The Virgins Humiliaton

"Oh dear young man" looks like you couldn't handle a classy Cougher in real life". James knew the game was up. Jus's final act of cruelty was to give his exposed anus a long hard quirt of lubricant.."I think you'll thank me later for that young man" she said with a cruel smirking voice....

Chapter 5 - The Administering of Punishment

The enormity of the situation hit James and he was not looking forward to the next hour. He knew he could stop it by use of the safe word at any time, but equally as much he desired Jus and he knew if he halted proceedings a chance of a future rematch would be off the table. He was sure he could train himself to last! He meekly therefore knew he had to accept his fate like a man. How bad could it be?

Jus stood haughtily behind the table, enjoying the view of James rear end stuck in the air, his open thighs perfectly framing his large penis and testicles.

"Pass me the hairbrush darling" Jus uttered to Rog. Rog retreated to the other side of the room and returned with a fearsome looking implement. A large ebony hairbrush, the handle of which alone was twelve inches long. The handle connected to a large head circa 6 inches long and 4 wide. It was in effect and to all intents and purposes a very vindictive looking spanking paddle. Jus had purchase it off the internet from a dominatrix and knew it had reduced lots of bottoms to whimpering wrecks over the years.

A final act of humiliation was for Rog to wheel the full length dressing mirror into position at the front of the desk, so that poor James would be able to watch his entire punishment as it unfolded.

Jus produced a pair of very skimpy pink panties and told James to put them on. He did so obediently as was expected and ensured that the pink thong went up his backside exposing both pert cheeks. The silky panties cradled his dangling balls, although they were rather uncomfortably tight, a factor Jus was well aware of and added to her fun.

Jus made a big event of stroking his stirring penis and balls through the silk to ensure he kept erect and that the rubbing of the silk on his swollen penis tip was suitably unpleasant.

Jus stood behind James and informed him he would be taking 12 of the best. And that he would count the strokes, and thanks her and Rog for each stroke.

At the count of three, Jus provided the first Thwack. It landed on his left cheek with a satisfying "Thwack". "One, Thank you Mistress, Thanks you sir.".

As soon as Jus pulled the hairbrush back for the second stroke she could see that James rump was already turning a shade of crimson!.

Jus issued a further two strokes, upon the third James cried out in pain. This was of course not allowed Jus effortlessly slipped of her crotchless panties and told James to open wide. He did so obedient and had the silky knickers pushed into his open mouth, effectively gagging him. Jus smirked as she told him that should prevent a further noise, but if it didn't there were options.... As she said this she glanced at Rog's swollen crotch.

The punishment continued until the half way point at which Jus felt it fair only to allow a short break. Jus allowed James to recover slightly, and then an act of sheer cruelty crossed her mind.... She turned over the brush and started to run the spiky bristles over poor James cock and balls, worse still she deftly reached through and slipped his silky panties to one side for maximum discomfort. As she rubbed the end of the brush up and down over his hugely sensitive penis shaft and tip she could hear James groan through the panty gag. He was positively pleading after a minute and the spiky bristles made a fiery pattern on his penis. Jus cruelly administered a sharp upwards thwack to his balls which brought James back to attention.

Jus cruelly grabbed James by his balls ans said "one more word out of you and ill hold you like this and the remaining six strokes will be administered to your swollen testicles. Understood?". James meekly nodded.

"Right young man, second half" with this a further 6 strokes were administered, thwacking hard across alternate cheeks. At the end of the ordeal Jus was pleased with her handiwork, the poor lads buttocks being a shade of perfect pink matching his panties.

Jus stood back as James remained in position, panting with the effect. But so much worse was to come...

Jus swapped her hold on the hairbrush handle and presented the handle end to James's rear It was rounded like a thick truncheon on the end with a pleasant ribbed feel. She pushed it gently towards James and started to tease his anus with it. James pulled forwards at the sensation but Jus continued. She kept going until the tip was penetrating James poor rear entrance. The more James wriggled, the further it went in. Jus was able to lean into him and whisper naughty words into his ear. He was in no uncertain terms he would be subject to much worse in the shortness of time

Chapter 6 - The Taking of James "Cherry"

James was told to stay in position as Jus gently rubbed his swollen penis through the panties. He was so aroused it was incredible. He knew worse was to come but couldn't consider backing out as he really wanted this fine lady so much. He was prepared to pay any price.

Jus was certainly going to have fun, She knew Rog was watching fascinated and was determined to give him a show also. She sidled up behind James and told him he would be restrained for the next phase. Again the safe word was reiterated. James remained on the desk on all fours but had each ankle restrained to a rear desk leg, and his hands tied together in front of him. The tying of his ankles allowed his backside to be fully presented, and his cheeks to be fully opened. As Jus looked down at him she could see his anus in clear view with nothing to obstruct or protect from the ordeal to come.

Jus looked at Rog. "bring the trunk round will you please darling?". James was confused but shortly Rog came round the corner from the rear of the room wheeling a large antique steamer trunk on wheels. He parked it in front of the pair and opened it up.

The trunk was a genuine antique but had had shelves and an interior fitted in beautiful red suede. On one of the shelves was placed a large leather sturdy Strap=on harness. On the other top shelf was the largest array of dildos James had ever seen. They ranged from small, to large, to downright cruel.

Jus asked James to look at the shelf of Dildos and tell her which one he felt he would take. James stuttered that he wasn't sure, the smallest perhaps. Jus met this with a giggle,

"Well Well young man, we have a short memory don't we?. Not an hour ago you were telling me if you won the bet you would have me, and where where you going to take me?." James shook his head...

"Tell me young Man "barked Jus. James hung his head in shame and told her he was intending taking her in her perfect derrière should he have won.

"And how big is your penis James" asked Jus? James was silent so Jus informed him they would have to see. She slipped lower his silky panties and asked Rog to come forwards. Rog was holding a tape measure...

Jus instructed Rog to measure James's penis. Rog was clearly shocked and hesitant but Jus was insistent. With this Rog firmly gripped the base of James penis and measured down the length of the shaft. It was as per the photo 9 inches to a mm. He then wrapped the tape round the width and confirmed again 6.5 inches in circumference.

"Rog, select a suitable matching dildo please darling. Rog walked to the cabinet and selected a nine inch phallus. It was black, rubber and sleek, and very lifelike. it even had a matching set of duck egg like balls.

"Well James, what's good for the goose is good for the gander". Jus smirked and took the harness off Rog. She stood in front of James face as she donned the leather harness, and made a great show of inserting the dildo into the hole. Jus looked magnificent with the huge phallus between her legs. She was very much enjoying wielding it. Her first job was to make James inspect his tormentor. She stood in front of him holding the tip of the vibrator to his face.

"The lubricant please Rog". Rog held out a pot of lubricant to Jus who took it and held it in front of James face.

"Well well young man. Best get prepared. ". She took a dollop of lubricant and started to work it into the length of the huge phallus. Watching her work it in was transfixing to James. She masturbated it in, ensuring a large dollop was left on the end. She then looked at James and pointed at the dildo tip.

"James, look at your tormentor. I want you to kiss the tip and beg me for a fucking. If you beg well enough ill lube up your backside prior to screwing you!"

James meekly looked at the fierce looking penis and put his lips to the tip. He kissed it and reared back.

"Please miss, give me a screwing. "

"Sorry, I cant hear you young Man"?

"Please screw me senseless at your mercy mistress."

Jus went round behind James and started to prepare him. She smirked to herself.

"Well James, I think ill do you like in the films you dirty young boys seem to like to watch". With this she pulled the thong of his panties to one side to expose his anus!!.

She placed a dollop of lube on his anus and massaged it in with the tip of the dildo. It was almost time.

Jus took a small vibrator off Rog and worked placed it slowly into James anus. She worked it in and out as he relaxed and then put it down to prepare for the main event.

She placed a slender hand on each of James's pert butt cheeks and pressed the tip of the lubricated phallus to his anus. She applied gently pressure as first the tip went in, and then a further half inch. She slowly started to move it backwards and forwards as James whimpered.

After five minutes she was making progress but not as much as would have liked. She took a bottle of lubricant and literally poured it on to the shaft of the phallus. This had the desired effect and shortly she noticed that she had a much larger percentage of the phallus embedded in poor James bottom. With this she grabbed him by the hips and increased the thrusting as she drove home the phallus with each stroke, much to the suffering of the hapless victim.

James could hear a slapping sound, and it took a while to realise in his delirious state it was the sound of the rubber balls attached to the giant phallus slapping against his backside, which could only mean that he was now fully penetrated.

Jus heard a meek voice call out "oh no please no, oh help". She knew what had happened and reached round to feel his penis. She could feel the slipyness and knew he had gone to far.

She demanded Rog pass her a pair of spare panties. Rog passed her the red silky she sometimes wore and she reached in front of James and mopped him up.

"Open wide young man". She giggled. James opened wide and Jus took delight in stuffing the wet knickers into his mouth. "There, that will teach you". The humiliation was complete.

James was now beyond humiliated, what made it worse was the phallus was still buried in his backside. The thrust massaging his prostrate had been too much and he had had no control over his penis as he had lost his load. Jus continued the thrusting for another five minutes at which point she felt he had had enough. She pulled back and the phallus left with a pop and with this she pulled poor James Panties back into place. As with most young men a speedy recovery would she felt be assured.

Chapter 7 -- A Lesson learned

The evenings events had gone perfectly and utterly to plan. There was however to be a fitting climax to the event.

Jus was in a state of arousal, her vagina was wet from the thrills of the evening and further moistened with the anticipation of what was to come. Her huge nipples were hard and pert and her tummy had butterflies at the thought of the fun to come. Rog equally was beyond aroused, his member was straining against his tight Calvin Klein's as the outline of his erect penis showed.

"Well James, I think its time you found out what you could have won". With this Jus smirked cruelly and took Rog by the hand leading him to the bed. She had however taken a route past the trunk and selected an item as she passed..

The bed was a huge antique oak four poster covered in beautiful sheets and duvet cover in gold and looked like something out of a National trust magazine. The bed was canopied and of wonderful workmanship.

Jus summoned James and instructed him to stand in front of the bed facing the bed head. She wondered over to her trunk and took out 4 silk stockings, using them to tie first his arms to the top bar of the four poster and each ankle to the bed foot. The result was James spread-eagled and butt naked facing the bed.

Jus picked up the item she taken from the trunk and deposited it on the bed. It was a very well made and very solid stainless steel chastity device. She reached forward and took hold of James rising member and looked him in the eye. "If it cant be controlled it will be caged young man". With this she deftly fitted the cage and hung the key round her neck on its chain like a prize.

Jus clamoured into the bed to meet Rog and started to kiss him slowly. They behaved as if James wasn't present. Jus gripped Rog's penis and slowly masturbated him, whilst he played with her pussy, teasing her inner folds of her thighs and working his fingers up to her vaginal lips. Before long Rog was teasing her clit with his index finger, a technique that Jus clearly enjoyed.

The couple continued their foreplay for a full quarter of an hour, but the truth was they needed no further turn ons, both being utterly ready.

Rog as always felt like the luckiest guy in the world. Jus was beyond stunning, a realisation he had made the day they first met,. It was clear he wasn't the only man who felt like that given James performance or lack of it!!.

Jus winked at Rog and he sat on the bed facing James. Jus manoeuvred herself round and started to suck Rogers swollen penis slowly and rythmically, putting on a show. James looked distraught as he realised he could have been in Rogs position now if he had more staying power. Jus rythmically sucked the penis up and down, pausing periodically to look James in the eye as she sucked.

After a short while it was time for the cruelty level to ratchet up. Jus turned round and presented her rear at James. James was about 18 inches off her perfect rear, framed in the crotchless panties and stockings she was wearing. She ensured her thighs were open, and her stomach touching the bed as her vagina and anus were perfectly exposed. Poor James, so close and so far away. He had the most wonderful and yet frustrating view as Jus continued to suck Rog hard and slow, making as much slurping and moaning noises she could. Jus was fully aware of what she was doing, and kept pulling Rog to wriggle forwards and hence allowing herself to move backwards. She inched closer and closer to James. His engorged and yet captured prick was now not two inches off her vaginal entrance.

Jus pushed backwards, almost touching James swollen penis tip. She took her lips off Rogs cock and looked over her shoulder at James. She pressed her buttocks and vagina into his caged penis slowly and teasingly rubbing against him. The effect was delirious agony..

"Roger darling, he's been a good boy, shall I let James screw me, he could take me really hard from behind whilst I suck you darling".

Rog agreed and James could only look on speechless. Jus continued to rear back as her vaginal lips continued to rub on James caged penis.

"OK James, ill count to 3 then I want one good thrust see if you can pop that cage off!! understand?". James clearly did. Jus counted one, two and then...

Anyone who had worn a quality cage would know that it was an impossible task. James squeezed and puffed but it was totally ineffective.

"Oh darling, look, He cant be that keen on my rear, he wont get his cage off" Jus giggled cruelly.

James pleaded this wasnt the case at all as he stuttered his plea for release but it fell on deaf ears. James was by now a broken man, he had genuinely through it was his turn. Jus felt almost guilty as she explained if he went through with her final act of gamesmanship they would at least offer him a rematch the next month. James of course was to agree!.

Jus turned round to position herself buttocks to Rog, face facing Jame to give James a perfect view. She relaxed and allowed Rog to place his penis to her vaginal lips. She hadn't felt this wet in ages and judging by the pre-cum dripping of Rogs swollen prick nor had he. Rog was able to easily penetrate Jus given the natural lubrication and started to take her right in front of James. Humiliation was awful as James was convinced not once but twice in the night he would have his fantasy lady.

Rog gripped Jus by the hips and worked up to a pounding. Jus felt blissful as Rogs balls slapped her bottom, she loved to be fucked but nothing beat a tongue but then, as she had previously planned, why not simply have the best of both worlds.?

"Are you getting a good view James" she asked. James gulped and said that he was, Jus told him he would soon get a better view and wriggled forwards. She kept inching forwards until she was level with Rog. When she was level she looked up at James continuing to be rocked back and forth as she was screwed senseless, never taking her eyes off James caged cock. The frustration must have been awful!.

"So young man, a challenge. Ill give you a good sucking now, but when i'm bored you will go down on me, in my choice of position. James leapt at the chance hungrily nodding, if only the silly boy had known.

Jus inched forwards and took James in her mouth, He could barely fit such was the size of his penis. The sensation was incredible, his penis being sucked whilst Rogs pounding of Jus moved her head up and down his shaft. This continued for about 3 mins, until Jus decided she was ready for her fun.

With a satisfying pop she pulled her lips off James swollen member and dismounted Rog. She untied James and told him to climb on the bed on all fours. This would be the finale.

She instructed Rog to sit with his back to the bed head sat up and she moved backwards. Rog sat with his legs open and allowed Jus to move between his legs, her back facing him She lifted herself up and mounted his erect penis. Rog leaned back. This provided a great view as she could look down and see his shaft as it penetrated her full lips. She instructed James to come over with a smirk.

"Okay young man, time to put that tongue to good use" James stuttered as he realised what he was being asked to do, to perform oral on Jus whilst Rog was buried to the hilt inside her.

James resigned himself to his fate. He had come tonight to screw a cougher, and instead was being humiliated by her however he still held out for a rematch. Jus however, who knew this was a one off so was more than happy to have her fun. James got on all fours and started to work his tongue up and down Jus's clitoris. Jus was pleased that he was surprisingly good. He circulated her clitoris in slow strokes, the ever presence threat of Rogs prick was enough to keep him on target.

The sensation was incredible and Jus yearned for the building orgasm. Jus bounced up and down on the length of the shaft, the ordeal was made worse for James as his toungue on occasion missed her clitorus and landed on Rog's hot pulsing shaft. This was the most humiliating experience in his entire life, made worse by Jus smirking and giggling.

The ordeal continued for several minutes as Jus reached not one, but two very gushing climaxes. She allowed her self to recover as the final scene played out. Jus had however very much been looking forwards to the final act of cruelty. It had always been a little, actually huge fantasy of hers to watch some bisexual action and now it was finally time.