Ally Explores Ch. 02

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Double Penetration

This is chapter two of a three part story. Each chapter sort of stands on its own, but they will make more sense read as a set.


Given the previous night’s activities and wine consumption, I was a little surprised I woke up fairly early Saturday morning. As I lay in bed, I recalled snippets of sexy dreams that had kept my sleep restless, including one where an anonymous man was sitting between my open legs working a huge vibrator deep into my pussy. I was sweating, and getting moist. I was amazed that I had the urge to once again start kneading my clit in search of a release. I needed to get things under control, so I jumped into a lukewarm shower to regain my focus.

When I got to the kitchen, Kate was already there with a coffee. She had some serious bed head hair and was wearing a long t-shirt over her panties. “Morning Ally,” she said. “I hope I didn’t wake you up.”

“No, not at all. I have to get up early for work and it just carries over to the weekend. Thanks for making coffee, I really need one this morning.”

“Yeah, I did too. Maybe had a glass of wine too many,” Kate laughed. Then, growing serious, she looked me in the eyes. “Ally, I really hope you aren’t uncomfortable with what happened last night. Once I got turned on, I kinda got carried away.”

“I’m still a little confused, but I’m not uncomfortable,” I said. “You really opened my eyes to different ways of looking at sex in a relationship. I like the “trusting and enjoyable” standard you came up with. I think that’s a better way of looking at it. I need to re-evaluate some of the boundaries I’ve set in the past. We went way past anything I could have imagined happening. If it weren’t with you, I’d be mortified. I’m a bit uneasy about the how and the why of last night, but I certainly enjoyed it. And I have to admit, I spent a lot of last night in bed thinking about sex. I had some pretty wild dreams.”

“Do tell Ally, what kind of wild?” Kate asked with a grin on her face.

“I’d rather not go into the details,” I said with a little smile. “But they were mostly me in sexual situations I haven’t previously tried.”

“Well I’m not ashamed to admit when I went to bed, I got myself off again thinking about our couch session,” Kate laughed. “I was still hot and bothered and had to take the edge off to even get to sleep.”

“I did too,” I said, blushing. “It’s like I became a sex addict in just one evening.”

“There are worse things to be addicted to!” Kate giggled. “And I’m glad your mood is picking up. That was one of the goals of my trip. The other is to do some serious shopping. Let’s get ready and hit the town.”

“Sure thing,” I said. “I know a nice spot we can stop at some point for lunch. They have great Sangria. And Kate, thanks for coming down. I needed a pick me up. I’m not sure I knew I needed the, you know, other stuff, but it’s all good.”

“Hey, no problem Ally. It’s the least I can do. Give me twenty minutes in the shower and I’ll be good to go.”

We took the “El” to the Magnificent Mile. It was a beautiful early fall day, clear and still warm, but without any of the stifling Midwest summer humidity. Shoes were definitely the focus. Kate’s feet are really small and she has trouble finding current style shoes in her size. And Chicago stores are more progressive and on-trend than what she can find in Detroit. I have a couple of favorite shops near Water Tower Place, and they didn’t disappoint. Kate bought half a dozen pairs of shoes. We spent the rest of the morning wandering through the various boutiques, occasionally trying something on. In the end though, the shoes were the only purchase.

I have a favorite Mediterranean restaurant on Michigan Avenue that has outdoor seating and serves really creative variations of Sangria. Today was perfect weather for both. We got a great table for people watching and settled in with a pitcher of kiwi-honeydew Sangria for a comfortable lunch. After the waitress cleared the lunch plates away, we sat in the sun working to finish the Sangria.

“I’m sorry you didn’t find anything you wanted to buy today,” Kate said. “I feel like I just dragged you all around Chicago for nothing.”

“Hey, it’s really no problem. It’s fun to have an excuse to come downtown. I’ve been kind of living in a cave the last couple of months. Besides, we still have the afternoon to shop some more.”

“What are you looking for?” Kate queried.

Predictably, the alcohol had loosened my tongue a bit. I leaned closer to Kate. “I think I’d like to buy a vibrator.”

Kate threw back her head and laughed. “Really? Sounds like someone has really caught the bug.”

“I guess so,” I admitted. “I’ve never gotten off like I did last night, and I can’t imagine not doing it again.”

“Well then, what I recommend is that we do some on-line shopping,” said Kate. “That’s how I buy mine. You can read reviews and compare the different types, and they all get shipped direct to your door in discrete packaging.”

“Yeah, brazzers that would be good, but I’m kind of thinking I want one for tonight,” I said, glancing nervously at Kate.

Kate smiled. “Are you talking about a round two on the couch?”

“Is that too kinky?”

“Nope,” Kate said. “I’m all in. But that means we need to find an adult store. And it needs to be focused on women. I’m not going to one of those sleazy places where guys are hanging out in video booths and the clerk is mentally undressing you. They are just disgusting. Let me do some internet searching.”

For several minutes Kate was glued to her phone. She was frowning, shaking her head and muttering while she was at it. Then she looked up brightly. “Found one. It specifically caters to women. It looks to be a good one, and it’s a short ride up to Belmont on the El.”

A short time later Kate was pulling me into the store. I was amazed. It could have passed for an upscale clothing boutique. There was soft lighting and the smell of incense. I could see shelves full of a variety of sex toys. Some in their boxes and some out on display. They seemed to come in every shape, color and size. There were also racks of lingerie and displays of candles, lubricants and body oils

As we stood in the doorway, a pretty brunette, who looked like she was about seventeen, came bouncing over to greet us. She was about my height, with a toned body and obviously firm breasts, shown off by a tight cotton top with the store’s name embroidered on it. She was wearing form fitting black leggings and tennis shoes.

“Hi. I’m Morgan. Can I help you find something?” she asked.

“You work here?” I blurted out, instantly regretting it. “I mean, you’re so . . . . .”

“Young?” she said, finishing my sentence. “I get that a lot. I’m nineteen and going to college in town. I need to work to foot the bills and I’m too young to bartend. This place pays really well, and the employees get to test all the merchandise, which is a great benefit!”

“You’ve tried all these?” I asked, pointing to the shelves.

“Quite a few, but not all of them. There are new products all the time. It’s hard to keep up. But it’s fun trying,” she said grinning. “So, what are you interested in? If you have an idea of what you are looking for, I may be able to make some suggestions.”

“Ally is here to buy her first vibrator!” said Kate happily. “Why don’t you help her and I’ll just browse around.” She wandered off to look at the lingerie.

“Your first toy, huh?” said Morgan. “Well, you certainly have a lot of options.” She winked at me and waved her hand towards the toys on the shelves at the ready.

“I don’t even know where to start,” I admitted. “I’ve only used one vibrator, a rabbit, and I enjoyed that.”

“Well there are some easy assumptions we can make right away. I highly favor rechargeable toys instead of conventional batteries. They hold a charge longer and you never find yourself in the mood, but have to delay to run to the convenience store to stock up on double A’s. We also only sell toys made of the highest grade, safe materials that are easy to wash.”

“Oh, okay good. That hadn’t even occurred to me,” I replied.

“Do you mind if I ask you some blunt questions about what you find pleasurable?” Morgan asked. “It will help me narrow it down for you.”

“I guess not. Go ahead.”

“Okay. First of all, are you looking for clitoral or vaginal stimulation, or both? Some vibrators concentrate on one or the other, some try to do it all.”

“Both I guess,” I meekly replied. “I mean, I enjoy intercourse, but my biggest orgasms start when something is rubbing my, um, you know, clit.” I knew I was blushing, and I also knew I was starting to be a little turned on.

“All right, that’s great. And are you looking for a toy for solo masturbation, or is there going to be a partner involved?” Morgan asked, glancing over at Kate.

“Oh no, Kate is just a friend,” I replied hurriedly. “And there’s no boyfriend in the picture. I think for now it will just be me, um, masturbating.” Now I was definitely aroused.

“I get it. Sorry, I didn’t mean to embarrass you. We get a lot of women couples in here. So, vaginal and clitoral, solo masturbation. Last question, in terms of size, any preference on length and girth?”

“Length and girth?”

“Yes. Most of the insertable vibrators are penis-shaped, or some facsimile. Some women like longer vibrators that can reach the deeper places. Some like thick ones that fill, and sometimes even stretch their vagina. Some prefer smaller ones that can be more easily maneuvered. The small ones tend to not leave you as sore as well, although a healthy application of lubricant can really help with the larger ones. I don’t find it to be an issue,” Morgan said with a knowing smile. “To give you an idea, the average male penis is about five and half inches, fully erect. Seven inches is considered big. Nine and up is huge. And the average girth is about five inches of circumference.”

An cuckold porno image flashed into my mind, unbidden, of Morgan spread-eagled on a bed, head tilted back and mouth open. Naked from the waist down with her shirt and bra pulled up over perfect tits. She was sliding an enormous vibrator into a completely bald pussy. I gave my head a shake to clear my brain. I knew I wasn’t into girls sexually, but in my state of excitement it was an intensely erotic thought.

“How in the world do you know all this?” I asked, trying to maintain some focus.

“Oh we go through a big training program here at the store. The owner believes that one of our key roles is to educate, debunk and demystify. It’s the main reason why we are encouraged not to introduce slang into the conversation unless that’s what our customer is comfortable with. Here are a couple of other tidbits. The average woman’s vagina is five inches deep – less than the average penis length. The average clitoris is less than an inch long but can be well over an inch when you are turned on. The average guy only ejaculates a table spoon or two when he climaxes, but younger guys who have abstained may produce half a cup. So don’t believe all you see in porn films.”

It was an effort to process all the data. “I don’t know. The only vibrator I ever used was pretty normal sized. I think maybe I’d like something a bit bigger? But still realistic?”

“Perfect. I could show you a couple of dozen vibrators that I think you would enjoy, or I can narrow it down to two that I highly recommend for you to choose from. I’ve found that once a customer makes an initial choice and gets used to the toy, they come back and buy others to round out their collection. Different vibes for different moods I like to say.”

“That’s exactly right,” interjected Kate, appearing over my shoulder. “An old boyfriend bought me my first one and it was total crap. Typical guy choice. Looks not effectiveness. But it piqued my curiosity, so I bought a vibrating dildo on my own. It was good for a while, but I got bored so I ordered a wearable clit vibrator. Mr. Purple was the fourth or fifth one I bought, I think.”

“A wearable vibrator? What does that mean?” I asked.

“Hold that thought,” said Morgan. “One of my two recommendations is a wearable. Here, let me show you the two I think would be good for you to start with.” Morgan turned and led us to the display shelves, showing off her sculpted bottom as she walked. I was betting she was a cheerleader in high school. She had the look and the body for it.

She picked up a pink, rabbit style vibrator that had an “employee favorite” card in front of it. “This is my favorite of the rabbits. If you want both vaginal and clitoral stimulation, the rabbit style is the best. This one has a great rechargeable battery that lasts up to two hours. I know, I almost passed out trying to run the battery down. It’s seven and three quarters of insertable length, and five and a half inches around. So it’s going to fill the average vagina right up. And it has dual motors, one for the ears and one for the shaft. It has ten different vibration patterns, and ten different intensity levels. And level ten is about the strongest of any vibrator I’ve used. I’m not kidding when I said I almost passed out! The shaft rotates so the vibrations are distributed throughout the walls of your vagina.” She handed the display model to me. It was made of a pleasant, soft material that almost felt warm to the touch. I could feel a dampening in my pussy as I eyed the toy, imagining it lodged deeply in me.

“And here is the second one. It’s what they call a butterfly. This is a bit different, because it’s a wearable.” She held out a jade green toy that had a shorter insertable shaft that was curved in the shape of a J. It was attached to a butterfly-shaped base that had some small silk straps, similar to bra straps. “So the big benefit of wearables is that they are hands-free. You position the vibrator, fire it up with the remote control, and sit back for the ride. This one inserts so that this small shaft is up against your G-spot. The butterfly sits over your vulva with the head and antennae between your labia and on your clit. You just put the straps around your legs and waist to keep it in place. Or you can take the straps off and just wear tight panties so that it doesn’t move. That’s what I do. Downside to that is a partner can’t see as much of what is going on. Same dual motor design as the rabbit, so just as powerful. The remote is Bluetooth, so no wires. Rechargeable too. And if you are feeling adventurous, you can wear this in public. It’s a bit loud, so I wouldn’t use it in the library. But give your partner the remote and go to a club and it can be a very fun evening. My boyfriend brought me to climax while we were grocery shopping when I tested this one. I wanted to punch him, but I kind of asked for it.”

“Oh my god, that’s great,” cried Kate. “I have one kind of like this, but hadn’t thought about going czech porno out with it in. I usually use mine when I’m alone and just want to snuggle in alone and watch porn. With my hands free I can control the TV or my tablet.”

“I don’t think I could use it in public, but I like the hands-free part. I’m going to buy both of them,” I said, surprising myself just a bit. I was now completely turned on and feeling that itch again. I glanced nervously at my jeans. I knew my panties were soaking, and was hoping a wet spot wasn’t showing through. Thankfully it wasn’t, but Morgan caught my glance.

“You know, once you purchase the toys, you can take them back into our changing rooms and try them out.”

“Really? You allow that?” I said. Although I knew I could never do that.

“Yep. We used to try to prevent it, but having these kinds of discussions tends to get people hot and bothered, and women were sneaking back there all the time anyway. So now we just go with it. Employees aren’t allowed to, even though by the end of most days, my vagina is flowing like a river. I bring extra sets of panties to work to change into during my shift. And then when I get home, I am usually more than ready for more product testing,” Morgan said giggling.

“Well, thanks for the offer, but I think I’ll just try these at home,” I replied.

“Fair enough. I’ll ring the sale up. Anything for you?” Morgan asked, turning toward Kate.

“What’s your opinion on this new sonic clit vibrator, and these vibrating nipple clamps?” Kate asked. She’d obviously been doing some serious shopping of her own. She was holding a pink and gold device that was shaped like a rounded bar of soap with a cup-like protuberance at one end.

“Both are great. You know that your clitoris is just the tip of a much larger nerve bundle that the sonic waves can bring into play. You nestle that indentation directly around your clitoris and you are off to the races. Sensational orgasms. And if you like to have your nipples involved, those are great clamps. They are rubberized and have a lighter grip than most of the others, so it’s mainly vibration, not pain.”

“That’s what I was hoping,” replied Kate. “Ring those up too. Ally, I’m buying. Consider this my contribution to you redrawing your boundaries.”

I was still trying to process the idea of nipple clamps. I’d heard of them of course, but I still had my opinions of anything in the bondage arena. I was intrigued by them though. I realized that me trying nipple clamps wasn’t out of the question. Just another in the list of surprising developments this weekend. It was a little overwhelming. I didn’t even try to argue with Kate about paying.

“Are you sure you don’t want to take one of those for a spin before we go Ally?” Kate asked. “I’d be lying if I said I wasn’t interested in trying this sonic vibe out right now.”

“No. I’d be too nervous. But you can if you want to. I’ll just wait for you.”

“Well, if you really don’t mind . . . . I really need a quickie. I’ll be right back. I don’t think it will take too long,” Kate said laughingly. She turned and walked back to the changing rooms, giving me a little shrug and wave of her hand as she entered the first one. I could see that unlike changing rooms in department stores, these had full doors.

“She’ll only be a minute,” said Morgan confidently. “If she’s already turned on, that sonic vibe will get her off almost immediately. The first time I used it, I came in less than two minutes. The nice thing is, since it’s sonic, you don’t become desensitized because of vibrations. I’ve had a session with mine where I kept it directly on my clitoris for almost an hour without it being uncomfortable. I orgasmed thirteen times.”

“Thirteen?” I gasped. And I thought the two in a row on the couch last night was a lot. I was already thinking that I needed to add one of these to my collection.

True to Morgan’s prediction, Kate emerged from the changing room in less than five minutes. Her faced was flushed, and she was walking a little unsteadily as she approached us. “Unbelievable. I’m not sure I can walk back to the El. I came three times, and I think I could have gone on forever. Definitely satisfied with the purchase!”

We laughed at that and then said our goodbyes to Morgan. “I hope to see you in here again soon,” she said as we were leaving.

“Oh I think you will,” said Kate. And I didn’t disagree. We made our way back to the El and went back to my apartment. The after effects of the Sangria were starting to kick in, so we agreed to take a short nap to re-energize ourselves.

“I’ll set an alarm for an hour,” I told Kate. Then I decided to take another step towards new boundaries. “And when we wake up, can you help me shave my pussy?”

Kate raised her eyebrows. “Of course Ally, if that’s what you want. Don’t think that it’s required though. You’re beautiful as is.”

“Thanks Kate, but I want to try it.”

“This weekend, what Ally wants, Ally gets. Wake me up in an hour.”

When the alarm went off It felt like I’d been asleep for a year. I dragged myself out of bed and almost opened Kate’s door without knocking. But given the level of sexual activity so far this weekend, I decided I’d better knock first in case she was “up to something.”

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