Ashley’s Anal Curiosity

"Sounds like we have an important mission ahead of us."

"So you're willing to help?"

"Of course I am," Candice replied. "There's no way I'm ever going to miss this."

"Any ideas for what to do?"

"Actually, I have plenty of ideas. I've never told you this, but I'm also a sex therapist, in addition to the relationship advice I give."

"Now isn't the time for jokes."

"I'm deadly serious," Candice said with an undeniable firmness.

It was enough to convince Ashley. "Okay then, how do we start, assuming I get to use your sex advice for free."

"My payment is watching you have a powerful anal orgasm. In other words, I have to be there and participate, okay?"

"You want to play with my asshole?" Ashley asked in disbelief.

"Uh huh."

"Is this some sort of lesbian thing? Or is this purely based on our years of friendship?"

"Both."

Ashley's eyebrows raised. "Okay, this isn't weird at all."

"This is about you, okay? Do you want my help or not?"

Ashley took a breath. "I do."

"Then let's get straight to the point, shall we?"

"Fine. How would you normally proceed with this? I mean, if I were a client, a total stranger, what would you do with me?"

"It depends on what you would allow," Candice replied. "Maybe I would meet with you one-on-one for a crash course on anal. Or maybe I'd do a couples session, where I would assist your husband in claiming your bottom."

"You, me and Rob, at the same time? A threesome?"

"It's a viable option."

"Does it normally work?" Ashley asked.

"Everytime. But I screen carefully though. It has to be the right couple. Only people who are sexually secure with themselves and their relationship. After all, as a sex therapist & counselor, the last thing I want to do is drive a wedge between the couple. Jealousy is a very dangerous thing."

"Interesting."

"Any thoughts so far?"

"Rob has always joked about having a threesome. Plus, I know that he thinks you're very pretty."

"Leaning towards the threesome I see," Candice said playfully.

"Sort of."

"If it makes you feel any better, it's technically not a threesome. Remember, I would be in an assisting role. That means, I would prep your anus for penetration, and Rob would do the rest."

"That actually sounds pretty hot."

"Oh, it is," Candice replied.

"Would you actually be doing anything with Rob though?"

"I won't be fucking him, if that's what you're afraid of."

"Then what?" Ashley asked.

"Like I said, I'll be prepping your anus. I'll lubricate you and begin with some light stretching. Then, to put it bluntly, Rob will fuck you right after."

"Sounds...well...adventurous."

"It is," Candice acknowledged. "But I might have to touch Rob a little bit, if necessary. I'll guide his penis inside of your anus to ensure that it's not too painful. Anal penetration requires a fully erect penis, so if he's not erect enough, I may have to stimulate him in some way. Most likely with my mouth."

"So you'll be giving my husband a blowjob?"

"Only if necessary."

"That's reassuring."

"Hey, you called me. Don't forget it. I'm helping you the only way I know how. Going by my record, I do a good job at this."

Ashley sighed, "Thanks, seriously. I mean it, you're the best."

"Don't thank me yet. You can thank me after your first anal orgasm."

"All of this sounds like the perfect sexual experience for an anniversary. But I'll admit, it's very daunting."

"It always is. And it's not for everyone."

"I'd like to try it," Ashley said. "I'm interested. I really am."

"You have to be absolutely positive, or else we can't go through with it. Our friendship is too important. I would never want to ruin your marriage."

"Then I'll have to ask Rob and see how he'll feel about this."

Candice laughed, "What's Rob going to say? No? Of course he'll be fine with this. He won't be fucking me. He'll be fucking you."

"True, but still, I better call him and see what he thinks."

"I have a better idea."

"Which is?"

"I'll call Rob," Candice said. "I'll work things out with him, then it'll be sort of like a surprise for you. I don't want you to keep stressing over this. The first rule of anal sex is to relax. And that includes mental relaxation."

"That makes sense. So are you going to call him now?"

"Yes, and I'll need one more thing from you."

"What's that?"

"I'll need a picture of what I'm working with," Candice said. "Send me a picture of your bare butt, and a clear picture of your anus. Right now."

"You want me to start sexting at work?"

"It's not sexting," Candice insisted. "It's advance preparation for an important and delicate medical procedure involving your marital health and sexual well-being."

"Candice, it's sexting."

"Call it whatever you want. I need those pictures to determine how to proceed with the anal process."

"In other words, you want to know how small my anus is," Ashley jokingly clarified.

"Exactly."

"Fine," Ashley sighed. "I'll send it in a moment."

"Perfect. In the meantime, I'll give Rob a call to work out the details. I have a great feeling about this."

"So do I. This is by far the kinkiest and craziest thing I've ever done, but for some reason, I think it's going to work."

"That's because I'm an expert in this," Candice reassured.

The two friends said their parting words, and the call ended.

Ashley got off the toilet seat and took a long hard look at herself in the mirror. She had never taken nude pictures of herself before, but if there was ever a good reason to do it, this was it.

She removed her office skirt and panties, placing them on a countertop. She stood only in her buttoned up top and shoes. She was naked from the waist down. Fashionably speaking, it was a very odd combination seeing herself like that, especially in the office bathroom of all places.

After turning around, her butt faced the mirror, and she pointed her phone camera to the mirror also. She took a snapshot of her butt reflection, and it was officially the first nude photo she had ever taken.

Next came the more awkward picture. She thought about how she was going to take a picture of her anus, then came up with the solution. She crouched down and put the phone between her legs, under her body. Once she was in the right position, she took the snapshot.

She stood upright and looked at the picture of her anus. It was the first time seeing it so clearly. She noted the light brown color, shape, and lines of her anus. It definitely looked tiny, and taking Rob's cock in there was going to be a challenge. Luckily Candice knew what to do.

Ashley texted the explicit pictures to Candice, and suddenly the situation was taken to a whole new level.

***

That night, as Ashley and her husband cozied in front of the tv, all she could think about was the anal fucking she would soon receive, and how Rob felt about it.

Even with all the action on Boardwalk Empire, which is Rob's favorite tv show, Ashley kept wondering the same things. Especially since neither Rob nor Candice had mentioned anything. Ashley wondered if Candice had even called Rob or not. There was only one way to find out.

"Did Candice call you earlier today?"

"Yes," Rob said with an unusually coy tone.

"And?"

"And I think you're in for a special treat," he said with a faint smile, which he was clearly trying to hold back.

Ashley was semi-ticked off that she was being left in the dark regarding the outcome of her own bottom. She needed answers, and it was clear that neither Rob nor Candice would be giving any.

"Can you at least give me a preview? What should I expect?"

"I promised I wouldn't say."

"Are you absolutely sure about that?" Ashley said with an over-the-top seductive voice, as if it were going to work.

"I'm absolutely positive."

Ashley made a sexy voice again. "Please, darling? I'll do that thing with my tongue. All you have to do is give me a hint."

"I can wait," he smiled. "Just trust me on this. Candice has something special in store for us."

"You think so?" Ashley replied in her normal voice.

"I am. She gave me several tips over the phone. And she told me what she plans to do with you. I honestly think this is going to add something special to our sex life. Something we've never done before."

It was intriguing to say the least. Deep down, a little jealousy kicked in.

"Are you going to fuck her too?" Ashley asked in a soft feminine tone.

He patted her thigh. "Of course not. Don't be silly."

"Then what's the big secret?"

"You'll find out soon enough," he replied, then pointing to the tv. "You're missing the best parts."

With that, Rob focused his attention back to the tv. Meanwhile, Ashley kept her mental focus on her soon-to-be sore bottom.

Part 3 of 3: Anniversaries & First Times

It was a Saturday morning, which meant that none of them had to go work.

Ashley followed the instructions which Candice had emailed her the night before. The instructions were mainly about cleanliness and beauty.

She took a nice long soapy shower. There was special emphasis on cleaning her anus & rectum. Ashley followed the special instructions in the shower. In fact, she did it twice to be sure.

Following the shower, Ashley sat in front of her dresser mirror with an assortment of beauty products. She took her time making herself look more desirable than she already was. There was equal emphasis on her hair.

By the time she was done, the professional office girl was long gone. It was the new, anal friendly Ashley. And she looked as gorgeous as ever.

She topped off her appearance with matching white bra & panties, followed by a white negligee.

Everything she did was according to Candice's advice in the email.

Speaking of which, the doorbell rang. 10 am. Right on time.

Ashley and Rob went to open the front door together. There stood Candice, the sexually enlightened relationship therapist, with a sassy hair style and two shopping bags.

Candice held up the bags and smiled, "Are we ready to begin?"

Suddenly, what appeared to be an ordinary Saturday morning turned into the beginning of something special.

***

The couple waited anxiously in their bedroom while Candice prepared herself in the bathroom. One of the bags Candice brought was for her special outfit. After all, she couldn't go out in public dressed like she was ready for an anal encounter.

But that raised the question, what was in the other bag? They would find out soon enough.

When the bathroom door opened, both Ashley & Rob were shocked to see Candice's transformation.

Candice's casual clothes were all gone. Instead, she was barefoot in a red negligee, similar to the one that Ashley was wearing. Candice also had her make-up done glamorously, and her hair was styled as well.

"Are we ready?" Candice asked, striking a playfully sexy pose.

Ashley was slightly jealous of her best friend's beauty secrets and fitness routine. She made a mental note to ask for tips later.

"Ready as can be," Ashley said.

Rob agreed.

"The first step is to look the part," Candice said. "We've already done that, obviously, along with the necessary cleaning. Now the next step is for you to get comfortable, and for me to loosen you up."

Ashley felt her pussy twitch.

"I'm ready."

Candice looked around the bedroom. Then she placed a towel on the couple's marital bed, spreading it neatly.

"Before you lay on the bed," Candice said. "You're probably wondering what's in the other bag."

Ashley nodded. "I have a pretty good idea."

"It's the anal kit we'll be using."

"Sounds intimidating."

Candice reached in the bag and held out a small pink dildo. "Not really. It's mostly a few small stuff and plenty of lube. Enough to get you ready for Rob's penetration afterward."

"I'm starting to feel butterflies in my stomach."

"Then we better get started."

Ashley & Rob gave each other a big long hug, followed by a series of kisses to the lips. It was almost like saying 'goodbye.' But actually, it was the welcoming of something new to their relationship.

"Panties off," Candice said.

Ashley reached down and pulled her panties off, tossing them away. She was naked from the waist down, with the thin negligee covering her bottom and pussy, but that wouldn't last very long.

She got on the bed exactly the way Candice had instructed. With her knees on the towel, and her face pressed on the bed. Her butt was up in the air, and she was keenly aware that her asshole & pussy were fully exposed to her best friend and husband.

It was an awkward moment. In many ways, it felt like a visit to the doctor for Ashley. Except instead of a typical gynecological examination, a thorough ass pounding would soon be in her future. But first, there would be the foreplay. Oh god, what kind of foreplay? Ashley thought.

A pair of hands rubbed both of Ashley's bottom. Not just any hands. Soft feminine hands. The kind which only Candice possessed.

Oh god, it's beginning.

"Here comes your surprise," Candice said. "I know you've been bugging Rob about my plans. Well, here it is. I find that a good female rimming is the best way to stimulate anal virgins. Now relax."

Oh god, a rimjob. From Candice?

Before Ashley could say a word, she felt her butt cheeks being spread even further by the soft hands. She knew that her asshole was spread wide open for her husband & Candice to view.

Then came the tongue. Oh god, the tongue. Her little brown anus was being licked by her best friend. Licked up and down. Licked side to side. Licked in all directions. Then came the kisses. Then the licking again. Then a few more kisses to her anus.

Getting a rimjob was never on Ashley's sexual bucket list, but she was so glad she felt it. If she had known it was this good, she would have asked Rob to do it years ago on their wedding night.

Now, here she was, on her knees, face down, getting her asshole licked by her best friend. She had always known that Candice was a very sexual person, and an expert in sexual matters, but this? She couldn't have known that Candice was an expert in perform oral sex on a woman's anus. The technique which Candice was doing was simply too good to be true.

Then came the final piece of the rimjob. Candice's tongue went inside. Oh god, it went in. Ashley felt her anus being slobbered on, saliva running down her ass, and inside the entrance of her rectum.

It tickled a little, but mainly it felt sensational, stimulating nerve endings she hadn't known existed.

"Goodness," Ashley moaned, face down on the bed. "That tongue of yours...my god."

Candice briefly stopped. "It's why I get paid the big bucks."

And with that, Candice continued with her anal licking. Her tongue licking the ring of the anus, followed the entrance to the rectum, then she stopped.

"Are you ready for the next phase of your licking?" Candice asked, still holding the ass apart.

"There's more?" Ashley asked, still face down.

"Yes. Here it comes. Now relax, honey."

Candice said something to Rob, which was so brief and short that Ashley wasn't able to hear it. All she heard was the sound of shuffling. She couldn't see it since her face was on the bed. Sure, she could have simply turned around to look what they were doing, but why bother? She loved surprises, and she was in for a special oral surprise.

The next thing Ashley knew, Rob was eating her cunt from below. Meanwhile, Candice returned to her rimming duties.

Ashley experienced a full oral assault on both her pussy & anus, at the same time, from the people she loved the most.

Her eyes widened and her lips curled while she released a short moan. It was double the oral pleasure. Rob sucked her pussy like never before. Candice picked up her anal licking pace.

Deep down, Ashley cursed herself for never doing this before. Oh well. She was a young 33 year old woman, there would be plenty of time left in her life to continue enjoying double oral sex.

She felt a climax approaching when Rob focused his tongue on her clit. It was exactly the way Ashley liked her pussy eaten. Start at the center, then orgasm with clitoral stimulation.

"Oh god," Ashley groaned, face down, eyes rolling back. "I think I'm getting close."

Candice briefly pulled her tongue away. "Girl, go for it."

With that, Rob continued licking the clit faster, and Candice performed an oral whirlwind inside the virgin anus.

Ashley unleashed an orgasm for the ages.

She screamed out loud and her body tightened. Thank goodness they had recently purchased a home, where they could have some decent privacy. In their old apartment, a scream like Ashley's would have certainly caught the neighbors attention, and maybe the attention of the police.

Now, in the privacy of her own home, Ashley was able to let it all out. Her pussy & asshole received powerful oral stimulation, which resulted in a wet powerful orgasm.

When it was done, Rob moved away from under the pussy, and Candice removed her tongue.

Ashley collapsed on the bed, a wet soaking mess, with a post-orgasm smile on her face.

"Rob was right about you," Candice said, admiring her bare bottomed best friend. "You're quite the cummer."

"Ho..ly...shiiit..." she groaned.

"Girl, now we're only halfway done. They key to good anal sex is lubrication and arousal. I'd say you're more than aroused. And you're nicely lubricated from my saliva. But we still have work to do."

"Still?" she slurred.

"Yes, now back into position you lazy bitch."

Candice gave her best friend a powerful slap on the ass. It was enough to get Ashley back on her knees with her butt in the air.

While her mind was still reeling from the intense orgasm, her face was pressed onto the bedsheet, and she felt her butt cheeks being spread again. This time, the hands were much stronger, which meant that Rob was the one holding Ashley's butt wide open.

Which meant that Candice had both hands free.

Suddenly, Ashley heard the familiar sound of a lube bottle being opened.

Then, Ashley felt the small pink dildo being pushed inside of her butt. It was only a few inches long, but it felt massive inside of her tiny butthole. The pink dildo was pushed in and out.

It was removed, leaving a gaping feeling in Ashley's butt.

Next, something a little bigger was pressed against her hole. Another dildo from Candice's bag. It was pushed harder, entering the virgin hole. As it continued being pushed, Ashley knew that this toy was much longer (and thicker) which gave her a much more stretched feeling.

She felt the ring of her anus and rectum being pushed to its limit. Then, it was held in place there, allowing her anus time to get used to having something that sized in her ass.

Then, the larger dildo was pulled away, leaving a gaping feeling in her delicate asshole.

Suddenly, in the background, there were these sucking/slurping noises. It took a second for Ashley to realize that Candice was probably sucking on Rob's cock, getting him hard and lubricated for the anal fucking. That bitch, Ashley thought.

The sucking noises stopped.

"Happy anniversary, girl," Candice said in a teasing voice.

"Happy anniversary, darling," Rob said.

This time, Ashley felt something else pressed against her asshole. It was hard, yet it had a soft feeling. There was no doubt about it. It was Rob's cock. Her husband was about to fuck her in the ass.

She squeezed the bedsheet and braced herself for what was to come.

Rob pushed. His cock entered. The penetration was slow and gentle. It almost felt like an expert penetrating her, although she wouldn't have known, since she had never been fucked in the ass before.

She then realized that this was from the tips which Candice had given Rob. That was why Rob was able to fuck her ass so easily. And it was also thanks to all the anal stimulation & orgasm which Candice had provided.