Teaching Chantelle Ch. 06

"I know what you need," Chantelle said. "You know, you told me last night I could have your ass."

"I did?"

"Yes, you did. I want this," she whispered, managing to push right on my asshole, "but you'll need to move."

"Uh-huh," I muttered, trying to push forward so she could get at me better. But then she pushed me to the bed and hopped up, going to the bedside table where we had left our box of toys Bringing it to the bed, she plopped down beside me again, reaching her hand out to give my cock a couple of strokes before starting to rummage through the box. Jess sat up on the other side of me to watch Chantelle, and continued to play with my cock as Chantelle held up her biggest dildo.

My eyes widened, and Chantelle laughed at my expression. "Now, I know you could take this, but I wouldn't want to scare you." She put the dildo back in the box and pulled out a medium-sized black butt plug. "Now, this one, you know you can handle." It was a toy we'd used before, a plug that was quite a bit narrower at the base than at its biggest point, so it stayed in better than many. "Get up. Hands and knees." I obliged feeling Jess shift down the bed. My ass was up, exposed to both women. I put my head down on the bed, knowing what to expect, but still jumping when Chantelle first touched my asshole with cold lube.

Chantelle began to rub my asshole, her finger entering me slightly. I sensed her lubing up the plug, and then I felt her hand separating my cheeks. I felt the smooth silicone of the plug against my anus, rubbing over me... and then Chantelle began to push it in. I felt my asshole opening, easily at first as the tip entered, but then the resistance increased as the wider part of the plug reached me. A hiss of breath escaped from my mouth.

"Relax, relax," Chantelle murmured, much as you would say to an animal you were trying to calm. "You can take this... You've taken it before. Just open up... You're such a good boy." As she was murmuring, she was putting constant slow pressure on the plug, sliding it in, little by little. She stopped, pulling it back out partway, letting my ass adjust to being stretched, and then pushed again. She reached under me, stroking my cock, letting it know that would have attention too. She resumed her push inward. "It's almost in. Just relax."

"Oh, it's big... Go slow, slow..."

"I know. You're taking it so well. It's almost in. Just relax." And with that, Chantelle gave a final push, and the plug slid home. I groaned as I felt it touch me deep inside, my ass clenching around the base of it. I raised myself from my hands on knees, feeling the plug adjust inside me. Chantelle reached out and took Jess's hand, bringing it to touch the base of the plug where it entered me. She pushed, and I moaned. Chantelle reached around and took my cock in her hand. Now that the entry was complete, I hardened almost immediately.

"I knew that would do it!" I turned to Chantelle and kissed her hard, thrusting my cock in her hand. Jess was there too, her hand under me, and I kissed her before turning back to Chantelle. The idea that she had just inserted the plug into my ass in front of her friend was so dirty that I found myself even more excited.

"I want to put yours in too." I said it without thinking, not thinking about how Jess would react, or maybe just not caring at that point.

"Maybe later. Right now... I think Jess was ready for you?"

Jess reached for my cock again, stroking it. I kissed her, both of us kneeling in the bed, and then I pushed her upper body down, forcing her back to her hands and knees and shifting behind her. I leaned down and gave a quick nip on one cheek, and then moved across her leg to kneel behind her. My cock was rock hard, and I rubbed it between her lips for just a few seconds before leaning in. She was definitely still ready, and Jess made a noise as I slid into her easily.

As my hips reached her buttocks, I savored her heat and wetness for a second, similar to Chantelle but somehow still different. I began sliding in and out, and Jess quickly began pushing back against me. "Deeper!" she muttered, and I begin thrusting my hips. I put one leg up so that I could push in harder, holding onto her hips to pull her towards me at the same time I was thrusting. She began making a low noise every time I hit bottom, but it was definitely a "keep going" noise. I could feel the plug shifting slightly in me as I thrust.

Looking down, I saw Jess's pretty asshole above my cock. I wet one finger in my mouth and put it on her anus. As I thrust, I began to work my finger in, pushing a little more each time I thrust. Soon it was into the hilt, and Jess was truly full of me. I wiggled my finger as I fucked her, and the sight of my finger in her ass and the feel of her on it was becoming too much. I could feel my orgasm building, and as I began thrusting even harder, Jess moaned even louder. She had her head down, being pushed into the bed, and I could feel Chantelle touching her, and my balls, as I thrust.

I tried to slow my thrusts as my orgasm built, focusing on pushing into Jess as hard and deep as I could. She was murmuring, "Oh... oh.... Oh..." in rhythm to my thrusts. "Oh... Yes... YES. I'm gonna... oh, THERE, NOW, Now..." With that encouragement, I gave a final two hard thrusts and came too, forcing my cock deep as I felt my first explosion, shooting my semen inside her. I felt her pussy tighten around me, I felt the fullness of the plug in my ass, and Jess was there with me, pushing back as I thrust and pulsed several times, trying to keep up the hard rhythm that had brought her over the edge. I finally felt the last pulse of my ejaculation and had to stop. I froze and then fell onto her, pulling my finger from her asshole and catching myself on two hands. Jess dropped her hips to the bed under me, trapping Chantelle's hand against her pussy, my hips pinning her to the bed as we both collapsed.

Chantelle wriggled out from under Jess and put her arms around us. We lay in a heap for a few minutes while we caught our breath. Chantelle helped me remove my plug, and I felt empty once it was out. When we finally stirred to head to the shower in a group, we all shared a kiss, Jess tasting like a combination of me and Chantelle, and me with a flavor of Jess on my lips. We weren't sure what we were doing that day, but it was time to get out of bed. We washed each other thoroughly in the shower, feeling very close. We'd have to see what came next.

**********

We were all quiet and a little subdued as we made breakfast together. Something about having our clothes back on after our long night changed the mood. The raw sexual mode we had shifted into was different by the light of day -- not quite awkwardness, but definitely different. I suspected that we were all a little worn out and needed some time to recharge. As we made breakfast, I made it a point to kiss both Chantelle and Jess. It was as if none of us were quite sure what the day would bring as we moved around the kitchen. We finally sat down to eat.

"What's the plan for today?" I asked.

"Well, I guess I'll head home... although I'll need a ride from someone," said Jess. "I have to go to a late dinner for work tonight... some out of town reps are coming in for a meeting, and god forbid we leave them to have their own dinner." She rolled her eyes.

"That's no problem," Chantelle responded. "It's Sunday, and I need to run out to OfficeMax anyway. But that's the only thing on my agenda."

"Is it going to be as hot as yesterday?" I asked. We checked the weather app, and yup, it sure was. "Well, OK, that rules out doing too much. I need new shoes, maybe we can go to the mall while we are out getting your work stuff?"

"Sure, let's go hang out there a little bit. Then we can just relax. And recover!" She reached out and gave my crotch a gentle squeeze. "When's your flight, Tuesday? I'm going to have to go in to work tomorrow."

"Yeah, but I don't want to think about it. I'm just going work remotely from here tomorrow. But I'm not ready to go!" I reached out and took Chantelle's hand in mine. "Last night was fabulous. I think I'll be planning a trip back soon."

"We have a couple more days!"

"Oh yes, for sure." Then I realized Jess was looking a little uncomfortable. "Jess, everything OK?"

"Oh, it's all fine. I was just thinking about you two. I've got work tonight, and work tomorrow. And you do too. I just didn't know if... well, never mind, we're all busy, that's all fine."

Chantelle suddenly looked stricken. "No, Jess, we didn't mean..." She looked at me. "At least, I don't think we meant... We haven't talked, but I was thinking, that maybe you'd come by tomorrow? I mean, if you want to?" She leaned over to me to whisper, "Is that OK?"

"Oh, yeah, definitely!" I reached across the table to take Jess's hand too. "I mean, of course, if you want to. Are you free to join us tomorrow?"

Jess's face brightened. "I sure am. I just didn't want to impose."

"Oh no. Maybe we can go in the hot tub for a while. We'll find something to do, I'm sure." I cocked one eyebrow at her, and she laughed.

"I'm sure!"

I had an idea. "In fact... I wonder if we should make a field trip before then. Maybe for some toys, just for us? Then we'd definitely have something to do."

Chantelle chimed in, "The Hustler store on Metro Parkway is easy to get to. We can go there after work."

"Why am I not surprised you know where it is?" I teased.

She laughed. "Ok, so maybe I've been there once or twice. But remember -- you're the one who bought me my first vibrator, after all, so you shouldn't be talking!"

"I'm definitely not complaining!" Our mood was lighter now that we knew that Jess was going to be with us again.

"What are we going to look for?" asked Jess.

"Good question. I don't know exactly. But I'll bet whatever toys Chantelle has, she doesn't have them for three! We'll see what grabs us. Have you been there?"

"A long time ago, maybe. I think I know the one you mean, but I'm not sure." She glanced at her watch. It was approaching 11. "Maybe I can just meet you there on the way home?"

"Sure, maybe... meet at 5:30? That will give us plenty of time."

"Great!"

**********

The Hustler parking lot was only half-full when we arrived the next day, and we had no trouble finding Jess. We walked in together, and were greeted by a pair of goth-looking salespeople, one man and one woman, both in leather vests.

"Hi, welcome to Hustler," the woman said. Her nametag read "Heather." "Have you been here before?"

We looked at each other. "I've been in other stores, but not here," I offered.

"I've been here, but it's been a while," said Jess. Chantelle nodded in agreement.

"Well great, thanks for coming back. You picked a great time because it's our customer appreciation sale! All of our returning customers get a goodie bag. There are samples sizes of some of our best selling products in here. Jim will give that to you... thanks Jimmy." As she spoke, the other salesperson was handing us each a small bag that said Hustler on the side. "You also get a raffle ticket. We have a drawing every hour for some of our featured products," she gestured to a table behind her, "but you do have to be present to win." Glancing at her watch, she said, "Our next drawing will be in 15 minutes, so your timing is good!"

We dutifully wrote our names on our tickets and dropped them in the bowl on the table. We looked at the display there. They had two vibrators, a dildo, a set of anal beads, a sequence of three butt plugs ranging from beginner to medium to large, a set of ben-wa balls, a cat-o-nine-tails, and some assorted lubricants and oils.

Chantelle picked up the set of ben-wa balls. "What are you supposed to do with these?"

Jess answered frankly. "You put them in your pussy and either just walk around with them, or you can squeeze them for exercise."

"They don't fall out?"

"No, you have to push down to force them out," she smiled. "It's been a while, but they're kind of a turn-on to wear."

"Hmm." Chantelle seemed unconvinced. "I suppose having something inside my pussy all day might do that." She picked up the anal beads. "I have some beads at home, so we don't need this. And I have a couple of vibrators... you can blame Dave for that!"

I looked at her indignantly. "Me? I seem to recall that you liked them!"

"And who doesn't like a good vibrator?" chimed in Jess. "Or two!" I added.

"OK, you're right, I do like them," admitted Chantelle. Glancing around to be sure no one else was listening, she came closer to us, looked at me, and murmured in a lower voice, "And yes, sometimes I even like two."

"Mmmm," I said, and seeing no one was right there, I reached out and put my low on her butt, so it was really just over her asshole, and gave a squeeze. "We'll have to give you some attention here later." She pushed back against my hand, just a little. Message received.

Heather was coming back over to us.

"Is there something specific you're looking for today?" We looked at each other again, and laughed a little nervously.

"Um... I don't think we know exactly what we want. Maybe we'll know it when we see it."

"OK, well please feel free to browse. Clothing and videos are on this level. Most of the toys are upstairs. Vibrators and dildos are on that well," she pointed above us to the left, "and that includes strap-ons. Anal toys are on the opposite wall," she pointed up to the right, "and the BDSM section is towards the front." She smiled at us. "I'm sure you'll find something exciting. It's always fun when friends shop together!"

We thanked her, and started wandering around. We bypassed the videos, and spent a few minutes wandering the aisles of sexy clothing, speculating on what would look good on each of us. I made note that both women seemed to like the idea of lacy push up tops, Jess in a bustier style with sexy panties, and Chantelle just with a top and boy shorts. Jess preferred black to go with her dark hair, while Chantelle preferred red. Jess made a point of taking the outfit Chantelle liked best and standing behind her in front of a mirror in the back corner, reaching around to hold it up against her. They looked very sexy standing together like that, especially when Jess cupped her hands under Chantelle's boobs to see if the cups fit. From that position, Chantelle could turned her head back over her shoulder to give Jess a brief kiss. "I think it fits!"

There wasn't nearly as much clothing in the store for men, which we agreed was totally sexist. Eventually, Jess and Chantelle picked out a cock pouch with a g-string for me. I rolled my eyes and tried to tell them that I didn't need anything, but they shushed me, and Chantelle said, "Just think how that string is going to feel up against your rosebud. It's a very sexy feeling. Trust me, I know." She came close to me again and whispered, "I'm wearing one now, and I can feel it against my asshole when I move."

I gave a little gulp. "Oh really?" She nodded and smiled at me coquettishly, and then flounced -- I couldn't think of another word -- over to Jess, saying "I think it's time to go upstairs! Dave has heard enough about underwear."

We were halfway up the stairs then an announcement came over the store loudspeaker that they were about to have their 5:30 drawing. Standing on the landing, we watched as Jim made a big show of mixing the tickets in the fishbowl, and then reached in to pull out three tickets in sequence. "Our first winner gets a 6 ounce bottle of Moist lubricant. This water based lubricant is good for all of your bedroom activities, and washes off easily when you're done." He went on for a moment longer with an obviously pre-practiced advertising pitch. "And this prize goes to... Bob!" He looked around, holding up the ticket until a young guy walked up, handed him the other half of the ticket, and took his price. The salesperson repeated this for a second item, a bottle of toy cleaner.

"And now our grand prize of the hour. The winner gets to pick one item from this table of toys!" He gestured to the table we'd been looking at earlier. "And the winner is, Chantelle!" Jess and I gave a hoot, as others in the store gave some half-hearted claps and turned to look at her. She muttered, "Me? I never win!"

"Come on down, Chantelle. We know you want something on this table." With that comment, Chantelle turned red and looked ready to die. She never liked to be the center of attention.

"Do you just want me to get it?" Chantelle nodded and handed me her ticket. "I'll find you upstairs in a minute."

"Thanks Dave." She gave me a little kiss.

I walked back down to the table as the women went on upstairs. Turning in Chantelle's ticket, I looked over the items on the table. I knew most of what she had in her collection of toys. I knew she was OK on vibrators, and she had said she had some anal beads. That left just a couple of items. I looked at the three sizes of butt plugs they had on the table, and finally picked up the medium sized one. It was similar to the one I'd had inside me first thing this morning, but the shape was slightly different. "How big is this?" The salesman showed me where the dimensions were on the side. Heather had come over, and offered "That's actually a really nice size, athough it does depend a little on the person it's for. The bigger ones can be too big for many people, and a lot of people find that the small one is too small after they use it just once or twice. This one fits well, and the way this base works, it's very secure."

"Thanks, that sounds perfect. This looks like it should work well."

"Great!" Heather wrapped it up and put it in a bag. "Just be sure to tell them at the checkout counter to check with us if there's any question that you won it."

"Thank you!" I walked upstairs, finding Jess and Chantelle looking at a set of fancy vibrators on a center table.

"What did you pick?" Jess exclaimed.

I showed them the plug. "Oh, that's interesting," Jess said. "You think you need another one after this morning?"

"Is that for me?" asked Chantelle. "You have a thing about my ass, Dave."

"You bet," I grinned. "I think it's a good size. Not too big, not too small. As to whether it's for you, well, we'll see."

"Who else would it be for?"

I raised my eyebrow and glanced at Chantelle, then Jess.

"Oh, you think Jess might be interested?" Chantelle asked.

"Well, is anyone else coming?"

Chantelle poked me, then smiled. "Of course not. We'll see what happens."

Jess smiled. "I'm game. Dave did seem pretty interested in my ass this morning." She glanced at me. "And... it was pretty hot watching you with Dave. And he definitely enjoyed the plug."

"Mmm, he did, didn't he?"

I just smiled.

"Do you have another one?" Jess asked Chantelle.

Chantelle answered, "I actually don't know if I have another one. I've had a couple over the years, but I don't think I've seen another one since I moved."

"How do you lose something like this when you move?" asked Jess.

"Don't ask! Strange things go missing when you move." She shook her head. "Anyway, if you think you want another one, we should look."

We left the center display and walked over to the shelves of anal toys. We agreed the 3-inch thick black plug was not for us, and neither was the plug with the attached pony tail. I explained to Chantelle, "Out here in the west, with horses around, you might find someone into pony play."

Chantelle shook her head. "I'm all about the role play, but being a horse? I think there might be better ideas."

"Well, to each his or her own, I guess."

We looked at more beads in several sizes, and various longer prostate massagers, and various sizes and shapes of more typical butt plugs, comparing how easy they would be to use and even if they'd stay in. We settled on a model very similar to what we had won in the raffle. "So, let's get one of these?"