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Starting Over (RoleplayMaster)

He smiled as she laid on his chest and moved so his cock was touching her anal hole. "Are you ready for it?" He asked, rubbing the head along it slowly. He reached back with the other hand and played with her tail, loving how it wagged happily.
 
Elena's tail stood up right away when she felt John's cock push up against her ass, reminding her of what they would try next. She gave a little nod, pushing herself back up slowly so she could position herself over him again. She waited until she felt it pushing into her a little before she started to lower herself again, a soft whimper leaving her as she was finding it a little difficult even with his cock still wet with his own seed. "Mmg...nn..." She bit her lip gently as she pushed a little deeper, getting the head in and a couple more inches.
 
He moaned at the very tight hole, biting his lip and he looked at her. "Take it as slow as you need to. I can wait" He smiled, rubbing her breast softly, pinching her nipple. He pulled her tail gently, giving his cock more room to enter her ass.
 
"O-okay..." Having him tease her breast and tug at her tail did help distract her a little from how wide his cock stretched her rear. She did let out a few pleased groans as she would try to lower herself a little quicker, making John tug at her tail a little more. She kept going like this until she was finally lowered on him completely, now sitting comfortably above him. "Nng...it went in all the way..." She was a little surprised that she had managed this, and she had a feeling it would take some effort to keep herself moving.
 
He smiled as his cock got all the way in, a little surprised himself. "That's my girl!" He said proudly. He kissed her softly, still playing with her tail. "Just take it slowly, or do it fast. Whatever you are comfortable with and won't hurt as much" He said softly.
 
Elena felt a little odd being praised for something like this, but with her master in a good mood, she felt she could be happy as well. She was glad he was letting her control this still, as she definitely thought she'd need to take her time. Putting her hands to his chest again, she started to push off of him, whining softly with how she gripped his cock so tightly. When only the tip was in her, she pushed all the way down again, letting out a loud gasp. It seemed that she gave a greater reaction doing anal sex, which she hadn't expected. She slowly started to move at a steady pace, still whining and groaning from this new experience.
 
While she was whining and groaning, he was moaning loudly. He hadn't had sex in a hole this tight before, and it was incredible. He had to restrain from taking over, thrusting hard and all that, as he knew she needed to adjust to his enormous size. He ran his hands along her wet body slowly, a smile on his face
 
Elena would slowly pick up the pace just so she could get used to this quicker, but she may have been pushing it a little. There was no way she could stop now though, especially when she was getting a bit of encouragement from her master. "Ah...it f-feels a little weird...b-but it's not too bad. Do you like it though, Master?"
 
He nodded happily "It feels great. When we do anal, I will let you control it until it no longer hurts" He told her, slapping her ass a bit. "How are you liking it?" He asked her, wanting her to be pleasured too.
 
Elena nodded slightly. It would just have to be part of her training since he seemed to like doing anal, so she was determined to get used to it eventually. She let out a pleasant yelp when he smacked her rear, always enjoying that rough treatment from him. "Mmg...I'm getting used to it still, but it doesn't feel bad at all." she said, managing a little smile.
 
He nodded "if you want to swap to a different hole, I am fine with that" He told her gently, seeing that it still didn't look too fun for her. "Pussy and/or mouth is definitely fine with me" He said, giving her ass another smack. "You love it when I smack your ass, don't you?"
 
It would be the easier choice to switch, but Elena still felt like she should do this for him. It wasn't that she was uncomfortable, but she was not sure how to react to this odd and overwhelming pleasure that came out of this. "P-please, Master. Let me continue..." she said, keeping up her steady pace. "Mmg...ooh..." Elena's back arched a little again, a calmer expression on her face as she seemed to have a good rhythm now. She gasped again as he smacked her ass, getting a little blush from her. "Y-yes, Master. I do love it when you spank me." she said, giving her hips a little wiggle in response.
 
He moaned louder as she wiggled her hips, almost making him want to climax right then. But he held on, continuing the slap her ass and play with her tail. "Of course I will let you continue" He said with a smirk, his finger stroking her cheek when she blushed "No need to get shy here" He told her gently. "You are getting good at this" He smiled. He slid 2 fingers in her pussy and pumped them, wanting her to feel more pleasure.
 
Seeing that he enjoyed how she wiggled her hips, Elena started to do that more often, especially when she had taken his whole length in. The frequent spanks got some nice sounds from her, and having him play with her tail helped her go along with this much easier. "T-thank you, Master. I'm glad to hear that from you." She seemed very happy when he pushed his fingers into her pussy, which made her pace pick up a little suddenly. "Ah...! M-Master! That feels great!"
 
He smirked and moaned at her response, and fingered her quicker, adding a third finger. "Good to hear" He said softly, moaning more as she wiggled her hips again "You are fantastic at this" He said, feeling like he could pass out in pleasure from this, his cock throbbing as it got closer to a climax. "Do you want me to cum in your ass?" He asked her.
 
Elena threw her head back in pleasure when he put the third finger in her, fingering her just as quickly as how she was riding him. She was still glad to hear him praise her like this, even though she wasn't completely confident about this. She felt his cock twitching like crazy in her ass, so she knew he was close. "Mmg...y-yes please, Master. Please mark me there as well."
 
He released, cumming a lot in her ass. As he hole was smaller, a bit of cum spilled out. "That was good" He said, pulling his cock out. He kept fingering her, wanting her to climax too.
 
Elena's mouth hung wide open as her ass was filled up with her master's hot seed, a good deal spilling out and joining the water in running down the drain. She wouldn't have time to relax though, as he was still fingering her. She bucked her hips against them, her body growing hotter as she soon reached her orgasm. "M-Master! I'm cumming!!" Her pussy tightened up on his fingers before she came over them, her entire body shivering with delight until she had calmed down. She stayed there for a little while before slowly lifting herself from his cock, letting more of his seed spill from her ass.
 
He smiled and stood up, helping her to stand "No more fucking for a while" He said "Just need to relax.. I promised you a massage, didn't I?" He asked and turned the water off. He led her out of the bathroom and got a towel, drying her body off with it. He handed it to her "Dry my body off please" He said quietly, smiling as his cock was staying there ready for anything "And feel free to do anything you want with my cock if you want to. But keep in mind I want a massage soon, but I will give you one first" He said
 
Elena moved to her feet with his help, feeling a little wobbly on her feet at first, but she had his support. Still, it showed just how much stamina the inumimi had as she could really keep going, but a break would be good for them both. Once they were out, she let him dry her off, but she had to return the favor. He seemed to be reading her mind about tending to his cock, but she wouldn't go overboard with it. "Yes, Master." She started from the top as she worked her way down, being thorough with drying him off. When she got to his cock, she made sure to dry him off first before she gave it a couple squeezes. She finished up the rest of his body and set the towel aside. "Where will we go for the massage, Master?" she asked. She stood there grooming her tail as it got a little more puffy after being dried off.
 
He smiled and led her to the bedroom. He searched his cupboard and found a padded table, that even had a hole for a head and a hole that was around the groin area (used for his cock for him, and her tail for her). He set it up and then found some massage oil, putting it near the table. "Hop on, I'll do your back first... Do I massage your tail with oil?" He asked her unsurely.
 
Elena watched as he brought out the padded table, and it occurred to her that maybe he was used to having one of his other servants massage him. She was curious about the hole though, and it didn't quite occur to her right away what it would be for. With his direction, she moved onto the table, laying down on her belly and adjusting herself so she would be most comfortable. She wasn't quite sure how to answer that question about her tail as she hadn't used any oil for it. "Er...it might be better to do my tail with your hands first before using the oil on me."
 
(The tail wouldn't go in until I did your stomach)
He smiled and nodded, massaging and rubbing her tail softly and delicately, the fur still wet a bit from the shower. He then got the bottle and squirted oil on her bare back, rubbing and massaging her back firmly. His strong hands went from there to her arms and then to her neck. After that, her ass got massaged, making sure he didn't get any oil on her tail. He finished up by doing her legs and feet. Her entire backside was shiny from the oil, and it got him a little aroused. "Flip" He said, ready to do the front of her body.
 
(Somehow I read that as get on your back...edited.)

Elena sighed softly as he worked on her tail. Even while it was his first time doing such a thing, she was surprised at how good he was at it. He was also gentle enough so she wouldn't be uncomfortable, though it was a little easier with her tail being a little wet still. Once he got started with the oils, she seemed to squirm a little from the touch, as she hadn't had a massage like this before. She enjoyed the whole thing, giggling a couple times especially when he went over her feet and her ass. She then started to turn over, soon realizing that she could slip her tail into the hole there. Once she had done that, she lay down on her back staying flat for him to do her front now. She looked a little anxious, especially when her more sensitive spots were on this side.
 
He smirked and kissed her lips teasingly "Don't worry, I will be gentle." He said. He squirted some more oil on her and started with her shoulders and arms again, then moved to her chest. He rubbed her breasts and nipples slowly with his hands, doing it firmly and thoroughly. He stayed at her breasts, wanting to draw this part out and tease her.
 
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