Abby was an anal virgin – until her boss offered to break her in.
It was a hot day in the office and Abby was at her laptop in the accounts department when she heard the guffaws coming from the other side of the room. She shared the semi open-plan area with two others: John Smart, head of sales, and their boss, Ryan Carter, who oversaw both of them from his own separate office. Intrigued by John’s excitement, she got up and strolled around to take a look.
“Oh my God! John, you’re surfing porn sites?” Brash images of copulating couples shot out towards her in full Johnght colour. One couple on the screen were at it doggy style, the man’s cock thrusting in and out at its full length – and what a length it was. His bollocks were slapping against his co-star’s buttocks as she called out for more. John half-turned his head towards Abby, his eyes still firmly on the action. “It’s not just porn,” he said. “This is Anal Delight. His cock right up her arse and she’s loving every fucking inch!”
“Oh my,” gasped Abby, at a loss as to what to say, “I didn’t realise it was up there.” The camera angle changed and it became obvious then what hole he was penetrating. The heroine’s wet c**t was wide open and her lips flapped about as the bollocks collided with force. Abby was fascinated. She had a good sex life with her husband, Dan, but anal sex was out of the question. It wasn’t her choice; Dan just wouldn’t entertain the idea. She’d once tried inserting a vibrator up there but had found it uncomfortable and given up.
“Ever taken it up the arse, Ali?” asked John, a man of little refinement.
Shocked, Abby heard herself reply, “No, John, I haven’t, but I’ve always wondered what it’d feel like.” She couldn’t believe she’d said that aloud and began to blush. John was about to make her an offer she could refuse when he was interrupted.
“Ahem!” Ryan was out of his office. He’d been hovering behind the pair for some time and had obviously seen and heard everything. Ryan looked at John with his steely grey eyes and said, quietly, “John, my office. Now. And turn that filth off.”
John sheepishly did as he’d been told and followed Ryan, closing the office door behind him. Abby guiltily returned to her own desk and peered surreptitiously over her laptop into Ryan’s office. It was obvious John was getting a bollocking. As John returned to his desk Abby quickly averted her eyes and concentrated on her keyboard.
She was tapping away when John walked up to her. “Fuck me, that was a bit intense,” he said. “He’s sending me home!” Abby began to smirk a little. “Oh, he wants to see you now,” he added, walking abruptly out and slamming the door behind him.
Come Into My Office
Abby’s heart almost stopped. Her mouth went dry and she began to feel nauseous. She rose unsteadily on shaking legs and forced herself to cover the steps to Ryan’s office without falling down.
“Come in, Abby,” said Ryan. “Close the door please. Take a seat.” Abby sat down, her back ramrod straight, and crossed her legs. She couldn’t be described as beautiful, but she was attractive. Her long auburn hair was tied back off her face; a face that had full lips and eyes that were always smiling – although at that moment the smile on her face was a forced one.
“So, Abby, what can I say?” Ryan looked at her and she wondered what she should say in her defence. She studied the floor intensely.
The silence was broken by the last question she’d expected. “So, you wonder what anal sex would be like, do you?” He saw how thrown she was and smiled at her. “I heard what you said out there. Do you really want to try it that much?”
She felt herself redden and struggled to form saliva. “Er, it’s just, Dan’s not into it…” Why the fuck did I say that? she thought to herself.
Ryan placed his elbows on his desk. “You should try it sometime. You might like it.” Her heart raced. “In fact,” he continued, “I could perhaps initiate you into the delights if you felt like it.”
She couldn’t believe her ears. At first she was shocked, but then she realised she was even more intrigued… and was actually considering his offer. “Don’t be alarmed, Ali,” Ryan continued calmly, as though he was discussing a late meeting rather than a sex act. “I’m not suggesting we have an affair, just a bit of ‘breaking-in’, so to speak. John’s buggered off now, so if you fancy taking up my offer, we’re all alone.”
“I don’t know what to say, I really don’t. What about your wife?”
“Sal? She loves it up the arse,” he laughed. Abby couldn’t help herself; she convulsed into laughter too.
I Can Take It
“OK,” she said, “Let’s do it!” Fucking hell! she thought, What am I doing? “What do I have to do?” she asked.
“The first thing is; no talking. This will be an experience you’ll remember for the rest of your life, I promise.” He bolted the outer door and lowered the blinds, bathing them in a cool grey light. He took her by the hand and gently bent her forward over his desk. He reached down and hitched her skirt up over her hips, revealing her panties. He placed a finger on each hip and slowly pulled them down, exposing her toned yet curvy arse. It was as white as her panties and he began to stiffen.
As the panties fell to her feet, Abby stepped out of them. Ryan brought his hand up her thighs, around her buttocks and massaged her slowly, squeezing gently all the time. She felt her juices begin to flow and she moaned a little. Ryan continued the gentle stroking and then with a hand on each buttock he parted them.
Now, she thought, here it comes. A cock up my arse. But she was very pleasantly mistaken. Oh my God, she thought, He’s licking my arsehole!
She knew she was wet but she’d never known just how wet she could get until he prodded his tongue up the tight little hole. She came. It was like pissing! As the first shivers began to die down, she didn’t know if she could even take much more. But having begun, there was no way she was going to stop without popping that cherry.
He suddenly got off his knees and began rubbing her wet arsehole with his fingers. She saw him reach across his desk and pick up a small tin of Vaseline. Fuck me, she thought, He’s well prepared, isn’t he? Ryan rubbed his finger up and down her crack and then slowly he inserted it up her arsehole. She was unprepared for the intrusion and involuntarily forced him out.
“Relax, and try not to force it out.” She relaxed as much as she could and the next time he pushed it up she was able to bear it inside her. Very, very slowly she felt it penetrating further and further, until his other fingers were tight against her buttocks. When it would go no deeper he gently crooked it and stroked her inside. She nearly exploded. His finger went in and out like a tiny piston until she was used to the feeling, and then he retracted it and replaced it swiftly with his thumb while slipping a finger between her lips, brushing her clitoris, and then plunging at least two other fingers up her c**t. She groaned and came again, a gallon of it. She was so taken by the intensity she’d forgotten he was fingering her c**t.
“Please,” she said, “not up there.” He withdrew, continuing to thumb-fuck her arse. Her c**t was her private place. Only Dan was allowed there; letting another man in there was like being unfaithful; being fucked up the arse wasn’t being unfaithful in a strange sort of way.
On-The-Job Training
She was very wet. She concentrated on yet another orgasm when suddenly she felt his fingers pop out. She shivered in anticipation as she felt him grab her buttocks and part them. This is it, she thought. Here it comes, his cock; and it’s going right up my arse. He guided the swollen head, now encased in a condom, onto her and then slowly pushed it inside – inch by inch until he was in her up to his balls. At first she almost forced him back out, such was the shock. But he resisted and she let him go in. It hurt. But the pain was nothing to the excitement she felt. Slowly his cock went deeper up her arsehole; and with each slight thrusting movement she groaned with sheer pleasure. Her entire body was aflame. She could feel his cock penetrating this totally virgin territory, and she spasmed as yet another orgasm began to grip her. She plunged her hand down between her legs and began rubbing her clitoris. It was swollen and incredibly wet. Ryan increased his stroke ratio; his cock went in and out of her in a relentless motion. The faster he fucked her, the faster she fingered herself. It was a festival of fucking as they both powered to a mutual climax.
“Fuck me! Fuck me!” she shouted, her head bobbing up and down as Ryan prodded into her at an astonishing rate. Her entire body erupted. She felt her hair tingle and what seemed like an electric shock trickled down her body to her toes. She’d done it, and it was like nothing else on earth.
Debrief
They both stood there getting their breath back and calming down. Slowly Ryan’s erection subsided and his cock retraced its route up her arse and eventually slipped out. He bent down and pulled up his pants and trousers, passing Abby her panties. She pulled them on and turned to see his face split in two by a huge smile.
“Didn’t you come?” she asked him. “Of course I did,” he said. “Did you enjoy it?”
“Enjoy it? I’ve never come so much in my life. What with you up my arse and me on my clit it was wonderful. I’m still coming. I’m having little orgasms as I think of it.”
He smiled. “I think it’s time you and I went home, don’t you?” Abby kissed him on the cheek and crossed to her desk as Ryan sat at his and tidied up. She sat down and tapped away on her keyboard for a few seconds.
A few metres away she heard Ryan’s laptop beep as it announced incoming mail. Ryan looked at his monitor.
“Same time next week?” he read.
He looked across the office towards Abby. “Yes please,” he mouthed.
