.
“Tell her when you are about to cum, faggot,” Karen said, before biting into another forkful of pancakes.
Sheila sucked Jamie’s little pecker while he moaned and groaned in happiness. She slicked up a manicured finger and pressed it into Jamie’s ass. She prodded him, licked him and sucked him. She felt him getting agitated. He began to wiggle and squirm.
“Now!” Jamie said excitedly. Karen watched her husband pull his cock from Shelia’s mouth and jerk it over the food. “Ungh, ungh, eeeee-eee!” he squealed. He spurted three wads of fresh sperm, getting most of it on Sheila’s designated plate. He squeezed out the last few drops and wiped his oozing cock onto his pancake.
“Hmmmf!” Karen snorted, “That’s not much at all? Is that how you treat our guest, Jamie?”
“I’m sorry Mistress. I’m sorry Sheila,” Jamie said, his head hanging down. “I made cummies three times last night,” he said, trying to defend his small amount of ejaculate.
“Don’t be sad, Jamie,” Sheila said, “I’ll help you.” She stood up and pointed her nearly hard cock at Jamie. She waved it at him. He fell to the floor and began sucking. Sheila met Karen’s gaze and simply said, “I always get hard when I suck cock.” Karen simply sipped her coffee.
Jamie did his best to make Sheila cum. He sucked her cock, licked her fat, flared cock-head, tongued her foreskin, jacked her and deep-throated her long fat shaft over and over. Jamie played with Sheila’s big, heavy balls and then probed her ass with his fingers. The sounds of cock-slurping filled the small room. Jamie soon had Sheila ready to blow. He felt her cock swelling and getting even harder in his mouth. Regretfully, Sheila pulled her cock from him and began to jack off.
“Let me!” Jamie exclaimed and put his small hand on Sheila’s thick cock. He stroked her, amazed at the hardness and thickness of her throbbing member. He watched her vein filled skin slide over her purple colored glans. He felt her cock twitch violently in his hand, and a massive spurt of cum left her piss-hole and splattered across both plates. To Jamie’s delight, Sheila put her hand on his and aimed the rest of her thick ejaculate onto his plate. Blast after blast covered his breakfast with thick, white goo, painting his brown cake with warm, white cream. After the last spurt left her turgid cock, Jamie sucked it clean. Then, they sat down to enjoy their breakfast.
Karen, having finished eating, watched them eat their cummy meal. “What do you say, faggot?” she asked her husband.
“Thanks for all the cum, Sheila!” he said, “It’s delicious!” He placed a thickly covered piece in his mouth and chewed enthusiastically.
“You’re welcome Jamie,” she said, taking another bite. “It is pretty good.”
After breakfast, they said their good-byes to Sheila, promising to get together again soon. Jamie cleaned the kitchen and then attended to his wife as she showered. Karen left the house to spend her Saturday shopping and getting her nails done.
Jamie began his chores after first applying his special lotion to sooth his sore ass, cock and puffy nipples. He inserted the large butt-plug, put on a pair of fresh panties, and then naughtily decided to attach his nipple clamps. Even thought his nipples were swollen and tender, even more than before, he liked the gently tugging and pinching on them as he did his chores. He thought the constant pressure might be making his nipples longer and thicker. He stripped the bed, started a load of laundry and then started the dishwasher. After vacuuming the house, he decided he needed a break and lay on the couch to watch TV and play with his little dick.
Jamie was getting close to cumming in his panties when he heard a gentle “tap, tap, tap,” on the front door. He jumped up and peered through the window to see Sheila’s car in the driveway. He thought about getting dressed, but since she had already seen him naked and dressed like a slut, he answered the door wearing his panties, nipple clamps and butt-plug.
“Hello, Sheila,” he said happily.
“Hi, Jamie,” she said, “I left my shawl here last night. Have you seen it?” Sheila was dressed for a night out, even though it was barely past noon.
“No, but come in, I’m sure it’s here somewhere,” Jamie said. He opened the door and let Sheila in. He was slightly embarrassed by his attire, but felt emboldened by the hot sex they had last night.
“Wow, you are dressed for a party, Jamie,” Sheila said. She flicked the heavy steel ball dangling on the chain between Jamie’s nipple clamps. He winced just a bit and smiled.
“I like to wear them when I do my chores,” he explained. “I’m wearing a butt-plug too,” he added shyly. Sheila hugged him tight and ran her manicured fingers over his ass. She felt the plug in his ass and gave it a push and a tug. Jamie moaned.
“You naughty, naughty girl,” Sheila said. She gave Jamie a sensual kiss and groped him. She cupped his tiny cock and balls through his panties.
“Uh, I remember you taking off your shawl on the couch,” Jamie said. Feeling very horny but a little uncomfortable, he led her into the living room. Sheila followed him and they quickly found her black shawl nearly hidden behind a couch cushion.
Uninvited, Sheila sat down. Jamie sat down opposite her. “You were pretty hot last night, Jamie,” Sheila said. “You really like sucking cock and getting fucked in the ass, don’t you?”
“Yes,” Jamie admitted, “I didn’t think I’d like it at first, but Karen has taught me so much about myself. I really love sucking cock, getting fucked, and eating cum.” He flicked his nipple clamps and wiggled his stuffed ass against the couch. “You like it too, right?” Jamie asked, seeking reassurance.
“Oh, honey,” Sheila said, “The more cocks, the better! I’ve eaten more cum and fucked more cocks than I can remember. I started young, remember? I once sucked off eight guys at a poker game, and then they played ‘poke-her’ in my slutty ass for hours!”
“Wow,” Jamie said, feeling his tiny cock getting hard. He reached down and rubbed it, massaging his little cock-clitty.
Sheila watched Jamie playing with himself. She pulled up her dress and pulled down her panties. Her thick cock dangled from her purple panties. “Come over here and suck this for me, Jamie,” she said.
“Uh…,” Jamie said. He was not sure how his Mistress would feel about him sucking cock without her being present.
Knowing Jamie was a submissive bottom, Sheila waved her cock at him and told him very firmly, “I said get over here and suck my cock, Jamie.”
Jamie licked his lips.
“Don’t you want to wrap your lips around my fat, shemale cock, lover?”
“Uh huh,” James said, acknowledge his need.
“Then do it!” Sheila ordered, making it very clear it was not a request he could refuse.
Jamie jumped up and then got down between Sheila knees. He began to suck and lick on her thick shaft greedily. Sheila’s cock hardened in his mouth. He pulled it from his lips and admiring his handiwork and her gorgeous cock, licking it up and down and sucking on her heavy balls before slurping it back into his mouth. He bobbed his head on her fat knob and sucked her deep. The heavy ball on his nipple clamps swayed back and forth. The clamps tugged on his nipples, making them hard.
“Ahhh,” Sheila sighed, “You certainly know your way around a cock, faggot.” Jamie deep throated her shaft, trying to suck up the sperm from her heavy balls. He noticed she had called him ‘faggot,’ just like his Mistress did.
“Go get the lube, Jamie,” Sheila said, “I want to tap your fine ass again.”
Jamie looked up at Sheila, his lips still wrapped around her fat cock. He took his mouth away and said, “But…”
“Butt, ass, sissy-cunt, whatever you call it, I’m going to fuck it. Now, go get the lube, faggot, or I’ll fuck you without it!” Sheila looked angry, and she was much bigger than Jamie.
Jamie jumped up to get the lube. He quickly returned and tried to hand it to Sheila. “No, you do it,” she said, “I don’t want to get my hands dirty.”
Jamie lubed up Sheila’s hard, fat cock. He then dropped his panties and tugged on his butt-plug until it slipped out of his gaping fuck-hole. Looking around for a place to put the filthy device, he started to set it on the table but realized his Mistress would be upset with him. He stopped and turned, obviously distraught.
Shelia yelled, “Hurry up!” Startled, Jamie tossed his butt-plug on the couch, figuring he could clean up the leather before his wife got home. He plunged his slimy fingers into his ass-hole, getting it ready to be invaded by Sheila’s thick shaft.
To Jamie’s surprise, Sheila sat on the couch, her hard cock pointing at him, and she said, “Ride it, bitch,” Jamie whimpered and straddled Sheila’s long legs. Looking into her eyes, he raised himself above her cock and reached back to grip the shaft and guide it to his hole. Easily finding the entrance, he pushed himself down on it.
“Aaaaaahhhhhh!” he groaned as Sheila’ thick cock pushed into him. He spread his legs and pushed out his ass to ease the cock into him. Finally, he rested upon her lap, her cock fully inside of him. He placed his hands on Sheila’s shoulders and pulled himself up, then pushed himself back down. He began to fuck her gently.
“Oooohhhh, shit, that feels goooo-oooood!” Jamie hissed as the hard cock filled him up. He raised his ass up and down, fucking himself with long, full strokes.
Sheila grabbed him and kissed him forcefully, darting her tongue in and out of his mouth and smashing her lips against his. Jamie rode her fat dick, up and down. Sheila leaned back and watched Jamie; his face was filled with lust, pleasure and just a little pain. He bounced his ass on her thighs. Seeing the heavy ball his on nipple clamps bouncing, she grabbed it and slowly tugged it. Jamie’s nipples stretched and pulled.
“Aaaa-ahhh!” Jamie grunted as his nipples sent shock-waves through his body. He fucked himself faster and deeper. One clamp popped off with a ‘snap!’ and Jamie flinched, looked at his breast and saw how red and swollen his nipple was. Sheila continues to pull the chain and they watched his other nipple stretch even more, and more, until the clamp popped off. Sheila’s leaned in and sucked his sore tit.
“Mmmmmm-mmm!” Jamie groaned as Sheila devoured his breasts. He began to fuck her harder. Sheila started humping upwards, in time with his motions.
Sheila stood up, holding Jamie in her arms and fucked his small body with hard thrusts. She then tossed him on the couch. “Bend over!” she ordered.
Jamie bent over the couch and pushed his ass back towards her. Sheila shoved her fat cock all the way into him in one fast stroke. She then grabbed his small hips and began to pound his sissy-ass.
“Smack…, Smack…, Smack!” The sound of flesh hitting flesh echoed around the room each time Sheila’s hips slammed into his ass.
“Ohhh…., Ohhh…, Ohhh!” Jamie cried. Her cock pressed against his prostate, his balls tightened and sissy-clit began to spurt! “I’m cumming!” he cried as his dick flopped and bounced, sending his sperm flying in all directions. Sheila was pounding him too hard to let him use a hand to catch it. “Eeeeiii-iiii! Ungh! Ungh! Ungh!” he cried as his tingles washed over his tiny nut-sack. His orgasm was so intense, it made him wonder if he could ever cum again without feeling of a hard cock pounding his ass.
“Where do you want my cum, faggot?” Sheila asked as she continued to slam his cunt, “In your ass or on your faggot face?”
“In my mouth!” Jamie panted, weakened from his orgasm.
Sheila pulled her cock out of his ass and Jamie quickly turned around and dropped to his knees. He scooted up close to her and opened his mouth. Shelia stroked her massive shaft and Jamie waited impatiently.
“Ahhh, take it, fag!” she groaned. A massive blast of hot sperm flew from her cock and splattered Jamie’s face.
“No, I want it!” Jamie cried and placed his opened mouth over Sheila’s spurting dick. Another thick surge of cum erupted from her shaft and into his sucking mouth. “Mmmmm!” Jamie groaned, rolling the goo around on his tongue. Another spurt and then another filled his mouth and he was forced to swallow or choke on it. Jamie played with Sheila’s balls, hoping to coax up more cum. Three more heave spurts filled his mouth and he sucked her cock gently, relishing her thick, copious amounts of sperm as her balls pumped gobs and gobs of thick, warm, salty sperm into his mouth. Jamie enjoyed large load filling his mouth. He held it without swallowing, just to taste it a bit longer.
“Ahhh, thanks, faggot,” Sheila said. She wiped her cock on his cummy face and picked up his panties to clean herself. She tossed his soiled panties at Jamie and said, “Tell Karen I’m free this weekend.” She put on her panties, smoothed her dress, grabbed her shawl and left.
Jamie sat on his knees in a daze. His cock oozed sperm and he felt the cum dripping on his face. Moments passed. He sat still, stunned by how quickly everything had happened. His knees began to ache. His ass ached and felt empty. He heard the door open and close again, and assumed Sheila had forgotten something.
“Was that Sheila’s car just leaving,” Karen said loudly as she walked into the living room.
Jamie looked at her, still on his knees, his cock dripping onto the carpet. He tongue had been snaking out of his mouth to lick the dripping sperm on his lips, but he froze. He looked at his wife and saw her seething. He pulled his tongue back into his mouth.
“Jamie Fag-i-oli!” she screamed. “You have the nerve to cheat on me in my own house?”
“No! Mistress! It wasn’t like that!” he began shaking.
“How was it then?” Karen yelled, “You have her cum dripping off your face and your faggot clitty is dripping on my carpet!” She looked at the couch in horror. “You spermed on my new couch!” she cried. She saw his dirty butt-plug. “You left your filthy toy on it too!” Karen marched up to him angrily.
“She made me Mistress!” Jamie cried, “She just stopped by to get her shawl and she made me suck her cock!”
“She made you?” Karen yelled. “I doubt that! I bet you pulled her cock out of her panties and began sucking on it the minute she walked in the door, like the filthy, faggot slut you are!”
“No Mistress!” Jamie began to cry.
“What else did you do to her while your wife was out running your errands?” she yelled.
“She made me sit on her cock and ride it, and then she fucked me, really, really hard!” Jamie said sadly, looking for sympathy, but Karen wasn’t going to give him any.
“GO GET MY HAIR-BRUSH!” she screamed and pointed to the bedroom
“No Mistress!” Jamie looked terrified. He remembered the last time he had disobeyed her.
“Now faggot!”
Jamie whimpered and ran to fetch the hair-brush. He was going to get it. Why, oh why, did he ever disobey his Mistress?
He returned, sniffling and wracked with sobbing. He handed Karen the hair brush and dutifully lay across her lap to prepare for his punishment.
“I’m sorry Mistress,” he said, really meaning it. He waited for his spanking, naked on his Mistress’ lap. His oozing cock pressed against her.
“You have to be punished for cheating on me and messing up my nice, clean house,” she stated simply.
She raised the brush high in the air…
“Don’t you ever have sex behind my back again!”
“SMACK!”
“OWWW! No Mistress!”
“Don’t you ever sperm all over my furniture!”
“SMACK!!”
“OW-WOW! No Mistress!”
“Don’t you ever leave your filthy toys in my nice, clean, living room!”
“SMACK!!!”
“OWWZIE-WOWZIE! No Mistress!”
“YOU CHEATING,”
“SMACK!”
“COCK-SUCKING,”
“SMACK!”
“FILTHY LITTLE FAGGOT!”
“SMACK!”
“SMACK!”
“SMACK!”
The last swat caught Jamie’s nut-sack.
“OWWW, OWWW, OWWW!”
Karen pushed him off. He fell in a sobbing heap on the floor.
“Look what you did!” Karen yelled, “You got sperm on my leg! LICK IT OFF RIGHT NOW!”
Jamie sat up and crawled to his Mistress. He saw his slime on his Mistress’ leg where his pathetic cock had oozed on her. He lapped his sperm trail from her leg and thigh.
“Now the couch!” She yelled, pointed to his spermy residue splattered all over the couch. He climbed on the couch and licked it up too.
“I stepped in your cum!” she screamed. “Clean it up!” She put her heels in his face and he began to lick the soles of her feet.
“Now the tops!”
Jamie began to lick her shoes, groveling.
“Hand me your filthy butt-plug!”
Jamie gave it to her. She held it with two fingers and pointed it at him.
“OPEN!”
Jamie opened his mouth and Karen shoved the dirty butt-plug into his mouth.
“SUCK!”
Jamie sucked on the plug as his wife fucked his face with. He cleaned the butt-plug until it was shiny with his spit.
“BEND OVER!”
Jamie bent over and Karen forcibly shoved the butt-plug up his still lubricated ass.
“Now, clean this room! Wipe down my new couch and scrub the carpet!”
Jamie began to clean, sobbing and sniffling the whole time. He heard Karen stomping through the house and turning on the shower. He knew he better stay away from her for a while. After the room was spotless, he sat on the couch quietly. He heard her finish her shower and then heard the blow-dryer running as she did her hair. He waited patiently for her, wondering if she would punishment him some more. He planned to sleep on the couch tonight, to keep out of her sight until she calmed down.
Before long, he heard the ominous ‘click, click, click’ of her heels on the bathroom floor tiles. He heard the door slam and his wife stormed out of the bathroom. She was wearing her favorite party dress and her hair and make-up showed that she was ready for a night out.
“Where are you going?” Jamie asked, “Mistress?”
“OUT!”
“Can I come too?” he asked, already knowing her answer.
“NO!”
The door slammed behind her. He heard her tires squealing as she pulled out of the driveway.
He had really done it this time, he thought.
“Jamie,” Karen slurred, “Wake-y, wake-y, fag-y, fag-y!” She poked and prodded Jamie as he lay sleeping on the couch.
“Wha…?” Jamie said, waking from a sound sleep. “What time is it?” he asked groggily.
“Time to wake the fuck up, Jamie.” Karen said, giggling. She grabbed his hand and pulled him off the couch. “Come to bed, cocksucker,” she sang, “I have a surprise for you!”
Jamie followed his drunken wife into the bedroom. “Strip!” she ordered. Jamie dropped his panties.
“Get on the bed,” she said, “On your side of the bed, faggot!” Jamie always slept next to the wall. He lay down as he was ordered. Karen set her bag on the bed and then shimmied out of her dress. She wasn’t wearing a bra. She dropped her panties and they fell heavily on the floor. She crawled on the bed and immediately straddled her husband’s face.
“Eat me!” she said.
Jamie gave her cunt an enthusiastic slurp, wanting to please her, but suddenly stopped. Something was different... He sniffed her cunt as it lay heavily plastered on his face. Jamie smelled the unmistakable odor of male sperm! He rolled her thick juices on his tongue to confirm his suspicion. He tasted cum. Someone had fucked his wife and filled her pussy with sperm!
“Karen?” he said sternly, “Did you have sex with someone?” He pretended to be very angry. He was supposed to be angry, right? But, he had brought this on himself by cheating on her. The heady aroma of cum made his head swim. He wanted to shove his tongue into her slimy hole but somehow, surprisingly, he resisted.
“I told you I had a present for you, faggot!” she slurred. “And, you forgot to call me ‘Mistress.’” She slapped his cock and then sat drunkenly on his face. She loosened her cunt muscles and pushed. A large, thick gob of cum oozed out of her slimy pussy and landed on his lips. She slid her pussy back and forth on his mouth, smearing his face with cum and pussy juice.
“Mmmmmph!” he cried, trying to get away.
“Now, don’t fight Mistress,” Karen sang, “Or she’ll have to get the brush and paddle widdle Jamie’s faggy bum-bum!”
Jamie fell limp, not wanting another paddling.
“Now EAT ME!” Karen yelled and humped her husband’s face again.
Jamie whimpered and opened his mouth, once again defeated. He began to lick his Mistress’ pussy; tentatively at first, then he tongued her deep, feeling the slippery, slick discharges in her recently fucked cunt. Another gob of cum slipped into his opened mouth.
“Oh, yeah, that’s it!” she moaned. “Clean up all that nasty sperm from my poor, tired pussy! I had three of them tonight, faggot. Three loads of hot, creamy cum in my pussy for my faggot husband to slurp up. Unngghhh!” she groaned and said, “Aren’t I good to you, baby?”
Jamie licked her tender cunt, humiliated, but savoring the thick sperm and swallowing it down. Gravity forced more and more sperm from her cunt. She ground her slimy pussy on his face as she groaned. “All three hard, thick cocks fucked me Jamie. Bigger cocks than you ever could give me. I came all over their cocks like a wanton slut, faggot.” She slid her ass over Jamie’s face and he began probing at her bung-hole, as she liked. ”One of them fucked my ass too, so make sure to get it all out!” He immediately plunged his tongue into her ass and began to clean it too. He could taste her ass, sperm and the foul taste of the lubricant she had used. He slurped and sucked her pussy, trying to clean up the slick, gooey cum.
He heard her rummage in her bag as he worked on her cunt and ass. Karen began to play with his cock. She was very aggressive with his junk; squeezing him and flicking her fingernail on his nut-sack.
He moaned and licked her furiously; even though Karen was being so rough, she must have forgiven him! He slurped her tasty fuck-hole and ass as she played with his cock. He was hoping she would make him cum, but she was hurting him; he couldn’t get aroused. He soon felt something hard and cold encircling his balls, pinching them tight. What was this, some kind of new toy? Then, he felt his tiny cock squished and squeezed. Finally, he heard an ominous ‘click.’
“There, that should keep you from cheating on me again!” Karen declared triumphantly. She fell off of her husband and giggled uncontrollably. Jamie sat up and saw his cock encased in a tiny pink, male chastity cage! A small lock held it secure.
“Karen? Mistress?” he said worriedly, looking down at his caged cock.
“Don’t even think about trying to take it off. Your tiny nuts will probably tear off with it!” she laughed. “Besides, you don’t even need your cock any more. All it does is flop around when you get fucked anyway! I had to go to three porn shops until I found one small enough!” She laughed.
“I know I deserve it - for cheating on you - but…, but…, you’ll take it off when we have sex, right?” he asked. “Mistress?”
She howled with laughter. “Sex…? With you…? And that that pathetic little thing you call a dick…? HAHAHAHAHAHA!” She pointed at his locked-up cock. “It was already useless to me Jamie, and with all the real cocks I’ve had lately, I don’t even want to see your cheating, limp, faggot, pinkie-dick again! Let alone have sex with it!” She laughed at him cruelly, the alcohol buzz fueling her anger. “You silly, pathetic excuse for a man!” she screamed.
He looked at her and then at his caged cock and began to sob. What had he become? He had turned into a cum-eating, submissive sissy-faggot whose only thoughts are about pleasing his Mistress, eating her spermy cunt and sucking and fucking hard, throbbing cocks!
“Now, go get back on the couch. I’m going to bed!” She noticed her panties on the floor. She picked them up as Jamie was about to walk out.
“Hey, faggot!” she said loudly.
“What?” Jamie replied, turning to face his strong willed wife.
“Here, for a midnight snack later!” she tossed her cum-soaked panties at him. He caught them, felt their weight and immediately brought them to his nose to sniff their aroma. He glanced at Karen and saw she was watching him. He turned around and left, humiliated once again, carrying the heavy panties in his hand. He heard Karen giggling as he shut the door.
Jamie lay on the couch, softly sobbing. He thought about leaving her but realized he was nothing without her. He sucked on her wet panties and fell asleep with the sperm soaked garment on his face. His cage kept his small cock from getting hard.
The next morning, Karen slept late and Jamie had time to inspect his new chastity cage. He was locked up tight and Karen was correct as always; he would probably hurt his balls real bad if he tried to take it off. His poor baby-balls were encircled by a small ring and his small cock was stuffed inside short a plastic tube with a wide slit in the front for his urine to escape. A small, brass padlock held everything secure. He had become aroused last night while he slept; dreaming of fat, thick cocks, but his own tiny clit began to hurt and couldn’t get hard. The hard plastic pulled on his balls and his tiny dick was squeezed tightly by the cage.
Karen finally awoke and Jamie served her coffee. She smiled at the hard lump in his panties. “Nice man-bulge,” she said giggling. He noticed she was wearing a thin necklace with a small key hanging from it. “Let me see it!” she ordered.
Jamie pulled down his panties and showed his Mistress his cage.
“It looks darling on you Jamie!” she snickered. “It even makes your tiny, faggot dick look bigger!”
“Are you really going to make me wear this, Karen?” He asked his wife. She glared at him menacingly. “I mean, Mistress.” He looked down at the floor.
“Since you’ve shown me you can’t be trusted, yes, absolutely,” she said. “First, you cheated on me with that sissy-bitch Sheila, next thing you know, you will be going down to Rapunzel’s and sucking and fucking strange cock in the alley!”
“I wouldn’t!” he cried in horror.
“I know,” she said, “Not yet anyway.” She finished her coffee while he cooked her breakfast.
He served her and sat down at the table, his head down and glancing at her furtively.
“Things are going to be different around here, Jamie,” she said. “Since you cheated on me, I have the right to cheat on you. It’s only fair, after all.”
“I guess..,” Jamie agreed.
“So, this is how it is going to be; you can stay married to me and continue to live here as long as you do everything I say – and I do mean everything! Cooking, cleaning, the laundry, whatever I demand.”
Jamie already did those things. “Yes, Mistress,” he said.
“And, since I know what a real cock is like now, I will continue to fuck anyone I damn well please! If you don’t like it, you can get the fuck out of my house!”
“No Mistress!” Jamie said, panicked at the thought of being out on the street. “I want to stay!” he whined.
“Good,” she said, smiling behind her coffee cup.
“And, if you behave, and be a good little faggot, I’ll give you lots of warm, creamy cum to lick out of my cunt.”
“Yes Mistress,” Jamie said, encouraged.
“Maybe I’ll even bring home a few fat cocks for you to suck and fuck - as long as I’m finished with them, that is,” she smirked.
“Thank you, Mistress,” Jamie said cheerfully, looking up at his wife. Maybe it wouldn’t be so bad after all!
“However, if you don’t behave and fail to follow any of my orders, I’ll paddle your little faggot ass until it is redder than my sluttiest lipstick, and then throw you out on the street!”
“Yes Mistress,” he said, “But, Karen…, Mistress? Can we still have sex sometimes? Once in a while, maybe, if I’m good?” he said sadly, looking at her hopefully.
“Don’t be silly, of course not!” she said. “I couldn’t even feel your little cock before, let alone now. Besides, you know you love cocks and cum more pussy anyway,” she said, “I’m sure you will be able to cum once in a while when some big-dicked stud if fucking your faggot ass. So, what is it going to be faggot? Stay here and be my cuckold, faggot slave, or get the fuck out?”
“I’ll stay, Mistress,” he said sadly, afraid to leave her, but excited by the promise of getting her sloppy leftovers. He knew he could never please her with his cock any longer. It was a small price to pay.
“Good!” Karen said, “Now, get out of my sight until I call you again.”
“Yes, Mistress.”
From that point on, Jamie was banished to sleeping on the couch until his Mistress turned his den into a pretty, pink bedroom. He was glad to have a proper bed again and thanked his Mistress profusely. She claimed she only did it to save her couch from getting ruined.
He spent his weekends waiting for his wife to come home to give him a special treat. He would eat her cummy-cunt until all the sperm was cleaned from it. Occasionally, Sheila would visit and she would let him suck Sheila’s cock until it was ready to fuck her. He once sucked her so good he received a surprise mouthful of warm, thick cum. His paddling was worth it, he decided.
As time passed, Jamie’s nipples became even more tender and puffy; even the flesh behind his areolas began to swell. He finally got up the nerve to ask his wife about them once again.
“Did you talk to the doctor about my ‘problem’ yet Mistress?” he asked, touching his breasts.
“Oh, I had to cancel my appointment, and now I can’t get in for another three weeks!” she said. He looked forlorn. “Oh, I’m sorry,” she said, “Here, I’ll make it up to you!” She pulled the chastity cage key from around her neck. “Care for a wank, faggot?” she teased. Karen usually only let him out of his cage on Sunday, to wash his faggot-parts and let him make cummies on his pancakes. Jamie thanked her.
Weeks went by and Jamie again asked her about his tender breasts. “Mistress, I think there is something wrong with me. My hair and skin have been feeling so soft, don’t have to shave nearly as often as I used too.” he said, “And I’ve been so emotional lately!
“I think my cock balls are getting smaller too…” he added softly.
“How can you tell,” she teased. Seeing the hurt look on his face, she relented, “Ok, I have an appointment with the doctor this Friday and I’ll ask her about your silly nipples, satisfied?”
“Yes Mistress, thank you!” he said. “Oh, and Mistress Sheila wanted to know if she could have a key to my cage too?”
“Did you put her up to this, faggot?” Karen asked sternly.
“No Mistress, you can ask her!” Jamie’s eyes grew wide with fear.
“I will.” Karen said simply.
Friday night after work Karen came home and Jamie met her at the door.
“What did the doctor say, Mistress?” He was really worried about his breasts and genitals.
“Uh, well,” she began, “I don’t know how to tell you this, you better sit down.” Jamie sat down and looked at her, fearing the worse – cancer or some other horrible disease!
“Here goes!” Karen said, and took a deep breath. “The lotion you have been using was a pre***********ion for me. I didn’t know it,” she lied, “but, you have been using female hormones for months now.”
“What?” Jamie said, “Female hormones?”
“That’s why your nipples are swollen – you are growing breasts.”
“Oh no! I’ll have to stop using it then!” Jamie grabbed his slightly pronounced, developing titties. “When will they get back to normal?” he said, his voice rising in alarm.
“Uh, sorry, Jamie - it’s too late. The doctor said it is irreversible. She gave me these pills for you to take; testosterone blockers; though I can’t believe you are making any at all with those little marbles. She also gave me a supply of medicine and needles for your hormone injections. They also have a patch, suppositories or a lozenge, but I feel the shots are better for you. Your mom had big tits, you should be able to grow a nice fat pair too!”
“WHAT?” he said. “I’M GOING TO GROW TITS?” he looked down at his chest, imagining a huge set of cock-magnets protruding from under his shirt.
“Look, I know it is a big change for you, but honestly, you know you are a better woman than you ever could a man,” she said, trying to cheer him up. “Besides, you like being a girl. You like to do girly things like cleaning and shopping and getting all pretty and sucking and fucking cocks! Now, you will have breasts to go along with it. Guys love tits, and you won’t have to use those fake breasts anymore. It will be fun!”
“But, but, but…,” Jamie was torn. He was excited by the thought of having a real set of breasts to play with, but nearly devastated to see the last shreds of his masculinity leaving him.
“What will the guys at work say?” he said, thinking of walking into his office with a pair of breasts under his jacket. The tape they were using now was barely enough to hide the growing buds on his chest. He looked down at his protruding nipples and swollen breasts and wondered how big they would get. The guys at work were already teasing him about his long hair and his girlish looks. He would be teased even worse than when he was in high school!
“I thought about it on the way home. You can quit work if you want, since I make enough for both of us.”
“But, what will I do for money?” he whined, playing with his nipples.
“What do you need money for, Jamie?” Karen said, “You don’t have any friends and you never go out. If you want some nice things to wear, I can give you an allowance, or maybe you can work from home! I hear there is a lot of money in porn? Maybe you and Sheila could do sissy-shemale web cams?
“And, you like to suck cock. There is money in that too. That way, whenever you want something nice, like new, pretty clothes, panties, bra, or a new dildo, I can pimp you out! Guys are always willing to pay to get their cock sucked! You will be doing what you love and get paid for it too!” Of course Karen would have to control his money. She didn’t want her well-trained sissy cuckold having any thoughts of running away.
Jamie’s head was swimming. It was all too much for him. But, his Mistress was strong and smart enough for the both of them. He sighed.
“OK, Mistress,” he said, accepting his fate, knowing he was just beginning a new journey in life. He was a little scared, but maybe this was the path he should have followed a long, long time ago.
“Good boy! I mean good girl! Come on, let’s go out to celebrate!” Karen said cheerfully, “Go get made-up and put on your pretty clothes. I’ll take you out and maybe we can go shopping? I know! We can get our hair and nails done together! Won’t it be fun? My treat!”
“Yeah, sure!” Jamie said cheerfully. It did sound like fun! He was excited!
The girls had a nice time. It was the first time Jamie ventured out in public dressed like a woman. His Mistress bought him some sexy clothes and they both got their hair and nails done. Karen even bought Jamie some new make-up at the mall and he received professional tips from the make-up artist. He looked very hot and sexy, though his feet were getting a little tired from his high-heels. And, he noticed the long glances he received from a so many of men and realized he had never had looks like that from women! Being a girl might not be so bad after all!
Karen took Jamie out dancing that night and showed him how to spot the men with the biggest cocks. Jamie soon got the hang of it, and the two compared their observations with each other, giggling and getting tipsy. They danced together and enjoyed the stares from more than a few men. After a bit, Jamie got up to use the restroom. He quickly found it down a short, dimly lit hallway. He opened the bathroom door and noticed a man at the urinal looking at him in surprise. The man half-way turned around and Jamie noticed his thick cock and strong urine stream.
Jamie reached down for his zipper as he walked to the urinal and fumbled around a bit when he felt soft material of his dress instead of the expected cold metal zipper of his man-pants! Only then he remembered he was wearing a dress and make-up.
“Uh, sorry!” he said, “Wrong room!” He left very embarrassed and quickly went into the ladies room to relieve himself, locking the stall door firmly.
He told Karen about his mistake when he returned to their table. “Oh, that is so precious, Jamie!” Karen laughed. The two giggled about his public embarrassment for a bit and were discussing the man’s cock size when the barmaid brought them over two more glasses of wine.
“We didn’t order this,” Karen said to her firmly, not intending to pay for the drinks.
“Compliments of the gentleman at the bar,” the barmaid told them, indicating a good looking young man at the bar. The man quickly smiled at them, accepting their unspoken gratitude.
“That’s him!” Jamie said. To his embarrassment, Karen waved the man over immediately.
“Thank you for the drinks,” Karen said. “I’m Karen, this is Jamie.”
“Hello Karen, hello Jamie,” he said, and sat down at the table between them. “My name’s Ken.”
Karen laughed out loud. “I’m not laughing at you, Ken,” she said. “It is such a funny coincidence, Jamie use to have a boyfriend named Ken!” Karen and Jamie remembered Karen’s alter ego ‘Ken’ and his big rubber cock.
“I hear you already met Jamie in the men’s room,” Karen said, giggling, “She was just telling me about her little mistake and how she liked your cock.” She added, in a sultry, soft voice; “She said you had a nice fat one!”
“Karen!” Jamie replied, mortified.
“Oh, she liked my cock, you say?” Ken said, thinking tonight was his lucky night.
“Oh, she loved it!” Karen said, “Didn’t you Jamie?” She took a big gulp of her wine. Jamie followed her lead and took a big gulp. His face was warn.
“Er, um, it was nice,” Jamie said, turning red and nearly draining his glass. “Can we, uh, change the subject, please?”
“But you like talking about cocks, Jamie!” Karen said. She turned to Ken and added, “She is such a slut! All she ever thinks about is cocks, cocks, cocks!”
“Karen!” Jamie said.
“A toast, to cocks!” Ken said, hoping to get the ladies drunk. He held out his glass and Jamie and Karen toasted with him, Jamie with an empty glass. The gentleman noticed his empty glass and called the barmaid over for another round of drinks.
Jamie was getting drunk.
Karen made another toast. “Here’s to fat cocks, skinny cocks, and long, hard cocks in my tight little twat!” Karen said, “To cocks!” She drained her glass.
“To cocks!” Jamie giggled and took another long, deep swallow.
“Jamie really feels bad about embarrassing you,” Karen said, taking Ken’s hand and pressing it into Jamie’s. “In fact, she wants to thank you personally for buying us drinks, and to apologize for barging in on you a while ago.”
“What does she have in mind?” Ken said, raising his eyebrows and speaking to Karen, the obvious leader of the two.
Karen turned to her husband. “Jamie, why don’t you take Ken out back and suck his cock? There is a nice dark alley back there.”
Jamie’s eyes grew in surprise. He knew he had to obey his Mistress, or else she would punish him. His tiny cock lurched in its cage. He drained his glass.
“What about my friends?” Ken said, pointing to the bar where a group of men were hanging out, watching his conversation with the two pretty girls.
Karen whispered in his ear a bit and ran her fingers up his arm and to his shoulders. She then said loudly, “Bring them if they are interested!”
Karen led Jamie out the back door and into the alley. “But Mistress!” Jamie said, pleading with her. He felt apprehensive and degraded; being forced to suck a strange man’s cock in an alley!
“Shut up faggot,” Karen told him. “Get on your knees next to this dumpster.” Karen directed him to a place where his actions could be at least partially concealed from casual observation. Jamie started to comply. “Don’t ruin your clothes, I just bought them!” Karen said sternly. Jamie quickly found a piece of nearly-clean cardboard and kneeled upon it. Ken and his friends soon stumbled out of the backdoor, raucous and loud, into the dirty, dimly lit alley.
“Jamie is waiting over there for you, Ken,” Karen said, pointed to her submissive sissy-slut. “Now, thank the nice man properly, Jamie,” she directed.
Ken and his friends walked over to Jamie. Ken positioned himself in front of Jamie and looked down at what he assumed was a slutty, cock-sucking female. Seeing Ken hesitate, Jamie reached up and fumbled for his zipper. Ken quickly helped and loosened his belt. His pants fell to the ground. Jamie reached up and pulled down Ken’s underwear. He was rewarded with a close-up view of Ken’s half-hard cock. Jamie began to stroke it and then engulfed it with his mouth.
“Oh, you fucking slut!” Ken groaned. His friends chuckled. Ken felt the blood being pulled into his shaft and, after Jamie sucked his entire cock into his mouth and tickled him with his tongue, Ken quickly hardened. He thrust his cock deeper into the slut’s mouth, not caring about whether she wanted him to or not. She was nothing but cock-whore after all.
Jamie began to suck him in earnest, bobbing his head and licking Ken’s thick, spongy, cock-head. “Mmmmmm,” Jamie groaned, drunk and horny and tasting pre-cum. He sucked and bobbed and licked. He reached up and tickled Ken’s heavy ball-sack with his manicured nails and began to deep-throat him.
The other men gathered around the two of them, their cocks hardening, making lewd comments. The sounds of Jamie’s wet, sucking mouth and the heavy breathing of the five horny males echoed in the dark alleyway.
“Slurp, slurp, slurp, slurp, slurp, slurp, slurp, slurp.” Jamie’s head rhythmically bounced up and down on the fat, throbbing cock. He grabbed the cock with one hand and stroked it in time to his sucking. He wrapped his hand around it, twisting and stroking the fat shaft. His clitty tried to get hard in his cage. His panties grew damp with the pre-cum oozing from his piss-slit.
“Slurp, slurp, slurp, slurp, slurp, slurp, slurp, slurp.” Jamie continued, pleasuring the penis in his warm, wet, mouth, encouraged by Ken’s sighs of enjoyment.
“Oh, you slut, you fucking slut!” Ken groaned and started to fuck Jamie’s face. His balls tightened and he blasted his thick cum into Jamie’s mouth. “Ungh!” he grunted, unloading his pent-up baby-juice. Spurt after spurt erupted into Jamie’s other pussy-hole and he swallowed it down greedily.
Jamie guzzled the entire heavy load, and with a satisfied smack of his lips, inspected the cock for more cum. He squeezed out the last drop, licked it, and then looked around. The other men either had their cocks out stroking them and rubbing their hard shafts, silhouetted in the dim light street lights.
“Fucking slut knows how to suck a dick!” Ken said to his friends as he pulled up his pants. Jamie smiled at the raunchy but sincere compliment.
“Don’t be shy boys!” Karen said loudly, “Who’s next?” A large, burly man stepped forward and waved his cock in front of Jamie’s face. Jamie grabbed it and quickly wrapped his lips around it. He slobbered all over the thick, meaty flesh and began to repeat his performance - sucking and stroking the man’s hard cock and fondling his heavy, cum filled balls.
“Aw shit,” his Mistress Karen groaned, “This is so fucking hot!” She lifted up her skirt and rubbed her pussy as she watched. Then, she dropped her panties and the damp cloth fell around her ankles. Some of the men turned to her voice and saw her dark panties lying in a heap at her feet in the dim light, almost like a shadow had fallen over her feet. She kicked them off with a smooth flick of a high heel, took a wide stance and flipped up her skirt, showing her round, full, naked ass. She braced herself by placing her hands against the cold brick wall.
“I need somebody to fuck me!” she said loudly, “You!” she pointed to a man with huge, hard member, “Come here and fuck my little cunt with your big, fat cock!”
Karen shook her pale ass impatiently and the man quickly got behind her. He could smell her hot scent wafting up from her dark crack. He dropped his pant and squatted low to line up his cock. He grabbed his hard dick and slid his fat cock-head up and down her slit, getting it slick with her juices. He paused a moment to gaze into Karen’s eyes as she turned back to look at him. He plunged his thick cock deep into her with a single thrust of his hips. He smiled as her eyes widened and her mouth opened involuntarily as she gasped in surprise and pleasure.
“Ah, yes!” Karen moaned, feeling her cunt stuffed with hard cock. Her pussy-lips were spread wide and her hard clit became exposed. “Unngh! That’s what I needed! Now fuck me! FUCK ME!” The man began to plow his cock into her tight hole. “Mmmphh, mmmphh, mmmphh!” she grunted as the man fucked her hard, disregarding all niceties. She relaxed her body and began to rock back and forth to his thrusts. Karen began to hum to herself as she was being fucked, “mmmmm, mmmm, mmmmmm!” she hummed, and then ground her wiggling ass against him, pushing his cock in deep and spreading her hole wider. “So fucking good!” she exclaimed, nearly drooling from her excitement.
Another man grew impatient and pulled on Jamie’s arm. He placed Jamie’s hand on his hard shaft and made Jamie stroke his cock while he waited for his turn in Jamie’s mouth. Soon, Jamie was stroking two cocks while still sucking on the third. He felt the cock in his mouth stiffen and it began to spew its thick, bountiful load. “Mmmmph!” Jamie exclaimed in pleasure. However, not being able to keep the cock pulled tight to his face with his hands, the fat shaft slipped out of his mouth as he was pulled about by the other two men’s humping motions. Fresh sperm dripped out of his mouth and plopped onto his dress. With cry of alarm, Jamie opened his mouth wide and tried to capture it again, bending forward and to the left, then the right. With the still spurting cock free, Jamie took a huge blast onto his check, eyes and lips before he could corral the spewing flesh back into his sucking, swallowing orifice.
Jamie finished pleasuring the man and the cock was pulled from his lips. He looked up at the man, hoping to receive a small grunt of satisfaction in recognition of his efforts, but the man had already turned his back on him. Both cocks were pulled from his hands as the men jostled for position in front of him. With a quick push, the larger man won and he slapped Jamie with his hard cock. Jamie began sucking on it enthusiastically, rewarding the victor. The other man noticed that Karen’s pussy was free and scurried over to fuck it.
Karen had already cum all over her first cock and was about to cum on it again when she felt hot sperm blasting her pussy walls. The man pulled her tight, grunted a few times and filled her up with cum. When spent, the man pulled his cock from her unceremoniously. Her gaping hole clenched a few times, dripping fresh cum onto the ally. The loser of Jamie’s cock-sucking mouth grabbed her hips to hold her in place, and then shoved his hard cock into her used, slimy hole. “Just what I needed,” Karen said. She came one more time and received another huge deposit of hot sperm into her loosened pussy.
By that time, Ken had recovered and took his turn with Karen. He fucked her long and hard. She came again with cum oozing out of her spasming pussy.
More men stumbled out of the backdoor of the bar after hearing the stories of the ‘two sluts in the alley.’ Karen firmly informed the men that she was finished for the night, having already had three hard cocks banging her pussy. Her cunt was sore and tender. She instructed the men to get in a line in front of Jamie and she directed the action from the head of the line.
Jamie was focused only on the cock in his mouth or the ones in his hands. A few spurted on his face and hair as he stroked them off. He sucked and swallowed load after load until his belly was full and his hands were empty. Finally, the last cock left his slurping mouth. He watched the man put away, his cock still oozing, and zip-up. The man walked away, leaving Jamie alone, covered in cum, and beginning to shiver from the cold. The warm sperm on his face began to cool and he wiped it up and licked his fingers. He got up on his feet on his shaky knees and noticed his Mistress stuffing a huge wad of bills into her cleavage. “A few more hand-jobs and blowjobs and you might have paid for your clothes and dinner too,” she said to him shortly, noticing his stare. “You can pay me the rest later, faggot.”
She made Jamie walk back through the bar, his face, hair and dress covered with cum. The bar erupted, cheering the two sluts and giving them a standing ovation. Karen knew she would never have to buy a drink in that bar again.
Jamie cleaned his wife’s tired cunt with his tongue that night and thanked her for a fun night out. Karen took pity on her faggot and let him out of his cage for the night. Jamie stroked his tiny cock three times that night and again in the early morning, reliving his special night out and slurping up his cum in the quiet confines of his pretty, pink bedroom.
A few months later.
“Jamie!” Karen yelled from the bedroom.
“Yes, Mistress?” Jamie said, dropping his feather duster and running into the room.
“Jamie,” she said. “I invited my girlfriends over this afternoon. Make sure the house is spotless and make us some hors d’oeuvres, you know the ones I like. Oh, and I think we will have mimosas too.”
“Yes, Mistress,” Jamie said. “But I’ll need to run to the store, Mistress.”
“All right, make yourself pretty and hurry back. You can use some money from your piggy-bank. I’ll pay you back later,” she lied. “And don’t you dare give any free blowjobs to those stock-boys again. Twenty bucks each, understand?”
“Yes, Mistress.” He had been paddled harshly over that mistake! But, they are such nice boys and very appreciative.
“And Jamie,” Karen smiled, “I bought you a new outfit, make sure you are wearing it and get very pretty for us; more classy, less slutty this time, I want to show you off.”
“Yes, Mistress.”
Jamie freshened up his make-up and put on his favorite skirt and top. A final look in the mirror, and he was ready. He drove to the store in Karen’s convertible, his shoulder length hair blowing in the breeze. He felt so pretty and sexy! Jumping out of the car, he smiled up at the sunshine. It was such a beautiful day! He skipped into the store entrance. His C-cup breasts jiggled under his thin blouse and he could feel the breeze on his panty covered bubble-butt. Grabbing a grocery cart, he checked his list of items and began placing them into his cart. Turning down the next isle, he saw Tony, one of his favorite stock-boys! He demurely said ‘hello,’ and began to push his cart past Tony, who was stocking shelves.
“Hi! Miss Jamie,” he said, and stopped him from squeezing past the small pallet of cereal boxes he was unloading. “What’s your hurry, doll?” he said, blocking her path with a strong arm placed in front of him.
“Ah, no hurry, I guess,” he said. “I’m just shopping for Mistress Karen.”
“I see,” Tony said. “You really look hot today, Jamie. Do you have time for quick blow-job in the stockroom again?” he smiled.
“Uh, I don’t know…,” Jamie said, “Mistress Karen was really mad at me last time. You know I’m supposed to get at least $20 from everyone…”
“Oh, that won’t be a problem at all!” Tony said, “Follow me!”
Jamie obediently followed Tony to the rear of the store. ‘He said he’d pay me last time!’ Jamie thought.
They went through the big double doors and turned into the break-room. Before going in, Tony spoke into the store’s announcement system and, “Attention; all available Stock Clerks to the Loading Area. Code-Blue!” He repeated, ““Attention; all available Stock Clerks to the Loading Area. Code-Blow!”
Tony pulled Jamie into the stock room. He quickly dropped his pants, leaned against a desk, and motioned Jamie over. Jamie quickly fell to his knees in front of him and began to pleasure his cock. He had no sooner had Tony rigid in his mouth when the door banged open.
“Tony, you better not be playing another joke..,” the boy stopped. Walking into the room, he saw Tony leaning against the desk an when he looked on the other side of the desk, he found Jamie diligently sucking his cock. “Hey! Alright! Jamie is here Johnny!” He stood next to Jamie and dropped his pants too, wanting to be next in line.
“Time for our break, Greg!” Johnny said, pushing his way into the action.
“Hurry up, Jamie, we only have fifteen minutes!” Tony encouraged.
Jamie looked at the three cocks waving in his face. It was so nice to feel wanted. “Remember guys, I have to get twenty dollars each, or Mistress will punish me!”
“That’s not a problem, right guys?” Tony asked, grinning at his friends as Jamie went back to work on his cock.
“Nope,” Greg said.
“Sure, twenty dollars, just like last time!” added Johnny.
Jamie wanted to remind them that he didn’t get paid last time, Tony had both his hands on the back of his head, face-fucking his throat. With his hands free, Jamie played with the other two boy’s cocks and, getting them hard. He only had fifteen minutes after all!
Tony soon gave him a mouthful of cum and then Jamie turned his attention to Greg, who reminded everyone he was next even before Tony finished ejaculating into Jamie’s mouth. Soon, Greg shot his load, then Johnny soon afterwards.
Tony had just maneuvered in front of Jamie for a second blowjob when the store manager burst into the room!
“I’m not paying you punks to molest my customers! Now, get back to work!” Mr. Rossi said.
The boys scrambled to pull up their pants and ran out the room.
“You alright, Miss Jamie?” Mr. Rossi asked, making no effort to help Jamie up off of the floor.
“I’m great!” Jamie said, licking his lips and using a finger push a wad of cum from the corner of his lip back into his mouth. “They are such nice boys, except they didn’t pay me the twenty dollars they were supposed to…, each. Mistress Karen will be so mad at me!”
“I told you last time, get the money first!” He shook his head. Jamie was as stupid as she was pretty, with no sense of business. “I’ll comp your groceries again, same deal as before, OK?”
“OK.” Jamie reached for Mr. Rossi’s cock as he was pulling it out of his pants. Jamie started sucking on his cock and tickling his balls. When Mr. Rossi was hard, Jamie lifted up his skirt, dropped his panties, and bent over the desk. Mr. Rossi used the small bottle of lube had grabbed after hearing the store announcement, and quickly lubed up his cock. He plunged it into Jamie’s boy-pussy and began fucking him furiously. He soon deposited a huge, wet load into Jamie’s ass.
“Thanks Mr. Rossi!” Jamie said happily, pulling up his panties and straitening his skirt. He took the hastily written note for store credit Mr. Rossi gave him, and returned to finish his shopping.
On his way to the checkout line, Tony came up to him. “Uh, sorry about running out on you like that, Miss Jamie. Mr. Rossi really let us have it this time. We, uh, took up a collection for you. Here.” He handed Jamie some wrinkled bills and some coins. “Twelve dollars and seventeen cents,” he said. “It’s all we had. Mr. Rossi said he would hold back some of our wages for the next time.”
“Thank you Tony!” Jamie said, and gave him a kiss on the lips before Tony could react.
Jamie was so happy! With the free groceries and the money from the stock-boys, he could pay Mistress Karen the full amount for the blow-jobs and have a little left over to put back into his piggy back. Also, he had sneaked a large bottle of lube into his shipping cart – Bonus!
Soon, Jamie had all the food and drinks ready for Mistress’s friends. He took a long, luxurious bath, shaving his legs, arm-pits and genitals. After applying a liberal amount of perfumed lotion to his entire body, he fixed his hair and put on his make-up, making sure he didn’t look too slutty today, as his Mistress ordered.
He walked into his room and opened the box of clothes mistress had given him. Jamie squealed with happiness when he took off the lid. The box contained a pretty maid’s outfit! There were black fishnet stockings and garter belts, black panties, black high-heeled shoes and a new black chastity cage! The outfit was very sexy and designed to show off his curves; a black and white short dress with white ruffled trim. A white apron, black and white ruffled headband, and a plain, black, leather dog collar. Hanging from the collar was a simple silver dog tag. At first, Jamie thought it was shaped like an elongated heart, but looking closer, he discovered the truth. It was a cock. A downward pointing cock, with large set of balls on top. It was engraved with a single word in large letters: ‘SISSY.’ On the back: ‘This Faggot is the Property of Mistress Karen.’
“Do you like it Faggot?” Karen’s voice came from behind him.
“Oh, yes, Mistress, it is so pretty!” Jamie said. “Thank you Mistress.”
“Put it on, let’s see how you look,” she ordered. “My friends will be here any moment.”
“Yes, Mistress,” Jamie said.
“First, your cage,” Karen said. She squatted down and unlocked his pink chastity cage and pulled it off, making a short sound of disgust at the mere sight of his diminutive genitals.
As she began to replace it with the black one, Jamie, felt the fresh air on his dicklet and his boi-clit began to expand. Karen gave it a quick, hard flick with her fingernail. “We can’t have your little clitty getting hard now, pet. I had to buy you some smaller sized cages too. With all the female hormones you are taking, you hardly have any boy-bits left at all!” She giggled as she locked the small cage securely and then fastened his collar, locking it in place as well. “I bought you one in pink too, faggot. Black for formal, pink for everyday wear.”
“Thank you, Mistress.”
He was soon dressed and waited for Karen’s inspection.
Karen had him turn around. “Hmmm, let’s tighten the corset a bit more. Actually, a lot more,” Karen said. She began to pull hard on the laced corset on the front of the dress. Jamie caught his breath. “Let the air out! Not in faggot!”
Jamie exhaled, slowly and for a long, long, time. Karen pulled the strings tight, one after the other, then tied it in place.
“Much better!” she said. “We will have to buy you a proper corset soon. One we can really tighten up!”
Jamie thought this one was plenty tight; he was already having trouble breathing!
“Faggot, wait in the kitchen until I call you. Then bring the snacks and more drinks.”
“Yes, Mistress.” Jamie walked hesitantly to the kitchen, these heels were much higher than the ones he was used to.
“Oh, Jamie!” Karen called. “Bring out some refreshments for our guests! And more drinks!”
Jamie walked into the living room carrying a large tray of drinks and snacks. Four professional looking women were seated in various places around the room drinking mimosas. The tray he had prepared earlier was covered with discarded glasses. He efficiently served each of them, one at a time, bending over and showing off his cleavage and bare shoulders to those in front of him, and his panty covered ass and stockings to the ones behind him. His face had blushed immediately when he recognized them; Stephanie, Tracy, Tammy and Darla; all close friends of Karen. Of course he had met them all before; at parties, weddings and other social events. He was friends with their husbands and even played cards with some of them (until Karen made him stop).
“I didn’t know you had a maid,” Stephanie exclaimed. “She’s so darling!”
“Oh, yes!” Tracy said. “I want one just like her!”
“Me too!” said Tammy. “And how sexy she it! How do you make her dress like that?”
“Where ever did you find her?” asked Darla. “I must know!”
Karen basked in their jealousy for a long while. “Jamie is very special, she’s one of a kind,” Karen said. “Isn’t that so, Jamie?
“Yes Mistress.”
“You are dismissed,” Karen said.
“Yes Mistress” Jamie performed a curtsey, and left.
“Oh how absolutely adorable!” Tracy exclaimed.
“So, what does she do for you, besides serve your slutty friends drinks?” Darla said.
Karen began, “She cooks, cleans, runs errands for me - anything I ask of her.”
“No!” Tammy exclaimed. “That must be very expensive!”
“She is much cheaper than you think,” Karen grinned. “She even does the grocery shopping, washes the cars and mows the lawn.”
“Mows the lawn!” Stephanie said.
“That’s not all,” Karen whispered, drawing her friends closer. “She’ll eat my pussy and ass until I tell her to stop.” She sat back, waiting for their reaction. Her friends were not prudes. They talked about sex all the time. Karen had made love to both Stephanie and Darla before, so such dirty talk was nothing new to any of them.
“Oh my god! Karen!” Darla exclaimed. “You lucky bitch!”
Tammy was not sure Karen was telling the truth. It seems too perfect. “And, what does James think of her? Is he tapping that fine ass too?” Tammy knew Karen had way too much control over James to ever let that happen.
“What does James think about her?” Karen said. “Let’s ask him,” Karen said, then louder, “Jamie, come in here!”
The girls all assumed she was going to ask the maid to somehow bring James into the room, or perhaps call him.
“Yes, Mistress?” Jamie stood still, waiting for a command.
“Girls, this lovely little thing used to be my husband, James. Now, she is my personal toy, and my sissy-cuckold servant. Isn’t that right Jamie?”
“Yes, Mistress.”
“No way!”
“It is James! Or it was James, I mean!”
“What brought this on?” Darla asked. “How did you make him change like this?”
“He was already half way there,” Karen said, “I just needed to give him a little push. Isn’t that right, faggot?”
“Yes Mistress.”
“And, I got tired of his worthless little pecker and decided to get some real cock for a change.”
Tammy giggled. “Is his dick really that small?” she asked.
“Jamie, show the girls your clitty.”
“Yes Mistress.” Jamie’s face was bright red with embarrassment. He lifted up his skirt and pulled down his panties.
“Oh my! It is small!”
“And you keep his little thing locked up too!”
“Well, it’s useless, and I can’t stand looking at it anymore,” Karen said.
“Why on earth did you marry him in the first place?” Stephanie asked.
“Show them your tongue, Jamie.”
Jamie extended his long tongue and wiggled it back and forth and lapped up and down.
“Oh, my!”
“Nice!”
“May I borrow him?”
“What do your boyfriends think about him? Doesn’t he get in the way?”
“Oh, no. I’ll send him to his room until I’m finished, then let him lick all the cum from my pussy; he loves cum. Or, sometimes I’ll let him participate, especially if I have more than one big dicked stud over at a time. He sucks them to get them ready to fuck me and then helps by licking their balls, licking my clit; anything I ask him to. Sometimes, they like to fuck the little faggot too. He loves it!”
“Ooooh! Do you think you can help make my Timmy into one too? His dick isn’t much bigger than Jamie’s!” Darla said.
“Timmy? A sissy-cuckold-slave like James here? I’m sure I could help. Timmy is half way there already. I’ve seen him checking out other guys. He probably a closeted sissy-faggot like Jamie was. What do you think, Jamie? Would you like a little faggot friend to play with?”
“Yes, Mistress! Thank you Mistress!”
“I want you to make my husband a sissy-cuckold too!” said Tammy. “Will he do anything I ask him to?” Tammy asked. Then in a lower voice, “Like, let me pee on him?
“Oh, if he’s trained right, he drink your piss and ask for more!” Karen said. “Isn’t that right, Jamie?”
“Yes, Mistress.”
“Well start tomorrow, girls and make our plans,” Karen said. “But in the meantime, my pussy needs a good licking. Anyone else?”
“Uh…, can I try out his tongue, Karen?” Stephanie asked. Karen had been trying to get into Stephanie’s panties for years now.
“Absolutely!” Karen said, stripping off her clothes. Her friends did the same. “Does anyone want to fuck his ass? I have some strap-ons.” Karen added.
“Oh, that sound like fun!”
“Jamie, go fetch the dildos and harnesses. The big ones, and the lube. And change into your slutty underwear, I don’t want your new outfit ruined.
“Yes, Mistress!”
Epilogue
A year passed. Jamie developed into a sexy, vivacious woman. Her hair grew long and luscious. Her augmented breasts were large, full and firm. Her ass and hips were round, her lips were plump, and her skin was soft and silky. She spent her days cooking and cleaning for her Mistress. She spent her nights licking her Mistress’ pussy and ass, or fucking Karen with dildos until she was satisfied. She spent her weekends hoping Mistress would bring home a ‘treat’ for her after her night out, or bring home a friend or two and ask him to join them. She pranced and danced through the house, happily doing her chores, while she longed for the ‘special’ nights out on the town, where her Mistress would humiliate her in front of strange men and women and force her to satisfy them.
One day, Mistress ordered her to clean the house thoroughly, prepare some hors d’oeuvres, and get ready for a party. She told her to make sure her ass-pussy was clean and ready for use. Karen provided her a new, even skimpier maid uniform to wear that evening. Her large breasts were nearly falling out of the tight, black top and her soft ass was framed by the skimpy black skirt, trimmed in white. High-heels, black stockings, garters, and black cap completed the ensemble. She wore her black chastity cage and a black studded butt-plug. Both were visible as she pranced about and bent over to perform her chores.
Mistress Karen’s guests began to arrive and Jamie met each of them at the door with a small curtsey. She made sure each person had a drink and something to eat. She happily noticed all the guests were all male. It should be a fun night! They groped her freely as she scurried about. Jamie opened the door to find Ken and his friends from the bar that glorious night (Karen and Jamie had returned to that bar at least once a month), the stock-boys from the grocery store, many of Mistress’s big-dicked boyfriends, and a few others she had made him pleasure on their infrequent outings. Darla and her cuckold in training also arrived. And lastly, his good friend Sheila knocked on the door. They squealed at each other like little girls.
After everyone had settled down, Karen stood up made a short speech. To Jamie’s surprise, she announced that the party was for him! A cumming-out party for her sissy, faggot, cock-sucking, cum-guzzling slut! Jamie was so happy and embarrassed! She received a round of applause from all the men in the room. Even her Mistress clapped for her!
Karen instructed everyone to have their way with Jamie, any way they wished, and for as long as they wanted. Karen, Sheila, Darla and her sissy husband would help out anyway they could. She instructed Jamie to put some porn on the large screen TV and then do a slutty dance for the men. Jamie danced sensually, as if she was alone in the room, as she had done so many times before. She showed off her soft ass and full breasts. Before long, someone grabbed her and pushed her to her knees. A huge cock slapped her face and she began to suck it.
Someone else pulled her legs apart and replaced the butt-plug in her greasy ass-cunt with a hard, throbbing cock. Jamie looked around and saw Sheila, Karen, Darla and her husband Timmy (now called Tiffany) all sucking cock. Soon all of the girls had a cock in their pussy and another in their mouths.
Jamie was fucked hard and repeatedly until she squirted into her little cage. She sucked cock after cock until her belly was full, and, when she belched, she tasted sperm. She coaxed a tired, wilted, cock hard again for Karen and then licked them both as his Mistress was fucked. Jamie cleaned both of them afterwards.
They each took cock after cock until they were sore and tired, and then they sucked and fucked some more. The men left them covered in cum, exhausted on the floor or sprawled out on the cum-covered couch. Darla and her sissy-husband were the last to leave.
Jamie cleaned Karen and Sheila’s pussies for them and the three took a long, hot shower together before crawling into bed. Jamie lay between them, their strong arms around him protectively.
“Thank you Mistress Karen, thank you Mistress Sheila,” he said gratefully.
“Good night, faggot,” they said in unison.
Jamie smiled, content with his place in life, and soon fell asleep.