The Reluctant Virgin

Barbara Mason had smoothed down her black pencil skirt and straightened the seams on her shiny black silk stockings when the telephone rang.

She reached over to her bedside table and took the phone out of its cradle before answering it.

'Hello?'

'Hello darling,' a posh voice purred.

'Oh, Hi Audrey.'

'Are you ready for him?'

'Yes I just have to put on my heels and I'll be ready.'

'Do you think he's what we've been looking for?'

'Well he does seem eager and shy but the best thing is I'm sure he's submissive.' replied Mrs Mason.

Audrey Chartwell was a tall, slim, fifty two year old widow.

She was a very attractive woman and like Barbara Mason and their other friend Celia Harrison she was fed up of guys hitting on them then disappearing out of their lives once they'd had what they wanted..

She was wealthy in her own right after a profitable divorce and had more recently been widowed, her late wealthy husband dying of a heart attack. She lived in a large detached house about a quarter of a mile from Barbara.

All three ladies had drawn up a list of attributes they required from a male partner.

The list wasn't long but all three had included two requirements which was that they had to be young and submissive. So far they hadn't been successful in seducing anyone like that until Barbara had found Peter.

Back at Barbara Mason's house she had just slipped into her four inch classy shiny black heels when the doorbell rang.

After looking in the hall mirror to check on her appearance she opened the door.

'Peter, so glad you could make it. Please come in.'

After she'd closed and locked the door she told Pete to follow her into the sitting room.

Pete got a good look at what she was wearing and noted she was in all black. Black silk blouse, tight black pencil skirt with her curly blonde hair placed up in a bun. Black stockings and shiny black heels.

She took a seat in the centre of the sofa while Pete looked around for somewhere to sit. As he made his way to an armchair she ordered him to stop.

She crossed her legs and Pete heard the whisper of her stockings as they rasped together.

'So Peter, come and stand in front of me and tell me what you remember about your last visit here?'

An embarrassed Pete looked down at the lounge carpet and muttered something incoherent.

'Come along Peter. Surely you remember? It was only two days ago. You must remember losing your virginity don't you?'

'Ye...yes. I do. And it was lovely,' he added blushingly.

Mrs Mason smiled and uncrossed her legs.

'Peter why don't you kneel down.'

As he knelt Mrs Mason opened her legs to show off the tops of her silky black stockings held up by black suspenders and her shaven wet pussy.

'Peter, come and show me what you learned last time. Use your mouth on me and make me cum!'

Pete shuffled over to Mrs Mason but before he could dip his head she grabbed the back of his hair and looked him in the eye.

'You will be a good boy for Mummy today won't you?'

Pete nodded and felt his cock grow hard just before Mrs Mason dragged his face between her thighs.

'Oh fuck yes!' she cried as Pete's mouth enveloped her cunt.

Pete put into practice everything he had learned the other day quickly bringing Mrs Mason to a screaming orgasm.

'Wow!' was all she could say as Pete emerged from beneath her skirt, his face glistening with her juices.

She looked down at Pete, still on his haunches, and smiled at him then she stood up.

'Come along it's time we went upstairs.'

In the bedroom Barbara soon stripped Pete naked. She stood in front of him and looked at his rock hard cock bobbing up and down as if it had a mind of its own.

Slowly she undid the buttons on her silk blouse which she peeled away from her bare breasts. Pete's eyes were focused on her hard nipples.

She then unzipped her skirt, unbuttoning it and sliding it down her hips then off.

Pete audibly gasped as he took in her black satin girdle with four suspenders on each thigh holding up her shiny black silk stockings. Her four inch shiny black heels made her legs look longer.

Barbara was sure his cock had grown bigger.

She walked past him and laid down on the bed with her legs wide open.

'Come and fuck me Peter. Fuck me hard and I want you to give me at least two orgasms.'

Pete jumped on the bed and crawled between her thighs.

Luckily Barbara was already wet as he unceremoniously slid his cock quickly inside her.

He began humping her hard and she knew he wouldn't last long but she thought she would hurry things on a bit.

She dragged her middle finger over his puckered hole making him moan. When she slid it into his arse he groaned and shot his cum deep inside of her.

Barbara feigned displeasure and told Pete to get up.

She sat on the side of the bed and glared at him.

'Well young man that was lousy. I never got to cum and all it seemed you cared about was your own orgasm.'

Pete didn't know what to say so he kept quiet.

'Well I think you deserve to be punished!'

Pete's head shot up.

'Get over my lap you naughty little boy!'

Pete didn't move so she grabbed his arm and dragged him over her stocking clad thighs.

'No please don't spank me. Ouch!'

Barbara concentrated slapping the cheeks of his arse then interspersed the slaps by spanking the tops of his thighs.

Soon his yelps became groans then moans as she ran her hands over his sore bottom then traced a finger between his cheeks.

More spankings then more caressing.

Finally she leaned over and took a bottle of lube out of the nearest bedside set of drawers and squirted a dollop on the middle finger of her right hand.

Pete squirmed as she gently probed his little hole.

'Oh no please. Not that,' he begged.

'You seemed to like it a moment ago. Let's see if you do now!' then slid her finger all the way into his arse.

'Oh fuck!' groaned Pete.

Barbara began to finger fuck him causing him to moan and grind his crotch onto her stocking covered thigh. She could tell he had regained his erection so she added another finger stretching him further which caused him to grunt in discomfort at first then pant as she sawed them in and out of him. She sought out his prostate and as she ran her fingers over it he jumped and groaned.

'Good!' she thought. 'Time for the next level.'

She ordered him to stand then to lie on his back on the bed.

When she pulled out the wrist and ankle restraints that were attached to each corner of the bed Pete began to panic.

'Wha...What are those for?' he demanded to know.

'Oh just a special game we are going to play. Don't worry you'll love it.'

When he was secured she got out an anal vibrator that wasn't much bigger than the two fingers that had been in hi arse previously and eased it into him. Then she switched it on.

'Of fuck!' cried Pete as the vibrator rubbed against his prostate.

Next she took out a small flogger and brought it down on his cock and balls causing him to groan in pain and pleasure.

'I just need to see if you are really into this and by the look of your cock you certainly seem to be enjoying it.'

Pete's cock was as hard as it has ever been and leaking pre-cum like a tap.

After a few minutes of flogging his genitals she stopped then bent down and took his sore appendage into her mouth and sucked it.

'Oh my God,' cried Pete. He thought he was going to cum there and then.

Barbara then climbed onto the bed and mounted him.

'If you cum quickly again I will spank you and it will be a lot harder!'

Pete concentrated on not cumming as the older lady rode him to her own orgasm. It was difficult not to spurt as the anal vibrator was still buzzing away in his arse.

Soon Barbara was building up to her second orgasm.

'Get ready to cum with me darling. I'm almost there. Oh fuck!'

She came hard just as Pete erupted inside of her.

After a minute or so she released him and snuggled down on the bed with him slowly stroking his limp cock.

'Well Peter did you enjoy that?'

Pete had to admit he had in fact enjoyed it very much.

'Would you like to see me again and let us see if we can push your boundaries even further?'

Pete took a minute to think but finally said that he would like to come back as long as it wasn't going to cause him any permanent damage. Barbara assured him that she wouldn't but would definitely give him amazing orgasms.

'Speaking of orgasms, you seem to be recovered enough to make love to me.'

Barbara laid back and Pete once more crawled up between her thighs but this time he took his time and made slow sensual love to her culminating in an enjoyable orgasm for both of them.

Over the next couple of weeks Pete was introduced to more larger dildos and floggers. One time he was tied to the bed face down and she milked him by fucking his arse with a long thin rubber cock, concentrating on running it over his prostate. She loved the way he groaned and squirmed on the large bath towel as she milked him.

The sessions still started with cunnilingus and finished with passionate sex but in between Pete's hole was being stretched in readiness for his visit to Audrey.

One afternoon when they were lying in bed post orgasm Barbra told Pete that she would be going out of town for a couple of weeks. Pete looked crestfallen.

'I hope you don't mind but I have arranged for my friend Audrey to carry on with your train...er your education.'

Pete had loads of questions about the new lady but all Barbara told him was that he would enjoy every second.

'You will be a good boy for Mummy and go along to see Aunt Audrey won't you?' she asked as she slowly stroked his cock.

Pete's cock lurched in her hand when she said that and he reluctantly agreed.

Four days later when Pete was alone in his house his phone rang. Nervously he answered it.

'He..Hello?'

'Is that Peter? It's Audrey here. I believe Barbara Mason said I was going to call.'

Pete thought the voice sounded cultured and warm.

'Oh Hi. Ye..yes she did say you would call.'

'Oh good. I would like you to visit me tomorrow at eleven in the morning. Would you be able to do that?

Pete confirmed he would be able to.

'Good boy. I'll text you my address.'

Then the line went dead and Pete realised he had an erection.

At eleven o#clock the next morning he found himself ringing the bell of a large detached house in an upmarket area of town.

He heard the click clack of high heels before the door opened.

He stared at the tall slim older women who invited him in.

He realised he hadn't said a word and hadn't really heard any of her greeting except to remove his footwear. He was bewitched by the glamorous dark haired woman who was dressed in a tight black woolen dress. She wasn't busty but had curvy hips and as she turned to lead him into the house he saw she had a nice plump bottom. He could also see the seams of her black silk stockings above her shiny black four inch heels. Even without her shoes she would have been taller than him, with them she towered above him.

She led him into her sitting room and told him to sit in an armchair as she took the one opposite.

As Audrey sat back and crossed her legs her dress rode up showing more of her thigh to a nervous Pete.

'So Peter, I believe you've been enjoying some er... guidance from Barbara Mason. Is that correct?'

'Ye...yes Audrey,' he replied meekly.

'I think you'd better call me Aunt Audrey, don't you?'

Pete nodded and blushed.

'Good boy. Why don't you stand and remove your clothing?'

Pete slowly got to his feet and shrugged off his t-shirt before dropping his shorts and underwear. His cock was hard and his balls heavy.

Audrey uncrossed her legs and spread them wide.

'I believe this is how we are supposed to start!'

Pete went down on his knees and slowly moved his face under her skirt and could see she wasn't wearing panties, her bald sex dripping with juices.

'Good boy Peter. Show me what you have learned.'

Pete began to kiss and lick her outer lips before tonguing her vulva then up to her clitoris where he could tell she was beginning to react to his administrations.

He licked and slurped on the older woman's pussy that was now dripping with juices.

With a groan Audrey gripped Pete's head and held it tight on her gushing cunt as she came hard on his face.

'Oh you have been paying attention to your lessons. Haven't you Peter?

Ye...yes Aunt Audrey,' Pete replied looking down at the carpet but only seeing her classy shiny black heels.

'Well I think we should go on upstairs to my play room,' Audrey said as she stood up and walked to the door.

'Do hurry up. Oh, and leave your clothes where they are, you can retrieve them when I've finished with you.'

Pete jumped to he feet and hurried after her.

When they were inside the room Pete marveled at the blacked out windows covered in heavy black curtains, a large metal frame bed with black rubber sheets, a rack of floggers and whips, a glass cabinet full of sex toys and something that looked like a small vaulting horse that he'd used in school but much smaller with a padded shiny black rubber top and with cuffs attached to all the legs.

'Yes a little intimidating don't you think. My last husband was very into being dominated. We used to play crazy tie up games where I'd whip and flog then bugger him Unfortunately he was working in his office one day when he had a heart attack and died. How ironic.'

Pete was really nervous now but before he could run Audrey asked him to unzip her dress and turned her back on him.

Pete pulled down the zip and Audrey stepped out of the dress to reveal a tight black satin basque that had four suspenders on each thigh holding up her stockings. She hung the dress over a chair and faced Pete. He could see that her breasts almost spilled out of the top of the basque and his cock got even harder.

'Come on, up on the bed with you.'

Pete gasped as he laid back on the cool rubber sheets and Audrey giggled.

She climbed up on the bed and gracefully crawled over to him, laying down beside him and resting on her left elbow she began to slowly stroke his cock.

'We're going to explore your darkest fantasies Peter. Barbara seems to think you are ready for what we are going to do today. If you are we can progress with your training.'

She turned to him and pulled down the top of her basque freeing her breasts. Once bare Pete thought they were bigger than he first thought being obviously constrained by her underwear.

He couldn't stop looking at her huge nipples, they stuck out like organ stops.

'Yes I do have very large nipples Peter and they are very sensitive. I love them to be sucked. Why don't you take one in your mouth now!'

Pete eagerly sucked on her huge teat making Audrey moan.

'That's it Peter, now chew them. Oh my God, yes!'

Pete sucked, chewed gently, then not so gently bit down on them.

'Oh fuck! Audrey cried as she pushed Pete onto his back and straddled his cock before easily sliding down the length of it.

'Please don't cum too quickly Peter I need to fuck your big hard cock.'

Pete looked at the mature woman astride him and saw her slim body dressed in a black satin basque, black silk stockings and shiny black heels riding his throbbing dick. He knew it was going to be difficult to hold on and he hoped she would cum quickly before he did.

'Oh yes Peter. Fuck that's good. Oh I love your cock.' she chanted as she bobbed up and down on the prone boy.

Suddenly she started to ride him faster.

'I'm nearly there Peter. Cum with me darling. I want to feel you filling me up with your cream.'

Pete was fighting to hold on when she screamed.

'Oh God I'm cumming Peter. Give me your load darling. Aaarrrgghhh!'

Pete groaned loudly and lifting his hips off the bed exploded inside of Audrey.

They lay side by side sated from their lovemaking.

Audrey was the first to move as she leaned over Pete.

'Let Aunt Audrey give you a kiss to thank you for such a wonderful orgasm.'

She then lowered her head to his and her lips descended seeking out Pete's.

They kissed long and passionately.

Once she'd broken the kiss she lay back again, her hand toying idly with his flaccid cock.

'Oh I must get this hard for the next part of your tuition. It will make it a lot more enjoyable for you if it is!'

Pete wondered what was in store for him next.

After a few minutes Audrey went down on him and took his semi hard cock in her mouth and sucked it to full erection.

'So Peter are you ready?'

Pete gulped and stammered 'Ye..yes Aunt Audrey.'

'Good boy. Right come with me.'

She led him over to the wooden horse-like contraption.

'I want you to lay your body over the seat of the horse with your feet on the ground but stand on your toes.'

Pete stared at it nervously.

'Wha...what are you going to do to me?'

'Oh something both Barbara and I think you will enjoy.'

Pete gingerly lowered himself over the cool padded rubber top and then he felt his legs being pulled apart and secured to the cuffs at each leg of each leg of the horse.

Audrey then walked in front of him an took his hands and did the same securing his wrists to the other set of cuffs.

Pete was now tied tight with his head at waist height and his bottom high in the air. He didn't think he liked where this was going. He felt too helpless and exposed.

He saw Audrey out of the corner of his eye go to the cabinet, open a drawer and take out a medium sized flogger.

'Barbara tells me you like a little pain well let's see how much you can take.'

With that she brought the flogger down on his arse. Pete groaned and shifted higher on the horse, his cock rubbing against the shiny rubber and his balls swaying between his thighs.

More blows fell on his arse and thighs which sometimes caught his balls making him moan continuously. The pre-cum oozing from his rock hard cock was making the rubber seat wet and enabled it to slide up and down driving him crazy.

After a short while she put away the flogger and disappeared into an adjoining bathroom leaving Pete panting and squirming, hopelessly trying to make himself cum on the rubber seat.

A short couple of minutes later Audrey appeared.

Pete gasped as she walked in front of him lubing up the six inch pink strap-on dildo she was wearing.

'Oh no. Please not that. I don't think I...'

'Oh we think you can and that you will love it so much you'll come for more and more!'

As she said that she went behind Pete who gasped when he felt cool lube being pushed into his arse. First one finger penetrated him, then a second adding more lube. When three fingers slid into him he was continually groaning.

'Right, let's see what we can do here!' she said as she withdrew her fingers and lined her cock up with his hole.

He grunted when the head of the cock slipped past his sphincter and groaned when he felt a burning sensation as she forced the dildo home. He felt very full.

'Well done Peter, you've taken all my cock. Now I'd better fuck you!'

She started slowly and eased it in and out of him for a minute or two then increased her thrusts a little, changing her action so the cock glided over his prostate. Pete was surprised how wonderful it felt to be tied down and buggered by this older woman.

At every thrust his own cock would rub along the shiny, wet rubber as more pre-cum flooded out of him. Then with one hard push of Audrey's hips he felt his foreskin pull back so his wet crown was rubbing up and down as he was being fucked causing him to continuously moan.

Soon he could feel his balls churning as Audrey pounded his arse.

'Oh God Aunt Audrey I'm going to cum. Oh fuck yeessss!

His body shook as he came.

Audrey eased the dido out of his arse then left him to calm down as she went back into the bathroom.