James’ Descent into Cuckoldry 5

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.