Loading...Jessica was new to the city.
She was a fresh faced 24 year old from the suburbs who recently moved to San Francisco to attend law school. It was the first time in her life that she lived on her own. Being away from her family was hard. None of her friends were there with her, and she didn’t know anybody at her new school.
Dating in a big city was daunting to her. She was old fashioned at heart, and raised to be traditional. As pretty as she was, Jessica didn’t feel good enough to compete with women in the city. She knew expectations from men were high. They expected a lot, and sexually she had her own limitations.
But like always, she was curious.
Jessica’s Anal Curiosity
Several months later. Jessica and her new friend Amy were taking a break in-between classes. They bought coffee and sat down so they could relax. Downtown in San Francisco was always busy during the day. Everyone was always in a hurry to get where they needed to go, but at that moment, the two friends took the time to relax.
“Apparently they’re going to post grades soon,” Amy sighed. “I’m terrified of the results.”
“I know what you mean,” Jessica replied. “But I’m sure we both did well.”
“Easy for you to say. You’re the smartest girl in class.”
“I highly doubt that. But thanks for saying it.”
“It’s true. There’s a reason why the teacher calls on you all the time. It’s because you always have the right answer.”
Jessica blushed and became uncomfortable with the high praise. She had always been smart, along with being an excellent student, but she was also modest.
“There are still tickets available for that musical on Saturday,” Jessica said, changing the subject. “Do you want to go? It would definitely take our mind off of everything.”
Amy smiled, “I can’t. I have a date that night.”
“Really? With the guy you’ve been flirting with? You never told me that.”
“I was about to. He finally asked me out this morning and I said yes.”
“Wow. That’s great. He’s pretty cute too. I expect to know all the details by Sunday morning.”
“Ask and you shall receive.”
“I’m really happy for you,” Jessica said. “I know how much you like that guy.”
“I do. Speaking of which, how come you’ve never dated anyone since you moved to San Francisco? There are plenty of guys here who are interested in a cutie like you.”
Jessica blushed. “I don’t know. I’m pretty busy with law school and everything.”
“Everyone’s got a busy schedule these days,” Amy replied. “That’s not an excuse.”
“I’m picky when it comes to men.”
“Then you must be really picky because I’ve seen some handsome guys ask you for your number, only to get shot down. What gives?”
Jessica paused for a moment. “Honestly, I’m a little intimidated by dating in the big city.”
“That’s a first. I’ve never heard that before.”
“Well I don’t expect you to understand since you’ve lived here your whole life. But I grew up in a quiet area with small college. Things are a lot different here.”
“That kinda makes sense,” Amy nodded. “I used to live in a small community before my family moved here when I was ten. So I totally get it.”
“Yeah. I’m used to things being simpler, that’s all.”
“Simpler in what way?”
“Sex,” Jessica replied. “I’m use to taking things slow. And I’m uncomfortable with that other thing that guys are becoming accustomed to. I hear all the girls do it now, and it’s scary to me.”
“What other things? Do you mean that bdsm lifestyle or swinging? Just because we’re in San Francisco, doesn’t mean everyone is involved with that scene.”
“Not that.”
“Then what? You don’t give blowjobs?” Amy asked bluntly.
“I don’t have a problem oral sex. It’s anal. I’m afraid that a guy would be disappointed if I don’t provide anal intercourse for him.”
“Oh, that makes sense. Lots of small town girls don’t do that. There’s no shame in being an ass virgin.”
“I’m not exactly an ‘ass virgin’. I tried it with my ex boyfriend in college and I hated it. It was pure agony for me and my body isn’t built for it.”
“No big deal,” Amy shrugged. “Just tell the guy you aren’t interested in doing that. Problem solved.”
“The thing is, I fall for guys easily. My biggest fear is that I’ll start becoming attached to someone, and once we get close to enough to start having a sexual relationship, he’ll be turned-off by the fact that I can’t do anal. He’ll eventually dump me for other girls who can.”
“You think way too much Jessica.”
“I’m being realistic,” she replied. “Don’t you think a modern guy would dump a girl if she didn’t perform oral sex on him? It’s the same thing with anal sex.”
“I don’t think so. A blowjob is practically required nowadays. Butt sex is an elective. It’s something couples do if they want to try something else for a change. It’s not required by any means.”
“Yeah, but blowjobs used to be an elective a long time ago,” Jessica replied. “Times changed and now blowjobs are required. Anal sex is becoming the same thing.”
Amy nodded. “I’m starting to see your point.”
“Then you realize that I’m doomed to never date a decent guy in the city because I can’t provide what other girls can provide.”
“You’re still exaggerating,” Amy said. “Look, what if I told you that I knew a guy who could help with your little problem?”
“So you’re setting me up on a date with a guy who doesn’t want anal sex? Sounds romantic.”
Amy smiled and held back her laughter. “No. Believe it or not, I used to have the same problem you did with anal sex. I was scared by it, and whenever I tried it with a guy, it hurt like hell. So I know how you must feel.”
“Really? What changed all that?” Jessica asked.
“A couple of years ago I was chatting on an internet forum and I met a guy who was in med school, he’s a doctor now. We talked about sex mostly. I told him my problems and then he mentioned his medical training. Apparently the things he learned in med school helped with him being able to make the whole anal experience a lot easier.”
“You met a guy online?”
Amy nodded. “Yep. And trust me, I never meet anyone online. I made sure he confirmed his identity by having him email me with his hospital account. Everything checked out and we met each other for coffee. Afterwards we went to his apartment, and the rest is history.”
“That sounds pretty interesting. That look on your face means it must have been a real success.”
“It was,” Amy grinned. “Big time. So are you interested?”
“In meeting him?”
Amy nodded again. “Yes, would you be interested in meeting him? He’s a sweet guy, trust me.”
Jessica suddenly became nervous. “I don’t know. I’ve only been with four guys my entire life. And all of them were serious relationships.”
“I’ll tell you what; I’ll email him today explaining your situation. Then I’ll give him your email address so he can contact you. If you like what he has to say, and you’re interested in meeting him, then you can reply. If you’re not interested, then just ignore him.”
“Fine. That sounds fairly reasonable.”
“Great,” Amy smiled. “Trust me on this, you’re really going to like him.”
*** OPEN MINDED YOUNG WOMAN ***
Jessica finished her homework for the evening. Despite the busy day, she couldn’t stop thinking about what would happen if she received an email from Amy’s friend. It was all she thought about. Anticipation was in the air. She wondered if she could actually go through with it given the chance. She constantly checked her email, even her spam box, to see if she had received any new messages. So far there was nothing.
It was 7:15 pm and she was about to log off and eat dinner alone in her small apartment. Before she closed the computer, she received a new email. The subject line simply read, “Hello.” She clicked and read the email:
Hi Jessica,
I hope you’re doing well. My name is David. We’ve never met before, but I’m Amy’s friend. She recently emailed me explaining your situation, and I am interested in helping. I hope I’m not being too direct in saying that we could meet in person to explore things further. I have been with several women who have all been curious about anal sex in some way. So far my track record is perfect, otherwise your friend Amy wouldn’t have referred me.
Let me know if this sounds appealing to you. I would be more than happy to help.
David
At that moment, her head felt like a melting pot of mixed emotions. The opportunity to try anal with someone with real experience was right in front of her. All she had to do was answer- yes or no. It was that simple.
Jessica froze thinking of how she should respond. Knowing herself, she would have replied with paragraphs upon paragraphs if she didn’t filter her response. She didn’t want to look desperate, needy, or weird. So she tried her best to keep the response short and simple. She replied to his email:
Dave,
Thanks for the nice message. How did things go with Amy? What makes the whole anal thing work so easy for you?
Jess
She sent the message and immediately regretted it. She thought the email was too short, which made her look uninterested in meet him. Deep down, she was very interested. Instead of eating dinner, she sat in front of the computer for 20 minutes waiting for a reply.
A new email appeared. It was from David and she immediately opened it:
Thanks for the reply. It’s nice to see that there are more open minded young women like you out there. I usually don’t like discussing what I do with other women because I’m very discreet.
But what I do that makes the “anal thing” work so well is that I make sure that she’s relaxed and comfortable. A lot of men don’t take the time to do that. I also make sure that she’s sexually aroused first. That’s a very important and overlooked part of anal sex.
I work a full time job and I understand that you’re busy with law school. It wasn’t that long ago that I was in med school, so I know the daily grind. Let me know when you’re free to meet. Having a cup of coffee together always works well. Again, I don’t want to pressure you. I want this to be on YOUR terms, not mine.
Dave
At that point, Jessica’s heart started beating. The chance to have a casual sexual encounter was offered in front of her on the computer screen. All of her previous relationships were with men she deeply cared about, and had been dating for some time. This was new to her.
She decided that she definitely wanted to meet him. He seemed like a nice guy in a city where nice guys were hard to find. The thought of having someone to train her sexually was arousing. An excitement came over here which she hadn’t felt since the moment she got accepted to a top tier law school. She knew she had to meet him, and soon. She replied to his email:
David, I’m very interested in meeting you. Amy has said a lot of great things about you. She’s told me which hospital you work, and that there’s a coffee shop across the street where you two had previously met. Maybe we can meet there for breakfast? My treat. Sorry if I’m rushing things. I’m just a little excited (and nervous if you couldn’t already tell). If you’re busy, let me know if want to change the schedule.
Jess
After she sent the email, she quickly received a replied:
In front of my hospital sounds great. Breakfast, 8am. See you then.
Jessica let out a loud sigh in her small apartment. A meeting was set. Early the next morning she would meet the man that her friend recommended for anal sex. Butterflies were in her stomach and she had a giddy feeling.
Instead of eating, she turned off the computer and ran to closet to look for the sexiest outfit she had. But it didn’t take long for Jessica to realize that she didn’t have any sexy outfits. That wasn’t the type of person she was. Instead, she laid out her clothes for the next day, which consisted of a modest looking attire. It was modest, but classy. She was a smart girl who was about to explore her sexual side. She had to look good.
*** DRESS LIGHT & CLEAN YOUR BODY ***
Jessica woke up much earlier than usual and waited at the cafe since 7:30. Being early and prepared was the type of person she was. By 7:55, she waited in a long line and bought two cups of coffee and some pastries so that they could have breakfast together.
By 8 am sharp, David showed up exactly on time. He spotted the nervous girl immediately and made his way towards her. Sparks were flying the moment their eyes connected. There was an immediate connection between them.
“You must be Dave,” she said, extending her hand for a handshake.
“That’s me. You’re obviously Jessica.”
The shook hands and smiled at each other. David was more handsome than she expected. While they shook hands, all she could think about was his good looks as she stared at his face. His body was physically fit. He was tall, dressed with class, and had a friendly demeanor.
“Have a seat,” she said, trying to hide her nervousness. “I bought us breakfast.”
“Thanks. I like being the one who pays for food. I’ll buy next time.”
They sat down and David took a sip of the coffee she bought him.
“So how did you know I was the person you were supposed to meet?” she asked. “Did Amy tell you what I looked like?”
He winked at her. “I could tell because you looked nervous. Besides, you were sitting here alone with two cups of coffee, and food for two people.”
“Oh, right.”
“And you look exactly how I imagined you would look,” he said.
“How did you imagine me?”
“Well, you attend a good law school, so I knew you would look smart. You mentioned you were nervous in your email, and you sounded like a woman with manners. So I knew you had class, and that you’re typically a modest person. Finally, Amy only hangs out with pretty girls. So I knew you had to be pretty. So when I saw you a moment ago, I knew it was you.”
Jessica smiled, “Smart guy. No wonder you’re a doctor.”
“Thank you.”
“I normally don’t do this,” she said. “Most of my experience with men has been during serious relationships, and I’ve only had four. So this is new to me.”
“Amy mentioned that aspect. I think it’s great that you have an open mind. Most women don’t.”
Jessica politely nodded, unsure of what to say next. There was an awkward silence between the two strangers, and they politely continued to smile at each other in the busy cafe. They each took a bite of their food, and took drinks of their coffee.
“So what happens next?” she asked, before taking another sip of coffee.
“Next, we meet at my place when our schedules are free. I’m assuming that at this point, you definitely want to do this.”
“Yeah, I think so. You seem like a great guy, and Amy speaks highly of you. If she can trust you, then I can trust you too.”
He smiled, “Great. I like that attitude. Obviously I’m very busy on the weekdays, so how about on Saturday? We can take our time.”
“That makes sense. How about 10 am?”
“Perfect. The only thing I ask is that you dress light, and obviously I want you to clean yourself before coming over. I’m sure you know the area I’m talking about.”
“I can do that,” she replied.
“Thanks again for the breakfast and coffee,” he said. “It was so nice to meet you. I have a feeling that we’ll get along just fine.”
Dave stood up and kissed Jessica on the forehead. It was a soft and tender kiss. His hand patted her on the back, and then he left. She sat there alone and quietly finished her coffee. An exhilarating feeling rushed through her body. The thought of having a casual sexual encounter with Dave excited her.
***
Later that afternoon. Jessica and Amy once again took their break together in between classes. They casually and slowly walked through the city in a relaxing manner. Amy was eager to hear about her friend’s first meeting with Dave.
“So what did you think about him?” Amy asked.
“I really like him,” she replied. “He seems like a decent guy. Handsome. And I think he seems trustworthy. I wouldn’t be doing this if I couldn’t trust him or if I thought he was a sleaze.”
“I agree. It took me a while before I decided to meet him, months I think. I was apprehensive, and then when we first talked on the phone and met, I was all for it. I think he’s awesome.”
“Any hints for what I can expect at his place?” Jessica asked.
“He’s got a nice apartment. It’s nice and clean.”
She flashed her friend a playful look. “You know exactly what I mean Amy.”
“Oh that,” Amy smiled. “Did he tell you anything about it?”
“Only that I should dress light and to make sure my ass is clean.”
Amy shrugged. “That’s about all you need to know. Seriously, all you have to do is relax and let him do the work. Nothing else. He’s a real expert at what he does. You’re literally in good hands.”
“Thanks for the reassurance.”
“You’ll be fine.”
“So what does it feel like?” Jessica asked. “Does it still hurt with him?”
“A little bit. But not as much as with anyone else. It feels good after a while, and before long you’ll have your first anal orgasm. Believe me.”
Those words struck Jessica and she was taken aback. How anyone could have an orgasm from anal penetration was beyond her.
“As long as it doesn’t feel like my first anal experience, I’ll be happy. God, this is so scary.”
“Will you stop worrying already?” Amy asked playfully. “I want you to trust me. By the time Dave gets done with you, you’ll be a bonafide anal lover.”
She sighed, “Thanks I guess.”
*** BLUE SUN DRESS & CASUAL SHOES ***
It was Saturday morning and Jessica woke up early and took a long shower. She used more soap and shampoo than she normally would. More importantly, she used the movable shower head to wash her anus while she squatted down in the bathtub. She wanted her rectum to be as clean as possible for Dave, and she even used her soapy fingers to clean in the insides. Afterwards she brushed her hair neatly and applied moisturizer on her already skin.
After a small breakfast, she wore a light outfit as recommended; a light blue sundress with casual shoes on her feet. Everything was easy to slip off.
She left her apartment and waited for the bus. She wasn’t as nervous as she expected to be. The trip was like visiting the doctor, she thought to herself. After a short wait, the bus arrived and took her to the downtown area where Dave lived. He wasn’t rich, but he lived in fairly nice area of downtown San Francisco.
Once she reached his apartment, she knocked on the door was greeted by Dave. He dressed casually and had a big smile. The mood was awkward, yet much more relaxed than their first meeting. They hugged and she entered. She took off her shoes. Her eyes wandered around his home.
“Nice place,” she said. “It’s a lot nicer than I expected.”
“What did you expect?”
“I don’t know. I expected a messy place since you’re a single bachelor.”
“And what makes you think I’m a single bachelor?” he asked seriously.
A mortified look came over Jessica. “You’re not single? Oh gosh, I’m sorry. I should be leaving now.”
“I’m only kidding,” he laughed. “Stay. I want you to feel at home.”
Jessica smiled, “Very funny. I was seriously about to leave if you had a girlfriend or something.”
“Well, you seem like a woman with integrity, so I don’t blame you. Cute outfit by the way.”
“Thanks,” she blushed. “You told me to dress light, so I did.”
“I can see that.”
“So, how should we proceed?” she asked awkwardly.
“Would you like some water or juice first? Anything to make you feel at ease?”
“I’m fine. But now that you mention it, there is something you can do for me.”
“Besides anal?” he joked.
She playfully responded, “Yes, besides anal. I’m curious, what’s a handsome young doctor like you doing being single? Do you prefer the single life? Or are your standards ridiculously high?”
“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.”
She winked and nodded. “Okay. I believe you. Shall we get started now?”
“Sounds like a plan,” he replied, extending his hand for her to hold. “Follow me.”
Dave lead Jessica to his bedroom. Once there, her eyes surveyed the room. The bed was neatly arranged like before, with an open towel in the middle along with lubrication- nothing else.
“There aren’t any sex toys on the bed,” she asked with an eyebrow raised.
“Maybe we won’t be needing them today.”
Jessica smiled, knowing exactly what he meant. There was an obvious tension in the room, and she found herself becoming increasingly aroused.
“Is this because of that comment I made last night about wanting you to fuck me?” she asked playfully.
He playfully shrugged. “Maybe. Maybe not.”
“That comment was during heat of the moment. I was masturbating remember? I don’t think something like that should be taken very seriously.”
“Well, I do remember that you were masturbating. But in my professional medical opinion, it sounded like you were serious. So I think I’m going to have to do something about that.”
“Doctor’s orders?” she asked, raising her eyebrow again.
“Yes, Jessica. Those are doctor’s orders. But first, I’m going to need you to remove the dress.”
A sudden rush came over her. She was very aroused, and her heart began to pound. Jessica lifted her yellow sun dress and pulled it over her head, tossing it to the floor. She wore a bra, but was naked from the waist down. She came to his apartment without any panties on, and he was admiring her almost nude figure.
“Will this suffice?” she asked teasingly.
“I’m afraid not. The bra must be removed as well.”
She reached behind herself and unclasped her bra, tossing it to the floor. Her small perky breasts were exposed. They were upturned with pink nipples, which began to stiffen from sexual arousal.
“Looks like I’m naked,” she said.
His eyes looked up and down. “If I had known you looked this good naked, I would have undressed you a long time ago.”
“So what next?”
“I’ll need you to assume the position on the bed. It’s time for your exam.”
She gave him a wink and climbed onto the bed on all fours. Once her body was above the towel, she rested her head on the blanket, and pointed her ass in the air. The sound of a bottle opening got her attention. Dave was opening the lubrication, and the anticipation was building.
Feeling his soft fingers against her anus sent a shiver down her spine. She could feel him apply a large amount of lubrication. He wasn’t as gentle as before. After he coated the outside of her little hole, he pushed his fingers inside to coat her rectum.
“We’re going to do something a little different today,” he said, with his eyes on her ass. “So I need you to be more aroused than usual. Do you mind?”
“If that’s what you think is best, go for it.”
Without another word, Dave pressed his mouth against her vagina and began to lick. Jessica was caught off guard and wanted to shout, in a good way, but she held it in. It felt good. She loved the feeling of Dave’s tongue running up and down her labia, and flickering around her clitoris. He licked as if he was waiting years to do it, and she appreciated the feeling. It had been a while since Jessica had a man pay that much attention to orally pleasing her.
Once he was done licking, he began to suck her little clitoris, and he sucked her labia inside of his mouth. His tongue went inside of her pussy and she groaned. All the while his hands rubbed & caressed her backside. He kneaded her ass like dough while he ate her pussy. When he decided she was aroused enough, he stopped.
Jessica’s face was still on the blanket, and she couldn’t see what was going on behind her. A part of her was disappointed when Dave stopped performing oral sex on her. But that feeling was replaced the moment he positioned himself behind her and pressed something against her anus. She knew immediately what it was. It was his cock.
Dave used his fingers to spread her anus and butt cheeks. Once her hole was spread, he used his fingers to guide his rock hard cock inside. The head of his penis entered, then he slowly pushed. He used his hands to hold on to Jessica’s hips.
“Oww…” she gasped.
“Relax. The difficult part is almost over.”
She felt him rub the lower end of her back as he continued to push his cock inside of her rectum. She had no idea how big his penis was since she had never seen it, so she didn’t know how much further it would enter. It continued going down her rectal passage, and she felt herself being stretched by the hard cock.
Dave’s hand returned to her hips and he pushed all the way in. His crotch touched her butt, and Jessica knew it was all the way in. He stopped for a moment. The delicate anus & rectum were given a chance to adjust to the foreign entry, and it was working. Every second that went by, the pain lessened, and she was becoming used to it.
“How do you feel?” he asked.
“Ready,” she replied with her face on the bed.
The cock in her ass was still slightly painful, but she was comfortable enough to proceed.
Dave squeezed her hips tight and slowly pulled out, giving her a false sense of relief. The amount of lube helped his cock exit with ease, and once he was almost out, he slowly pushed it back in, filling her rectum once again.
“Ohh my…” she gasped.
Her asshole was beginning to loosen. Her sexual arousal was nearing its peak. She was ready to be fucked by him.
Jessica pressed her face harder onto the bed while Dave began to ravish her ass. She began to love the feeling of his hands squeezing her hips to hold her in place. She tried her best to keep her body still while he was slowly fucking her. His rhythm was slow, but his pace was increasing.
Before long, Jessica was getting her ass pounded and it was pleasurable. It was pleasure she had never felt before. Her moans became louder. The room became filled with sounds of her moans, the bed squeaking, the wet sound of a lubed cock going in and out of a small hole, and the rhythmic sound of his crotch slapping her ass.
“Oh god! David! Fuck me!” she yelled.
Her asshole was stretched and had adapted to having the large cock inside of her body. There was a powerful sexual sensation in her ass while Dave pounded her as hard as he could. It was intense, and unlike anything she had ever felt before. She was reaching her peak sexually and on the verge of a climax, which Dave was able to sense.
He reached down and rubbed her pussy furiously. Jessica screamed. She was being fucked anally and her pussy was being pleasured by Dave’s fingers. The sensations were becoming too much to bear and she continued screaming from the intense sexual feelings.
“I’m cumming! Oh god!”
Fluids shot from her pussy and onto the prepared towel below her. It was as if being fucked in the ass opened the floodgates for her first squirt. She tried her hardest to maintain her composure while Dave continued pounding away at her tight asshole. She came hard. The fluids continued squirting onto the towel while Dave continued fucking her and playing with her pussy. Dave’s fingers were dripping wet from her squirt.
The squirt eventually lost its power while he continued ravaging her asshole, but fluids were still dripping from her pussy like a leaky faucet.
It wasn’t long until Dave began to grunt and moan. He fucked her even harder. Then he shot load after load of his own cum deep inside of her rectum. His cock continued plunging in-and-out of her ass. Each time his cock would pull out, there was more and more white stuff visible on his cock. His own cum was providing additional lubrication.
When it was all over, Dave collapsed on top of Jessica’s naked backside. Their bodies were both flat on top of the bed. Their bodies were sweaty, and their sexual parts were covered in orgasmic fluids. They breathed heavily and stayed silent for a moment. His flaccid penis was still inside of her ass.
“That…was…unreal…” Jessica groaned from the bottom.
Dave kissed her face. “You were unbelievable.”
“I think you finally got me to change my opinion on anal.”
“So you liked it huh?” he asked, already knowing the answer.
Jessica turned around to lay on her back. Dave’s cock was out of her asshole, flaccid, and dripping with cum and lubrication. He was still on top of her and they were face-to-face.
“Can’t you tell?” she playfully replied.
For the first time, they kissed. Their lips pressed against each others, then again. Their tongues met and they shared a wet, sloppy kiss.
“I’m glad you liked it,” he said in between kisses. “Because there are a few more tricks I’d like to share with you. I’m sure you’ll enjoy them.”
“Do they have anything to do with my ass?”
“What else? Your ass is made for pleasure.”
Jessica smiled, “Now it is, thanks to you.”
The End