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Tara gets Jail - and a Sexual Awakening! Part One

Tags: lesbian, ff, otk, prison
Life behind bars in a women’s prison – Tara’s fall has a silver lining.
Tara sat in complete silence on the edge of the small iron bed, its mattress thin and covered in a sort of plastic type material with a sheet and dull green duvet. She jumped with a start when the heavy door slammed shut leaving just her and another girl sitting on the opposite bed staring at her each other.

‘What are you in for?’ the girl said breaking the quiet, although it was far from quiet, outside in the vast hall and communal area was the hum of activity, footsteps and voices from other prisoners going about their boring daily routine.

‘Dangerous driving,’ Tara whispered, still unable to comprehend how she had come to be in such a terrible place. ‘You?’

‘Burglary,’ she said casually. Tara looked incredulous at the girl, probably about twenty but as small as a schoolgirl. ‘I know what you are thinking,’ she said pointing at herself, ‘it’s because I am so small I can get through the tiniest cracks. Got good at it until they caught me and now I’m here for two years. How long did you get?’

‘A year,’ Tara said ruefully, ‘but my solicitor said I could be out in six months.’

‘Yeah, right, if you behave yourself, keep out of trouble and obey the mistress.’

Tara was just about to ask about the ‘mistress’ when the door lock clicked loudly then opened wide. A tall woman of about thirty with a shock of curly blonde hair stood briefly in the doorway, she was slim and dressed neatly in a tight black skirt and jacket fastened by silver buttons, epilates adorning the shoulders with a small crown and a number.

The warder entered the small cell, towering over us both but her eyes firmly fixed on the other girl. ‘Stand up Becky,’ she barked and the girl jumped to her feet. The warder must have been close to six foot against Becky’s barely five, made even worse by their differing footwear, the woman’s fairly high heels against trainers. Becky wore jogging bottoms with a pink t-shirt, her brown hair in a simple ponytail, no make-up but still very pretty Tara thought, she reckoned she was probably just a couple of years younger than her twenty-two.

‘You were fighting with Cherry at dinner I take it?’ She asked sternly. Becky nodded. ‘You know the rules.’ Becky nodded again.

The warder sat in the spot vacated by the girl and crossed her legs, long and shapely and sheathed in black tights, one stiletto firmly on the floor the other flicking back and forth on the end of the toes on her crossed leg.

‘You know what to do,’ she said evenly, tapping her skirt with long fingers. Becky didn’t hesitate and pulled down her jogging pants letting them drop to her feet then moved closer to the warder’s side. ‘And those,’ she barked looking directly at the front of Becky’s skimpy pink knickers.

‘Please ma’am,’ she pleaded, ‘not my pants.’

‘Would you prefer loss of privileges?’

Becky didn’t answer but fingered the elastic waistband, drawing them down her legs to her knees. Tara was mesmerised at the sight unfolding before her.

‘Over my knee girl,’ the warder said her eyes not moving from the wispy triangle of pussy fur now on view. Becky moved to her side and bent over, her arms stretching for the floor as her head sank downwards, the ponytail conforming to gravity and swinging forward.

The warder wasted no time, her long hand swatting the peachy orbs now dancing on her lap, Tara watched in stupefied fascination as they turned gently pink then red then crimson and then it was all over. Becky was back on her feet with both hands smoothing up and down over her spanked cheeks, her breathing rapid, breasts moving animatedly beneath the t-shirt with the rhythm of her hands.

The warder got to her feet, smoothed down the front of her skirt then left along with the clicks of her heels. The door banged shut.

‘What the heck was that all about,’ Tara squealed as she watched Becky wriggle her knickers back into place before doing the same with her joggers.

‘That was the mistress, Miss Flinton to be exact. If you want to be out in six months you had better get ready for the same.’

‘You’re joking, can she do that?’

‘Of course, who is going to stop her? You do have a choice, take her punishment or stay in here longer. My advice is to pull down your pants and get over her knee when she tells you to. I’m Becky by the way.’

‘Tara,’ she responded forcing a smile. She was indignant yet something was stirring inside. Was it the sight of a woman getting spanked by another woman or was it Becky’s little wispy patch that had fired her up, whatever it was her nipples strained against her bra.


This was all so different from her life up to just a few weeks ago. Tara was important, well she certainly felt so and as PA to Max, her multi-millionaire businessman employer she was at the heart of his empire. She jetted around the globe with him, sat in boardrooms making notes and controlled who got to see him. He was handsome but much older than her but despite the tittle-tattle there was nothing sexual between them. Tara sort of fancied him but never got that ‘must have’ feeling even in posh hotels, just the two of them after dinner. All they had in common was work and Max had never made a move on her and she hadn’t encouraged it.

She had not had sex with a man for the best part of two years, not having had the inclination despite the offers and availability of good looking guys, so work was her life and she was good at it but something was missing. Probably that was her downfall, too much wine when off duty and in the company of her girlfriends, mostly married and all in some kind of relationship with men so that’s where the talk usually got too. Tara got teased about having no guy in her life but she was happy, or at least thought so, and after a bottle or so of Chardonnay things always seem much more normal.

The magistrate had banned her for a year after getting breathalysed for jumping a red light. She was mortified but failed to tell anyone, how could she? Driving was part of her job so she decided to ignore it and carry on as usual, no tax and no insurance but who would know. Then came the incident where she mounted the kerb and almost flattened a woman with a pushchair, hitting a lamppost and wrecking her car. Over the limit again and driving whilst banned, almost running down a woman and child saw the book being thrown at her.

Tara stood in the dock in her finest business suit and Christian Louboutin shoes but it was no use and she quaked as the woman judge summed up her feelings about her actions, finally declaring that a prison sentence was the only option. She had nearly fainted when in a superior voice the woman pronounced her fate with one year in jail, basically declaring her job null and void, her company car gone and handing back the keys to her glitzy apartment. When she got out she knew she would be lucky to get a job as a waitress!


Tara pulled herself back from the traumatic memories of the last few weeks and once again eyed the young girl sitting opposite her, now shifting around on her obviously sore bottom with one hand up the front of her t-shirt.

‘God, that bitch really warmed me up,’ she husked, her hand feverishly fondling one nipple before moving to the other and back again. ‘Oh fuck this,’ she said suddenly whisking the top over her head and throwing it to the bed, both hands clamped to her fairly ample breasts.

‘You can’t have enjoyed it,’ Tara’s face was incredulous.

‘You wait ‘till you get yours,’ she breathed, her excitement palpable.

‘You have to be joking,’ Tara said indignantly, ‘I won’t let her do that to me!’

‘Then you’ll be here for a whole year,’ Becky said still rubbing her swollen nipples, ‘and you won’t know what you are missing.’

Tara blushed at the thought. Becky’s hand had now arrived between her legs, spread wide, her fingers smoothing over the fabric of her joggers. Then she got up and delved in a small drawer by her bed fishing out a flat-backed wooden hairbrush, her hand stroking the shiny surface almost lovingly.

‘I had hoped she would use this on me,’ she said, almost ruefully, ‘I really needed a good dose,’ then turning towards Tara, ‘would you use it on me?’

‘You’re kidding, right?’

‘Please Tara, I can’t ask anyone else can I?’ Becky moaned. ‘Besides, you look like a woman used to being in charge, I’m right aren’t I?’

‘I was but not anymore,’ Tara said sadly.

‘Please Tara, you’re my cellmate, we look after each other, that’s how it works.’

‘And whacking you with that is looking after you?’

‘There aren’t many pleasures in here,’ Becky said moving right up to Tara’s side, pressing herself against the still seated woman before offering her the hairbrush.

Tara’s nose wrinkled at Becky’s scent, mostly jasmine and slightly musky. She wasn’t used to being so close to another woman, her body pressed against her arm and shoulder, it felt strange yet somehow appealing. ‘What do you want me to do?’ she relented.

Becky wasted no time and pulled her jogging pants down before quickly hooking up her knickers and yanking them to her knees. Tara ogled the wispy golden patch nestling at the curve of her tummy before tearing herself away, staring at her breasts heaving with excitement before looking directly at the girl.

‘You didn’t want Miss Flinton to take your pants down,’ she recalled.

‘Of course I did, that was part of the game, playing hard to get, I thought it might earn me a few swats of this,’ she explained offering Tara the brush. ‘Give me six, three on each side and don’t hold back.’

‘What if she comes back?’

‘She won’t, its lights out in about five minutes so no one will come until morning, besides she’s probably busy giving the other girl a good spanking.’

Becky promptly bent over Tara’s knee. This was a completely unexpected and strange experience for Tara who sat mesmerised at Becky’s upturned bottom lying on her lap her pinky-red cheeks nicely rounded and quivering with expectation. She spun the hairbrush in her hand and presented the flat side to the girl’s left cheek which suddenly tensed at the light touch. Gripping her around the waist she pulled back and swatted it firmly on her bottom.

‘Ooooh! Miss,’ Becky squeaked. Tara spanked her again on the other side and Becky responded with another squeak, two red blotches appeared replacing the pinky-red, wobbling sensuously. The sound was quite loud, echoing around the almost featureless little room and Tara looked nervously towards the door but heard nothing.

She gave her two more swats, one each side and Becky’s legs began to kick up, a contented moan coming from the girl, the oval fruit of her entrance appearing to swell between the tops of her legs. Tara suddenly felt her own pussy tingle at the sight; she had never seen another woman in such a way and certainly not another woman’s intimate bits, she was aroused there was no doubting that!

‘SMACK!!! ... SMACK!!!’ She dealt the last two spanks with extra confidence and Becky responded with a couple of high-kicks from Tara’s lap. She struggled off Tara’s knee and rubbed her bottom gingerly.

‘I knew you would give me a good spanking,’ she said breathlessly, her face flushed after bending. ‘God that was so horny.’ Tara handed back her hairbrush.

Becky threw herself on her bed and immediately inserted the handle of the brush into her, sliding it back and forth inside her pussy her knickers and pants still snagged around her ankles. Tara was spellbound, staring intently then the lights went out.

‘I can’t believe you actually enjoyed me doing that to you,’ Tara said in the darkness, Becky responded in ecstatic moans as she continued fucking herself with the brush handle.

‘You’ll see,’ she panted at last.

Tara stripped for bed, aware of her own arousal, feeling hot and confused. She decided to sleep naked.

No way was she going to sleep, her head was spinning with the images of Becky bending over the warder’s knee, then pulling her knickers down in front of her and bending over her knee, the view of her pouting entrance, the smell of her perfume, her hand fondled the delicate folds of her pussy.

‘Can I come in your bed, Tara?’ the little voice said in the dark, the duvet moved and Becky’s slender body slithered in beside her without waiting for an answer. Tara tensed at the unexpected intrusion but allowed her in, that heady perfume once again invading her senses.

Becky was naked, they both were and neither could keep their hands still. Tara slid hers over the flat stomach beside her, gently rising towards Becky’s breasts, cupping her mound, savouring its smooth softness, the first time she had ever felt another girl’s boobs. The nipple was hard and erect and her slim fingers explored it gently, feeling its rim before moving to the other one, testing it between thumb and forefinger. Her own were as erect, chafing against the rough fabric of the duvet, Becky moaned and stiffened beside her.

Now it was Tara who stiffened, the feel of Becky’s fingertips stroking the dark patch of pussy fur, back and forth, along her tummy then back even lower, just above her love-lips, she had to get off her back, onto her side facing the younger woman. Pulling the duvet down Tara moved in on Becky’s breasts, nuzzling her lips against the hard nub before sucking it into her mouth, her tongue playing the tip of the girl’s nipple.

‘Aaaah! ... Aaaaaahhh!’ Tara squealed as Becky’s finger finally found her clit, sliding along her labia then back onto the sensitive ‘love-button’, she could feel the juices forming in her pussy, sucking Becky’s nipple hard. Becky gave out a low moan as Tara moved to her other breast, squealing involuntarily when her fingers probed between her legs. She was already hot and wet, aroused by the handle of her hairbrush but the warm touch of Tara’s fingers livened her pussy, gyrating her hips, her still stinging bottom writhing against the harsh mattress.

Becky had entered her, two if not three fingers deep inside her wet pussy, tingling every part of her, the ecstasy radiating through her entire body. No man had ever made her feel like this, she could barely remember what it had been like, it had been so long, but nothing had ever felt like this, the sensations were rippling out from her pussy like radio waves. If she had experienced anything like this before she would surely have remembered it.

She was riding Becky’s fingers, plunging her own into the girl, feeling her tighten around them as she found her tender spot, soft wet lips engulfing the summit of her left breast before moving to the other. No one had sucked her nipples before, not even a man and the sensation was almost unbearable, surely they would ripen and burst anytime now!

The bed was alive with activity, both women riding the probing fingers of the other, lips now pressed together in a long endless kiss, eager tongues flicking between the two, Tara’s other hand cupping Becky’s still hot bottom, so effectively spanked with the hairbrush.

Becky’s breasts pressed hard against Tara’s, the sensitivity of both heightened to a crescendo and only eclipsed when their nipples brushed against each others’. Tara ached for Becky’s mouth to suckle them once more, equally yearning for her to tantalise her pussy with her tongue but it was still firmly inside her mouth as the long kiss continued.

Becky’s hot spanked bottom pushed against Tara’s hand animatedly as she ground against her other hand, fingers hard and unyielding against the walls of her pussy as she flooded them with her juice. The girl shrieked with her final contraction then Tara let go against Becky’s searching hand, her head spinning as if on drugs, the dark cell suddenly bathed in light.

Becky was still only half out of the bed when the heavy bolt clanged and the door swung open. Miss Flinton framed the doorway and saw all she needed to see.

‘I will deal with the pair of you in the morning. Get some rest because you will both be standing all day tomorrow, sitting down will not be an option.’

The door clanged shut and the lights flicked out. ‘Sorry Tara,’ came the small voice,’ I must have made too much noise.’

‘Me too,’ Tara soothed. ‘Do you think she will use the hairbrush on us?’

‘I’m afraid so,’ Becky answered, ‘and I reckon it will be more than just six.’

‘Hmmmm! Do you think we should do this again afterwards?’

‘The old witch said we wouldn’t be able to sit down, didn’t say anything about lying down!’

‘Sweet dreams Becky.’

‘Sweet dreams Tara.’

Part 2 – Tara feels Miss Flinton’s hairbrush, and much more besides!

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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