Double Pleasure

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Present day

Jackie and Tripp had been married for almost two years. Their sex life was incredible, and had even progressed to anal on occasion. Jackie continued to see Cathy when the latter was not in a relationship, or was in an open one. She'd rarely spend the night there, however, as she liked waking up next to Tripp. Cathy fully understood this.

One night at Cathy's Jackie broached a subject that had been on her mind. "Cathy, can I ask you something?"

"Sure, hon, you can always ask me anything."

"Well, you know that Tripp and I sometimes do anal, right? I sometimes watch a little porn and I've become a bit obsessed with the idea of double penetration. I want to be spit roasted but I also want a cock in my ass and pussy at the same time."

Cathy's eyebrows shot up almost to her hairline. "Wow, hon, I'm surprised. You never seemed quite that adventurous sexually. But I'm glad for you if you want to try it."

"I do. Maybe I'll never want to do it a second time but I want to at least try it once."

"So do you and Tripp have another guy in mind?" Cathy asked.

"That's what I wanted to ask you. Would you and your strap on be the other "guy? You don't have to do anything with Tripp unless both of you want to."

"I'm guessing Tripp gets your ass and I get your pussy?" Cathy asked.

"Yes. Tripp is the only guy to ever have my ass and I kinda want to keep it that way," Jackie explained.

"I get that and I'm fine with it. Okay, I'll do it! When?"

"Tomorrow is Saturday so you could spend the night at ours afterwards, if you like."

"I'm assuming Tripp's okay with this?" Cathy asked.

"Completely. He says he knows this is silly but he doesn't expect to get jealous in the least, since he knows we're friends with benefits anyway. Another guy might be harder for him to accept. And he knows I was going to ask you tonight, if I didn't lose my nerve."

Jackie grabbed her phone and texted Tripp - 'tomorrow night?' A few minutes later he texted back a thumbs up emoji. "We're on," Jackie told Cathy. "Come to our place around 5:30 for drinks and dinner and plan to spend the night, if you wish."

"Cool."

The following night the doorbell rang right at 5:30. Jackie told Tripp to answer it and when he did Cathy entered, carrying an overnight bag. When Tripp took it from her, Cathy hugged him and gave him a chaste kiss on the lips. "Don't worry, Tripp, I asked Jackie first and she said she's fine with it. We are all going to be naked soon, you know!"

Moving into the kitchen Cathy greeted Jackie with a much less chaste kiss while Tripp poured two glasses of Pinot Blanc for the women and a Johnny Walker Red for himself.

"Dinner will be ready in about 30. Why don't we relax in the living room until then," Jackie said.

Once seated comfortably, Cathy asked, "So Tripp, how are you feeling about this now that it's about to move from hypothetical to actual?"

"To be honest, Cathy, nearly every time Jacks spends the night with you, I beat off thinking about what you two must be doing. I've no idea why but the thought of women having sex together is a huge turn on for probably every straight man in the world!" All three broke out in fits of laughter while acknowledging the likely truth to Tripp's admissions.

Jackie excused herself to return to the kitchen. Turning on the burner under a sauté pan, she pulled the zucchini she'd spiralized earlier from the fridge. While she waited for the olive oil to heat up she checked on the grilled shrimp she kept warming in the oven. Tossing the zoodles in the sauté pan she heated up the alfredo sauce in the pot on the back burner.

Once the zoodles were heated through she divided them among the three plates waiting on the kitchen island. After topping these with the shrimp she ladled sauce on each. "Dinner's ready!" she called out. Tripp and Cathy came in and he grabbed the wine bottle from the fridge and topped up his scotch before they all grabbed a plate and moved to the dining room.

"Parmesan, anyone?" Jackie asked as she lifted the tureen and offered it first to their guest. Cathy sprinkled some on her meal and passed the cheese to Tripp who followed suit before handing it to Jackie. "I thought we'd do well with protein and carbs from something light. Don't want any bloated bellies, now, do we?" she asked rhetorically.

When they had finished dinner they put everything in the dishwasher and, taking the wine with them, walked to the guest bedroom. Tripp had turned down the bed earlier when he had moved Cathy's overnight bag there. Jackie stood in front of Cathy and began undressing her, raising her silk cami over her head and tossing it onto a nearby chair.

Jackie moved behind her and, reaching around her waist unbuttoned her shorts and pulled down the zipper. One hand on each hip she pushed them down over her hips and ass until, once they reached her thighs, they

succumbed to the force of gravity and fell to Cathy's ankles. Cathy lifted one foot out and then used the other leg to flip them across the room. She stood across from Tripp in only her lacy red panties and matching bra.

"Beautiful," he said. "Simply beautiful."

With a wink to him, Jackie unhooked Cathy's bra and slipped it off. "I think a couple of you are way overdressed," Cathy stated as she turned to face Jackie behind her. Jackie was wearing a pretty, yellow sundress that Cathy easily lifted over her head and off her arms. Jackie, with smaller breasts than Cathy, was braless, left only in her skimpy white panties.

"One down, or soon to be, and one to go!" Cathy grinned. She and Jackie walked over to Tripp and as Jackie unbuttoned his shirt Cathy unbuckled his belt, open the button and pulled down his fly. "I've heard about what you have here, now it's time to see it!"

With his shirt off the two women pulled his pants down and had him raise first one then the other foot to get them all the way off. The bulge in his boxer briefs seemed to threaten their seams. The women stepped back and the three faced each other in a triangle. "It's time for the reveal. All together now!" Jackie said as she put her fingertips inside the waistband of her panties and waited for the others to do the same.

In unison, each pushed their last remaining article of clothing to the floor and stepped out of them. Tripp's six and a half inch long cock jutted out from his balls at an angle. He was shaved completely bare, shaft, sac, and abdomen up to his navel. Jackie's labia were waxed completely bare, with a neatly trimmed pubic hair triangle which pointed to and stopped just above her clit. Cathy was similarly waxed but above her clit was a landing strip.

"Very nice," Cathy said, referring to Tripp's cock. Looking at Jackie she asked, "May I touch?"

"Of course, hon. Explore!" Jackie replied.

Cathy reached out and took Tripp's cock in her hand. She cupped her fingers over the shaft with the head nestled in her palm and stroked. Then she wrapped her hand around his shaft and pumped it up and down a few times. Finally she reached down, hefted his sac and cupped each ball individually. "I stand corrected...beyond nice!"

Cathy opened her bag and withdrew her strap on and a tube of lube. She stepped into the device and adjusted the clasp at the top of her butt crack. Reaching back into the bag she revealed a small remote control. "The strap on has a clit vibrator on her side," Jackie explained to Tripp. "The remote lets her control the speed and turn it down or off if she's getting too much stimulation."

"This is your fantasy, Jacks, so how would you like to begin?" Tripp asked.

"Spitroast me. On my hands and knees, crossways on the bed. Cathy taking my pussy from behind while I suck your cock, hon," she answered. "And we're going all the way, hon. I want you to cum in my mouth."

They got into position, Cathy standing at the side of the bed, Tripp kneeling in front of Jackie's face. "We're not going to need any lube for this part at least!" Cathy said after plunging her fingers into Jackie's sopping wet pussy.

"Enter me together, please," Jackie requested.

Tripp and Cathy looked at each other and as she started to push the dildo into her pussy she nodded and Tripp put the head of his cock between his wife's other set of lips. The dildo was a bit thicker but exactly the same length as his cock. By keeping their eyes locked together they were able to impale Jackie on both ends at the same time.

Jackie had learned to deep throat Tripp and soon her lips met his base and her chin caressed his sac. On the other end she could feel the top of Cathy's thighs against her ass cheeks, as she too was fully inside. Tripp nodded this time and the two began to pull out, slowly but not fully. Each stopped, Tripp when just his head remained inside and Cathy when all but the head of the dildo had come out.

They continued to stroke in and out of each end, slowly speeding up at Tripp's direction. Cathy realized that her dildo didn't care what speed it moved at but Tripp's cock and Jackie's pussy did. Jackie was already moaning, as best she could with a cock in her mouth, even before Cathy reached around and took her clit with her thumb and fingers.

Jackie shuddered and pressed herself back against Cathy, forcing the dildo deep inside herself as she moaned louder and louder. This, and the vibrator, brought on Cathy's second orgasm as Jackie felt her third well up inside her.

"I'm not going to last much longer, babe," Tripp said.

"Mmmm hmmmm," Jackie mumbled around his cock. She had felt it swell even larger and the vein throb, signs she'd long ago learned meant an eruption was imminent.

Tripp took the back of her head in his hands and sped up his stroking until he could hold off no longer. As that indescribably fantastic sensation began to build to a crescendo, he thrust fully inside to let go. But Jackie had other ideas and fought, successfully, against his grip to move partially off his cock. When he did cum she took it in her mouth rather than directly down her throat.

Jackie let Tripp once again have control but he had no interest in any movement, the overly sensitive head of his cock unwilling to take any more stimulation.

Cathy pulled the dildo out of Jackie's pussy, knelt down and licked her slit and hole before wrapping her lips around the clit and flicking her tongue back and forth across it. Jackie had her most powerful orgasm and sucked fiercely on Tripp's head, now thankfully past the painful sensitivity stage. She came into Cathy's mouth and then pulled off Tripp's cock and collapsed on the bed. Cathy and Tripp each sat crosslegged next to her.

Once she caught her breath, Jackie sat up and opened her mouth. Showing his cum first to Tripp and then to Cathy, she leaned over to the latter and pressed their lips together. She gave her a snowball, pushing about half his load into Cathy's mouth. When they broke off the kiss both faced Tripp, opened their mouths to show him, then swallowed and showed him again.

"That was fucking hot with a capital H O T!" he exclaimed. "Damn, one blowjob and two women swallowing my cum!"

"Was the spitroast what you had expected and wanted, hon?"

"It was everything I had hoped for and more! Did I catch you off guard with my improvised ending, Cathy?" she replied. "I hadn't planned that but when I felt and tasted his load I knew I had to share."

"I enjoyed it, sweetie. It's been a long time since I've swallowed male cum. And I loved the way your's tasted, Tripp," Cathy said.

They relaxed and sipped their drinks as they waited for Tripp to recover for round two. "If it's okay with both of you, I'd be happy to see if I can speed up the recovery process. I'm told I have certain oral talents," Cathy proposed to the couple.

Tripp looked at Jackie and said, "That's your call, hon. No man in his right mind would turn down a free blowjob from a gorgeous woman!"

Jackie laughed. "You've been sharing me with Cathy since before we got married. Only fair that I share you with her, if she wants."

At that, Cathy laid her head on Tripp's stomach and took his mostly soft cock into her mouth. She began by literally sucking, squeezing her cheeks together around him in a kissing kind of motion. Then she added stroking in and out to the sucking, and on the out strokes she fucked his urethra with the tip of her tongue. In no time at all she had to ease off, not being as skilled at deep throat as Jackie. "That should do nicely," she said. "Now how do you want to do the double deed?"

"Here's what I want to try. We'll have to see how it works. Cath, you lie on your back and I straddle your hips. Tripp, you get behind me and take my ass. Once you're fully in my ass, we'll raise up and I'll mount Cathy's dildo, cowgirl style. Sound good?"

Both nodded and Tripp asked, "Once we get started, do we stroke together or opposite?"

"Good question, hon. I don't know right now - this is kinda new for me, you know. I'm going to say opposite for starters - as one goes in, the other pulls out. But I reserve the right to change my mind once we get into it," Jackie said. "I do need some lube on my ass, though."

Cathy passed Tripp the tube of lube she'd pulled out of her bag earlier. Taking it, he lubed his fingers and, with an extra glob on the end for her anus, he massaged her there before inserting two fingers inside her. Stroking them in and out, he brought forth deep, loud moans from her as his motions were rewarded with the relaxation of her sphincter muscles. He knew from their past bouts of anal that this was the sign she was ready for more.

Taking another generous glob of lube he liberally applied it to the head and shaft of his cock. Raising up on his knees he placed the head on her anus. When she muttered 'Yes', he pressed in until the head popped past her muscle and then stopped.

Jackie deliberately relaxed her ass, and in fact her entire body. Once she was accustomed to the invader in her back side she signaled Tripp to proceed and he slowly pushed further. The first couple of times they'd done this, she had to make him stop halfway in. But now she was able to let him go all the way. When he had his full length inside her ass, Tripp stopped.

"Lift up, hon. I want Cathy's cock in my pussy now," Jackie instructed.

Tripp lifted both himself and Jackie's hips up and, once she was high enough, Cathy grabbed her dildo and raised it into position. Jackie felt the head at her entrance and tapped Tripp's leg to let him know to ease them down. In moments her inner thighs were tight against Cathy's outer thighs, the dildo was fully inside her pussy, and Tripp's cock deep in her ass.

"Oh my god! Anal always makes me feel 'full' but this takes that to a whole new level!" she declared.

"Well I know what you mean about full," Cathy said, but I've never done DP so I can only imagine!"

"Tripp, pull out, but leave your head inside. Once you get there, push back in. Cathy, when he starts pushing back in, I'm going to lift off you. And by the way, why are your hands doing nothing when there are two nice little titties with rock hard nipples all alone up here?"

They soon settled into a smooth and comfortable rhythm and both Jackie and Cathy began to cum every few minutes, Cathy's fingering of Jackie's breasts and nipples helping her along while imagining what Jackie must be feeling in her ass and pussy triggering her own.

"Damn that's good! Okay, now I'm switching up. Tripp, I'm going to fuck my pussy in synch with you fucking my ass. So when you get all the way in this time, stop and let me do the same. Then we can resume stroking."

"Okay, hon, but I don't know how much longer I can last. Your ass alone is always incredible but feeling that silicon dick rubbing against my cock through your membranes is almost too much," he informed her.

"Oh wow! This is different. It's like empty, full, empty, full. In some strange way both feel great!," Jackie shared with her lovers as they continued.

"This is it, ladies!" Tripp announced as he slammed his cock deep inside Jackie's ass and came for the second time this evening. When he stopped spurting he lay still, trying to catch his breath and feeling the sweat on his chest mingle with that on Jackie's back. He was certain Cathy, too, must be coated in a sheen of perspiration.

As his cock deflated and shrank, Jackie's ass expelled it. They disentangled from one another and Cathy removed her strap on. Tripp got up and, walking to the master bedroom, turned on the shower and adjusted the temperature. This was the only one in the house large enough for all three of them.

Back in the guest room, both women were still laying quietly on the bed, clearly exhausted. Tripp first kissed Cathy, sweetly but with full tongue action this time. He then kissed Jackie, passionately. "Thank you both, ladies. This was clearly the penultimate sexual experience of my life!" Taking each of them by the hand he led them to the master bath and into the shower.

Since she had been the center of attention thus far, Jackie felt she had an obligation to the others. With the body wash and loofah she tenderly washed every inch of their bodies, alternating from one to the other so neither would be neglected for long. When she finished they returned the favor and then shut off the water and stepped out. Tripp wrapped them all in large fluffy bath towels and they dried off.

"A nightcap, ladies?" Tripp asked. When they both nodded he dropped his towel to the floor and headed to the kitchen, fully naked. Cathy raised an eyebrow so he said, "We're clean and dry. After what we've just been doing getting dressed at this point seems a bit disingenuous."

After another glass of wine for the women and a scotch for Tripp, they moved into the master bedroom, the guest room being in desperate need of a sheet change. "You get the middle, Tripp. Odd genitals out," Jackie smirked.

When Tripp was settled in the middle of the king size bed Cathy slipped in beside him on the right while Jackie took the left side. In mere minutes all three were sound asleep.

When he awoke the next morning, Tripp was still on his back. He felt breasts pressed against him on both sides. One hand, Cathy's he thought, was holding his cock while another was cupping his balls Damn, he thought to himself, I could get used to this!