Trying Something New Pt. 06

"So you made it there okay?" Darren said into his phone.

"Yep. I got here about ten minutes ago." Deidra replied from the other end. "Just getting settled into my brother's room and changing clothes. I'm actually just standing here in my panties at the moment."

Darren felt a twitch in his manhood as he pictured his girlfriend in nothing but her underwear.

"I'm surprised your brother didn't fuck you immediately."

"Brad is currently making us some cocktails." She explained. "I'm just trying to pick out something sexy to wear that'll make his dick hard."

"Sounds like you're already wearing the perfect outfit." Darren told her. "Just a pair of panties. Tits out and swinging freely. I wouldn't be able to stop myself from sucking your nipples and groping that incredible ass of yours."

Deidra giggled, appreciative of the compliments.

"Speaking of being in my underwear..." Deidra said. "... are you wearing those sexy red panties I gave you?"

"Not quite." Darren answered. "But don't be mad. I actually went out and bought a variety for myself."

"Oh good! That makes me so happy to hear. So what type of underwear do you have on?"

"I'm currently enjoying a purple, satin bikini. Pretty comfy."

"That sounds sexy!" Deidra exclaimed. "I bet they look great on you."

"If you were here, I'd he happy to model them for you."

"If I were there, I'd likely be fucking your ass with my dildo again." Deidra said with a laugh. "Which reminds me... I appreciate how supportive you've been of my... special... relationship with my brother."

"Of course! I remember how you described his penis. I'm happy you get to spend a few days enjoying it." Darren assured her. "I hope I'll get to enjoy it myself one day."

"I hope so too." She added. "But I really do appreciate you letting me spend time having sex with Brad, and I don't want you to be lonely while I'm gone. You should get to have some fun, too."

"What do you mean?"

"I set you up on a date with a really good friend of mine. Her name is Krystal." Deidra explained. "And before you ask, yes I've fooled around with her off and on for several years. I know she will take very good care of you."

"You mean..."

"Sexually. I asked her to keep you company and I think you're going to really like her."

"You set me up to have sex with one of your friends. Are you the most incredible girlfriend ever?"

Deidra giggled again.

"Probably." She joked. "You should also know that I talk to her about everything. I've told her about you... about us."

"Everything?"

"Everything." Deidra confirmed. "She knows about you having sex with Jeff and Josh. She knows I pegged you with my strap-on. She even knows you enjoyed wearing my panties the other day. She's cool with all of it."

"Wow." Darren said, feeling both aroused and also a little embarassed. "You weren't kidding about telling her everything."

"Don't be shy, baby." Deidra told him. "She's even more of a free spirit than we are. She was genuinely excited when I asked if she would look after you and your needs. And if it makes you feel better, Krystal is obsessed with all things anal. That girl loves having a stiff cock up her ass."

Hearing this brought Darren back to predominantly feeling aroused.

"Krystal sounds like a very nice girl."

"I knew you'd feel more comfortable if I told you some quality buttfucking was on the table." Deidra cackled. "I told her you'd meet her at the bar for drinks tonight at 6. But I just have one request."

"What's that?"

"I want you to call me after you two have sex." Deidra said. "I know you're going to love it and I want you to tell me I was right. Deal?"

"Deal."

"Good, because I just found the perfect thing to wear." Deidra added. "Lace, crotchless panties and one of my skimpy nightgowns. That should let me flash my brother my cunt and ass quite a bit. Have fun on your date, honey."

"Thank you, darling." Darren replied. "Have fun riding your brother's big cock!"

They both hung up. Darren looked at his watch and realized that he should probably get ready so he could be on time to meet Krystal.

***

Darren arrived at the bar wearing a nice pair of jeans and a black button-up shirt. He looked around and then noticed a stunning brunette standing at the bar.

She was wearing a tight, black miniskirt that allowed her to show off her incredible backside. She also had on a low-cut, red top which left everyone with a great view of her ample cleavage. Darren cleared his throat and made his approach.

"Krystal?"

The woman turned with a big smile.

"You must be Darren!"

They embraced in a quick hug. Darren couldn't help but glance down at Krystal's spectacular breasts. They looked too perfect to be natural, but Darren didn't mind. They ordered drinks, Krystal opting for a cosmopolitan and Darren settling for a beer.

For a while they made casual small talk until Darren decided to address the elephant in the room.

"From what Deidra told me earlier, it sounds like you know everything about our sex life. And also mine." He said.

"She's told me quite a bit." Krystal confirmed. "Does that embarass you?"

"A little bit. But she said you didn't have a problem with it."

"No problem at all. I think it's hot." Krystal said, winking at him. "I prefer having sex with open-minded and kinky people. Life is too short for boring, vanilla sex."

Darren nodded in agreement as he took a sip of beer.

"I think it's really cute that you like to suck dick." Krystal continued bluntly. "And get fucked in the ass. And I got especially excited when Deidra told me how much you enjoyed wearing her panties."

Darren chuckled as he blushed.

"To be fair, I also enjoy getting kinky with the ladies." He said. "I love eating assholes, for instance. Really getting my tongue in there nice and deep. And I hope you don't mind me saying so, but your ass looks superb in that skirt."

"Thank you!" Krystal told him. "I might just have to use it to sit on your face later. See what that tongue of yours can do."

Darren felt himself twitch as he considered Krystal lowering her bare ass onto his face.

"You're welcome to sit that beautiful thing on my face any time you like!"

Krystal giggled and they each took a sip of their drinks.

"So what else has Deidra told you?" Darren asked. "Do you know why she's out of town?"

"Oh... you mean at her brother's house? Yes, I'm well aware of their special bond." Krystal said with a grin. "In fact, I bet his penis is inside of her right at this very moment."

Darren felt himself twitch again at the possibility Deidra was currently being fucked by her brother's 8.5" cock. The folds of her vagina gripping his penis as it slid in and out of her.

"Did you just picture it? Your girlfriend's cunt full of her brother's dick?" Krystal asked. "Or maybe she's bent over, spreading her cheeks, taking it up the ass. Does thinking about that turn you on?"

"Fuck yes!" Darren exclaimed.

"Do you wish it was you fucking her in the ass?" Krystal continued. "Or maybe you would rather be the one taking her brother's cock in your own ass?"

"I'd love to be in either position." Darren admitted. "If you aren't careful, I'm going to have to go in the bathroom and rub one out."

Krystal giggled again, amused to be teasing Darren and making him hot and bothered.

"That would be such a waste of your cum." Krystal noted. "I think a better idea would be to finish our drinks, go back to your place, get naked, and have a good fuck."

"That sounds like a nice plan." Darren agreed. "But in that case, where would you suggest I shoot my load?"

"You're more than welcome to finish in whichever hole you like." Krystal teased. "You could even squirt it on my tits and lick it off after."

"If I'm going to eat my cum, I'd prefer to eat it from your asshole."

"That can certainly be arranged." Krystal added.

Darren was amazed at how open and brazen Krystal was. His manhood was throbbing at the thought of pumping his sperm into her anus. And then sucking it out of her asshole.

"I guess we should finish off these drinks then." Darren said, raising his glass. "To meeting new people. And to buttsex!"

Krystal raised her glass, joining his cheers, and then they both finished their drinks. Darren paid the bartender and then they made their way back to Darren's place.

***

Once they arrived, Darren poured them each a glass of red wine and they took a seat on the living room couch.

"I couldn't help but notice you brought in a large bag with you." Darren said.

"Deidra was very clear when we spoke. She asked me to keep you company while she's out of town." Krystal explained. "That's why I packed an overnight bag. I hope that doesn't make you uncomfortable."

"Not at all." Darren told her. "I'm just blown away that Deidra convinced such a beautiful woman to spend an evening with me."

"She really cares about you." Krystal added. "She didn't want you to be lonely in her absence. I was happy to offer my services."

Darren could feel his arousal returning as he took a sip of wine. Krystal wasted no time in steering the conversation back in a sexual direction.

"I'm curious about your underwear." She said with a sly smile. "What kind of underwear do you have on?"

Darren blushed but knew there was no point in lying.

"As you well know, I enjoyed wearing Deidra's panties the other night. So I went out and bought some for myself." Darren answered. "I am currently wearing a pair of purple, satin bikini panties under my jeans."

"Mmm. That sounds lovely." Krystal said. "I'd love to get a look at them. If you show me your panties I'll show you my tits."

Darren chuckled and stood up. He unbuttoned and unzipped his jeans, pushing them down and stepping out of them. He then stood there, letting Krystal look him over. Her eyes went right to Darren's bulge.

"They're so pretty!" Krystal complimented. "And it looks like someone's getting a little excited. Those poor panties are trying their best to conceal that bulge."

Darren turned around and wiggled his butt for Krystal. He felt her hand give one of his cheeks a squeeze.

"Look at that booty." Krystal said. "The panties really accentuate your cute little cheeks. I can see why Deidra decided to peg you. That ass is just begging for a stiff dildo or cock!"

Darren felt Krystal give his ass a good slap. He then sat back down beside her. Holding up her end of the bargain, Krystal pulled her top off, freeing her large breasts. They sat perfectly on her chest.

"They're fake." Krystal admitted. "But I like them and most guys don't seem to mind."

"I think they look spectacular." Darren told her, reaching out and taking one of her breasts in his hand. He gave it a squeezed before running a finger over the nipple. "Very nice tits."

"Thanks. I'm glad you like them." Krystal said, reaching over and running her index finger up and down along Darren's bulge. "Your penis is so hard. I love the way it feels through the fabric of your underwear."

They continued to touch each other a bit more, Darren fondling her breasts and Krystal running her finger along his pantied erection.

"I'd love to get a look at your panties." Darren suggested. "That is... if you're wearing any panties."

Krystal smiled back at him.

"Yes, I'm wearing underwear." She confirmed with a giggle. "And I guess you showed me yours so it's only fair to show you mine."

Krystal stood up and turned away from Darren. She reached behind her back and unzipped her skirt. Darren unbuttoned his shirt and took it off as he watched Krystal shimmy out of her skirt. Her bikini panties were a vibrant pink and looked amazing on her round buttocks.

Darren didn't think he could be anymore turned on, but then Krystal turned around. His eyes went wide as he looked between her legs. Instead of the cameltoe he was expecting, he instead saw a prominent, protruding bulge that rivaled his own.

"Oh wow." Darren managed to say. "Deidra left out that little detail."

"My penis?" Krystal asked. "You might be the first person to call it little."

"Oh no, that's not what I meant." Darren said with a laugh. "It doesn't look small at all. I was just saying that Deidra didn't tell me you had a cock!"

"I hope that won't be a problem for you."

"Are you kidding?" Darren asked. "This is like a dream come true."

"Is that so?"

"Absolutely. Ever since I stumbled across trans porn, it's been one of my biggest fantasies to meet a beautiful girl with a big dick." Darren told her. "I can't wait to get a look at you without the panties."

"You're still wearing your underwear." Krystal protested. "If you want to see my penis then I want to see yours."

Darren stood up from the couch and stood in front of Krystal. Their respective bulges were just inches apart.

"It feels like we're in the Old West and about to duel." Darren snickered. "Should we whip 'em out at the same time?"

"That sounds like a good idea to me." Krystal replied.

They both reached into their waistband and readied themselves. After a few more seconds of building anticipation, they both tugged their respective panties down, unveiling the hard, throbbing dick they had previously concealed. Darren was in awe when he saw Krystal's cock.

"I love that yours is bigger." He said.

"I don't know." Krystal replied. "They're about the same size it looks like."

"No way."

Darren took initiative, reaching out and taking her penis in his hand. He stepped toward her and held his erection beside hers in comparison.

"See?" Darren said. "You've got at least a half inch on mine."

Krystal giggled.

"Well, I'm glad you like it." She told him. "That feels nice to have them touching and rubbing together."

"It's a beautiful cock, Krystal." Darren added. "So hard and excited."

"If you love it that much, you should really thank Deidra." Krystal said. "I was seriously considering gender reassignment surgery but Deidra convinced me that it would be a crime against humanity to get rid of my dick."

"She was right." Darren agreed as he rubbed their erections together. "I can't wait to run my tongue up and down your shaft."

"Why wait any longer?"

Krystal pulled her panties the rest of the way down and stepped out of them. Darren did the same. Krystal then took a seat on the edge of the couch with her erect penis pointing to the ceiling.

"Come and get it! Show me what that dirty mouth of yours can do."

Darren knelt down in front of her, his eyes fixed between her thighs. With one hand, he grabbed the base of her cock. He then leaned down and planted a soft kiss on the tip. He continued kissing down her length until his lips arrived at Krystal's plump testicles. Darren didn't hesitate to suck one of her balls into his mouth followed by gently sucking on the other ball. He then ran his tongue back up her erection slowly.

"You really know your way around a cock!" Krystal told him. "I'm impressed."

"I'm still learning." Darren admitted. "But I'm glad you like it."

Darren opened his mouth and slid it halfway down her penis, causing Krystal to moan with pleasure.

"You're doing great, baby." Krystal encouraged. "In my experience, if someone enjoys what they're doing, it's usually a pretty good blowjob."

Darren smiled around Krystal's dick as he took more of it into his mouth. Krystal began to fondle her breasts and pinch her nipples as she was being sucked off. Darren gently started to play with Krystal's testicles as he orally serviced her cock.

"Oh fuck yes." Krystal moaned. "You're going to make me cum, baby. Your mouth feels so good."

Krystal's positive feedback only fueled Darren's lust as he bobbed up and down. He continued to massage her ballsack with one hand and then used his other hand to explore her ass crack, quickly finding her special hole.

Krystal continued breathing heavily and groping her breasts as Darren pleasured her cock and played with her rear entrance.

"Don't stop." Krystal pleaded. "This is incredible!"

Darren could taste precum on his tongue but he wanted much more than just a few droplets of her semen. Darren kept sucking as his finger slid past her sphincter. He pushed his finger deeper until he found Krystal's prostate and began to massage it.

Krystal moaned as her ass muscles squeezed around Darren's probing finger. As Darren's lips slid up her cock, he felt her release. He slid back down Krystal's shaft as warm semen spurted into his mouth.

"Take it! Take it!" Krystal demanded.

Darren obeyed, keeping his mouth wrapped tightly around her penis until every drop was milked out. He then slowly and carefully pulled his mouth off of her, showing her the puddle of cum on his tongue before closing his mouth and swallowing the load.

"That was one amazing blowjob." Krystal panted.

"The pleasure was all mine." Darren assured her, slowly retracting his finger from her ass. "You are delicious."

They smiled at each other, pleased with their initial sexual encounter.

"Now it's my turn. Do you prefer I suck you off?" Krystal asked. "Or would you rather I bend over and let you fuck me in the ass?"

"I mean... if it's an option..." Darren began. "... I'd be honored to fuck that sexy butt!"

"Of course it's an option." Krystal confirmed with a wink. "Deidra told me to take good care of you."

Krystal turned around on the couch, her knees on the cushions. She leaned over the back of the couch, presenting her ass as well as her anus to Darren and offering it to him. Darren got to his feet and stepped toward her, his erection pressing against her rear. Darren enthusiastically started to slide his penis into her waiting hole.

"Mmm. Your ass feels amazing." Darren told her.

"I'm glad you like it, honey buns." Krystal replied as she accepted more of his cock into her asshole. "Hopefully you'll let me return the favor."

Darren's erection throbbed in her rectum as he heard her propose the idea of fucking him.

"You're a beautiful woman, Krystal. Of course I'll bend over and let you fuck my ass raw."

They moaned in unison as Darren continued to slide his manhood between her amazing buns. The sensation as her rectal walls squeezed his length only heightened Darren's arousal. He reached around and took Krystal's cock in his hand as he fucked her.

"That feels so good." Krystal purred.

Darren slowly stroked her penis as he pumped his shaft into her rear. Krystal's ass muscles gripped his erection with each thrust.

"If you're not careful, you're going to make me cum all over this couch." Krystal said.

"Be my guest." Darren told her. "I'm going to cum all over the inside of your ass."

The butt fucking intensified. Darren rammed into Krystal's asshole and stroked her cock faster with his hand. He could feel her penis throbbing and it only fueled his arousal further.

"Tonight my ass belongs to you." Krystal whimpered. "It's all yours."

With a loud moan, Krystal ejaculated, spraying the couch cushions with fresh sperm. Darren followed soon after, injecting his sticky semen deep into Krystal's bowels. He left his penis inserted in her rear until every last drop of cum had been expelled.

"That was amazing!" Darren exclaimed, pulling his dick out of her.

Darren kneeled down and kissed Krystal's stretched, sloppy orifice. He then licked a trickle of cum from her sweaty scrotum before standing back up.

"You're quite the eager lover." Krystal said, getting up from the couch and facing him. "Give me a few minutes to... reload... and then I'll bend you over."

"Take your time." Darren told her. "I need to give Deidra a quick call anyway."

They shared a brief kiss and then Krystal picked up her discarded panties, using them to wipe up some of the excess cum from the couch. Darren retrieved his cell phone and called Deidra.

On the third ring, she answered.

"Hey babe... how's your evening going?" Deidra asked, sounding out of breath.

"My evening has been incredible." He answered. "You sound a little winded."

"Yeah... Brad's currently fucking my pussy."

"Oh, sorry. I didn't mean to interrupt."

"It's fine..." Deidra said. "... so how do you like Krystal? Is she taking good care of you?"

"You were right. Krystal is an amazing woman." Darren replied. "And thank you so much for being in her life."

"You're welcome... but what do you mean exactly?"

"She told me that she considered gender reassignment surgery." Darren added. "She said that you talked her into keeping her penis. So thank you. If you hadn't done that, I never would've gotten to suck on her fantastic dick."

"I'm so... happy to hear it." Deidra panted. "I hope you're doing more than... just sucking on it."

Darren chuckled, looking over at Krystal's naked, feminine body, as well as the lovely penis and testicles between her legs.

"That's the plan." Darren assured his girlfriend. "I just fucked her in the butt, and we both agreed that my ass is next."

"Good." Deidra said. "You and Krystal enjoy yourselves."

"We will." Darren added. "You have fun fucking your brother."

"I already am."

They ended their call and Darren set his phone down. He walked over to Krystal and placed one hand on her bare ass.

"Shall we move this party to the bedroom?"

"Sure. I guess that means you're ready for my cock?" Krystal teased.

"Yes. I'm ready to feel you inside of me." Darren said. "I need your dick. Please."

Darren and Krystal walked to the bedroom together, their naked bodies side by side. Once in the bedroom, Krystal started tugging on her semi-erect penis while Darren applied a healthy dose of lubricant to his ass.

"How do you want me?" Darren asked.

"Missionary." Krystal answered. "I want to look into your eyes while you take my cock in your ass."

"Yes ma'am!"

Darren got into position on the bed and watched Krystal work a handful of lube over her now fully erect penis. Krystal then stepped over to the edge of the bed, positioning her shaft at Darren's vulnerable entrance.

"Ready?"

Darren nodded eagerly. Krystal smiled and started to ease her cock into his ass. Before long, it was one fluid motion of passionate anal sex. They continued fucking until they both erupted with powerful orgasms.

Afterward, they climbed under the covers together, falling asleep naked and satisfied.