Jenny's First Spanking

Jenny's First Spanking
It all began on the day before Halloween when Jenny decided to dress up as a ‘naughty schoolgirl’ for the party she was going to with a couple of friends.
She after all still had her old school uniform, the long white socks, big blue knickers, white shirt, the school tie, blazer and that stupid straw hat with the band round it. When she tried it on she was pleased to find that it was still quite a good fit, it was however far from sexy!
So she swapped the just above the knee skirt (the shortest the school would allow) with a very short grey pleated skirt she wore to play tennis. She also swapped the frumpy blue knickers for some skimpy white cotton ones.
Jenny looked at herself in the full length mirror and thought that it was a bit sexier but needed a bit more. She removed her bra and un-tucked her shirt tying it high up her tummy revealing her nice curves and ample cleavage. She decided to add the tie in a scruffy knot which helped draw attention to her lovely breasts. She even added the stupid hat.
Looking at herself in the mirror Jenny could see that her nipples were nicely visible through her shirt, indeed they were a bit erect! She tweaked and stoked them a little until they were fully erect and started to caress her breasts, Jenny was starting to get turned on, as she rubbed her boobs she could feel the nice warm wet feeling grow between her legs. She lifted her short skirt and ran her hand over the fabric of her soft white panties, they were soon soaking wet with her pussy juice as she masturbated whist watching herself in the mirror. She had a nice quick intense orgasm and was still feeling horny and naughty. She had noticed that there were a few stray pubes sticking out from the gusset of her knickers. Jenny thought that would never do for a naughty schoolgirl. So she took off her uniform and ran herself a nice hot bath so she could tidy up her pubic area.
She carefully started to shave her pussy lips until they were pube free and then started to tidy up her triangle, she got a little carried away and ended up with a sort of Brazilian she looked down at it and rubbed at it and wasn’t very happy with the results. So she shaved some more and then some more, soon she was as bald as she was when she was a young prepubescent girl. Jenny looked at her hairless vulva slightly shocked but also slightly amused. She rubbed it gently the smooth feeling was very nice and new.
She got out over the bath and took a bottle of baby oil with her into the bedroom. She stood naked in front of the mirror admiring her handy work and started to apply a bit of the oil to her smooth bald pudenda. It soon popped into Jenny’s head exactly what to do next. She put the bath towel on the bed along with the bottle of baby oil and went to her toy draw and selected her glass g spot toy. She lay down on her back legs wide apart and slowly rubbed the dildo up and down her oily vulva lips. Then with a slight push the big large bulb end stretched her labia wide until it popped into her vagina her lips closing down around the clear shaft. She slid it all the way in and held it there with her left and rubbed the four fingers of her right hand in small circles over her labia just over her sweet spot stimulating her clitoris with out touching it directly.
She felt full with her toy inside her and flushed as her clitoris was getting fully engorged and more and more sensitive, she heard her self moaning Jenny yes Jenny yes ah Jenny please mmm. Her clitoris exploded in a wave of pleasure travelling deep inside her. Her vaginal muscles clenched and unclenched hard on her dildo as her body spasmed in ecstasy.

The next evening Jenny put on her naughty school girl Halloween outfit, she was still feeling very horny when the door bell rang.
It was her friends Annie and Chloe in their Halloween costumes. Annie was dressed as a sluty cop complete with hand cuffs and phallic truncheon. Chloe was in a pink almost transparent fairy outfit that she had expertly made herself. In certain light it was very clear that her very ample gravity defying breasts were braless.
Jenny opened a bottle of wine to get things started and asked Chloe to plait her hair in to school girl pig tails. Whist she did so Jenny could feel Chloe’s ample firm boobs pressing in to her back, god even that was turning her on! She confided to her friends that she would really like to pull a man tonight as she could do with a really good fuck. They all giggled and chatted while they finished the wine and the taxi came to take them to the pub.
It was a cold night and Jenny felt her nipples harden instantly when they got out of the cab which felt as good the cool breeze that blew between her legs caressing her vulva through her thin panties.
As they walked to the bar all three girls were well aware of all the people looking at them, most people hadn’t made much of an effort to dress up.
Before they could order a drink a pretty poor attempt of a ‘ghost’ from a group of guys asked them what they wanted to drink. Jenny went for a Bloody Mary the other two for a Green Snot cocktail, the ghost ordered them doubles and then turned to his mates for their orders, the last voice came from almost behind Jenny and said ‘just a tomato juice I’m driving’
Jenny turned to look at the voice, he was drop dead
gorgeous, his mates were saying go on have another one get a taxi you can afford it, he was shaking his head. When out of nowhere Jenny blurted out ‘Go on have another drink, you might get to spank a naughty school girl later’ she immediately went bright red and a bit flushed in other places too as his mates cheered. Jenny was not quite sure how he did it, but he managed to get his hand up her admittedly short skirt and get a piece of her bottom that her knickers didn’t cover and find a good soft piece of her young pert arse to give gentle but firm pinch.
‘I’m Jim, I hope to take you up on that offer’ Again from out of the blue Jenny cupped her own breasts ‘I I I’m Jenny I I I’m a naught school girl’
Jim smiled and said to ghost ‘Two double Bloody Mary’s’
Annie and Chloe flirted outrageously with the other guys while Jenny found out not to much about Jim apart from he was single and was fifty percent interested in her face and fifty percent interested in her cleavage. The only thing that stopped them ogling each other was Chloe winning the best costume award.
As she received the first prize bottle of ‘champagne’ the lighting changed revealing that it wasn’t just a bra she wasn’t wearing, the whole pub got a good view of her pussy too. She loved it! Chloe loved to show off and had often told Jenny and Annie how she fantasised about guys wanking off while thinking about her. She stood with her legs apart and popped the cork covering breasts and skimpy outfit in wet fizz!
As all the blokes in the pub cheered Jenny plucked up the courage to ask Jim back for a night cap. He didn’t take much persuading.
Jenny poured ample night caps to take upstairs. After a few sips she put her drink down and got on her knees unbuttoned Jim jeans and stroked him to a very hard erection. She then started to suck the tip of his cock, going down gently and sucking hard as she pulled back while cupping his tight balls.
‘You really are a very naughty girl aren’t you?’
‘Um yes I suppose so’ Jenny replied giggling
‘Well there is only one thing to do with naughty school girls isn’t there?’
Jenny thought for a moment or two while slowly wanking his cock.
‘Um I don’t know, was it a spanking?’
‘Yes that right if you remember’
Jim pulled the chair out from Jenny’s dressing table sat down on it and beckoned Jenny to him with his finger.
‘Come here and bend over my knee’
Jenny giggled and did just that, not really knowing what was going to happen next.
Jim lifted up her short skirt and caressed her white panty clad bottom and then pulled them down exposing her naked bottom.
‘What a lovely bottom for a spanking’
Jenny giggled some more, Jim then arranged her so that she was in the perfect position. He ran his right hand up the inside of her thighs, causing her to part them a little, he gently drew a finger up each side of her smooth bald labia majora and then repeated this with one finger feeling the wetness between her smaller lips.
Jenny was feeling very turned on in this new strange situation then…
She heard the load smack land on her bare right bottom cheek before she felt it, just as it stung Smack on her left cheek. Smack on her right Smack on her left.
She heard Jim saying ‘four’
Smack on her right smack on her left
‘Six’
With each smack the sting was less and was replaced by a nice warming feeling, she heard herself not saying Ouch but more like oommmah while she listened to Jim counting the smacks.
He stopped at twelve to run his hand between her legs again finding her warm wet juices seeping from her bald pudenda
‘Thirteen, f******n, fifteen’
Jenny was now so horny she tip toed a bit and got her bottom a bit higher so she could reach her clitoris with her right hand.
‘Sixteen, did I tell you that you could masturbate while I spank you? No I did not!’
Jim gently took hold of her wanking arm and held over the small of her back.
‘I know this is turning you on, do you want to masturbate?’
Jenny replied ‘Yes and I want you to fuck me as well!’
‘Oh my dear you are going to get both, but right now I’m enjoying spanking your lovely bare bottom!’
‘s*******n, eighteen’
The spanks were loader and harder and Jenny’s orgasm frustration was growing.
Smack nineteen whack twenty, twenty one, SMACK twenty two SMACK twenty three SMACK Twenty four those last spanks really hurt.
Now do you want still want to wank?’
‘Please yes’
‘Ok Jenny stand up, you may rub your bottom if you wish’
She did just that feeling the nice warmth of twenty four hard spanks, while Jim moved the full length mirror to the end of the dressing table and put her make up bag in the draw full of her toys (smiling)
All that was left on the table was Jenny’s large oval heavy wooden hairbrush.
‘Take of your shirt Jenny’
She was standing topless with her school tie dangling between her breasts with her panties round her knees rubbing her still skirted sore bottom.
‘Knickers off, skirt off, leave the tie and the socks. Now bend over the table, legs apart, you may lean on one arm, nipples touching the table top. You may use your other hand to masturbate while I spank you until you orgasm’
Jenny did as she was told exited about be bossed around and that she was going to cum soon.
She could see herself and Jim behind her in the mirror. She was a bit unsure when Jim picked up the hairbrush and started rubbing the wood over her buttocks.
‘Do please start masturbating Jenny’
I didn’t take long for her to get in to the stride stroking her clit, with the extra turn on of seeing Jim watching her masturbate.
She watched him undress in the mirror, and his naked body and rock hard penis almost made her cum straight away.
The sight of the hairbrush raised and rushing towards her bottom stopped her on the edge of orgasm, she bit her lip before it struck. SPLAT in the middle of her right cheek, her buttocks clenched her vagina and anus tightened as she let out a strange howl of pain and pleasure.
She looked in the mirror to see the brush raised again, Jim told her ‘That she better keep on wanking as she would be hair brushed until she had had cum’
She also noticed he was gently wanking his cock while he told her that and smiled to herself. Not for long though the second hard spank of the brush landed on her left cheek’
Jenny let out another strange howl of pain and pleasure.
She barely heard him ‘Two’ while her fingers worked at her clit.
Strokes four five and six were each on the same spots and hurt like hell. She lost a bit of concentration and her fingers slowed down a bit.
The next six were on the sides of her bottom with an even coverage. This was more pleasurable, very warm but not to sore.
The next twelve were a different matter though, after rubbing his now pre cum dripping cock along her ass crack he used his left hand to pull up her right buttock to get to the tender part just above the thighs, six hard ones ending near but not on her perineum and the same on her left buttock.
By this time Jenny had tears of pain and joy streaming down her face she was both laughing and crying as she orgasmed.
Jim put the hair brush down and moved round behind her. Jenny felt the tip of his big hard penis against her vulva, she moved her hand from her clitoris to pull her labia apart and with one powerful trust he filled her vagina.
He held her pony tails pulling her head back making her watch in the mirror. He slammed in to vagina slapping the right side of her bottom when each thrust had filled her.
Jenny screamed with pleasure at each thrust and smack. Jim changed hair pulling and buttock slapping hands every few minutes or so, pumping and spanking her hard and fast. Jenny soon felt another strong orgasm build and she came hard, her vagina squeezing Jims cock in waves. Jim however kept on pumping and spanking poor worn out Jenny.
She moved her hand from her sensitive clitoris to cup Jim’s testicles. His balls were tights and firm, Jenny massaged them gently and squeezed them quite tightly.
Jim finally stopped spanking her sore hot bottom and held the top of her hips driving his cock all the way to the top of her vagina. Jenny felt his balls get even tighter as she continued to play with them. She pushed on his perineum with her little finger nearly touching his anus stroking forward to his sack.
She felt him pulse from the bottom of his balls and his cock twitch inside her. She clenched and unclenched her vagina almost sucking out Jims massive ejaculation
While Jim let out aloud groan while squirting his come deep inside Jenny she felt a warm content feeling wash over her.
So that is how Jenny first found out that receiving a good hard spanking could be so much fun!