Ann's Two for One Deal

I still remember the day with extreme clarity. It was a day of many surprises and an exciting discovery, one which would live with me forever.

It all started out with my group of colleagues on a simple chillout session after a hard week of work one Friday evening. There were five of us from the same company - James, Elaine, Henry, Ann and I. James and Elaine were a workplace couple while Henry was already married with a kid. That left Ann and I as the only single and socially active ones, which meant that the two of us were outnumbered when it came to decide on what we were going to do that evening.

"No clubbing?" groaned Ann as she crossed her legs on the hawker centre stool as they finished up their dinner.

"Nope," mumbled Henry. "I'm ok if we chilled at someone's home but I don't want to go to Butter, Zouk or any of those other loud places. Besides, I need to be back by midnight."

Sighing in resignation, I made the decision on behalf of the whole group. "Look, if we're going to hang out at someone's place, then I think we should go to Ann's place. It's definitely the nicest of all our homes and she's not got a wife hovering around waiting to nag us."

I could see nods of agreement across the table. Ann, a Malaysian expat, had been given a very plush condominium by the company up near Grange Road, a large 1-bedroom unit complete with large HDTV, king-sized bed and upscale furnishings. Of course, this also didn't take into account that my own roommate had told me not to go back to our apartment before dawn as he was planning to bring home and bonk a local university undergrad that he had met at a party the night before.

"OK fine, we'll go to my place then," said Ann. "I've got quite a lot of alcohol left after my previous chalet stay with my old classmates so we can finish that up instead."

After adjourning to her place, we broke open the bottles of Jack Daniels and Tiger beer, drinking away the stress and sorrows of the past week. By the end of the session, we were all fairly plastered, largely due to a drinking game we played with shots of JD and an episode of Friends that was showing on the cable TV. It didn't take long before James and Elaine called it a night, the drunken Elaine being manhandled into a cab by her exasperated boyfriend. Before we knew it, it was just Ann, Henry, and I sitting on the floor of her living room, surrounded by half-empty bottles of booze.

She was halfway to being passed out, eyes closed as she took a quick snooze while the alcohol kicked in. I had always found her to be attractive, with delicate facial features on a narrow face that always seemed to have a mischevious smile on it, framed by long hair dyed a light brown that fell to her shoulders. While she wasn't the most well-endowed girl in the office, she had a fit body with a narrow waist, a taut ass and skinny legs that seemed to stretch forever downwards. It was what one of my cruder colleagues had referred to as being "a really bangable body combined with a CFM face, just waiting for you to up her". So yes, definitely a hot piece of ass if there ever was one! All those gym sessions that she went for had certainly paid off.

Checking my watch, I realized that it was nearly 4 in the morning and decided that it was about time to call it a night. Or was it a morning? Either way, I felt that the buzz and dizziness that accompanied the earlier binge drinking was starting to recide and I was looking forward to getting back for a good night's sleep in my bed. Henry was equally boozed up, and pulled out his phone to call a cab.

I reached over and shook Ann's shoulder, getting a soft groan in response.

"Hey, I gotta leave soon," I said softly as she tried to swat my hand away. "It's past 3 and I need to head back soon so that I can wake up for my tennis session tomorrow morning."

Her semi-coherent mumbling stopped as her brain finally processed my words. She forced her eyes open and stared at the clock on the kitchen wall.

"Shit, I need to be up early too," she complained as she grabbed onto the sofa she was leaning against to pull herself to her feet. She walked towards the door, stumbling as she fought the effects of the alcohol that she had imbibed earlier. Henry and I raced forward and caught her before she tripped, with each of us tucking one arm each under her arms to prevent her from sliding to the floor. I grunted as I slung her dainty arm over my shoulder, supporting her weight as Henry and I directed her towards her bedroom.

"Thankss..." she grunted as I shouldered the door aside and put her down on the bed. She looked so tempting in her skimpy homewear, a pink tank top accompanied by a barely-there pair of white shorts which left the majority of her slender legs uncovered. While a dozen naughty thoughts were running through my head, I forced myself to shelf them lest I regret doing anything stupid the next morning.

"OK, we're going to head down to catch a cab," I told her as I stepped away from the bed. "You'll be OK right?"

Ann moaned and grunted, then slid backwards along the bed and propped herself up against the backboard. Henry sighed at having to deal with the situation and turned to head for the door.

"Hey... can you guys wait a minute?" she called as I was just about to leave the room.

I paused and turned around, wondering what she was up to when she said "it's quite late already, why don't you two stay over tonight? You can get your tennis stuff tomorrow."

It was a good idea, given our less than sober state and the high likelihood of being cheated by a cab driver who would take advantage of our drunkenness to bring me on a round trip tour of Singapore before dropping us home.

Henry and I exchanged a glance and nodded, and were about to say thanks when she pushed herself off the bed and walked over to me and whispered in a low voice.

"Besides, I've always found you two studs to be the hottest men on the team... let's make this night a special one."

With that, she threw herself onto me and forced me back against the wall. I was stunned at the turn of events and was barely able to react before she pushed up against me, crushing her lips to mine in a desperate kiss as her arms roamed up and down my chest. It was a moment of shocked inactivity for me as she pressed her advantage to slide her body up against mine, feeling her soft breasts rub against my chest as she engaged me in a passionate french kiss. Then the alcohol took over as I returned the kiss with equal energy, my hands roaming up and down her back, feeling every curve of that taut, model-perfect body that was begging to be discovered. I ran my fingers down the small of her back and squeezed her tight butt, listening to her moan as she broke off the kiss and looked into my eyes with a gaze of pure lust.

As quickly as that happened, she pushed off against me and pulled Henry closer, catching him off guard as she wrapped her luscious lips over his and started Frenching him in a rather aggressive manner.

Then, she took it to the next level.

"Mmm... let me see how well-equipped studs like you two are," she purred as she ran a hand down each of our crotches and began rubbing in a steady rhythm, causing Henry and I to gasp in shock. Before my brain could process anything further, she immediately dropped to her knees in front of me and unfastened my belt buckle with expert ease before doing likewise with Henry. She gazed with eager eyes at my crotch as she slid my jeans to my knees, revealing my red boxers filled with my little bro who was now standing at attention thanks to Ann's sexual attack. The tip of my tented underwear with already wet with precum, something that seemed to excite her even more as she yanked my boxers down, allowing my cock to spring to attention and salute her with all its big red glory.

Switching her attention to Henry, she yanked his trousers down with gleeful abandon, admiring the massive bulge that emerged from within. A pull on his boxers was all it took for Henry's 7 inch dick to spring out in all its glory.

Ann looked up at us and grinned with a twinkle in her eye. "I always wondered what your sausages looked like... I see that they are as big as I fantasized them to be!!"

With that, she reached up and took my cock into her right hand, her touch causing me to gasp in pleasure as she gently ran her fingers over the top of my swollen member. She used her left hand to rub the top of my dick head as she slid her right hand up and down my shaft, bringing about an intense sensation of pleasure as Ann worked my dick over with expert technique. She'd obviously had lots of experience before that (as company rumors went), with each touch a delightful spark that threatened to send me over the edge. I never imagined that I would ever be in a position like this, vulnerable before my hot colleague, but that's what I was enjoying as she continued to stroke my dick with a steady rhythm.

Keeping up the beat on my cock using her right hand, she reached out to Henry with her left hand and grabbed his member, running it up and down his erection with the joy of a new present. Henry gasped as her ministrations brought him an all new level of pleasure, all memories of his wife and children forgotten.

And then she took my dick into her petite mouth, the warmth of her soft lips enveloping my cock in an overwhelming sensation of utter pleasure. I could feel her tongue running along the length of my little bro as she took more and more of my dick into her mouth. She playfully swirled her tongue around it and began to take the full length down her throat, her eyes closed in concentration as she took in as much as she could. I took a deep breath as I leant against the wall, my minx of a colleague devouring my cock like her life depended on it. Ann's lips made lewd sucking noises as her pretty head bobbed up and down my rigid rod, causing me to grunt and groan with the intense pleasure, having not experienced such skilled stimulation since that "work" visit to Batam.

It turned me on that this highly-educated colleague of mine, a well-paid and well-trained consultant, was sucking me off in her own bedroom like the sleaziest of Geylang whores. Ann's oral stimulation was like that of a seasoned pro, her tongue flicking across the sensitive cockhead as she massaged my balls in her right hand. She then released my balls to reach down and unbutton her own shorts, sliding them down to her knees to reveal a complete lack of underwear, her shaved pussy already glistening with the joy of female wetness. Moaning in her own bliss, she started to rub her pussy lips, her fingers moistened by her own juices, causing her to increase the rate at which she was working on my dick. Eventually, her horniness got the better of her and she slid two fingers into her slit, eliciting a muffled groan of delight as she pleasured herself.

Switching it up, she pulled Henry closer and sank her lips over his erection, causing him to gasp as her enthusiastic fellatio efforts brought him to the brink of ecstasy.

I had never imagined that someone of Ann's stature and refined elegance to behave so whorishly, her insatiable hunger for cock amazing me even as she brought me to within an inch or two of a sensational orgasm. However, her experience must have told her that I was near the edge for she slowly ran her lips one last time down my rock-hard little bro and then opened her eyes to gaze up at me with a look of pure lust.

"Mmm, so good... you two are the biggest I've ever had so far," purred Ann as she ran a finger down the bottom of my dick, raising it to her eye level as she looked at it contemplatively. "However, I want to see how you two feel inside of me, so... come fuck me now!"

With that, she grabbed our hands and pulled us over to her bed and pushed me down on my back. As I laid there, she peeled her tank top off, revealing a pair of perky tits that were firm, tanned and well-sized, possibly a large athletic B-cup or so. Ann kicked off her shorts from around her ankles and clambered on top of me, her deliciously nude body straddling my lap as she positioned her sopping wet cunt over my erect cock. Looking back at Henry, who stood there in amazement, shock, and lust, she said, "wait there, your turn will come".

With a smile of anticipation, she carefully eased herself down onto my dick, my hands gripping her slim waist to guide her downwards as my manhood slowly sunk several inches into her wet, velvety pussy. She felt amazingly tight as she started riding my cock, grinding her pussy onto it as she undulated her hips and threw her head back in a gasp of joy. I started grunting softly, punctuating her soft feminine moans as she bounced up and down in a swift motion.

"Fuck... that feels so good inside me!" she cried out as her petite body was speared by my erect dick, her hands on my chest as I massaged her perky tits with my hands, feeling her erect nipples harden even more as I rubbed them with a teasing touch. "Mmm... fuck yea... fuck me more..." Ann moaned, her tight body coated with a sheen of sweat as her body reacted to the pleasure of her carnal fuck session. I pulled her closer to me, pursed my lips and sucked on her amazingly dark nipples, one after the other, causing Ann to throw her head back and cry out in sheer pleasure. She moaned and called out my name like an insatiable slut as she thrust herself onto my dick. It was too much for me to take and I motioned for her to pause and slide off me.

As she slowed down and eased off me, Henry took that moment to grab her by her waist and spin her down onto the bed, her tight body bouncing off the soft mattress as he pulled her to him and lifted her slim, long legs around her neck, exposing her shaven pussy lips. Without hesitation, Henry the married man positioned his dick head at his slutty coworker's entrance and speared deep into her in one smooth motion, causing her to yelp in rapture as he penetrated the depths of her sweet cunt, thrusting deeper and more powerfully into her slick pussy.

"Fuck... yes... that's it... fuck me harder..." gasped Ann as she closed her eyes in her bliss as Henry gave her what was the fuck session of her life. The thoughts of such frantic fornication with this well-educated slut of a colleague only made him plow her pussy faster and harder with each stroke as she moaned and screamed like a cheap whore.

Staring down at her naked body writhing with pleasure, it was the best feeling in the world as I watched her satisfy her depraved cravings, as we gave her what she wanted and deserved. Stroking my cock as I watched, I was stunned by what happened next.

She shoved Henry off her with surprising strength, causing him to fall backwards. Ann reached over to her dresser and grabbed a bottle of KY jelly that was lying there. She motioned me over to join them on the bed, and handed Henry the bottle of lube.

"I have never had two men inside me at the same time. I think tonight's going to be my first time. Are you boys up for it?" she asked with a wink. Henry and I looked at each other and nodded in consent.

"Very well then," Ann purred and pulled me into the bed so that I was lying facing her. "Let's get started". She said back onto me, her tight pussy now wet with both her own juices as well as precum from both Henry and I. As she slowly slid up and down my dick, she motioned for Henry to lube up. Once he was ready, he climbed on behind her and got ready.

Ann grinned like a nymphomaniac and bent forward so that her tight butthole was exposed to Henry. She paused her movement for a second as Henry, apparently no stranger to anal sex, placed his dick at her anal entrance.

Ann reached behind her to guide him into her ass, and I could feel his massive dick through the thin wall separating her pussy from her asshole, as it pushed inch by painful inch into her. Her gasps of pain and pleasure were a sign that her previous partners had never stretched our her ass that wide.

I could feel her clench her vaginal muscles as Henry's dick sank deep into her ass, her tight pussy getting even tighter as she was completely filled by the two dicks of her co-workers. Slowly, we built up a rhythm as a trio, both Henry and I pistoning into her in sync with each other. Thanks for the DP session, she felt even tighter than before and I was brought to the limit of my stamina as she moaned and groaned like a simple whore. While I had always assumed she was slutty, this brought her to new levels I had never imagined she was capable of reaching.

It didn't take long before Ann's cunt tightened around my dick and she came hard with a gasp of "I'm cumming", her toes curling in rapture as her pussy tightened around my pulsating dick and causing her to arch her back in response to the intense waves of pleasure.

Henry, knowing that he could never cause pregnancy complications through anal sex (his wife would kill him if he had to deal with a child by another woman), realized that he could cum at will. Driven by her own rapturous orgasm, he pushed deep into her one last time and erupted, sending a flood of cum into the depths of her ass. With that done, he pulled out, leaving a trail of cum leaking out of Ann's ass.

It was all I could take as I reached my own climax, pulling out of her wet cunt to aim my cock at her pretty little face. And then I came, unleashing a torrent of hot cum onto her face, strings of gooey seed hitting her eyes, nose and mouth and coating her delicate features with a layer of my cum.

To her credit, Ann opened her eyes, reached for my cock and then sucked at the swollen soft tip to extract every last bit of cum from my dick like a cum-starved slut. My jizz covered her face like a thick frosting, which when combined with her CFM look made her look like a pornstar. Except that she was MY real life pornstar and she had just given me the fuck of my life.

As I collapsed back into bed beside her, she took a tissue to wipe some cum off her nose and lips before leaning over to give me a tender kiss. Then she pulled Henry over and sucked on his softening cock, a true ass-to-mouth experience that I doubted Henry ever experienced at home.

Of course, as she did that, she gave my softening dick a gentle, teasing rub, causing me to groan in despair as she grinned cheekily. Then she collapsed into my arms and drifted off into a blissful sleep. As I lay there, I locked eyes with Henry and waved him off - there'd be hell to pay with his wife if he were to end up sleeping over.

I wondered how I would ever be able to focus at work the next time I saw Ann in the office. Would memories of our raw fuck session distract us from our daily tasks? Was there more to come in the way of banging in the office? Either way, I had seen what this slut of a consultant had to offer and it was to be the first of many sexual liaisons in a high-powered workplace.