Trying Something New Pt. 05

FROM: Josh

Cute. Somehow wearing panties makes your ass look even more fuckable!

Again Darren smiled as he read the sweet words from his best friend. He set his phone down as he heard Deidra.

"Surprise!"

Darren turned around again his eyes went wide. Deidra was still naked, but now she had a realistic, 8" strap-on dildo extending from her pelvic area.

"Wow."

"I thought I could return the favor and we could trade anal." Deidra said. "Do you like my cock, baby?"

"It's a very impressive dick."

"Why don't you get on the bed and turn around?" Deidra suggested. "Then I'll give that ass exactly what it needs."

"I guess I need to take off these panties."

"No, leave them on!" She demanded. "I'll just pull them to the side when I slide my toy penis into you. I want to see if I can make you cum in them."

"You're the boss."

"Damn right." Deidra hissed. "At least as long as I'm wearing this cock."

Darren climbed onto the bed, getting on all fours. His quickly growing erection was filling the crotch of the panties as he observed Deidra lubing up her strap-on. When it was ready for action, Deidra got onto the bed behind Darren.

"Ready?"

"Yes."

"Do you need my cock in your ass?" Deidra asked.

"Yes. Please!" Darren pleaded. "Please give me every single inch!"

Deidra smiled as she pulled the underwear aside, positioning the tip of her dildo next to Darren's exposed rosebud.

She then giggled as she began to insert the strap-on into Darren's rear.

"Good boy." She said. "Relax, open up, and take my dick, baby."

Darren moaned as he felt the toy penetrating him. His fully erect penis wanted to be freed but remained secure and restrained inside of Deidra's panties.

"How does it feel to have a girlfriend that's willing to fuck you in the ass?"

"It feels wonderful." Darren admitted as he received the dildo. "It's honestly a dream come true."

With the toy safely inside of Darren's anus, Deidra took hold of his hips so that she could increase her thrusting. There was no resistance to the toy penis sliding between his buns and probing deep into his bowels. Each thrust had Darren moaning in delight.

"You really know how to work that dong!" Darren commented.

"I'm no stranger to using a strap-on. Mostly using it on other girls." Deidra explained. "But it's pretty hot to use it on a man. And especially one that takes it so well!"

Deidra continued to drive the dildo in and out of Darren's asshole.

"I love how easily you surrendered to my cock." She told him, the phallic toy massaging his prostate. "I want to keep fucking your ass hard and deep until you cum."

"It's going to happen sooner rather than later the way you're thrusting that dick into me." Darren announced, his penis twitching again in Deidra's panties. "I'm happy to bend over for you anytime you want to give it to me!"

Deidra giggled, happily piping Darren's horny rear with her strap-on. Darren remained still, accepting every inch of the magical toy into his anus.

"I think I'm about to bust."

"Good! I want you to cum as I'm fucking you!" Deidra said. "I'm not pulling out until you've pumped out every last drop."

Darren gripped his ass muscles around the dong as twitched again, this time releasing generous globs of fresh semen into the gusset of Deidra's panties.

Deidra remained true to her word, continuing to plunge her toy in and out of Darren's rear as he erupted. As the last few droplets soaked into the fabric of her underwear, she finally slid the dildo out of his well-used fuckhole.

"That was amazing." Darren said as he crawled over and got off the bed and onto his feet. "I hope we can make that part of our regular routine."

"Of course!" Deidra replied happily. "And not just me fucking you with my dildo. I think we should work more panties into your underwear rotation."

Darren chuckled as he admired the toy penis she was still wearing. The same toy penis that had just fucked him to an orgasm.

"I think I'd be okay with that." He told her. "They're actually more comfortable than I expected."

Darren pushed down the cum-soaked panties, stepping out of them. He then carefully set the soiled underwear on his bedside table. Deidra also got off the bed, loosening her harness removing her strap-on, setting it next to the panties.

"I'd love for you to spend the night." Darren offered. "If you'd like to stay."

"I would like that." Deidra answered. "I'd also like some more wine."

The two of them walked back to the kitchen, completely naked and fully exposed to each other. They remained nude as they indulged in more wine and continued talking.

When they finished the wine, they decided it was time for bed. They enjoyed a vigorous round of standard sex, ending with Darren's sperm being deposited deep into Deidra's vagina. Afterward they fell asleep with their dirty, naked bodies snuggled against each other.

***

The next morning, Darren rolled over, well aware of his morning wood brushing against the bed sheets. He looked over and smiled as the sight of Deidra's dildo and underwear reminded him of the previous night's activities. He then turned his head the other direction and admired the beauty of Deidra's naked body beside him.

She had kicked away most of the sheets and was on her stomach, giving Darren a wonderful view of her bare ass. He wanted nothing more than to lean over and sink his face between her soft cheeks.

Before he could do anything, Deidra began to stir and she turned her head toward Darren, opening her eyes and smiling at him.

"Are you looking at my butt?" She asked.

"What can I say? It's a great butt." Darren told her. "I'd be stupid not to look at it when given the chance."

"You're sweet."

Deidra rolled over and sat up. She leaned over and gave Darren a good morning kiss. She then looked over at the tent under the covers.

"Looks like your penis is awake." Deidra said with a giggle.

"It sure is." Darren replied. "I think he's hoping to find his way between your legs again."

"Unfortunately I can't stay too long. I need to run some errands." Deidra explained. "But I should probably take a shower first. Maybe you'd like to join me?"

"Sounds like a plan."

The two of them made their way to the bathroom where Darren started the shower water. As they were waiting for the water to warm up, Deidra noticed that Darren's erection had lost a bit of its luster.

"Oh no!" She said playfully. "Did your cock fall back asleep?"

"He's just resting." Darren joked. "I'm sure you'll have his attention when I'm washing your tits and ass."

"I think I have a better idea on how to wake him up." Deidra said, holding the shower curtain open. "After you."

Darren stepped into the shower, followed by Deidra. Darren had his back to the shower. Deidra smiled and hooked one of her legs around his waist, pulling him close. Close enough that his penis was pressed against her twat.

As he felt the warm water on his back, Darren also felt a warm sensation washing over his manhood. He looked down and then back at Deidra excitedly.

"Is that what I think it is?"

"Is that okay? I would've asked first but I wanted to surprise you." Deidra said with a wink. "Is it okay that I'm peeing on your cock?"

"That feels really nice." Darren answered, quickly becoming aroused by the sensation of Deidra's urine coating his genitals.

Darren grabbed her ass and held her against his body even harder as she relieved herself. By the time she was finished, his dick was rock hard.

"I need to fuck you." He said. "Right now."

Darren gave his shaft a quick rinse and then had Deidra turn away from him. He smacked her ass before positioning his cock between her legs and inserting it into her moist cunt.

"Oh yeah!" Deidra said. "Give me that cock you dirty boy!"

Darren eagerly thrusted his erection in and out of her slit, pounding away at her pussy. He looked down at her beautiful, wet ass while they made love. He pushed her cheeks apart and stared at her magical, puckered orifice.

"You have such a sexy asshole." Darren complimented.

"Right back at you, sugar." Deidra replied as she took his cock.

Being a gentleman, Darren reached around Deidra's waist, moving his hand between her legs so he could rub her clit as his penis pumped in and out of her. Deidra responded positively, pushing herself back against Darren's probing dick.

"Yes. Fuck me. Fuck me, baby!" Deidra cried. "Give me that cock!"

Darren was happy to give it to her, slamming his manhood into her soaking wet cunt.

"How does it compare to your brother?" Darren asked. "Does it feel as good as when he's fucking you?"

"Almost." Diedra teased.

Her teasing inspired Darren as he gave her bare, wet ass another smack and began to drill her twat even harder. She moaned as his fingers massaged her clit.

"Oh yes. Yes!" Deidra encouraged. "Fuck me. Make me cum!"

Darren's horny penis continued to explore Deidra's pussy from the inside while his fingers pleasured her from the outside. Her moaning increased as she began to have an orgasm.

Deidra's satisfaction seemingly gave Darren the green light. His manhood twitched and throbbed inside of her. He plunged his penis deep inside of her, joining her in orgasm, cum gushing deep into her cunt. Darren kept his cock in her vagina as his semen continued to spew out.

Once his testicles felt sufficiently drained, Darren allowed his penis to slip out of Deidra's soiled fuckhole. With their sex concluded, they spent the remainder of the shower washing themselves and each other, making sure every nook and cranny was accounted for. After the shower, they dried off and returned to the bedroom to get dressed.

"I better not forget that dildo." Deidra noted. "A girl never knows when she'll need to strap on her toy cock! Always have to be prepared."

"And your panties." Darren added. "Don't forget your underwear."

"Oh honey, those aren't mine." Deidra told him with a grin. "As soon as you put them on and took my dong up your ass, those became your panties. Another gift from me to you."

"Really?"

"Yep. All yours." Deidra reiterated. "And based on our earlier conversations, I expect them to merely be the first of many, many more pairs of cute panties you'll own and wear."

Darren started to blush, but was also excited by her words.

"Well thank you."

"My pleasure." Deidra added. "And don't be shy about using your new plug either. You should have it in your ass as often as possible, darling. Especially in public. It's so much fun to walk around in public with the secret knowledge of having something shoved up your little butthole and no one else knows. But you know it's there. Inside you. Filling you and keeping you loosened up for whatever the day may bring."

"I promise I'll put it to good use." Darren told her. "I might even take it for a spin after you leave."

"That makes me so happy to hear you say that." Deidra said. "And we'll go dildo shopping soon too. You really should own a toy penis you can play with. It'll enhance your masturbation."

Darren couldn't help but feel excited at the prospect of his girlfriend helping him pick out his first dildo. Advising him on the size, shape, and length she would recommend.

Darren reached around her waist and pulled her close, kissing and making out with her. His hands cupped her wonderful buttocks through the material of her skirt. He then slid one hand under her skirt to feel the bare skin of her ass cheek once more. He pulled back from the kiss momentarily.

"It's so sexy knowing you're walking out of here wearing a short skirt and no underwear." Darren said. "I hope a complete stranger gets treated to an accidental glimpse of your pussy."

"Maybe it wouldn't be an accident." She replied. "I have no problem flashing my body. Exposing myself and my privates. I like it when I know someone is looking at me and most likely having perverted thoughts about things they'd like to do to me."

Darren squeezed her buns firmly before pulling his hands back to himself.

"I'm definitely going to think perverted thoughts about you after you leave." Darren assured her. "And also dirty thoughts about you getting pounded in every orifice by your brother's cock."

Deidra giggled.

"I'm actually going to be seeing him later today. There is no doubt in my mind that he'll offer me his yummy penis." Deidra said. "Maybe I'll send you a picture of his cock. Would you like that?"

"I would love that." Darren answered. "I would love to have a picture of your brother's penis to jerk off to. Looking at it and knowing it's going to be stretching you out. And then when I see you again I want to hear every raunchy detail of what you two did together."

"Deal." She said. "And I'll tell him about you and see if he might be willing to give you a chance to experience his cock for yourself."

"That would be awesome!"

The two of them embraced in another kiss before Deidra finally turned to leave.