Ally Explores Ch. 03

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


After Kate left, I cleaned the apartment and then went grocery shopping. I spent the afternoon doing some cooking for the week. Of course, I had NOT forgotten Brett and Kate’s proposal and it rattled around my brain for most of the day. That night, I remembered the conversation about the Sybian and got on my computer to do some research. What I found were dozens of videos of women riding a saddle-type contraption with powerfully vibrating and rotating dildos. I watched their eyes roll back in their heads as they came. I saw them collapsing in a quivering heap after multiple, screaming climaxes. I watched one woman blow her partner while he ran the controls until she was moaning around his cock as he came in her mouth. I was too spent from the weekend’s activities to play with myself, but the videos were incredibly arousing, and I marveled at the idea that Kate had probably used her Sybian to experience that level of pleasure.

All week I was distracted by the play weekend proposal. And every time I thought about it, my pussy moistened. I started to imagine specific scenarios that might occur. I found myself repeatedly recalling images of Brett’s monstrous cock. On a primal level, I knew that I wanted to do it. On the other hand, it would move me from the realm of pushing boundaries doing things to myself, to the realm of pushing boundaries with someone else doing things to and with me. I was very conflicted. Did I really want to see what was hidden beyond that next door? Was I ready for what I might find out about myself? I knew if I said yes, I’d be going past a point of no return.

When I find myself facing a tough decision at work, I sit down and write out a list of pro’s and con’s to help guide my thinking. This may sound ridiculous, but Friday night I poured glass of wine and decided to take that same approach. I wrote “Play Weekend” at the top of a piece of paper with a column for “Pro’s” and another for “Con’s”. After a half hour, I sat back and reviewed the lists. The “Pro” column included: Physical pleasure, strengthen friendship (maybe?), adventure, learn about myself, safe experimentation, weekend on the lake. I chuckled at how out of place that last one was. The “Con” column was much shorter: Ruin friendship (maybe?), unpleasant sex acts (maybe?). I took a big drink of wine and pushed the paper away from me. I closed my eyes and searched my soul the best I could, and then I decided I was probably going to go through with it.

I spent another week contemplating my decision. Every time I thought about it, I got butterflies in my stomach and had second thoughts. I vacillated from “yes” to “no” about a dozen times. That next Friday I got home and went into bedroom to change out of my business clothes. I stripped down and went into the bathroom in my bra and panties. I looked into the mirror, and mentally chided myself for my inability to commit one way or another. I took off my bra and held my breasts in my hands. My nipples were instantly erect and I realized I hadn’t masturbated since the weekend with Kate. I closed my eyes and imagined that they were Brett’s hands kneading my breasts, and that he was standing behind me with his steel rod pressed against my backside.

At this point I was so horny I almost ran to my nightstand, kicking off my panties as I went. I rummaged through the drawer and took out the rabbit vibrator that I had yet to test drive. Hopping up on the bed, I drew my knees up and spread my legs. I wanted to cum very fast, and very hard. I turned everything on the rabbit to the highest settings, put the tip at my vaginal opening and pushed it deeply into my sex. I held it there firmly, and in no time I was riding the waves of two mind-bending orgasms. Afterwards, lying in the hazy post-masturbatory glow, any trepidation I was feeling about the weekend seemed to fall away. I decided to call Kate right away while I had the nerve.

“Hey Kate, it’s Ally. How are things?”

“They’re pretty good, especially now that the weekend is here. We have absolutely nothing planned, so that’s nice. What’s up?”

“Not much. Is Brett there?”

“No. He was out of town on business this week. He gets back later tonight.”

“Okay. Well, here’s the thing. Um. I guess. I mean. I think I want to do the play weekend.”

“You’re kidding. Really? You can’t just THINK you want to girl. You have to KNOW you want to. I don’t want to lose my best friend.”

“Don’t worry. I KNOW I want to. I just came twice on my rabbit thinking about it,” I said, laughing nervously. “I call him Mr. Pink.”

“Mr. Pink and Mr. Purple. That’s great! Oh man, Brett is going to be so excited. He’s going to fuck me senseless when I tell him tonight. And Ally, I’m excited too. I really wanted this to happen for you.”

“Thanks. I’ve thought about it a lot, and I guess the bottom line is that the idea of some more experimentation really appeals to me. I have a couple of conditions though. It would brazzers make me way more comfortable if we can talk about them up front.”

“Sure. Absolutely. Give me the list.”

“Okay. These aren’t in any particular order. First, no cameras. I know you guys are into that, but for me it would just feel like someone was watching us, and I can’t get past that. Also, heterosexual activity only. We are best friends and I want that to be our relationship, and I’m really not interested in the girl on girl stuff. It makes me uncomfortable.”

“I get it Ally. I’ll admit, I’m more than a little intrigued about what sex with a girl would be like, but I know it wouldn’t feel right with you. Brett will be disappointed, because it’s every guy’s fantasy to watch women go down on each other, but if the positions were switched and it were two guys and a girl, it would be like asking him to suck another cock, which he decidedly doesn’t want to do. He’ll get over it. And I totally agree about the camera. It would make it less intimate between us.”

“Good. Another thing I want to have is a safe word. I’m going to try to leave my inhibitions at the door, but as you know, I have a lot of them. I just need an avenue out if something is really a turn off.”

“That’s brilliant Ally. We certainly want to you to be completely comfortable. How about “umbrella”. There’s no confusing it with any other word.”

“Perfect. And then the last thing. Can you, um, bring the Sybian?”

“Ho ho! Someone did some research,” Kate said laughing. “It’s pretty bulky, but I think it will fit in with our luggage. I’ll certainly try.”

“Okay. Then I’m in.”

“Fantastic! So when do we do this?”, Kate asked. The excitement in her voice was obvious.

“Well. I don’t know exactly what the three of us are going to be doing, but I’m pretty sure it would be a good idea to restart my birth control pills, so next weekend doesn’t work. I never refilled the prescription when I last ran out. My dad’s birthday is the next weekend, and I said I’d come down and visit. So it looks like the weekend after that. The weekend of Friday the tenth. Does that work for you guys? God this is strange. It’s like we’re scheduling a dinner party.”

Kate laughed. “More like a play date. That weekend is wide open and Brett is in town that week. We may even be able to take Friday afternoon off and get there early.”

“I don’t have enough vacation banked to do that, but I’ll sneak out as early as I can. It’s a shorter drive for me too, so that will help.”

“We can confirm things the week before. I’ll tell Brett when he gets home and see if there are any questions. The only question may be how many times he screws me tonight. Which I am very much looking forward to answering!”

“Kate you are just horrible,” I said laughing. “Ok then, we can talk as it gets closer. I guess tell Brett I said hi. And enjoy yourself tonight.”

“Will do on both counts! I’m just about creaming in my pants,” Kate said. “Bye Ally.”

I cleaned up and threw on some baggy pajama bottoms and a sweatshirt and made dinner. Afterwards I turned on some music and got comfortable on the couch with a glass of wine and a new book I’d been looking to start. I hadn’t been able to concentrate enough to read while I was constantly debating the play weekend, but with that settled, my mind was clear. It was two hours later when my phone rang with Kate’s number displayed.

“Hey you. What’s up?,” I said. I was surprised when a male voice replied.

“Hi Ally, it’s Brett.”

“Oh, hi Brett. Is Kate okay?”

“Yeah, sorry. Kate’s fine. I knew you didn’t have my cell number and figured you wouldn’t answer a call from my phone. Hey, Kate told me about your decision to join us at the cottage. I just wanted to call and let you know that we are going to do everything we can to make the play weekend a great experience for all three of us. It seemed odd that I would talk to you for the first time the day of, so I figured I’d say hello and tell you I’m looking forward to seeing more of you.”

“If that was meant as a double entendre, it’s pretty clever Brett. I’m looking forward to seeing MORE of you too. Although I’ve seen pretty much everything in the videos.”

“Ha, I should have said looking forward to meeting you. But I definitely want to SEE you too. Hey, just a sec. Kate wants to say something.” I heard some muffled sounds as he handed Kate the phone.

“Hey Ally, we’ll confirm all the logistics the week before. Arrival times, grocery shopping. That kind of stuff. God! Ahhh! Yes!. Oooooh! Sorry. I’ve got to go. Brett’s sticking his cock in me,” Kate giggled. “See. Unh. You. Unh. Unh. On. Umph. The tenth. And the line went dead. I realized Brett had started to give her the fucking she had anticipated. I was surprised that my first thought was one of jealousy, knowing Kate was getting plowed by Brett’s nine inch tool.

Of course the next three weeks are kind of blur for me between work, visiting my family, and fantasizing about what exactly might happen at the cottage. I went back to the toy store and bought the same cuckold porno sonic clit vibrator as Kate, after hearing her rave about hers. Morgan was there again and we had a good laugh about how soon I had come back. Feeling completely comfortable with her as kind of my vibrator coach, I asked her about the Sybian. The store didn’t sell them, so she hadn’t had a chance to try one. She said if I ever got the opportunity, I should definitely try it. I told her that may just happen. Morgan told me how lucky I was and kind of kiddingly asked if there might be some time when she could have a go, all in the name of product research of course. I told her I was traveling a ways for the experience, but that if the Sybian ever got to Chicago, I’d let her know.

Really before I knew it, the weekend arrived. Kate texted me mid-morning that they were on the road and would do all the shopping and open up the cabin. I feigned a migraine headache at work and left for the day at lunch. I got home and rushed through everything I had to do in order to get on the road. As it had been a while, I did a complete shave of my mound. I puzzled a bit about what clothes to take, I guess realizing that if things went well, I wouldn’t be wearing very many. I ended up stuffing comfortable jeans and sweatshirts, along with some loungewear into a duffel. I added a couple of sets of brand new bras and panties that I had picked up for the weekend. They were racier than I usually wear, but of course that was the point. I remembered that Kate had mentioned hikes on the beach and a hot tob, so I added a pair of hiking shoes and a swimming suit. I only had a one-piece and was kind of kicking myself for not thinking about getting a new bikini. And of course, in a large makeup bag I had packed my three vibrators and some lube.

Traffic was tough out of Chicago. My attempt at beating the weekend rush was foiled by road construction and what seemed like the entire population of the city evacuating at the same time. I didn’t cross into Michigan until five o’clock. I pulled off to pick up a quick dinner at a drive thru shortly after the state line, and then settled in for the last two hour stretch to Brett’s parents’ place. As I drove, I again asked myself what exactly I was doing. The fact that I had agreed to be naked and probably have sex with someone I’d never actually met seemed almost impossible to me. And what kind of sex, exactly, was I willing to try? It was easy to imagine stuff in my head, it’s another thing entirely to do in the flesh, so to speak.

It was beginning to get dark as I pulled into the drive at the cottage. The lights from the windows cast a warm glow, and Kate’s car was parked out front. I my car next to hers and grabbed my duffle. As I walked up to the cottage, Brett and Kate opened the door. Brett’s arm was around Kate’s waist and they both had big smiles on their faces. Kate rushed forward and gave me a big hug while Brett took my bag into the cottage.

“I’m so glad you are here Ally! Was traffic bad? Do you need something to eat?”

“No. I grabbed a sandwich on the road. Chicago was a mess, but once I cleared that it was fine. Sorry I couldn’t get here for dinner. This cottage is so cute! Hey Brett. Good to MEET you in person,” I said smiling as I stepped in off the front porch.

Brett winced, but had a smile on his face. “Great to meet you too Ally.” He stepped forward an awkwardly hugged me. “I threw your bag in the spare room. It’s the second room down the hall. We are in the master. They both have en suite bathrooms. Feel free to settle in and then we’ll give you the grand tour.”

“Thanks. That’d be great. Let me just quick freshen up. I’ll be back in a sec.” As I walked down the hall, I glanced into the master bedroom as I passed by. On the floor next to the king sized bed was the Sybian, set up in all its glory on a plush towel. I immediately felt the familiar tingling of sexual arousal. I unpacked my bath kit, brushed my teeth and dabbed a bit of perfume behind my ears.

“Rum and diet sound good Ally?” Kate called down the hall. “It’s what we have open, but we can make just about anything. G&T? Wine?”

“Rum and diet is perfect, with a lime if you’ve got one,” I replied.

“Wouldn’t make them without on,” said Kate.

When I walked back into the main room, Brett handed me a huge glass. “It’s mostly ice,” he said, winking.

“Yeah, right,” I laughed. I could see why Kate was sold on him. He wasn’t George Clooney, but he had a playful air about him and when he looked at Kate there was a deep affection. Being hung like a horse was and added benefit.

Kate took my hand and we did a tour of the whole place. It was more a house than a cottage. It was clearly built for four seasons. Although the décor was rustic, there was a very nice, modern kitchen and dining nook. It had two more bedrooms downstairs in a walkout basement. There was an elevated deck with incredible views. I’d missed the sunset, but could imagine they were amazing. Below the deck was a patio and an in-ground hot tub with an insulated cover. The great room had czech porno what looked to be very comfortable over-stuffed furniture and a beautiful wood burning fireplace. We sat on the deck to watch the last sunlight fade.

“What a beautiful spot Brett,” I said. “I had no idea. When Kate said ‘cottage’, I was thinking, I don’t know, mice and bats and spiders. Coarse flannel blankets on bunk beds. That kind of thing.”

Brett threw back his head and laughed loudly. “Hardly! My mom isn’t the bat and spider type. Although the bedrooms downstairs did have bunk beds in the early days. My parents built this place about twenty-five years ago and then re-did the kitchens and bathrooms just recently. My siblings and I practically lived here with my mom during the summers growing up. Dad drove over from Detroit every weekend. I tell people ‘cottage’ because ‘summer home’ sounds a little too pretentious.”.

We sat for a while making small talk. Kate knew everything about both of us, so it was mostly Brett and I getting to know each other. Family. Jobs. Stuff like that. I knew that at some point in the evening we were going to embark on a sexual journey, but I couldn’t help keeping my emotional guard up. At some point, Brett mixed another round of drinks, and the alcohol was had the predictable relaxing effect. Finally, Kate broke the ice.

“It’s such a warm night. It must still be almost seventy degrees. Tomorrow is only supposed to hit fifty. Let’s head down and use the hot tub. It might be our only chance this weekend. We’ve had it warming since we got here.”

“I think that’s a great idea,” Brett said. “Ally, Kate and I will quick change. I’ll head down and take the cover off and turn on the lights. Kate can grab towels. Don’t forget to bring your drinks.”

As I headed to the bedroom to put on my suit, I knew without a doubt that this was the start. I felt a little bit like I was jumping into an abyss, but I felt at ease. I stripped naked and looked at myself in the mirror. My vagina was already dampening. “Here we go,” I said to myself. I pulled on my suit, grabbed my drink and headed downstairs to the patio.

Brett and Kate had beat me there and when I got to the hot tub it was clear, even with the bubbling water, that Kate, at least, was naked. Her bare breasts were only half-submerged. I could see that her right arm was across Brett’s lap and it was moving up and down. It was obvious that she was stroking him.

“A once piece? C’mon Ally. I think it’s time we get things going. Why don’t you lose the suit and join us?”

I initially hesitated, but I knew if I continued to stand there, it wasn’t going to be long before a moist spot would appear in the crotch of my suit. “Sorry. I guess I didn’t expect to go from zero to naked all at once.” I stepped into the tub and sat down. Brett and Kate were both watching me keenly as I pulled the top of my suit down and released my breasts. My nipples betrayed my current state of arousal. I pushed the suit down over my hips, took it off under the water and threw it up onto the patio.

“Good for you,” Kate said softly. “Why don’t you scoot over here by Brett and we’ll talk through some things.” I moved so that I was touching Brett’s right side. I tried not to look down at whatever was happening in his lap.

“Ally, do you want to talk about what’s in store here? What your goals are? What’s important to you?,” Kate asked.

“I guess so, sure. I mean, simply put, there are lot of things I haven’t tried. In the past it was because I didn’t think they interested me for a variety of reasons. Now I’m not so sure. Kate obviously told you about what happened, what we did when she came to visit, right?” Brett nodded. “Well, a lot of that I had never even considered. But I enjoyed it,” I said, starting to blush. “Seriously, look at me now. I’m sitting naked in a hot tub about to have a threesome, and I just met the guy. You have to admit there is something weird about that.”

“I don’t think it’s weird Ally,” said Brett. “I think it’s admirable. I completely understand that you may be nervous. I think that’s part of what makes exploring the boundaries so exciting. You never really know what you may find. And there is always ‘umbrella’ if what you find isn’t what you want. You can trust me, the safe word is an absolute pact.”

“Here’s the thing Ally,” said Kate. “Try to check your inhibitions at the door. This is an opportunity to find your inner whore in a safe situation.” At this point, Kate reached across and took my hand and placed it on Brett’s cock along with her own. She nodded slowly at me, and we both started to move our hands up and down his shaft. Brett closed his eyes and moaned quietly.

“Mmmmmmmm. Christ. That feels really good.” Brett’s cock was as stiff as a flagpole and truly huge. They say TV adds ten pounds, but if anything, he was even larger than he had looked in the videos. The plum sized head of his penis stuck out above both of our hands. I couldn’t close my hand completely around it. If Morgan at the toy store was right, and the average circumference of a man’s dick was five inches, Brett’s was easily six or more. After a few minutes, I glanced at Kate and tentatively moved my other hand to cup Brett’s balls. He was shaved of course, and I reveled in their silky smoothness. Brett began to pump his cock up into our hands, but then sat back.

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