Trying Something New Pt. 04

**WARNING** Similar to the last chapter, this story involves a lot of male/male intercourse. It also involves some light watersports (urine) play. If those things offend you, you might want to seek out a different story.

***

Darren was even more excited this time when he approached the house of his best friend, Josh, wearing jeans and a red Christmas sweater. Last time he had gotten to experience having sex with Josh as well as Josh's beautiful wife, Tiffany.

This evening, however, things were going to be turned up a notch. Josh and Tiffany were hosting a small Christmas party, and they made it very clear that it was the kind of party that would be naughty and perverted, with plenty of sexual activity.

Darren and Josh's homosexual friend, Jeff, had been invited to join them, which meant that gay sex was a guarantee. Most exciting to Darren, however, was that Tiffany had invited one of her girl friends to the party as well, with the primary intention being to see if she and Darren might hit it off.

As Darren reached the front door, he realized he didn't need to knock or ring the doorbell. Instead there was a note taped to the door that read "CUM INSIDE". With a smile, he turned the doorknob and walked into the house.

He made his way to the living room where he saw Josh in some Christmas pajama bottoms and a white shirt, adding some ornaments to their tree.

"Hey, dude." Josh said, waiving at his friend. "I'm almost done with these. Tiffany is in the kitchen making eggnog, or we have beer too. And I rolled up plenty of joints if you feel like sparking one up."

"Awesome!" Darren replied.

Darren left Josh to finish with the tree and made his way to the kitchen. He was shocked to find Tiffany in a very risque outfit: matching green bra and panties and black thigh-high stockings. The panties had the word "Naughty" written across her rear end in white lettering.

"Fuck, you look amazing." He told her.

"Thanks, cocksucker!" Tiffany teased. "I told you we'd all be getting nasty tonight. Besides, you've already had sex with both of my holes, so no point in me dressing modestly. Might as well flaunt my body, right?"

"Absolutely!" Darren agreed. "Always nice to see you and that body in just your underwear."

Tiffany giggled, appreciating the compliment, as she stirred a large bowl of eggnog.

"Speaking of my underwear..." Tiffany said. "... did you bring my dirty panties back?"

"I did!"

Darren reached into his back pocket and pulled out Tiffany's dirty, white panties she had given to him last time. He reached out and handed them to her. Tiffany stopped stirring so that she could take a closer look at the underwear.

"I guess you enjoyed these." Tiffany noted. "I'm seeing a ton of cum stains."

"For sure." Darren confirmed. "I didn't keep track, but I must've blown at least five or six loads into them."

"I see. Maybe you should be the one wearing these 'Naughty' Christmas panties instead of me." Tiffany said with another giggle. "But seriously, I'm glad you enjoyed them. And a deal is a deal, so remind me to grab you a different pair of my dirty undies before you leave."

"Oh I'll make sure of that."

Darren noticed there was an assortment of Christmas cookies along with the eggnog. As Josh had told him, there was a plate next to the cookies with plenty of freshly rolled joints.

"Are you excited to meet my friend?" Tiffang asked.

"Very." Darren answered. "You said her name is Deidra, right?"

"That's right." Tiffany confirmed. "She's 35, so a few years older than I am. She is slightly bigger than me, but still in great shape and super sexy. It's mostly that she has a bigger butt, which I know you'll like. And her tits are 34C, so also slightly bigger than mine."

"Sounds great to me."

"I also think Deidra is probably one of my more sexually open-minded friends." Tiffany explained. "She was a little skeptical when I asked her if she liked watching gay porn and boys having sex with each other. But then I told her about you and Josh, and the stuff you guys did with Jeff, and she got really interested and turned on."

"Awesome!"

"I think what convinced her to come to this party, though, was showing her those gay pictures you guys took together." Tiffany added. "She really enjoyed looking at them."

"She sounds like a fascinating woman." Darren said. "I can't wait to meet her."

"And if you're wondering, she has a great snatch." Tiffany told him. "I've had the pleasure of tasting it a few times. And likewise, she's gone down on me and I can confirm Deidra knows how to use her mouth and tongue."

Darren was very much becoming aroused, seeing Tiffany in her sexy underwear and talking about her friend and naughty things in general.

"Maybe I'll get to see you ladies each eat other out tonight?" Darren asked. "That'd be pretty hot."

"It's certainly possible." Tiffany said. "But you know I expect you boys to put on a good show for us, and I'll bet Deidra is hoping for the same."

"Just like last time, I'll take all the cock you want me to if it means I get to see you naked." Darren told her. "And now I'll be even more motivated since I'll want to explore Deidra's body too."

"There's the horny cocksucker I know!" Tiffany said with a grin. "I can't wait for you and Deidra to meet. I really hope it works out. I think she's going to enjoy seeing how good you are at sucking a cock."

"Do I hear you two talking about sucking dick again?" Josh asked, walking into the kitchen and giving his wife a smack on the rear.

"Yep!" Tiffany replied. "We were talking about my friend, Deidra. And that just kind of naturally led us down the road of me telling Darren that he would need to make sure to put on a hot show with you and Jeff."

"Didn't we earn your trust last time, babe?" Josh asked, grabbing one of the joints as well as a nearby lighter. "I don't recall us refusing to do any of the dirty sex acts you demanded."

"That's true." Tiffany admitted. She then turned to Darren. "Sorry I doubted your willingness to suck dick and have nasty, gay buttsex in front of me and my friend."

Josh sparked the lighter and started to light the joint as Darren responded to his best friend's wife.

"That's okay, Tiffany. I get it." Darren told her. "But you saw how much I enjoyed Josh's cock last time. I took it up the ass right in front of you. There is no doubt you'll be treated to plenty of guy on guy action."

Josh took a puff from the joint and passed it to Darren.

"That's fair. I'm not sure why I was so worried." Tiffany added. "I think part of it is that I'm horny, and I'm ready to see you guys fucking some more. But then part of me also wants to impress Deidra and make sure she has fun at our sex party."

Having taken his turn, Darren passed the joint to Tiffany.

"Your outfit is already turning me on." Darren told her. "I can't wait for the others to arrive so we can really start this party."

Tiffany exhaled a large plume of smoke as she returned the joint to Josh.

"Remember what we talked about last time." Tiffany said. "The first place that penis is going is right up my husband's ass!"

Darren grinned and looked at his best friend, who simply shrugged.

"She's the boss!" Josh joked as he took a drag off of the joint.

As the three of them continued to enjoy getting high and discussing naughty possibilities of the night, they were joined by the other guests.

Jeff was dressed in a festive Santa outfit, complete with the red hat. Deidra came wearing a tight pair of jeans that hugged her luscious buttocks. She also wore a black top that showed off plenty of cleavage.

While Jeff, Josh, and Tiffany indulged in another joint, Darren and Deidra each got a cup of eggnog and started to get to know each other in a side conversation. Darren couldn't help himself from eyeing Deidra's ample cleavage often. She didn't seem to mind at all.

"You look really beautiful." Darren said.

"Thank you. It's nice to finally meet you." Deidra replied. "Tiffany has been telling me a lot about you."

"Knowing her, she's probably been giving you some details about my sex life."

"Of course she has." Deidra confirmed with a giggle. "But I like that. I mean, she told me she was hosting a sex party. That's kind of kinky for a first date, don't you think? You sound like my kind of guy."

Darren's heart was pounding as he took a sip of his eggnog.

"I can be pretty kinky, I guess." Darren said. "When the mood hits."

"So I've been told." Deidra quipped, smiling. "No need to be bashful around me, Darren. I fully expect to have sex with you tonight. I also fully expect to see you sucking a dick, or taking some cock, as well as other dirty fun. I want to get to know the real you, so don't feel apprehensive at all."

"Wow. I love how blunt you are. It's quite refreshing, and also a turn on."

"I might be getting a little wet myself." Deidra added, winking at him and taking a sip of her eggnog. "I consider myself bisexual just like you. I love sex. Pussy, cock ... I don't care. My only rule is that I won't date or fuck someone who is only going to offer a vanilla sexual experience."

Deidra suddenly reached out and put her hand on the crotch of Darren's jeans. She smiled when she felt his bulge.

"You weren't kidding. Your penis is already hard." Deidra said. "I'd love to see it."

"You want me to show you my dick?"

"That's right. It's a sex party, right?" Deidra teased. "I'll get naked if you take off your pants. Show me yours, I'll show you mine."

Darren was blown away by Deidra's personality and sexual energy. He took another sip of his eggnog and then sat his glass down. He unzipped his jeans and pushed them down along with his boxers. He stepped out of them and was now wearing only his Christmas sweater. As he faced her, his erect penis was on full display.

Deidra reached out again, this time feeling and holding Darren's manhood in her hand.

"Not bad at all." She told him, softly squeezing his firm dick. "I could definitely put this thing to good use."

As Deidra played with his shaft, Darren reached out and gave one of her tits a squeeze through her top. Darren looked over and noticed Tiffany glaring at him, hands on her hips.

"What's going on over there?" Tiffany asked.

"Just getting to know each other." Darren joked.

"I thought I was clear about where that cock was going." Tiffany snapped. "Was I not clear?"

"You were." Darren admitted. "It's going in Josh's ass first."

"Exactly." Tiffany said with a grin. "If you're so horny, I take that as meaning you're ready to buttfuck my husband."

"To be fair, I did offer to get naked if he showed me his dick." Deidra explained to Tiffany.

"You can get naked and have sex with him all you like." Tiffany replied. "Just as soon as he's done plowing Josh's rear."

Deidra let go of Darren's throbbing penis and smiled at him.

"Sorry I got you in trouble." She said.

"Totally worth it to have you play with my dick, even if briefly." Darren told her. "I'm glad you like it. I'll show it to you again after I finish having sex with Josh."

"Deal."

The five of them made their way to the living room, ready to commence the night of perverted debauchery. Josh wasted no time removing all of his clothes and revealing his own erection to his wife and their guests.

"Yummy!" Jeff snickered as he stared at Josh's thick penis. "I can't wait to play with that beautiful piece of meat."

Although she didn't get completely nude, Deidra got on Tiffany's level by stripping down to her underwear. With no bra, Deidra wore only a black thong as she took a seat on the couch.

Tiffany also discarded her bra, leaving her in just the green panties and black thigh-highs. She then sat on the couch next to her friend.

"Okay, boys. My husband is nude." Tiffany said. "Time to slide that penis in his ass, Darren!"

Josh happily got onto all fours in front of the couch, making sure the ladies would have a good angle to watch him being assfucked. Darren, still wearing just his sweater, knelt down behind his friend and started to playfully rub his manhood on Josh's exposed buttocks.

"This is so exciting!" Deidra chimed in. "It's like we're watching a live action gay porn."

Darren held one of Josh's cheeks open, aiming the head of his penis directly at his best friend's waiting asshole.

"Ready, dude?" Darren asked.

"Hell yeah." Josh answered. "Give me that cock!"

Darren obliged, easing the tip of his cock into Josh's anus. Josh moaned as he felt Darren begin to probe his backside.

"That's a good boy!" Tiffany hissed. "Fuck my husband just like he fucked you last time. I want to see every single inch shoved in there."

Again Darren obliged, sliding more of his dick into Josh's rectum.

"This is so fucking hot!" Deidra exclaimed.

"It really is." Tiffany agreed. "But I feel like something is missing."

"Maybe your husband should have a penis in his mouth, too?" Deidra suggested.

"Absolutely!" Tiffany told her friend. She then looked over at Jeff. "Jeff, would you be a doll and put your dick in my husband's mouth please?"

"It would be my pleasure." Jeff replied. "He's given me hundreds of blowjobs over the years, so I know he knows how to suck."

Jeff quickly discarded his Santa outfit, showing off all seven and a half inches of his penis. He kept the hat on his head however, as he approached Josh's face.

"Look, honey!" Tiffany said. "Santa brought you a cock for Christmas!"

Jeff's manhood waved around in front of Josh's face. Josh instinctively opened his mouth to receive his gift, but Jeff delayed his gratification by playfully smacking Josh's face with his penis.

"Cock slapping is so underrated." Deidra commented. "When I'm horny and about to have sex I absolutely love feeling a hard dick slap me right in the face like I'm just a desperate, helpless whore."

"I agree." Tiffany added. "Right up there with dick spankings on my bare ass or my wet cunt."

Jeff gave Josh one more slap on the face with his penis before inserting it into his mouth. Meanwhile, Darren had found a steady pace of sliding his erection back and forth between Josh's buns, in and out of his tight manhole.

"This is much better." Deidra said. "Seeing your husband taking it from both ends."

"For sure." Tiffany agreed. "Look how easily he's taking Darren's cock. You can tell he's had a lot of dick in there."

Darren gave Josh's bare ass a smack as he continued to fuck him. Josh held the base of Jeff's shaft as he licked and sucked the horny penis.

Darren looked over at the couch and was happy to see that both girls had a hand between their legs, rubbing themselves through their underwear as they watched the show.

"Keep fucking that ass!" Tiffany demanded.

"Yeah! Stuff that hungry butthole!" Deidra offered. "You guys keep those hard dicks in both of his holes!"

Josh continued to take Darren's penis in his ass while he joyfully sucked up and down Jeff's throbbing cock. Jeff held the back of Josh's head, providing assistance for the blowjob.

Tiffany and Deidra were really rubbing themselves at this point, close to climaxing as they observed the gay threesome.

"I'm about to bust a nut in your ass, dude." Darren announced.

"Yeah I'm pretty close myself." Jeff added. "I'm gonna fill your mouth with my sperm here in a second."

The girls giggled with delight in anticipation of watching Josh being filled with semen. They also started breathing heavier as they got closer to their own orgasms.

Darren slammed his manhood deep into Josh's backside. He held it all the way inside as he began to ejaculate. Not to be outdone, Jeff arched his back and started to unload in Josh's mouth.

"They're cumming!" Deidra said excitedly. "They're cumming inside of your husband!"

"Hell yeah they are." Tiffany hissed. "Give him every last drop, boys. Breed my husband!"

Josh easily sucked down every bit of Jeff's load as his rectum accommodated Darren's fresh donation of spunk. The girls moaned, climaxing into their respective panties as the all-male threesome wrapped up.

Jeff allowed Josh to slip the cock out of his mouth as Darren retracted his penis from Josh's creampied fuckhole. Josh took a moment to compose himself before getting to his feet, his own thick cock throbbing and dripping.

"Where do I get to shoot my load?" He asked.

"You can shoot it on me." Darren answered quickly. "Jerk off and cum on my dick, and then Jeff can lick me clean."

Everyone seemed impressed by Darren's quick thinking.

"Wow, Darren." Tiffany said. "Look at you jumping right into the driver's seat and taking the lead on finding a gay solution!"

"I just thought you ladies wanted a good show." Darren told her, before winking at Deidra.

Jeff remained on his knees as Josh stood facing Darren, his erection pointed at Darren's crotch. Josh took his shaft in his hand and began to stroke it. It only took a few strokes to reach orgasm, as multiple ropes of sticky cum hit Darren's pubic area. Josh then wiped the final streak from his urethra along his best friend's now-flaccid dick.

"Now move, honey." Tiffany demanded. "Make room so that Jeff can lick your cum and your ass juice off of Darren's cock!"

Josh moved aside so that Jeff had room to crawl over to Darren on his knees. Darren pulled off his sweater and tossed it aside. Jeff didn't need to be told what to do, sucking the cum blobs from Darren's pubic hair. He then slowly and tenderly cleaned off Darren's penis with his tongue.

Satisfied with his work, Jeff gave Darren's soft cock a kiss and then got to his knees.

"That was amazing." Deidra said. "Tiffany wasn't kidding. You guys really know how to fuck each other!"

"Josh and I have had over a decade of practice." Jeff bragged with a grin. "And Darren is really making up for lost time lately. He's a natural."

Darren blushed at the compliment from his homosexual friend, especially with Deidra hearing firsthand that he was talented at having sex with other men. He was eager to impress her, and her orgasm while watching him make love to Josh was a great start.

"I can't wait to see what's next." Deidra said. "But first I need the bathroom. My bladder is about to burst."

"Want some company?" Darren offered.

"In the bathroom?" Deidra replied with a smirk. "Are you wanting to watch me while I pee, Darren?"

"Yes please."

"Kinky." Deidra added. "I like it. But I guess I won't be needing my underwear anytime soon."

Deidra stood up from the couch and pulled down her soiled thong, stepping out of it and casually tossing it onto the coffee table. She then sauntered down the hall and to the guest bathroom, with Darren following behind and staring at her bouncing ass cheeks.

Once in the bathroom, Deidra plopped down onto the toilet seat, giving Darren a clear view between her legs.

"You have a beautiful vagina."

"Thank you!" Deidra said. "Why don't you get down here and get a better look at it?"

Darren smiled as he accepted the lewd invitation, kneeling in front of the toilet and admiring the lovely pink hue of her exposed cunt. He was close enough that he could smell her feminine scent, and it was making him excited.

"Here it comes!" Deidra gleefully announced.

Darren watched as she began to relieve herself, openly urinating in front of him. He was mesmerized by the sight of her golden stream.

"Have you always been into watersports?" Deidra asked. "Watching people pee?"

"I stumbled across it while watching some lesbian porn a few years ago. It turns me on, but this is the first time I've ever experienced it in person." Darren explained. "Watching you now, this is way hotter than any of the videos I've seen."

"That's so sweet."

Darren continued to admire Deidra's steady stream of urine, watching as it slowed to a trickle. Then one last gasp of a squirt, and finally just a few droplets. She started to reach for the toilet paper, but Darren stopped her.