A Femdom Cuckold's Weekend

Note: this is a work of fiction that takes place in a world free of STDs and birth control that always works and has no side effects; ALWAYS practice safe sex.

Part One: Ladies' Night

Lying spread-eagled in a king-sized bed, a man's wrists and ankles were restrained to the bedposts as his girlfriend-turned-Mistress, Vera, checked his bounds. Once satisfied, she grabbed a few things from the table on the right side of the bed and then roamed her eyes across the man's nude body, which was free of hair except for a landing strip over his pelvis thanks to laser hair removal. She too, was naked, displaying her beautiful feminine form. Her legs, athletic from years of jogging, led up to a small, yet shapely ass and her small frame helped her maintain a lean figure. In her mind, though, her smaller stature was a double-edged sword because it also limited the size of her breasts to either an A or B-cup size (depending on her self-image at the time) and she always wished they were bigger.

As the man looked at her, her bright blue eyes locked onto his and she flashed him a cute smile. He smiled back, knowing what she was about to do next. Climbing on the bed, she straddled his chest, facing away from him, and set the items in her hands between his legs. She then grabbed his balls and slipped them into a cold metal cockring before bending his half-hard dick and feeding it through also. The man felt himself fully harden after that and she began slowly stroking his shaft without lube, deliberately avoiding touching the sensitive head.

He gently moaned and she giggled. "Now, now; it's too soon for that, cuckie." She flicked her finger against each of his balls before adding, "We've still got half an hour before I finish edging you." His dick then tensed up, causing his jeweled buttplug to press against his prostate. "My toy certainly loves this part, doesn't he?"

"Yes, Mistress." he replied as her hand began moving faster.

"Which do you think he likes better? The edging or the chastity afterwards?"

Though he could only see her shiny brown hair flowing half-way down her back, he could tell she was smiling. "He definitely loves both, Mistress."

She giggled once more before she pressed his dick against his pelvis and playfully slapped his balls several times. "You always know how to charm your Mistress."

Allowing his organ to stand at attention, she slid back until her moist pussy was hovering over his face, leaving a wet spot on his chest where she was sitting. She then leaned over and wrapped her lips around the tip of his mushroom head. Creating a suction, she rubbed her tongue along the slit and licked up the large, sweet drop of precum. Giving it a kiss, she straightened herself and slid forward to resume her cuckie's edging. Within another minute or so, his orgasm neared.

"One, Mistress!" He said quickly, causing her to let go his manhood and watch it throb. After waiting a minute for him to calm down, she licked up the precum as before and then continued. By the time his edging session was complete, he had counted out to eleven.

She slid back so her ass was over his face and asked, "How does my cuckie show his appreciation for all his Mistress does for him?"

"Thank you for edging me, Mistress." he said, before kissing her little star.

As he began working his tongue around her hole, she moaned. "You're such a good cuckie." Her hands slowly slid across his skin, lovingly caressing her property as she watched his dick throb while it slowly went softer, but never becoming fully flaccid.

She leaned over once more to lick up his precum before grabbing the cold metal base ring of her cuckie's chastity cage and gently pushing his balls through, one at a time. Then, like with the cockring, she bent his dick downward and slid it through. A full erection came back, and she pressed it against his pelvis to give a few firm slaps to her cuckie's sensitive orbs.

"Sometimes I wish I could just press a button and make you completely limp whenever I want." After giving one more, harder slap, causing him to flinch, she added, "Or to make you completely hard and stay that way..." Swinging her leg over and turning around, she pressed her lips to his and then said, "I'm going to go call them...you better be ready to go into chastity by the time I get back or..." she then gently slapped his cheek, insinuating that it would be his balls she would be slapping.

"Yes, Mistress." he replied.

She smiled and then left the room, leaving him to his thoughts. It had taken some time and a lot of practice (especially once he met his Mistress), but he had managed to develop the skill to focus his attention away from sex despite still being horny. So, after ten or fifteen minutes, she came back to a completely flaccid penis.

"Good cuckie." she said as she straddled his chest once more and began putting his dick into the metal chastity cage (aptly named 'Queen's Keep') and tightened the security screw in place with the key that appeared to be on a silver metal lanyard. Once that was done, she hung the key around her neck and then turned around to straddle his face while still being able to look him in the eyes.

"So..." she began with a sly smile as he started licking her dripping folds, "Jack said he was looking forward to meeting Heather, which means while he's making her his bitch, Derek will be the one fucking this pussy." She ground herself against her cuckie's lips. "At least for tonight, anyway...we'll see what tomorrow brings." Running her fingers through his short hair, she asked, "Are you as excited as I am?"

He moaned a 'Yes, Mistress' into her gyrations and did his best to nod, causing a smile to spread across her beautiful face.

"I bet you're more excited than I am, you little slut...and that's why you're mine..." After teasing herself with his mouth and tongue for several more minutes, she got up without orgasm to 'save it for Derek' and unlocked her cuckie's restraints. "Now come help me pick out something sexy to wear for him."

Two sets of hands with bright red nails, freshly painted just a few hours beforehand, went through her lingerie drawer until settling on black fishnet thigh highs, a red, lacy garter belt, and a red lacy underwire bra. It was simple, but for that night, they didn't want her to spend any extra time undressing from something like a lacy bodysuit or a teddy (or even panties). That night was going to be about being sexy while giving the men easy access. The same went for Heather; Vera picked out identical fishnet thigh highs and a red under bust corset with garters. With the lingerie laid out on the bed, they decided that she would pick out skirts and tops later.

Next, she put her hair up so it wouldn't get wet in the shower, where her cuckie sensually used her loofah and lavender-scented body wash to clean her and, as a tease, she used it to wash him. After drying her and himself with a towel, they stood in front of the mirror where she began applying makeup and he began his transformation to Heather.

Part of her interest in FemDom included feminization and 'forced' bi because she loved the idea of a crossdressing man being the woman for another man. Because her current boyfriend and cuckold had been with other men while femininely dressed before they met, she felt lucky to have him and he, too, felt lucky to have met his Mistress who more than accepted his bisexual side.

By no means can her cuckie pass as a woman, but Vera has told him several times that, as Heather, he definitely looks 'fuckable'.

After having applied a light foundation, he went with his usual silver eyeshadow, starting at the corner of his eyes, near the bridge of the nose, and then faded it outward. Next was a little liquid black eyeliner over the edge of the top lid that ended with a slight wing on the outside. He then finished the eyes with mascara on his naturally long eyelashes, something Vera loved (and was jealous) about him.

After applying a light brushing of blush on his cheeks, all he had left was bright red, 'fuck me' lipstick that matched his fingernails. It was all simple and, not being a drag queen, more attractive in both their opinions. Vera, with her natural beauty, didn't apply much more than he did, so they both finished at about the same time.

They then dressed in their lingerie and picked out the rest of their outfits. Her skirt was light blue and hung loose to about midthigh with a slit up that ran up to her left hip and her matching-colored shirt was short sleeve with a generous neckline. Heather's skirt was a simple black one with a midthigh length and her shirt was a black, boatneck long-sleeved affair with lace that ran up the sleeves and went around the neckline.

Since Vera loved cross dressed men with other men, she never wanted him to wear any kind of breast forms because it would make him look 'too feminine' in the chest area. Her cuckie didn't mind, but part of 'her' wondered if it was also because of some insecurities she had about her own chest size, despite her obviously being sexy to Heather and everyone who simply looked at her.

She did, however, insist on Heather having feminine hair and, after she helped put on and straighten the brunette wig that hung down slightly below Heather's shoulders, she had her sissy cuckie help tie her own hair into a single braid. Vera loved it when a man would grab it and pull her head back while he fucked her doggie style. After that was done, she put Heather's slave collar around her neck and attached a leash.

With their clothes, makeup, and hair all done, they put on their high heels. Vera's simply slipped on, but Heather's had ankle straps with locks (her Mistress' idea). With both of them dressed, they returned to the bathroom and looked themselves over in the mirror. With both ladies satisfied, Vera spritzed perfume on her wrists and neck, and then handed it to her sissy cuckie who did the same. At that point, they were ready with just under an hour before the men arrived. Having had nights like this before, Vera loved to have Heather sit at the kitchen table with her laptop and headphones to put her into the mindset of a sissy slut, and that night was no different. Sitting in the kitchen chair with her hands restrained behind her, Heather watched the laptop screen while a list of sissy hypnos played.

Even without the hypnos, Heather was in heat long before Derek arrived, so when Vera closed the laptop and removed the restraints from her wrists, Vera's man could see the pure lust in her eyes as she knelt before them.

"She's certainly horny...how long has she been watching those?" he asked.

"Only about forty minutes, but she also had thirty minutes of edging and orgasm denial earlier." Vera smiled.

"I don't think I would like the orgasm denial part..." he commented as he slipped his hand over Vera's ass, squeezing it while he deeply kissed her.

"That's why you're one of my bulls and not my boyfriend..." Vera replied as she grabbed his length through the front of his pants. Looking down at her sissy cuckold, she asked, "Aren't you going to greet our guest, Heather?"

Reaching up and giving his erection a squeeze, Heather said in a low, submissive voice, "Welcome, Master; I hope you enjoy yourself tonight."

Looking into her eyes with a smile, he replied, "With two submissive sluts to take care of me, I always do."

Derek had been bi-curious, but after he met Vera and her cuckold boyfriend, he found the pleasure of a sexually submissive man too good to ignore. It didn't matter if her cuckold was presented as a man or a sissy, he always enjoyed having another mouth and ass at his disposal. The times when her cuckold was kept in chastity were always the best because his (in this case, her) only source of sexual pleasure was Derek's meaty cock.

When he looked back to Vera, she said to him, "Jack's running a little late, but you can sit on the couch while I make you comfortable and she watches."

Taking Heather's leash, she led them both to the living room and to the couch where Derek sat down with Vera in his lap while her cuckie knelt on the floor nearby. Handing him Heather's leash, she began caressing his chest and shoulders, teasing him to remove his shirt while planting the occasional kiss on his lips. Having other plans, he lifted her shirt up and over her head and began kissing and sucking her neck hard enough to leave hickeys, to both her and Heather's excitement.

His kissing soon roamed down to her chest and, after unclasping her bra and tossing it away, he began biting and sucking one of her nipples while pinching the other, making her cradle his head as she gasped and moaned. One of his hands slid down to her ass where a finger found her little star and began rubbing small circles.

Soon there was a knock on the door and Vera lustfully yelled, "Come in!"

Jack, whom Vera's cuckie had met before, but only as an observing cuckold, entered and said, "I see you started the party without me."

Jack found a perverse pleasure in fucking another man's girlfriend in front of him, but he was never interested in having the boyfriend participate. It was only after talking with Vera and seeing some pictures of Heather (and some porn with sissies being fucked, not that he'd admit it) that he opened up to the idea of fucking 'her'. Upon seeing 'her' kneeling there on the floor, he had to admit that, even though 'she' was still obviously a 'he', 'she' had a pretty enough face to fuck.

After removing his shoes, he walked over, Vera took the sissy's leash from Derek and handed it to him. "She's all yours; I'm sure she's eager to meet you."

Taking the leash, he sat on the couch and pulled the sissy toward him until 'she' straddled his lap with 'her' hands on his shoulders. "You do kind of make a pretty girl." Reaching down, he lifted her skirt and looked at the caged 'clit'. "Mmm, that's always a hot sight, cuckold or sissy."

He then pulled her in for a kiss, pushing his tongue into her mouth and sliding his hands to the sissy's ass. Just as she wrapped her arms around his neck, he broke the kiss and gently bit into her neck below her collar. Closing her eyes, Heather gasped in the pleasure of it and in response, he sharply slapped the slut's ass. When she opened her eyes again, she looked at Vera who smiled just before she slid down to her knees between Derek's legs.

One of Jack's hands slid underneath Heather's shirt, finding a nipple and pinching it, causing her to gasp once more with shaky breath. Releasing his lips from her neck, he looked into her eyes with lust and lifted her shirt up, being careful not to disrupt the wig and ruin the illusion of femininity. Tossing it to the floor, his mouth attacked her other nipple and one or two of his fingers found their way to the sissy's buttplug.

A soft moan escaped her lips and Vera commented, "That's a good slut."

Looking down at her Mistress, Vera held her sissy cuckie's gaze as she licked along the eight-inch length of Derek's cock from his balls to the tip before taking him into her mouth. Heather's caged clit twitched and a large amount of precum spilled out. Jack then switched to her other nipple and gave her ass a second spank, forcing another moan from the sissy's lips.

Pulling back with her nipple between his teeth until it slipped out, he asked, "You're just as much of a slut as your Mistress, aren't you Heather?"

"Yes, Master...especially for cock..." she lustfully replied.

"Then get down on your knees where you belong."

With a smile, she slid down and began undoing his belt and pants. After unzipping it, she pulled his pants halfway down his thighs and he pushed down his boxers, revealing his six- or seven-inch throbbing manhood. As she put it to her lips, he pulled her head down. Dragging her tongue along the underside of his shaft, Heather knew he wasn't going to stop until her chin pressed against his balls. She'd seen him do this with her Mistress just about every time he fucked her, so she opened her throat to prevent herself from gagging.

Sure enough, she soon felt his balls on her chin and his pubic hair between her face and his pelvis with a forceful hand behind her head keeping her in place. Having had much practice with her Mistress' strapon, she could easily take him down her throat, wiggle her tongue around the base of his cock, and keep breathing. What she had a hard time with (at least with a strapon) was doing all that while being throat-fucked.

Jack groaned in pleasure, saying, "That's a good slut...let's see how well Vera taught you to worship cock..."

Feeling his other hand wrap around her neck above her collar, he began using the sissy's face as his personal masturbator. Her hands stiffened, grabbing a hold of his upper thighs as she concentrated on keeping her throat open. She lasted about ten more seconds before it contracted around his organ and she gagged, causing him to bury himself to the hilt once more as she fought to regain control of her gag reflex.

"Not bad, slut..." Jack said as he slapped her face, "but you need more practice."

Pushing her off him, Heather coughed a few times as he stood. Looking down at her, he took a hold of her head, pushed his dick back inside her mouth, and began thrusting; slowly at first. Keeping her eyes locked on his, Heather grabbed the backs of his thighs to brace herself for when he was going to pick up speed, which wasn't long after. The living room soon became filled with the sounds of throat fucking; not just from the sissy, but it was also coming from her Mistress too.

Tears filled Heather's eyes and ran down her face, making Jack stop, smile for a moment, and then slap her face a few times, saying, "You're almost as pretty as when Vera chokes on my cock." The sissy smiled around his dick and bobbed her head back and forth. "You are a good slut, aren't you?" Pulling out his organ without waiting for a reply, he began slapping it against her face.

Vera and Derek had stood, their lips locked, and her leg wrapped high around his hip as he cupped her ass. Breaking the kiss, she said, "I think it's time these two sluts got the fucking they've been waiting for."

"Ask and you shall receive." Derek commented.

"What do you think?" Jack asked the sissy kneeling before him. "Is it time I ruined your little ass?"

Giving him a smile, she replied, "Yes please, Master."

"Good answer, slut!" Mistress giggled.

Heather helped Jack out of his pants and boxers and then stood. He pulled her by her leash and kissed her, not caring about the saliva all over her chin, and then they followed Vera and Derek upstairs to the bedroom; Heather's arm wrapped around Jack and his hand cupping her ass and a couple fingers pressing against her buttplug. Once at the bed, Mistress and her sissy cuckold slid their skirts down their legs and stepped out of them. Derek pushed Vera to the bed and spread her legs so he could taste her wet pussy and Jack positioned his sissy on her knees with her back arched and her head down.

He then removed her plug and set it on the bedside table, slapping her ass a few times to elicit a moan from her lips. He then picked up the silicone-based lube next to where he put the plug and spritzed it over the sissy's pussy and his cock. As she felt his fingers sliding into her, she watched Mistress squeeze the bedsheets with her mouth making a silent O just before she shrieked out and convulsed in orgasm. Just then, Jack put the tip of his dick at her entrance and rammed it inside, causing the sissy to cry out in pleasure.

After another few spanks, he grabbed her hips and ground himself as deeply as he could, enjoying the warmth of his first sissy pussy. Her O-ring tightened up around him, causing him to moan and a drop of precum to flowed out of her clit.

"Such a tight piece of ass...I'm going to enjoy ruining you." Jack said as he pulled almost all the way out before slamming back in.