Teaching the Cub Ch. 04 - Dinner Guest

A week passed since Tina gave me my oral lesson. That gave my raw shaft more than enough time to heal. I saw her and Sophie on and off over that week. Nothing sexual, just hi's and byes and a few small conversations.

Then one afternoon, about 3:00, Tina called and asked if I could come over and help her with something. I had no more appointments that day, so I said sure and immediately came over. When she answered her door, Tina was wearing nothing but a t shirt and a pair of butt hugging panties.

I immediately felt the need to look away to preserve her modesty. She saw my struggle and laughed.

"Come on, not only have you already seen me fully naked, but you have had your tongue in my pussy." Tina joked.

"I know, but old habits die hard."

Tina glanced down at my crotch and saw a slight bulge forming. "That's not the only hard thing." She joked. Then she turned and quickly mooned me before moving further into her apartment.

I followed her in, closing the door behind me, and asked if her mom was home. My mind was naturally running through a checklist to see if the conditions were right for us to be able to have some more fun. This was actually a new mindset for me. Ever since Tina gave me my first blowjob, the only thing I could think about is cumming with her again.

"Hoping to see her huge tits?" Tina joked.

"No... I.. I mean..."

"I was kidding. She's at work. But I'm going to get you past that awkward shyness you have."

"What do you need help with?" I asked, changing the subject.

"I have to change a light-bulb, but I need someone to hold the stool I'll be standing on."

Tina led me to the kitchen where she bent over and placed her hands on a two foot tall stool. She looked back at me and asked, "Ready?"

Staring at her butt, I couldn't help but think, I'm ready for something alright. I stepped up behind her and held her hips as she began to climb. Once in position I held the stool, which put my face inches from her butt. I watched it wiggle and shimmy as Tina worked.

I was hypnotized by the sexiness of it. Before I realized what I was doing, I kissed it. Tina laughed. "I would say that was the first time someone literally kissed my butt, but I'd be lying. You should try giving it a gentle bite. A lot guys seem to enjoy that."

So I did, and it made me want even more. I felt like I was feeding a beast, but the more I fed it, the hungrier it got. Tina finished and climbed down. I was standing so close that we were spooning standing up. I nuzzled her neck and head with my own, as I wrapped my arms around her.

Tina cooed sexily before turning and putting her hands on my chest. I went in to kiss her, but she pulled her head back. "As much as I would like to see where this goes, I do actually have something else on the agenda for us."

Puzzled by this, I let her lead me back to the living room by the hand. We sat down on the couch facing each other before she continued. "I was thinking about your issue from last week. Where you rubbed yourself raw?"

I blushed in embarrassment. "Yea. I've been a little hesitant to try masturbating again."

"That's what I was afraid of. You don't have a lot of experience with getting yourself off, so I thought I would help you with that."

My eyes brightened as I thought she meant she was going to give me another blow job. As if she could read my mind, she said, "No, I mean, I do want us to continue giving each other oral, and even more. But you need to learn how to take care of yourself when I'm not around."

"You want me to masturbate in front of you?" For some reason that felt more taboo than what we did together.

"Kind of, I want us to masturbate together. That way I can give you a few tips and pointers."

Then I remembered something. "Aren't you worried your mom will walk in on us?"

"No, she won't be home for a while now." And then, changing the topic back, she said, "Have you ever watched porn?"

Despite everything we had done so far together, these questions made me feel such much more naked. "Well, there was the scene I showed you last week."

Tina laughed. "That's not porn, that's just a nude scene in a movie. It was hot, but porn is something different all together. Here, strip down and I'll get you some tissues so that you don't make a mess."

She left the room, and I began to pull my clothes off. This felt so much more dirty stripping in someone else's living room. When Tina came back in, I even covered myself with my hands. Tina laughed at my modesty before handing me the tissues and peeling her shirt off showing my her magnificent tits again. When she pulled off her panties, it took every ounce of strength I had not to grab her. What I would do after I grabbed her I wasn't sure, but I wanted her in my arms.

Tina sat down on the couch and motioned for me to do the same. "Typically, you will need to have some kind of lotion or something. But since I'm here I'll get you wet. Once you get going precum will start to dribble out, that is a great lubrication as well."

With that, Tina sucked my penis into her mouth. After getting it covered in her saliva, she leaned back on her side of the couch, and picked up her phone. "So, what kind of porn do you think you'd be into?" She asked. When I didn't answer, she looked up and noticed my eyes fixed on her tits. She smiled and said, "Got it, big tits."

She pressed a few buttons on her phone and the big flat-screen TV in front of us lit up. Then she began casting a video to the TV. A woman with short pink hair that perfectly framed her face appeared on the screen. She had beautiful blue eyes and soft pink lips. She was wearing lacy pink bra and panties that could barely contain her massive tits. She also had several tattoos all over her body.

I was mesmerized as her and another large breasted woman in her underwear began to make out. Instinctively my hand went to my shaft and started pumping fast.

Tina laughed. "I thought you would like her, she's one of my favorites. Her names Anna Bell Peaks."

I look at Tina as she is speaking and see one hand rubbing circles around her clit, and the other is pinching her left nipple. I'm suddenly torn on whether I want to watch her, or the girls on the screen. I end up looking back and forth between both.

"Remember, don't squeeze too hard and move your hand over your tip periodically to get more lube." I could here her breathing starting to pick up. "One more thing, if you feel yourself getting close, but you don't want to cum yet, slow down or even stop altogether. That's called edging."

That was the last thing she said. The only things I heard from her after that point were moans and whimpers as she worked through her orgasms. Everything was way too hot for me though, and I ended up cumming into the tissue after only a few minutes.

Tina rolled through orgasm after orgasm, and all I could do was watch. Which was perfectly fine with me. About 20 minutes later the video ended and Tina had had roughly 4 orgasms. She now just laid spread eagle on the couch. The problem was, that I was ready to go again. My erection was at full mast. But I didn't want my hand again.

I stared at this gorgeous sweaty naked woman on the couch next to me for several minutes. Then I made a decision. I was losing my virginity today. I crawled over and began kissing her passionately. My kiss seemed to ignite her fire again because she kissed me back just as passionately.

I groped her breasts and pinched her nipples, and she began slowly jerking on my shaft. I pulled back so that I could see where I was aiming, and she helped guide me into her pussy. It felt almost as good as her mouth.

I slowly pumped in and out, in and out, as we resumed kissing. Our sweaty bodies sliding against each other. The heat between us felt like a fire, but I loved it. I felt her hands reach around my back and then slide down to my glutes. She groped my butt as if she were trying to help pull me in deeper.

My kisses moved to her cheek, ear, and then neck. If I could have reached her nipples without pulling out of her, I would have kissed those as well. Her hot heavy breathing right in my hear was making my balls fill even more. My hands moved behind her, one pressing into her upper back, and the other into the small of her back. I pulled her body as tight to mine as I could and we both exploded at the same time. She let out a pleasured scream as I filled her with my cum.

I laid on top of her as we caught our breath and came down from our high. After a minute of cool down, I rolled us over so that she was laying on top of me. I was worried I was crushing her under my weight. She laid her check on my chest and we just enjoyed the moment. I realized that my deflating penis was still inside her, but as long as she didn't care, I didn't either.

After several minutes Tina finally broke the silence. "Was that your first time?"

I gently caressed her smooth back with my fingers. "Yes. I have a feeling that wasn't yours though."

Tina laughed. "No, but I've never had one that intense before. If that was your first time, I can't wait to see what you can do with a little practice."

I felt a warm flush of pride flow through my body. "By the way, you pulled up lesbian porn earlier. Was that just for my benefit?"

"No, remember, I said Anna is my favorite porn star."

"OK. So, your bi-sexual then?"

"I don't know, maybe. I've never been with a woman, not that I'm against the idea. I'll try just about anything once. But, most of my friends watch a decent amount of Lesbian porn as well. I think it's because all of the attention is focused on the woman's pleasure. Kind of like how guys like the idea of being with multiple women at once. More women focused on his pleasure."

"That makes sense." I said

"Did you enjoy the video?"

"Yes, but I enjoyed you more."

Tina looked up at me and said, "That was the right answer. And for that right answer, I'm going to teach you a new position."

My penis twitched to life at the prospect of starting again. Tina kissed me and sat up. "This is called the cowgirl position. It gives the girl all the power." Then she began grinding her hips into mine with me still inside her.

It didn't take long before I was filling her again. My hands surfed over the surface of her stomach before settling on her tits again. Tina looked down to where my hands played. You really like breasts don't you." Before I could answer, she leaned down and shoved a nipple into my mouth. I sucked it in as if I were going to get milk from it. Then I boxed the nipple around with my tongue.

This entire time she was gyrating her hips in circles which drove me wild. Without warning, she sat up and started bouncing up and down and screaming in pleasure. I started thrusting upward to meet her. My hands moved to her hips. Then my left went back and my right came forward.

With my left hand I was groping her left cheek, and with my right I was toying with her clit with my thumb. We were both grunting and moaning and breathing heavy. I came first, but before I finished injecting my sperm into her, she orgasmed as well. This time her entire body spasmed and convulsed before she collapsed back onto my chest.

I wrapped my arms around her and kissed the top of her head. As we lay there, I wondered if what I was feeling was pure afterglow from amazing sex, or if I was really starting to fall for her. I didn't have much time to ponder this though, as Tina tensed at the sound of a car door shutting.

She jumped up and scrambled for her clothes. "Quick get dressed, that's my mom."

I was a little confused, considering her mom had seen me naked and was even the one that helped me get past my fear of masturbation. But I still jumped up and started throwing on my clothes. "With the way you were talking, I figured she would be fine with us having sex."

"Most likely yes, but I still don't want her walking in on me in the process. Also, she wanted to take a slower approach with you. She's afraid you're a little too fragile to progress this quickly."

"Should I just stand here naked as she walks in to prove her otherwise?" I joked, with my limp member still hanging out.

Tina eyed it admiringly and smiled. "Don't tempt me."

We were just sitting back down when the door opened. "Oh, hi Tim. How are you?" Sophie asked.

I was about to answer when I realized the TV was still on. No video was playing, but Anna's tits were exposed in a freeze frame. I tried very hard to not draw attention to it, but failed. Thankfully, the remote was right next to Tina, and she quickly hit the power button just as Sophie was turning to see what I was looking at.

Sophie looked suspicious at the blank screen. "What were you two watching?"

"Game of Thrones." Tina blurted out. "It got to a nude scene. I'd been trying to skip past those so that Tim didn't feel uncomfortable."

Sophie gave me a concerned look. "Tim, are you still having certain issues that we talked about the other day at the gym?"

Feeling really on the spot and embarrassed I said, "I'm better. Better than I was at least."

Sophie smiled affectionately and said, "Good. Do you want to stay for dinner? I'm making spaghetti."

"That sounds amazing, but I wouldn't want to intrude."

"Don't worry about it, we always have way too much. I also have Tina's favorite dessert cherry turnovers with vanilla glaze."

Tina chimed in, "Please stay, it will be so much fun having you for dinner."

The mischievous glint in her eye was so obvious, I was surprised her mom didn't see. "Sure, OK then, that sounds great. Thanks."

Sophie changed into more comfortable clothes, a t-shirt and yoga pants, and we started cooking. Between the two women's sexy outfits, Tina was still in her underwear and t-shirt, I had to struggle to keep up with the conversation.

"Tina," Sophie said, "Why don't you go put some pants on. I think your distracting Tim."

"I'm not showing much more butt than you are in those skin tight yoga pants." Tina answered playfully swatting her mom's butt.

Sophie looked exasperated. "That is not appropriate." But you could tell she wasn't really mad.

"I don't mind." I realized how that sounded after it came out.

Sophie gave me a side eye and said, "I'm sure you don't mind staring at my daughter's butt."

"I mean..." I didn't know what to say.

Sophie laughed and said, "I know what you meant. If you're so OK with underwear at dinner, then why don't you pull off your shorts as well."

I don't know what possessed me, maybe it was the fact that I recently changed to boxer's. Maybe I was growing more confident, or maybe a little of both. But I said, "OK", and pulled off my shorts.

Both girls stared at the minor bulge in my boxers in disbelief. It wasn't a full fledged erection yet, I'm guessing because it was still recovering from all of the activity earlier, but it was still noticeable.

Sophie was the first one to snap out of it. "Well, if we're going to have an underwear dinner party, I might as well jump in as well."

I was the one to look shocked this time, as Sophie peeled off her tight yoga shorts. She was wearing a lacy black thong beneath. I wasn't the only one surprised by her action. Tina looked shocked at her mom's behavior as well.

"I would take my shirt off too, to make it a full fledged underwear dinner party, but I hate wearing my bra when I'm at home. So, there's no way I'm putting one on now." Sophie turned to look at her daughter and said, "And I know your not wearing a bra. I'd be surprised if you still owned one."

Sophie tossed her yoga pants back into her bedroom and continued making dinner. We talked about mundane things work, family, the weather. It was actually just nice hanging out with them. I almost even got used to the clothing situation. We sat the table and started eating.

About half way through, Tina excused herself to the bathroom. A few seconds later, Sophie's phone started ringing in the living room. She excused herself to answer it, and as soon as she left the room, Tina snuck back in and squeezed under the table.

"What are you doing?" I whispered.

"Something I've always wanted to do." Then she pulled down my boxers and started blowing me.

I was instantly hard at the naughtiness of this act. "Your mom's going to catch us."

"No she won't, just act cool. The tablecloth will hide me."

"Act cool? Have you met me? Acting cool isn't something I can do even when I'm not about to cum in my hot girlfriends mouth."

Tina pulled me out of her mouth and looked up at me with a smile on her face. "I'm your girlfriend?"

"I'm sorry, did I make a huge assumption." I felt nervous for a whole other reason now.

"No, I like that idea. I like you, you're sweet and innocent. I've never really had a boyfriend. Most guys just want sex, and then they're gone. No guy has actually wanted to stick around and have a relationship."

"Relationships are all I've ever known. Remember, this afternoon was my first time."

Our conversation was cut short when Sophie walked back into the room and sat down opposite me. "I guess it was a wrong number. I'm surprised Tina's not back yet. I hope she's OK."

I tried desperately to keep a straight face when Tina took me back into her mouth. "I'm sure she's fine, I saw her take her phone with her, so she's probably just playing with it." At that moment, Tina started playing with my balls, and I bit off my last word.

"Probably masturbating to porn more likely. That girl has a bigger sex drive than me, and that's saying something. Before her father passed we humped like bunnies. We did everything. Missionary, doggy, cowgirl, reverse cowgirl, oral, anal, swing, exhibitionism, role-play, threesomes, foursomes, you know, once we had five women in our bed. He felt like a king with a harem that night. Funnily enough, that was the night we conceived Tina."

If I wasn't panting from the secret blowjob already, I would have definitely been after that revelation. "I'm sorry, did I turn you on with that description? Do you want me to give you a quick blow job before Tina gets back out to relieve the pressure?"

Before I could exclaim, "No!", her phone started ringing in the other room again. Seeing her toned tanned butt as she went to answer it, was all I needed. I started cumming hard. I didn't mean to, but I grabbed the back of Tina's head and forced my shaft so far done her throat that her nose was in my pubic hair. She swallowed every drop like she did every time before.

She pulled my boxers up and crawled out. "It's a lucky thing your mom got that call when she did."

Tina brandished her phone and said, "Luck had nothing to do with it."

Tina sat down and continued eating. Sophie walked back in and sat down. Then she started looking at her daughter strangely. "Did you get into the vanilla glaze for the turnover's already?"

"What? No, why do you ask?"

Sophie used her pointer finger to wipe a drop of my cum off Tina's chin. She then stuck it in her mouth and tasted it. "No, that's not vanilla. Oh well."

The conversation moved back to more mundane things after that. We cleared the table and piled the dishes into the sink. Sophie bent over to check on the turnovers in the oven. Her butt got my blood pumping again. Tina, apparently not done with the mischief for the evening, stood beside me and reached into my boxers and gave me a few quick pumps while her mother's back was turned.

She pulled her hand back out at the very last minute. "They smell great, mom."

"Thanks honey." Sophie walked over to the refrigerator and stopped. "Tina, didn't I tell you to take out the trash this morning?"

"Oh, sorry mom, I'll do that now." Tina pulled the trash out, tied it off, and replaced the bag."

"I can take it out." I offered.

"No, Tim, this is her chore. Thank you though."