2: Anal Annie and Her Amazing Anus.
"THE LUBE, MR BAXTER," yelped Annie in alarm, "USE MORE LUBE!!"
The young woman grabbed the white pillow at each end, scrunched it up, and buried her grimacing face into it as she felt the man wriggling around above and behind her searching for the plastic bottle of green goo.
Good grief. This is ridiculous. That thing was never going to fit inside her bum no matter how hard they both tried to force it in. Her client's equipment certainly gave "taking a fat cock up the old poopsie" a whole new meaning. Annie winced as she felt his stubby erection flop out from her widely stretched outer ring with an audible "POP" that made her gasp and giggle in equal measure. He had managed to penetrate her only an inch at most as her rubbery sphincter held firm.
She twisted her head and looked over her shoulder as the rather rotund gentleman staggered around the motel room looking like a drunken marshmallow.
"Mr. Baxter," she sighed, "It's over THERE."
She pointed to the wash basin hanging lopsided from the far wall under a stained mirror that could probably tell a tale or two. The room was as basic as they came with very little in the way of creature comforts. No wonder it was cheap.
Turning over on the bed, she gave a surprised squeak as she eased her sore backside back down onto the mattress. God. Her poor bottom throbbed painfully in more ways than one. First, because of her well strapped and spanked cheeks and, second, because of their frustrating attempts to bugger her bumhole.
Mr. Baxter returned looking slightly frazzled as he stood next to the bed giving the bottle of lube another shake. The man was in his early fifties and had obviously "made merry with the pies and sherry" over the years. He was wheezing like an old steam train as he stood there in his black socks and nothing else. "Sorry," he muttered as he ran his hand through his thinning gray hair, "Are you alright?" he asked concerned.
He grabbed his stiff pecker and gave it a shake, "This thing has always been a pain in the arse. No pun intended. My late wife used to slap me silly whenever I tried it on with her. "God gave me one hole and one hole only for that sort of thing!" she always used to tell me. You should have seen her face on our wedding night when I dropped my underpants and showed it to her for the first time. I'm still surprised she didn't run to her mothers screaming blue bloody murder," he sighed, looking crestfallen at the memory.
Annie smiled and tried not to laugh. She felt kind of sorry for him as he was a decent bloke by all accounts. She scooted to the bottom of the bed and took his six-inch penis from him. "Listen, Stanley," she said, looking up at him as he stood before her twiddling his thumbs, "I don't mind getting shagged up my arsehole, okay?"
She waggled his member back and forth with her fingers nowhere near encompassing his comical girth, "But this thing. This thing is as fat as it is long. It's like trying to push a can of Tizer up my bum. I think I can take it but you just need to be careful and take your time. And use MORE LUBE for Christ sake!!"
*
Everything starts somewhere.
Autumn was on her way out with the dull gloom of a late afternoon downpour soaking the great metropolis of London as nineteen-year-old Annie Jones made her way home from the local college where she was studying for her secretarial diploma. The rain began to fall harder as she skipped between people and puddles as she pulled her coat tighter around her. Her long brown hair was soaked and stuck to her head as she reached up to wipe the water from her face. A face with wide blue eyes, firm nose, and rosebud lips. A pixie face as her mother often told her. Naughty but nice.
"Shit, shit, SHIT!" she muttered to herself as she saw her bus pulling into her stop. "Don't you dare leave without me!!" she cursed as she started to run. But there was enough time. She skidded to a halt and stood gasping behind the line of passengers waiting to get on. She gave herself a quick shake and did a little dance on the spot as the conductor helped her onto the bus.
"Hurry up, Luv!" the older woman urged, "Get yourself upstairs. More room up there. I'll be up in a tick to give you your ticket. Eeeh, what a horrible day."
Annie blew her nose as she climbed the stairs to the upper deck and made her way to the back seats where she dropped her wet bag and flopped down exhausted before trying to brush the water off her coat. The first thing she was going to do when she got home was to have a hot bath to ease her aches. She used her hand to wipe the condensation from the window next to her and watched as the rain swept streets of London faded away into the gloom as the bus pulled out from the stop.
She sat back and let her mind wander as the motion of the bus helped ease the stress of the day. She was about to close her eyes when something caught her attention on the seat in front of her.
It was a newspaper. Well, at least it looked like a newspaper. Annie sat up and frowned. Except it wasn't the sort of newspaper you'd buy in your local newsagent or store.
Annie glanced towards the front of the bus. There were only two other passengers sat on the upper deck with her and they were both in their own little worlds. She inched further forward and reached over the back of the seat and gingerly picked the newspaper up. She quickly resumed her seat and huddled down so no one could see what she was doing.
In that moment, her world changed.
The life that she lived and thought she knew would soon become something much more vital and alive. Annie gasped as she looked at the front page where a rather bosomy lady sat naked with two huge stars covering and censoring her splendid bust and imagined nipples. "More of Titanic Tessa and her Tremendous Tits INSIDE: page 3" said the headline.
Annie Jones had just discovered the latest issue of Adult Monthly News.
*
"So how did you find out about the Spanking Agency?" asked Molly as she sat behind her desk interviewing the young woman before her, "Can I call you Annie?"
Annie nodded. "Well, it's kind of like this, "she began as she retold the story of how she found that newspaper on her way home from College, "And I sort of smuggled it upstairs to my bedroom where I could read it in peace. Don't get me wrong, my mom and dad are great but they're your typical suburban mom and dad. There are rules. And rules about rules." she laughed. That was true enough. They gave her enough rope to swing but not enough to hang herself. In by ten meant in by ten. Her love life was ruled by the clock.
That love life had revolved around a couple of sort of serious boyfriends and the odd brief fling from College. The first, Simon, had been her first proper boyfriend and had, after the initial excitement, turned into a disappointing affair. They had both been reluctant virgins and the taking of either prize had been a nervous and tense coupling one Friday evening in her bedroom when her parents had gone to visit an elderly Aunt. The feel and sensation of an impatient condomed cock in her pussy hadn't exactly been the earth shattering event she thought it would be. Further fucking and sucking improved their technique but she had always felt that something was missing. Their three-month relationship inevitably faded away and died on the vine as they both realized it wasn't meant to be.
Her second boyfriend was a more intense experience for one particular reason. He was a long-haired rocker called Dougie who always wore a leather biker jacket and chewed a toothpick to make himself look sophisticated. He was the kind of guy who talked a good game but rarely delivered on the promise. Sex with him had been a sweaty fumbling thirty-second thrill ride without the thrill. She was amazed they had lasted two months. But there was one thing he was into that switched on the light in her head. He wanted to do her up her bottom.
"You what?" she had spluttered wide eyed as they sat naked on his single bed. They were in his rented first-floor bedsit with its faded wallpaper and black and white tv in the corner. God knows what his landlady thought below them when the brass bed began to squeak like a demented mouse as they fucked themselves this way and that.
Dougie took a long drag of his rolled ciggie before dropping it back into the ashtray which was on a table next to the bed. "Up the crapper, sweetheart," he drawled, "Ain't you done it like that before?"
Annie shook her head. No, she had not! Though she did know it was a thing. She wasn't that innocent. Did she want to try it? She glanced down at his medium sized cock. Could she take that thing up her rear end?
"Is that what you want me to do?" she asked hesitantly. Shafting her pussy was one thing but rogering her poop chute was quite the other. She could feel her tight hole twitching at the thought. She always did say she'd try anything once though.
Dougie rolled off the bed and went to the small bathroom where he opened a mirrored cupboard above the sink and took out a jar.
"What's that?" asked Annie as he came back and sat on the bed beside her.
He unscrewed the lid, dipped in his finger and pulled out a gloop of goo on the end of it. "Vaseline, Luv," he said, showing it to her, "Rub a wedge of this on your arsehole and suck my knob for a bit to get my todger nice and wet and, bingo, we're good to go. Might hurt at first but you'll love it. Promise."
Uh huh. Sure. Pull the other one. Annie frowned at him as he held the jar up for her.
"C'mon," Dougie urged, "First time for everything."
Annie stuck her tongue in her cheek and carefully scooped out a large dollop of lube and rolled onto her hands and knees. Reaching between her legs, she probed and prodded around her anus as she smeared her pooper making sure it was well greased up for its first penetration as her boyfriend presented his slim Whitman to her mouth.
Once she had lathered him up with her spit, he stepped awkwardly around her as she knelt there and got himself into position. A little adjustment of his hips, then she felt him press the head of his member against her nervous bumhole.
"Ready?" he asked.
Anne dropped her head and buried her face in a pillow. Oh shit. What the hell was she doing? This was probably going to hurt a whole lot and would sting for a month of Sundays. Maybe she should just tell him to roll on another condom and shag her up her cunt again. She was absolutely positive she was going to hate doing it this way.
Up her arse.
She mumbled a muffled, "Okay, go on then. But be fucking careful!"
To her complete surprise, she eventually discovered she absolutely positively LOVED anal sex.
*
