Rachel Doesn't Do 'Normal' Pt. 02

Knowing what just might put her over the edge her took hold of her ass and spread her cheeks apart. The sight of her pink puckered asshole was too much of a temptation for him and he let a line of drool drip from his mouth and run down her crack.

Rachel was too busy concentrating on the imminent arrival of another earth shattering orgasm to realise what he was doing before it was too late.

Hank thumbed her sensitive ring gently and then without warning pushed his thumb inside her ass.

"UNGH! AH! W...WHAT??? N...N...NO NOOOO! NOT THERE! NOT THERE!" Her eyes flew wide open and she snapped her head around, shaking it violently. "STOP!"

Hank hadn't bargained on her having this reaction. Sure some women he knew weren't keen on anal, but this was just his thumb. He'd assumed a girl this kinky would be up for anything.

He removed his thumb, and slowed down his thrusts. Rachel whimpered as the intense orgasmic feeling that had been so close to being unleashed, began to subside.

"Sorry. I take it you don't like anal sex then? I won't try that again, I promise."

"Th...thank you." She panted. "It's not that I don't like it, well I mean I don't know if I'll like it. I've always been a bit scared to actually try it to be honest." She wasn't sure why she was sharing this much information with him, maybe her brain was still addled from all the adrenalin.

Hank's face was a picture of blank shock. His now stationary cock flexed inside Rachel's pussy.

"You...you've never tried it? What...ever?"

Rachel shook her head. She started to feel a bit embarrassed, as though she should be ashamed of her inexperience. She was 21, nearly 22 and all of her girlfriends had done it years ago, but after reading that it can often hurt, she'd never been in a rush to try it herself. That's not to say she wasn't curious though. Many guys had tried in the past, but she'd never plucked up the courage to give herself over to it.

Hank could hardly comprehend what he'd just heard. Here he was with his dick inside his employee's gorgeous girlfriend, only to find out that she had a virgin asshole. Never in his wildest dreams would he have thought that a girl this unbelievably hot, who had such a voracious sexual appetite, could have a hole that had never been touched by any man before him. All he could think about now was how on earth was he going to convince her that he should be the first man to plumb her virginal depths. To take away her last sliver of purity.

He knew he had to try.

"How did it feel when I inserted my thumb into you just now? Was that painful?"

Rachel thought about it for a second, then shook her head. "No it didn't hurt, it just felt weird. Alien. Like it shouldn't be there I suppose."

Hank's brain was a whirl of ideas as he puzzled over how he was going to handle this. First things first he needed Rachel to be in the right mood, so he began to slowly thrust his cock back into her. This was received with an appreciative giggle from Rachel.

"So you've thought about it before, but never had the courage to try it?"

"Mmmm hhmmm." Rachel nodded.

"Well how about I put the ball completely in your court. If you want me too, I will slip my thumb back inside you. I will be very gentle and will respond immediately to your every command. If you aren't enjoying it, then I'll pull it straight back out. But if you are relaxed and you find that you start to enjoy the sensation then I will go entirely at the pace you want me to." This was Hank using the tactful business side of his brain to full effect. Gone were his authoritarian barks and commands, his tone was now soft and soothing and Rachel considered his words for a long while.

"I don't know."

"You'll never know whether or not it could be something you enjoy unless you try. I hear that some women find it incredibly intense, and it can cause them to have really powerful orgasms."

"Really? Well..." Rachel chewed her lip as Hank held his breath. "...ok. Just your thumb though, and you'll stop if I tell you to?"

"Absolutely." The war was half won at least.

He picked up his pace once more and covered her asshole in his spit, thoroughly lubing it. "Just relax you muscles ok?" He said soothingly.

"O...ok..." Rachel gasped as she felt the foreign intrusion into her ass once more. Her muscles instantly clenched but she forced herself to relax around it. It felt strange, not really good or bad, just a bit odd. What did feel good though, was the 8 inch cock which was now happily spearing her tight pussy from behind once again.

"Does that feel good?"

"Uh huh!" She nodded, responding more to the sensations she was getting from the fucking, than from having his thumb in her ass.

Hank very gently worked his thumb in and out of her tightly gripping sphincter. "Oh you're a good girl." He started using his other hand to rub Rachel's clit.

Rachel started to tremble and thrash around on the desk. As the minutes passed, her moans became louder and higher pitched as she felt a surge of euphoric energy wash over her. "Fuck! That feels so good! Oh my god!" She tried to back herself onto his dick in an attempt to make him fuck her harder.

"Ungh! Ungh! Ungh! I'm nearly there! Make me cum!"

Hank abruptly stopped again, this time withdrawing his cock completely. There was no way he was about to cum anytime soon, his mind was solely focused on the goal of burying his dick inside this blonde bombshells virgin asshole. He figured if he kept Rachel on the brink of an orgasm, but never letting her tip over the edge, then maybe, just maybe, she would be willing to do anything to be allowed that release.

"What? Please don't stop! PLEASE!" Her hand replaced his as she furiously began to rub her clit, but Hank snatched it away. "No! That's not fair!" She pleaded. That was twice now that she had been denied, having come so close. Her body ached with wanton need.

"I can make you cum. Just let me fuck that amazing ass of yours, and I promise, I will make you cum harder than you ever have in your life." He wasn't sure if he could live up to that promise, but he would have said anything he could in that moment to get his dick inside her ass.

Rachel was fighting an internal battle within her own mind. The devilish part of her brain was speaking the loudest however. Anal was always something she had been curious to try, so what was she waiting for? She loved shagging dirty old men because of how degraded it made her feel. There was nothing that turned her on more in life than letting her gorgeous body get used by ugly old creeps. Nobody else looked at her, touched her or fucked her with the same desperate intensity than those who could never in their wildest dreams imagine they would ever be given the chance. Those that, not her, but society would deem unworthy to even kiss her feet. What could be more degrading than being buggered by Aaron's boss?

"...Ok. But go slow, and if I tell you to stop then I mean stop!"

The words were ringing in Hank's ears. "Absolutely...anything you say. My dick is yours to command."

"Good. First though, go back to your office and get my handbag."

Hank didn't bother to argue or ask why. He ran like a teenager to grab it and brought it back.

Rachel had to stifle a laugh as he jogged back towards her, his erect cock was slapping about his thighs as he went. She reached inside and pulled out a tiny bottle of lube, like many girls she always like to be prepared for any occasion. It had been a joke gift in a goody bag that her friend Emily had given her on her hen night. She was glad she had it now though.

Hank looked at her quizzically. "You never know." She shrugged.

Grinning from ear to ear, he set about lubing his cock and her asshole thoroughly. He nudged his tip against her puckered hole, causing Rachel to flinch.

"J...just t...try and relax." Something which he was finding hard to do himself. He couldn't contain his excitement, tears were beginning to form at the edges of his eyes and he wiped them away.

"Uuuhhhhh!" Rachel's body lurched forwards to try and get away from this strange new invasion, as Hank began to gently push the tip of his cock inside her. She controlled herself though, taking deep breaths, as she tried to keep calm. Hank couldn't believe how tightly Rachel's asshole gripped the tip of his cock. He thought it might be enough to cut off his circulation. Even with all that lube, it was a struggle just to get the first inch inside her. "UNGH! Oh god!" Rachel's body flinched and spasmed once more.

"You ok?"

Rachel nodded. "Keep going." She moaned breathily.

Overawed by his situation Hank pushed the next 3 inches in rather more swiftly.

"AH! OW! Ow...oooo...s...slowly."

"Sorry, sorry." He held his dick halfway inside her for a while, letting her adjust to its presence.

It was the strangest feeling. She felt stuffed fuller than she had ever been before. She'd also expected it to hurt more than it did, but was thankful that it didn't. There was something definitely wrong about it though, it wasn't pleasant, not yet at least. If anything it just made her feel dirty, nasty, like she was a cheap whore. In other words, everything she had hoped it would.

She groaned louder as Hank worked the 5th and 6th inches of his cock inside her before pausing for her to adjust again.

"Shit that feels good!" Hank mumbled, looking down at a sight beyond his comprehension.

Rachel grimaced with the short sharp bursts of pain, which his intrusion briefly caused, but she was determined to see it through.

"Ffffuuuuhhhh! Uuuhhhh shit!" Hank moped sweat from his brow as he finally felt her tight sphincter squeezing the base of his cock.

It was the first time in her life that Rachel had wished that a guy had a smaller cock, or at least a thinner one. The flourish of pride she felt for facing her fears quickly evaporated and turned into a need, a hunger, a burning desire, to have her ass fucked for the first time. To truly feel like a slut.

"Are you ok? How does that feel? Does it hurt at all?" Hank was still playing nice.

"Shut up! Just fuck my ass already!"

The devilish grin returned to Hank's face. "Well well well. The bitch is back. As you wish."

He started very slowly, pulling back only an inch or two before sliding back into her tightest of holes. His hand reached around and found her clitoris again, knowing full well what he was doing.

Rachel screamed as she felt her clit being fondled and teased once more. She began to pinch and tug on each of her nipples, as she revelled in the shame and debasement of having her ass fucked for the first time.

Hank found her sheer tightness prevented him from going at anything like the pace he had when he was fucking her pussy, but he didn't need to. He built up a slow but steady rhythm, while his cock was being milked like never before.

Rachel covered her mouth with her arm as she moaned and panted constantly. She managed to muffle a few cries of pain, but they were never that bad. In fact the pain seemed to intensify the pleasure she was feeling. She locked her arms straight and pushed her body up off the desk, craning her head back and screaming at the ceiling as Hank began to rapidly flick his finger across her swollen clit.

"You like getting fucked in the ass don't you baby?"

"Uh-huh!" She looked back over her shoulder and watched in awe as her anal virginity was finally being taken.

"You wanna cum so badly, don't ya?"

"Uh-huh!"

"Yeah you love getting your ass pounded by my big old dick don't you?"

"UH-HUH!"

Rachel was on the verge again. Her head was swimming and her body trembled as she braced herself for a long awaited climax.

"Cum for me then baby! Cum for daddy!" He frantically fiddled her clit as fast as he could until he felt her body tremble then tense up completely.

"UH! UH! UH! FUCK! HHUUUUHHHH!! YYEEESSSSS!! AAAAHHHH..." Rachel's voice trailed off into a silent scream as the orgasm struck her.

She tried in vain to blink the world back into view as her vision went hazy, and she slumped forwards onto the desk.

Hank felt her pussy juices gush from between her legs, but continued to pound her ass and tease her clit throughout it.

She thrashed around on the desk like a woman possessed, clenching and relaxing the muscles around her ass involuntarily. "Oh Gaaawwwwddd! Oh my...oh fuuuuhhhh..."

"Enjoyed that I bet?" Hank teased, but Rachel didn't have the energy to respond.

Her clit was now almost too sensitive and she tried to push his hand away, but he continued to toy with her. A few more mini aftershocks tore through her limp, twitching body as she mewed with contented pleasure.

Knowing he was entering the home stretch Hank picked up the pace ever so slightly. Rachel grit her teeth and accepted the weird and at times uncomfortable feeling that was filling up her insides. She was getting off on feeling debased instead.

She looked over her shoulder again and watched her ass rippling as he pounded away at her.

"Are you going to cum in my ass you dirty fucker?"

"You know I am!"

"Fuck it then! Make me your whore!"

"YES! You gorgeous little slut you!" He spanked her ass cheek sharply and Rachel screamed.

"Harder!" Rachel growled. "Spank me HARDER! YOU BASTARD!!"

He rained down a series of hard slaps onto her pert, juicy ass. His cock flexed inside her. He was seconds away.

He stopped teasing her clit and took hold of both of her huge swaying tits, crushing them in his hands.

Rachel was close to another orgasm too and her hand replaced his, as she fiddled her furiously.

"UUUNNNNGGGGHHHHHH!!" Hank's cock exploded into Rachel's insanely tight ass. His body hunched over hers as he shot his first load deep inside. "AAHHHH!" He let his teeth sink into her slender shoulder as he grunted through a second blast of cum from his painfully hard cock. "SHIT! OH JEESSS...UUSSSS!"

After his third spurt, Rachel's body was wracked with another equally intense orgasm. "UUHHHH!! SHIT!! FFUUUHHHHH!!" She screamed and writhed beneath him, gushing juices all over the floor, as her rectum was steadily filled with the most cum Hank had ever produced in all his years.

Realising just how tightly he was mashing her breasts with his hands, he quickly relaxed his grip. He stayed hunched over her for a while though, kissing her shoulder and lightly caressing her now tender breasts.

They both let each come down from their incredible highs. Nothing was said or needed to be as all that could be heard in the room was the sounds of their heavy breathing.

Hank eventually stood up and slid his withering cock from Rachel's newly christened asshole. He watched as her sphincter closed back up into a tight little star, knowing full well that he must be, in that moment, the luckiest man alive.

Rachel still couldn't move. She shivered and shuddered as she fought to recover her senses. He hadn't been lying when he said he'd make her cum harder than she ever had before. That was beyond intense.

Hank picked up the framed photo which had fallen forward next to her on the desk. In it her dazzling smile made her look so angelic and innocent, like butter wouldn't melt.

The reality was so much different. His eyes travelled up along her stocking clad thighs, taking in every detail of the hour glass curve of her bottom, framed by her bright red suspender straps. Her tanned skin was completely coated in a fine sheen of sweat.

He gazed at the swell of her magnificent tits as they splayed outwards on the desk under the weight of her body. Her hair was a mess, loose stands hanging down from her misshapen bun, but she'd never looked more beautiful in his eyes, than she did right then.

He wished he could take a photo of her now and put it on his desk, but knew he would have to settle for his memories.

Rachel eventually composed herself and set about putting her clothes back on. She decided she would have to be the one to break the rather awkward silence that had developed. "I think that was worth double his pay and a company car. Don't you?"

"Honey, I will buy that boy a fucking Lamborghini if it means I get to do that again."

Rachel laughed as she straightened out her jacket. She pulled out the clips keeping the remains of her bun in place and ruffled her hair back into reasonable shape.

"Are we off then?"

Hank didn't really know what to say in the elevator ride down. He put his hand in his pockets and fiddled with his keys. Rachel seemed happy enough to hum along to a tune that was clearly playing in her head.

They walked out into the foyer. Rachel was feeling a little sore but she was glowing with pride at having conquered her fears.

Hank held open the front door. "Thank you." She beamed. "What a gentleman." The irony of this comment wasn't lost on either of them and they both laughed.

"Need a lift?"

"I'm fine my car's parked over the road." She replied sweetly.

"So...will I be seeing you again?" He had to try his luck, what did he have to lose?

"I might see you at the Christmas party I suppose." She shrugged and began to walk away towards her car, then turned and added with a smirk. "Oh and if you are going to buy Aaron a Lamborghini, make it a yellow one. He likes yellow."