Zack and Emily Ch. 01

Note: This is a new story that will incorporate a good amount of things from my other stories for these new characters. I will start off with more of an introductory story here then have subsequent chapters be about the adventures of these new characters, each one about a different kink one of them has in a different category or something like that. I will hopefully get back to other stories soon for those of you that care, but had this one bouncing around my head for a bit. I hope some of you enjoy reading my stuff as much as I do writing it. I have never written anything in my life outside of school except for this site and apologize if my stories are redundant and not perfectly written. I just use this as an outlet. With that said I hope you enjoy!

My name is Zack. I am thirty three years old and single. I don't have any kids as I realized from a young age that I very much dislike them and didn't always want them around. I also don't want to commit my life to raising them and want to do so many other things. I haven't dated a ton, but had girlfriends back in high school and college. After college the only sex I have had was with a longtime friend that turned into a friends with benefits situation after a drunken night. Because I had known her a long time I knew she wanted marriage, kids, and that whole deal and was very up front that I did not and would never change my mind. If she was ok with that then adding sex in could work for as long as we wanted it to. She said yes at that time as she was single, wanted sex, and felt comfortable with me.

From the get we said it would be purely sexual and either of us could date if they wanted. She actually did here and there for most of it, but never found someone she wanted to go further with. We agreed if either one of us found something they really wanted to pursue with someone else we'd end our thing and would be happy for the other, and would never let it affect our long term friendship. We promised to each other that when it ended we would go back to being friends with that very enjoyable part of our lives to always remember.

Our friends thought we were naïve and that it wouldn't work, that we would ruin our friendship and make things awkward in the larger group. We had amazing sex and it was great. We explored all kinds of things and helped each other learn what we really liked. Like all good things though, it had to come to an end. After about a year I told her it's probably best for us to stop and that it wasn't because I wasn't enjoying our time together. It was because I didn't want her changing for me and felt like I was holding her back and providing a safety net. I wanted her to have everything she wanted in life and could not give it to her.

She was sad at first, but realized it was for the best. Not only did we never have issues and make anything awkward for our friend group, but we also stayed friends after it ended and proved all of our other friends wrong. Over time we grew apart naturally as she moved away to another state, but we still keep in contact here and there to this day. I still consider her a very close friend and am happy she found a guy that treats her right. I honestly believe we helped each other in a lot of ways and I am glad we had that experience.

That ended about five years ago and I haven't dated or had sex since. I was never one to need someone around and wasn't the kind of guy that had the sole mission of getting laid. I am generally a homebody and like to be alone most of the time, but at the same time I do enjoy traveling to different countries. Watching porn is enough for me. I watch a ton of it and am pretty much addicted to it. It's the first thing I look at when I wake up, something I think about often during the day, and I very much enjoy long masturbation sessions with a fleshlight where I edge for hours. I do this probably a couple of times per week.

I think what helps keep me pretty horny all the time is that not long ago I discovered a company that sells crotchless boxer briefs. They have a hole in front that my dick and balls fit through perfectly, providing a little snugness around the base so I always know that I am hanging out of them. Other than that they are just regular boxer briefs. I go commando a good amount as well, but sometimes worry about things like someone noticing or my pants ripping in public. These crotchless boxer briefs allow me to enjoy the feeling of my dick against the inside of my pants while out and about, while at the same time showing that I have underwear on to anyone who happens to see.

I'm either wearing the crotchless briefs or nothing at all. Because of this my dick is always visible and touchable when lounging around at home, where I am most of the time. I also love using butt plugs and have been experimenting with longer term use so I have one in a lot of the time. I've been using them on and off for many years and am now using them a lot more. Having a plug in my ass and my dick hanging out of my boxers so often keeps me horny quite a bit.

Not long ago I got the idea to try out a popular dating app to see what was out there. I don't need sex, but it had been a while and I do enjoy it. If I didn't find anyone then no biggie and I could go back to what I knew I enjoyed. After a few matches and messages that led nowhere I gave up. I edited my profile to say if anyone should see it I think the app is probably a lot of fake users or robots trying to get me to pay money and that I was done with it. If anyone was interested in meeting I would be at this certain dive bar the next four Thursday nights and giving the final date.

On top of listing non-sex interests of mine (travel but mainly a homebody, watching sports, movies/TV shows, techy stuff) I said I am pretty kinky and not just looking for sex, but rather a girl that is very open, has no hang ups with sex, doesn't judge, and wants to explore things together. I added that I wanted to be honest from the start and am hoping to find someone that doesn't want a traditional relationship where sex is just part of it, and more and more over time it is not, but rather someone who wants to base a relationship around it being at the forefront and wants to find out everything about themselves. I also mentioned that I have no kids and don't want them. If someone came to meet me I knew we would have a lot of potential wasted time out of the way.

Even though I was done with the app I kept it active by liking a few profiles here and there so mine would hopefully remain viewable to others. I even begrudgingly paid for something that said it would give my profile more views and made sure it was one-time only and wouldn't continue past that one payment.

The first Thursday comes and I head to the bar. I sit down and order, chatting with the bartender and others around. I have a good time and leave with no one coming up to me. The same goes for the second Thursday. On the third Thursday I am talking to the bartender and ready to call it a night when one of the most attractive women I have ever seen walks in. She is tall, maybe close to six feet (I am 6'4), has straight blonde hair in a ponytail, perfectly tanned skin, tits on the smaller side, which I prefer, light features, and an overall thin frame. She has a stereotypical all-American girl next door look going on. She is wearing a white sundress with green flowers on it that goes to the middle of her thighs and a pair of Chuck Taylors with no socks -- a kink I didn't know I had until that point. She sits at the bar a couple seats down from me. The bartender asks her what she will have and she replies nicely that she needs a minute.

She buries her head in her phone and when the bartender approaches her again she says she is sorry, but actually has to go. She gets up and leaves. I am sad that she wasn't there for me as she was so beautiful. The bartender and I share a glance that tells the other we thought she was hot. I am about to close my tab and leave when the same girl walks back in and sits right next to me. I am kind of in shock and am pretty sure she saw my profile.

I look over at her and we share eye contact and a smile. She has the nicest green eyes, another thing that I love. After our shared glance she looks back to her phone. I decide to say nothing. If she wants to talk to me she will when she's ready. After what seems like hours, when it was probably not even two minutes, I am looking at my phone when I hear "I liked your dating profile." I want to jump up and throw my fist into the air in celebration, but instead use every fiber of my being to remain calm and normal.

"Yeah?"

"Yeah. I also think apps are pretty much a scam. All I get is weirdos or matches that either never send me a message or don't reply when I do. I mean, to match that means they liked what they saw right? Why would they not message me or reply when I message them?"

"Right," I exclaim in a questioning manner.

"It was refreshing to see someone say what you did and be completely honest like that."

"Zack," I say while extending my hand out with a smile.

She shakes it. "Emily."

"It's very nice to meet you, Emily. I am glad you saw my profile and that you decided to come."

"When I first came in I was so nervous and backed out. I got back to my car and thought to myself why not take a chance? What do you have to lose? It's not really different than if we had matched and decided to meet. If nothing happens then nothing happens. So here I am."

"Here you are. What can I get you to drink?"

"Honestly, a nice cold beer sounds great right now. It's so hot out." Wow, she's hot as hell and likes beer. Good start.

I catch the bartender's attention and he walks over to us. "My friend Emily here will have..."

"A Jai Alai sounds good," she says. The bartender looks at me with an approving nod.

"Two Jai Alais, please."

"Coming right up."

As he goes to grab our beers I tell her I was impressed with the drink selection.

"I've never been a fancy drink girl. I grew up with two brothers and watched a lot of sports. Beers were always around."

Right after we get them and take our first sip I speak up. "Is it ok if we skip the whole what do you do for work, where did you go to school, talk about your family thing?"

"Oh my god, yes please. I'm so sick of that stuff."

"I figure if we hang out and talk more that stuff will come up naturally anyways. I want to know about you and your wants. I haven't been on any kind of meet up or date in many years as I mainly had long term things and it's been a while for even that so I don't have any game at all."

"I don't want game," she replies. "I just want to talk to someone that, from the limited amount I know of them, I find interesting and would like to know more about."

"Well, look at us. Who woulda thought?"

"Please tell me that was a Paul Rudd reference," she says with a smile. I cannot believe she got what I was going for. Hot, drinking a beer in a dive bar, knows movie quotes. This couldn't have got off to a better start and I am going to try my best to not fuck it up.

"It was. It's awesome that you got it."

"Well, he's awesome and I'm a big movie quote person. Probably a little too much."

"You're kidding, right?"

"No. I love movies and quoting them. My friends tell me it can get annoying, but whatever."

"Well, I do not find it annoying. Quite the opposite actually. I am also very big into movies, as you might have seen in my profile, and quoting them." She smiles and takes another sip of her beer.

I decide to go for it. "Since you're here I'm guessing you are into what I wrote about in my profile?"

"Yes," she replies as she quickly looks at me then back to her glass, seemingly a little nervous.

I wait, wanting to know what she will say next. I hope she is comfortable enough to speak up without being asked a question.

"I can't believe I'm going to be this direct with someone I met just a few minutes ago, but fuck it. I'm here, we both know why, and we're both adults so let's not beat around the bush."

"I completely agree."

"I've dated and had all kinds of experiences, but each ended in disappointment. I saw your profile and liked it, but since I didn't get a match I figured you weren't lying about being done with it and my only chance would be to come here if I did want to meet you and see if there was something."

"Yeah, I haven't opened it much since I wrote that other than to like a random profile here and there to keep mine active. I would have definitely liked yours if I came across it. If no one came by next week I would be done with this little experiment and would go back to not trying much. I am done with any kind of apps."

"I was honestly a little taken aback by what you wrote. It said a lot of what I want for my life. Worst case you wouldn't be here and all that was wasted was a little time. I am also sick of the apps and thought if this were real that maybe it could be something and I wouldn't have to use them anymore."

"I'm hoping for that too." She smiles and takes another sip of beer. "I would love for us to have an honest conversation about what we want without fear of being judged and without the whole interview-y date thing where the real stuff is held back."

"I want that too. I really can't believe this is happening -- meeting someone like you that is so up front. It's weird, but my nerves are almost gone already and I feel very comfortable around you."

"I am happy to hear that. I also feel very comfortable too. I thought I'd be nervous the whole time. I was a little at first as you are so beautiful and I couldn't believe that you wanted to meet me, but that has all gone away."

"I am very glad to hear that as well, and thank you for the compliment. You aren't so bad yourself." She takes another sip of her beer and it looks like she is thinking about what to say next. "When you said that you're kinky and want to explore, what kinds of things were you talking about?"

"So you want to get right to that, huh," I ask with a smile.

"Yes."

"Let's do it. I have no problem talking about sex and wish more people weren't so afraid to."

"Part of why I don't go on a ton of dates, or why things don't work out when I do, is that I sometimes feel shame about my wants and I don't want to be judged for them. It's easier to walk away or not try than risk being embarrassed. I don't want that anymore. I want to be completely myself from now on."

"Please do. There's not a single thing you can tell me that I will judge you for. Everyone has their stuff. I have mine and from what it sounds like you won't judge me either."

"I would never. I consider myself a very open-minded person. I support whatever people want to do to get enjoyment as long as everyone involved is on the same page. Communication is very important."

"I feel the same way. I am looking for a girl that I can go up to and say I would like to try a certain thing I find hot and for them to not to just be open to discussing it, and maybe doing if comfortable with it, but to also be happy that I felt comfortable enough to share with them. At the same time I want to be that for her -- someone she can open up to about anything she wants and needs, about sex or anything else at all, and to feel completely comfortable doing so. There is almost nothing I won't do sexually or otherwise for my partner. If there's something she wants to do or try I will be completely supportive and give it all I have. I want her to feel zero shame in letting me know what she likes and for it to be normal to suggest even the craziest things. Seeing a girl turned on is one of the sexiest things to me." I hesitate for a second before I complete my thought. It's a risk, but I hope it works out. "Only seeing her cum tops it."

Emily quickly turns her head and meets my eyes. "Damn, that was so hot."

"At the same time I don't want a girl that just says yes to everything I ask for to do it for me. I want her to get enjoyment out of it too, and if she doesn't, to be honest and communicate that. If there is something she doesn't want to do I want her to feel comfortable enough to say so. I don't want anything going unsaid and for that kind of stuff to eat away at the relationship."

"I feel the same. There's not much that I haven't done or wouldn't be open to." The longer this goes the more I wonder if this is some kind of prank or sick joke. I mean, how is a girl that looks like her, and is so sexually open, not with anyone? She just admitted that she is down for pretty much anything sexually. I have so many images of her in various situations going through my head.

"I have a confession," she says. I look at her. "I wasn't sure I would be telling you this, but I think we're off to a good start and to be honest this conversation is making me a little horny. Plus I am not ashamed of it as it's something I enjoy."

"Please go on."

"I have a butt plug in right now."

I am overwhelmed with excitement and horniness right after she tells me. I honestly cannot believe it as I have one in too. I lean in close to her ear. "You're not going to believe this, but so do I." I pull back and we look into each other's eyes.

"Are you serious?"

"Yes." I tell her all about how I got into them and that I have been experimenting with wearing them for longer periods. I also let her know that I want to continue to do so hopefully to the point where I have one in most of the time as it makes me feel good.

"Wow. I'm not at that level, but I do enjoy the feeling and having that secret when out with family or friends. No one knows I wear them except my closest girlfriend Zoey, and you now. I like that you enjoy them too, and that you're willing to tell me after just meeting me."

"How often do you use one," I ask. "And why tonight?"

"I don't know, maybe a couple of hours or less a couple times per week. Sometimes more, sometimes less and a good amount of the time when masturbating. I wanted to feel a little dirty and have a secret tonight to be honest."

"Secret's out!" She laughs and takes a sip of her beer. "Do you enjoy anal sex or just the feeling of toys?"

"Both. I haven't done it with guys a lot, but when I do, and it's done right, I really enjoy it. I find myself using plugs and dildos more and more when alone lately. I even have one with a tail that I got recently. I find it to be fun."

"Oh man, I love those. I kind of wish you had it in right now."

"Me too, but I might get some weird looks with this dress not being long enough to cover it," she says with a little laugh. "I did go out with it once, though. I was wearing a long dress with nothing underneath and did my grocery shopping. It got me so horny that I masturbated in my car as soon as I got back to it."

"Wow."

"Do you use plugs just for the sensation or do you like anal stuff?"

"Both. I like the feeling of them, but I also enjoy fingers, dildos, whatever else in my ass sometimes too. It just feels good."

"I'm glad that you are not ashamed to admit that. I think most guys are."

"It seems that more and more it's becoming acceptable for a guy to admit hey, this feels good, and get over the whole stigma of it being about who you are sexually attracted to. It's a body part that can make you feel good if you know how to do it just like any other."

"Well put."

"How did the last guy, or any guy, you were with fuck things up with a girl that is so cool and open, is so honest, is as stunningly beautiful as you, and is kinky?"

"Awww thanks, but those are stories for another time. A couple cheated and some ended naturally or for other reasons."

"Idiots."

"Yeah, it's odd to offer someone pretty much whatever they want and for it to still not be enough."

"I'm sorry you had to go through that. I have never been cheated on, or cheated myself, so I can only imagine how hard that was and hope you never have to experience it again."