Double Trouble in Helia Pt. 07

"You tease," she moaned as she looked back at him.

Alex finally pulled the thong down her leg sand revealed the toy. He watched the round blue jewel that adorned the plug move whilst Emily pulled her underwear off her legs and threw it to the side. He now had an unobstructed view of her beautiful butt and enjoyed it immensely. His one cock was straining against the fabric of his pants, but he paid little attention to it.

"Do you like the surprise?" his lover asked him whilst looking over her shoulder.

In response, he pressed against the plug and forced the steel end to be flush with her skin.

"Ooh," she cooed. "I take that as a yes."

Alex latched his fingers onto her thighs as he drew his face closer to her rear. He observed the toy up close for a moment before he let his lips graze her the lips of her swollen sex. After traveling all the way down to her hooded clit, he took it in his mouth and gently sucked on it.

"Hmmm, that's great. Don't forget about my tight little hole up there. That's what this was all about."

Alex took the plug between his fingers and slowly pulled on it. It was a little tricky, since it was slick with lube, but he got a decent grip on it in the end. As he pulled it back, he watched her tight ring stretch. The toy's diameter seemed to increase and increase, forcing her ass to open up further and further before he pushed it back again. It wasn't a huge toy by any means, but the sight was extremely erotic.

Alex continued the move over and over, each time pulling the plug a little further back before sliding it back into her taut ass. At the same time, his tongue was spelling out the alphabet on Emily's clit. He'd been searching for tips to improve his oral skills and that one stuck out to him. His handwriting, or tongue writing, would certainly not be readable, though the effort was clearly appreciated.

Emily's sighs were drawing longer and longer and her nectar had turned her sex slippery. He used her own liquid arousal to coat his fingers with it and slide them inside of her. He tried to time it with his pulls and pushes of the butt plug, which mostly worked, but it threw his licking off.

Alex pulled the plug a little further out whilst his fingers were pumping in and out of the soaked sex in front of him and to his surprise the toy slid out in its entirety. Suddenly Emily tensed up and she fell to the bed, her arms unable to support herself. He watched in awe as her butthole contracted and relaxed, as if it were winking at him. He put the plug on the nightstand whilst Emily came down from her high.

"Woah," she panted. "I wasn't expecting that, but that was really nice. It wasn't an earth-shattering orgasm or anything, just really nice."

"Do you still need the plug? I already put it away, but I can get it again."

"No, you don't need to. Just drop those pants and lay back on the bed. I just need a moment."

Alex got his remaining clothes off in a record time. Had it been part of the Olympics, he certainly would have scored that golden medal. Well, maybe not, since he hadn't really practiced, but he was still impressed by it.

He looked at his crotch as he lay down. It was a little odd seeing only one cock sticking into the air after seeing two of them for so long. The girth or length hadn't changed whatsoever, but it still felt like there was something missing from the picture.

"So, what's your plan?" he asked his girlfriend.

"I wanted to play with some of these toys," she responded. "I'll be in control, so just lay back and relax. I'll tell you everything you need to know."

She carefully laid the fleshlight and vibrator next to him before giving him a quick kiss on the lips.

"Don't worry about my needs," she whispered into his ear. "I can take care of myself."

Alex held back from jerking himself off as he watcher her unclasp her bra and throw it off the bed, freeing her breasts. He got to enjoy them sway and watched her hard, pink nipples move as she crawled towards him and sat down on her knees besides his head. Her shapely legs were so close, but she didn't sit still for long.

Instead, she swung one leg over his head and positioned her ass above it. Once she was in position, she wrapped her delicate fingers around his hard shaft and began to slowly jack him off.

"Are you enjoying it so far?" Emily asked him.

"The view is nice at least," he quipped as he watched the well-lubed ass and aroused vulva in front of him.

She silenced him by lowering her dripping sex onto his mouth.

"That's better," she sighed as she slowly gyrated her hips, rubbing her pussy against him. "Use that tongue for something better than snarky comments."

Alex took one of her butt cheeks in each hand to hold her in place as his tongue dove between her wet folds. Her breathed in the strong smell of her arousal coupled with the subtle scent of strawberries coming from the lube. He enjoyed the taste of taste of her as he lapped up her nectar.

"Keep that up," she cooed.

He could feel Emily shift above him, but he couldn't see what she was doing. Her hands kept jerking his hard member whilst she lowered herself, pressing her breasts against his naked body. Due to the new angle, he had better access to her little pleasure nub and focused most of his attention there.

Alex was surprised when he felt something warm and wet graze the tip of his cock. He knew it must be her pink lips teasing his hardness. His lover kissed up and down his shaft before she placed her lips against the tip once more and slowly sucked him inside whilst flicking her tongue against his sensitive tip. He could only groan as she took in more and more of his throbbing member into her moist mouth.

Just like last time, she enthusiastically bobbed up and down his shaft, pushing her lips a little further down each time. Her lips wrapped around his shaft and the teasing of her tong shot bolts of pleasure through his system, spurring him on to increase the speed of his oral administrations. They were moaning in unison when Emily pushed herself upright again, exposing his shaft to the air.

She leaned over to the side and he could hear her use the pump that was attached to the bottle of lube, which was followed by wet squelching sounds. Her hand came back and it held the sleek pink vibrator, now coated in a shiny layer of lubricant.

"Here, press this against my butt, but don't push it in yet," she said as she handed him the toy.

Whilst he pressed it against her tight hole and coated her entrance with a fresh layer of lube, Emily grabbed something else from the side. He felt a steady dripple of thick liquid hit his cock, which she used to coat his entire member with. She then wiped her hands more or less clean against his stomach.

"I need you to follow my instructions carefully, Alex. And keep eating my pussy. It feels great," she purred."

Something different press against his slick dick this time. It wasn't as warm as his girlfriend's hot mouth, but it was equally wet.

"Press it against me," she commanded with a husky voice, "and push the tip inside."

He watched the pink toy push Emily's tight ring apart as it slid inside of her. At the same time, she pressed what could only be his fleshlight against his member. The entrance stretched to accommodate his girth and his cock entered the tight tunnel.

"Imagine that you just entered my virgin ass," she said. "How does it feel?"

"It feels great. It- ehm- you are gripping me so hard," Alex groaned it response.

"You can push a little deeper. I took my time preparing my butt, so it should be nice and slippery inside."

He pushed the vibrator a little further and watched as her butthole swallowed another piece of the slender pink toy. At the same time, Emily lowered the fleslight, teasing his cock with ridges that were narrowing the tunnel as he went deeper.

"Start thrusting into me, slowly. I need to get used to it."

It was a little difficult to keep flicking her clit with his tongue and move the slippery vibrator in and out of his lover's ass. Luckily her sphincter wasn't putting up a fight and the toy slid in and out of her smoothly.

Emily moved the artificial ass up and down, massaging his hard shaft with the soft sleeve. It quickly warmed up and the material was hardly distinguishable from the flesh he held in his hand. Squeezing her butt cheek did reward him with a whimper, whereas the toy only made squelching sounds as his cock penetrated the internal rings.

Alex moaned louder as Emily pushed the toy further down his cock, forcing his tip through a tight chokepoint and into chambers that were lined with nubs. His sensitive head was teased mercilessly whilst his shaft was squeezed by the sleeve.

"Do you like my tight ass?"

He was a little surprised she still kept the sort of role-playing up whilst he had trouble focusing on anything beyond making love.

"I love it. I can't wait to be fully inside of you."

"Why wait?"

Emily suddenly picked up the pace and began pumping the fleshlight up and down his throbbing cock. Wet sounds filled the air as the artificial ass slid over his sensitive skin. The anal rings stretched around his girth whilst the bumps and ridges brought him ever closer to his personal rapture.

She drew back almost completely, leaving only a tiny part of him inside of the toy before slamming back down. The slick inner walls felt clamped onto his cock as it pierced the fake flesh.

"Oh, FUCK!" he cried out, overwhelmed by his sudden orgasm.

"Do it! Cum in my fucking ass! Fill my ass with your hot load!" Emily cried.

His climax had been unexpected and hit him like a truck. Muscles tensed up and his neurons seemed to be on fire as his balls contracted. Each time they did, he felt a pulse of his seed fly though his cock and spurt into the toy, coating the inner walls and lubing his cock further. Emily kept pumping the fleshlight up and down his shaft over and over again, pushing his climax higher and higher. It seemed like there was no end in sight for his orgasm as his dick kept spraying his cum inside of the masturbator.

His girlfriend had taken matters in her own hands, quite literally. She had removed one hand from the fleshlight and used it to turn on the pink toy in her ass and start sliding it inside of her. The powerful vibrations stimulation both her tight ass as well as her slick pussy. Seemingly determined to get herself off a second time that night, she grinded her wet slit against Alex with an increasing fervour.

"I, oh- OOO!" was all the sound she made as she reached her own apex.

Still dazed from his orgasm that hadn't truly died down yet, Alex was awakened by a sudden rush of wetness that sprayed against his face. He realised his girlfriend was coming too and tried to lap up as much of her sweet nectar as he could, spurring her on to release even more of it as her pleasure multiplied time and time again.

Emily lowered herself with what little strength she still had as waves of delight wracked her body. Her firm breasts were pressed against his abdomen and her hands rested on her sides.

When Emily's body relaxed, Alex let his head fall back down on the bed and his hands rest on her legs. The only sound that remained after their lovemaking was their rapid breathing. He did not know how long they lay there in silence, but he really didn't care.

Emily was the first to move and she slowly slid the fleshlight of his cock and quickly plugged the hole with her thumb whilst she licked his cock clean. After removing most of his seed and the lube, she pressed her lips against the butthole and removed her thumb. A steady stream of his thick cum leaked out of the hole and she guided it into her mouth with her tongue.

Alex took the opportunity to turn the vibrator off and take the sleek sex toy out of her ass. Her butt shuddered a little when he did it, but she didn't move any more than that.

"It's unbelievable how much you came, Alex," Emily said once she'd finished eating out the fleshlight. "It kinda makes me a little worried about doing actual anal, but also really excited. It would be a shame to waste your load like that, but it's worth it if I can cum as hard as I just did."

She gave his still hard dick a kiss on the head before she got up.

"Perhaps I can get a little more out of it," she said.

"We'll have to see about that. I think cleaning this mess up and having a shower should be a little higher on your list of priorities," Alex responded.

Once they were showered, the pair went back to the bed they had cleaned up and dove under the blankets. Alex had expected Emily to lie next to him like last time, but she sat with her knees pulled up to her naked chest with her arms wrapped around her legs whilst biting her lip for a moment.

"Em? Is there something?"

"I- I need a favour from you," she muttered.

"I'll do anything for you," he whispered as he gently touched her arm.

He cleared his throat when Emily didn't respond, clearly still fighting an internal battle.

"I'll say I'll move the mountains, and I'll move the mountains," he sang, "if she wants them out of the way. Crazy she calls me. Sure I'm crazy. Crazy in love, I say."

"You dork," Emily said as she wiped away a tear from her eye. Her smile told him her mood had at least improved. "My dork, I know."

Alex sat next to her and pulled her into a hug, feeling her soft skin press against his.

"It's true. I'll do whatever you need me to do," he whispered.

"Don't say that until I've explained what it is I need you to do."

He noticed she was playing with a loose strand of her hair whilst she chose her next words.

"I, uhm, want you to have sex with someone. Cherry to be exact."

Alex wasn't sure if he could that to Emily, even if she herself agreed to it. He wanted to help her with whatever it was she needed help with, but he didn't know what kind of impact this would have on their relationship.

"Don't say anything just yet," she quickly added once she saw his hesitancy. "I already told you Cherry's situation is complex to say the least. I'll give you the short version, since the details don't matter too much. She's a little different from most girls, which kinda pushes away a lot of guys."

He watched her take a deep breath, gathering her courage.

"Cherry has a, uhm, penis..." she said after a moment of silence, the last word came out as little more than a whisper.

Alex was taken aback to say the least. He hadn't expected that the cute redhead was hiding that underneath her clothes. It made him wonder how many others had extra appendages on the islands.

"You don't have to do it if you don't want to," Emily said as she studied his face with worry when he didn't speak up.

"Is she trans or whatever the term is?" he asked her. He didn't have any issues with that, but he just needed to figure out what was going on.

"That'd be easier to explain, but no. She's a girl through and through, but she has a penis too. Everything else is still there, even her clit and she got periods before she started taking the pill. Don't ask me how it works because I don't know."

Alex bit the inside of his cheek whilst he wrestled with his thoughts. Emily certainly would like nothing more than see her friend be happy and apparently that involved him sleeping with her. As long as she was OK with it, it shouldn't be an issue he figured.

"I'll do it," he declared.

"With the lights on?"

"What? Why would I turn the lights off? I already have more dicks than the average person, so an extra one won't scare me."

"Sorry..." Emily muttered. "It's just that she told me that's more or less how her first time went with a guy. That way he couldn't see that she was any different."

"He never tried to reach for her clit?"

"I have to say you have pretty high expectations for drunk high-school seniors. He didn't do a lot according to Cherry and the few guys she's been with since weren't much better."

"I'm glad I don't have a previous record to beat," Alex quipped.

Emily playfully poked him with her elbow.

"You better get her off, you jerk," she said as she giggled.

"I will, I will. Don't worry about it. I've got you to practise on after all," Alex responded as he pulled her down the bed.

The lovers shared slow, gentle kisses until sleep overtook them.

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Thanks for reading this chapter!

It took a little longer to make than I had anticipated, but that's just the way it is.

Feel free to leave any and all feedback, suggestions, ideas and comments below.

I'd love to read your thoughts on the story.