Jessica's Anal Curiosity

"Maybe a little bit of both," he replied after some thought. "I'm busy with work, so I would make a terrible boyfriend. That's the main problem I have with relationships I think."

"I can relate. When I'm somebody's girlfriend, I treat it like a full time job. I'm really busy with law school, so I know what you're saying."

"Seems like we're both in the same boat when it comes to dating."

"Seems like it," she agreed.

"It's also hard to find a connection with the right person. That's very important to me."

"I agree wholeheartedly."

Dave nodded. "Speaking of past relationships, Amy mentioned that your previous attempt at anal sex with an ex-boyfriend was a disaster."

"God, it was. We were so inexperienced at the time. His idea of lubrication was spitting on his hand and rubbing it on his penis. In hindsight, that was part of the problem- no pun intended."

He laughed, "I like you. You're a quirky girl."

"Thanks I guess."

"Now that we've gotten the mood lightened up, shall we begin?" he asked.

"One more question. Why do you help women with anal sex? Do you have some sort of anal fetish where you masturbate after the woman leaves? Or are you putting your medical talents to good use in a charitable way? Maybe both?"

Dave thought for a moment. "I've always been opened minded when it comes to sex. And I've always been curious about anal sex with a woman. When I went through med school, women were complimenting me on how seamless anal felt with me compared to their past experiences. Apparently I have a soft touch. The rest is history."

"Oh, so you're some sort of anal sex expert."

"If that's how you see it, then sure," he smiled. "My bedroom is right behind you. I have everything set up."

Jessica turned around and saw the bedroom door open. She walked towards the room with Dave following her lead. Once she entered the bedroom, she saw a large towel spread neatly across the bed. There were also containers of lubrication, vaseline, and a few items which looked like small sex toys.

"Looks like you've got everything prepared," she noted.

"I'm a doctor. We're taught to prepare. Everything is clean and sterilized."

"That makes sense."

Dave smiled, "I'll need you to remove your panties now."

She took a deep breath while she reached underneath her sun dress to pull her white panties down. Her face remained expressionless because she was so nervous. Once her panties were around her ankles, she bent down to pick them up, and she handed them to Dave.

"You follow instructions well," he said, folding the panties and placing them on a table counter.

"That's why I'm here isn't it?"

"Exactly. Now I need you to get on all fours on top of the bed, above the towel."

Once again, Jessica followed the instructions without hesitation. She got on her hands & knees and crawled on the bed until she was perfectly in the center, with her body over the towel. She knew what to expect and she rested her face on the bed, with her rear end pointing in the air. The dress still covered her behind.

With her head still on the bed, it was obvious that Dave was right behind her because the bed moved. A gasp escaped her lips the moment she felt Dave's warm hands touch the lower part of her thighs.

"Are you okay?" he asked.

"Yes."

Her response was short and simple. It was all the consent Dave needed to continue.

In a swift movement, Dave lifted the bottom of Jessica's blue sun dress and tossed it over her back. Her bare ass and backside were completely exposed. She felt vulnerable, but she didn't flinch. It was the exact reason she came for, and she knew it. With her legs spread apart, she knew Dave had a clear view of her shapely rear end, along with a clear view of her anus. There was no talking or movement for a period of time, and she knew he was examining her with his eyes.

A pair of hands rubbed her backside in a caressing manner. It felt nice, and she appreciated the fact that he was being gentle and taking his time. A pair of lips pressed against her left butt check. Then the lips pressed against her right butt cheek. He planted more kisses on her rear end.

"Your arousal is very important," he said, as if knowing what she was thinking. "Being aroused means your body and anus will relax. Then we'll start. It'll be slow today. Step by step."

Dave continued kissing her rear end. The kisses moved closer and closer to her tiny little anus. For a moment, she thought he was going to kiss her anus directly, and she prepared herself for it. But the feeling never came. The kisses stopped.

Jessica heard the top of a small bottle being opened. It must be lubrication, she thought. Without waiting any further, she felt his finger press against the delicate skin of her anus. The finger was coated with something, and it was slightly cold, which made her flinch.

"No gloves?" she asked during the awkward situation.

"I don't use gloves for this. I prefer a more personal touch. Besides, if it's one thing I've learned as a doctor, people don't feel comfortable being touched by rubber gloves."

With that said, he pushed his finger inside, penetrating her rectum. Jessica remained expressionless as the finger probed her small hole. She tried her best to stay relaxed. It was uncomfortable, but it didn't hurt. Her body was slowly adjusting to the index finger inside of her asshole. The finger continued probing and rolling around inside of the rectum.

As her tight little hole began to adjust, another finger was inserted inside. She wanted to gasp, but she held it in. It was a bearable feeling, and she accepted it. The fingers moved in and out, and she was becoming accustomed to it. There was plenty of lube, and that made things easier. Before she could get used to the feeling of two male fingers inside of her butt, the fingers left.

"How are you feeling?" he asked.

"It wasn't that bad. I was getting used to it."

"Are you ready for something bigger?"

"I'm as ready as I'll ever be," she replied.

"Good. The object is small. We'll see how you handle it."

Dave spread her anus using his fingers from one hand, and with his other hand, he inserted a long & thin object inside. He inserted it slowly and gently. Based on the small movements Jessica's body was making, he could tell she was becoming uncomfortable.

"Let me know when you want me to stop," he said.

"Okay."

He continued slowly pushing the small object inside of her asshole. He observed the stretching of her anus while the object was penetrating her rectum. Once it was all the way in, she gasped. Her body flinched.

"Stop," she gasped. "That's too much."

Dave pulled the object out of her asshole and placed it on the towel. He then covered Jessica's bare ass with her dress, and she knew it was the end.

"You can sit up now," he said. "Now we know your limit. That was 5 inches, and fairly thin."

Jessica sat on the bed. "Is that good?"

"For someone as tight as you, I think that's real progress."

"Glad to hear it."

"I'll wash the object so you can take it home and practice. I'll also give you lube which we use in the hospital. I want you to use it tonight, exactly the way that I did. If you have free time tomorrow, maybe we can meet again."

"Doctor's orders?" she asked playfully, with an eyebrow raised.

He smiled, "Those are doctor's orders."

*** OBJECT OF SEXUAL AFFECTION ***

Later that evening. Jessica ate an early dinner while watching tv. After cleaning the dishes, she brushed her teeth and wore her night gown. The sex object that Dave had given her was placed upright on a small table next to her bed. The object almost had a hypnotic effect on her and she couldn't take her eyes away from it.

It was 6:45 pm. She knew that Amy's date would pick her up at 7. At that point, Jessica needed someone to confide in. She couldn't wait until later that night, or the next day, so she picked up the phone and called her friend:

"What's up Jess?" Amy answered on the phone. "Did you meet him today?"

"I did. That's why I'm calling."

"Awesome. So how was it? Did you like it?"

"It was definitely an unusual experience. But I liked it. You were right about Dave, he's a great guy."

Amy laughed. "Do you like him?"

"Obviously."

"I mean do you like him," she asked again. "I can hear it in your voice. Are you falling for this guy?"

"Maybe a little," Jessica admitted. "But I'm realistic about it. He's got a good thing going being a single bachelor, and I don't think he's looking for a girlfriend."

"You never know. You're a pretty good catch Jess."

"Thanks."

"So how far did you two go with the whole anal thing?"

"Two fingers at first," Jessica stated. "Then he used a small object on me. We stopped once he put it all the way in. I told him it was too much for me."

"Congrats. You went further than I did my first time."

"Really?"

"Yes really," Amy replied. "Did he give you the object to take home?"

"Yep. I'm looking at right now, but I was afraid to do anything with it."

"After everything you've done today, it should be a lot easier. Just lube it up and shove it in. It's as simple as that."

Jessica laughed. "Easy for you to say. I guess I can only do it when I'm aroused. That's the key, as Dave put it."

"Then call him. You have his number don't you?"

"Yeah, I have it."

"Call him," Amy said again. "I think my date is here now. I've gotta go."

"Bye. Have a great time."

"Thanks. Bye."

***

After they hung up the phone, Jessica's eyes remained on the sex object. So far, everything Amy said was right. She had no reason to doubt her friend. Everything David had said was correct as well. Both of them knew what they were talking about, she thought.

With the phone still in her hand, she called Dave:

"Hello."

"Hey Dave," she replied. "It's me. Jessica."

"I know," he said happily. "What can I do for you this evening?"

"Oh, nothing. I just wanted to see how you were doing."

"It's always good to hear from a patient," he joked.

"You think of me as a patient huh? Well that makes me feel good," she joked back.

"So how are you doing? Have you used the object I gave you?"

Jessica paused for a moment. "Actually, I haven't yet. It's on the counter next to my bed and I've been staring at it for the longest time."

"What's the problem? Do you still have anxiety over anal sex? Or is still uncomfortable."

"Both. The thought of putting that long thing inside of my butt still kind of scares me. And as you can imagine, it doesn't feel very comfortable."

"That's very understandable," he replied. "Especially in a butt as tight as yours."

"You think so?"

"I've given plenty of prostate exams. I know a tight butt hole when I see one."

"So you can see why I'm so apprehensive about all this," Jessica replied.

"I understand. But I also thought we made significant progress this morning in my apartment since things seemed to be going smoothly."

"We did make progress," she said playfully. "Before we met, there was no way an object as long as that would have been inside of my ass."

"So what changed?" he asked.

"Well, I trust you with my body. And I feel comfortable around you. I really like you."

There was a sudden pause on the phone. She quickly realized what she said, and the way she said it. Dave knew immediately how she felt about him.

"I really like you too."

"This is awkward," she blurted out.

Dave laughed, "There's no need for awkward feelings. Especially since I've already seen the inside of your rectum. You're beautiful inside & out, literally."

"Sheesh. Now this is getting embarrassing."

"Let me ask you something," he said. "When you were on my bed, with your bare ass exposed, how did that make you feel?"

Jessica thought for a moment. "The same feeling I get when I'm having my breasts or vagina examined by a medical professional. It was the same feeling."

"What else?"

"Aroused," she admitted. "I felt aroused."

"Tell me why," he said.

"I think because of how submissive that whole thing was. It was the most submissive thing I've ever done in my life. I barely know you, but I was on your bed, naked from the waist down. It was thrilling in a strange way."

"I love when women are honest with themselves, and with their sexuality. That's what I enjoy the most doing this. Finding that honesty."

"Then you must be satisfied, because that was the truth."

"What are you wearing?" he asked.

"A night gown."

"Panties?"

"No."

"Good," he replied. "I want you to grab the lube I gave you, along with the sex object."

Jessica walked a few feet towards the bedside table and held the object in her hand. The lube was still on the table. Just within reach.

"Okay," she said. "I'm holding it."

"Use the speaker on your phone and place it on the bed so I can hear you. Now I want you to lube object."

Jessica turned on the phone's speaker and placed it neatly on the center of her pillow. She then picked up the brand new bottle of lube and applied a generous amount of coating onto the sex object. After a quick glance, she knew she would need more and applied it liberally. Her fingers were covered in lubrication, and she held the object with her hand.

"It's about as lubed up as it can get," she stated.

"Excellent. Do you typically use sex objects when you masturbate?"

"Sometimes in the shower I'll use the end of my hairbrush. I normally use my fingers though."

"That sounds fairly normally," he said, as if analyzing a patient. "Anal masturbation isn't appreciated by many women, but if done correctly, it can be quite sensational."

She smiled to herself. "You sound like you've helped plenty of women with this."

"I have."

"And you think it'll work for me?"

"We're about to find out," he replied. "I want you to put a good amount of lube on two of your fingers, and rub it around the ring of your anus."

Jessica did as she was told, opening the bottle of lube once again, and bending over so she could apply it on herself. Her fingers traced the soft skin of her anus while she applied the lube.

"It actually feels kind of nice," she said playfully.

"It's about to feel better. Stick your fingers inside and coat the rectal passage. You don't have go all the way in, just add enough so that the object can enter with ease."

Once again, Jessica did as she was told without hesitation. Her two fingers entered her tiny hole and the lube coated the entrance of her rectum. It was the first time she had ever had her fingers inside of her anus, and it was excited in a strange way. When she finished, she pulled her lubricated fingers out.

"I did it."

"Now press your face on the bed. I want your ass pointing in the air."

Jessica assumed the position and pressed her face against her bed. Her knees were also on the bed, and she pointed her ass upwards, with the sex object still in her hand.

"Okay," she said.

"I think you know what to do next. It isn't that hard Jessica. You just have to be willing to accept it inside of your body, and be aroused while it happens. Let me hear you do it. Pretend that I'm there with you."

After a deep breath, Jessica reached back with the sex object in hand, and pressed the tip against the soft skin of her anus. One more deep breath, she pushed the object inside of her until it penetrated her tight little hole. A gasp escaped her lips and she knew Dave must have heard it.

"Good girl," he said. "Don't be afraid."

Despite the pain and uncomfortableness, she continued pushing the object in. The excessive amount of lube made the entry easier. Slowly it made its way in, before eventually entering all the way.

There was a sense of an exhibitionist rush for Jessica. Not only did she had a foreign object up her ass, but she was doing it while someone was listening and guiding her over the phone. At that point, there was no doubt in her mind that she was beginning to fall for him, and there she was, pleasuring herself for him.

"It's all the way in," she stated.

"Pull it out, slowly, and then slowly re-insert it."

Jessica did as she was told and began to masturbate anally with the sex object. She pulled it out slowly as instructed, then she pushed it back in. To her surprise, it was beginning to feel good. It was also the first time in her life that her pussy became wet from anything going inside of her ass.

"What are you thinking about?" he asked. "I can hear you breathing harder."

She continued pleasuring herself. "Us together. I'm thinking about you being here."

"You want me there with you?" he asked, already knowing the answer.

"Yes."

"Do you want me using the toy? Or something else?"

"Something else."

"Do you want me to fuck you?" he asked bluntly.

"Yes," she moaned. "I want you to fuck me."

Jessica furiously used the sex object in-and-out of her lubed asshole. Her other hand went to her pussy, which had become dripping wet, and she fingered herself. She became lost in the moment and masturbated like she never had before. Both of her holes were being used in salacious ways, and her asshole was stretched and abused.

"Oh god!"

Her back arched and her body flattened on the bed. She continued masturbating her asshole and pussy. She came hard. It was the best orgasm she had in several months, and it was much needed.

When it was over, she freed her arms, with the sex object still inside of her butt.

"Well done," he said. "I'm impressed. I didn't think you were ready for something that."

"Tell me about it," she said, breathing heavy.

Jessica finally regained her composure and pulled the object out of her ass, and she sat upright on the bed.

"Listening to you masturbate was the most erotic thing I've heard in a very long time."

"You have no idea how badly I'm shaking over here," she replied. "That was so intense. Thank you Dave. I really needed that."

"There's no need to thank me. You were the one doing all the work."

"But it was thanks to your guidance. Can we meet sometime soon?"

He smiled to himself. "How about tomorrow morning?"

*** RAVISHING THE GOOD GIRL ***

Jessica walked through the downtown area as if she was taking a casual stroll. She wore a yellow sun dress with shoes that were easy to slip off. Butterflies were in her stomach and she felt slightly more nervous than the first time she visited Dave's apartment. She knew him better now, and she liked him more. She knew that he liked her also. There was no doubt in her mind that a special relationship was forming between them, and that it was beyond what both of them had expected.

She knocked on his apartment door, and Dave greeted her with a smile.

"It's nice seeing you again," he said. "You look beautiful."

"Thanks. You too," she blushed.

Jessica walked inside of the apartment and took off her shoes, while Dave closed the door.

"Last night on the phone was something new for me. I've never listened to a woman pleasure herself like that before. I thought it was very erotic."

She nodded. "That wasn't planned at all. I called you because I wanted to talk. Then it kind of just happened, and I'm glad it did. It was amazing."

"Well I'm glad to be of service to you. I'm sure we can find something interesting to do this morning."

"Look, before we start, I want you to know that I have a tendency to fall for guys too soon. It's a bad habit of mine. I'm a relationship kind of girl. So whatever this is between us, please let me know so I can tamper my expectations."

Dave smiled and put his hand on her shoulder. "I think you're wonderful. Honestly. I think you're a special person."

"So you're not interested in me beyond this. It's okay. I totally get."

"I didn't say that," he replied.

"Then what are you saying?"

"I'm saying, let's take things slow and see what happens. I think you're an amazing girl. I've thought so since the moment we met."