Teaching the Cub Ch. 05 - Date Pt. 01

I felt guilty the morning after having sex with Tina's Mom Sophie. Especially since earlier that very same night, not only had I lost my virginity to Tina, but we also officially became a couple. I thought a lot about confessing to Tina what had happened with her mom, but I was afraid of how she would take it.

We hadn't even been on our first date yet. That thought distracted me from my guilt. Where should we go on our first date? I thought. I had never entered a relationship like this before. Typically, I had known my girlfriend for a while as a friend before I finally asked her out. That really helped with picking the date location because I already knew what she was into.

I had talked to Tina and her mom, but never actually gotten to any of their interests outside of sex. The only thing I had ever really heard Tina say that she liked, was porn and sex. A crazy idea suddenly came to mind. There was this old porn theater on Broad street. Amazingly it had survived from a time before the internet.

I immediately cast that idea aside though. One, because I thought that might be a little to sleazy, especially for our first date. Two, because I was still trying to get used to the idea of watching porn in the privacy of my own apartment. Let alone a public theater. But, maybe a sexy major release in a normal theater would work.

I looked up what movies were playing on my phone, and was disappointing when I saw most were cartoons and action movies. Nothing against those kinds of movies, I was just hoping to find something risque that Tina would like. Then I found it. At one of the smaller art house theaters there was an NC-17 movie showing.

I had never seen an NC-17 movie before, I hadn't even realized that they still made movies with that rating. It was called, "Rise of the Peaks." When I read the plot summary, I was amazed at my luck. It was a documentary of Tina's favorite porn star, Anna Bell Peaks, rise to popularity. I knew she would love this.

As soon as I got home from work, I showered, changed, and headed next door to see if she wanted to go. I knocked on her door and to say she was excited to see me, was an understatement. She was in her typical home attire, T-shirt and panties. She immediately launched herself at me and kissed me. I kissed back and slid my hands down to her butt, as she pulled me inside.

It took me a second to remember why I was here. I pulled back from the kiss and asked, "Sorry, I wanted to ask you a question."

Tina smiled and said, "I think I already answered your question." Then she pulled off her top, letting loose her amazing breasts. They actually giggled after being freed.

"No," I blushed, "I mean, do you want to go out on a date tonight?"

"Wow, most guys just want me for sex. You actually want to get to know me?"

"Yes. You seem really sweet and funny. And as amazing as sex is with you, I'd actually like to get to know you deeper."

Tina pressed her cheek to my chest and hugged me. "I would love too." Her cheek wasn't the only thing I could feel pressing into me though. Her nipples were so hard that I could fell them pressing into me through my shirt. Which made me hard as well. "Do you mind if we have a quicky before we go though?"

I couldn't turn that down. "Of course."

"Great." Tina turned to walk back to her bedroom, stripping off her panties along the way. "One rule though, there are no clothes aloud in my bedroom."

She disappeared through her doorway and I nearly tripped trying to pull off my clothes on the way to her room. I was completely naked as I crossed the threshold. She was laying on her bed with her legs spread wide. I closed the door and dove tongue first into her pussy.

I had her cumming after only a few minutes. Then I kissed my way up to her breasts, sucking on each one, making sure neither felt neglected. I kissed my way up her chest, neck, cheek, before finally settling on her mouth. With only two days practice, I already felt like I was getting the hang of things as I slid into her smoothly. It's like her pussy was perfectly shaped for my shaft.

I pumped two times before I had a sudden realization. I stayed inside her but pulled my mouth away.

"What's wrong?" She asked.

"Shouldn't I be wearing a condom or something?"

Tina rolled her eyes. "Shut up and screw me, I don't have long before my mom gets home." Her words were rough, but her eyes told me she was kidding. That was all the affirmation I needed. Our love making became frantic, and Tina was screaming as her orgasm began to build.

Everything came to a halt when there was a knock on her bedroom door. We both froze. "Tina?' It was her mom. "I don't mean to interrupt you masturbating..."

"Mom!" Tina yelled in embarrassment.

"Calm down, it's not like we haven't talked about sex before." Tina looked up at me and rolled her eyes. "I just wanted to know if you wanted me to start cooking dinner?"

Something playfully mean rose up in me that I had never experienced before, as I started pumping in and out of her again. Tina was about to answer when the pleasure of my movement made her bite her tongue so that she didn't cry out. She playfully slapped my chest with the back of her fingers.

Tina put her hands to her chest as she tried to focus and even out her breathing. "No, thank you. Tim and I are going out tonight."

"Oh" That's great. Where are you two going?"

Tina rolled her eyes at the continued questioning, and then bit her lip as she accidentally started to let out a moan. "Where are we going?" She whispered to me.

I leaned down, put my lips to her ear and whispered, "Dinner and a movie." The warm breath on her ear pushed her over the edge. I felt the goosebumps materialize on her arms as she spasmed around my member.

Her response to her mom as she was mid orgasm came out strained and a little hoarse. "Dinner and a movie."

"That sounds fun. What are you going to see?"

Tina must have already been building to another orgasm because she finally snapped. "Mom, I'm kind of in the middle of something that requires some focus."

"Alright. Sorry. I'll talk to you latter."

Tina playfully bit my shoulder, and was opening her mouth to scold me, but nothing came out as she was rolling into another orgasm. After another five minutes of slow quiet sex, so that her mom wouldn't hear, Tina came three more times before I finally came inside her again.

We laid on the bed breathing heavily, enjoying the afterglow when I suddenly realized something. "My clothes are out there. How am I supposed to get them and get out without your mom seeing me?"

Tina looked around in thought. "I'll go out first and try to distract her while you grab your clothes and sneak out."

Tina threw on a new t shirt and panties and stepped out. I listened until I heard Tina find her mom in the kitchen. "I'm sorry for snapping at you, I'm just nervous about tonight."

When I heard Sophie's voice I crept out and started hunting for my clothes. "It's OK, I understand. You're father always gave me the same kind of butterflies."

I found my boxers and pulled them on. Thankfully, everything was in a fairly straight line to the front door. I was reaching down for my shirt when I heard the voices coming closer. I had no time to get dressed, and no place to hide. Without thinking I grabbed my clothes and bolted out the door wearing nothing but my boxers.

The problem was that Isabella, our Hispanic maintenance lady, was walking by at that exact moment. Her eyes went wide, but then a pleasant expression washed across her face as her eyes wandered down my body.

"Isabella!" I whispered, "I'm so sorry, please don't tell anyone you saw me like this."

A devious expression came across Isabella's face. "Sure, but you have to do something for me."

"Anything, name it."

"Let me suck your..."

"What?" I asked a little too loud.

Isabella pushed me gently against Sophie and Tina's door. "You heard me." Isabella whispered. "Not many people know this about me, but I have some fetish's that I don't get to act on very often. Like exhibitionism." Isabella began kissing down my chest and abs. "You wouldn't believe how many guys either refuse to perform outdoors, or they can't. The question is, which are you?"

"I can't do this, I have a girlfriend now."

"And how would your girlfriend feel about you screwing her mom?"

"How did you know about that?"

Her tongue was tracing my boxer line now. "I didn't for sure, until now. I mean I saw you two in the fitness center from the security camera's." Isabella began unbuttoning her shirt to reveal her beautifully tanned orange sized breasts. "Boy, did I squirt from that. I just wish I could have seen what you two did in the bathroom, or in your apartment last night."

Isabella's descriptors made my boxers start to tent up. "Please, I can't do this."

An irritated look came across her face. She held a hand up like she was about to knock on Tina's door. "We could ask her permission first if you want."

"No, fine, just do it then."

"That's a good boy." She said as she pulled my boxers down to my ankles. The sudden cool air on my shaft and balls was a sudden thrill that I had never experienced before. Not to mention the fact that it was 5:00 in the afternoon and people would be getting home from work any time now. We were fully exposed to the parking lot. "One last thing. Don't cum in my mouth. Cum on my face and tits. Part of the thrill of doing this out in the open is walking away covered in cum and watching people try not to ask me about it."

And with that she consumed me. She wasn't as good as Sophie or Tina, but she was good. That combined with the thrill of being out in the open like this meant that I wasn't going to last long. In less than a minute, I was tapping her on the shoulder to let her know that I was about to cum.

She pulled off and jerked me the rest of the way. Up to this point, my ejaculations had all been contained by a mouth, pussy, or at least a tissue. This time I finally got to see how much power was behind it. The answer, a lot.

Five or six thick strings sprayed across her face, and about four or five more landed on her chest and tits. When I finished, She buttoned her shirt back up and took my boxers. "These are mine now. Think of them as a memento."

Then she stood, and the pleasant smile that I typically saw on her face reappeared. "Have a nice day." She was back to her normal self, except for the cum still covering her face and chest. She turned and walked away. I turned and quickly got inside my apartment before anyone else could see me naked.

A couple hours later, I was showered dressed, and standing at Tina's door again. I felt guilty about what happened with Isabella, but I wasn't sure if I should broach the topic. All thoughts of Isabella disappeared when Tina opened her door wearing a short flared black skirt and a flowy v-neck tank top. If her mom hadn't been on the couch behind her, I'm not sure what we would have done.

Tina kissed me, said bye to her mom, and laced her arm through mine as we walked to my car. I opened her door for her, and she stepped in, not worrying about the shortness of her skirt. By this point, I was guessing she was intentionally playing with me. The brief snapshot I saw was a simple pair of black lacy panties.

"My word, what a gentlemen." Tina feigned a southern belle accent. Oddly, that nearly got me just as aroused as the panties.

"I got in and started up the car. "I have to warn you, I've been having some issues with my car lately."

"Oh, yea, what's wrong with it?"

"I'm not sure, I don't know cars that well. But, when I get above forty, the entire car starts to vibrate like it's running over a rumble strip."

"Vibrate, you say?" Tina asked with a mischievous grin on her face.

"Yea, and the faster I go, the more it vibrates. I've been trying to avoid the interstate because of that."

Tina seemed to think about that for a second. As if unrelated she asked, "Do you mind if we go to Basil Italiano on South Main for dinner?"

I pictured how to get there in my mind. "Are you sure? That's all the way on the south side of the city. If we don't take the interstate, then we'll be driving for nearly an hour."

"By all means take the interstate then. I don't mind a little vibration."

"Alright, but don't say I didn't warn you." I was still a bit on the clueless side at this point.

So we started driving, and sure enough, as soon as we pulled out of our apartment complex, the car started vibrating. On our way to the interstate we started talking about small things, like our favorite movies. We actually had a lot in common as far as movies go. Although, she did seem to zone out periodically. She even closed her eyes at the moment.

I didn't understand what was going on at first. I was actually starting to worry that she wasn't that interested in the conversation. Shortly after we turned onto the interstate, I finally realized her motives. The faster I went, the stronger the vibration got, and the shallower Tina's breath got. Then she started moaning. I can be thick sometimes, but not that thick.

All conversation ceased, and I just watched her climax out of the corner of my eye. As she came down from the first orgasm, I started pushing harder on the speed limit. In essence, turning up the vibrations. She slid right into the next building orgasm. Instead of taking the exit for the restaurant, I followed the loop of our highway.

Every time Tina climaxed, I increased my speed by ten miles per hour. Each orgasm was louder and more intense than the previous one. She was pinching her nipples through her shirt and I could smell her wet panties. Right about the time she had her fifth orgasm, I saw blue lights behind me.

"Shoot!" I started to pull over. I had been inching around 100 miles per hour. I'd be lucky if I didn't go to jail.

"Let me do the talking." Tina said.

The officer stepped up and I rolled the window down. "Licence and registration, please?"

As I was reaching for my id, Tina spoke up. "I'm sorry officer. Tim here knows that speed turns me on, and we got a little carried away. See how wet I am?"

Tina pivoted her body so that we could both see her drenched panties. The officer froze and was speechless. "If you want, you can have my soaked underwear for evidence." Tina pulled her seat belt off and raised her hips. She hiked her skirt up and slid the wet panties off showing us her beautiful shaved pussy. The officer was so stunned, that she simply took them.

I was even more stunned by the fact that this was working on a female officer. She started to bring them to her nose, but then realized we were watching her, and she quickly tucked them away in her pocket. "I might be able to let you go with a warning this time... Sir, is that a concealed weapon?"

Tina laughed, "No, that's his erection, do you want to see it?" Tina flashed the officer a conspiratorial look. "I'm sure Tim would consent to a strip search."

I gave Tina a stern look asking her what she was doing. But then the officer surprised me and said, "I think I may need to. Sir, please step out of the car."

I was terrified, but I was not about to disobey a cop. So, I stepped out and we walked back to the curb side of her car. She began going through the whole script asking if I had any kind of contraband on me. I answered "No," and she began stripping me right their on the side of the highway.

I wanted to protest, but I couldn't speak. Finally, when I was down to my underwear, the officer got to her knees and pulled my boxers down. My erection nearly slapped her in the face. She smiled and looked at it admiringly, before sucking it into her mouth.

"Ma'am. I'm sorry I was speeding, but that's my girlfriend in the car, I can't cheat on her."

The officer pulled back and looked up at me. "You and your girlfriend got me all hot and bothered. So, either you're going to give me an orgasm, she is, or you're both going to jail."

Then I heard Tina's voice call back from the car. "Let him go down on you, he's really good at that."

The officer smiled at that bit of news. "That sounds like a good idea actually." She stood, unbuckled her pants, and let them slide down. Her panties were the normal everyday kind, but I didn't have much time to see them before they were off as well. She placed her hands on my shoulders and pushed me to my knees. I hesitated, but she wasn't having any of that. she shoved my face hard into her lips.

I was afraid to resist, so I started licking for all that I was worth. I toyed with her clit and used every trick I had been taught. She started grinding into my face. She was moaning and her legs appeared to be getting wobbly. "Stick your finger in my butt"

I pulled away in disgust. "What?"

"Just do it!" She snapped as she shoved my face back into her pussy.

I reached around and groped her glutes. Despite the fact that her butt did feel amazing, I still didn't want my finger in it. Irritated with my lack of compliance, the officer took my right finger and shoved it in herself. She came instantly.

I sat there and felt dirty, I felt like had betrayed Tina again. "Can I go now?"

"No, that was just to get me warmed up." She said as she unbuttoned her shirt and stripped it off. She then pulled off her sports bra and made me suck on her nipples. I can't say that I didn't enjoy that, but they still weren't Tina's or Sophie's.

After a minute of that she bent over the hood of her squad car and beckoned me forward. "Make me cum one more time and you can go." I looked at Tina who was watching everything intently. Well, if she was fine with it, then I might as well enjoy it. I thought.

I stepped forward and taped her clit with my tip. That sent a shiver down her spine. I lined up, and inched in slowly. Once I was fully in, I pulled back out just as slow. "I'm not the kind of person who likes teasing said the officer. I want it hard and rough."

If that's how she wants it I thought. I grabbed a hold of her hips, and slammed home hard. She let out a pleasured scream as I pumped roughly in and out of her. I was so involved with what I was doing, that I didn't notice Tina step up beside me until she started kissing me.

Tina smiled and said, "Best date ever."

Then she did something that worried me, she held up the officers night stick. "What are you going to do with that?" I asked.

"You'll see." Then she bent down, spread the officers butt cheeks and began licking her hole.

Surprisingly, the officer seemed to like it. "Oooooohhhh, Yeeeeeesssss!" She moaned. "Lick it, lick it, lick it."

But then she stopped licking and pulled away. She placed the tip of the nightstick against her hole, and that was when I realized what she was doing. "Stop," I whispered, "Do you want to get us arrested?"

She ignored me though, and slid it in. She buried it four inches deep. The officer was instantly screaming and convulsing in pleasure. I felt her squirting around my shaft, and that was getting me close. I reached around and took her left breast in my left hand, and reached under Tina's shirt and played with her right nipple. That was all I needed, my balls contracted and filled the officer with my seed until it started spilling out of her pussy.

I stumbled backward, tired from the exertion, and Tina cleaned me up with her mouth. The officer continued to lay there, the baton sticking out of her butt. "That..." She said between gasps, "Was amazing."

The officer let us go, but gave us her card in case we wanted to speed again, or doing something even more fun.

As we drove off, I said, "That was really risky what we did."

"No, that was kind of risky what I did. By the time it got to your part, she was ordering you to obey."

"How did you know she was bi?"

"I didn't, and honestly, I'm not really sure if she was. But it's like what I said about lesbian porn. Women are super empathetic to other women's orgasms. I got her to think about the kind of orgasm she could have. She kind of took it from there."