Coming Together

Skye had what felt like a hundred dildos already. David couldn't guess what was so special about this new one, but waited patiently. Skye emerged, beaming, purple dick in hand. She jumped to sit beside David and they examined together. It was not realistic looking, more like an idea of dick, with a swelling that resembled the glans, but it was smooth and featureless. On the other end, where some of Skye's dicks had balls, this one had something else. It widened into a flattish base, the lower end of which was connected to a weird bulb. It wasn't the biggest David had seen, not even close. He turned it in his hand, puzzled.

"It's a strapless strap-on!" Skye exclaimed.

David groaned. "Strap-less strap-on? That's stupid!"

"Only the name is stupid! Just look how cool it is!"

David looked. Comprehension lit up his face, and Skye laughed.

"Oh, so this part goes in..." he said, pointing to the bulb and then Skye.

She nodded emphatically. "Want to see me try it on?"

Now that David knew what the dick was for, he eyed it with apprehension. It wasn't the largest, but then he wasn't accustomed to anything very large in his ass. True, he had grown to love Skye playing with his ass when he orgasmed, and the few times Skye had talked him into trying a toy had been good, but still...

Skye seemed to notice his reluctance. "I won't ravage you with it, I promise," she said. "And it was the smallest I could find! Oh, come on. Just look."

Skye hopped up and started to remove her pants. David looked at her, always as excited to get to see her in less clothes, and waved the dick at her. "I get that you've tried this on before?"

"Sure I have!" Skye said. "I was too impatient to wait for you to get here, wasn't I?"

David knew she meant she had tried it on at home, but for a moment he pictured a fitting room in a sex shop, with Skye looking at herself in the mirror like she was now: undressed from waist down, ready to fit the purple dong inside her. He smiled. Skye smiled back, and reached for the toy. She eagerly lubed the bulb end up and spread her legs.

"Just like that, huh?" asked David, still smiling.

"Uh-huh, it's, uh... there we go," Skye said as she pushed it in, adjusting her labia.

She stood beside her dresser, beaming, purple shaft protruding from her pubic hair. The sight was unreal, but she was so excited it was starting to catch on to David.

"See, I went to the sex shop, because I wanted to get something for you," Skye said, turning this way and that to see her reflection from different angles, offering the same view to him. "I don't have that many that are suitable for anal, you know. So I wanted something, like, more slender, and I thought I'd just use it on you, but then I started talking with the guy and he showed me this, and I was like... well what if I could really use it on you, you know?"

"Uh huh," David said and eyed the dick doubtfully. "So how long have you had these pegging fantasies for?"

Skye grinned and pretended to jerk off the purple silicone jutting from between her legs. "Well I haven't really, but... with you... I thought... okay, yes, I would really want to."

"Yeah, but that is kind of big."

"I promise to go slow," Skye said and grinned even wider. "Besides, yours is bigger, and I have let you in my ass. Don't you trust me?"

David cocked his head. He wanted to argue that it was different, but couldn't really say why it was different. Skye had always been careful and gentle with things she'd put up his ass, and he had no reason to doubt this would be different. Besides, her enthusiasm was contagious.

"Okay," he said, smiling. "So... what... should we do something else first?"

"I can give you a blowjob if you want?" she said, walking to the bed and pushing him to lie on his back. "I don't want anything, because, well I think this will be kind of active, and I want to save my strength."

"Mm-hm," he said, letting himself be pushed down. "Okay, we can try that, but be careful, okay?"

"Okay!" Skye said gleefully.

She bent down to kiss his tummy, then reached for the lube and started spreading it on his ass. He spread his legs, planting his feet on the bed, and squirmed when Skye lifted his balls up and out of the way and it tickled. He realized he was more than a little turned on already. When had he become such an anal slut?

No, not slut, he corrected himself and grunted when Skye slowly pushed her finger in, twisting and turning to spread the lube everywhere. Why would it be slutty to have things done to his anus, when it felt normal to do things to hers? Why was he having these metaphysical conversations with himself when he was having his ass fucked in the most delicious way? Oo, and here came another finger.

They smiled at each other. Skye pulled her fingers out slowly, then positioned the dick. The angle wasn't working for her, and she looked down with acute concentration as she tried to work it out. David looked at her furrowed brow and felt a warm flicker in his heart. She was so cute when she was all focused like that!

"Okay, maybe if I put it in you first, and then," Skye muttered.

She pulled the toy out of herself with an impatient schlurp, and started to ease it into him with both hands. He breathed and relaxed, focusing on how the toy stretched him, not any bigger than her two fingers but cooler and differently shaped, and how amazing it felt once the slightly bulbous head was in and the shaft started to fill him. Skye was slow and meticulous, adding lube in generous amounts and going back and forth making sure she got it everywhere.

David eyed Skye's body, mostly her boobs, while she worked. Routinely he reached for his cock, which had been quite hard on its own and quickly filled up the rest of the way at his touch. He was amused by how accustomed he was to getting off while having her play with his ass, and wondered if he had now made himself be dependent on this. He wondered why he was suddenly so concerned over this. Skye had worked the cock mostly inside him, and now she grabbed the toy to try to reinsert it into herself.

The angle still didn't work for Skye, and the way she tried to twist it pressed in the most uncomfortable way in all the wrong spots. David yelped and tried to follow the movement, and after a few intense moments Skye released the toy with a disappointed look on her face.

"I guess it doesn't work," she said. "I'm sorry, but what if I just work it by hand?"

"Uh, uh huh," said David, trying to catch his breath. "I think, maybe if we try it in another position?"

"What do you mean?"

They looked at each other, then at the purple contraption protruding from his anus.

"Well, I think... I think you need to wear it when you insert it, but, like, maybe like this?"

He pulled the toy out slowly, wincing when the fattest part exited him. He handed it over to her, then turned and got on all fours on the bed, moving a bit further so she could climb in behind him.

"Ooo," she said behind him. "Oh, yes."

He planted his knees wide, lowering his upper body on his elbows, and waited. Skye climbed in behind him, and he peeked between his legs and saw her popping the thing into her pussy again. The wet sounds accompanying this were as exciting as they were depraved, and he breathed slowly and tried to relax the best he could. They had never tried anal play on him on any other position except for him on his back, and this felt different before she had even touched his ass.

Skye positioned her knees close to his, inside of them, and there it was. David felt the tip of the toy against his opening. Skye planted one hand just above, and he guessed she was holding the toy with the other.

He was so lubed up that while the toy still felt way bigger than it looked, it slid in relatively easily. Skye went slow, and they both sighed audibly when the tip slipped in. Skye stopped, taking a two hand hold of his ass and stroked it, spreading and massaging his cheeks.

"I think I like this position," she said and slapped him lightly. "How about you?"

"Just stop with the spanking, will you," David said.

Skye took a tentative hold of his hips. David pushed back a little, and Skye was still, letting him take the toy in. Somehow getting to set the pace made David calmer, and he exhaled slowly while he impaled himself. He was surprised when the top of Skye's thighs met his, and he realized he had taken it all.

"Ooo," he said, pulled off an inch or two and slowly back in.

"Ooo," she said, when he pushed back against her and his ass pushed the base of the toy between them against her.

The toy did wonderful things to his prostate. Nothing they'd ever tried reached this deep, or filled him this full, and he pulled off again and then back innnn. His dick was harder than it had ever been. It nudged against his abdomen, hot and rigid, and smudged precum over his skin.

"Oh yes," Skye said with a hoarse voice. "Oh yes, I do like this position."

Her grip tightened and she started to move with him. She panted a little, and her movement was not super smooth, she had a tendency to push the last bit with a bit too much force. David didn't care. He humped back against the toy, filling himself up, shamelessly stimulating his prostate. He was overwhelmed with this feeling, rotating his hips minutely to search for the most perfect angle, and he gripped the bedding in front of him with tight fists. He wasn't as relaxed as he was when he was laying down, but the ability to match Skye's movement made it oh so worth it.

"Oh god, oh god, oh god," Skye muttered and pulled him harder against her.

Air around them filled with sex noises, grunts, panting, the slapping sound where their bodies met. David thought wildly that if she had balls they would be smashing his right now, then wondered if the toy could be supplemented with fake balls, then wondered if he was secretly gay. His capability of complex thoughts was vanishing more by the second, and his thighs started to twitch and spasm on their own.

He wanted to come. He wanted to come so bad that he didn't remember ever, not once in his history of orgasmic frustrations, wanting to come this bad. He was pushing back mindlessly, probing his prostate again and again, and it took him what felt like forever to come up with the idea of touching himself. He was so focused on pushing back his ass that it took a few more moments to negotiate how he could have the weight of his upper body on one arm, while he reached back with the other. He had a fleeting idea of lube, but then he had leaked so much precum it had almost the same effect. Besides, he was so horny now that he would've rubbed his dick with sandpaper if that was what it took to get some friction on it.

It was very difficult to get any kind of grip, let alone seek the angle or the rhythm he usually came to, but it turned out it didn't matter. Once he got any kind of grip on his dick he lost whatever coordination or rhythm he'd had, and had no idea if he was trying to fuck backward into the toy, forward into his fist, or maybe move his hand. He was on autopilot, whimpering, spasming, grasping, groping, and then he erupted so hard that the first jet hit him in the chin. He moaned loudly and his hips froze in place, but Skye behind him didn't stop, she kept pushing against his prostate again, and again, and again. She was very close to him, she only pulled out very minutely, but every insistent nudge felt right where it mattered.

He rocketed through the longest, most intense orgasm of his life. The relentless pounding on his prostrate prolonged it so that he wondered if he would come again, or if he should beg for mercy, and it wasn't until Skye finally, erratically jerked to a standstill that he realized she hadn't been doing that for his benefit: she had come too. She had been rutting against the base of the toy, and now she was so spent she pulled out of him with a wet sound and almost fast enough to be frightening, and then she fell beside him uncontrollably, like a ragdoll. David fell forward on the pool of cum with as little grace, and they lay beside each other, panting.

Weakly, David turned his head to see Skye. She wiped sweat off her forehead and smiled at him. "Damn, that's hard work! I don't know how you can do that for so long. I mean, we've had some pretty long sessions before."

"Mmm," David agreed.

Skye laughed. "That good, huh?"

"Uh-huh."

Skye sighed happily and looked down along her body. David followed her gaze to the dick, which still stood proud and purple between her legs. She reached to detach it, giggling and gasping, sensitized after her orgasm.

"Ooo, fuck, here we go," she said when it finally popped out. "Oo, I wonder if I bruised my clit on this thing. But damn, it was good. Kind of... required a lot of work, but it was... different, and oh fuck, how hard I came. Did you come too? I thought you did, but I was kind of... preoccupied."

He turned a little on his side and wiped the sticky mess from his skin. "I did. About a bucketful, it seems."

Skye laughed, a bright and tingling laugh, and swatted his side playfully with the dick. "So you want to do it again?"

"Fuck yes I do," he said, lazily turning back on his front. "I want, I want to... I want to marry you."

Skye laughed again. "That good? Ha, but no. But maybe we could consider going steady."

"Uh huh," David said. "Definitely. I want all of you for myself."

He was so relaxed he had trouble focusing his eyes. His ass throbbed, and he thought he might have to sit carefully for a while, but simultaneously he knew he wanted to explore this further. And he couldn't think of anyone he'd rather do it with. He thought back to his random dating life before their arrangement, and it felt distant and very laborious compared to their easy coexistence.

"Let me rephrase," he said with a sloppy grin. "With benefits like that"—he gestured toward the purple dick—"I want to be more than friends. What do you think?"

Skye stretched and turned to face him. Her smile was radiant and satisfied.

"I think we can do that," she said and booped his nose with the dick. "Merry Christmas, boyfriend."

"Merry Christmas," David said quietly and reached to kiss his girlfriend.