Pair of Aces vs. Pair of 10s Pt. 04

Candy had been fascinated with the idea of anal sex for as long as she could remember. She had always wanted to try it, but the sheer size of her husband's cock made it very intimidating. Candy and her high school sweetheart husband, Richard, were both medical professionals so they knew the medical ins and outs of anal sex. However, Richard had resigned himself to being cursed with never being able to have anal sex due to his size. Candy wasn't even sure if she'd like it, therefore it just didn't seem like it'd be worth the effort or risk. Truth be known, a cock like his could put a woman, and her ass especially, in the hospital.

This changed somewhat when a newly made swinger friend finally gave her that experience. Eric and Joy had come over to play for the first time and Candy couldn't help but notice how freely Eric went down on her and rimmed her ass while he was at it. Candy got up the nerve to ask him about it and he proceeded to work her up to her first anal experience. Eric's cock was pleasantly average, aside from having a shamrock tattoo on the head of it. However, he really knew how to use it and it was obvious he had sexed up an ass or two in his day. Eric avoided over doing it on the first outing and left Candy wanting more cock in her ass. That lingering desire fueled her interest.

The next time they all got together Candy asked for it again. Eric took more time with her ass this time, and even introduced her to a butt-plug that Candy had gotten in a random package deal at the local sex shop. In just a couple of sessions Eric had shown her the intense pleasure she could get from her ass. This coupled with the dominant way in which he treated her helped to spark her first true fetish. Soon, Candy had her husband playing with her ass as well. Richard had a lot of fun playing with her little hole, but still didn't think that he'd ever get a real shot at it.

Candy had truly become enamored by the way Eric fucked her ass and was proud that she'd gotten to that point. Not only was she proud that she could do it, it felt amazing as well. While Richard wasn't the jealous type, he did wish he could ease his cock into her backside. Candy also wanted to do this for her husband because she knew that, from an anatomical standpoint, she should be able to fit him inside her. Further, the anatomy of her vagina was such that Richard couldn't fit entirely. Although she loved his girth, she was simply too shallow to allow him to bury that long cock in her. This was troubling for her because she knew that he loved that sensation. Given his reactions when he fully penetrated Joy's pussy, Candy was certain Richard enjoyed that more than he would admit. So began Candy's quest.

****

Candy held the phone to her ear impatiently. Finally, after the second try, Joy picked up.

"Hello." Joy said huskily, juggling the phone a bit.

"Hi, Joy? It's Candy." Candy replied.

"Hey, Candy. What's up?"

"Oh, mostly nothing. I'm a little frustrated though, can I come over and chat?"

"Absolutely! When would you like to?"

"Richard is on rounds all evening, are you busy now?"

"Well, we won't be busy by the time you get here. If you know what I mean?"

"I know exactly what you mean. Sorry to have interrupted." Candy replied, laughing at Joy's subtle reference to sex. "I'll see you in about an hour. Say, four o'clock?"

"Great, I'll finish this up and we'll get some dinner started."

"Thanks, see you then."

"Bye"

Candy put herself together and showed up right on time. She enjoyed the quiet, 45 minute drive out into the mid-western countryside. Eric and Joy were somewhat wealthy and lived out on a private estate. They had a very large house overlooking a private lake. The house itself was at least a half-mile down a private drive, complete with a short bridge over a narrow arm of the lake. While Candy did like her big house in the highlands, a well-to-do sub-division in town, there was something very peaceful about this remote location.

Joy was looking gorgeous as ever as she met Candy in the drive way. She was about 15 years older than Candy but looked younger. Joy apologized for her wet bikini but Candy gave her a hug anyway while wishing she had brought her own bathing suit. Candy had forgotten that they had a pool and hot tub. Candy liked to at look women, and couldn't help but notice how good Joy's tits looked barely hidden under her top. As Joy led the way inside, Candy ran her eyes over Joy's delicious little ass. Joy had muscular legs and ass and liked to give credit for that to Eric. Joy would tell you in all seriousness that she had been kept in shape over the years by putting her legs in the air for Eric.

Candy smiled when Eric appeared in the doorway as they approached. He only had on a pair of swim trunks and his own mischievous smile. His arms and chest were well muscled and made Candy's pussy tingle just looking at him. Even more so than when they first met since she knew what he was capable of. Candy could see Eric looking her over from top to bottom. Candy stood six inches taller than Joy and had a gorgeous, well-proportioned body. With a costume and some face paint she'd look like the quintessential Amazonian woman. Candy had green eyes, fiery red hair, voluptuous breasts that were made for fucking, and a perfectly shaped ass hiding behind her.

"Hey beautiful, it looks like you have lost a little weight. How are you?" Eric complimented Candy as he greeted her, holding out his arms inviting a hug. They held each other in a tight embrace for a moment and one of Eric's hands dropped quickly to give her ass a squeeze.

"I'm good, thanks for letting me come over on short notice. Sorry to interrupt earlier." Candy said as Eric motioned her inside.

"It's no problem. Joy proceeded to get me wound up talking about your ass after you hung up." Eric said with a laugh. "Would you like a drink?"

Candy nodded and Eric grabbed a wine-cooler for her and a beer for himself. They made their way out to the patio where the pool and outdoor kitchen was located. The three of them chatted idly for some time about everyday things like work and the weather. Eventually, Joy's curiosity got the better of her.

"You said you were frustrated earlier, is everything ok?" Joy asked Candy.

"Yes, everything is fine really. I'm just a little frustrated because... Well, I really want to give Richard his first piece of ass and can't. We tried a several nights ago and barely got anywhere. My ass has finally recovered today." Candy said, blushing.

Eric proceeded to quiz her and it appeared as though Candy had relied solely on the confidence gained in their previous encounters. When asked, she said she had been able to give it up for Jake, one of their other friends, but was left sore after that as well. Though at least Jake was able to get off. Candy acknowledged the size differences, with Eric having an average sized dick. Jake was a fair bit longer and thicker, while Richard was by far the largest.

Eric and Joy quickly agreed that in order for Candy to enjoy Richard or Jake in her ass, that she'd have to really work up to it. Conventional wisdom is true in this case, you really have to learn to walk before you can learn to run. Joy shared her own story about how, when she and Eric first tried anal she liked it, but could only do it for 10-15 minutes and would need to rest for several days in between. Joy didn't like the soreness afterward and would only do it once or twice a month. Eric got better at it by being even more gentle and they starting doing it more often. Fast forward twenty-some years and Joy could now handle a thirty minute session every day if she wanted to. Candy carefully considered this for a moment as Eric started the grill.

"So, it sounds like I need to train my ass, correct?" Candy asked slowly.

Joy nodded slowly and looked toward Eric, who had immediately turned around smiling. Joy smiled at him and shook her head.

"What? That sounds like a lot of fun!" Eric said, laughing at his own enthusiasm and Joy's teasing. "Do you need someone to volunteer to be your trainer?"

"I guess so." Candy replied coyly. "I wonder who would be willing to do that for me?"

"Oh! Oh! Pick me! Pick me!" Eric exclaimed, bouncing up and down with his hand raised like a child in a classroom.

Joy and Candy smiled at each other and shrugged, ignoring Eric and feigning ignorance. The ladies couldn't help but laughing at Eric's silliness. If he wasn't so adorable it would have been annoying. He was an obvious choice since he'd introduced Candy to it all and had obviously done some homework on the topic, for Joy's benefit. Candy challenged him by asking what he really knew on the topic. Eric said that he'd be willing to do a little research to be sure, but though that it amounted to two real considerations.

Logically speaking, it seemed like Candy would need to teach her body that she could relax to the point of allowing something as big as Richard's cock in her ass. Then, once she could do that, she'd need to have the endurance to continue the act until satisfaction was found. Candy nodded slowly, thinking about it. She admitted that sounded quite reasonable and wondered how long the process would take. Eric and Joy both shook their heads, unsure. Eric commented that it might make sense to work on the relaxation for size and endurance one at a time. The only thing he was 100% certain of is that she shouldn't push herself to the point of actually injuring herself. Candy, with her background in nursing, readily agreed.

Candy questioned Joy about Eric being her trainer. Candy said she'd like that since she trusted Eric and that he had already been sensitive enough to push Candy's limits without causing any pain during the act, or soreness after the act that was anything more than a good kind of soreness. Joy replied that it would probably be ok, but she'd want to know what the specifics were and so forth. How often would they get together and that sort of thing. Eric offered that Candy would probably need to set goals before everyone could get a feel for how that might work.

Candy thought for a moment, but wasn't quite sure what her goal might be. Soon thereafter Eric announced that the steaks and veggies were almost done. Joy got up to get some place settings and Candy got up and followed her into the kitchen.

"You really wouldn't mind this kind of arrangement?" Candy asked Joy.

"No, I don't think so. I really like you guys and assume that this would mean that I could hang out with your husband more as well. I do enjoy him." Joy replied with a naughty grin. "What does Richard think?"

"Well, we talked about this as a possibility and he's on board. He agreed with you though and thinks he'd enjoy playing with you more often as well. The only problem we could think of is our schedules. Some weeks we aren't home together much."

"I suppose it'd be ok to meet up alone too. Eric and I almost always play together, but we really like you two and I can imagine playing as twosomes and threesomes as well. We've talked about it recently so I know Eric is ok with it."

"What if it's on a daily basis?" Candy asked in earnest.

"I'm not sure I can handle Richard's dick every day, but I'm not too worried about keeping score or anything. Provided that's ok with Richard." Joy said easily.

"I can't handle him daily either." Candy laughed. "That's part of the reason I'd love to give up my ass for him as well."

Joy and Candy reappeared, laughing, and set the table. Eric served the steak along with grilled squash and asparagus. Joy brought out a salad as well. They sat in a comfortable silence for some time while they ate their meals. Joy and Candy both complimented Eric on his grilling skills and idle chit chat started back up. It wasn't long before the subject returned to Candy's derriere.

Candy explained that in her perfect world she'd be able to use her ass on her husband for about thirty minutes every day if she wanted. So that should be her goal. Candy also felt that she should shoot for stamina first, and work her way up to being able to have Eric really fuck her ass for thirty minutes or more every day. Joy smiled and commented that it was a lofty goal, but it could be done. Candy went on to say that she was less certain about how to teach her rear end to accept something as big as her husband's cock.

Eric suggested that he could probably help in that area. He'd read several articles over the years that detailed how a person would train themselves to do this with a select variety of toys, ranging in size from small to as large as the person cared to go. He'd been to a local sex shop recently and remembered seeing some extremely large toys meant to do just that.

"Do you know roughly how big Richard is?" Eric asked Candy.

"He's just a touch shorter than 10" long and 6.5" around." Candy replied as a matter of fact.

"Wow! That sounds pretty exact." Joy said, her pussy tingling. "How do you know?"

"Well, Richard and his brother made a bet a few months ago. They had to measure exactly to settle the bet." Candy said, laughing about their foolishness.

Eric bumped Joy's arm and winked at her. He already knew that she was imagining the brothers and two fists full of thick cock. Joy squeezed her legs together and smiled back at Eric. Candy noticed Joy squirming and reached over slowly to pinch Joy's hardening nipples.

"You want those fat cocks inside you, don't you?" Candy said seductively, leaning in to kiss Joy's ear and neck. "You want to get your holes filled up."

"Oh yea." Joy whispered back.

"I can't wait for you to come over so I can show you how much I appreciate you letting me borrow your husband's cock. I look forward to eating your pussy while you get worked with that long dick." Candy said teasingly.

Joy sighed as Eric reached in to touch her thigh, trailing his fingers up to her crotch. Candy touched her other thigh similarly. Eric and Candy were both kissing Joy and touching her. Joy was enjoying the moment and didn't stop Eric when he unfastened her bikini top. Candy and Eric suckled at Joy's breasts and took turns slipping their fingers under her bikini bottoms and touching her pussy gently. Eric held her bathing suit to the side and spread her pussy while Candy fingered her and fiddled with her clit. Joy moaned and held their heads to her tits. They went on teasing and pleasuring her in this way for some time. Joy moved her hips and breathed heavily, enjoying the treatment.

"Come here, babe. Sit on this." Eric instructed as he stood and dropped his shorts.

Eric sat back down on his chair and stroked his hard cock. Joy smiled and stood, dropping her own bottoms. With her back to him, she eased her pussy over his cock, working her favorite dick into her slowly. Joy quickly buried his length into her and leaned back against him. Candy dropped a chair cushion in front of their chair and kissed the inside of Joy's thighs from her knees to her crotch. Candy licked from the base of Eric's balls to Joy's clit and began whipping her tongue across it. Candy liked to eat pussy and, over time, had found just what Joy liked. Eric pumped slowly while Candy lavished Joy's pussy with attention. Joy held her legs apart allowing Eric's cock to drive into her. She hunched her hips while Candy rubbed her face in her pussy. On and on they went while the pleasure swept over Joy's body. Joy's breathing increased and started to become ragged as Candy focused on her clit. Joy started whining and held Candy's face to her snatch. Joy felt electricity inside her as her orgasm drew close and humped Candy's face hard. Joy cried out and shook hard, gushing her girl cum over Eric's cock and balls. After a moment, Joy let down her legs and sat up just a little while catching her breath. Candy sat back in her chair and used a napkin to wipe her smiling face.

"Do you want to cum, baby?" Joy asked Eric.

"That depends. Candy, do you want your first lesson tonight?" Eric replied.

"Yes, very much." Candy replied.

"How about I save it for her ass? Is that ok?" Eric asked Joy.

"Of course. There's nothing quite like a cock throbbing in your ass." Joy stated with authority. Joy wiggled her hips, grinding herself on Eric's still rigid dick. She slowly stood up, turned and stroked him with her hand for a moment while she kissed him. "I'll coach you next time while I watch you use her ass, how does that sound?"

"Great!" Eric and Candy said at the same time before laughing together.

"Good, I'm already late for a wedding." Joy said as she gathered her bikini and headed inside.

When asked, Eric explained that they owned a wedding venue that Joy managed. It was a family business that she still enjoyed maintaining and she liked to stop by on the weekends to make sure that customers were satisfied and that staff were doing what they needed to do. By the time he was done explaining, his erection had begun to whither. Candy looked at his crotch and frowned. Eric smiled back and remarked that she shouldn't worry since it'd take less than a minute to be ready to go again. Eric asked Candy if she'd like to go for a swim in the pool. She complained that she didn't have a suit, but it didn't take much convincing for her to agree to strip nude for a dip in the pool.

As they were about to get in Joy reappeared looking gorgeous in a skirt and top that showed her ample cleavage. Joy smiled broadly and waved a bottle of lube at the two of them before placing it on the table. Joy said her good byes and instructed Candy and Eric to have fun before she turned and departed. Eric grabbed Candy's hand and led her to the pool. They both slid in and enjoyed the feeling of the cool water surrounding their bare bodies. They waded near each other and chatted idly at first. It wasn't long before they drifted close together and became a little more intimate.

"So, how do you want to approach this?" Eric asked.

"What do you mean, you just stick your dick in my ass, right?" Candy replied glibly.

"No, silly. What I mean is, should we start off with like 15 minutes and go from there, or what?"

"I don't think so. I'd rather make better use of our time. I know you can bang my ass for over an hour and I'll be fine. Sore for a couple of days, but fine. So I'm thinking you do me for 30 minutes today and the next day I'm ready again we'll go thirty more. We'll repeat this until I've got your dick in my ass every day. How's that sound?" Candy said. She had gotten close and turned her back, rubbing her ass against Eric's crotch.

"I like you way you think. I'd say at first we should take it easy and just work your ass. Later, once its daily maybe we can start being a little rougher?" Eric replied, reaching around to massage Candy's big tits.

"Yes, definitely. I can't wait. It'll be nice to have you pounding my ass every day. You know, if we go over 30 minutes that might be ok."

"I agree, but not until you've mastered your 30 minutes per day. What's your favorite position?" Eric asked, before kissing her shoulders gently.

"Mmm. I like facing you, so I can see the look on your face."

"Me too because it's I like to be sure that you're enjoying yourself. We'll concentrate on that, but we should experiment will all the positions we can think of. You might find a new favorite or discover positions that you should avoid."

"Mmmmhmmm."

Eric was hard again from Candy's teasing. She ran his hard cock up and down the crack of her ass. Eric was reaching around playing with her tits and pussy while she leaned back against him. She was taller than he was which means she had to spread her legs a little to lower herself. This made accessing her perfect. Candy responded strongly when he touched her clit.

"C'mon, let's shower off. I'm getting anxious to feel you cum with your ass full of cock." Eric teased.