Teaching the Cub Ch. 01 - Introduction

Story Info
A painfully shy virgin meets an experienced cougar.
1.6k words
4.1
42k
34

Part 1 of the 6 part series

Updated 06/09/2023
Created 01/03/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
sthsth
sthsth
584 Followers

I'm trying a couple things differently with this one. One, shorter chapters. Two, deeper stories and more developed characters. As always, let me know what you think. Except for grammatical errors. I do care about those, but once the story is up, there is nothing I can do about it.

*****

Tim

As I pulled into the parking space outside of my apartment, I saw a moving truck being unloaded. Obviously I was getting new neighbors, but I couldn't see who yet. Regardless, it probably wouldn't make a difference. The people in my apartment complex typically kept to themselves.

There was the polite "Hi" here and there, but in general this was a fairly introverted neighborhood. At least, as an introvert myself, that was my perspective. So, I kept my head down and walked to my apartment on the first floor. I hoped I could get inside without making eye contact with anyone.

Introvert might not be the right word for me, phobically shy might be more accurate. I was 20 and had never had a girlfriend. Which also meant that I was a virgin. Which in today's age meant that I might as well of been an alien. At my last physical the doctor asked how sexually active I was. When I gave him the answer he thought I was lying.

I wasn't in luck today though, because the door next to mine was wide open and I could see furniture being move around inside. It was an impossibility that I wouldn't be seen entering my apartment. I almost turned around and got back into my car. I thought about driving around until later that night.

I refused to let myself be that cowardly though. I took a deep breath, got my key ready, and marched fixedly to my door. I stuck my key into the lock, turned and was in. I closed the door behind me, thankful that I had avoided an awkward social encounter.

Knock knock knock! I knew I couldn't of gotten away that easily.

I took a deep breath and opened the door. I should have looked through the peephole first. A swat team busting through the door would have surprised me less. I saw a 30ish gorgeous blonde woman standing there. Her eyes were the brightest blue. She had breasts the size of small watermelons, and was wearing a tank top that liked to show them off. She was also wearing a pair of short black running shorts.

Her long sexy athletics legs stretched down into a pair of tennis shoes. She had to be at least 5'7 to 5'9. If all that wasn't enough to cause a reaction in my pants, then her bright smile was. I felt like my neck was about to snap as I tried to maintain eye contact and not look at her body. I was raised to be a gentleman, and not gawk at women's bodies.

"Hi! I'm Sophie." The woman stretched out her hand.

"Uh, um, Tim, I'm Tim." I shook her hand.

"I just wanted to introduce myself, My daughter and I are moving in next door."

"Hi, welcome to the neighborhood." Was all I could think to say.

There was an awkward pause, and then she continued. "So, Tim, what do you do for a living?"

"I'm a personal trainer."

"Oh, that's great. Maybe you could give me a session sometime. I have a little extra weight that I want to lose."

I gawked at her comment, I couldn't see a flaw on her. She wasn't model thin, but that's not healthy. She was, as far as I could tell, a perfect healthy weight.

"Where could you possibly want to lose? Your body is amazing." The words slipped out before I could stop them. "I...I'm sorry."

"For paying me a compliment?" Sophie laughed. "Thank you. I try very hard to keep lean and healthy. But at my age it's getting harder and harder. It's mainly a little excess fat around my butt." She turned and stuck out her butt a little.

The shorts were so tight that they creased along her crack. For added effect, she bounced a couple times. Her but giggled a little, and I nearly had an accident. She turned back around and glanced down, noticing my erection straining at my shorts.

She blushed and tried to restrain a smirk. She said nothing about it as I crossed my hands in front of me to try to hide it. "Yea, sure, just let me know when would be a good time. I'm free tomorrow."

"OK, let's say 9:00 at the apartments fitness center?"

"Sound's good, see you then." I said as I attempted to hurriedly shut the door.

Once the door was closed, I immediately went and took an uncomfortably cold shower. The receding sperm made my balls ache something fierce. I wasn't sure how I was going to train her tomorrow if my body had this kind of reaction to her.

My typical clients were overweight middle aged men that were coming to see me to get their high blood pressure under control. I had never trained someone as painfully attractive as Sophie before.

Sophie

"You should have seen him." Sophie told her nineteen year old daughter Tina. "He was trying so desperately not to stare at my tits. I couldn't help but tease him a little. So I turned and gave him a quick little but shake."

"Mom! Shame on you. You shouldn't act so slutty."

Sophie stared at her daughter incredulously. "Says the person who has to walk around the house in nothing but a tight t-shirt and sexy butt hugging panties." Sophie playfully smacked her daughters thin tight butt. It was sticking out as she leaned over the counter top into the kitchen.

That made Tina straighten up. "Hey, I just like to be comfortable. If I had my own place I'd be walking around butt naked."

"I have a feeling that you would do that if you had any other roommate than your mother."

"Mom, you're the slutty one remember? You're the one teasing our neighbor the first time you met him."

"I'm the slutty one? I'm not the one that had a threesome affair with a married congressmen."

"You keep bringing that up? Why won't you let the past die?"

"The past? It was a month ago. And it was the reason we had to move. Let's not forget that he was my boss."

That shamed Tina and she produced a pouty face. Sophie walked over and hugged her daughter's head to her chest. "I'm sorry, I've just been really stressed out with the move and finding a new job and everything."

Tina wrapped her arms around her mom's waist and said, "No, I'm sorry. That was a stupid and selfish thing for me to do."

"I guess you are just too much like me." Sophie said. I haven't exactly been the best model of chastity over the years."

"Yea, especially since I can typically hear you watching porn every other night though my bedroom wall."

Feeling defensive at her daughter's knowledge of her porn habits Sophie said, "Hey, I've heard your orgasmic cries through my wall more than a few times as well."

"I wasn't judging, I just meant that I understand how lonely you feel since dad died. Whenever I think about him in bed at night I masturbate."

Sophie pushed her daughter to arms length and gave her a weird look. It took Tina only a second to realize what she said. "No, I didn't mean it like that. I just meant that when I start to feel sad, I masturbate to take make myself feel better."

Sophie wanted to laugh, but she simply cried and held her daughter again. "I understand. I do the same thing."

The two girls finished dinner and went to their respective bedrooms. Sophie was still thinking about her late husband and couldn't get to sleep because of her pain. So, she picked up her phone and found some "reading material", as she called it around Tina. In no time she was rubbing her clit and twisting her nipples while imagining what she had read on literotica.

She couldn't help the loud moans of ecstasy that escaped her lips as she came. As she laid there catching her breath and coming down from her high, she heard her daughters moans as well. The knowledge of what that meant made Sophie roll over on her side and cry.

Tim

The pleasured moans I heard through my wall were unbearable. That was all it took to give me another raging hard on. Not again, I cried as I took my second cold shower for the day. My balls felt like they had been used as a speed bag.

The cold shower only had a short term effect though. In the night I dreamt I was sucking on Sophie's nipples. I kissed my way up her chest until I was kissing her mouth. My hands came up and began playing with her nipples. That was when I woke up ejaculating in my bed.

"Shoot! Not again" I said as my last few spasms made a mess that I would have to clean up.

I couldn't help crying as I cleaned first myself, and then my bed. I was lonely. Yes, I wanted sex, but I also just wanted someone that cared about me. Someone that I could hold or could hold me. But my stupid mind always got in my way. I was too shy to even ask a girl out on a date.

To be continued.

sthsth
sthsth
584 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
AnonymousAnonymousover 4 years ago
I was disappointed it was MF as opposed to FF

If , for example, Tim had instead been a painfully shy virgin named Timothea, it would have made a world of difference.

luedonluedonabout 5 years ago
Thanks Mr G.Imagination

Your comment led me to read this interesting story.

I agree with others about change of narrator. I find that it rarely works well with the changes in short segments. In this story I found it even stranger since the Tim segments were told first person and the Sophie segments were told third person. My opinion is that with stories like this, it would be preferable to tell the whole story third person.

Apart from that, I liked it. It was readable and well written. Tim was a well-developed character, although the idea of a painfully shy person working as a personal trainer seems a little unlikely. However, it sets the scene for the 'cougar and cub' scenario I assume is to follow. (I have developed a liking for older lady with younger man stories.)

I look forward to the next chapter.

Lue

GrrrreatImaginationGrrrreatImaginationabout 5 years ago
A lovely start.

Sorry this is so long.

Good story-telling - the scenes unfold smoothly and coherently.

You've given us a peek into the lives of Tim and of Sophie & Tina. They have really different world-views, and are near opposites in some ways, while I suspect they all share a desire for some improvement of their relationship and sex-partner situations. I'm looking forward to hearing more about how Tim finds his way at least part-way out of his shy shell. And Sophie and Tina offer such potential...motivation in that regard. Mmmm.

You've already identified some proofreading issues, though they were hardly worth mentioning, imo.

You did a really good job in the introduction scene of showing how people try to regulate their behavior in social interactions, even when everyone involved knows there is more going on in the undercurrents. He knew that she knew and she knew he knew, but they kept the conversation on the up-and-up. That is good story-telling - funny, sexy tension that keeps me coming (I mean, reading).

I liked that you identified when you were switching perspectives, and I think you did a good job of keeping the thread of the story going, even as you revealed more about each character.

Speaking of perspective, I can't remember the name, but one of the Lit authors has a quick blurb at the start of most stories, in which the author says they do one read through before posting. The author furthermore owns that there are probably spelling or grammar glitches that remain, and goes on to make the observation that the readers are getting free smut to read, and if they are so picky, perhaps they should be paying for the privilege. I think the author suggests that feedback about such things will be ignored or deleted.

Once I read that, my perspective matured, and I got a lot more deliberately constructive about the feedback I give. I really appreciate the authors, and try to convey that. They've got, and you've got the imagination, the talent & skills to tell the story, and the guts to put your creations out there for the readers. That's a courageous thing to do. Thank you! for sharing your creativity.

Please keep writing.

sthsthsthsthover 5 years agoAuthor
In response to "Enormous" comment.

I agree that spelling, grammar, and vocabulary are important, but it is very hard to proof read your own work. You tend to see what you mean instead of what you actually typed. And, as far as I can tell, I can't make changes once it is posted. I do attempt to improve every time, but I don't appreciate you acting like it is that easy to be an author, especially when I don't have an editor. And I understand if you don't like this chapter, but very few stories are built with one chapter, and I'm trying something different from all of my other stories. Most of the rest I've felt like I was rushing them, so I'm trying to give this story a little more room to breath. Finally, what feedback? All you said was that you hated my story and that changing perspectives is hard to do. Try constructive criticism. What did you not like? What did I do wrong with changing perspectives? What could I do better? I'm all for constructive criticism, but all you told me was that my story was crap. I can't do anything with that. There are no actionable items in that.

AnonymousAnonymousover 5 years ago
Enormous

Another example of why changing perspectives are rarely a good idea.

Spelling, vocabulary, grammar. It's all important. You can't do anything once it's posted? So improve next time! You can't do anything about the shit story either, but hopefully our feedback will help on the next attempt.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

After School Special Todd's mistake gets surprising results from Miss Ross.in Mature
Neighborhood Milf Life long dream fulfilled when he has her.in Mature
Best Friend's MILF Robert gets some special thanks from his friend's mother.in Erotic Couplings
Ms. Jackson Ch. 01 Boy is torn between his longtime girlfriend and her sexy mom.in Mature
My Best Friend's Hot Mom Young stud bangs MILF in all 3 holes during hot summer day. in Mature
More Stories