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.
‘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….”
“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.
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.
‘No…no. I’m f’uh, f’uh fine,’ I replied.
‘How about when I do this?’ Jen asked, as she started to firmly stroke my erection, coating it with lube.
‘Oh shit,’ I growled, as an intense throb pulsed between my rectum and my penis.
A heartbeat later, I exploded all over Jen’s carpet. Jen exhaled, satisfied with the result.
It took a few moments for me to even utter a word. While I recovered, Jen had unzipped her bag and pulled out a towel. But as she knelt down to mop up, giving me a tantalizing view, I had subconsciously clasped my penis. It only took a second to register that I was still rock hard.
Moving deftly, I crept up behind Jen. As she stood to admire her handy-work, I reached round and, cupping her breasts, firmly pressed my mast between her cheeks. Jen tilted her hips forward grinding my shaft over her anus, the lube making for a frictionless track.
‘You’re just the energizer bunny today, aren’t you?’ Jen whispered in my ear.
‘It would seem so,’ I replied, feeling my head dip again as it passed over Jen’s anus.
‘That feels sooo goood,’ Jen cooed. ‘Do it. Try to push it in.’
‘You sure?’ I asked, giving Jen one last out.
‘Yes,’ she answered, pulling a cheek aside, proof of her conviction.
Taking a deep breath, I moved down a little. Finding her knotted entry again, I slowly began to stretch Jen’s ass. Jen groaned loudly as her ring strained wider, letting my head penetrate her rectum.
‘Wait, wait, wait, wait…’ Jen repeated quickly, as she reached one hand out to steady herself, while the other squeezed my thigh lightly.
The feeling was insane, as Jen’s muscles spasmodically squeezed round my shaft. It was a long moment before Jen looked over her shoulder and gave a small nod.
‘Okay.’ she finally said, exhaling deeply.
With her consent, I started feeding more of my cock in to the furnace that was Jen’s ass.
‘You feel so big,’ Jen panted, as she struggled to pull her cheeks wider apart with one hand.
Both of us sighed as my hips finally nestled against Jen’s cheeks. I started to withdraw when Jen squeezed my hands.
‘Don’t move. Not yet. Just give me a second,’ Jen said quietly.
Jen’s rectum still pulsed, but gradually the waves subsided as she adjusted to the new intrusion. It was Jen who began to gently rock herself along my shaft.
‘This feels good, but I need more lube,’ Jen confided, after a dozen strokes.
‘Besides, I read it feels really good if I lay back, pull my legs up and…well, you can figure the rest out,’ she suggested, sexily.
Both of us were insanely horny, yet we took our time. Jen, using both hands, generously lubed my erection. Satisfied I was adequately prepared she crawled up on her desk and, settling on her elbows and knees, presented herself perfectly.
Reaching out, I couldn’t help but run a few fingers back and forth, over Jen’s anus, each pass, inciting a lustful sigh from Jen’s lips. Not wanting to tease too much, I set to the task at hand. Jen’s rectum, having been invaded on a regular basis, instinctively relaxed to my touch, as I used one, then two fingers to lube her way.
‘Alright, I’m ready,’ Jen announced, turning over.
‘Are you ready?’ she asked.
Grinning, I nodded. Jen slowly pulled her legs up and out in a way I would normally refer to as obscene, if it just wasn’t so damn hot.
‘Well, don’t just stand there. Fuck me!’ she commanded, playfully.
Jen held her breath and closed her eyes as I grasped one of her legs, lined myself up, and pressed forward.
Staring down at Jen’s ass swallowing my dick was the hottest thing I’d ever seen. A momentary wince from Jen served as a stark reminder; take it nice and easy. My cock looked huge in comparison to Jen’s ass, which was stretched wider than I’d ever seen. Jen let out a moan as the last inch disappeared. Her eyes remained closed as she gave herself the time to adjust once again.
Finally opening her eyes, Jen propped herself up on her elbows, looked down.
‘My ass is tingling,’ Jen giggled, as she wiggled hips a little.
I met Jen’s eyes and without warning, pulled my hips back a little, and thrust forward gently.
‘Mmmm,’ Jen hummed, contentedly, as I came to rest.
‘That feels good. Just like that,’ she instructed, brightly.
With a green light, I gently started fucking her.
It was heaven. Jen’s ass was so tight, but in a way I’d never felt during regular sex. Her rectum enclosed my entire shaft, constricting it perfectly. And then there was the view. The ultimate combination of Jen’s stretched ring, desperately gripping and groping, while her swollen, sopping pussy lay slightly agape.
Leaning in, Jen instinctively laid back, letting me pin her knees back closer to her breasts.
‘Oh, yesss,’ Jen moaned as I ploughed deeper.
‘So, you like this?’ I asked, grinning at her.
‘I do. I really do,’ she replied, nodding adamantly.
Jen gave a few squeezes and grinned cheekily, so I responded. Grinning back, I started fucking her with a renewed sense of determination. The effect was immediate. Gone was the playful smirk, replaced by a look of desperation.
I now focused on the growing sensation, welling up from deep within. It had taken a while thanks to Jen’s earlier molestations, but my body was ready to unleash another orgasm. The realization of that fact spurred me to gauge Jen’s progress.
Now out of my selfish bubble, I quickly realized that Jen was unusually tense compared to our past encounters. Her body had all the trademark signs that she was close to cumming, but she somehow looked frightened.
Then Jen blurted, in a desperate voice, ‘Faster. Oh, faster. Oh…Oh, yes.”
I responded immediately, our skin now slapping together more and more. I fought to hold on, but abruptly my dick involuntarily spasmed hard, sending generous waves of pleasure throughout my system, and whatever cum I had left in to Jen.
Jen shut her eyes tightly, her face taught. An instant later, she inhaled sharply and, arching her back savagely, cried out, ‘OH GOD!’
Her body seemed to seize for a long moment before releasing her, letting Jen cover her face with both hands. I kept pumping Jen’s ass, feeling the bristling sensations still reaping havoc across her body.
The overwhelming sense of satisfaction quickly faded as I realized Jen was crying into her hands. Fearing the worst, I quickly released Jen’s legs.
‘Jen…Jen?’ I asked, more than a little worried.
Jen didn’t reply, she just kept sobbing into her hands. Her thighs were now either side of my hips, and I began to stroke them tenderly.
‘Jen, what is it? What’s wrong? Are you okay?’ I pressed, my concern growing exponentially.
Still getting no real response, I carefully reached out and moved Jen’s hands aside. Waiting beneath was a tear streaked, but smiling face. Jen began wiping her eyes as she started to sit up.
‘I don’t know why I’m crying. I feel stupid, but I can’t help it,’ she half choked.
‘That was….’ Jen started, but trailed off.
‘So, you’re okay?’ I asked tentatively, still a little confused.
‘Well, yeah. You just gave me an orgasm that made me cry ya dummy,’ she replied, batting my stomach with the back of her hand.
Breathing an audible sigh of relief, I gave Jen a bear hug.
‘You scared the shit out of me. I thought I’d done something wrong,’ I jokingly scolded, giving her a light smack back.
‘Shit no! That was the biggest orgasm I’ve had in…well, I can’t remember,’ Jen beamed, happily.
Jen now sat back on her hands, chest out, kicking her legs absently. Her face was still a little puffy from the tears, but in every other respect Jen was as giddy as schoolgirl.
‘I have to pee, ‘ Jen announced, out of the blue.
With that, Jen poked me in the stomach, hopped down and started throwing on her clothes. When she finished, she came over and, hooking one arm around my waist and squeezing my butt with her other hand, gave me a deep kiss.
‘I think we should do that again. Soon!’ Jen declared.
‘I think we can arrange that,’ I replied, giving her butt a playful squeeze back.
Jen nodded, gave me one last kiss on the cheek, and headed for the door.
The success of our first attempt at anal sex prompted a new, very welcome addition to our repertoire. Jen’s assurances that her butt felt fine, loose but fine, gave the green light for the two following sessions to feature Jen’s butt.
‘You know, if you’d asked me a month ago if I’d be in to anal sex, I would have said “No”. But now I’m beginning to prefer it,’ Jen professed as she confidently cruised along at a cracking pace.
‘Well, I’m more than happy to fuck your butt anytime you want,’ I offered smiling.
‘I’m sure you are,’ she smirked back.
Another month passed. Jen and I had established a routine of three days a week in the gym at work, then back to Jen’s office, and one evening where we ran a path through a nearby wildlife reserve for a change of scenery. Sex was not an expectation, but we more often than not gave each other a playful feel up.
Walking in to the gym at my usual time, I was met with a cheery hello from Amber, one of the girls from Jen’s department. Actually, Amber had the office adjacent Jen’s though I only ever saw her there on the odd occasion. Smiling and returning the greeting, I climbed on to one of the treadmills and fired it up.
Settling in to a rhythm, I found myself stealing glances at Amber. Amber was beautiful. When I first met her, I thought she’d be fun to date right up until Amber mentioned her fiancé. Any potential for romance scuttled, I had settled for just friends. As it turned out, Amber and I had a lot in common so whenever we had the opportunity, we didn’t hesitate to catch up.
About ten minutes had passed when Jen stepped through the door and gave the two of us a big hello. I didn’t know what it was, but something was different with Jen. It wasn’t anything she said, just an air about her. With Amber in the gym, I would have to wait to find out what was up.
The three of us worked out, sharing the occasional small talk. Amber soon dismounted her exercise bike and waved good-bye to both of us.
‘I wonder if she’s working late. Might have to skip our usual office antics if that’s the case,’ I puffed.
Remembering my early curiosity, I looked at Jen and asked, ‘So, what’s with you?’
‘What?’ Jen grinned back.
‘Something’s up with you. Spill,’ I shot back hitting the treadmill’s kill switch.
Jen was smiling ear to ear, but she just waved a finger at me and replied, ‘I’ll tell you later back at my office.’
Now I was really curious, but Jen wasn’t going to let anything slip so I just poured myself a cup of water and waited patiently.
Mercifully, Jen cut her run short. Heading for her office, Jen didn’t say a word, ignoring my attempts to get her attention. Passing Amber’s door, I felt relieved to find Amber was nowhere to be seen.
Throwing my bag in the corner of Jen’s office, I turned and locked the door. Jen stood in the middle of the room, waiting for me to finish.
‘I have something to tell you,’ Jen started nervously.
‘I’ve met someone. Peter, well Pete,’ she amended.
‘I met him a few weeks ago at that conference I flew out for,’ Jen said, sparking the memory of a particularly great session as she would be away for a few days.
Matching my smile, she continued, ‘So, turns out Pete is from around here. We’ve been on a few dates and I really like him.’
‘That’s awesome, and don’t worry. We can go back to just being gym buds,’ I said reassuringly.
Relieved, Jen leapt forward and gave me an almighty hug.
‘Thanks for being so understanding,’ Jen said sincerely. ‘I knew you would be so, I thought I’d do something special to say thanks.’
Opening the now infamous top draw, Jen retrieved a black piece of cloth with some elastic hanging from it.
‘Put this on. And no peeking!’ she instructed.
It was a blindfold. The type you would get in a travel toiletry bags. Slipping it in to place, I felt Jen take my hand.
Leaving me, back against the wall, Jen said, ‘I have to get something from my car. I’ll just be a minute.’
The door opened and closed then the room was silent.
This was hot. Being blindfold added a whole level of tension as my mind raced to guess what Jen could possibly have in store. I nearly jumped out of my skin when I heard the door handle turn sharply.
‘I didn’t scare you did I?’ Jen teased as I heard the lock click in to place.
‘If you do that again, I think you’ll need a ladder to get me down,’ I grinned blindly in the direction of her voice.
I flinched as Jen masterfully began stripping me bare.
‘Jump much? Just relax and let me give you your surprise,’ she cooed, her warm breath on my neck sending goose-bumps down my arms.
Feeling giddy, I took a deep breath and, giving myself a little shake, exhaled and said, ‘Okay.’
Jen really took advantage of my heightened state by tracing her fingertips over my stomach, arms, tops of my thighs, and over the rounds of my butt. It had been a while since Jen had teased me like this and never with a blindfold so I savored the anticipation. My dick was jerking madly, straining to feel Jen’s touch.
Then finally contact.
No hands, just her warm, wet lips pursed at the tip of my cock for a moment before she swallowed my length. I didn’t know if it was the blindfold, but there was something different. Not bad different, just different. Jen’s hands cupped my butt and gently pulled me in with each stroke.
‘Jen, I’m going to cum. I’m going to cumming!’ I warned her desperately.
Jen sped up a little, but what surprised me was her hands now urged me to really thrust. As I had done the very first time Jen had blown me, but never since, I reach out, clasped her head and began fucking Jen’s mouth. Without her hand stroking my shaft, I could feel my cock hit the back of her throat. Maybe a little further but I didn’t care.
‘Oh God. Yesss!’ I groaned as I came in powerful waves.
Jen took the initial surges then drew back and vigorously worked my shaft, sending cum flying.
‘How was that?’ Jen asked playfully as she continued to stroke away.
‘That was awesome. Best surprise I’ve had in ages, but I hope there’s more?’ I countered, grinning wildly.
I could almost feel Jen’s smile when she replied, ‘Oh, there’s plenty more, but first, let me take that blindfold off.’
For a moment, I could barely see. Then the room came sharply in to focus and I understood exactly what my surprise was. Of course there was Jen, standing there smiling, but the surprise was Amber’s face beaming up at me.
Amber was still stroking my cock as she said, ‘I hope you don’t mind? Jen said you wouldn’t.’
Clad in a sports bra and tights, Amber slowly rose to stand before me. As she straightened, I saw where my cum had landed. Amber’s bra and cleavage were tattooed with cloudy streaks that glistening under the incandescent light
I was speechless as the enormity of it all registered.
Both Jen and Amber shared a laugh before Jen said, ‘Oh, I guess I should explain.’
Handing Amber a towel, Jen began to tell the whole story.
It had all started a few weeks back when Amber, unbeknownst to either of us, had been working back late with the door to her office closed. I knew that Jen and I rarely worried about being heard because, for one thing, we weren’t that vocal and two, the department was always abandoned, so it came as no surprise that Amber had clearly heard us going at it.
At first, Amber had thought it was just a one off coincidence that she’d caught the two of us, but she’d soon figured out that it was a regular arrangement. After hearing us on one occasion, Amber had actually snuck a peek between the blinds by the door and witnessed me taking Jen’s ass. Where things took a twist was Amber’s now husband, had become completely work obsessed and consequently Amber’s sex-life had disappeared, so “naughty, little Amber” had been living vicariously through us, listening to our private training sessions while she had her own little sessions next door.
By pure chance, Jen had heard Amber one night after I’d left early and had gone next door to apologize and ask her not to say anything. Apparently, Amber hadn’t heard me leave so when Jen had opened the door to Amber’s office, there was Amber masturbating to a porno of a couple having anal sex on her screen.
Jen had figured out in a split second what had been going on, so, after a lengthy Q and A, the two of them had struck on the idea of Amber taking over Jen’s place. The only thing they hadn’t figured out was how to tell me.
‘So, there you go. What do you think?’ Jen asked as the two girls waited with baited breath.
When I didn’t reply right away, Jen spoke up and said, ‘Amber knows you have a thing for anal and she’s in to it. Right, Amber?’
‘Right!’ Amber chimed.
‘Apparently, we inspired her. What can I say,’ Jen finished, looking very pleased.
‘So, are you in?’ she asked again.
Turning to Amber I asked, ‘You’re sure you want to do this?’
‘I just sucked your dick. I think that answers your question?’ Amber replied.
‘Well, if you’re in, I’m in,’ I said, finally accepting the incredible turn of events.
With the new arrangement done, Jen gave Amber a hug before coming over to me.
‘I had a lot of fun,’ Jen said sincerely.
‘Me too,’ I replied, stepping forward and giving Jen a hug.
We held each other a long moment, then as we let go, I wished Jen good luck to which Jen replied, ‘I think you’re going to need some luck too.’
Nodding in Amber’s direction, Jen added, ‘It wasn’t the girl getting her ass fucked on Amber’s screen.’