Anal Confessions 29646k

Anal Confessions

By Kate Harder Copyright 2019 Kate Harder Smashwords Edition

The following story is a work of fiction. All characters and events derive solely from the author’s imagination. Any relation to real-life events is purely coincidental.

Author’s note: All characters depicted in this work of fiction are 18 years of age or older.

Daphne opened her eyes slowly as she became aware that Gavin was already awake, with his arms around her from behind and pulling her closer to him. She also felt a bit of solid probing at her, which was a sure sign of what he wanted.

Daphne really loved him and adored having sex with him, but when he stayed overnight, she never got enough sleep. Opening one eye, she glanced at the alarm clock.

Oh my god, she thought, groaning inwardly. It’s only freaking 5:30AM. She had another good hour before she had to get up and get ready for work. Maybe if I just lie here very still, he’ll let me go back to sleep.

No such luck. Gavin was waking up more by the second and it seemed that “Little Gavin” was already as awake as he could possibly be. Daphne felt him nudging at her neck now.

“Baby, are you awake?” he whispered among more nudging. “Daphne, are you awake?”

“No, I’m not,” she replied somewhat grumpily. “I don’t have to be awake for another hour.”

“Oh, good! You ARE awake!”

Her response seemed to only have made Gavin more determined and excited in pursuit of early morning sex. He gathered her even closer to him and made a

slight grinding movement against her ass.

“Gavin, noooooo, please,” whined Daphne. “I only got 4 hours of sleep last night. I’m exhausted and I’ve got to work late tonight.”

“This won’t take that long, baby,” murmured Gavin. “I’ll make sure you like it, too.”

With that, he moved his hands up to her chest where he started to gently massage her nipples. He really did know her too well. This was the one thing that he could do to her that would have her wanting him in a matter of seconds. Sometimes she thought that her nipples were the most sensitive part of her body. She had very nearly reached orgasm just from him playing with her nipples in the past.

“Ohhh, you’re beyond cruel,” Daphne moaned. She could already feel that intense tingling between her thighs. Oh yeah, there was no turning back now even though she was perfectly happy to remain on her side, feeling Gavin’s rock hard erection pressing against her from behind. Gradually, he moved one hand down to her pleasure center and slid inside the front of her bikini panties.

“Mmm, I knew you wanted it, too,” he whispered in her ear.

Obviously, she was soaking wet from all the nipple attention. Involuntarily, she moved against his hand, and urged his fingers to start working their magic. Gavin had always known how to play her body like an instrument, even from the first time they had ever been together. She responded to him as she had never responded to another man in her life, and she was reminded of this as she felt

Gavin’s fingers working expertly around her engorged clit.

Daphne whimpered as she felt her orgasm building under the ministrations of his fingers. She could also feel his hardness pressing against her ass as well as some spreading wetness from his opening. She had always loved that he got almost as wet as she did. There was never any doubt as to the level of Gavin’s excitement. The more turned on he got, the more pre-cum he produced.

Wiggling her luscious ass cheeks against him rewarded her with quite a response, which shot her excitement level up several more notches.

Gavin started to push her bikini panties down now, so that she would be bare against him. She also figured that he was almost ready to be inside of her. These early morning encounters rarely lasted very long, but that was ok with her.

As Gavin pressed his engorged member against her now naked ass, Daphne could feel the trail of wetness that followed. She moved around a little more to push back against him and she felt the head of his erection poke her between her cheeks. Whoa! She thought as she rapidly backtracked away from him.

“What’s wrong, baby?” Gavin whispered.

“Um well, I THINK you just about got the wrong hole,” Daphne replied.

“Oh, I didn’t mean to do that,” Gavin said. “I know you don’t like that. Here, let me make it up to you.”

He went back to working his magic on her pleasure core and she forgot all about everything except the way his fingers felt. In a matter of seconds, her moaning was growing louder and finally hit a crescendo as her orgasm peaked. As she was coming down a bit from her pleasure high, she felt Gavin moving behind her so that he could enter her from behind. She was more than ready for him.

Daphne could feel the head of his cock as it probed the opening to her pretty pink love tunnel. She closed her eyes as she felt him push so that he was inside of her in one fluid movement.

“Ahh, that’s it,” moaned Gavin as he started to move in and out of her.

She put her own hand between her thighs now as he took her from behind and started to make fast circles around her clit. Just as Gavin plunged hard and deep into her, she was pushed over the edge once more. Both of them came in a rush of movement and loudness.

Now, gasping for air, he continued to hold her against him while he remained inside of her. This was definitely one of the things she loved about Gavin. He always held onto her for a long time following sex and stayed within her until they were ready to part. Many times, they would fall asleep this way and wake up to him still being in her and hard. This, of course, would lead to another really hot encounter.

Smiling, Daphne dozed back off to sleep once more.

The next time Daphne awoke, she was alone in bed and could smell coffee brewing. Smiling, she turned onto her back and stretched like a very contented cat. She sort of felt like one, too. If she could have, she would have started licking her hands and meowing for a saucer of milk.

Ok, well, she thought, maybe not to THAT extent, but she had to it she felt pretty damned content right at that moment. She could hear Gavin moving around in her kitchen and wondered what other delights awaited her.

As Gavin appeared in the doorway about then, Daphne didn’t have to wait long to find out. He was carrying a tray that held a bowl of strawberries, a small plate containing a mushroom omelet, a glass of juice and, thank you God, a cup of freshly brewed coffee. She sat up and plumped her pillows behind her back so he could set up the tray for her.

“WOW!” Daphne exclaimed. “Breakfast in bed! What a treat!”

“It was the least I could do since I made you miss some valuable beauty sleep,” Gavin laughed. Then he leaned over and gave her kiss. “I’m going to take a quick shower while you eat. Enjoy!”

And enjoy she did! Everything was wonderful and actually much more than she would have made for herself. Gavin was always doing such sweet things for her. As she nibbled on the last strawberry, her mind went back to earlier that morning and their spontaneous physical encounter. He really IS a sexy, sexy man, Daphne thought. He also certainly knew what buttons to push on HER! She could hear the shower still running. Maybe she would go and him. Then she glanced at the clock and knew there was simply no time for Round Two.

Sighing, she reluctantly pushed the tray back and got out of bed. She walked into her closet and started to put together an outfit for today. Daphne’s job was as a DJ for a local radio station. Her shift started mid-morning but she needed to be there early and set things up. She loved her job along with the bit of celebrity that it brought to her. Even though her listeners rarely saw her in person, she still made a point to dress presentably. You just never knew what might come up. Today, she had a guest on who was a very well-known sex therapist and she didn’t want to show up in faded jeans and a t-shirt.

Daphne was just getting ready to head into the bathroom for her shower when Gavin walked out wearing only a towel. Grinning at him wickedly, she wrapped her arms around his naked torso and stood on tiptoes to give him a very promising kiss. As she stepped back, she glanced down at the towel and saw that she got the reaction she wanted.

“There will be much more where that came from tonight,” she promised as she closed herself in the bathroom and started the water.

Daphne made it a quick shower since she was already running a little later than she liked. Besides, she was actually looking forward to meeting this sexpert. They needed to go over the topics she would discuss on the air as well as what sort of questions she would be willing to take on from live callers.

She stepped back into the bedroom just in time to give Gavin another encouraging kiss before he left for work. If his law partners only knew what he did in his time off, she thought. They really did make sort of an odd couple when you gave it any thought. But she didn’t care what other people may think about their union. She was happy and he seemed to be as well.

Daphne arrived at the radio station only a couple of minutes later than her usual

time and was relieved that she had managed to beat her guest there. She grabbed another cup of coffee and then made her way to her office. This was where she did her planning and music lineup for her show and she was always quite comfortable in it.

While she was going over her notes, her guest knocked on the door. Daphne was pretty amazed at the woman standing before her. She looked nothing like a sexpert at all. Her age was probably mid-40s. She was around 5’3” with short iron gray hair. She carried probably about 25 extra pounds.

“Hello,” she said, smiling at Daphne. “I’m Dr. Emily.”

“It’s great to meet you, Dr.” Daphne enthused as she heartily shook Dr. Emily’s hand. “Welcome!”

They spent some time getting acquainted and going over what the show would entail. It turned out that Dr. Emily was open to answering ANY type of sexual questions, so there were no issues there. Then it was time to go on the air.

“Hello everyone, this is Daphne with the Mid-Morning show at WSEX. Today, I have a very special guest with me and I know you’re all going to be lining up to ask your burning questions. Well renowned Dr. Emily is going to be taking your questions in just a few minutes. Welcome to the show, Dr. Emily.”

“I’m so happy you’ve invited me to be here. I look forward to answering any questions that I can.”

The two women went through a short interview on how Dr. Emily gained her status and then opened the phone lines. At first, there were the usual questions, and the doctor dealt with them quickly and efficiently. Just after a commercial break, however, there was a caller that piqued the interest of Daphne.

“Hello, Caller, you’re on the air with Daphne and Dr. Emily. What’s your name and question?”

“Um well, this is Johanna and my question is that, lately, my boyfriend has been trying to talk me into have having um, well, um, anal sex. I’m kind of afraid to do it and I keep saying no and he keeps getting all mad at me. I’m afraid he might break up with me if I don’t do this. Can you help me, Dr. Emily?”

“Well, Johanna, I can offer you some techniques that will make the introduction to anal sex much more comfortable and maybe even help find it pleasurable. But first, may I ask why you’re so against trying this?”

“A couple of my girlfriends have tried it before and they hated it! They said it really hurt and they would never do it again. So now I’m afraid to try it.”

“I see. Ok, first of all Johanna, your friends partners were most likely doing it incorrectly if it caused them that much pain. The first rule of anal sex is to that it’s far different from vaginal sex. Now, I’ll give you a few tips on how to make it a more pleasurable experience.”

Daphne felt like whipping out a pen and pad to start taking notes, but she refrained. Instead, she paid very close attention to the next words that came from Dr. Emily’s mouth.

“Now, the first and very important thing that you need to regarding anal sex is lubrication. I can’t say that enough. Lubrication, lubrication, lubrication. The right amount of lubrication can make all the difference between a pleasurable experience and a disastrous one.”

“What kind of lubrication?” asked Johanna.

“There are various types of it available. To begin with, you’ll probably want to start out with something like Anal Eze. Not only is it an excellent lubricant, but it also contains a numbing agent. This will keep any initial discomfort at a minimum.”

Dr. Emily went on to say that it was also important to watch the amount of food you ate for 24 hours prior to having anal sex, for obvious reasons. She also explained how necessary it is for the man to be gentle and slow when entering. It was recommended that something smaller than a penis be used to ready the area, such as a finger. In that way, it wouldn’t be such a shock when an erect penis started to enter.

Johanna had a few more questions and then thanked Dr. Emily. This call seemed to open a floodgate of calls regarding anal sex. Some from women that were afraid to try it, and others from guys that wanted to know how to get their wives or girlfriends to do it. The rest of the show went by quickly because of this and, before she knew it, Daphne’s show was at an end.

She thanked Dr. Emily profusely for being her guest and asked her if she would consider a return engagement at some point in the future. Dr. Emily enthusiastically agreed to schedule another appearance. Then they parted ways.

Daphne had some phone calls to return and paperwork to finish up before she headed home. She almost forgot she had a meeting that evening with the station director but she didn’t think that would take very long.

Apparently, Dave had caught her show that day and wanted to spend more time talking about that than whatever he called the meeting for. It seemed that her ratings shot sky high during that show and he was quite impressed. Suddenly, it hit Daphne that Dave had called this meeting to tell her she wouldn’t be getting her usual raise, but he seemed to have changed his mind. By the time she left, she had agreed to another year with the station at a 40 percent raise.

That had her feeling pretty good so she stopped on the way home and picked up some Chinese food and a bottle of wine. Gavin should be at her house by now and would probably be hungry. The wine was to celebrate her raise. Just as she got to her turnoff, she changed directions and headed to the local adult store. She just wanted to check some things out.

Daphne wasn’t shy about visiting this place. She had done it many times in the past. However, she had never come looking for things to use in anal play and she wasn’t sure how she felt about that. After looking around and finding that she could get everything she needed right here, she ended up only purchasing a DVD about anal sex. She pointedly ignored the leer she got from the guy behind the counter, paid for her DVD and left.

Gavin was already at her house when she arrived so she tucked the DVD into her purse. Daphne wasn’t quite ready for him to see it yet. She walked inside and was greeted with a huge hug and long ionate kiss.

“Hmm, did you miss me or something?” she teased.

“I always miss you,” Gavin replied and gave her another lingering kiss. “Now what smells so good?”

“Oh, you mean besides ME?” Daphne giggled. “This is Chinese and this is a bottle of wine to go with it. We’re celebrating tonight.”

“Really? What are we celebrating?”

“My raise!”

“Baby, that’s great! I know you were wondering if you were even getting one this year or not!”

“Yeah, I really was. Did you happen to catch any of my show today?”

“No, I didn’t. I tried to around lunch but I ended up having to work straight through on that new case I have.”

Daphne explained about Dr. Emily and how the ratings just blew through the roof. She didn’t mention the topic that had really got things going, though. She would save that until after dinner. They discussed her raise and his new case over some amazing Chinese food and great wine. Then, they finally settled on the couch to relax.

“Gavin,” Daphne said tentatively. “Do you when we were talking about that thing you said you wanted to try?”

“Umm, I’m not exactly sure which “thing” you mean,” Gavin replied slowly.

“Well, it’s the thing that I said I would never, ever do so you need not ask me.”

“Ahh. Yes, I think I know what you’re talking about now.”

“Well, I’m actually a little curious about it. See, that’s what Dr. Emily’s topic turned out to be today when a woman called in about it, and I decided it might be kind of fun to try after all. I mean, I’m not POSITIVE, but I did a little research and I got something that I want us to watch.”

With that, Daphne pulled the DVD out of her purse and showed it to Gavin, whose eyebrows shot up instantly. He handed it back to her with a look of complete amazement on his face.

“So, we’re going to watch this DVD and then you’ll decide if you’re ready or not?”

“Yeah, that’s kind of the plan,” sighed Daphne. “Also, I know you have sort of had your heart set on trying this. I hate disappointing you sexually, so it’s only fair that I see what all the fuss is about. Then I can make an informed decision.”

“First of all,” said Gavin as he gathered her into his arms. “You could NEVER disappoint me sexually. But this is a good idea. You can see whether you feel you can go through with it or not. Just understand that I won’t be upset either way. Ok?”

Daphne nodded and gave him a quick kiss. Then she slid the DVD into the player and turned it on.

The movie was about what you would expect from porn but this one was higher quality than most and actually served as somewhat of a “tutorial” about anal sex. The plot was simple: An 18 year old innocent young lady went to the big city with even bigger dreams and one thing led to another. As she had never had anal sex before, there was a lot of detail about everything involved, all of which Daphne was paying very close attention to. She was gratified to see from the corner of her eye that Gavin also seemed to be riveted to the screen.

When the movie had ended, Gavin turned to Daphne and said, “So what do you think?”

“I’m still not totally sure,” she replied. “But I do promise you that I’ll think about it.”

In reality, Daphne had already made up her mind. She just wanted it to be a surprise for Gavin. That night, he virtually attacked her in bed. She wasn’t sure she had ever seen him so worked up. That told her just what she needed to know. He apparently was a lot more interested in anal sex than he had let on.

The rest of the week went quickly and uneventfully. Daphne had decided that

Saturday night was going to be The Night. She figured they could sleep in that morning and could stay up late that night. Plus, neither of them had to work so it would make it a more relaxed sort of experience. She stopped by the adult store on her way home from work on Friday and bought the necessary supplies. Then she locked them in the trunk of her car because if Gavin saw them, he would know what was going on.

On Saturday night, Daphne and Gavin cooked dinner together and ate by candlelight. He had asked her earlier if she wanted to go out that night and she told him that she really just felt like having a quiet evening in. They were both sort of in synch about things like that so it wasn’t an issue.

Following dinner, they both cleared the table and straightened up the kitchen a bit. Gavin settled in front of the television to see what was on and Daphne slipped away to the bedroom. Earlier, she had sneaked the bag of supplies from her car and had them tucked away in her closet.

Now, she retrieved them and went into the bathroom. Locking the door behind her, she withdrew a sexy little red and black chemise from the bag. It had the unique feature of the entire ass being cut out. So she could still be wearing something sexy while Gavin stayed “on target.”

There were scented candles, a tiny anal probe, and the lubrication that Dr. Emily had suggested. She dressed quickly in the chemise and put her robe over it in case Gavin decided to come into the room before she was finished. After setting up the candles and lighting them, she placed the probe and lubrication on her nightstand. She arranged herself on the bed and called to Gavin to her.

His jaw dropped when he saw this scene. Clearly, he was very surprised and, it seemed, quite delighted. At first, he didn’t understand that there was something

different happening until he saw the probe and the lubrication. Then his eyes really lit up.

“Seriously?” he asked.

“Seriously,” Daphne nodded.

He was out his clothes faster than she had ever seen him move. Crushing her to him on the bed, he started to stroke her body everywhere he could get to as he kissed her deeply. Gavin’s response made Daphne’s apprehension take flight and her excitement take over.

Gradually, Gavin moved his mouth from hers and trailed down her neck and over to one of her breasts, where he slipped a nipple into his mouth. He knew how much this turned her on and he took his time about it before he moved to the other one.

As Gavin sucked her nipples, she could feel his erect member pressing against her thigh. She knew just how excited he was when she felt wetness on her bare skin. He continued to move downward on her body and didn’t stop until he was right between her thighs. His probing tongue parted the folds that hid her pleasure center and started to lick small fast circles around it.

Oh god, Daphne thought. I’m going to cum right now!

But just as she was climbing to her peak, Gavin stopped and flipped her over.

This was his first look at the back of her chemise. He moaned and growled a bit when he saw it and immediately reached for the lubricant she had bought. He parted her ass cheeks and applied it to the outer rim of her little back hole. Then he moved his finger inward so that she was totally prepared.

Next, Gavin took the little probe and very gently started to push at her puckered little hole. At first, Daphne tensed.

“Baby, I’ll stop anytime you want me to,” Gavin whispered to her. “Don’t be afraid.”

Those words made Daphne completely relax and as soon as she did, the probe slipped in with no effort.

“AH!” Daphne cried out. “Ohhh, that feels….I don’t know how that feels.”

“Does it hurt?”

“Oh no! It doesn’t hurt at all. It’s just a bit different. Keep going.”

So Gavin continued to move the probe in all the way and slowly drew it almost all the way out again. Soon, he was slowly and gently fucking her in that manner. As he did so, he also reached between Daphne’s legs and started to stroke her engorged little clit. That seemed to be just the right combination of stimulation for her.

“Gavin,” Daphne gasped. “Please fuck me now! I’m ready!”

“Are you sure, baby,” Gavin asked with ragged breaths.

“Yes, I’m sure! Do it now!”

Gavin withdrew the probe and moved her onto her hands and knees where he was able see exactly what he was doing. Then he took his steel rod and started to push against her opening as gently as he could manage. Just to be on the safe side, he added more lubrication because he was quite a bit larger than that tiny probe. That did the trick because he was able to slide the head of his cock right into Daphne with only a bit of pressure.

Daphne felt a little bit of stretching at her back hole and stiffened again. But when Gavin stopped, she relaxed once more and moved her ass back towards him a little. This helped him to push into her more and was also very much of a turn on as he looked down at her luscious round ass cheeks moving back and forth on his cock.

Soon, he was all the way inside her and could feel her velvety ass walls closing around him like a glove. Gavin had never felt anything like it before and he was close to exploding after only a few seconds of this.

To regain his control, he focused on reaching between Daphne’s thighs again and starting to play with her clit once more. He was rewarded with a shattered sigh and long moan from her as he found that she was literally soaking wet.

When Daphne’s orgasm slammed into her suddenly, she involuntarily moved back and forth on Gavin’s cock. She never felt anything except the fullness inside her ass and the electrical currents of pleasure that were jolting through her body. This orgasm seemed to go on and on.

When she felt Gavin lose control and start to spasm inside her, she started to cum again. She rode his hand in the front of her and his cock behind her. She had never felt such a sensation.

When it was over, Gavin gently eased his cock from Daphne’s backside. They both were still gasping for air as they collapsed onto the bed.

“So,” Gavin finally managed to say. “What did you think?”

Daphne reached into her nightstand and handed him a small gift wrapped box. Gavin opened it to find a small key shaped pendent on a light gold chain.

“Let’s just say,” Daphne replied, “that you’ve earned the key to my back door.”

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