Trying Something New Pt. 05

It had been a couple of days since Tiffany's extremely successful holiday sex party, and Darren was excited to see Deidra again as they were now dating. They had each shown off their bisexual skillset and really hit it off. Deidra had enjoyed watching Darren fuck his best friend in the ass as well as taking another friend's cock up his later on in the evening. Likewise, Darren had gotten a kick out of fucking Deidra from behind while she ate Tiffany's pussy.

Darren had invited Deidra over for an after-dinner drink, as well as sex, and Deidra had agreed. Darren was waiting in the living room, making sure his jeans and blue button-up shirt looked nice. That's when he heard the doorbell.

Darren opened the door, welcoming his new girlfriend and sex partner inside. Deidra was wearing a black, low-cut top which highlighted her cleavage. She also had on a black miniskirt that ended at her upper thigh, revealing plenty of her shapely legs. She sat her purse down on the coffee table and turned to Darren, giving him a kiss and handing him a small box that was a little bigger than the palm of his hand.

"Is this for me?" He asked. "You didn't need to get me a present."

"I know. It's just something fun." Deidra said. "I instantly thought of you when I saw it the other day."

Curious, Darren lifted the lid and looked inside. He smiled as he pulled out the gift: a four inch butt plug. But instead of being smooth or beaded, the insertable part was shaped like a penis.

"How cute!" Darren said.

"I thought you might like it." Deidra told him. "And this way, even if your friends aren't available, you can pop that guy in and walk around with a little dick in your ass."

"Such a thoughtful gift." Darren added, kissing her again. "I love it."

"I'm glad! I'm actually wearing a matching one right now, myself." Deidra said with a smile. "And it's just a small gift. I'm sure it pales in comparison to your dildos."

"I actually don't own a dildo. At least not yet."

"What?!" Deidra exclaimed. "You're bisexual and from what I've seen with my own two eyes, you LOVE the cock. You should definitely own a dildo or two."

Darren chuckled at Deidra's reaction.

"I'm not opposed to it." Darren admitted. "Just haven't taken the time to go out and buy one."

"Maybe that should be part of our next date." Deidra suggested. "We could go shopping together and find you the perfect dildo to start your collection."

Darren felt a tingle of excitement at the suggestion, and the idea of browsing a collection of dildos with this beautiful, supportive woman. He tried to bring his focus back to the moment at hand.

"So you said you had a matching plug in your ass?"

"I sure do." Deidra confirmed, smiling again. "I wanted to make sure I was warmed up before coming over. I know how much that tight little hole means to you. Smelling it. Fingering it. Licking it. I just assumed that you'd most likely want to fuck it, too."

"I'd absolutely love to slide my dick into that sweet ass of yours." Darren told her. "Pump every drop of my cum into your bowels. I'll even suck my own cum out of your asshole after I'm done."

They kissed again, giving Darren an opportunity to reach behind her and squeeze her buns through her miniskirt. Deidra squealed in delight as Darren groped at her bottom.

"I thought you invited me over for a drink, too?" Deidra asked. "Or are we going to just skip right to getting naked and having sex?"

"I'm good with just skipping to sex." Darren joked.

They laughed and now Deidra gave Darren a playful smack on the rear.

"Wine okay?" Darren asked.

"Wine sounds great!"

The two of them made their way to the kitchen. Darren grabbed two glasses and a bottle of red wine. Taking out the cork, he filled each glass, sliding one to Deidra. She thanked him and then took a sip.

"Can I ask you something?" Deidra asked. "It's about guys. Or, to be more specific, it's a question about dicks."

"You can ask me anything you like. We're still getting to know each other." Darren said. "What's your question?"

"As far as other guys go, you've only had sex with Josh and Jeff, right?"

"That is correct. So far, they are the only two guys I've been with."

"First of all, I love that you said 'so far', which seems to imply you're open to playing with other cocks down the road." Deidra told him with a giggle. "But back to your friends. At Tiffany's party, I couldn't help but notice that you're all fairly similar down there. But technically, Jeff's penis is the longest while Josh's penis absolutely has the most girth."

"I've noticed the same thing."

"So I was just curious." Deidra added. "When you're having sex with another man, whether sucking him or letting him fuck your ass, which do you prefer? A longer cock or a fatter cock?"

"Hmm."

Darren took a sip of his wine, carefully considering Deidra's question.

"That's tough to answer." Darren admitted. "They each have their positives. A thicker penis will obviously help stretch things out, which is fun. But then a longer penis can get in there nice and deep. I'm not trying to give a cop out answer, I just honestly don't think I can pick a favorite."

"I believe you. And I think that's a perfectly acceptable answer." Deidra told him. "You don't care if it's long or fat, you just enjoy a nice, hard cock."

"Exactly!" Darren said. "What about you? I'm sure you've sampled a wide variety of men. Do you have any preferences on what you look for in an ideal penis?"

"Not really. I mean sure, seeing a guy whip out a massive dong is great. But it's not a requirement." She answered. "For me, it's more about the personality of who I'm having sex with. Seeing you fuck those dudes at the party made me interested in you because I could tell you were open-minded about kinky sex. I only got more interested when you asked to watch me pee. I could tell you were going to be fun, so I was excited about having sex with you."

They paused to take another sip of wine.

"I'm curious what other kinks and fetishes you have." Deidra continued. "The pee stuff was a wonderful surprise. What other types of dirty things get your cock hard? What kind of porn do you like watching most?"

"That would take a long time to answer." Darren said. "I watch all sorts of different porn."

Deidra laughed again.

"That sounds like me, so I get it. I love watching all sorts of porn." She told him. "Okay, so I imagine you've seen all of the standard stuff like lesbian porn, anal, orgies. Not to mention hardcore gay porn. Am I right?"

"You are. I enjoy all of those."

"So what about the lesser-known subcategories? After last week, I assume you still enjoy watching some watersports videos?"

"You could say that." Darren answered with a smile.

"Hmm. What else?"

"I don't know. I enjoy random things." Darren explained. "Like when I took the time to smell your asshole at the party. I really enjoyed that."

"I'm glad you enjoyed sniffing my butthole so much." Deidra said, winking at him. "That's exactly the type of raunchy stuff I love hearing and knowing about."

"I guess something similar would be dirty panties." Darren added. "I am fascinated by a well-used pair of panties. Just seeing them and wondering what fragrances they may hold really gets me going."

"I see." Deidra noted, taking another sip of wine. "I suppose a panty fetish isn't too outlandish at all. That seems to be fairly common in most men."

"I'm really enjoying this conversation. I think the wine is helping me relax about being honest with you about these things." Darren told her.

"I'm glad." Deidra said, reaching out and feeling the bulge in Darren's jeans. "I'm also glad that your penis is hard."

"What do you expect? We're talking about sex, and cock, and smelling and fucking asses." Darren joked.

"Speaking of anal sex..." Deidra continued. "... what about pegging? Are you into that?"

"Very much." Darren admitted. "I've never been pegged, but the idea of submitting to a girl's cock, real or fake, drives me wild."

This answer caused Deidra's to raise her eyebrows as she continued to caress Darren's bulge.

"That was a very interesting way you just answered that question." She told him. "You said 'real or fake'... have you ever masturbated to transgender porn, Darren? Ladies with big tits and big dicks?"

Darren smiled again as his manhood twitched in his jeans, against Deidra's hand.

"You could say that I have a few times, yes." Darren said. "My favorite trans pornstars are Chanel Santini and Khloe Kay, by far. Aubrey Kate is beautiful and also has a really sexy, suckable penis. And I think she's newer, but Jade Venus has a really sexy personality that matches her cock."

"Sounds like you really enjoy that genre of porn." Deidra quipped. "I don't blame you. I enjoy it, too. I think it's cute that you've seen enough to have a list of favorite stars though."

"What can I say? I think it's almost a strong psychological turn on." Darren added. "You see a beautiful woman, and then her clothes come off. And then... surprise! You see an outline of her huge dick bulge in her panties. The right penis looks very, very sexy in a skimpy pair of girly underwear."

"Is that so?" Deidra asked, sipping her wine. "What about yours, Darren? Have you ever worn a pair of panties?"

Darren paused, blushing and nervously finishing off his wine.

"I've certainly thought about it." Darren finally admitted. "But I've never tried it."

"Hmm. I bet you'd look really cute in panties." Deidra said, winking at him. "If you play your cards right, maybe I'll let you try mine on later tonight. Or maybe I'll just make you put them on."

Darren smiled at her, intrigued by the offer of perhaps slipping into her underwear.

"What about you?" Darren asked. "Any other kinks or dirty secrets I should know about?"

"Well..." Deidra started, pausing to also finish off her wine. "...I think we're pretty well aligned on the kinks. I will add that I do enjoy a good, hard spanking from time to time. And there is one very naughty secret that only a handful of people know about."

"Do you trust me enough to tell me?"

Deidra gave Darren's bulge another squeeze through his jeans.

"I think so." She answered. "I just hope it doesn't weird you out or upset you."

"You're talking to a guy that likes to smell your ass and also a guy that licked you clean after happily watching you piss."

"That's true. Just promise me you'll keep an open mind."

"I promise."

"There's this guy that I like to hook up with from time to time. He's a few years younger than me." Deidra explained. "His dick is over eight inches and he knows how to use it. His name is Brad. We've been having sex for fourteen years and I have no plans to stop sleeping with him."

"Over eight inches, huh? Brad sounds awesome. I wouldn't mind spending some time with him myself!"

"Maybe that can be arranged. I know he's fooled around with other boys once or twice."

"But I have no issues with you continuing to have sex with him. As far as I'm concerned you can fuck whoever you like." Darren told her. "Why is your relationship such a secret?"

"Because he's not just some random guy or friend that I fuck." Deidra said. "He's my brother."

"Oh wow."

Darren's erection throbbed in his jeans against Deidra's hand.

"Is that too weird?"

"Not weird at all." Darren replied. "Sounds like two consenting adults having fun to me. And it sounds like your brother has quite a cock! I wish I had a sister like you when I was growing up."

Deidra giggled.

"I'm glad it doesn't bother you." Deidra said. "And yes, he does have a marvelous cock. But at the moment, I'm more interested in the cock I've been fondling through your jeans."

"I think it's quite interested in you as well." Darren told her. "Particularly interested in exploring that tight little hole in your ass."

"Then I guess it's time we head to the bedroom."

Darren excitedly led Deidra to his bedroom. They both started to get undress, first removing their respective tops. Darren admired Deidra's breasts as he pushed down his jeans, freeing his fully erect penis.

As Deidra slid her skirt down, Darren got a wonderful view of her buttocks in a pair of red, bikini-cut panties.

"May I help you with those?" He asked.

"Be my guest."

Darren knelt down behind her, unable to resist his desire to push his face into her crack, against the material of her underwear. He inhaled her aroma, further elevating his lust. Reaching into the waistband, Darren pulled the underwear down, exposing her rear.

Darren could see the end of Deidra's butt plug between her cheeks. He reached into her crack, slowly pulling the toy from her ass. She had told the truth about it matching the 4" penis-shaped plug he had received. Darren gave the toy a quick sniff before popping it into his mouth and sucking it clean of her anal flavors.

"Good to know you like a little ass to mouth action." Deidra snickered. "I enjoy it quite a bit myself."

Darren slid the toy out of his mouth and set it aside as he got to his feet. His erection brushed against Deidra's bare cheeks which only made him that much more eager to penetrate her voluptuous bottom.

Deidra put one knee on the bed and bent forward, giving Darren a clear line of sight to his anal target.

"Do it." Deidra said. "Put that cock in my ass, Darren."

He didn't need to be told twice as he moved forward, easing his erection into Deidra's anus. As Darren entered her from behind, Deidra moved her hand between her legs to play with herself.

"That feels nice." Deidra told him as she felt the penis move further into her rectum.

"Feels great on my end too." Darren replied.

It didn't take long at all for Deidra's anus to accept all seven inches of Darren's cock. She continued to play with her clit and her pussy as he began to fuck her ass.

As Darren slid his dick in and out of her rectum, he continued their conversation from earlier.

"How did you end up fucking your brother?" He asked.

"It just kind of happened one day." She said. "He was never good at hiding things and I was constantly catching him masturbating with my panties. Smelling them, jerking off into them."

"I can relate to that."

"I'm well aware." Deidra replied with a giggle, continuing to fondle herself. "I didn't really mind. And then one day... I don't know. I was horny so I got naked and stormed into his room, asking if he'd prefer to smell my scent directly from the source."

"That's hot."

"He thought so too." Deidra added. "My intention was just to let him smell my pussy and jerk off, but then he whipped out his pecker. When I finally got my first good look at it, I just couldn't help myself."

"You said it's over eight inches. I don't blame you!" Darren told her, fucking her ass even harder. "I've never seen your brother's dick in person but I already want to play with it myself."

"I saw how big he was and my horniness took over. I started stroking him which led to him exploring me with his fingers." Deidra continued. "Next thing I know, I asked if he wanted to have sex and we fucked. It was amazing. And we've been fucking whenever we get the chance ever since."

"That's awesome!" Darren said. "Your brother is one lucky guy."

"I consider myself pretty lucky too." Deidra added. "Like you said, it's a big cock. I'm glad I have such easy access to it."

Darren's erection continued to easily slide in and out between Deidra's cheeks. She moaned as she took the dick and rubbed her clit at the same time.

"Keep fucking my ass." Deidra demanded. "You're going to make me cum."

Darren was happy to oblige, ramming his cock into her and exploring the depths of her bowels. Deidra's moans were becoming louder with each thrust.

"Normally I'd prefer to blow my load deep inside you." Darren told her. "But since you mentioned ass to mouth earlier, maybe I'll pull out and let you taste your own asshole on my dick before I cum."

"Whatever you want to do, baby." Deidra panted. "I'd love to taste your dirty penis right out of my booty hole!"

Darren could feel her sphincter squeezing his erection as she began to have an orgasm. He gave her a smack on the ass as encouragement.

Once Deidra's climax slowed, Darren slid his throbbing dick out of her asshole. Deidra turned around and dropped to her knees, opening her mouth and presenting a new hole for Darren's cock to enter.

"Take it." He told her. "Clean your ass off of my dick!"

Deidra immediately put her mouth to good use, licking up and down Darren's shaft. Then she fondled his testicles and slid her mouth all the way down his erection.

"Fuck yes. Suck my cock." He encouraged. "I'm about to cum."

Deidra sucked and slurped, giving his balls a gentle squeeze. That was the final push needed as Darren's penis twitched in her mouth, ejaculating generous ropes of semen onto her tongue. Deidra kept the dick in her mouth until the flow of fresh, warm sperm ceased. She then carefully slipped her mouth off of his manhood.

Getting back to her feet, they wrapped their arms around each other and began to make out. They swapped the mixture of cum and anal juices back and forth, ultimately coming to an unspoken agreement to split it, each of them swallowing their respective portion.

"No wonder you like licking and eating my ass." Deidra said with a giggle. "I taste pretty good."

"You taste amazing." Darren agreed. "Even better mixed with my cum."

"True. Your cum is yummy, baby."

They gave each other's ass a squeeze as they broke away from their hug.

"Feel like doing something naughty?" Deidra asked.

"We just did anal and shared my cum." Darren said. "What else did you have in mind?"

"Just a couple of fun things to try together." Deidra told him. "I was thinking that first, you should pick up my underwear and try them on."

Darren's eyebrows lifted.

"Will you wear my panties, Darren?" She asked. "Please?"

"It's just underwear, right?" He noted. "No harm in trying them on, I guess."

Deidra smiled with glee as Darren took hold of her previously discarded panties, stepping into them and pulling them up into place. They were a surprisingly nice fit, and Darren playfully made a few poses to show them off.

"Looking good!" Deidra complimented. "And you're right... seeing that bulge in the front is sexy."

"They're honestly not bad at all. I thought they'd be uncomfortable." Darren admitted. "Maybe I could get used to wearing my girlfriend's panties."

"Yay, that makes me so happy that you like them!" Deidra exclaimed. "Where's your phone? I want to get some pictures."

Darren grabbed his phone from the bedside table and handed it to her. She had him put a hand on his hip and pose for her again, getting a close up of his front side. Then she adjusted the angle to get a better shot of the protruding bulge.

"Okay. Turn around." Deidra instructed. "Show me that ass, baby!"

Darren turned around and was happy to receive more kudos from her.

"They look amazing on your butt." She said. "I could just pinch those adorable buns!"

Deidra took a few good pictures showing off Darren's backside in her underwear and then handed the phone back to him.

"You should absolutely send those pictures to Josh and Tiffany." Deidra suggested. "I need to go grab something."

"Where are you going?"

"I have another little surprise for you, but it's in my purse." She explained. "Just send the pictures. I'll be right back."

Darren watched Deidra's bare ass as she left the bedroom. He then followed her advice and shared the photos with his best friend, Josh, and his wife. It didn't take long to receive their feedback, as he felt his phone vibrate multiple times.

FROM: Tiffany

Nice undies, panty boy!

Darren blushed and felt flattered by Tiffany's approval. He then tapped over to his next message.