The Mammoth Book of Threesomes and Moresomes

Darlene’s Dilemma

Andrea Dale

Darlene had surreptitiously squirmed her way through breakfast, trying to no avail to find a comfortable position on the chair. She was stubborn enough not to want to admit there was no comfortable way of sitting in public when there was a butt plug buried in your ass.

Of course, the wriggling around made it worse, made her more aware of the silicone toy inside her. It wasn’t terribly big — she wasn’t into harming delicate tissue — but it was there, and it brought a flush to her face any time Jaden or Sienna lubed it up and told her to bend over.

They allowed her to wear panties to breakfast, because they had a respect for the hotel’s antique chairs and didn’t want her staining the cushion.

Sienna was wearing a plug, too, but somehow she managed to look completely unconcerned and entirely comfortable. She didn’t find it as deliciously humiliating as Darlene did.

Sienna was playing on the bottom today, kinky switch that she was. Darlene was pretty much always a sub — it was just her nature — although occasionally she could be persuaded to punish Sienna if Jaden thought Sienna needed two people topping her. Darlene did enjoy that, because it meant she could do all the things to Sienna that Sienna did to her. Turn about was fair play, after all.

It was a perfect arrangement for all of them: Jaden Powell, rock star extraordinaire; Sienna, his creative wife; and Darlene herself, their willing girlfriend.

Jaden had reached middle age with a grace that everyone envied. It pissed off a few people, too. Exercise and eat right, and still watch things sag. Live a life of decadence, of drugs and booze and wild nights, and continue to look like a god. He no doubt had a portrait in a safe-deposit box somewhere.

His sexiness had something to do with that British accent, still apparent even after years of living in homogenized, sundrenched Hollywood. His voice had a way of reaching out and caressing you, stroking over your skin, teasing its way into your panties. .

The blue eyes, craggy features, wicked grin, devil-may-care tousled brown hair that had graced a thousand posters didn’t hurt either.

Jaden was in rare form this week. Their trips to the Victorian spa always involved some new game, something nasty and creative that Jaden dreamed up. (Or sometimes that they all dreamed up together.)

After they’d gotten settled in yesterday, he announced that Darlene could have all the orgasms she wanted for the duration of their stay. He might manipulate them a little, hold them off to make them more intense, but otherwise it was no-holds barred.

The catch was, she could have them any possible way except with the benefit of something in her pussy. No cocks, no dildos, no internal vibrators. No fingers or fists either.

“It’ll be a fun experiment,” he’d said, his sensual mouth curving into a wicked smile. “Let’s see how many ways we can make you come without something inside you.”

Darlene’s cunt had promptly spasmed at the thought. Immediately she felt bereft, felt like she needed nothing more than something deep inside her, stretching her out, massaging her G-spot.

Of course, she’d promptly started getting wet, too. Most kinds of play talk got her wet and, right now, her excellent imagination was coming up with all sorts of ideas about how she could be brought to climax with tongues and fingers and vibrators, by nipple play and butt play.

She didn’t realize just how desperately she’d miss cock until she saw Sienna getting some earlier. Sienna, with her face and chest blushing the same colour as her strawberry-blonde hair as she came.

Yes, Jaden was in quite a mood this morning. After they’d had a little time to relax after breakfast, he went to work on the two of them.

First he’d had them remove each other’s plugs. Darlene had removed Sienna’s first, which she regretted soon after. She’d simply popped it out, whereas Sienna took her own sweet time, fucking Darlene’s ass with the plug before slowly removing it, bit by excruciatingly arousing bit.

Whistling cheerfully — one of his own hits, Darlene recognized — Jaden helped her into a soft leather dildo harness, complete with a bright purple dildo that had a strong upwards curve to it. The end of it in the harness had a vibrator that snuggled up against Darlene’s clit, which poked out between her shaved, glistening lips.

Oh, this could only be good, right?

He turned on the vibrator to its lowest setting, just enough to make her dance a tiny bit.

Around her waist he buckled a strap with cuffs on either sides for her wrists. He strapped an identical one around Sienna’s torso.

Hmm. Getting interesting.

The low hum added to the excitement from the butt-plug breakfast.

He had Sienna stand with her legs spread apart, instructing her to hold herself open. At his command, she dipped her fingers in then fed her glistening juices to Darlene.

Sienna tasted sweet, like thick sugar water. Darlene would have been happy to go down on her, both because she enjoyed it and because she usually got a nice reward for a job well done, but that wasn’t in Jaden’s current plans.

“Put the dildo into her,” he said to Darlene. “Slowly, now.”

Darlene bent her knees to bring the head of the dildo down to the right height, and nestled it between Sienna’s parted lips. Slowly she stood, pressing the fake cock up into Sienna’s cunt by measured degrees. Their difference in height meant that when she was standing straight again, the dildo would be comfortably up Sienna.

Her thighs trembled, but only a little. All those Pilates classes were paying off.

Sienna panted as the cock filled her. Darlene’s own pussy felt empty by comparison, reminding her that she wouldn’t be getting the same treatment. She tried to console herself with the fact that she had the vibrator on her end, but it was only a partial victory.

Jaden secured Darlene’s right hand into the cuff on Sienna’s waist, then Sienna’s left hand to the cuff attached to Darlene. It forced them to stand close together, forced the dildo deep into Sienna and the vibrating end harder against Darlene’s clit.

“Hold on to the bedpost,” he said.

So that’s why he’d left their other hands free.

Darlene looked at Sienna. They both wanted the same thing, and they’d been together long enough that they didn’t need words. By unspoken agreement, they both moved their hips. Even this close, they were able to part a little bit, pulling the dildo a short way out of Sienna, then shoving it back in as they bucked close again. It wasn’t nearly like the full range of fucking, but from the way Sienna’s nostrils flared, it was obviously good for her.

Jaden’s hands flew to each of their necks, his fingers weaving through the hair at their napes and tugging. They both froze, heads back to avoid the pain of having their hair pulled.

“I didn’t say you could move,” he said.

They waited, achingly aroused but unable to do anything about it, while he rooted around in their luggage.

Finally he found what he was looking for: a pair of nipple clamps and a chain that attached them together. Sienna had pierced nipples with rings, something Darlene had never been interested in doing. But her own nipples were very sensitive, and Jaden often used that to his advantage — like now.

He snapped the clamps on to Darlene’s nipples. She sucked in her breath at the fiery pain that slowly transmuted into a deep, aching throb. Then Jaden showed just how wickedly inspired he was today.

He threaded the chain through the hoops in Sienna’s breasts and connected the ends to the clips on Darlene. The short chain forced them to stand even closer together, pressing their breasts against each other, their hard nipples further aroused by the contact.

If they tried to pull away, their sensitive buds would be stretched and tugged.

A fresh wave of moisture and desire rippled through Darlene’s empty pussy.

Jaden made sure they were both comfortable (under the circumstances), then stepped back to admire his handiwork, caressing their asses, checking on the vibrator and bumping it up a notch.

And then he brought out a bright red leather slapper, the kind with holes in it for an added sting.

Darlene squealed under her breath, and Sienna moaned. Darlene loved getting spanked, but Sienna had something of a love-hate relationship with it. She enjoyed it, but tended to squirm all over the place to get away.

She wasn’t going to be able to do that now. Not unless they were both willing to put up with some serious sting in their breasts.

God, he was inventive!

“You can kiss each other if you want,” Jaden said. “In fact, I’d like that very much.”

It was as good as a command, and they both welcomed it. Darlene loved the way Sienna’s soft lips and small tongue teased and caressed her mouth.

He started on Darlene first, with warm-up blows that didn’t do much more than tingle. She knew that wouldn’t last for long. She was just starting to feel the heat when he switched to Sienna, spending a little more time on her to bring her up to the next level.

What Jaden loved most about that particular slapper was its colour. His goal, he always said, was to make their asses the same vivid hue of scarlet.

He generally achieved his goals.

Back to Darlene. Now her ass started to sting. There was no escaping the blows. He mostly concentrated on her butt, which meant many of the hits were right on top of each other, not giving her sensitive flesh time to recover from the last slap. She bit down on Sienna’s lip, keening lightly.

It hurt, but it was a good hurt, and by the time the sensations made their way from her brain and back down, they’d turned to pleasure. The bump of the vibrator against her swollen clit still wasn’t enough to bring her off though. Not yet, at least.

Darlene was mostly able to stay still, but the same wasn’t true of Sienna. She flinched with every blow when Jaden returned to her side, which tugged at the chains connecting their nipples, sending streaks of painful pleasure through Darlene.

It was all Darlene could do to keep hold of the bedpost. Her ass was on fire, her nipples were on fire, and the excruciatingly light buzzing between her thighs wasn’t enough to tip her over the edge. She could smell her own arousal, could smell Sienna’s, and it only made her hornier. She tried to distract herself by kissing Sienna, but then she thought about how good Sienna’s tongue was when it was between her legs, licking her.

Jaden tossed the slapper aside. He caressed both their butts with his large hands, and although his touch was barely more than a light brush, they both yelped.

He laughed at them. He disconnected the chain, although he left the clamps on Darlene, and unhooked their wrists from each other’s cuffs. Then he had Darlene pull the dildo out of Sienna. As it emerged with a squishy pop, Sienna whimpered.

At least she’d had something inside her. Darlene inwardly pouted.

Still, she had the vibrator on her side. Jaden positioned Sienna at the side of the bed, bending over, her crimson ass wiggling in the air. Jaden gave it a couple of slaps with his hand, causing her to cry out against the bedspread.

“You want me to fuck her?” Darlene asked.

Sienna mumbled something that sounded suspiciously like “Yes, please.”

“But of course,” Jaden said. “Sienna, open wide.”

Sienna reached down and spread her shaved, glistening lips. Darlene set the tip of the dildo between them.

“Hold on,” Jaden said.

She stopped, and he reached between her legs to turn the vibrator on full force.

“Have fun, you two,” he said, amusement dancing in his voice. They both knew what he meant — it was their cue to come, and come again.

Darlene was so on edge that she knew it wouldn’t take long. It took only a few short moments before she felt the familiar surge rising inside her, focusing down and centring on her clit.

Closer. . closer. . oh God. . there!

Her climax grabbed her like a vice, then shook her into a million pieces.

The orgasm made her pump her hips in a flurry of motion, which tipped Sienna over the edge as well. Their cries mingled as they shuddered through their releases.

When they’d recovered, Jaden unbuckled the harness from Darlene because her hands were still shaking too hard to manage the clasps. Sprawled on the bed, he had them lick and suck him, using their mouths and hands to bring him to his own completion.

They collapsed on the bed in a happy puppy pile. Darlene thought she might have even dozed off for a bit, before Jaden stirred again.

“How about a soak in the baths before lunch?” he asked cheerfully.