Lilly From Tomboy to Horny Slut

This is a tale loosely based on stories my girlfriend told me. Names and places are changed, content exaggerated with blanks filled in by imagination.

Set in early 2000's, a time of drink, drugs and girl power (which in my experience resulted in getting waisted and ladettes being up for a good time...)

All characters within this story are aged 18 or over.

Lillys heart raced as she knocked on the door of chalet 9, at the residential staff section of the Ruffside Hotel. Her bare, smooth legs trembled slight, partly from the chill of the winter night air and partly through anticipation for what she was about to do.

A gruff voice from the room beyond the door called out for her to come in. She turned the handle while telling herself, you've got this, pushed the door open and stepped inside, heals from her cowgirl style boots clicking on the tiled floor while her head was spinning.

Lillys path to this point has not been easy. She grew up in a rough council estate in northern England, in a deprived area with a bad reputation. Lilly had always been a tomboy, raised with 2 older brothers and having a slight, boyish physique. She favoured football and fun fights with the boys to playing with dolls and makeup.

Lilly was a clever, being top of her class both academically and at sports, but remained popular, liked by the boys for being 'one of the lads' and by the girls as she was funny and good crack.

Life started to change when she turned 14. Being smart Lilly spotted signs her dad was cheating on her mother, this culminated when she found a hotel recite and a packet of condoms in his car glove box. She showed these to her mother and a huge fight erupted where it turned out he was having an affair with a woman from work, her parents separated and ultimately divorced.

Through the next year there was a seismic change in Lilly, she barely heard from her dad over this period and he was frosty when they did meet up due to her whistleblowing. Ironically her relationship with her mother, who she called Mental Mary, also suffered, she could tell part of her subconsciously blamed her for how their life was shattered.

During the breakup Mental Mary was frequently out partying, Lilly and her brothers were often left with a free house for long periods at a time.

Inevitable their house became a party house with her older brothers and their friends up to no good in an unsupervised environment. Inevitably this was a bad influence on Lilly and lead to some bad habits.

Life went on like this for a while, being clever she still managed to wing it at school.

Now Lilly was eighteen and a half she had developed into a beautiful young woman.

Standing at 5'4" is fairly average in height but being thin people often called her Little Lilly. She had a pale complexion but with perfect, unblemished, smooth skin, a true English rose. Her natural metabolism and years of sport had given her a stunning, toned body with a shapely tight arse, firm B cup boobs, beautifully pert and accentuated by her thin torso.

Lillys had stunning green eyes that drew you in. Her face somehow had a slightly oriental look. She usually had a cheeky, almost suggestive, glint in her eyes and a cocky smile that attracted attention from both sexes. Her hair was shoulder length and she frequently dyed it different colours as she enjoyed playing with different looks. Currently she was dyed blond with vivid red tips giving her an almost manga look, accentuating her cheeky, naughty spirit.

Up to this point she had sex with 10 guys and absolutely loved to get fucked. She had always felt like an ugly duckling and one of the lads. When she finally got flirty male attention she was easily turned on and eager to please, and please she did...

Her most recent boyfriend was Jay who was 28 and worked as a chef at The Ruffside Hotel. He was 6' tall with a wiry physique from years of working long hot shifts in kitchens and time spent lifting weights to blow off steam. Jay was cocky, his good looks making him a hit with the girls, he'd lost count of how many notches he has on his bed post.

It had been lust at first sight for Lilly and Jay literally bumping into each other on a crowded dance floor at the Loft nightclub. Lilly was wearing a short, tight black dress which showed off the toned legs, she was not warming a bra and her nipples were hard and visible through the thin fabric of the dress as she was hot and flushed from dancing. Jay was carrying 2 plastic shot glasses across the dancefloor to a waiting friend, when Lilly bumped in to him. Watch out love, Jay joked but instead of replying Lilly grabbed a shot out of his had and knocked it back, The fiery sambuca making her already buzzed body flush. You cheeky bitch laughed Jay as he knocked back the remaining drink, you owe me one now. Lilly licked her lips and beckoned him towards her. Without hesitation Jay put both of his arms around her and started to kiss her deeply. They both melted into the kiss oblivious to anyone else in the room, his hands working lower down her back until he had a firm arse cheek in each hand, their bodies pressed tightly together as they moved together in time with the music.

Finally their lips parted and Lilly panted, fuck that was hot, I don't know your name but tonight I am going to be your little fuck toy. Get another round in while I go to the little girls room, then we can go somewhere quite to get to know each other property. Biting her lip she brushed her hand over his now semi-hard cock, winked and sauntered off towards the ladies, his eyes never leaving her perfect arse as her hips rolled seductively.

Jay gave himself a minute to calm down and headed to the bar ordering 6 more shots from Bianca, a 22 year old bar maid. She had a slightly plain face but pornstars' DD tits which were always spilling out of carefully chosen low cut tops when she worked behind the bar.

Looks like your in with slutty Lilly tonight, pouted Bianca as she leaned forward, her big tits swaying hypnotically. Have fun stud and pound the shit out of that little slut but we both know you'll be back with your big hard cock between these tits when you miss fucking a real woman. Jay just winked and laughed, as Bianca blew him a kiss with her plump heavily glossed lips and straightened her peroxide blonde hair behind her ear. He grabbed the drinks and headed over to where his mate Dan sat just off from the dance floor.

You fucking took your time mate, Dan shouted over the loud music, looks like you got distracted you lucky fucker. Jay laughed pusing a shot over to Dan, I'm bang in tonight mate, i just met the sexiest little slut who grabbed my cock and told me she was going to be my personal fuck toy. We're going to have a quick drink when she comes back then I'm taking her back to ours to fuck her raw, don"t hurry back and I'll owe you big time.

Jay and Dan worked in the kitchens together and shared a chalet with the head chef Frankie at the Ruffside Hotel. Frankie was out of town for a few days setting Jay up perfectly for an evening of fun.

No fucking way did a hot chick come on to you and say that Dan called out to Jay but his words choked off as Lilly sauntered up to their table and without a word sat on Jays lap, opposite Dan, shaking her ass against his crotch pretending to try to find purchase.

Who's a girl got to fuck around here to get a drink Lilly joked seductively as she did 2 things at the same time.

She felt like she was in heat tonight, following her naughty encounter on the dance floor with her hot stranger Lilly had decided to take this to the next level. She slipped into a cubicle and started rubbing her tight pussy through the tiny triangle of the black thong she was wearing. She had pampered herself before coming out shaving her little kitty perfectly bare, hoping to find some dirty fun on her night out.

Lilly was soaking wet as she circled her clit through the now clinging panties.

Filled with desire she pulled her panties down kept them in her right hand and started rubbing them against her pussy while slipping 2 fingers inside. Her fingers on her right hand were covered in her juices and her panties were soaked, crunched up in the same hand....

Wiggling her ass on Jays lap Lilly distracted Dan by leaning forward exposing her cleavage, Dan was transfixed as she started tracing the fingers of her left hand suggestively, slowly up and down the glass in front of her while she licked her lips.

At the same time she was distracting Dan she reached behind with her right hand and started rubbing her fingers and previously removed panties over Jays nose and mouth. She slowly rocked on Jays lap which cemented Dans gaze as her boobs bounced before him, her eyes glazing slight as Jay hardened beneath her.

Jay breathed in the unmistakably sweet, musky scent of pussy, he had never been so turned on in his life.

Lilly broke the spell by jumping up, dropping her knickers on Jays lap and downing the shot she had been fingering.

The boys were both shell shocked by the outrageous behaviour but started laughing as they each downed a shot while Jay stuffed Lillys panties into his pocket.

Lilly looked at Jay and said, time to take me home stud, and started to walk to towards the door.

Jay shrugged apologetically at Dan, leaving him with 3 drinks on the table. As he stood to leave he pulled the knickers out of his pocket and threw them over to Dan and left with Lilly.

Out on the street the horny couple were hand in hand and started to head down an alley on a short cut towards the taxi rank.

Jay stumbled and looking down he noticed one of his laces was undone.

Had there pet I need to tie my shoes, Jay crouched as Lilly stopped to spark up a tab.

A naughty idea crossed her mind, she pulled her short dress up over her hips and stepped up to Jay so when he looked up from tying his laces, he was at eye level with her exposed pussy.

She flicked her cigarette and put both hand round the back of his head and pulled him forward, smothering him with her perfect smooth cunt.

You fucking dirty little slut Jay mumbled as his face was rubbed in to Lillys soaking wet slit.

Waves of pleasure were flooding Lilly, she panted, fuck I'm so horny, I love fucking your face like a dirty slut.

The couple had been in a state of lust since they had met, less than an hour earlier.

The thrill of getting caught and the slight breeze was heightening her arousal as he licked her puffy lips, his nose rubbing her clit, face getting wet as he beathed in her intoxicating scent. Without removing his face he altered his position from a crouch to kneeling, this more sturdy stance giving him better balance to bring his hands in to play.

Lilly leaned her shoulders back against the wall as Jays hands travelled up her smooth legs, fingers stroking and teasing her lips apart as his tongue travelled up to her clit. She was in ecstasy as his tongue started circling her now protruding clitoris, Alternating directions as he licked and sucked her erect bud. As she approached her orgasm he started pumping 2 fingers deep into her with his right hand and stroking her arsehole with his left.

This pushed Lilly over the edge, her hips bucking uncontrollably, forcing Jay even tighter against her inflamed sensitive pussy. She lost control panting YES YES YES as a fingertip penetrated her arse. A third finger was added inside her cunt as Jay slightly cupped his right hand, pistoning into her, palm bumping against her mound making a wet slapping noise, his tongue roughly pushing her clit from side to side. She was pulsing with an intensity never before felt and holding her breath, trying to make the feeling last longer. She came hard over him, gushing over his already soaked fingers and face, content and throbbing like she had never felt before.

Lillys hands released Jays head, his fingers slid out of her and grabbing a firm arse cheek in each hand for purchase Jay pulled himself to his feet.

Lilly was biting her lower lip and had a slightly glazed look in her eyes. She put her arms around his waist and pulled him in as she panted, Jesus that was the most intense orgasm i ever had, I am you dirty whore now and you have earned the right to use me however you like whenever you like.

Even in the slightly dim light of the ally Lilly could see the bottom half of his face was glistening from her pussy play. Laughing slightly she purred, looks like you have a little something on your face.

Lilly leaned in and start kissing Jays lips. As she did this, they both breathed in through their noses so they were tasting and smelling the heady scent of her pheromone filled juices that had covered Jays face. This was pure filth and fuelled their animal lust, their kissing became deeper and more urgent, tongues dancing between each other's mouths.

She broke the kiss and started to kiss and lick around his mouth and face, loving the taste of herself on this handsome stranger.

Jays cock was rock hard and straining against his jeans. He still had his hands on her tight arse cheeks and as their lips met again he started rubbing his covered, straining bulge against her still exposed mound.

He brought both hands up, tracing her sides and started to explore her thinly covered boobs.

Lilly broke the kiss and said, here let me help you with that, and pulled the top of her dress down so now all she had covered was her stomach, where the dress was bunched up.

Lillys exposed breasts were a sight to behold, even firmer than usual after cumming moments before, her pale nipples rock hard and inviting. Jay push her tits together started to lick and suck on her nips, fuck, he thought, this girl is perfect.

While Jay was worshiping her tits Lillys hands dropped down, deftly undid his belt, popped his button and tugged down his zip. She turned him around and pushed him back against the wall, squatted down on her heals with her legs wide apart so she was at eye level with his crotch. Lilly pulled his trouser and boxers down in one go and freed Jays stiff cock.

Lilly wasn't a virgin but the sight of his cock gave her butterflies. it must have been a healthy 7" long and a decent girth. Not a porn monster cock but certainly above average in size. The reason she had butterflies was it was perfectly smooth and to her eye beautifully proportioned. His pubic hair was neatly shaved short and she could tell from what little she could see of his body he was obviously toned and took care of himself.

Lilly looked up and lightly held the base of his cock in her dainty right hand with vivid red painted nails. Licking her lips and staring up with her beautiful big green eyes she said, you have a lush big cock, Tonight I want your cum in my mouth and in my pussy. I'm your slut stud.

Maintaining eye contact the whole time she started lightly kissing the head of his bulging cock, getting more turned on by the tangy taste of precum. She spat on his knob and started licking up and down his shaft like an oversized lollypop, tracing round the ridge of his cock head before licking up and down the shaft again.

Needless to say Jay was in heaven as her sloppy tongue and lips worked his shaft and head again and again, looking down at this barely clothed goddess pleasured him like a pro.

Lilly opened her mouth and stated to slide the tip of him in and out of her mouth. She struggled to fit him in her mouth at first due to his girth but his cock got more lubricated with her saliva and her jaw loosened/relaxed allowing 2 then 3" slide in and out, her mouth being used like a pussy. He grabbed a handful of vivid hair either side and encourage her to go deeper but she was choking slightly at 4 to 5". He could feel his orgasm approaching, Lilly noticed this as well and desperately wanting to please him she wanked his cock in and out of her mouth.

He tried to pull out but Liily grabbed his arse, held herself in place and worked his cock with her mouth faster until he shot rope after rope of cum into her.

Although Lilly loved sucking cock and liked the taste of precum she had to admit to herself she did not like the taste of cum. That said she desperately wanted to please this man who had given her the greatest orgasm of her life, so wincing slightly she quickly swallowed the huge load in her mouth like a good slut.

Jay helped Lilly to her feet and pulled up his boxers and jeans as Lilly pulled her dress back up over her boobs and down over her bum.

Now clothed they faced each other and embraced, feeling fulfilled and comfortable in each other's company.

She kissed him softly on the lips and said, nice to meet you I'm Lilly.

It's a pleasure, he replied, I'm Jay.

They both chuckled slightly at the strange formality following their intermate oral exploration of each other. They kissed each other tenderly for a minute, both slightly dishevelled, flushed and smelling of sex. This felt so natural and they each enjoyed the taste as trace fluids mingled in their mouths.

Slightly unsteady on their feet, the couple started down the alley hand in hand, neither of them giving a fuck if anyone had seen their filthy ally fun.

The 2 new fuck buddies made small talk and started to get to know each other as they made their way to the taxi rank and jumped in a cab to make the short trip to Jays place. Sat close together in back seat, each with a hand on the others thigh their anticipation started to rise. He told Lilly he shared the chalet with Dan, who she met tonight and big Frankie, who was the head chef at the Ruffside Hotel. He told her Dan had promised to stay out late to give them some alone time and Frank was out of town for a few days so they would have the place to herself.

Finally they pulled up outside, Jay chucked a tenner at the driver and they entered chalet 9.

Jay pushed Lilly up against the wall in the hall and started to kiss her deeply.

My room is second on the left, he said breaking the kiss, make yourself comfortable while I have a piss and fix us some drinks.

When Jay was done and entered his bedroom holding 2 rum and cokes the sight before him made him catch his breath.

Lilly was lying naked in the centre of his bed, she was smoking a cigarette with her left hand and with her legs spread wide apart her right hand was rubbing her pussy.

Jays mouth dropped at the sight, with the lights on this gorgeous girl looked like a pornstar, fully exposed with a sultry look on her face.

Are you just going to stand there, she moaned, or are you going to come here and use your little cum slut like the filthy whore you've made me.

As Jay set the drinks Lily stubbed out her cigarette and using both hands she spread her pussy lips showing him her beautiful, tight, pink, glistening hole.

Jay pulled his tight top over his head and threw it on the floor. the sight of his defined, solid torso fuelled her arousal. She maneuverer to the edge of the bed as he pulled his jeans down, shuffled them off his feet and kicked them away.

As Jay stood by the bed Lilly rose, bent to pick up her drink and started grinding her naked tight arse against his hard cock which was staining under his boxers. She took a few deep drinks, put her glass back down before straightening, turning and with her arms around him, kissing him with a raw lust which he matched as they rubbed their bodies together.

Without much persuasion she pushed Jay on to the bed and pulled his boxers down, releasing the enticing hard cock she craved.

Jay pulled a pillow under his head so he could easily see this living wet dream toying with him.

He had a large mirror mounted to the wall at the foot of the bed, as Lilly straddled his legs and started to rub her saliva moistened lips all over his twitching, hard cock, her arse was in the air and her face was down in his crotch. The mirror was giving an amazing view of her ass, she had her knees planted either side of his legs so her moist, tight, pink slit and puckered arsehole were framed perfectly.