Bridge the Gap Pt. 02

Please read Bridge The Gap first

Tommy Young didn't like Fridays. Friday was the day his mother worked late so he stayed at the school library until it closed at six o'clock.

Ever since the librarian Miss Hughes blackmailed him into performing sexual favours for herself and three of her friends he was always very vary of her.

He was sitting at his usual table finishing off some work for his English examination when Miss Hughes calmly walked over to him, leaned down and in a soft whisper told him that she wanted to see him in her office.

Tommy was stunned as she swiftly walked off, back to her office leaving him to quickly follow her.

'Surely she can't be planning something with me now?' he thought. 'There are people still in the building.'

Tommy knocked and entered her office.

'Close the door please Tommy.' she asked.

He couldn't help feeling nervous but excited at the same time.

As he sat on the chair opposite her desk he waited to see what she wanted.

'Tommy, I have been speaking to my friend Marjory, you remember, the tall lady from my party?'

Tommy didn't interrupt.

'Well,' she continued, 'she would like you to pop round to her house on Saturday afternoon about two o'clock as she has some need of you.'

'I bet she does,' thought Tommy.

'Now before you give me your answer please be aware that I still have the incriminating evidence locked away in my cabinet.'

Tommy's heart sunk. He remembered what an idiot he had been by not erasing his history on one of the library's computers as well as not closing it down. Miss Hughes had copies of the porn sites he had been idly looking at waiting for the library to close.

'So Tommy. What shall I tell her? Will you be able to attend or shall I show those screenshots to the headmaster?'

Tommy didn't need to think. He knew he had no choice.

'I...er...I'll go!' he said quietly.

'Good boy. You know it makes sense!' smirked Miss Hughes.

'Shit!' thought Tommy as he walked home from school. 'I wonder what the old battle axe wants with me?'

It was then that his cock began to stir.

On Saturday afternoon Tommy found himself walking to the address Miss Hughes had written down for him. He was surprised to see it was just one street away from Miss Hughes house and was almost identical in layout and style.

He knocked on the door at precisely two o'clock.

The door opened and Marjory stood glaring down at him.

'In!' she ordered as she stepped aside to let him enter.

'Follow me,' she said as she set off into the house and into her sitting room.

Tommy noticed how she was dressed and how she looked. She certainly was sexier than he remembered.

Her grey hair that last time was in a bun was down, resting on her shoulders. She was wearing bright red lipstick and her teeth were white.

She was wearing a black knee length leather skirt, a cream satin blouse, some sort of dark hose and four inch high heels. She towered over the boy making him feel quite insecure.

'Sit!'

Tommy sat on the sofa while she sat in an armchair and crossed her legs.

Tommy could hear the creak of the leather skirt and the rasp of her hose. His cock grew harder in his shorts.

'No doubt you have some idea why you're here but I thought you might want to know some background as to how.'

She carried on, 'I've known Joan for a long time. I used to be headmistress at a private school for both sexes and Miss Hughes was our librarian.

In those days I was in charge of punishing the miscreants who thought they could be naughty and get away with it. I used to enjoy caning naughty little boys and girls and so did Joan as she watched on to see nothing untoward went on. Obviously for the underage children nothing ever did but for the seniors then it all depended!'

Tommy wondered what she meant.

'What do you mean it depended?' he asked as if on cue.

'Well, Tommy, you see some boys and even some girls enjoyed the caning very much and that became quite obvious when they were told to stand back up straight. Some boys sported an erection and some girls were, shall we say, moist between their thighs.'

'But what did you do?' asked Tommy.

'Joan and I both took a bare red cheek in each hand and applied a type of cooling cream to their bottoms which had the desired affect of inflaming their lust greatly. Then if the boy was still hard we would make him sit on my desk as we both took turns in milking him of his young cum.

If it was a girl and she squirmed beneath our ministrations then either myself or Joan would slide a finger into her tight quim while the other diddled her clit until she came hard on our mature fingers.'

'Unfortunately this had to stop when the UK government put a ban on Corporal punishment in 1986 for state education and then 1998 for private schools.

We were bereft, that is until one day I had to have words with our young English teacher Mrs Jones. She was in her late twenties but her standard of teaching had dropped severely that term whereas previously she was an excellent teacher.

Apparently her husband of five years had come out to her as gay six months previously. She was obviously upset.

I invited her to sit on a sofa I had in my office and sat beside her to console her. She sobbed into my neck as she let it all out. I had my right arm around her and rubbed her shoulders. She seemed to quieten down so I continued to caress her moving my hand to the front of her chest whispering soothing words. She didn't protest and my hand went further down onto her breast. She squirmed nearer to me so my fingers could trace over her nipples. I slid my hand inside of her bra and squeezed them eliciting a moan from her.

She was horny!

Taking this as a sign I moved my left hand up her thigh until I came to her silk panties which I pushed aside and found her sopping wet pussy. She was crying with frustration as I teased her pussy before I rubbed her clit whereby she had an enormous orgasm.

'No Headmistress, please no more. Oh my God!'

She begged me to stop but I just carried on until she had cum twice more.'

Tommy sat there dumbfounded.

'She straightened her clothes and as she was about to leave I told her that if she needed to see me about any other problems just to ask.

It was less than a week later that she was in my office after school begging for more orgasms. It didn't take me long to get her on her knees with her face in my pussy reciprocating the orgasms.

She was surprised one day when Joan was in attendance but soon enjoyed both of us abusing her young body. She even loved Joan fucking her doggy style with her strap-on while she licked my pussy to orgasm.'

Tommy couldn't believe what he was hearing.

'However all good things come to an end when she took up with the gym master and I caught them fucking in her classroom late one afternoon when they thought everyone had gone home. Obviously I should have sacked them but allowed them to resign and move away.'

'But....what...where....how?' Tommy stuttered not knowing how this affected him.

'Well things quietened down for a couple of months before Joan came to me and told me about the Art master who seemed to be paying her a lot of attention. She said he would regularly visit the library on a pretext of looking for ideas for his 'free impressionist' art class by musing over the books in the art section. However he made it his mission to visit Joan whenever he was in. She decided to have a bit of fun with him and wore her skirts shorter and tighter as with her blouses that showed more cleavage when he was in attendance.

We devised a plan to trap him. He was a tall thin man in his mid thirties, not good looking but not that bad either. Joan thought he had submissive tendencies and if you saw his wife you would know why. She was half as tall as he was and about four times more wide. She bullied him by all accounts.

When he came in the next time Joan coyly asked if he could go back to her office after school. He readily agreed so at five past four when the library was closed he knocked on the door. Joan had discarded her suit jacket and had three buttons of her blouse undone. Joan told him to wait in her office while she locked up.

He was sitting on the chair when she came back to her office with his back to her. He was expecting her to sit across from him to discuss why he had been asked to return however Joan walked up to him and placed both hands on his shoulders and leaned into him. He could feel her large breasts pushing into his back.

'You've been a naughty boy, haven't you Mr Simpson? You've been staring at my big breasts for weeks now haven't you?' The verbal teasing went on for a few more minutes until she could see a tent form in his trousers. By now she was squeezing his nipples and causing him to groan.

'Mr Simpson, I want you to fuck me with that big hard cock of yours!' Actually it wasn't that big. It was a bit like him, long and thin.

Soon Joan had him naked and lying between her thighs pumping away at her as she lay fully clothed minus her panties which she'd left at home deliberately.

That is where I came in with my camera and took photographs of him in a very compromising position.

He agreed to go along to Joan's house after school and sometimes in the evenings where we used him as a sex slave.

Joan also took his anal virginity with her strap-on which he loved. Eventually his wife had her suspicions and they moved away.

So Tommy when Joan told me about you I just had to try out your oral skills and today I will try out your fucking ability so come with me!'

Marjory led Tommy upstairs to her bedroom. It was nicely decorated in a feminine way with a large metal frame bed and an en-suite bathroom.

'Strip!' she ordered.

Soon Tommy was naked and on his back on the bed where she proceeded to secure his wrists and ankles to the bed's frame.

She sat on the edge of the bed facing him and crossed her legs. Again his cock jerked with the creaking on her leather skirt and the rasping of her hose. Her skirt raised itself higher so he could see the black suspenders holding up her black stockings. Marjory saw where his eyes were fixed so she thought she would tease him some more by undoing the buttons on her blouse and pulling it open so he could see her luscious breasts pouring over her tight white satin bra.

'Oh God!' thought Tommy. his cock was already leaking pre-cum.

She stood to unbutton her leather skirt and ease the zipper down. The weighty leather skirt fell to the ground allowing Tommy to see her black satin suspender belt that held up her stockings along with her tight shiny black satin panties.

Marjory enjoyed stripping in front of the young boy as she watched his rigid cock bob up and down.

Next she removed her blouse then unfastened her bra and took that off too.

'Fuck!' exclaimed Tommy as her breasts bounced free.

She smiled at Tommy as her fingers slipped into the sides of her panties and she slowly dragged them down her thighs and legs then kicked them off to the side.

He stared at her cleanly shaven pussy. He was sure she had a grey bush the last time he saw her.

Again she sat down facing him and took hold of his cock slowly stroking it.

'Well young man I'm going to straddle you and ride you until I've had sufficient orgasms before I'm finished with you. You will probably cum quickly as I am extremely tight but don't worry, I'll just keep on fucking you until you get hard again.'

Tommy groaned. He knew he was in for one hell of an afternoon.

She straddled his loins and took hold of his cock and rubbed it over her already wet slit.

'Stay still while I feed you into me. I've not had a meaty hard young cock in me for a while.'

The head of his cock slipped in so she rested. The next couple of inches were a lot tighter making Tommy groan.

Marjory was concentrating on mounting the young boy so she pushed herself harder to accommodate him.

'Nearly there little boy!' she said as she dropped the last little bit until her haunches were on his thighs.

'Oh God Marjory!.....'

'No, young man. You will call me Miss Dawson while we're together as well as referring to Joan as Miss Hughes. We own you. Do you understand?'

She started to slowly ride him, sliding her tight hot quim up and down his pole.

'Ye...yes Miss Dawson. I understand!'

'Good now let's fuck!'

By the time Tommy was dressed and ready to leave Marjory had forced three cums out of him and goodness knows how many orgasms for herself.

'Fuck, what have I let myself in for?' thought Tommy as he walked home.

He was to find out on Monday morning when he bumped into Miss Hughes in the school corridor while returning from lunch.

'Tommy, I would like to see you in my office after school today.'

She then walked away to Tommy's amazement.

'Oh shit. I wonder what she wants now?' he thought to himself.

At four o'clock he knocked on her office door and she waved him in.

'Ah Tommy, so glad you could come!'

He knew there was no point in talking so he waited to hear what she had to say.

'We had a four handed Bridge game on Sunday with Marjory, Doris and Edna when Marjory stupidly told everyone what an enjoyable and entertaining afternoon she'd had with you. Doris and Edna were so taken aback that they requested you visit them individually as well. I had to tell them about mine and Marjory's agreement with you but allowed you to visit them at home only one more time. So, young man, you are to see Doris on Wednesday after school. Tell your mother you are involved with some extra curricular activities but you should be home by six o'clock for tea.'

After being handed Doris's address he headed home.

In bed that night he put the address in Google Maps and he found it was midway between the school and his home and only a ten minute walk away.

On Wednesday he knocked on Doris's semi-detached home and waited. He was surprised when a man answered the door.

'You must be Tommy, Doris is expecting you. Hang your school blazer on the coat stand and follow me.'

Tommy followed the man upstairs and into what Tommy guessed was their main bedroom. Just then Doris walked in wearing just a white silk robe.

'I see you've met my husband John. He's going to watch while a fit young stud like you properly fucks me. John sit in that chair and be quiet!'

As John sat in a hard backed chair next to the bed Doris walked up to Tommy and hugged him to her rotund body.

'Take off your shoes then come here and kiss me Tommy!'

Soon Doris's tongue was forcing its way into his mouth as she started to undress him. His school trousers and underwear hit the bedroom floor while she broke the kiss to whip off his socks, then she undid his school tie before taking off his shirt. It was the first time he'd been naked in front of an older man and strangely his cock was rock hard.

'Mmmmm, lovely!' cooed Doris as she stroked it with one hand while the other played with his balls.

She untied the bow on her robe and it slipped from her plump naked body.

Climbing up on the bed on all fours she commanded Tommy to kneel up on the bed behind her.

'I've lubed myself up dear so just slip that lovely hard young cock up my back passage and show my no good, useless husband how to shag me in the arse!'

Tommy looked over at John and saw he was forming a tent in his trousers.

'Don't bother about him dear, just fuck me. You know I love it!'

Tommy slid his cock home and slowly began to fuck her before upping the rhythm and soon he was pounding away at her.

Doris was frigging her clit while talking to her husband.

'He's got a lovely hard dick for a young boy. I bet you never thought you'd see me getting arse fucked by a young lad like Tommy. Oh fuck, John I can feel him sliding it in deep. Oh shit, I'm cumming. I'm.....oh fuck!'

Her arsehole tightened around Tommy's cock and he groaned out loud as he coated her insides as he came hard.

They both lay on the bed getting their breath back. Tommy was hoping he could get dressed and go home as it was the weirdest thing he'd ever done.

'Lie down here Tommy. On your back!' she said as she crawled off the bed. Tommy did as he was requested and waited to see what was going to happen next.

Doris leaned over him and rubbed her large breasts over his face.

'Here, suck on one of my fat nipples.' she ordered as she stuck her large tit right into his mouth and laid on his stomach.

Tommy heard her say, 'John, clean him up with your mouth and get him hard again. I want to ride him with my soaking wet pussy!'

Tommy couldn't move because of Doris's weight and couldn't shout out due to her large breast in his face and her nipple in his mouth.

He could only groan when John started to suck his cock clean. In no time he was back at full mast.

'Time for a ride. Sit back down John. It looks like you enjoyed sucking Tommy's tool, look at your hard on you pervert. Go on, take it out as I ride him.'

Doris slid onto his hard young cock and Tommy was surprised how tight her pussy was.

'Oh yes! That nice. It's been a while since I've had a hard young cock in me. Look at it John. See how wet it is as my juices runs down his pole.'

She kept taunting her husband while fucking Tommy and as he turned his head to look at her husband he could see him frantically wanking his small, thick cock.

Suddenly she pushed Tommy's face down on the bed as he saw John walking towards him, his hand flying up and down his throbbing dick.

'Go on, I know you want to!'

John grunted and let out a leash of cum all over Tommy's face, some of it even went in his mouth. Surprisingly this caused Tommy's cock to explode in Doris's cunt taking her over the edge to an enormous orgasm.

Doris rested on Tommy before licking her husband's cum of his face and swallowing it.

She climbed off Tommy allowing him to slide off the bed where she laid down on her back.

'Get dressed Tommy, John will see you out.'

As Tommy and John were about to leave the room, Doris shouted after them.

'John, don't be too long, there's two holes that need to be cleaned up.'

Outside Tommy couldn't believe what had happened and vowed never to go to their house again.

Tommy's heart dropped when Miss Hughes caught him in the library after school on Friday and handed him a slip of paper with Edna's address on it.

'She is expecting you at one o'clock tomorrow. Make arrangements and tell your mother that you won't be home until after six o'clock. Understood?'

Tommy was aghast. Five hours with Edna? Surely not.

At one o'clock he was standing outside Edna's small terraced house when the door opened and a little voice came from behind the door.

'Come in Tommy. Quick!' was all she said as Tommy hustled through the door. It closed behind him and he saw Edna.

She was wearing a long black silk dressing down that reached down to her ankles. He noticed that she had applied make-up as her lips were bright red and glossy.

'Thank you for coming over Tommy, it is so nice to see you again. Last time was lovely and very sensual but this time I want it to be raunchier. What do you think?'

She undid her gown to reveal a black satin corset that came to just under her perky breasts. It held up a pair of black silk stockings that complimented her shiny black four inch heels.

'Wow!' was all Tommy could say as he gazed at her large erect nipples and then down to her manicured pussy.

'I take it you like my outfit. Follow me and we'll go upstairs.'

Tommy dutifully followed taking in her swaying arse through her silky dressing gown.

'In here, darling.' she said as she opened the door to her bedroom.

Tommy entered then stopped dead as on the end of the bed was another woman.

'This is my sister Enid, Tommy.'

The other lady uncrossed her legs and stood before walking slowly up to Tommy. He took that time to appraise her.