tagAnalHow to Have Anal Sex

How to Have Anal Sex

byHeyAll©

The whole thing started when Morgan and her best friend CJ were in their backyard tanning. They wore nothing but small bikinis as they both lay face down on their beach blankets, which were sprawled across the grass.

To them, tanning was the biggest perk of their move to Los Angeles. Sunlight was plentiful compared to their birthplace of Seattle; a place where their bottoms remained lily white. They had pooled their resources and leased a cozy home with a small backyard that was semi-private (or so they thought).

"What time is it?" Morgan mumbled, refusing to open her eyes.

CJ checked her phone. "1:34."

"Time for me to go."

As much as Morgan wanted to enjoy an afternoon in the sun, her work was waiting. She had always wanted to be a teacher, and was lucky enough to land a part time teaching gig. The only downside of teaching Literature courses at the local community college was that she worked odd hours.

"Me too," CJ agreed.

"Where are you going?"

"I've been printing like crazy and need new ink."

For her part, CJ was a freelance paralegal, which allowed her to work mostly from home. It was a pretty good gig. She worked job to job, doing research and typing on her computer, while wearing next to nothing and playing pop music in the background.

Morgan finally got to her knees. "Enjoy your afternoon. I'll pick up a pizza when I come back."

"Just what my diet needs."

"You could use the extra calories, you skinny little bitch."

Morgan reached over and slapped CJ on the butt, which resulted in a loud smacking sound and a giant flinch from its recipient.

***

It was just after 5:45 by the time Morgan arrived home. Gone was the bikini-clad California girl look. Now she was dressed in something far more respectable; jeans and a crisp white button down cotton blouse. It was the perfect look for a hip, cool, young professor. She carried a large black leather tote over her shoulder which contained a laptop and supplies. And of course, she had a large pizza in hand, as promised.

"CJ, the food's ready!" she hollered, putting it down on the dining table.

Morgan went straight to her room to change her clothes.

"I'll be there in a minute!" CJ hollered back.

"I'm not waiting for you! It smells amazing!"

Morgan quickly changed in her room, as usual, without closing the door. She stripped and put on a loose fitting t-shirt and shorts. A wave of relief swept through her body as she got comfortable in her skimpy outfit.

After washing up, Morgan grabbed plates from the cabinet and sodas from the refrigerator. Then she sat down and dug right into the hot, cheesy pizza. She wasn't shy about eating before her friend sat down. As CJ stepped into their dining room, dressed in cut offs and a camisole, Morgan chewed heartily on the warm cheese that was dripping off her first piece.

"Cheese goes straight to your ass, you know," CJ pointed out with an evil glee.

Morgan put the slice back on the plate as she chewed. "Gee thanks. I paid for this pizza, as a reminder."

"I know. Thanks a bunch."

CJ dug into the box and grabbed a slice for herself, devouring it with the same zeal.

"I ordered it with kalamata olives and extra mozzarella today," Morgan pointed out as she took another bite. "Freaking amazing."

CJ took an even deeper bite. "Perfect for ass-fattening."

"What's with you today? I don't want to hear about my butt size while I'm trying to enjoy this pizza. I workout hard and deprived myself all week on my diet. I deserve a chance to splurge."

"I know," CJ nodded. "And I agree. But while you were gone, I had an interesting day which could affect us both."

"Regarding our butts?" Morgan said sarcastically.

"Actually, yes."

Morgan narrowed her gaze. "You're kidding."

"Nope."

"Then tell me."

CJ washed down her food with cherry coke. "After running some errands, I stopped by the store across the street to buy some fruit. That's when a guy introduced himself to me. Oddly enough, he approached me from behind, which foreshadows this story."

"That's not creepy at all. Nope."

"Your sarcasm aside, it's the best thing that's happened to me all month. Or rather, happened to us."

Now this, Morgan had to hear, taking another bite of her pizza. "Go on. I'm listening."

"His name is Richard. He's a really good-looking guy, sharply dressed, in his early 40's I think. The more we talked, the more interested I became. For two reasons."

"Mmm Hmmm...." Morgan chimed in, washing down her pizza with an orange soda.

"First, he's a doctor. Second, he's an asshole specialist."

Morgan took a hard gulp. "You've gotta be kidding me! CJ, you did a lot of weird things in college. But... come on ... I mean ... how do you know he's even a doctor? What kind of guy introduces himself as an 'asshole specialist,' or whatever he said."

"You have to let me finish," CJ replied. "He didn't call himself that, I did. It made him laugh."

Morgan sighed. "Duly noted."

"Anyway, as someone who works in the legal profession, I know other professionals when I see them. He has the look and aura of a doctor. Plus, he was well-versed when talking about his job."

"Did you see his ID or anything?"

"No. But he saw ours. You know that hospital down the street? Richard was on his break and saw us sunbathing earlier. Actually, he's seen us several times. That's how he recognized me at the store, by the shape of my perfectly sculpted butt."

Morgan practically spit her drink out. "For fuck's sake!"

"Okay, I acknowledge that part sounded creepy. But it's not! We had a charming conversation, and it just so happens he's writing an instructional guide to anal sex."

"CJ, I've spent 30 bucks on this pizza," Morgan said with a deadpan expression. "Hearing about Dr. Creepy is making me lose my appetite. Are we going to have to change our locks and add more security now?"

"No way. I promise you, this story isn't nearly as creepy as it sounds. He's a great guy."

"Yeah, a great guy who spies on us when we sunbathe, recognizes you by the shape of your butt, and writes about anal sex. Seems legit."

CJ smiled. "To be fair, he's written about other sexual topics, not just anal. For example, oral sex...."

"Okay, enough of that," Morgan interrupted. "What you decide to do with your asshole is your business."

CJ batted her eyelashes. "Actually, it's our business."

"Nope, leave me out of it."

"I've invited him to dinner."

"What!?" Morgan hollered. "Here!?

"It's my house too! I pay half of the bills. But please, hear me out."

Morgan unleashed an even louder sigh. "What else is on your mind?"

"Our asses. Literally. This guy is collecting information for his book. It's... research."

"Research, eh?"

"Yes, research."

"That has to be the oldest entry in the book of bad pick-up lines," Morgan said with an eye roll. "He gets to butt-fuck you in the name of 'research' for a book he's allegedly writing. Again, is he even a doctor? Or just some voyeur who spies on us and stalks you at the store?"

CJ was on the verge of thinking up a long retort that she planned to deliver in a lawyerly fashion. Instead, she burst out laughing, causing Morgan to do the same.

"Okay, okay," CJ snickered, before taking on a more serious tone. "Look, I know it seems creepy. I completely get it. But all the talk of anal sex came from the natural ebb and flow of adult conversation. We really hit it off right away and I pried the information out of him because I found him interesting."

Morgan paused and studied her friend. "You seem to like him. Dating material?"

"Like I said, he's in his early 40's. Older guys are sexy, but in terms of dating, it'll never work. I'm too energetic."

"Ah, okay. Sexually, then?"

CJ smiled. "Possibly. We could really learn a thing or two, and your bad experience will fade from your memory."

Almost reflexively, Morgan's butt cheeks clenched, squeezing the fabric of her panties together. As much as she tried to forget, her asshole wouldn't allow it.

"Don't remind me," Morgan said, mournfully.

"We're in our sexual primes," CJ pointed out. "Some experiences will be good, some will be bad. This is a great opportunity to explore something new."

"So that's what this is about? Your anal exploration."

CJ lifted an eyebrow. "Our anal exploration. Just because our ex-boyfriends weren't good at it, doesn't mean we should never try it again."

"Why?" Morgan said, feeling the instinctive clenching of her butt cheeks once again. "Some things are better left forgotten."

"The way I see it, women have three holes for pleasure. We're missing out on one of them."

"That's yet to be confirmed. If I've never had pleasure there, then it's probably not possible."

"So your ex-boyfriend just rammed it in," CJ shrugged. "With a little bit of lube."

Morgan clarified, "Barely any lube."

"Exactly. It's a super delicate act and we're lucky we've found a professional. I mean, for heaven's sake, this guy went to medical school. He has a formal education worth over a hundred thousand dollars. He's literally trained on how to penetrate an asshole with ease."

"Among other important things, I'm sure."

CJ shrugged again. "Yeah, he's saved a few lives too, I think. But that has nothing to do with us."

"Okay, I'm convinced," Morgan sighed and held up her hands. "Convinced that I'll never change your mind. You have your opinion. I have mine."

"What are you saying?"

"I'm saying, if you want to see this guy, date him, fuck him, suck his dick, or let him play with your butt hole, leave me out of it. My point is, I won't make any negative comments. In fact, I'm actually glad you've found a guy you like. We should be making more friends here. Good for you."

CJ gave a purposefully cute expression. "Can I bring him over? He could swing by for coffee when he's on his break."

"How convenient for him. Instead of spying on us from afar, he can simply come over and stare at your ass up close."

"Actually, I'll wait until you're asleep so he can come over and gawk at your ass too."

Morgan crushed the pizza crust in her hand. "No."

"That was a joke."

"It better be. If you trust this guy enough to bring him over, please make sure I'm not around. And let me know his name, so the next time I go to that hospital, I can avoid him."

***

A few days passed before Morgan joined CJ for a backyard tanning session. She intentionally waited until Saturday morning, fairly certain the doctor wasn't at work.

She slipped into a little bikini and brought her beach blanket out back to lay alongside CJ, who was dressed similarly.

"Oh, you've decided to tan again?" CJ asked, almost sadly.

Morgan rolled out her blanket next to CJ and laid down on her stomach. "Yeah, I don't want to be the whitest girl on campus. Why? Were you looking for some alone time?"

"Not at all. I was just about to get a little more comfortable, if you catch my drift."

"Why are you being awkward? We've seen each other in bikinis hundreds of times. I've even seen you naked."

"Okay, don't say I didn't warn you."

Suddenly, CJ raised her butt while her face was pressed to the towel. She reached below to pull her bikini bottom off, leaving her bare from the waist down.

"CJ!" Morgan hissed.

"Hey, I warned you."

"Sheesh. Are you going to take your top off, too?"

"No need," CJ replied, laying down comfortably. "I'm trying to get rid of the tan lines on my butt. It's for a legitimate purpose."

Morgan postulated. "This has something to do with your doctor friend, doesn't it?"

"Yep."

"I thought we agreed not to discuss him anymore."

CJ spread her legs wide to tan between her cheeks. "Hey, you're the one that brought up that topic."

"Fair enough."

Morgan couldn't help but quickly glance at her friend's bare bottom. CJ's ass was smaller than hers. It was a bit on the thin side, as were her legs, and tan lines were prominent. The contrast of the bronzed skin tone against CJ's naturally creamy white skin tone was striking.

As Morgan laid on her stomach and tried to relax, she couldn't stop thinking about this situation, much to her own dismay.

"I mean, why does he even care?" Morgan eventually questioned. "Do tan lines ruin this guy's libido? If so, that sounds like a strange turn-off. I personally think tan lines are sexy and I know for a fact that a lot of men like seeing them. It makes your Dr. Creepy seem like even more of a phony."

CJ rolled to her side, almost exposing her pussy. "Actually, he loves my tan lines. He's been very complimentary towards them."

"Then why is your butt exposed? Are you flashing him right now? Does he work on Saturdays? Oh God, I think I better go."

"No one is watching us," CJ laughed. "I'm getting rid of my tan lines for a good reason. He's taking pictures of my butt. All kinds of pictures from different angles."

Morgan sighed. "Let me guess, his book."

"Actually, yeah, that's right. Nice guess."

"CJ, I know I promised not to give you shit, but you're being played. There is no book. And he's probably not even a real doctor. He's just a smooth talker and wants pictures of your ass. When you eventually break it off with him, he'll use it for jerk-off material. We're in freaking LA; creepsters and wannabe porn directors are everywhere."

"Wait here," CJ said, rolling over. "I'll be right back."

Morgan's eyes widened. "No, wait, don't..."

Ignoring the plea, CJ stood up without bothering to cover herself. Her cleanly shaven cunt and tan lined crotch were on full display. Morgan shook her head as CJ walked half-naked back into the house. If anyone had been spying on them, and surely there must have been some watchers, they were given a real treat.

CJ returned moments later and laid on Morgan's beach blanket, so they could be side-by-side. She had brought back an iPad.

"Here, have a look," CJ said, handing over the iPad to Morgan.

As they huddled together, Morgan took the device and saw multiple tabs open on the web browser.

"What am I looking at?" Morgan asked.

"This is his Facebook. As you can see, he's a real human being with friends and hobbies."

CJ pressed the screen and showed the next tab.

She continued, "On this page, you can see his bio on the hospital website. He really is a doctor. Unless of course, he somehow hacked the hospital website or conned them. I doubt he's that skilled though."

CJ pressed another tab.

She continued, "This is his Literotica page. He writes erotica, the classy kind, under a pseudonym. As you can see, he has a lot of high scores with Hot ratings. You can also see he's written a number of "How To" instructionals, based on his experiences as a guy, and as a doctor. His instructionals have received hundreds of great reviews from both men and women."

CJ flipped to the last tab.

She continued, "Finally, here's his Amazon page, under the same pseudonym. He's written a few e-books. Basically they're more explicit versions of his instructionals, which also includes pictures of real life models. No faces."

"You're going to be a butt model for the anal instructional?" Morgan asked incredulously.

"That's right. No face. No way of identifying me. Just my cute little, flat butt. It's fun in an exhibitionist sort of way."

"Jeez, how many people do you think will see it?"

CJ thought for a moment. "His last two e-books averaged around 600-700 downloads I think."

"Yikes. I could never do that."

"Of course you can. All you have to do is lose the bikini bottom."

Morgan looked puzzled. "For something like this, you're only showing your butt? You'll just be standing there with your butt exposed? What else?"

"Legs spread," CJ said before nervously pressing her lips together.

"And?"

"One or two shots of my anus, I think."

Morgan sharpened her gaze. "And?"

"One or two shots of anal penetration. It's for a good cause, really. Think of how many couples will benefit from this. It's my contribution to the world. Did you know that most of his twitter followers and book purchasers are women?"

"CJ, you're going to be a porn star!"

"No I'm not! The human body is beautiful and so is sex between consenting adults. This instructional will help many couples around the world express their love."

"Fine," Morgan conceded. "It's your choice, your bottom, your rectum. I promised I wouldn't give you shit, so I won't."

CJ bent over and kissed Morgan's shoulder. "I know you better than you think. You'll come around. Trust me."

They went back to tanning and savored the heat of the sun against their tender skin. Of course, CJ was enjoying it more while viewing it as necessity.

Morgan couldn't help but cringe when she noticed CJ's legs were widely spread, allowing the sun to bronze the area around her anus.

***

It was 6:24 on a Wednesday evening and Morgan stayed in the classroom after her lecture, so she could focus on grading papers. The room was empty; it was one of the few places where she could find peace and quiet.

With a pen in hand, she went line-by-line through her students' writings and gave critical feedback.

Her teacherly concentration broke the moment her phone buzzed. She looked at the name on the caller ID, and had no idea who it was. The first name was 'Richard,' which caused her eyes to squint.

Could it be?

"Hello?" she answered tensely, hiding her fury.

"Hello, is this Morgan?"

"Speaking."

"I've heard many great things about you. I'm Dr. Richard Will---"

Morgan jumped right in. "Are you serious?! Are you serious right now? You're calling me at work? You know that I teach students, don't you?"

"Adult students, right?"

"That's beside the point. I'm in a classroom."

"CJ said that you're alone in class right now. Are you busy?"

"That's also beside the point. And how did you get this number, anyway? Are you stalking me too?"

"Actually, CJ gave me this number. She wanted me to call you."

Morgan leaned back in her chair and briefly closed her eyes. "Okay, I guess she really wants us to talk. Are you two... dating?"

"No, we're not," he replied. "I really do like her and enjoy her company. But, she's made it clear she's not looking for a relationship, and frankly, I'm much too busy with my work at the moment."

"So it's purely sex."

"Educational sex," he clarified.

"Are you fucking her on a regular basis now?"

Richard paused for a moment. "You're very direct."

"Sorry, but I'm very protective of her. We're like sisters."

"I know. She's talked about you quite a bit. I can tell you two are close and she really wants your approval."

"Well, she doesn't need my approval, but she has it anyway. I've already told her that I'm cool with it, or at least I try to be. I actually respect what you do. Learning about sex is important. Especially in a delicate area... like the backdoor region."

"Yeah, CJ told me about your painful anal incident. It sounds like your ex-boyfriend didn't know what he was doing."

Morgan tensed. "Oh?"

"I didn't mean to be that blunt," he said with sincerity.

"No worries. It wasn't that big of a deal. It hurt a lot, that's all."

"It absolutely hurts when an inexperienced guy rushes the action."

Morgan nodded silently to herself. "Yep, you're right. Anyway, it was nice talking to you. You seem like a decent guy. I wish you the best of luck with your e-book, or whatever."

"Actually, there's another reason CJ wanted me to call you."

Morgan thought quickly. "You want me to proofread or edit your book? She must have told you that I used to be an editor."

"A professional editor sounds like something I could use. Maybe I'll make you an offer if you'd be interested. But no, that's not why she wanted me to call."

"Hmmm.... Why do I have a weird feeling about this?"

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