How Cyn fell down the rabbit hole

Cynthia was staring at the ceiling, gasping for air as John took his time to admire her, watching her come down from her orgasm on his by now soaked sheets. A smile graced his lips as he saw her chest heaving, smelled her arousal in the air. He savored the time it took him to actually take off his clothes, wanting to undress for once instead of just unequipping them as he had done so many times before. Near the end, he could see Cynthia’s eyes following him, a small moan escaping her lips as she saw him finally pull his boxers down, freeing his engorged manhood, enhanced by so many achievements that she had been part of too.

“Thank you, Sir,” Cynthia whispered at him, weakly tugging on her bonds as she spread her legs trying to entice her boyfriend into playing with her some more. “Did I do good?” she asked, hoping for praise.

“You slipped up there for a moment,” John remarked with a laugh, sticking his tongue out at her as he explained. “You called me John when you were begging to cum, though we are both new to this, it’s logical. I’m already very glad you are letting me do this with you.” John then sat down on the bed next to her and gave a small kiss to her forehead. Cyn’s eyes turned into small crescents when John asked her, “Are you alright? Nothing hurts? Want to continue?” having taken the rules that Cyn had to be comfortable at all times to heart. Not wanting to ruin a good thing by making his girlfriend uncomfortable like this.

Cynthia nodded and gave an awkward cough. “Right, I, ehm, sorry. It’s great to get my fantasies played out; it’s a bit overwhelming. Sorry if I slip up now and then.” After that she tugged on her bonds, trying to get them rolling again by reassuring him. “Don’t worry, I’m comfortable and ready for whatever you have in mind, Sir.” Her hips gave a weak little hump to give weight to her words, much to John’s amusement.

“If you say so, my love. Then, I think it’s about time that you give back some pleasure. A spoiled sub is a lazy sub, after all,” John quipped as he got off the bed and moved between her legs. He had planned to tease her longer, but the need he felt from his nethers and the surging libido made him crave some pleasure of his own. Something to work towards, he thought before focusing on the task at hand. He stroked his cock a few times while looking into her eyes, then slowly pressed the fat, bulbous tip into the snug embrace of her folds. He saw how Cynthia’s eyes went wide as he pushed forward, only to pull back just before the full tip pressed into her.

“You bastard,” she grumbled with a pout.

“Sir bastard, to you,” John said with a swat to her inner thigh, causing her to flinch but smirk.

“Sorry, Sir,” she spoke softly, looking at him, her eyes begging him to put it back in.

“I remember there is something we were going to do, babe.” John smirked as he pulled back, fighting down the urge to just go back and fuck her like he wanted to, but to him, even in his lewd mindset, what he was about to do was way more important than getting his dick wet, a fantasy he had on his mind ever since seeing her thighs last Monday, so he started to fiddle with his inventory. A copper bracelet appeared on his right wrist seconds later. He knelt down next to the bed and blew a bit of air on Cynthia’s folds, seeing the juices flow freely as a testament to how turned on his girlfriend had gotten.

“I recall someone telling me that they wanted me to play with a certain something of theirs,” John spoke deliberately slowly, placing his thumb on her backdoor and casting a quick Cleanse on it.

“Ooh, well, please be careful,” she asked him softly, spreading her legs as to give John better access.

“That clip of yours was very hot, and I mean, really hot, babe. Let’s see, how should we do this?” John whispered as he inserted mana into his bracelet, then he touched his other hand, a sheen of lube covering it the next second. “Gaia works in mysterious ways, but she does give cool toys,” John mumbled as he slowly put a bit of pressure behind his finger, rubbing Cynthia’s leg with the other to calm her down.

Cynthia in turn closed her eyes and tried to focus on keeping calm, relaxing her body to let John try to do what she had done the day before. It felt different, John’s fingers were a little thicker after all. But not unpleasant, the fact that he had lubed up his fingers also worked wonders. Soon enough, his first digit popped in.

John experienced an incredible tightness. Even if Cynthia was relaxing her body, it was still a bit uncomfortable after all, so John took his time, placing soft kisses on her pussy now and then to keep her excited and horny as his finger slowly moved in and out, finally getting his second digit in after about five minutes of careful wiggling and teasing.

John wiggled his finger around just a bit more, realizing that he wouldn’t get much more in there this time. “We’ll get you there, slowly, one step at a time. How does it feel? To have your boyfriend playing with your virgin asshole, Cinnabun?” John asked Cynthia with a wicked smirk.

“It feels strange, Sir, good, but strange. I’m glad you’re willing to, you know, try out new things with me. I’m a bit jealous of Val though, seeing as you managed to actually get in there, and I can’t even take your full finger yet.” Cynthia sounded actually upset with that.

John pulled his finger out and wiped it off on the sheet, the last bits of lube disappearing, then he moved back up to Cynthia’s face and kissed her deeply. “Don’t go saying silly things like that. She has had I don’t know how much experience, while you and me are just getting started. Before you know it, you will be able to do anything she can, and more! Just give it time. I’m willing to try things with you and learn how to do them. Look at me, fumbling my way through domming you! But as long as you are also willing to try things with me and are willing to learn alongside me to make each other happy, then I think we will be just fine.”

Cynthia nodded and moved to kiss him again, breaking their kiss only after she ran out of breath. “Thank you, John. I appreciate it,” she mumbled with a sweet little smile. “And well, not to, you know, be an uppity sub and all, but I am still quite horny… Does letting you play with my ass and not resist entail I get a reward?”

John snickered. “Oh, I think it does. What does my beautiful little girlfriend and pet want then? For being such a good girl?”