How to Have Anal Sex

"CJ wants us to meet," he said.

"I knew it! I freaking knew it."

"And she wants to include pictures of you in the e-book."

"You mean pictures of my naked ass?" Morgan clarified. "And pictures of my anus? And most likely, pictures of your dick inside my asshole, if I understand this whole thing correctly."

"Yes, yes, and yes."

"Jesus, with friends like this, who needs enemies?"

"Hear me out," he said with a confident persistence. "The only reason she asked me to call you is because we just finished our first session together. It turned out great and she's over the moon, so to speak."

"In other words, you just finished fucking her in the ass. You should know that women are in a different state-of-mind after an orgasm. Pardon my friend for talking crazy."

"As an MD, your friend's mental state seems perfectly fine. She's told me about many of your past conversations regarding sex, which includes your interest, or curiosity, in terms of anal matters."

Morgan suppressed a gasp. She didn't know what was worse, the betrayal by her friend, or the fact that this stranger now knew her name, address, phone number, and sexual history.

But, maybe it was a good thing. As lifelong friends, their taste in men and sex had always been similar. They lost their virginities the same year. They both had sex with roughly the same number of guys. And they shared sex toys, which was their most highly guarded secret as friends. Morgan was certain that CJ hadn't told the doctor about that.

Most importantly, they shared long conversations about anal sex, which usually led to debates about whether female porn stars enjoyed it or not.

In the end, they both gave up on the fantasy. Each of them tried it with their respective ex-boyfriends. Both of them were left with unsatisfied desires and sore assholes.

Now if CJ viewed this guy as a mentor, why not Morgan? Good luck should be shared. She deserved to have anal sex with an experienced person and formulate a definitive opinion as to whether she enjoyed it or not.

"Hypothetically, how would this work?" Morgan asked tepidly. "Let me rephrase that. What aspect of your job qualifies you as an expert on anal sex? I'd imagine your erection is much bigger than your probing index finger."

He laughed. "Obviously, I'm a doctor. Sometimes patients come to me because of rectal issues, which require examination and diagnosis. I also perform rectal exams with my finger. If needed, I'll do a procedure known as anoscopy. That involves inserting a white bullet shaped probe into the anus. The center can then be removed, leaving the patient with a hollow tube in their rectum. Sorry for getting technical."

"Hmmm...."

"In layman's terms, I'm experienced with anal insertion," he said. "The anal cavity has a great number of nerve endings. In fact, some people consider the rectum to be the holder of a "sixth sense." It's exquisitely sensitive and can differentiate hot from cold. It can also sense pleasure and pain."

"Wow, I had no idea my butt was so complicated." Morgan was truly impressed.

"I can assure you, it will be pleasurable beyond your wildest expectations."

Morgan asked the question that was burning in her mind, "Is... well... is it safe to put a large penis in such a small hole? Isn't it supposed to be a one way door?"

"Morgan, anal sex has been practiced for millennia. If care is taken, it's a perfectly safe and incredibly enjoyable activity. Believe me. I spend all day, every day, looking at assholes, including many that have been on the receiving end of anal sex. My patients are candid with me because they often seek medical counsel before experimenting with their partners. When done correctly, the rectum is left in perfect condition."

Without hesitation, Morgan asked her final question. "Is it really possible to have anal orgasms? Do they feel different from regular orgasms?"

"Many women have anal orgasms and do report that they feel different from vaginal orgasms. Try asking CJ about that."

There was another pause on the line as Morgan took a moment to think. She understood what CJ liked about this guy. But still, her anus was the most intimate of areas and she always had a fear of her sex life being made public. In her line of work, that type of exposure could really be a problem.

"I'd have to respectfully decline," Morgan stated, though there was a sense of regret in her voice, as if she had to convince herself.

There was yet another brief pause on the line as Richard processed her words and wondered how firm the refusal was.

"I understand," he replied. "I won't hassle you about it. I'm not that kind of guy. The last thing I'd want is to drive a wedge between friends and roommates. Do you still want to be an editor for the book though? It'll be a fun way for the three of us to work together."

"Really?"

"Why not? It would be great if you helped sharpen my writing skills and added a female perspective to the topic. I'll pay you, let's say, $300 dollars for your efforts. If the project is successful, I'll compensate your fairly."

It only took a moment for Morgan to weigh his offer.

"You have yourself a deal," she said. "Believe it or not, I'm actually open minded when it comes to sex. Really, I'm not the prude that I seem to be. It's just that I'm really discreet about my sexual habits."

"Well, as an MD, I can assure you that I'm also discreet."

At that point, Morgan knew where things were headed. She was sure it wouldn't end with book editing.

*

It was 7:13 by the time Morgan arrived home. She smelled freshly cooked stir fry as she walked in and heard the sound of news pundits discussing politics on tv in the background.

After closing the door and taking off her shoes, she marched straight into the living room to find CJ on the couch. She was dressed in nothing but a loose t-shirt, legs curled under her with way too much thigh showing.

Morgan wondered if CJ was wearing panties below the t-shirt, or nothing at all.

"Dinner's ready," CJ said with an overly polite smile.

"You gave him my phone number!"

CJ flashed a wider smile. "He texted me a while ago and said you accepted his job offer. You see, things are working out well."

"I'm finally at a loss for words."

CJ adjusted her smile in an attempt to look even cuter. "Are you mad at me?"

"No. I'm not. Should I be?"

"Of course not! I've actually visited his office and he gave me a brief tour of the hospital. Everything is legit. And the sex..."

There was a gleam in CJ's eyes as her voice trailed off into space.

"Amazing, I'm sure."

CJ nodded. "That's why I had him call you. I knew you'd never fully trust me, but if you spoke to him directly, you'd know everything checks out."

"Well, I have to admit that he seems like a personable guy. I like him."

"Are you really going to help edit his book?"

"Why not?" Morgan replied. "Sex doesn't bother me."

"Unless it's happening in your asshole."

"You seem fixated on my rectal area. It's almost like you have an unhealthy obsession with it."

CJ winked. "We share everything. And I hate the idea of exploring new pleasures without you."

"Be my guest, really."

"What if I won a million dollars in the lottery? Would you be okay if I didn't share anything with you?"

Morgan immediately answered. "You've got me there. No, I wouldn't be okay with that. I'd expect you to share."

"How is this any different? We've got a guy who is a master of butts and knows all the tips and tricks. Just think, whoever you date in the future will never cheat on you. You'd be a true sexpert in all areas. I mean, every guy secretly craves having anal sex with a woman."

"CJ, we both know that sex is about sharing pleasure. It's not enough that the guy likes it. I have to like it too."

"My point exactly," CJ clarified. "How do you know you don't like if you haven't fully explored it?"

"You raise a compelling point. I'm just going to come right out and ask, though. Did you have an anal orgasm when he fucked your ass?"

"Morgan, I swear to you I had several anal orgasms. They were amazing. The rim of my ass was super sensitive from his foreplay. Then after he was all the way in, the push and pull of his dick sent me over the edge. I've never felt anything like it. My ass exploded in pleasure. Let's have dinner and we'll keep talking about it."

CJ uncurled her legs and turned off the tv. When she stood, Morgan's suspicion was confirmed. There were no panties underneath that long tshirt.

***

The girls worked on their tans again the following morning. They both donned their bikini tops, though CJ went bottomless in another effort to erase her tan lines.

Meanwhile, Morgan laid on her stomach, with her iPad propped up in front of her. A rough draft of the e-book was on the screen. The book was incomplete but already had a lot of writing and instructional tips included.

Even more striking, there were pictures of CJ's butt, her anus, a lubricated finger inserted inside her rectum, and a few pictures of the doctor's cock sodomizing her.

"Jesus," Morgan gasped.

CJ turned to her friend. "I'm assuming you're on page 52."

"Page 50, actually."

"On page 52 there's a picture of my ass with cum leaking out of it."

"Thanks for the spoilers."

"It's my butthole, not the Game of Thrones ending," CJ pointed out. "Anyway, what do you think so far?"

"There are a few typos which I've fixed. I'll clean up some of the writing later. A few parts seem stiff and too medical in their phrasing."

"I'm not talking about grammar. You know exactly what I'm asking."

Morgan gulped. "Going by the pictures, it looked effortless. And his instructions for anal insertion seemed logical."

"Trust me, it was as effortless as it looked. If a cock that size can slide into my ass and feel good, it would definitely feel good for you too. Especially since my butt is thin, and your butt is a little plumper."

"Since when was butt size an indicator of rectal tightness?"

"I mean that as a compliment. You have a fantastic set of legs and a great ass."

"One thing's for sure," Morgan said, looking back at the screen. "This guy knows what he's doing."

"Medical school serves an important purpose."

"I don't think that's what they had in mind."

CJ's phone beeped and she checked her text. She giggled like a schoolgirl and spread her legs while twirling her feet in the air.

"He can see us," CJ said.

"The doctor?!"

CJ texted quickly. "Yep, he's between patients and enjoying the view. I asked if he can see my asshole, he said no...hold on ... I told him he should be able to, given how much he stretched it yesterday ... he replied with an 'LOL' in return."

"Dr. Creepy is making his return. Whatever goodwill he earned yesterday is diminishing."

"Girl, the only goodwill that matters is the content of that e-book in front of you. He wants to wrap up all his research and content gathering by next month. Then he leaves for a medical conference. So time is of the essence."

Morgan sighed, looking at the anal pictures. "I'll have to think about it."

"You do that. And if you decide to give it a try, I have the ideal setting."

"Which is?"

CJ smiled. "We make a surprise trip to his exam room for an appointment. He could fuck you in there."

"Jeez."

"Do you know how HOT that fantasy is? Women would kill to be fucked by a sexy doctor in his office. It's a legit fetish."

"I won't lie, that does sound like a sexy scenario for..."

CJ's phone beeped, interrupting their conversation.

"I have to take this call inside," CJ said, sitting upright. "It's a lawyer I'm working with and I need to give her an update. Hi Jane... Yes ... Yes ... I'll check on it now. It should be finished by tomorrow."

CJ's went back inside the house to continue the call, leaving Morgan alone to tan in silence.

But was she really alone? Morgan wondered if Dr. Dreamy was still watching their backyard. Surprisingly, Morgan was enticed by that thought, especially as she looked at pictures of CJ's asshole being sodomized.

Almost instinctively, Morgan slid off her bikini bottom. Now naked from the waist down, her tan-lined butt was on display. Then, she spread her legs and exposed her asshole to the sunlight for the very first time in her life. Just like CJ had done moments ago, she twirled her feet in the air.

But unlike CJ, her right hand slowly drifted down to her wet pussy, and she began to rub. She wondered if the doctor was still watching. If so, was she making him hard?

***

Days later. They wore similarly styled sun dresses as they stood side by side, looking in the bathroom mirror at the hospital. Morgan had butterflies in her stomach.

"Trust me, the key is relaxation," CJ said.

Morgan kept needlessly adjusting her skirt. "Easy for you to say."

"It is easy for me to say. I've done this with him already. Three times, in fact."

"Two other times? Why am I finding out about this now?"

CJ shrugged. "I didn't want to taunt you. Or make you jealous."

"Now I feel like I'm getting your sloppy seconds."

"Nonsense. We always share sloppy seconds with our vibrators."

"That's different," Morgan said. "We clean the sex toys after every use."

"Wouldn't that also be true of Richard's penis? He's a hygienic person. Obviously he uses soap on his dick when he showers everyday."

"I know, but sharing a penis is in a whole different universe than sharing sex toys. It's not even close to being the same thing. There's an actual human being attached to a penis. A vibrator is a mechanical device. "

CJ looked unfazed. "I fail to see the difference. Anyway, you look really fuckable right now. I'm not sure why you're so obsessed with fixing your dress; you won't be wearing it when he comes in the room."

"Shit. I forgot all about the medical gown."

"Underneath which, you'll be naked."

Morgan nodded. "Come on. Let's go. I'm so nervous my legs are shaking and I want to sit."

They finished their bathroom self-examination, headed towards the elevator and went up a few floors to the doctor's waiting room. After checking in, they sat down with their magazines and waited while the tv played in the background. There were only a few other people there. Mostly seniors.

Morgan began having second thoughts. She wondered if this was a horrible idea since people might hear as she lost her anal virginity. She began to shake and her heart raced at the thought of people -- nurses and patients -- listening to their secret fuck session.

That train of thought ended when a nurse appeared, with a clipboard in hand.

"Morgan Whitfield," the nurse called.

Morgan turned to her friend and whispered, "Okay, wish me luck."

"You won't need it," CJ whispered back. "You'll need plenty of lube though."

Morgan flashed a 'bitch please' expression and followed the nurse down the hallway, knowing her ass would never be the same again.

*

The nurse took her to the exam room. Morgan was seated on the exam table which was covered by white paper. The room had all the instruments in place, which made Morgan gulp.

The nurse asked Morgan about the reason for her visit, and she answered, "Um, it's private." The nurse raised an eyebrow, but went on asking other personal questions.

Before the nurse left, Morgan was given a thin white gown. She removed her clothes and put on the gown which left her ass completely exposed. Normally, she would have sat there calmly. But now she was on the verge of accepting a large penis in her rectum, in a medical exam room of all places.

She had no clue how this would end. Her attention suddenly shifted to a medical poster on the wall. Morgan didn't know much about the anal area. She thought it might help her relax if she took a closer look at the poster.

The back of her gown opened when she stood up to look at the diagram, when suddenly the door opened behind her. Whoever had entered the room had gotten a nice view of her bare ass. Her hands quickly covered her bottom, in a failed attempt to conceal her partial nudity. Swiftly, she turned around and sat on the exam table.

The embroidered name on the left side of his coat read "Dr. Williamson."

He was taller than she expected, and looked exactly like his online pictures. After entering, he squinted his eyes as he wondered if he was seeing things.

"Morgan?" he asked, cautiously shutting the door.

"That's me," she confirmed.

"I was told I had a new patient, but I certainly wasn't expecting you."

"Did you notice CJ waiting in the lobby?"

"No. She didn't tell me that either of you were coming."

"That's because we wanted this to be a surprise," she replied.

He slowly nodded. "I'm assuming you're here for more than just a routine check-up."

"I've paid my deductible, so I want the check-up too."

"In that case, you're about to have a thorough exam."

"Judging by CJ's pictures, it will be a deep exam."

"You'll feel every inch," he said with pride. "But my specialty is making it easy and enjoyable. Shall we start?"

Richard spent a few minutes doing all the doctorly things one would expect during a check-up. He checked her vital signs, looked in her eyes and ears, and listened to her heart and lungs.

"May I?" he asked, putting one hand across the thin gown covering her breast.

"Sure."

He pulled down the front of the gown to reveal nicely shaped b-cup breasts. Her pink nipples were already stiff. Morgan noticed his eyes lingering on her tits for more than a few seconds.

"A perk of the job I'd imagine," Morgan teased.

"Actually, I'm wondering if you're cold or highly aroused."

She blushed knowing that while he checked for lumps, he was also making note of her hard nipples. After all, she used to be openly disdainful towards him. Now here she was, with her aroused tits exposed, ready to be taken in her ass.

"Now for your rectal exam," he said, with an impassive expression. "Stand up, turn around, and bend over for me,"

The pivotal words were said with very little emotion.

Morgan refused to budge. "I can't seem to figure you out. Your book depicts you as someone passionate about anal sex. Yet you're so... so ... "

"Clinical?" he smiled.

"Yeah, why aren't you lusting after me right now? I'm naked and about to present my ass. Shouldn't you be flipping me over and shoving it in?"

"Maybe I don't want to come across as creepy," he replied playfully. "Isn't that the name you had for me? Dr. Creepy?"

"Sorry. I didn't think CJ would tell you that."

"She's told me a lot. I can understand your apprehension, about me, my writing, about everything. But the truth is, I became a doctor to make a difference. And I've always been interested in human sexuality. So why not combine the best of both worlds?"

"That sounds admirable," Morgan said honestly.

"Speaking of admirable, I don't want to pressure you into doing this. I mean that, sincerely. Forcing or coercing women isn't my style. I'm all about shared pleasure. If you're nervous, uncomfortable, or feel like this isn't for you, just let me know. We'll finish up this appointment, hopefully I'll give you a clean bill of health, and you'll be on your way."

Morgan smiled widely. "I really appreciate that. The real truth is, CJ knows me too well. We're both fairly open minded when it comes to sex. And anal has been on my radar for years. It's just... scary."

"Of course it is," he agreed.

"Having sex with strangers is also scary for me. But I think I can make an exception today."

His eyebrow rose. "Is that so?"

"Why not? You're bound by doctor/patient confidentiality. You know what you're doing. And plus, you're kind of hot."

"Admit it, Morgan. Sex in a doctor's office is a turn-on for you."

"Was I obvious?" she blushed.