Teaching the Cub Ch. 02

The first chapter was slow but I felt the need to set up the characters. This one has much more sexual content, and will be setting up the idea for the series. Hope you enjoy it, and let me know what you think.

*****

Tim

There was a knock on my door at 8:45 a.m. It wasn't too hard to guess who it was. I opened the door and Sophie was standing there in an even skimpier outfit than the day before. She was wearing a sports bra that acted more like a push up. Her belly was toned and beautiful. She also wore a skimpy pair of tight white workout shorts.

It was starting to become apparent that she didn't believe in underwear. Not only could I see the imprints of her nipples poking through, but she also had a very prevalent camel toe. Thankfully, I was wearing briefs today to try to keep myself under control.

"Are you ready to go?" She asked cheerily.

"Yea." I said and stepped out of my door, closing it behind me.

Sophie immediately turned and started walking towards the fitness center. That gave me a spectacular view of her butt in what had to be vacuum sealed shorts. They hugged her beautiful orbs so tightly, that I wondered how she got into them.

I quickly caught up to her and started asking her questions about her health and fitness. I hoped the distraction would make my underwear a little less tight.

"Do you have any preexisting conditions I should know about?"

"Yea, I struggle with a little bit of back pain. My doctor said it's because of my huge tits." Sophie pulled the top of her bra down a little too show even more cleavage. "He recommended I get a reduction or strengthen up my back. And I paid to much money for these babies to get rid of them."

Feeling awkward and a little pained from my constriction, I just nodded and looked ahead. "Well, it's good to strengthen your back anyways."

We made it to the small fitness center and had the room to ourselves. After I took her through some warm ups, including jumping jacks that made me repeat the same number six times, I brought her over to the dumbbells.

"OK, so you said that you wanted to strengthen your back and tone your glutes. The best way to do that is with squats. I prefer goblet squats because they are great for beginners. I think it will also especially help you, because you are having issues with... um... extra weight... up front."

Sophie laughed. "I've never heard my boobs called that before."

I smiled nervously before turning to grab a dumbbell. "Ok, let's start with 20 pounds. That's a nice and easy weight."

"Hey, that's how much my breasts weigh."

I was starting to wonder if she was purposefully trying to tease me. I turned to face the mirrored wall, held the weight between my hands, and did five squats to show her how it was done. I was giving her tips about form and what muscles she should feel working.

Then I handed her the weight and stepped to her side to watch her do the squat. I corrected a few minor deviations in her form, but for the most part she picked it up quickly.

On the next set, I walked around behind her to check her form from there. She went down, the fabric of her white shorts stretched, and they went transparent. I was suddenly looking at her amazing butt through the sheer fabric. My penis swelled so much that I almost thought I heard a few threads ripping.

I would like to say that I immediately told her about her issue, but I didn't. I meant to, but I was transfixed by it until she got to rep eight. Then I stepped forward and motioned for her to stop.

I leaned in and with a lowered voice I said, "I'm sorry, I think you should know that your shorts are rather sheer when you squat."

She smiled, looked me in the eyes, leaned in even closer, and asked, "Did you like what you saw?"

I was dumbfounded. I could think of nothing to say, so my mouth just opened and closed several times. Finally she gently tapped my cheek and said, "You're adorable. Thanks, but I'm not the modest type. Go ahead and enjoy the show."

Again, I had nothing to say. And even though I knew I would probably end up with blue balls again, I sat down on a workout bench and watched her. Her butt appeared and disappeared like the sexiest magic trick ever.

I'm not sure how much time passed, but I was woken out of my lustful stupor when she asked a question.

"I'm sorry what?" I had to ask.

"How many of these am I supposed to do. I'm really starting to get tired."

"How many have you done?"

"150."

I stood up immediately. "I'm so sorry, I got... distracted."

"I could tell." she smirked at me and then reracked the weight. When she turned to face me, a pained grimace crossed her face and she cried out in pain. Then she collapsed into my arms.

I wrapped my arms around her to catch her and lower her gently to the ground. "What's wrong?" I asked.

"Cramp!" Was all she could say while motioning to the back of her body.

I laid her on her stomach and began massaging her hamstring. "Higher!" She said. And I moved higher up on her hamstring. "Higher!" She cried more insistently. So I started massaging her lower back.

She finally growled in irritation and placed my hands on her left glute. I froze. "Don't stop!" She screamed. So I started massaging her left butt cheek.

She started moaning from the relief. I wanted to start moaning for other reasons, but I managed to hold it back.

"You're really good at this. I bet your girlfriend loves when you do this to her."

"Actually, I've never had a girlfriend." I admitted shamefully.

"Really? Gorgeous sweet guy like you? Not to mention those abs I felt when you caught me."

I blushed even more at the compliment, than what I was groping. "Thanks. I'm just really shy."

"You shouldn't be. If you just showed the tiniest bit of initiative the girls would be falling all over you."

"I just don't know what to say. What did your husband say to you?"

A brief darkness crossed over her face. "My late husband had a perverted sense of humor that I loved. He took one look at my tits and asked if he could have some milk in his coffee. I wouldn't recommend that line for you though. It takes a special kind of girl to fall for a joke like that."

"If you don't mind me asking, how'd he die?"

The darkness returned. "A car accident." Sophie then looked back at me and said, "I think I need you to go deeper." And then she slid her shorts down right below her cheeks. "Continue."

I just stared at the magnificent view in front of me. I had never scene a woman's butt in real life before, let alone had I been able to touch it. I poked it with my pointer finger, and that made her laugh.

"I get that you're a virgin, but surely this isn't the first butt you've seen."

I began to massage it again, my eyes transfixed, my breath quick and shallow. "In real life it is." I said.

Suddenly I got a quick glimpse of her butt hole which felt even more taboo than what I had already seen. Without thinking, I straddled her legs and began fondling both cheeks at once.

She moaned and said, "You could have fooled me with how well you handle them." Fishing for a compliment, she asked, "So, how do I stack up to your favorite pornstars?"

That statement caught my attention and I suddenly felt ultra self aware. "I'm sorry, I've got to go." I stood and started to walk to the door.

Sophie quickly pulled her shorts up and stopped me. "Tim, what's wrong? Are you weirded out that I asked you about porn? It's ok, I look at it too." That statement made me swell so much that my briefs became useless in their wrestling match.

"You don't understand. I don't look at porn."

That statement shocked her. "Are you against it morally?"

I shook my head embarrassed by the truth. "No, trust me, I would love too. But it gets me too excited."

Not understanding my point she said, "Yea, that's the point, then you get the release of an orgasm."

"No, you see, I can't masturbate."

"I'm sorry, do you have some kind of condition? Is your penis really sensitive or something?"

Feeling completely humiliated and really not wanting to tell her the ridiculous truth, I turned to leave. "I'm sorry, I can't."

But she grabbed me and forced me to turn and face her. "Tim, I know we just met, but you can trust me. You're not going to embarrass me. I've done the kinds of things that embarrass some pornstars."

I fought an inner battle with myself before saying, "I... I was told something when I was a kid."

Sophie laughed. "A kitten is not killed every time you masturbate."

"No, it's not that. And, I know this isn't true. I know it's ridiculous, but it scared me so deeply that I have an anxiety attack everytime I touch myself. I can barely clean it."

Sophie got a concerned look on her face. "Tim, what did they tell you?"

My eyes started tearing up. I was about to tell her something that I had told no one before. "I was told, by someone I trusted implicitly, that it would fall off if I played with it."

Sophie took me into her arms and held my head to her chest. That sent a weird mixture of comforting and erotic feelings coursing through my body. "Tim, I know you are embarrassed by that, but let me reassure you, that is nothing to be ashamed of. Things that people tell us when we are kids can easily scar us for life. My sister told me that pine cones were snake eggs when we were kids. I still get a little weirded out by them."

I wrapped my hands around her back and we just held each other for a while. "I've got an idea." Sophie said.

She pulled away from me and lead me by the hand to a nearby single person bathroom. I tried to resist joining her, but she wouldn't let me leave. She closed and locked the door behind us.

"Now, take off your shorts."

"What?" The request alarmed me.

She placed her palm gently on my cheek and said, "Trust me on this." When I didn't move, she had another idea. "Here, I'll go first."

And with that, she began wiggling out of her shorts. When her smooth hairless vagina came into view, I had trouble breathing. She kicked her shorts off to the side and took my hand. She led it to her womanhood.

"This is what a pussy feels like." My eyes flashed surprise at the word. I had heard it before, but I always thought it was an impolite name. Noticing my shock, she continued, "It's ok to say that word. Well, in settings like this it is. Come one try it."

Feeling uncomfortable I hemmed and hawed and couldn't do it. She forced my eye contact and pronounced it slowly and deliberately. "PUSSY."

I wet my lips and practiced the shape of the word in my mouth several times before I finally put breath and voice behind it. "P...P...Pussy." The naughtiness of using the word made me flush. But I liked the feeling it gave me. "Pussy." I said more confidently.

Sophie smiled and said, "Good. It feels good doesn't it?"

"Pussy." I repeated again as I rubbed hers with my fingers. I was so enthralled that I didn't notice her undoing my shorts and letting them drop to the floor.

I noticed her eyes get as big as saucers and realized that she was looking at my bulge. My briefs were about ready to rip off from the external force of my erection. I suddenly looked down and felt self conscious.

She took my chin and made me look her in the eyes again. "Tits." She said, and then pulled her sports bra off. My eyes bulged at her massive breasts and the thick erect nipples. "Say it with me now. "Tits."

This one was much easier after my last word. "Tits."

"Good, and as a reward, you can suck on them."

My heart skipped a bit as she lead my head to her massive tits. I stuck out my tongue and flicked her nipple. That made her moan and shudder. Then I sucked it into my mouth. I was moaning almost as much as she was. I used my right hand to play with the other. This was indescribably better than my dream.

After a few moments of this, she pulled away. "OK, we still have a little ways to go."

Sophie next lowered to her knees and slid off my briefs. My eight inch erection smacked her face once it was released from it's prison. She then licked her palm and took me into her hand. I felt a flood of pleasure and anxiety all at once. I wanted to run from the room but also stay there in her hand for all eternity at the same time.

My lust prevailed and I stayed. She added her other hand and started giving me my very first hand job. The more my orgasm built, the more I forgot about that silly lie I was told as a kid. Until suddenly my legs felt weak, and my penis began spitting sperm all over her massive tits.

I had to grab a hold of the handicap railing to keep from falling. When my ejaculation was over, I regained my strength and stood on my own again. That was when I noticed my sperm all over her tits.

"I'm so sorry, let me help you clean that up."

Sophie laughed. "Always the gentleman. Don't worry about it, this is vocabulary lesson number three." She scooped up some of my sperm with her middle finger and said, "This, is cum, in porn they would say you came on my tits."

"I came on your tits." I said contemplatively.

"And something else you should know, some women, myself included, love the taste of it." With that, she licked my cum off her finger. That made my balls start to stir again. I watched her scoop all of my cum off her tits and eat it.

By the time she was done, I was fully hard again. She looked at my shaft and said, "Looks like it's time for your first test."

She sat me down on the toilet and said, "Now, it's your turn to masturbate."

I looked down at my erection, mystified by the pleasure I had been missing out on all these years. Pleasure that I could elicit from my own hand. I gingerly wrapped my right hand around my shaft and began to stroke. Slowly at first.

I looked up and saw Sophie lean back against the wall in front of me. She lifted her left leg and planted her foot on the handicap railing. "This, is one of the ways that women do it, and this little guy is a clit."

I watched her intently as I stroked myself. As her fingers teased her clit faster and faster, I stroked at a matching pace. Her breathing became labored and that sound was the most erotic thing I had ever heard. Then she started moaning, and I didn't last much longer after that.

I ejaculated and my cum mostly landed on the floor beneath her, but some of it landed on her shin and foot. She orgasmed seconds later, and I wanted nothing more than to stick my tongue in her.

Once she caught her breathe, she lowered her leg and said, "Congratulations, you passed your first class."

"Class?"

"Oh yes, I have so much more to teach you."

Sophie

"Mom, I can't believe you did that." Said Tina, sporting a black thong and tshirt tonight.

"Well, someone needed to teach him. I felt sorry for him. Not to mention you should have seen it."

"Was it big?"

Sophie held out her hands to show how big.

Tina smiled dreamily. "Maybe I should go over and introduce myself."

"Not yet."

Surprised by her mother's response, "Yet?"

"Yes, there are a lot of things we need to teach him. But we can't overload him at once."

"We?"

"I was hoping you would help me."

"Eww, gross, mom I'm not having a threesome with you."

Sophie rolled her eyes. "I wasn't suggesting incest. I meant separately we take turns with him. It will be good for him to get experience with different women."

"OK, sounds good, so where do we go from here?"

"Not sure yet, I'm playing this by ear."

To be continued.