Teaching the Cub Ch. 05 - Date Pt. 01

Something else was bothering me about this whole situation. It also reminded me of what happened with Isabella and Sophie. "You encouraged me to have sex with the cop." I waited for a response, but Tina said nothing. "Isn't that being unfaithful to our relationship?"

Tina's eyes went wide when she realized my problem. "I see where you're confused. We have different perspectives on sex. You're very traditional with ideas of monogamy. I'm not. I see sex as a fun activity to do with people. Think about it this way, having sex with someone to me, is like going to see a movie with a friend. You are both going to enjoy something together."

"So, you might have sex with other people while we are dating?"

"Yes, but you are welcome to do the same thing. Is that going to be a problem?"

I felt a weird contradiction inside. There was a part of me that clung to the values I grew up with, but there was another part of me that was really excited by the kind of freedom Tina was introducing me to. "I don't think so. I mean, it feels weird, but this idea sounds really exciting to me. I think I just need time to get used to this."

"Great! Because I was hoping we could have a threesome at some point." I nearly ran off the road when she said that. Once I regained control of the vehicle Tina began laughing wildly at my reaction.

Conversation moved to tamer topics for the rest of the car ride. When we pulled up to the restaurant, I came around and opened her door for her. This time what she flashed me was much more scandalous than panties.

Tina asked for a booth in a dark corner. I was finally starting to notice when Tina had naughty ideas on her mind. Our waitress didn't help things, depending on your perspective. She was a middle aged brunette with breasts that rivaled Sophie's. She also liked to show them off with her low cut red t-shirt that showed miles of cleavage.

While I tried desperately to keep my eyes up, Tina's first words were, "Nice Tits." I wasn't sure who was more embarrassed, me or Carol, the waitress.

"Umm. Thank you. I guess. Can I get you something to drink?"

"I'll have a glass of wine, and my boyfriend would like milk straight from the tap." Tina joked as she pointed at the waitresses tits.

Carol folded her arms over her chest and asked, "Ma'am, would you stop talking about my breasts, please? You're making me feel uncomfortable."

"Oh. I'm sorry, I tend to always speak my mind, and your breasts really are quiet lovely."

"Thanks, but they tend to just embarrass me. They are really hard to cover and control."

"Why would you want to cover them? If I had breasts like yours, I'd be showing them off everywhere. Heck, I tend to show mine off anyways."

Carol wasn't sure what to say to that. "Sir, a drink?"

"Water, please, thanks." the waitress nodded and walked away.

"You're just all kinds of horny tonight aren't you?" I asked Tina.

"I'm always this horny. You just haven't seen me in public before."

I don't know why, but I felt this was a good time to broach the topic of what happened with Isabella. If what she said in the car was true, then she wouldn't have an issue with what happened.

"Remember how you told me that you believed in being sexually free?"

Tina smiled. "You mean the conversation we had not 10 minutes ago in the car."

I smiled at my awkward start, and continued. "Well, there was something that I wanted to tell you about. I was feeling guilty about it." The waitress interrupted my confession with our drink orders. We placed our food orders and she left.

Tina cuddled up next to me in the booth and wrapped her arms around my bicep. "You were saying?"

"Right." Then I proceeded to explain what happened with Isabella that afternoon. But she kept interrupting me asking for more details. That was when I noticed her smooth thighs were clenched together and she was squirming. She was getting aroused by my story.

I was sure she wasn't going to get angry now, so I played up my shy nervous virgin role and Isabella's vixen nature in the story. She was eating it up as she stared glassily up into my eyes. That was when I decided to push more into her world.

As I continued to trump up the story, I slid my hand down to her knee. She glanced down at my hand and smiled. I slowly slid my hand up between her legs before finally reaching her clit. Her legs parted, welcoming it with open thighs.

I toyed with her clit and she moaned quietly. Tina then began to drop tender kisses on my neck, which made it harder for me to focus on the story. Then I curled my middle finger inside her and she gasped, right before attacking my mouth.

Story time was over. From what anyone else could see in the dim light, we were simply making out. Under the table though, my hand was getting soaked. Suddenly, I felt her body tense up and about a cup of squirt drenched my hand.

Once Tina caught her breathe, we realized our food had arrived. "I think I should go to the bathroom and clean up." She said.

Tina stood and walked to the bathroom. I saw a dark stain on the back of her skirt, which got me even more turned on. A few seconds later, I realized that I hadn't washed my hands yet. Not that I minded Tina's juices, but I always washed my hands before eating.

I got up and turned down the same back hall that Tina went down. I ducked into the men's room and washed my hands. As I stepped out, I nearly ran into Tina. I smiled, took her hand, and went to lead us back to the table, but she pulled me to a stop.

I looked back confused. "What's wrong?"

"Carol is out back, and shes upset."

"What happened?"

"I'm not sure, she won't talk to me. I think I might have made her too uncomfortable with my talk about her tits. Could you go and check on her?"

"But, I don't even know her."

"I know. But she looks really sad and lonely. I intimately know how that feels, and I can't stand to see others in that state."

Despite how uncomfortable it made me to talk to someone I didn't know about their problems. I did it for Tina. She went back to our table, and I stepped out the back door into an alley way.

Carol was leaning against a wall crying. She looked over and saw me. "Great, first your girlfriend, and now you. Can't a girl cry in peace."

"I'm sorry, Tina was really worried about you and she asked me to check on you because you wouldn't talk to her."

"Yea, right. Like that slut cares about anyone but herself." Before I could come to Tina's defense, Carol calmed down and apologized. "I'm sorry. I don't know anything about her. I'm sure she's really nice."

"She is actually. She sent me out here to talk to you because she's know's what it's like to feel lonely. Her dad died when she was young, and so many of the men she has dated simply wanted her for her body."

"And what about you? Are you so different from all of those other guys. I'm not stupid, I know where your finger was."

I felt embarrassed that she knew. "What you don't understand, is that she has helped me overcome so many of my sexual hangups. I was a virgin up until yesterday. Yes, she is very free with her sexuality, but that is what I needed. She actually cares about everyone she meets. That's the only reason I'm out here. I want to be as open and loving as she is."

I waited a long moment for her to speak next. "My boyfriend just broke up with me tonight. Seeing you two together made me miss him." She broke down into sobs, and my natural instinct was to hold her and let her cry into my chest. She wrapped her arms around my torso.

Several minutes later, she calmed down. "Truth be told," she looked up into my eyes, "you two made me super horny, and I'm in no state to even try to pick up a guy right now."

I gently brushed Carols hair away from her face. That's when I realized why Tina sent me out here. I leaned in and kissed Carol on the lips. She kissed back at first, but then quickly pulled away.

"What are you doing? You're girlfriends inside."

"I think this is why she sent me out here. She sensed you had a need that she couldn't fill. I'm sure if she believed that you had the slightest inkling towards women, she would have offered herself to you."

Carol's eyes searched mine for the slightest bit of deception, and found none. "You're sure she would be OK with this?"

"Believe it our not, she told me just tonight that she doesn't believe in monogamy."

"And how does that make you feel?"

"Awkward, at first, but then I realized the freedom there is in that. We can have sex with anyone we want. No baggage. Just pleasure."

Three heartbeats passed before Carol started kissing me again. I kissed back and my hands traced up and down her sides, before forcing her back against the brick wall. My hands slide down to her legs and pushed her black skirt up. Her hands moved between us and unzipped my pants before fishing my penis out.

I pulled her panties to the side and entered her. Never once did we break our kiss. I pumped in and out of her, pinning her to the wall. She wrapped her legs around me. We started having trouble breathing so we broke the kiss.

My hands took the bottom him of her shirt and lifted it above her breasts. She was wearing a no frills white bra. I pulled the cups down and began sucking on her nipples. Her labored breath pushed me harder and faster. Our pace increased, and our grunts and moans grew faster and louder.

My hands replaced my mouth on her nipples, and I nuzzled her face with my own. Our orgasms seemed to build at the same pace. Right as I was about to pull out, so that I didn't cum inside of her, she clenched her legs to pull me in deeper. We climaxed at the same time.

I found it hard to worry about the possibility of getting her pregnant in that moment. We stood there and held each other until I went limp and fell out of her. "Do you feel better now?" I asked.

She laughed and said, "You're girlfriends a very lucky woman. Thank you."

"I'd be lying if I said I didn't enjoy it myself." We both laughed and made ourselves presentable again. "By the way, Tina was right. Your breasts are gorgeous."

Carol smiled, and then seemed to ponder something for a second. Finally, she pulled her shirt off, undid her bra and handed it to me, before replacing her shirt. "A memento."

I went back inside and told Tina everything. She didn't believe me at first, but then I showed her the bra. About that time, Carol walked up. "Is this really your's?"

In answer, Carol flashed us. Tina burst out laughing and Carol had to pull her shirt back down quickly before someone saw. "You were right. I shouldn't be ashamed of my body. And thank you for lending him out to me. I really needed that. My ex was pathetic in the bedroom, so I hadn't had a good orgasm in a while."

We chatted for a while longer, but needed to get going if we were going to catch the movie. So, we said our goodbyes, paid, and left.

To be continued.