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Sissy Staycation
The Sissy Staycation
Dennis was so close to cumming he couldn’t see straight.
The vibrator up his ass hummed against his prostate. His meager dick was slick with precum, with the head just popping out over the top of a pair of lacy panties.
He planted his feet on the coffee table in front of the couch, spreading his legs. He caressed his aching balls through the panties with one hand while the other hand toyed with his nipples under the thin, lace babydoll that covered his top. He watched the two men on the TV. One of the men wore a maid’s outfit, wig, and makeup and was being deeply, and loudly, fucked by the other man.
His cock lurched as the man on the screen pulled out and spewed his cum all over the other man’s maid outfit. He pinched his own nipple hard, and he felt his load rising up in his balls.
And that’s when the front door opened and his wife walked in.
**
“Sure you don’t want to try to come? You won’t feel bad the whole week,” Emily said as she picked up her suitcase. Behind her, her sister Heather and brother-in-law Bill were at the open front door, waiting. Turned sideways, Emily’s curves made a perfect silhouette, breasts pushed up into a too-small top, tight shorts hugging the tops of her long legs. At 35, she continued to turn heads wherever they went, which led to her being horny as hell when they got home and plenty of fucking for him. And while she seemed to enjoy it, he had realized early into their marriage that his meager offering of a dick just didn’t do it for her.
Heather was a younger, slightly smaller version of her sister. Her tits were a cup smaller, and, to Dennis’s eyes, a bit firmer, not that his wife had any complaints. Her tits stood out straight with or without bras. Heather’s yoga pants showed her tone legs and lack of panties, something Dennis always took time to appreciate.
Heather was in such great shape thanks to her husband, a black gentleman who owned a chain of health clubs throughout the city. And instead of using models for their ads, Bill used his own pics of him working out. The man was ripped. And at the same time, he was really the man of the family after he married into it. Dennis felt like a distant second place next to Bill.
Dennis was on the couch, covered up with a blanket and looking miserable. He shook his head no, making it look like it hurt to move that much.
“Denny? It won’t be the same without you,” Heather said. “You’re always so much fun.”
“Yeah, man,” Bill laughed. “I’m not sure I want to be in a car with these two for four hours all by myself.” Heather gave him a playful swat across his tight chest. He smiled at her and she stuck her tongue out at him.
“I don’t want to have to make you guys stop every exit so I can run in to take a shit,” Dennis croaked.
Emily turned to the other two. “He was up almost all night going to the bathroom. Yeah, I have to agree with him on this one.” Back to Dennis, “You get some rest and we’ll call when we get to the beach house.”
Dennis pulled a hand out from under the blanket and gave a feeble wave.
He laid still as he heard them get into Bill’s Hummer. Listened to it pull away. He remained motionless for half an hour until he felt certain that they weren’t coming back for something they had forgotten.
Five minutes later, he was upstairs in the shower, a rectal douche up his ass and pushing water into his bowels. The laxative he had taken yesterday had done a good job, and it didn’t take long until he was clean as a whistle and then out of the shower and, still naked, into the bedroom.
He shuffled through Emily’s lingerie drawer, packed with the frilliest, girliest lingerie he had bought her over the past year. She had oohed and aahed over each gift of the lacy clothing and had worn each item at least once while Dennis fucked her.
But he hadn’t bought any of this for her. They were all for him. His slender body wasn’t too much different than his wife’s aside from her terrific tits, and now he had a whole week to try them all on without interruption. Under the guise of the trip to the beach house, he had even managed to snag a week off work. No one would call him in for the next seven days as he got to go around his house either naked or wearing lingerie.
He took a good fifteen minutes to decide what to wear, rubbing the satin panties, slips, and babydolls over his cock as he pulled them out and considered others. He settled on the purple see-through babydoll with matching g-string panties. He set some of the others out on the bed, knowing that he would be wearing them soon enough. He strode out of the room, his dick jutting up out of the small triangle of flimsy material.
A quick stop in his home office to pull out the small but growing selection of dildos and butt plugs from their hiding spot in the lowest drawer of his desk, and he was ready for an afternoon of lust that would get him ready for an evening of self-fucking and cumming. He swore to himself that this time he would actually eat his own cum, and it made his dick twitch in the panties just to think about it. He had gotten close a few times, chickening out at the last second with his cum pooled in his hand.
He pulled up a porn site on the smart TV and as the sissy maid began to suck the other man’s long dick, Dennis lubed up the beaded anal dildo. He slipped it past the string that ran across his hole and slid the tip in. One bead. Then next. He relished the feeling of his ass tightening as the next large bead pushed past his tight hole and slipped inside. He would gasp as each one slipped through until he had it buried up to the dildo’s base.
Soon he was fucking his ass with the dildo in synch with the man on the TV who was now fucking a new sissy maid. The plot, such as it was, canlı kaçak bahis revolved around a rich man who staffed his entire mansion with sissy maids, who were always available to suck him off and/or take the master’s dick up their ass. It was one of Dennis’s most revisited fantasies to be one of those sissy maids. He had considered getting Emily a maid’s outfit but thought that may make her suspicious.
He could feel the cum rising up in his balls and pulled the dildo out, gasping at the sudden emptiness. It took a minute to catch his breath.
He reached over and pulled over the large vibrating but plug. It slipped into his gaping, lubricated hole with little effort. Dennis sighed as his ass closed back around the base. He pushed the button on the bottom of the plug and his dick jerked as the waves of vibrations hit.
He rubbed his balls. Pinched his nipples. He wanted to cum without touching his dick. Just let the jizz spurt across his belly.
And then the door opened.
Emily stood there, suitcase in hand. Mouth as far open as it could go.
“The fuck?” Emily gasped.
Emily stumbled into the living room. Heather was right behind her and once clear of the door, Heather saw just what “the fuck” it was and opened her mouth in a silent “WOW!”
“Everything okay?” Bill asked as he walked through. He saw Dennis, legs splayed. Tip of the butt plug vibrating just beneath the g-string. “Holy fuck!!”
Dennis felt it. His balls tightened. His ass tried to grip the butt plug and push it out at the same time. His dick jerked and twitched uncontrollably. Dennis grunted as he came. Great streams of cum shot from the tip of his dick over the panties. It coated the lower part of the baby doll. One stream shot far enough to land on his chin.
And as his wife, sister-in-law, and her husband watched, Dennis groaned and shuddered with the intensity of his orgasm.
**
Dennis sat on the dining room chair. He was still in the lingerie. Emily wouldn’t let him change. And the butt plug still vibrated in his ass. The base against the wooden chair amplified the buzzing sound. He squirmed as his dick rose from the pressure and vibrating against his prostate. He already wanted to cum again.
There had been a problem with the Hummer. It kept overheating and Bill had made the call to turn around get Emily’s car, nursing his massive vehicle back.
At first, Dennis was horrified. And when they made him walk to the dining room, he had to shuffle because of the plug that filled his ass. Emily had even ran a hand over one of his ass cheeks, right before she smacked it. He had leapt ahead with a tiny squeal of pain. And delight. And as he sat there watching them plot, he realized that he was no longer embarrassed to be dressed like this in front of him. His secret was out and it felt as if a weight had been lifted.
The other three sat at the other end of the table, whispering to each other. At first, Bill looked unsure, but after Heather slid her hand down under the table, he seemed to come around to whatever they were cooking up.
Emily stood up and walked to Dennis. She looked down and saw his erection, precum dribbling out of the tip, soaking the top of the panties. She reached down and took his dick in her hand, stroking it. Twisting her hand around the slick head.
Dennis tipped his head back and moaned. God that was amazing.
“Like that?” she asked.
Dennis could only nod. Like was an understatement. And then he remembered Heather and Bill were witnessing this. And he moaned even more.
“And I thought Heather was the slut of the family,” Emily chuckled.
“Hey!” Heather laughed.
Emily let go of his dick and stood up. He opened his eyes and begged, “Do that again. Please. The vibrator. I want to cum.”
“You already had your turn,” Emily said. She crossed her arms. “Here’s what’s going to happen now. We are going to spend our vacation here at home with you. And since our plan was to fuck for the whole week at the beach house anyway,” Emily continued, ignoring Dennis’s shocked look, “we have decided to stick with that plan and just fuck all week long here. Bill was looking forward to fucking two women, but now, he’ll get to fuck three.”
Dennis looked down the table and saw Bill’s big smile. Perhaps it was because of whatever Heather’s hand was doing under the table. Perhaps it was at the thought of all the fucking he was going to get to do for the next week.
“And since you lied to get out from going with us, you will do anything and everything we say for the next week. Got it?”
Dennis nodded. A thrill raced through him as he hoped this meant what it sounded like — he would get to be a sex slave.
“Stand up,” Emily commanded. Dennis stumbled to his feet. “Lean over the table.”
Dennis leaned forward until his chest touched the cool surface. He shivered as his nipples reacted to the chill. He clenched his ass cheeks as the vibrator caught him again.
“Let’s take care of that before it causes any more problems,” Emily said. Dennis felt the g-string slip down his legs. “Spread ‘em, dear.” He spread his legs and felt the butt plug being pulled out. Emily took her time, twisting it as she pulled on it until it cleared his rim and slid out.
Dennis sighed at the feeling. He started to stand.
“Not so fast,” Emily said. She put a hand on his back and kept him pinned to the tabletop. “We need to break the ice, so to speak. Bill.”
Dennis looked down the table and saw the Heather was alone. Then he felt Bill’s cock at the entrance to his ass. He held his breath as the large tip of the unseen dick slid into his gaping, lubricated hole. It felt bigger than the plug. And then it kept sliding in further and further. Dennis caught his breath as he felt Bill’s balls swing against his own.
“Holy fuck,” Dennis breathed. perabet giriş He felt so full. The pressure made his own cock reignite.
“You said it, man,” Bill said. Emily made a coughing sound. “Right. Sorry. You said it girl. She is so tight!”
Bill slowly worked his cock back out, leaving just the bulbous head inside Dennis’s cavity. Dennis held his breath as Bill slid his length back in, feeling every bump and vein of Bill’s cock. This was so much better than a plastic cock. Dennis could only moan and gasp as Bill worked his ass over slowly at first. Soon, the tempo picked up and Bill was fucking him hard, slamming into him so hard, the table scooted along the floor.
Dennis tried not to make too much noise, but couldn’t help himself. He moaned and gasped the whole time that Bill rammed his massive black dick into Dennis’s ass.
Dennis looked down the table and saw that Heather was gone. Was she watching her husband fuck another man from behind them?
A hand grabbed his own cock and he turned his head to the side. Emily knelt there, arm extended out under the table
“My. You are really enjoying this,” she purred. A stream of precum dribbled out of his raging erection. “Let’s change that.” Before he could ask what she meant, she slapped his balls. Dennis grunted and tried to pull away, but Bill’s thrusts kept him pinned to the table. A few more slaps from his wife and Dennis found his erection fading, but he missed her slapping his balls now.
Meanwhile, Bill kept pounding his ass and Dennis was starting to wonder how long the man could last. The answer came soon enough as Bill suddenly pulled out. Dennis had just enough time to register the emptiness when Bill’s hands grabbed his shoulders, spun him around and pushed him down to the hardwood floor. A moment later, Bill’s dick was pointed square at Dennis’s face and Bill was running his hand up and down the 12-inch long shaft that was so thick his fingers barely touched on the other side. Dennis was amazed to think that that monster had been in his ass.
Bill grunted. “Open your sissy mouth, girl,” Bill ordered. Dennis did, just as the first shot of cum shot out of Bill’s cock and struck him full in the mouth with such power that some of it rebounded out and dribbled down Dennis’s chin. Bill kept pumping his dick as more jizz shot out. Most went into Dennis’s mouth, while some hit his cheek, his chin, and finally, his chest as Bill’s load was spent with one final thrust and grunt
Dennis realized he now had a mouthful of cum, and not his own as he had planned. It was smooth and a little salty. Acidic in a pleasant way. He swallowed without being told. He opened his mouth as Bill shook his dick over Dennis’s upturned face and let the last few drops of cum fall into his open mouth. Bill turned and walked away to the couch. His dick, even as it softened, hung down over the edge of the couch and Dennis found himself wondering how much of it he would be able to take into his mouth.
“Here. You can’t look like a lady like this,” Emily said as she took a finger and scooped up the sperm from around his face and pushed it into his mouth until it was all swallowed. She stood up and pulled him up with her. “Let’s get you ready for your staycation.” She took his hand and led him towards the stairs, past Bill who was leaning back on the couch, his cock spent for now.
And for the first time, Dennis realized that Heather wasn’t there.
**
Upstairs, Emily ordered him to strip and get in the shower. She stripped too, her tits bouncing and jiggling every time she moved and Dennis realized he was getting hard again. Shit, wasn’t there anything that didn’t turn him on right now?
She stepped into the shower and began lathering him up, making sure any cum that she had missed got washed off. She fondled his balls and twisted the head of his cock around until he was almost ready to cum again. She stopped and slapped at his erection until it went down. He whimpered. “We don’t want you spilling your seed just anywhere. You will get to cum only when and where we let you. That’s your punishment for lying to me about why you didn’t want to go on vacation,” Emily said.
She shaved him from his neck down, concentrating on his testicles and legs until he was smooth.
Back out in the bedroom, she stood at the foot of the bed, which still had the other lingerie sets he had been considering wearing just a few hours before. “Guess you really weren’t buying these for me,” she laughed, and picked out a sheer robe and matching g-string.
“I’m back!” Heather called out.
“Up here,” Emily yelled.
A moment later, Heather was at the door and cast an appreciative eye on Dennis. “She’s looking better. But this will seal the deal,” Heather said, holding up a shopping bag. Dennis recognized it as the sex shop he had bought some of his dildos.
Heather pulled out a chastity cage and a large bottle of lube. Dennis could tell there was more in the bag, but Heather left those items in the bag for now. Emily took the cage and knelt in front of Dennis. After a few tries, she had his cock securely fastened inside the cage, the ring snug against his balls. The cage kept his dick that he had once thought of as average until he had seen and felt Bill’s massive member an hour ago, small and pointed down. Every time he moved, it swayed, reminding him that it was there.
“Let’s try it out,” Heather said as she ran some lube over the beaded dildo he had been using earlier.
A moment later, Dennis was face down on the bed, his cock stuck under him in the cage, as Emily and Heather took turns fucking his ass with the dildo while the other sat in front of him so he could eat their pussies. Dennis didn’t care what was happening to his ass, though he was certainly enjoying perabet güvenilir mi it, as this was the first time he had seen Heather’s pussy and ass. He had imagined it plenty of times and was enjoying tonguing it for all he was worth. She held his head against her snatch and at one point, took his head in both hands and pushed it up and down her slit, masturbating with his tongue.
“Where is everyone?” Bill called out. His erect black dick entered the room first and he stopped at the door to admire the action. Dennis was now on his back as Emily continued to fuck his ass with the dildo. His caged cock bounced and jiggled with each thrust, and precum dripped out at the top of the cage, but Dennis was starting to get frustrated. The inability to have an erection even as his ass was filled with each thrust of the dildo made him moan and desire release even more. Heather straddled his face, grinding her pussy over his mouth. She shuddered as she squirted a stream of her pussy juice onto Dennis’s face. She looked over at her husband and his cock.
“Thank God you’re up,” Heather smiled. “I need an actual dick in my pussy. Now!”
Bill strode into the room, his dick swinging left and right, pointing ahead as it did. Heather scooted to the edge of the bed and pulled her feet back and up, giving Bill the widest view of her pussy she could manage. Her juice dripped out of her pussy and trickled down past her asshole. She glistened with sweat and anticipation.
Emily watched Bill’s dick moving and Dennis saw her lick her lips. He understood why she had been looking forward to being fucked all week. Was that the plan if he had gone, too, or had it been decided only after she realized Dennis wasn’t going with them? He thought he might never know, but he did know that he was looking forward to seeing Bill put that huge thing in his wife’s pussy and ass.
“On your knees,” Bill told Heather, and she flipped around, giving him a perfect view of her round little ass and spread pussy. He slicked up the head of his cock by running it up and down her slit. It was Heather’s turn to moan now as her husband slipped his cock into her in one strong push.
“Fuck me,” she breathed. “God fuck me with that dick!”
“You got it, babe,” Bill said and rammed into her so hard her tone leg muscles shook with each thrust. Her firm breasts hung down and swayed back and forth. She looked over at Dennis, who was watching keenly. “Slide over here and suck my tits,” Heather ordered.
Dennis did so, as Emily moved with him, never letting the dildo out of his ass. Dennis slid under his sister-in-law until he came to her amazing, firm and tanned tits. It took a few tries to catch one of the nipples in his mouth as they swung over his face. He held on to it as he sucked and licked at it. Then it pulled out and he aimed for the other breast.
After a few minutes in heaven sucking Heather’s tits, Dennis heard Bill grunt, “Gonna cum, babe.”
“Help him out, Dennis,” Emily suggested, and began to push him forward. He got the hint and slid further down Heather’s shaking body until he was at the edge of the bed. Above his face, Bill’s balls swung with each thrust into Heather’s snatch. Dennis saw Bill’s dick, coated and shining with her pussy juices, pistoning in and out an inch from his face. Bill’s balls slapped against Dennis’s forehead and across his nose.
“Lick me!” Heather cried out. Dennis reached up with his tongue and licked the entrance to her pussy as Bill kept up his pace. “My shaft sissy! Lick my shaft!” Bill growled. Dennis changed his angle and a moment later Bill’s long dick was sliding across his tongue, pulling a wave of Heather’s sweet juices out each time. Dennis lapped it all up as fast as he could.
Heather reached forward and fondled Dennis’s swollen, purple balls in her hand. His balls were now almost bigger than his caged cock after the relentless fucking his ass had been getting and the near-constant pressure on his prostate had filled them with his own cum that was dying to get out.
Heather smeared his precum around his balls and then squeezed them. Dennis yelped in pain. Heather tipped her head down and flicked her tongue across the exposed tip of his cock. “Ohhh,” she purred, “You are so close to a sissygasm.”
“Me first,” Bill said as he shoved his dick full-length into Heather’s pussy. Dennis watched as Bill’s balls contracted multiple times as he shot his load into his wife’s womb. It throbbed and throbbed as he came. Dennis was in awe of the sight. After a minute, Bill began to pull his dick out, bringing a combination of his cum and Heather’s pussy juice with it. It dribbled onto Dennis’s mouth and he opened up to take it in. Once Bill had the head out, his long dick plopped onto Dennis’s face and he ran his dark cock along Dennis’s waiting tongue. “Yeah girl, clean it up good,” Bill said.
After a minute, Bill stepped back and Dennis thought he was done. Then Heather leaned back, planting her pussy squarely over Dennis’s mouth. “Clean it all out, girlfriend,” she teased. She squeezed her pussy and a huge dollop of white cum slid out of her fucked hole and right into Dennis’s mouth. She continued to squeeze her pussy, each time pushing more of Bill’s copious cum into a waiting mouth.
After a few minutes, Heather fell off to the side, working to catch her breath.
Emily pulled the dildo out of his ass with a quick jerk. Dennis nearly sat up at the sudden movement. He grunted as his little dick leaked a steady stream of his own cum down across his balls. His caged dick twitched and twitched as he sissygasmed.
Emily was right there, catching the cum in her hand. After Dennis settled down, everyone watched as Emily brought her handful of his cum up to his mouth and fed it to him until he had licked every drop off of her hand.
Dennis sat back, content with the fucking and satisfied that he had finally eaten his own cum.
His wife chuckled as she stood up and headed towards her brother-in-law. “Still got a load in there for me?” she purred.
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