Healthier Habits

'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.'