Teaching Chantelle Ch. 02

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[MF, Toys and Masturbation, Anal]

Tag: Chantelle’s vibrator play turns anal… with a twist

This is Chapter 2 of “Teaching Chantelle.” It picks up right where Chapter 1 left off, so if you’re interested in the story, you should probably read the previous chapter.


Having just helped her come with a vibrator for the first time ever, I lay on the bed next to Chantelle for a bit, relaxing while she was still catching her breath. My shorts were still on, and she was completely naked. After a minute, I reached out and started playing with her breasts again. “Hey,” she said, “hands off!” But she didn’t move my hands away.

“I was just wondering what else I needed to teach you.” I said. “You’ve done a pretty good job so far, but what else do you want to know? Or are you ready to practice again?”

“Thanks, not quite yet,” she said. “I still need to recover.” She looked down, reached out and gently grabbed my package through my shorts. “I was thinking you might need some help yourself, though. You’ve been a very good teacher. But I see the educational process has gotten you a bit excited.”

Looking down, I saw that I actually had a small wet spot that had made it through my shorts.

Oops. “Wow, that doesn’t usually happen.” I said.

“Something about an hour of foreplay while you are still partly dressed?” she grinned at me.

“Maybe.” I remarked. “But remember, this is all about helping you.” I turned mock-serious. “Ms. Jones, as your teacher I want to be sure you have learned everything you want to about your new toys. As a teacher, it’s my responsibility to ensure your education. And as an educated professional, I know how to take care of this other problem along the way. So before turning to that, what else would you like to know about? Remember, there is no question too dumb, or scenario too kinky, to ask about. This is a professional, student-oriented program.”

“Hmm,” she said, “such the dedicated educator.” Her eyes roamed around, taking in the vibrator on the bed between us, the obvious bulge in my shorts, the bottle of lube on the side table, and the other vibrator. When she looked at it, she paused.

“You know, I was wondering a little about the other one. How does it feel?”

I picked it up. “Well, it probably feels like the first one, but it’s a little smaller. Maybe the vibration is a little more concentrated, but you know, well, it’s smaller, so it’s probably just not as filling…”

Chantelle was shaking her head. “That’s not what I meant. What I want to know is, what does it feel like on you? What if I want to use it on a guy? I mean, you were talking about it being, you know, in you? I want to know about that.” She was shooting me little glances as she said this. But as she did, I could see a blush creeping up her face. Even after all this, she didn’t want to come out and say it.

“So, you want to talk about using it anally?”

She took a deep breath, and this time she looked me square in the eye as she said “Yes, I do.”

Maybe I could turn this into something good for me too. “Sounds like another lesson. I’m happy to help. Let me think.” I reached over and picked up the smaller vibrator, and turned it on. Its buzzing filled the air as I turned it over in my hand. “Hmm, well, let me tell you a little more.” I ran it down over my chest, and actually over my hard on inside my shorts, and then I handed it to her. She repeated the motions, running it over my chest and down. She actually teased me by reaching it around and pushing it against my butt. She brought it back around and held it against the front of my shorts while I talked.

“I don’t remember the first time my girlfriend used it on me. The sensations are kind of nice inside, the key is just to use lots of lube. And I’ve never been able to get off just from the vibrator alone. But as part of playing, it’s really good. There just needs to be some warm-up. And go slow. Just like anal sex with you.” I told her a little more about how my girlfriend had given me a blow job while sliding a vibrator into my ass, and about how good it felt.

We lay there together for a minute, Chantelle thinking about it, and looking down at me while she ran the vibrator over my shorts. Then she spoke quietly. “Can you show me?”

Now it was time for my face to turn red. I pretended I had to think about it. “Um, OK. It’s just a different lesson, right?” She nodded. “I think I can. But, I need to get naked.”

“That’s OK, I showed you mine, so now you show me yours.”

“Just like 4 year olds playing doctor?”

She laughed. “Yes, just like that. Here, let me help you off with that.” She reached to my waist with two hands and unbuttoned my shorts. She began to push them down, and I raised my hips to help her slide them off. After all the ups and downs of the past hour, my cock was tangled up in my briefs, and I had to reach down and free it. But in a second, my shorts lay on the floor, and I was lying next to Chantelle, my erection sticking up against my belly.

I put one hand on Chantelle’s hip. Now that we were lying there naked, I was almost casino şirketleri overcome with the urge to just roll her over and climb on. But that wasn’t part of the deal. Chantelle looked down at me, though, and brought her hand to grasp my cock. She slid her hand up the length of my shaft, squeezing, and then she then ran her fingertip over the head of my cock, collecting the pre-cum she had squeezed out of it. She locked eyes with me as she brought her finger to her lips and sucked it into her mouth. “Mm, tastes good too.”

She then sat up, and moved to the edge of the bed. “OK, my turn to ask the questions. Lie down on your back.” I did as asked, and she moved to sit almost like I had, on the edge of the bed, at my waist. “So, Mr. Jackson, you’ve used a vibrator like this one before?” She held up the smaller vibrator.

“Yes, a lot like that.”

“Have you used one like the other one, or is it too big?”

“Well, sometimes, maybe, but the smaller one is a little easier.”

“OK, and is it good when I do this?” She ran it over my nipples.

“Well, it’s OK, but boy nipples just aren’t the same as girl nipples. At least, mine aren’t.”

“Hmm. Well, how about this.” And she moved the vibrator down to my cock, running the vibrating end over the shaft of my cock, then holding it against the head.

“Ah!” I said, jumping a little. “It’s OK, but a little intense just on that spot.”

“Sorry,” she said, running it back up and down my cock, and down over my balls. I just lay there and let her have her way. She watched the vibrator, occasionally glancing at my face. After a minute, she asked “Am I doing it right? This doesn’t seem to be doing much for you.”

“Well, like I said, it’s different. Think about the shape, it’s really meant to be inside something.”

“Yes, I guess you’re right.” She looked at me. “So, like I said, can you show me?”

“Well, I can probably only show you so much, without help, but I can get you started here.” I thought for a second. “I think there are probably 3 positions I’ve done this in. Do you really want to see this?”

“Oh, yea,” said Chantelle quietly.

“OK, this is your lesson. I suppose the first way you could do it is lying on your side.” I rolled over so I was on my left side, with my back to Chantelle. I slid over more on the bed to make room. “Here, lay down behind me, and give me your hand.” She lay down, almost like we were spooning. I reached back over and took her hand holding the vibrator, and guided it down until the vibrator was at the bottom of my ass, just behind my balls. “You need to get the spot and the angle right, but you could then just kind of slide it in.” She pushed up with the vibrator. “Wait, wait, not now! It only works if the vibrator and everything is ready, remember?”

“Sorry.” she said. “You know, holding it like this, I almost feel like I’m fucking you from behind.”

I laughed. “Well, what do you think you’re doing? That’s exactly what you are doing. If you had those strap-ons we saw, that’s exactly it even more!”

“Oh, OK. So, you said this was the first way?”

“Yup. I’ve probably done it this other way more often. ” I moved away from her, and lay on my back. I rotated so she was down towards my feet, and then I spread my legs, and pulled my knees up a bit. Chantelle was now sitting between my legs, I imagine with a pretty good view. Well, I’d seen every inch of her too. “If you take the vibrator and put it under,” she brought her hand with the vibrator down to position it underneath me, “you can put it in this way too. My one girlfriend really liked it this way while she was going down on me. And you can kind of work up to the vibrator this way – start with some oral, use your fingers, then add the vibrator. Might be a good way to start. Just watch the angle, if you go in wrong and it hits something, it can be a little uncomfortable. So go slow, and let him adjust if he needs to.”

“I still can’t really see what I’m doing.”

“Here, try a couple of things. One way is to do it by feel. Just go a little farther than you did before.” With that, Chantelle reached down and ran her hand over my balls, down under to where her hand was touching my ass. She felt around, sliding her finger up the crack of my ass, stopping when she put her finger on my anus. I jumped.

“Oh!” I said. “Just like that. With some lube, we’d be good to go. But also, this might help you see a little more if you want to.” I pulled my legs up farther, almost pulling them off the bed, exposing my ass more. She stared down at me, and I could imagine she could almost see underneath. Her finger was still on my anus, and I felt her rub around it. “OK, good, after you get the hang of it, you can just do it by feel.”

“Got it.” She said. “Slippery, oral, good to go!”

“There’s one more way you could do it. It’s the most basic, but also the most, um, exposing? So I don’t know that it’s how you’d do it the first time, it depends on the guy. That’s doing it doggie-style. Just picture it. You can imagine.”

Chantelle took a deep breath, and took her hand from underneath my ass. “No, it’s my lesson. casino firmaları Show me. Please. I want to see it.” Chantelle’s voice dropped, and something in it was almost pleading when she said this.

“Are you sure? This is pretty, um, well, you’re definitely going to see a lot.” She nodded, flushed, shifting her eyes on my face now. “OK, I need to move one more time.”

Chantelle scooted back. With that, I rolled over onto my stomach, then slowly got on my hands and knees, with my ass pointing towards her. I heard her catch her breath, and felt her shift on the bed. Not sure what was going on – this was just a demo, after all – I just stayed still. I swear I could feel her eyes on my backside, then felt the bed shift again as she moved closer. I felt her hand on the top of my ass, and then I felt her pull my cheeks open. Then she was still again. I knew she was looking at places that no one had ever looked at for that long. “Hey, you OK back there?”

“Yes.” she almost sputtered. “It’s just… I’ve never been able to just look like this.”

Putting my head on the bed for balance, I reached back with one hand and pulled open the other butt cheek. I was totally exposed, and I had no doubt she could see everything there was to see. She made a small sound. “It’s OK, dirty girl, look all you want. It’s your lesson, it’s all yours.”

I heard her breathing heavily as she stared. She shifted on the bed, putting her left hand underneath me, grasping my very hard cock, then slid her right hand back up over my balls and onto my ass. She stroked along the sides of my crack, avoiding my anus until she got close and finally slid her finger over it. She traced the crack of my ass up to the top, then back down over my anus, all the way over the ridge between my balls and asshole. Her other hand was motionless on my cock as she rubbed all over my ass. Eventually I felt her finger back on my anus, pushing tentatively. I murmured, “Chantelle, you really need some lube if you want to play. Go ahead.”

Glancing back, I saw that she was flushed again. “I… I… really want to do you like this.”

“It’s OK, I’m not going anywhere.” With that, she reached over for the bottle of lube and squeezed some out onto her finger. She brought it back up to my ass and began to rub it into my anus. “Mmm,” I moaned a little to encourage her.

She squeezed a little more lube out, and continued rubbing. Now that she had the lube, she definitely knew how to get it ready. She circled my asshole, and slowly began pushing her finger in, very tentatively. “Is this OK?”

“More than OK, go ahead.” I was almost panting with excitement, and I could feel the pre-cum dripping out of my cock. I pushed back a little, feeling her respond by pushing a little more, and then I had to consciously relax to let her in. I could feel her finger penetrate me, first to one knuckle, then on until I felt her hand on my butt. I assumed her whole index finger was in now. “Oh, God, that does feel good.” I gasped.

She pulled out some, and then pushed back in. “Maybe a little more lube.” This time, she squirted it right on my ass where her finger was going in, and worked the lube around as she was working my ass.

“Better?” she said.

“Ooh, mmm, just take your time, I’m in no rush to go anywhere.”

Chantelle started wiggling her finger, moving it all around inside me. I could sense her watching as I pushed back against her, trying to get her deeper in. My cock was dangling underneath me, rock hard. After a minute, with her finger still playing in my ass, she reached under me and rubbed my cock a few times. She ran her fingers over my head, and then brought her hand around to my mouth. She fed me two fingers, and I sucked them in, tasting myself.

I can’t believe this is happening. Here I was, with two of Chantelle’s fingers in my mouth and one in my ass, after all this time. I swirled my tongue all around her fingers, then she withdrew and moved back down towards my cock again. She continued to finger me, and reached under to continue stroking my cock and balls. I kept pushing back, trying to get more until she finally pushed back with both hands and said, “You know, I can’t go in any further!”

With that, I sensed her reach down and pick up the vibrator. She brought it under me and held it against my cock, still keeping her finger in my ass. “But maybe that means you’re ready?”

“Mmm, I think so.”

Chantelle pulled her finger from my bottom. After what felt like it must have been 10 minutes with her finger in me, I felt empty. Glancing back, I could see Chantelle pick up the lube in one hand and squirt it over the vibrator in the other. She spread it around with one finger, then she glanced up at me.

“So are you really, really, ready?” She asked, smiling.

“Yes, damnit!” I replied. “I’m ready! Go ahead! Please!”

I felt her place the vibrator by my anus. I felt more lube squirt on my ass, I could feel more of it drip down my crack. My legs were trembling. Then I felt the end of the vibrator start to push in. It was a bit bigger than her finger, and she asked “What do I need to güvenilir casino do, oh mighty teacher?”

“Just – push – gently… Oh! Move it around… Now let me… push back…”

She pulled out, letting some more lube drip onto my anus, and then put a little more pressure. I felt my ass starting to open, and I started to push back. “Just hold it – there,” I tried to relax, and pushed back. Suddenly I felt the first two inches slide in. “UH,” I moaned, and was very still for a few seconds while my body adjusted to the intrusion. Chantelle moved the vibrator around, very slowly, then pulled it out a little, and resumed her inward push.

“God, this is so hot,” she whispered. “Watching it go in.”

“Unh huh.” I gasped, still pushing back and trying to relax. There were a few inches in. Then it hit something. “Ooh, you need to angle it differently.” I reached back and took her hand, moving it up to aim the vibrator in my ass so it wouldn’t bottom out. Slowly, slowly, we worked it in, me pushing back, Chantelle sliding it out, then back in, until I felt the base of the vibrator touch my ass.

“It’s in all the way,” she whispered.

“I know. I can feel it.”

“How does it feel?”

“It’s… I’m full.”

Chantelle slid it out some, then back in quickly. “No,” I muttered. “Oh… just keep it in.” She started playing with the speed of the vibration, and pushing and wiggling the vibrator in my ass. “Oh, that’s it, that’s it.”

Holding the vibrator in one hand, Chantelle slipped one hand underneath me to my erection. She clearly had gotten a lot of lube on her hand, as her hand just slid along my shaft as she started to stroke me. “How’s that?”

“Oh, God, even better.” She continued to stroke me as she played with the vibrator in my ass. As I loosened up, she was able to more easily slide the vibrator in and out of me. She began timing its penetration to her strokes up and down my penis. And when she was in all the way, she’d kind of wiggle it around. “Oh, yah, like that,” I panted.

After only a minute or two, the sensations were getting intense, and I could feel my orgasm almost overtake me. I almost fell over doing it, but I had to reach down and grab her wrist. “No, stop, wait, please, slow down, slow down.” She got the hint and just held my penis still.

It still felt incredibly good, but I wanted this to last. And I wanted to touch her again too. “Wait, let me lie down.” She took her hand off my cock, and I rolled to my side, then onto my back, being sure the vibrator didn’t fall out. I reached out and could reach her thigh, but no farther. “Here, move up a little.”

Chantelle shifted so that she was lying on her side, kind of across my leg so she could reach the vibrator and my cock again. She put a little more lube on her hand and returned it to my shaft, taking the vibrator with her other hand. She ran her hand down over my balls, and back up. Closing my eyes, I could imagine that all she could see now would be a little bit of the vibrator emerging from my ass.

Chantelle was close enough now that I could reach out and run my hand up her thigh to her pussy. She propped one leg up, and I was amazed to find that she opened easily to my touch. She was warm, and wet, her juices running freely again.

“God, you are wet again.” She shivered as I ran a finger through her lips, dipping a little into her.

“Mmm. I’m not surprised. It’s the lesson.”

We lay like this for a few minutes, my hand playing in her pussy, while she stroked my penis and played with the vibrator inside me. She found she was able to take both hands off the vibrator, keeping it pushed against the bed, and use two hands on me, sometimes both on my shaft, sometimes one on my balls. I alternated between looking at her very wet pussy and down at her, where she seemed to be focused on my cock, and looking at the vibrator where it was inside me. She gripped it and slid a little bit in and out, but couldn’t get much motion because I was lying on it.

“I can’t really slide it in and out in this position.” She told me.

“Uh… It’s OK. Really. Just like that is good, just keep it in.” The vibrator was pushed all the way in, vibrating against me inside, and it felt great. Chantelle returned her attention to my cock and balls.

I knew I wasn’t going to be able to last much longer. “Oh, I’m so close,” I muttered. “Just a little more.”

“I want to watch you come.” Chantelle said. I lifted my hips a little, thrusting through her hand, and she grabbed the vibrator, sliding it out a bit and back in. She began stroking my cock faster.

“Ohh!” I said, and she pulled the vibrator out further before pushing it fast back in. I pushed down on the bed, then lifted myself back up again for her to slide it out a little. “Ah.. Noo… Mm. Yes!” I pushed back down on the bed one final time, forcing the vibrator back as deep as it would go while she stroked me, and then I erupted. Jet after jet of come shot from my cock as I wriggled on the vibrator trapped inside me. Chantelle had me pointed upward, and my come splashed down on my belly and chest, and on her hand as she milked me. My hips bucked, my ass trying to push the vibrator out, my hips simultaneously pushing down on it to keep it in. I don’t know how many times I squirted, the spurts getting smaller, as Chantelle continued to forcefully stroke my cock until I couldn’t take it.

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