Bridge the Gap

It was Wednesday and Joan Hughes was closing up the library. As the chief librarian it was her job to collect all the books that were lying around and put them back where they belonged and also to check all the computer terminals were closed down so she could turn them off.

Joan was a lady in her late fifties. She had never married and had worked in the library for almost thirty years. She was a large woman. Not fat but curvaceous. Tall with a huge chest and an equally large bottom. She was more handsome than attractive.

She always wore a grey business suit made up of a tight skirt that came down to her knees and a jacket that may have fit a few years previously but bulged in all the right places. A silk or satin blouse completed her outfit along with her ever present string of white pearls around her neck.

Most of the pupils were a little scared of her and she played on this by wearing shiny black high heels that took her height to over six feet. Her hair was constantly done up in a bun to give an even more severe effect.

As she went to check on the terminals she saw that one hadn't been closed down properly.

This wasn't uncommon but she liked to see who had been using it so she could check the ID sign on and rebuke the pupil the next time they came into the library.

'That's not like Tommy Young,' she thought. 'He's always good at closing down.'

She sat at the terminal and was going to set about turning it off when she noticed that he hadn't erased his search history.

'Well, well, well.' thought Joan. 'Tommy really!'

Joan gazed at the sites that Tommy had been browsing. Dominant Mature Women, Mature Female Authority and other mature mistress sites.

Her mind was working over time but by the time she had printed off enough material to convict Tommy a plan had formed.

Eighteen years old Tommy Young was in his last few months of school. He had exams at the end of term and after the school summer holidays he was going away to university. He lived with his widowed mother since his father had been killed in a car accident fourteen years previously. He was five feet six inches tall and slim. His blonde hair tumbled over his bright blue eyes. He was a pretty boy and so was shunned by many of the girls in school..

On Friday most people left the library early except Tommy. After he had gathered his belongings he headed for the door when he heard Miss Hughes call him.

'Tommy, could you pop into the office for a minute please?'

A bewildered Tommy walked over to the Library office and was met by the librarian.

'Please take a seat. I shan't be a minute,' she said.

Joan had a look around the library to make sure everyone else had left then locked the doors before returning. She thought that she could replace the books and sort out the computers later.

She had dressed for the occasion. She wore an under wired push-up bra of black satin and a black satin girdle underneath her trade mark tight grey skirt. She had on a white satin blouse that had three buttons undone showing off her impressive cleavage and shiny grey stockings held up by suspenders attached to the girdle. She had slipped off her jacket just before she called Tommy into the office.

'Tommy, you know it's a rule that every student has log off and close down the computer terminals when they've finished for the day don't you?'

Tommy relieved that was all it was nodded and offered his apologies and told the librarian that he would make sure to do that in future.

'Well Tommy, that's not all. You see not only hadn't you not logged off but you also hadn't cleared your browsing history on Wednesday afternoon.'

Tommy was now in a state of panic trying to remember what he'd been looking at on that day.

'Let me jog your memory,' offered Joan pulling the printed screen shots out of her drawer and spreading them before the nervous young man.

'I er I..I can explain,' he stammered.

'Oh I hope you can. I can only imagine what the Headmaster would say and do. Expulsion would be my guess and so near your exams. You'll probably have to find another school and retake the whole year.' Joan was now really turning the screw.

'Oh God,' moaned Tommy with his head in his hands. 'Whatever am I going to do?'

'You could throw yourself on the Headmaster's mercy or you could...' she trailed off.

'Tommy looked up. 'What? What can I do?' he asked in earnest.

Joan smiled to herself. She had him just where she wanted him.

'You could let me punish you.' she said as a matter of fact.

'Y...you punish me,' how? Asked an astonished Tommy.

'Oh I think we could start with a spanking and take it from there,' replied the mature librarian. 'Or I could just telephone the Headmaster,' she declared picking up the handset.

'No. No, please don't. Ok, I agree for you to punish me,' he begged.

'As I see fit?' she asked.

Tommy looked dejected and beaten.

'Yes, however you see fit,' he agreed.

'Well then. Why don't you start by taking off all your clothes?'

Tommy looked at Miss Hughes who was in no mood to argue with the young man and he slowly began to undress.

He stood before her in his tight white underpants with his hands in front of his crotch to hide his rapidly growing cock.

'I said all your clothes young man!'

With a heavy sigh Tommy peeled down his underwear.

'Hands by your side!' demanded Joan.

When she saw his almost inflated cock she was more than pleased. She guessed he must be about seven inches when fully hard and quite thick.

Tommy knew it was nearer seven and a half as he'd measured it recently.

Joan stood up and raised her skirt to the tops of her thighs before sitting back down again on her chair. If Tommy's cock wasn't fully hard previously the sight of the librarians suspender clasps holding up her fully fashioned stockings made sure it was then.

She told Tommy to bend over her. She positioned him so that his cock was between her thighs which she closed trapping it.

The spanking started mild and sensual. Then it became a little harder. 'Open your legs,' she ordered. This proved difficult for Tommy with his cock trapped by her stocking clad thighs but he managed to prise them apart to satisfy her.

The next series of spankings were to his upper thighs.

The tips of her fingers just catching his balls. This caused Tommy to moan and for his cock to get harder.

She was now alternating her spanks from his thighs to his bottom and back.

'Oh...oh, Miss. Please, no more,' begged Tommy as he could feel his explosion building.

Joan spanked faster and harder until he erupted between her thighs.

'No. Please Miss. Miss pleas...aaarrgghh.'

She pushed him onto the carpeted floor. 'You disgusting little boy! Look what you've done,' she exclaimed.

She opened her legs and pulled him by his hair between them. He could see his goo dripping from her stockings and bare thighs.

'Clean that mess up with your tongue!' she ordered forcing his face up to the sticky cum.

'That's it. Lick it all up.'

Tommy licked and licked until her legs were clean.

'Now! Finish the job. I'm sure you know what to do. After all you've seen enough videos and photographs,' she said as she forced his mouth on her pantyless shaved pussy.

Tommy licked tentatively at her lips before dipping his tongue in as far as it would go.

'Oh God Tommy. You're a natural pussy licker,' she moaned.

This gave him confidence to go further.

He licked and probed with his tongue and when he found her clitoris he thought he'd hit the jackpot. Joan grabbed his head and practically fucked his face until she came hard.

She pushed him onto his back on the carpet then unzipped her skirt and stepped out of it when it hit the floor. She undid the buttons on her satin blouse and slipped it off leaving her standing over Tommy in her black satin bra and black satin girdle along with her stockings and heels.

She wasted no time in crouching down and took Tommy's now hard cock in her hand and fed it to her pussy lips before sinking down on it and riding the young boy to another quick orgasm.

After they had dressed Joan took the screen shots and locked them away in a secure cabinet.

'These are mine and if you don't want the Headmaster to see them I suggest you do what I tell you from now on,' she stated.

Tommy, who was tucking his shirt into his shirt looked at her curiously.

'Do you understand me young man?' she asked.

Realising he was in no position to argue a subdued Tommy whispered 'yes Miss.'

'Good, in that case make sure you are at my house at two thirty on Sunday afternoon. I'm having some friends around for Bridge and I need someone to serve drinks and nibbles,'

Reluctantly Tommy agreed and said he'd be there.

Om Sunday afternoon Tommy walked along to the address Joan had given him wondering if serving drinks and food was all he'd be doing.

He was nervous and excited at the same time.

When Joan opened the door to greet him Tommy wasn't surprised to see Miss Hughes wearing a similar outfit to the ones she wore for work but without the jacket, her hair still in a bun. Tommy thought she looked the epitome of a grandmother. especially as she was wearing a high necked blouse and a knee length tweed skirt.

Joan's high heels clacked on the wooden floor as she took Tommy into the kitchen to show him where the canapes were kept and to where the wine was chilling. She pointed out where the plates and the glasses were before walking closer to him.

'Thank you for coming,' she said sweetly as she put her arms around him and kissed him full on the lips, pulling him into her body.

'Oh my goodness,' she exclaimed at feeling Tommy's hard cock pushing into her.

'It looks like you are going to be a big source of excitement to my ladies,' she said as she stroked his cock over his tight jeans. 'You will do anything they ask. Is that understood?'

Tommy gasped and nodded yes as Joan squeezed his erection.

Suddenly the doorbell rang. 'Go and let my guests in,' Joan said.

When Tommy answered the door a rather plump woman walked in. 'Ah, you must be Tommy,' she said as she hugged the boy.

Hello Doris,' shouted Joan coming out of the kitchen. 'Do take a seat in the living room and I'll get Tommy to fetch you a glass of wine.'

Doris was in her early sixties and was pleasantly rotund, having large breasts and an equally large bottom.

Again the doorbell rang and Tommy went to answer the door.

A tall well endowed lady brushed past him and slipping off her jacket to show off her large breasts in her shiny cream silk blouse she said, 'here boy. hang this up and don't get it creased.'

'Marjory, nice that you could come!' exclaimed Joan as she walked up to her guest and air kissed both cheeks. Marjory was a haughty spinster in her mid sixties. She was tall but attractive with a good figure.

Just then the bell sounded again and with a sigh Tommy once again answered the door. This time it was a petite lady, maybe late fifties, with an elfin face and small breasts. She was not even as tall as Tommy. 'Hello Edna,' said Joan.' Do come in and join the fun.'

Tommy noted that all the women were dressed similarly. Blouses and sensible skirts that looked out of character with their high heels.

Once the women had caught up on their chat they sat down at the card table that had been set up in the dining room.

'Wine for everyone Tommy please,' asked Joan. He obliged and stood waiting for his next order.

'Right. Slightly different rules this afternoon. The person that wins a rubber will take our young man here into the guest bedroom. They'll have fifteen minutes before the game begins again,' stated Joan. Tommy was surprised to hear that.

Doris won the first hand and dragged Tommy to the bedroom.

'Come here young man. Let's see what you have that's making your jeans swell out.' she said as she unfastened his jeans and pushed them to the floor. 'Oh my goodness it looks good enough to eat.

Doris sunk to her knees and took Tommy's cock into her mouth. She slurped on it making him moan with pleasure.

'I bet you'd like to cum?' she asked and Tommy nodded.

'Good boy, then you will,' she said as she bent over the bed and flipped up her skirt to reveal she was naked underneath. 'Slide that lovely big hard cock of yours into my big sexy arse. Don't worry I lubed up before I left. Fuck me boy!'

Tommy was shocked. He'd never done that before but lined his cock in line with her hole and gently probed.

'Go on boy, don't be scared. I'm not an anal virgin. I love it but my husband can't hold an erection these days.'

Tommy pushed hard and he was surprised how easily he slid into her until he was fully sheathed. He began to fuck her slowly building up speed. Doris had her hand on her pussy with two fingers inside and her thumb drumming her clitoris.

'Yes, harder boy. Oh, I'm nearly there. Cum for me young man. Cum inside of me!'

Tommy was on the verge of his own orgasm and hearing the older lady encouraging him he groaned and spurted his seed up her back passage.

Doris let out a muffled scream as her face was buried in a the bedding and came hard collapsing on the bed. Tommy's cock popped out as he gasped for breath still standing as Doris turned over and took his spent cock in her mouth and cleaned him up.

'Pull up your jeans and go back to the dining room. I'll be out when I've straightened up in here.' she said.

'Ah, Tommy!' Joan exclaimed. 'Just in time. Canapes and more wine please.'

Tommy trodded off to the kitchen as Doris returned, a big smile on her face.

Once again the game commenced and Tommy wondered what his next task would be.

'Oh well done Marjory,' someone cried.

Marjory stood and walked past Tommy towards the bedroom. 'Come along boy!'

Once in the room Marjory sat on the end of the bed. 'Kneel,' she ordered.

Tommy knelt at her feet. 'Just where a little pussy boy like you should be!' she exclaimed as she raised her skirt to reveal tan coloured stockings, a white suspender belt and a lack of panties.

Tommy stared at the prominent bush between her legs.

'Come on boy, get your face between my thighs and pleasure me!'

He began his task with trepidation but with the first lick he realised that the older woman's pussy tasted quite nice.

Tommy put all of his recent carnal knowledge into trying to satisfy Marjory. Soon she was writhing on his face, telling him what a naughty boy he was and that she was going to cum. Tommy would ease off and tease her lips before assaulting her clit once more. Marjory couldn't stand it much longer so she held his head tight and his face in place as she rode him to orgasm, her juices squirting onto the young boy's face.

A satisfied Marjory pushed him away. 'Go to the bathroom and wash your face then come back to join us,' she added before pulling her skirt down and returning to the game.

When Tommy returned the other three women were instantly drawn towards the bulge in his tight jeans. 'Oh dear, did Tommy not get to cum?' asked Joan with a giggle.

'Edna, you haven't had the pleasure yet and Tommy looks like he could use some relief, why don't you take him in hand?' Joan prompted.

'Oh, don't you want to play a rubber first. It might be you that gets lucky,' said Edna.

'Oh don't worry about that. I'll have my fun when you three are gone,' added Joan.

Edna rose from the table and took Tommy by the hand and led him towards the bedroom. She hugged him, feeling his cock nudge into her groin. 'Kiss me,' she ordered. He leaned into the older woman and kissed her sensually on the lips. They kissed long and hard as Edna slipped her tongue into Tommy's willing mouth and rubbed herself on his erection.

They broke off the kiss and Edna slowly undressed him. When he was naked she told him to get up on the bed on his back.

She too then undressed. When she was naked Tommy admired her slim and remarkable firm body. He noticed that her pubic hair was nicely trimmed.

She climbed up on the bed and straddled Tommy's waist. He marvelled at her huge nipples that looked even bigger on her small breasts. Leaning towards him she offered them to him.

Tommy eagerly sucked on Edna's nipples causing her to moan and push her breasts further into the young man's face.

'Tommy, I want you to make love to me. I've not been with anyone for over ten years and I don't want you to just fuck me, I want you to make slow, sensual love to me.'

Tommy didn't know what to say. All of the other women here up to now had used him for their own pleasure and now he was going to be able to do it as he liked.

He eased Edna onto her back and kissed her gently on her lips before working his way to her ears and down to her neck. He kissed downwards to her breasts and spent time licking and gently biting her erect nipples causing her to moan gently.

He kissed over her flat stomach and down to her crotch, kissing gently her soft hairy mound. His mouth slipped onto her pussy where he kissed her lips and used his tongue to part them. Edna was in dreamland as Tommy's tongue flicked against her clitoris. 'Oh God Tommy, I..I'm going to cum.'

With a scream she came all over the boy's face. Not letting Edna recover he slid up her body and eased his throbbing cock into her tight wet pussy.

Edna gasped as Tommy slowly fucked her. 'Yes, yes, yes,' she chanted as he plowed into her.

He could feel her hips responding to his strokes so he increased the speed of his thrusts. Suddenly Edna's legs wrapped themselves around his back and her arms locked behind his neck. 'Oh fuck me Tommy,' she pleaded.

Tommy was on the verge of coming himself and when Edna cried out once more and her pussy tightened once more in orgasm he came hard inside her.

'Oh Tommy that was just out of this world. Thank you,' she said. 'You must get dressed and get back while I sort myself out.'

Tommy returned to the dining room where the other three ladies were drinking the remains of their wine.

When Edna appeared Joan suggested that they retire to the sitting room for coffee. Half an hour later the three ladies were on their way and Tommy was alone with the mature librarian.

'Time for my fun I think,' she said to a concerned Tommy. 'Follow me!'

He followed her to her own bedroom where he was told to undress.

When he was naked he was forced onto the bed on his back and his wrists and ankles were tied to the iron bedposts by silk scarves that he had failed to notice.

'I won't be long,' said Joan as she disappeared into her en-suite bathroom.

Ten minutes later she appeared and the sight caused Tommy to gasp. Joan was wearing a shiny black leather bra with a pair of black leather open crotch panties, shiny black hold up stockings and four inch heel shoes, also in black.

Around her neck she wore a black leather choker and on her hands she wore shiny elbow length black kid leather gloves. Her grey hair fell over her shoulders and she was wearing bright red lipstick. In her hand she carried a riding crop.

'Well young boy. It looks like I'm the one in charge,' she said as she flicked her crop along the side of Tommy's hard cock causing him to groan. She began to stroke the crop up and down the length of his cock as she told him what she expected.

'We have two hours before you have to go home and in that time I expect, no, demand many pleasurable orgasms. When I say lick my pussy you will do so. If I tell you to stick your tongue in my arse I expect it done without complaint. If you don't do as I tell you I will turn you over and use this on your bottom. Do you understand?'

Tommy could only nod.

Joan threw down the crop and mounted his face. 'You know what to do!'

For the next two hours Tommy licked and sucked every inch of the older woman's body. She rode him to orgasm and he fucked her doggy style and in the missionary position until she'd had another three orgasms. He had cum twice himself and was pounding into her with her stocking clad legs wrapped around his back as she urged him to cum in her one last time.