Pushing Our Boundaries Ch. 01

This is a situation that took place a few years ago, a story about me and my then-fiancée Jane, about a time I never want to forget. I'm writing this to the best of recollection, and with the help of Jane's own thoughts and feelings regarding what happened which she was willing to share with me.

I'm going to be frank; Jane is drop-dead gorgeous and a picture of grace. There's something about the way it feels just being around her--it can be equal parts intimidating and welcoming at the same time. She has the most captivating emerald eyes and a picture-perfect smile to match. Beyond that, she sports a body that stands out in any outfit--and to be more specific--she's a 5'6" brunette, incredibly fit thanks to regular gym days, with an ass that gets most guys that pass by doing a double-take. To top it off, Jane knows she's attractive, but she's shy and modest about her natural beauty, and that makes me even prouder to be her fiancé.

We met innocently enough. My manager wanted to spruce up the office with some murals like a lot of other contemporary offices downtown, so we hired an up-and-coming art studio to do the job. As I was walking through the halls at work one day, I saw her talking to a coworker. That was the first time her ass got me. When she turned around suddenly and happened to look at me, time slowed down, and I spilled my coffee. I couldn't help it, her gaze felt like getting struck by lightning. And true to her kind nature, she rushed over to make sure I was okay and introduced herself.

The rest was history.

We went on a couple of dates afterwards, and when the studio finished their work on my office, Jane continued to stop by during lunch or after my shift so we could spend more time together. This was great, as I wasn't the brashest guy around, so I always hesitated before asking her out or initiating any type of communication.

We didn't have sex until much later, and I found out that she's a bit more inexperienced in that department, having only been with two guys before meeting me. This was amazing as we were both already around our 30's and you don't get out of college without messing around more than a few times. This was especially surprising as Jane, again, is an absolute stunner.

Anyways, as you can guess, the sex with her was well worth the wait. Jane didn't have many fancy moves, but her body and passion was mind-blowing. I have pretty good self-control, but she looks so damn sexy underneath me that one time early on, the lovemaking got so heated, and I broke out in a full-on nosebleed. I still finished. I had to. But that was messy.

Jane matched whatever request I had of her in bed, though we did keep it relatively tame. Like most couples we eventually stopped having sex every hour of every day, but it was still something I looked forward to whenever we were together. There's nothing quite like seeing her toned ass as it comes down on my cock again and again--it's honestly so mesmerizing. I've caught myself more than a few times just daydreaming about her body. We would later start defaulting to missionary and reverse cowgirl during lovemaking, but it was still the case that no one in my past relationships has ever compared to sex with Jane.

This, coupled with the fact that everything always feels so right when I'm with her, meant that about a year on into our relationship, I had no choice but to get down on one knee and propose. This made Jane my fiancée, and me, a very lucky man.

Now that you're all caught up, we can move forward to one fateful day, and learn a bit more about my hidden fetish that changed our relationship forever.

---

I woke up a little groggy that day.

When I stretched out and glanced at my phone on the bedside table, it looked to be closer to lunch time, and I remembered that Jane had the car. She wanted to drop off a few things at her studio in the morning before coming back to get me and have a late lunch with some of our mutual friends.

However, as usual, it felt like I was rock hard down there this afternoon. I figured I had a good half hour, so I decided to get to work on my "afternoon" wood, using my phone's incognito browser so I wouldn't have to get up and grab my laptop. Something remarkable about porn nowadays is that you can access it everywhere, on anything! Not that you'd always want to, but it's still mind-boggling and super convenient.

Technology.

After a bit of a hasty finish, I see a message pop up on the screen from Jane saying she's about 5 minutes away. No problem. I throw on something decent and make my way to the front door. The lunch isn't a special event, just a quick hangout so I didn't need to wear anything special.

When I receive another message from Jane, I head out to be greeted by her lovely smiling face from inside the car. She hops out, and I hop into the driver's seat, but not before exchanging a peck as she heads on over to the passenger side. I always stop and take note of her sexy sway; that's never going to get old.

We talk a little bit about what to expect as we pull out of the driveway. Jessie and Reiner have been my friends since high school that ended up getting married after graduation, and I had already introduced them to Jane -- who they got along with swimmingly. We assumed there was going to be more discussions about our own wedding which was fast approaching. Tammy, Jane's best friend since elementary, would also be there. We always prepared ourselves when Tammy would be around, as we all knew it was going to require a bit more energy to match hers.

While we're discussing this, I realize we've been listening to a dull sports commentary on the radio.

"Hey babe" I asked, raising an eyebrow. "What is this station?"

"Oh, I thought you'd want to listen to one of those basketball shows in the background."

"What? That's really sweet!" I really did think this was incredibly thoughtful of her, but I knew for a fact she hated listening to sports radio hosts talk about the game the night before, though more importantly, I hadn't had a chance to catch a highlight yet because I went straight to bed after yesterday's shift. "You can change it to your music though, let's listen to something fun instead?"

This was immediately greeted by a nice peck on the cheek. I was the man. Honestly, sometimes with Jane, it felt like I could do no wrong.

Except, I wasn't perfect. Far from it.

As I came off the highway exit that would bring us five minutes from the restaurant, I hear the radio station stop abruptly as Jane changes the car's audio input. I should have anticipated what was about to go wrong as she selected the option for "Bluetooth".

The car radio immediately connected to the phone.

My phone.

Apparently, the car's Bluetooth picks up whichever phone was last connected. Otherwise, you would need to manually switch the phone it connects to--after the fact. Another fact I learned that day was that if you had a video playing and didn't close it, that's no problem at all for your helpful car Bluetooth, which just continues playing the audio for you right where you left off.

All I hear as I'm driving along is the abrupt and breathy moaning I recognize from about an hour ago and then in an urgent tone: "Yes, fill me up, baby!"

An equally breathy male: "Are you sure this is what you want?"

"Yeah... and that's what my husband wants too!"

At that point, I swerved. A loud honk erupted from the car beside us and I steered back to safety and away from danger. I was only able to briefly turn my head to see my fiancée's astonished face as the conversation coming through the radio devolved back into loud, incoherent moaning which would crescendo with the male porn star's impressive roar as he (presumably) filled her up.

When I had managed to steady the car, Jane and I both didn't say anything. I just hit the mute button on the steering wheel--which I had somehow neglected to do a few seconds ago--and drove the car in complete silence. I just assumed she still had the shocked look on her face the rest of the way to the restaurant.

When we finally pulled into the parking lot, Jane still hadn't said anything. I turned to finally look at her, and she was just staring stone-faced at the dashboard.

I followed her eyes and noticed that the title of the video I had been watching before she came to pick me up was still being beamed to the head's-up display. There it was, in plain sight for my innocent fiancée to see: "Cuckold shares wife for the first time". I hit the engine button as I saw this, embarrassed at everything that had just transpired.

A million thoughts were running through my head. The most prominent of these thoughts was: is she going to break up with me now that she knows I'm an absolute pervert? Then there was: is she going to break up with me because I now clearly watch porn when she's not around? Is the wedding still on? Why the fuck did I not close the incognito browser when I was done? Why does my car's Bluetooth not prompt to ask which freaking phone it wants to connect to?

These questions flashed like a dingy motel's flickering light bulb in my head, too fast for me to rationalize any answers.

I think at some point I just gave up and put my head in my hands. I was equal parts mortified, embarrassed, and tongue-tied. Done in by the same technology I had been praising when I woke up. "You can access porn anywhere!" Ugh. Dumbass.

It was Jane that finally broke the silence. I glanced over at her as her signature calming voice broke through my self-loathing.

"So, what's a cuckold?"

I blinked at her. She didn't look angry at the moment. In fact, it looked like she was smiling just a little. Maybe life wasn't truly over?

"And why is he sharing his wife!?" As she asked this question, my amazing fiancée broke out into laughter, and I did too. It was such a relief. Jane had reacted in the best way possible, and I couldn't believe it.

"Do you really want to know?" I asked, lifting my head.

"Well, I expect you to tell me... later." She opened the car door as she said this, gracefully exiting as I clumsily followed out of mine. "Right now, we're here to meet our friends!"

She turned and waved at our friends who were visible through the restaurant window, seated inside, and they waved back. Looks like there was time for this discussion later. I reached for her hand, and she for mine, as we both hurried inside.

Before we managed to get in, she gave me another kiss on the cheek, and said "I watch some porn when you're not around too."

I nearly tripped right into the glass doors.

---

When we got back home, I took a deep breath and readied myself on our living room couch. I had a feeling this might be the most awkward talk we've ever had. Everything always seemed to click with me and Jane, but her obvious confusion regarding what a "cuckold" even was, meant that I had some ground to cover. She took some time to pour us some water before sitting down, an adorable look of curiosity plastered all over her face.

"So, spill it, mister!" She said, handing me a glass.

"Okay, Okay." I said, taking a sip. "I watched a bit of porn before you got home."

"You know what I'm really asking for!" She said, shooting me an annoyed glare.

I smiled awkwardly as I placed my glass down on the coffee table. "Alright, "cuckold" ... well, it's usually a guy who..."

I struggled at this point, realizing I never really had to explain the term to anyone else before. "It's someone who likes watching his wife do... sexual things with someone else."

Her eyebrows shot up fast.

"Wow. Really? Are you sure it's not like... a fake category?"

"What do you mean?"

She also set her drink down at this point before responding, "I mean, I think it's most pleasurable having sex yourself. Especially with your partner! Right? It's pretty obvious that it can't be more pleasurable watching someone else have sex with your wife. How could that even compare?"

I squirmed uncomfortably, trying to look her in the eye while admitting probably one of the weirdest fetishes I had. "Well... I actually find it hot. And I think a lot of guys do too. I mean, that's why there's a whole category dedicated to it, right? And it's huge! You can even look up hotwife--"

I had to stop myself at this point. I didn't know how much she wanted to know, or how much I should be talking about this in the first place.

"Hotwife?" She tilted her head as she heard the word. "Oh, that's what the wife of a cuckold is called in this scenario?"

I nodded before closing my eyes and breathing out. "You got it! And now that we're done with that--"

As I stood to signal the end of the conversation (at least for me) Jane pushed me gently with her hands, signaling to me that this was not, in fact, the end of the conversation.

She was quiet for a moment before asking, "Are you a cuckold?"

"What?" I probably looked surprised. I mean, I really was. At the fact that she asked me that question, and as some odd ideas flooded like a raging river into my head. "No. I think I just like watching that type of porn."

"Let me rephrase. Would you like to see me with another guy?"

At this point, I just couldn't find the right words. I was just sitting there, staring at the most beautiful woman I've ever been with, her eyes looking straight into mine, trying to get me to spill the beans on what I consider to be my most perverted interest. I just sat there, unable to speak. That was twice today.

Jane began to lean over at this point.

"You do, don't you?" She brushed away a lock of soft hair from her face as she crept closer. "Even if you don't want to tell me the truth, this little guy seems to be feeling pretty honest."

She placed a finger on the tip of my cock which was threatening to burst through my jeans, and added, "As usual."

I shrinked away just a little. I had no idea I was getting turned on by her line of questioning. I also couldn't tell if she was just making fun of me, or if this was something else altogether. I was honestly just absolutely confused at the situation. Jane hadn't done anything like this before. This was not the same timid fiancée I had proposed to.

Slowly, she unbuttoned my pants, and pulled at my boxers. My dick sprung up in front of her face, and I was suddenly staring down at one of the hottest sights in the world as my fiancée reflexively bit her lip, behind my swollen cock.

Before I could say anything else, she gave the tip a playful lick--sending shivers up my spine. This was unbelievable. Shouldn't she be angry? Or disgusted at what I've just told her?

"Do you want to see me licking someone else then? Just. Like--" Jane licked again, this time from my balls to the tip. "--this?"

I had to grip the couch. This was hot. And I've never gotten this hard from just one lick and some gentle teasing.

Jane opened her mouth now, as if to take me into in her mouth, before quickly raising my boxers and backing off. A mischievous smile flashed on her face.

"Well, thanks for answering all my questions!" She gave the outline of my dick a gentle pat before sitting up and beginning to walk away.

"Hey!" I sprang up immediately, catching her by the waist. "You can't leave me like this?"

I'm pointing at my rigid boner. Something of note: I wasn't too shabby, girthy at about 5.5 inches. I've never heard any complaints. To be honest, the main issue right now was that it was so hard it hurt. Jane was usually a little more subdued when it came to sex and often took my lead, so seeing her take control and try to work me up took my lust to another level altogether.

"Oh, would you look at that!" She bent over just a little, planting a kiss right at the tip where my precum was creating a spot on my boxers. "Looks like you really enjoyed the show!"

I couldn't take it anymore. I wanted her. Now. I reached out and lifted Jane up before dropping her right onto the couch. Almost as if she had anticipated it, she giggled a little, biting her lip and lifting her gorgeous legs up to the ceiling.

"Fuck."

I wasted no time pulling her skirt and panties off, all the while kissing her pretty toes and legs. When I split her legs apart, she was looking right at me with the sexiest smirk I've ever seen. I aimed my cock at her beautiful, shaved pussy and slid in with no problem -- I don't know if she's ever been this wet. I truly fucked her harder than we've ever fucked before.

Her wild moans fueled the fire, and for the first time I could feel her digging her nails into my back, and wrapping her legs around my ass, as if begging me to go even harder. This was unreal. When I felt like I was getting close, I lowered my head to whisper into her ear. "Looks like I'm not the only one who likes the idea."

I felt her grip me harder and heard "shit" escape her lips as her pussy tightened around my rigid cock. Jane was cumming--hard--and I followed suite just a few seconds after. It felt like I was pumping a gallon inside her.

For a long while, we just lay there, gasping for air and holding each other on the couch. We weren't fully undressed so everything we were wearing was soaked with sweat. I don't know that either of us had come that fast before. At that moment, we didn't care for anything but fucking the living daylights out of each other.

"Well, that was something else." She said, looking up at me smiling with my arm draped over her shoulder.

We both just erupted in laughter.

---

"Is it here?" Jane asked, consulting the map on her iPhone as we slowly drove down the rural road.

"I don't know, you have the GPS!" I chuckled as I said this, more amused that anything else because Jane refused to use the voice option on her phone that would narrate the route to us. She instead insisted that she guide us the whole way through.

"Whatever. Turn here." Jane was zooming in and out of a particular portion of her map, clearly frustrated. "I won't let this sultry Australian voice on my phone replace me. No way. Only my voice for you."

I pulled into a small road framed by a canopy of large trees, their branches letting in only slivers of sunlight to light up our path. It was kind of gorgeous to see, pretty picturesque. Jane was already on it, switching to camera mode, documenting the path ahead.

"Uh, what about the map? Do you know where we go from here?"

"Relax, babe." She didn't look up from her phone. "It's just a few more minutes, straight ahead."

After lunch with our friends, Jessie, Reiner, Tammy, and her new boyfriend Paul who she had brought along, we had all decided on a summer weekend Airbnb getaway outside the city. I was personally all for the idea, as Jane and I had been starting the feel run down by work, and really needed some rest and fresh inspiration. Now--a month later--we'd finally be getting our wish.

But there was something still bugging me. Another topic we had shelved that had come up right around the time we were planning this mini vacation.

"Oh, babe?"

"Yeah?" Jane put away her phone now, opting instead to hold my free hand.

I hesitated. "About the thing we talked about... the "cuckold" porn?"

She paused too, before answering. "What about it?"

"We haven't talked about it since. I mean, not really. We just kind of had sex."

"Really good sex!"

"Yeah, really good sex!" I shifted a little in my seat, trying to get a little more comfortable. "What did you think? I've never seen you like that before."

Again, she stayed quiet for a while before responding. I assume she was a bit embarrassed. "I... wanted to see if I could turn you on. I mean when I watch porn... I usually only see very confident women. They own their sexuality. I feel like that's what makes it hot."

"Oh. Yeah, I guess so." I struggled to find the words after again being reminded that my classy fiancée actually watches porn. "You just kind of ooze sexiness though. You don't really have to act a certain way to turn me on. You're fucking hot. Period."