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Part 1 of 3: The Anniversary Surprise

They were best friends in high school. And they remained best friends ever since.

Even as they were adults living in the big city, with their own careers and their own busy lives, they still made time to meet at least once a week at a downtown cafe, where they shared updates on their lives.

They were still dressed in their office clothes as they made conversation over coffee.

“So, my 5 year anniversary is coming up,” Ashley said, referring to her marriage to Rob.

Candice sharpened her gaze. “You know, 5 years is a big deal, especially nowadays. You know what that means, don’t you?”


“It means you’ll have to get him something extra special this time, and vice versa too.”

Of course, Candice was the authority on this. She worked for a dating website and was a professional matchmaker. She was also a relationship therapist and a marriage counselor.

No matter how dubious Candice’s career seemed to Ashley, there was no doubt that it was effective. Candice had a great reputation for bringing people together and making difficult relationships work. In the big city where they lived, people were more than willing to pay Candice big bucks for her guidance.

“At this point, it’s tough to get something nice for Rob,” Ashley complained. “He’s a low key person and he already has everything he wants.”

“Then do something special. Cook him a great meal. Throw him a surprise party. Anything.”

“Unfortunately, Rob is a far superior cook than I am. And he hates surprise parties. He thinks they’re childish.”

“Good sex always works,” Candice said in a joking manner, taking a sip of her coffee. “Men always appreciate a good blowjob whenever possible.”

Ashley blushed, “Goodness, keep it down, would you?”

“Look, all I’m saying is that 5 years is a big freaking deal. Especially these days. You might want to think of something special.”

“You’re right.”

“I’m always right,” Candice winked.


The advice itself wasn’t bad. Ashley thought about it on the way home. As she undressed in her bedroom, she realized what a lucky woman she was.

She was married to a great guy, she had a great job, and she had a wonderful group of friends to rely on. At 33 years old, she was doing well.

But what was she going to give Rob for their 5th anniversary? He already had everything he wanted. He wasn’t a picky guy. He was simple in his taste. He worked as an insurance salesman, and in his free time, he enjoyed sports and hanging out with his buddies. That was it.

Normally, Ashley loved the fact that he was so low maintenance, because it gave him more time to focus on her needs instead.

Now, more than ever, she wanted to make things about him. She wanted to please him. And she was determined to make their marriage last.

She looked in the bedroom mirror. She still kept herself in decent shape. She was an athlete in high school & college, but since becoming an office girl, it was harder to maintain the same form. She’d put on a few pounds around her hips and thighs. Most people wouldn’t have noticed it, but she was always self-conscious about her appearance, and kept track of every change her body made.

Time to cut a few carbs, she thought.

Otherwise, she looked great.

She slipped into her comfortable and casual home clothes- sweatpants and a large tshirt. With the big anniversary coming up, it was time to be a good housewife and prepare dinner.


Work was interesting the next day. Ashley worked for a mid-sized advertising agency, where she got to do a job she loved. She loved collaborating with her colleagues and being creative.

But in the back of her mind, all she could think about was her upcoming anniversary, and the conversation she’d had with Candice.

With everything being ahead of schedule in the office, Ashley used her break time to go to the private bathroom to call her best friend. The free relationship advice was always welcome.

After all, if Ashley was right, she knew that Rob must have been planning something special on his own. It was easy to do something special for Ashley. She had plenty of things she enjoyed, including- surprise parties, fancy dinners, and of course, expensive jewelry.

Anniversary gifts were something Rob never forgot about. Each year, he made sure to get her something very nice. Each year, he always managed to outdo the previous year’s gift, which was why Ashley had to come up with something extra special.

She went inside the bathroom and made the call using her speed dial. Thankfully, Candice had free time as well, and they chatted briefly before getting straight to the point.

“I think you’re right,” Ashley said, sitting in the bathroom stall with the phone in hand. “Something romantic is probably the best idea.”

“Now you’re getting it. Good for you.”

“The problem is that I don’t have any ideas.”

“How about sexy outfits? You know, lingerie, see-through bra and panties, that sort of thing.”

“Rob wouldn’t be into güvenilir bahis that,” Ashley replied. “Everytime I buy something sexy, he wants me to remove it as fast as possible. He just likes the nudity.”

“How about role play? There are plenty of hot scenarios out there.”

“Too tacky.”

“Oral sex?” Candice asked. “Where are you with that?”

“No troubles there.”

“Do you swallow?”

“It’s practically a habit,” Ashley replied with a hint of embarrassment. “There’s the problem, it seems like we’ve covered all the bases.”

“What about anal sex?”

The question stopped Ashley cold. She was dumbfounded for a moment and in a state of slight disbelief. Anal sex? Was that really the answer? Candice was the expert and she mentioned it for a reason.

“We’ve never done that,” Ashley replied.

There must have been something about Ashley’s response, because the tone of her voice caught Candice’s attention.

After all, Candice was a woman who specialized in dating, relationships, and sex. She made a successful career out of it, which not many people can.

“Have you ever experimented with anal before?” Candice asked in a suggestive tone. “I mean, without Rob. Have you done it with past partners before?”

As best friends, Ashley & Candice have discussed their sex lives before, of course, but never in such detail. The level of specifics was beginning to make Ashley feel uncomfortable, but she couldn’t complain. After all, she was the one who called for the free advice.

“I’ve never had anal sex before.”

“Not even a finger?”

“I’ve had a finger,” Ashley admitted. “Nothing more.”

“Really? When?”

“Some guy I briefly dated in college?”

Candice became intrigued. “Really, college? Who was it? Mark? Dave?”

“That’s not important right now,” Ashley replied, shaking her head. “The important thing is me and Rob.”

“I think we’ve found your answer.”

“Anal sex?”


“Sex in my butt?” Ashley asked again for confirmation.

“That’s pretty much the same thing.”

“And how’s that supposed to work for our anniversary? Should I just spread my butt open and tell him it’s time to fuck?”

“That’s a good start.”

“I was being sarcastic,” Ashley sighed.

“Well it was a good idea nonetheless.”

“I’m being serious, Candice.”

“So am I. This doesn’t have to be rocket science. Men love sex. Sometimes, it’s that simple. Wear some sexy lingerie, give him a hot blowjob, and offer your anal virginity. I guarantee Rob will fall in love with you all over again. Heck, he might even marry you again.”

Ashley was quiet for a moment. Her best friend had a point, no matter how lewd it seemed to be.

“I’ll think about it,” Ashley said.

“There’s something you still haven’t told me.”

“What’s that?”

“Has Rob ever asked for anal sex?”

“Never,” Ashley replied.

“Do you think he wants it? I mean, has he ever massaged your butt? Does he compliment your bottom? Does he look at your butt at all?”

“Yes, to all of the above. Do you think that’s a sign that he secretly wants to have butt sex with me?”

“It could be,” Candice said. “Maybe he wants it, but he’s too shy to ask.”

“I don’t know. If Rob wanted anal, he would have asked.”

“Maybe he doesn’t want to freak you out. Or he’s afraid that you might think he’s some sort of pervert.”

Ashley nodded. “Maybe.”

“Now for the final question, which you haven’t mentioned either.”

“What’s that?”

“Have you ever fantasized about anal sex before?”

God, it was a good question. One that Ashley instantly knew the answer to, although she was slightly embarrassed to discuss it, even with her best friend of all people.

“Sure I have,” Ashely admitted. “Not recently. But it’s crossed my mind. I think it’s crossed every girl’s mind at some point.”

“Then what’s been stopping you all these years?”

“What do you think?”

“Tell me.”

“It’s not complicated,” Ashley replied. “To put it bluntly, cocks are large, assholes are small. In my case, tiny. It’s that simple. That’s why I’ve ever taken the plunge. I’m not made of rubber. I’m a human being.”

“Honey, lots of women these days have butt sex. And lots of women enjoy it, a lot.”

“Including you?”

“Definitely me.”

Ashley smiled, “Figures.”


“You seem like the anal sex type. No offense.”

“None taken,” Candice replied. “The pain is worth the orgasm.”

“Does it really feel that good?”

“I could tell you. Or you could experience it yourself, on your anniversary with Rob.”

Ashley paused for a moment. “How will I know if this is right for me?”

“There’s only one way to find out- ask him.”


That night. With their anniversary only a few days away, Ashley tried her hardest to be the perfect wife.

She wore a nice dress and cooked dinner from a recipe she had learned online. Naturally, the food didn’t turn out very well, but at least she tried.

After relaxing on the couch in front türkçe bahis of the tv, it was finally time for bed.

They kissed passionately and Ashley unzipped the back of her dress. As they prepared to make love, the topic of anal sex was continuously on her mind. It was all she could think of while they kissed.

She didn’t want to spoil the surprise, but she couldn’t help it either. She just had to know if Rob would think it’s a good idea or not. The worst case scenario would be to offer anal sex on their anniversary night, only for him to be disgusted. Then it would be too late. The night would be ruined.

So she had to ask now. She ended the kiss and looked her husband straight in the eyes.

“I’ve been thinking,” she said. “Our 5th anniversary is coming up, as you probably already knew.”

“How could I forget?”

“Then why not do something special?”

Rob smiled, “Anything in mind?”

It was the moment of truth, and she tried to appear as confident as possible when she made the proposal.

“Do you want to try anal sex on our anniversary night?”

Her eyes were locked to her husband’s face, waiting for any sign of reaction so she could analyze it. She wanted to know his every thought and his openness to a new sexual adventure.

Sure enough, through the subtle shifts on Rob’s face, it appeared he was interested in the idea, and Ashley felt a strange sense of relief, like she had found the perfect gift for their anniversary.

“Anal huh? That sounds interesting. Have you done this before?”

She shook her head. “Nope, never have.”

“Has this been something you’ve wanted for a while?”

“Long story,” she replied. “But kind of.”

He continued smiling, “Why wait? You look gorgeous in that red dress and we’re both in the mood. Why don’t we do it now?”


Shit, she thought.

She wasn’t mentally or physically prepared. But what’s the problem? If Candice could do it so easily, so could Ashley. As Candice had mentioned, plenty of women do it nowadays.

It was time to stop being a wimp and finally lose her anal virginity.

“I’ll get the vaseline,” she said with a sense of self-defiance.

“Are you sure you want to do this? You look so…uneasy.”

“I’m fine. Believe me, I’m fine.”

He rubbed her shoulders. “I’m okay with, you know, regular sex. We don’t have to do this if you’re not comfortable.”

Ashley took a step back and dropped her red dress to the floor.

“I’m serious. I’m fine.”

She was almost in a robotic mode as she grabbed a small container of nearby vaseline and handed it to her husband. Then she pulled her panties down and bent over the bed.

The mood suddenly felt cold & unromantic, like she was in a doctor’s office preparing for a prostate exam. While she waited in the bent over position, she realized that her husband must have been dumbstruck by the awkwardness, and that she’d forgotten to be seductive about their first anal adventure.

But it didn’t matter anymore. Rob had the lube. And her bare ass was pointed outward, ready to go.

The sound of the vaseline cap opening made her more nervous than she’d expected. Deep down, she felt the same nerves she did when she lost her virginity. And in many ways, it was the same thing. She was losing her virginity again, except this time, it was the virginity in her ass.

A shock went up her spine when she felt Rob’s vaseline covered index finger push inside her ass.

“Yikes!” she gasped.

Rob’s finger immediately pulled away from her butt.

“Are you okay?”

“I’m fine.”

“Do you want to keep going?” he asked.

“Of course I do.”

Rob tried again, this time a little more gently. He pushed his index finger back in her butt, and it was the most uncomfortable sexual feeling Ashley had ever felt.

It was so unnatural and awkward having a lubed finger in her butt. Worse, it just felt unsexy.

When Rob pushed his finger all the way in, Ashley’s toes curled on the carpet floor and her body tensed.

“Take it out,” she ordered.

Rob pulled his finger away and gave his wife a concerned look, as she stood upright.

“This was probably a bad idea,” he said.

“No, it’s a decent idea. It’s just, I’m not prepared for it right now. That’s all. We can try again later, on our anniversary night.”

Rob looked confused. “You want to try that again?”

“Why? You don’t like it?”

“I don’t know. We haven’t even done it. But you look so uncomfortable when my finger was in your butt.”

For some reason, that only made Ashley feel more determined to have anal sex with her husband. Maybe it was because it would be the first time for both of them. It would be like losing their virginities together. His cock in her butt. What a romantic thought, in a very odd way.

“Then it’s settled,” she smiled. “Anal sex on our anniversary night.”

“I’m serious, Ashe, we don’t have to do this.”

“And I’m serious too. We’re doing this. I just need a little more time. In the meantime, let’s make love the proper güvenilir bahis siteleri way.”

They held each other and kissed.

Ashley was disappointed with herself that she couldn’t go through with it. She considered herself to be a strong career-minded woman who could overcome any obstacle, but anal? That was something out of her realm.

She definitely didn’t want to rely on Rob either, because that could be dangerous. There was no way she was going to trust her delicate little anus to an inexperienced man with a semi-large cock. That was out of the question.

No. What she needed was an expert. Someone who’d know what to do in a critical situation like this.

Luckily, she knew just who to call.

Part 2 of 3: The Sexually Enlightened Best Friend

The next day in the office, Ashley’s mind was consumed with her sex life. All she could think about was sex. And whether she could actually go through with taking it up the butt.

While she was at her desk, she texted her sexually enlightened best friend. When Candice was free to chat on the phone, Ashley headed to the bathroom for a quick moment of privacy.

After making the call and sitting on the toilet seat cover, Ashley spilled all of the details. She told Candice about the brief conversation with Rob, his willingness, and the finger that went inside her butt. She told Candice about all of her feelings regarding the personal matter.

“I don’t see how a normal woman could handle that?” Ashley wondered.

“It’s 2016, honey, plenty of women are into that.”

“I’m sure it’s just to please the guy.”

“Hang on,” Candice said. “Let me send you a link. Watch it, then call me back.”

“Is it porn?” Ashley asked, knowing her best friend.

“Actually, it is.”

“Is it going to put a virus in my phone or something?”

“Doubtful. I look at that porn site all the time on my phone, while I’m supposed to be working, and my phone is just fine.”

Ashley sighed, “Send it over.”

“Call me back when you’re done watching.”

Ashley waited for the link. It was boring and lonely sitting in the bathroom stall waiting for a porn link. It was a sad reflection on the state of her personal life.

Finally, three links arrived.

Ashley opened the first one, which was a link to a porn site. The video was a brief professionally done clip which showed a woman being plowed in her anus by a huge cock. She fast forwarded through it, watching only the main parts.

The second video had the same content.

The third video was much the same.

She felt a slight embarrassment sitting in the bathroom stall, in her office attire, watching porn on her phone, when she was supposed to be working. She used to complain when men did it, now she was doing the same thing. At least she had a legitimate reason for it, she thought.

After skimming through those porn clips, she called back Candice.

“What did you think?” Candice asked when answering the call.

“I meant normal women. These are porn stars.”

“What’s the difference?”

“Porn stars are performers,” Ashley explained. “They’re made for sex. It’s all they do. And they can spend all day getting in shape and preparing for sex. I’m an office employee. It’s different.”

“Fine. Hold on. Call me back in a few minutes. Let me show you something else first.”

“Wait…hang on…”

The call ended and Ashley sighed. She waited patiently, finally two links arrived from Candice.

Ashley clicked on the first. It was from the same porn site, except this time, it featured a normal couple instead of porn stars. Ashley watched as a plain looking housewife was receiving anal sex in her bedroom, by a man presumably her husband.

The next video was similar. It featured a plain (slightly nerdy) looking college student having an anal orgasm, courtesy of a guy from the college football team.

Ashley was no stranger to porn. She’s watched softcore stuff on cable with her husband. Occasionally, they would watch hardcore porn by ordering it on-demand to spice up their sex life.

But she had never watched amateur porn before. It was odd watching “normal” people fuck. It was like being a voyeur into their sex lives. It was even more surreal watching the videos of those “normal” women having anal sex, and absolutely loving it.

Ashley understood the point of the videos and called her friend back.

“Okay, I get it,” Ashley said. “Normal women can do it too.”

“And you’re a normal woman, right?”

“Last time I checked.”

“Then why can’t you do it?”

Ashley sighed, “I don’t have a clue.”

“Sorry for sounding like a condescending bitch. Honestly, at this point, Rob is probably right. Maybe try something else? Ask him if he has any other fetishes. There’s gotta be something.”

“I’d rather stick with the whole anal thing.”

Candice’s relationship sense kicked in. “Really. Why is that? Now I’m starting to think that a part of you is actually looking forward to this, no matter how hard you try to fight it.”

“I think it’s hot. My guess is, Rob thinks it’s hot too. And frankly, I’m a little curious. I’ve always been sort of curious. It’s the one part of my body which I haven’t explored sexually. So it would be nice to kind of see what the fuss is about.”

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