tagAnalJessica's Anal Curiosity

Jessica's Anal Curiosity


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."


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.


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:


Thanks for the nice message. How did things go with Amy? What makes the whole anal thing work so easy for you?


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.


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.


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.


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."


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?"

Report Story

byHeyAll© 19 comments/ 126742 views/ 86 favorites

Share the love

Report a Bug

3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: