Healthier Habits

I was half way through my daily grind at work's gym, when Jen walked in.

For the last few months, Jen and I had been gym buddies, an arrangement that worked well for both of us. Jen had always struggled sticking to a regular routine, her various vices always too big a temptation when it came time to make a choice. I, however, generally found that, once I decided to get back in shape, I did it. Regardless of how much it loathed me to slug it out on the human hamster wheels.

Lately, Jen had been falling off the exercise wagon, more so than not, so her progress had become a veritable roller coaster. Personally, I always thought she looked pretty good. Admittedly, Jen was a little curvier than I usually liked, but I still loved the way her ass looked.

As usual, Jen climbed onto the treadmill next to mine, and started her brisk walk.

'Ouch. That hurts a bit,' she winced, after a few minutes.

'What does?'

'Breathing,' she chuckled.

'You still trying to quit smoking?' I asked casually, knowing it had been a source of frustration in the past.

'Yep, and these little sessions remind me why. Don't suppose this pain in my chest is related do you?' Jen asked, sarcastically.

'Nah,' I replied, matching her tone.

'You know it would be so much easier to quit if I had a boyfriend,' Jen whined.

'You think?' I retorted.

'Oh yeah. It's that whole thing of having something to replace cigarettes with,' she said.

'What do you mean?' I asked a little confused.

'You know, the whole "oral fixation" thing. If I have a boyfriend, I just "smoke" something else,' Jen explained, a devil's smile flashing across her face.

'I see,' I responded, pretending to ponder the notion deeply, as the visual momentarily corrupted my senses.

Neither of us spoke for a few minutes, then Jen broke stride.

'Ah. That's not good,' she stated, cringing.

'Hey, if it hurts, stop,' I cautioned.

Having hit the stop button, Jen climbed down.

'You right?' I asked.

'I just felt a sharp pain shoot up my thigh, through my...."

She paused.

"Well...through my gee-gee.' she hesitantly concluded, rubbing her waist.

I watched as Jen lay down and began stretching as if she were going through the Kama-sutra. I felt like I should have been tossing dollar bills.

It was not long before Jen's display ended, her mobility returning. Reaching forward to touch her toes, she laughed.

'Aww. I used to be able to touch my toes,' Jen groaned.

'Well, welcome to thirty-something,' she said, prying herself up dejectedly.

'You know, I never used to have trouble keeping my weight off. Guess that's another upside to having a boyfriend...a sex-life,' she mused.

An instant later, Jen's eyes lit up.

'Hey, I have an idea. You don't have a girlfriend, right?' she asked pointedly.

Jen knew I had gone through a difficult break up a few months back, so the question was more rhetorical than anything.

'No, you know...wait a minute. Why?' I asked, suspiciously.

Sensing my trepidation, Jen held up her hands.

'Hear me out. You're always complaining about how this is so boring, right?'

I nodded slowly.

'Why don't we add a little something, to our daily routine? To make it more appealing,' she finished, barely able to contain her excitement.

I began to fidget, as the gist of Jen's suggestion found its mark.

'Now, don't freak. I'm not suggesting we date, or anything. I just thought we might both benefit from a little more excitement,' she rationalized.

As if perplexed, she paused before exclaiming triumphantly, 'We'd be fitness fuck buddies! FFB's!'

My mind was yelling that this was probably not a bright move, when it was interrupted.

'And maybe you might be able to help me quit smoking?' Jen added, letting her words hang.

'You mean...' I started.

'Ah huh,' Jen replied, nodding knowingly.

Just as I was about to open my mouth, Jen added, 'Do you know how many cigarettes I smoke a day?'

Switching off the machine, I climbed off and sat down. Hanging my head for a moment, I looked up.

'So how would this work exactly?' I asked, surrendering to my own pent up frustrations.

With a delighted "Yes" Jen proceeded to lay out the plan.

We knew a few rooms with no windows, and with locks on the doors, where we could "work out" after our usual routine. As for Jen's quit campaign, she generally smoked at lunch and after her work out. Jen also proposed that each of us should have a pack of condoms handy, or "going Dutch" as she put it.

With the general idea now fleshed out, so as to speak, I helped Jen up.

'So, I guess I'll see you tomorrow,' I said, a little sheepishly.

'I guess. But, you know, I really feel like a cigarette,' Jen said, grinning slyly.

'But I'm a bit...you know, gross,' I responded, feeling my every pore dripping sweat.

'You couldn't taste worse than a cigarette,' Jen said, honestly.

A nervous glance at the door prompted Jen to suggest her office, assuring me we would be alone and that her door had a sturdy lock. Before I could reply, she grabbed me by my gym bag, and led the way.

As promised, Jen's department was a ghost town. Pulling me into her office, Jen made a show of flipping the door's latch, before turning to face me.

'Now, would you like to stand or sit? I'm easy either way,' Jen said, as she threw our bags aside.

'I think I'd prefer to stand,' I replied, my voice betraying my nervousness.

'Well, okay then,' she agreed, more than a little self-assuredly.

Jen gently pushed me against the wall, and fell to her knees. I closed my eyes as I felt her fingers slip inside my waistband. Jen paused ceremoniously, before slowly pulling my shorts down.

Now, I know I'm not big. In fact, I am "the average Joe" in the joy department, and quite comfortable with that fact, but I've always dreaded that moment when my best friend makes his first appearance in front of a new audience.

Thankfully, Jen set any fears I harbored to rest with a reassuring wink and smile. I felt thankful to already be hard as Jen's hand delicately stroked my shaft, while her tongue lightly traced circles around its head.

Without warning, Jen engulfed my entire length in one smooth motion, as she gave my balls a light tug. Her lips formed an exquisitely tight seal as, over and over, her mouth groped my pole.

I soon abandoned any effort to remain silent, surrendering with a low groan as Jen's head continued to bob and twist.

Feeling the familiar sensation of an orgasm brewing, I gasped, 'Jen. Jen, I 'm going to cum.'

She didn't react.

Unsure whether or not Jen heard me, I repeated my warning.

A moment later, Jen responded by firmly pressing a finger against my perineum, and massaging it vigorously. I couldn't take it anymore. My knees buckled a little as I came hard.

Lost in my orgasm, I slipped my hand into Jen's hair, and buried my erection deep in her mouth, as what felt like a river flowed forth. Regaining some composure, I mentally froze; a wave of fear hitting me, as I recalled my heavy handed impulse.

My concerns quickly subsided; as Jen sat back smiling up at me.

'Wow. That was just what I needed,' she said contently.

As Jen rose, she gave my shaft a little squeeze.

'You know, you don't taste half bad. Not salty...not anything really...which is good,' she concluded.

'I'm sorry. I tried to warn you,' I started.

'And I heard you,' Jen interrupted. 'I just thought I should taste you once, before making any decisions.'

'Guess I can still be a nice girl,' she added, sounding entirely too innocent.

And so began our arrangement.

Next day, we had lunch with our regular gang. As the check arrived, I felt Jen lightly nudge me under the table.

'Well, I need to go to the bank. Does anyone need to go?' Jen asked no one in particular.

'Yeah, I'll come.' I replied, trying to remain nonchalant, as I watched Jen stifle a giggle.

We soon found ourselves parked in a secluded back lot.

'I've been fighting a craving all morning. May I?' she asked politely, batting her eyes.

Not a minute later, my seat was fully reclined, and Jen was feverishly working her lips around my little guy. We both moaned with abandon, as she determinedly applied her skills. Feeling Jen's fingers adamantly trying to wriggle between my thighs, I wholly consented to her advance, parting them generously.

Jen's finger again quickly zeroed in on my perineum, causing an involuntarily thrust of my hips. I flinched as Jen's finger slipped lower and pressed firmly against my anus. I found myself instinctively spreading my legs wider, as the intense stirrings of an orgasm grew.

Jen paused and, looking up, slowly licked a finger.

'Oh, that's so hot,' I breathed, as Jen reached back down, and gently drove her digit into my rectum.

I exploded.

Without a sound, Jen's head continued bobbing, as her lips milked me dry. I felt her finger wiggling in my ass, as she looked up, grinning criminally.

'I think I've found something you like,' Jen chimed playfully, sitting back up.

All I could think was "What just happened?"

As I pulled my clothes, and myself, together, Jen drove us back to the office.

'So, I'll see you at six?' Jen asked, removing her keys from the car's ignition.

'Ah. Yeah, six,' I replied, hoarsely.

The rest of the day flew by, so much so that when I checked my watch, I realized I was five minutes late for our workout. Grabbing my bag, I bolted for the change rooms. Entering the gym, my heart sank. Jen was nowhere to be seen. Shrugging, I laid my bag against the wall and climbed up on the treadmill.

Not a moment later, I heard a voice.

'Where have you been?'

It was Jen. She was closing the door to a service closet.

'What were you up to?' I asked.

'Well, the door was open so I thought I'd check it out. Guess what? It locks from the other side,' she exclaimed, as if Christmas had come early.

Jen soon fell in step on the machine beside mine. Our workout seemed to drag on forever, then, seemingly in an instant, we were finished. Picking up my bag, I looked at the clock. Jen noticed where I was looking.

'Cigarette?' I quipped.

'Actually, no. Not particularly. But I could use a...' she began.

At that moment, one of the guys from accounting walked in.

'Hand with a filing cabinet,' Jen concluded, masterfully changing tact.

'Sure,' I replied, holding the door, as she exited.

Reaching the door to Jen's office, Jen breezed by, giving my butt a spank, as I waited to close and lock the door.

'So, where's this filing cabinet?' I inquired, facetiously.

'It's right over there. Could you check the top draw for me?' she asked, wearing a girly pout.

I raised a curious eyebrow, while Jen smiled from ear to ear. Sliding the draw open, a box of condoms, and a small tube of KY, drew into plain sight. Jen came to a stand beside me, as I picked up the lube.

'I don't think we'll need that today, but it's better to be prepared. Don't you think?' she whispered in my ear, as she plucked a condom out.

Kicking her shoes off, Jen pulled me closer and, like a rag doll, I followed. Systematically, Jen stripped away my clothes. I wasn't surprised when she decided to use my raging hard-on as a temporary hanger, before tossing the last of pieces aside.

Happy with the result, Jen gave me a look that was unmistakable. Without hesitating, I began slowly peeling away Jen's dark tights. I watched as her creamy thighs, and thin landing strip of pubic hair, materialized before me. Her feet free of the Lycra, I tossed her tights aside. Jen smiled nervously, as she slipped her t-shirt, and sports bra, over her head.

"Wow" was all I could muster, as I took in Jen from head to foot.

'I can't wait any longer,' Jen whispered, excitedly.

With little effort, Jen quickly separated the condom from its wrapper, and a moment later, had unfurled it over my length.

I forgot to breathe as Jen sat up on her desk and parted her legs, offering me my first unobstructed view. I stared in awe, much to Jen's delight. In fact, Jen seemed to reward my glowing review by relaxing back, pulling her knees up, and letting them fall apart.

'So, I thought we would both get a workout if we did it like this,' Jen suggested, fervidly.

'You hook your arms under my legs and I'll try to lift my ass off the desk. What do you think?' she finished.

'Sounds like a good start,' I replied, trying to stay in control.

Jen shimmied to the edge of her desk, as I gathered up a leg in each arm.

'Now be gentle. I haven't done this in a while,' Jen warned, trying to sound serious, but failing miserably.

Trying to gently push in, it was obvious Jen was telling the truth about it being a while. My initial efforts met with strong resistance, but she was also right about not needing to worry about lube. With a little persistence, her muscles caved and each stroke became increasingly easier.

Building up speed, Jen lay back, abandoning any attempt to hover. Prying her own legs wider, she began rocking her hips to meet my thrusts. Jen arched her back while she played with herself, and then everything seemed to just click. Within seconds, we were both shaking, gripped by our respective orgasms.

Panting, Jen lay unmoving, as I fought to keep my footing.

'W'oh. I almost forgot what that felt like. Look at me. I can't stop smiling,' Jen professed.

'Me too. That was awesome,' I responded, as I carefully peeled the now filled prophylactic, from my softening member.

'Pretty good work-out, huh?' Jen sneered, wiping her forehead with the back of her hand.

'Oh yeah. Now I really feel out of shape though. I don't think I could have lasted much longer,' I panted.

'Well, I guess we'll just have to work-out a little more often,' Jen counter, her voice a little raspy.

And so for the next week, our days became a variation on a recurring theme. Most days, we met at the gym, worked out, then snuck back to Jen's office for some one-on-one time.

The first few times, fearing recrimination, we sort of quietly rushed things. But by week's end, neither of us felt pressured to hurry. Jen's oral fix had been successfully quenched, so much so, that Jen confessed she no longer craved cigarettes, but instead was addicted to sucking my dick.

By the end of the second week, we were actively exploring the limits of each other's boundaries. Our comfort level had grown such that we didn't hesitate to offer, or request, any of a growing number of illicit acts. It was during one of our more probing sessions that we decided there was only one rule for each of us to respect; if someone says "stop", stop.

I was discovering a whole new world.

Anal play was my new favorite thing, and to my delight, Jen was happy to indulge my new fascination. More often than not, we'd start off trading places atop of Jen's desk, one of us slipping a few well lubed fingers into the other's butt, while orally hoovering their privates.

Jen seemed to enjoy the heightened sensation of having a few fingers, or a thumb, stretching her ass as she orgasmed. I too loved the added intensity that a few strategically placed fingers brought to our sexual exploits.

It was funny, but for all our anal antics, I couldn't work up the nerve to ask Jen if I could slip more than a few fingers in her rear.

Friday signaled the end of our third week. Both of us were displaying the positive effects of our new regime, our bodies tightening in all the right places, and the intensity of our workouts increasing steadily.

As I pounded out the last minutes of my run, it was no surprise that both of us were getting visibly excited. Neither of us could stop grinning, as we strode towards Jen's office. I was already sporting an immense erection as the office door clicked shut.

'So, my period's due this week,' Jen casually informed me, as she circled behind her desk.

Instantly, my high evaporated, as the reality of her words sunk in.

'Should we take a break?' I asked, hoping Jen was not offended by my leanings on the subject.

'Well, I'm not really into...you know,' she replied, screwing up her nose.

I nodded; relieved she was of the same mind. However, I still couldn't help feeling a slight tinge of disappointment. Then Jen dropped a bombshell.

'But maybe, you could...just...fuck my ass instead,' Jen stated plainly.

I couldn't help smiling.

'Really?' I asked, trying to contain my excitement.

'Yeah, really. In fact, I don't think we have to wait until it arrives,' Jen continued, as she opened the top draw and retrieved the lube.

Closing the draw, Jen stood very close. My shorts fell to my ankles, as Jen slid them off my hips.

'I think...' she whispered seductively, while deliberately lubing her middle finger.

'You could start fucking my ass...right...now,' she breathed, as she slipped between my cheeks, and shoved her slick finger home.

'Hokay,' I stammered, as Jen began to finger me.

'But first, I thought we'd have a little fun. Is that alright?' Jen asked, as her free hand began to jerk me off.

'Oh yes. Jen, that feels so good. Please, don't stop,' I pleaded, as I felt Jen stretch me further with a second finger.

'I have no intention of stopping,' she said, adamantly.

A moment later we were tearing at each other's clothes. Foreplay was a staple of our sessions, though, depending on circumstance, it varied in length. Today, we both seemed keen to take our time, as we explored each other with renewed vigor.

For the first time, we didn't take turns. Instead, we mashed our mouths together, and roughly groped at each other's sex. Neither of us held back, our fingers finding new depths.

Presented with the choice, I had opted to finger Jen in the traditional sense. She now lay writhing on the floor, with three of my fingers repeatedly burying themselves deep inside of her, all the while, a few of her fingers, diligently probed my inner depths.

Both of us moaned, as we abused each other's bodies absolutely; Jen gasping, 'So good. So good,' while I panted, 'Yes, oh yes.' Caught up in the moment, I failed to notice that I had subconsciously added my pinkie. But Jen did.

For the briefest moment, Jen held her breath, and shot me a look of panic, before groaning loudly. Her legs had instinctively snapped shut but then became seemingly unhinged, strewn in opposing directions, as she rolled on to her back, her hands desperately trying to grip the carpet.

Diving in and out, palm open, I marveled as Jen's body seemed to surrender any resistance and I found myself pushing ever deeper. During our continued frenzy, Jen let out a frantic groan. I stopped abruptly, fearing I'd gone too far. Jen half dazed sat up, looking at me as if asking if everything was alright.

'Are you okay?' I asked, quickly.

'Yeah. Are you?' she countered.

'Yeah,' I replied a little confused.

'So why'd you stop?' she asked, taking a moment to catch her breath.

'I thought...my mistake,' I finally answered.

Jen shook her head, gave me a quick grin, before snatching up the lube, and tossing it in my direction. Crawling closer, she patted my backside, indicating I should kneel on all fours.

The cap's pop, and the squirt of the lube, were the only sounds I heard before Jen had again parted my cheeks and slipped her fingers back inside. Totally lost in the intense sensations, it took more than a few strokes to realize that Jen was fingering me with three fingers. The thought sent a surge of blood south, further heightening every movement.

Everything felt incredible and then Jen paused. I looked back curious and a little frustrated. Saying nothing, she raised a questioning eyebrow. Knowing it's meaning, I mimicked her expression only to have it wiped off my face, a second later.

The slow stretching sensation became a strain, as Jen carefully inserted, for the first time, all four of her fingers. I went weak at the knees, as Jen began rhythmically bottoming her hand out. 'Too much?' Jen cooed.