The Hunt for Cassidy's Virginity

The Hunt for Cassidy's Virginity
By Steam Train

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This work is intended for ADULTS ONLY. It contains depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.

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Inspired by The End of Heather's Babysitting Career by Y. Lee Coyote available on his web site The Coyote's Den.

Story Four of the Hunt Series

This is the 4th story in the "Hunt Series" which follows the further adventures of the female characters Caitlin and Cassidy from my stories: The Hunt for Kyle's Pubes, The Hunt for Mike's Cock and The Hunt for Travis' Cum available at: http://www.asstr.org/~nialos/steam_train.html#THFS

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The Hunt for Cassidy's Virginity

The day before I succeeded in stripping and humiliating Travis Haussler with a behavior management program, I received from the Turner twins, Eli and Jacob, a video taken by Aaron Cabane, which I planned to use to blackmail David Colby into submitting to behavior management as well.

I had picked up the babysitting duties for Eli and Jacob Turner some time ago, thanks to a recommendation from Mrs Cabane, and as my business grew I took on my best friend Cassidy as a junior partner. With too many babysitting jobs on my books for just me to attend to, she was a big help in spreading the work load. Lately my life had become so busy that I had also taken on my younger sister Tanya as an assistant as well.

With all this help I was still struggling. My extra curricular activities in hunting down Kyle, Mike and Travis had distracted me from my studies and I was dreading the results of a test I had sat this past week. I had not had the time to study for it and I knew I had not done well.

Occasionally I looked after the Turner twins but most of the time it was Cassidy who looked after them. I was firm and strict with all the children to whom I was their babysitter, but at the same time I always tried to be very fair in allocating punishment, it was never undeserved. Cassidy unfortunately was not as fair, and her disciplinary methods had lead to both the Turner twins hating her!

When I sat the twins, I spanked them if required, so did their parents and so did Cassidy, but the way Cassidy did it, had bought about great resentment from Eli and Jacob.

The twins understood the concepts of discipline, punishment and reward and like all active twelve year old boys, they took chances, sometimes they did dangerous things; sometimes they were openly disobedient. The punishments I gave out varied; sometimes it was just the loss of a privilege and sometimes it was more severe like a spanking. In all cases my demeanor clearly indicated to the twins that it was a necessary but unpleasant duty. The Twins had complained to me that this was not the case with Cassidy.

The twins insisted that Cassidy relished punishing them, caring little, if at all, about fairness, their dignity or self-respect. Cassidy apparently constructed situations just to get the twins into trouble. She teased them endlessly as well, about how neither Eli nor Jacob had pubes. The twins told me that each time Cassidy pulled down their pants and underwear before dragging them over her lap for a spanking; she would mock about being twelve years old and still being bald. Saying boastful things like, "I had lots of pubic hair by the time I was eleven". She would also gleefully mention their lack of pubes in front of their peers and at every opportunity punished them before their goggle eyed friends.

Cassidy and I had originally concocted a plan that involved her luring David into a situation where he would strip naked for her in the hope of getting Cassidy naked. We were going to use Aaron's expertise in video recording to capture David naked. Cassidy was a known cock tease and our plan revolved around her supposed liking for bondage and discipline. However when Cassidy tried to entice David, he proved to be far too shy and modest to allow himself to be stripped first, let alone to be tied up! At first Cassidy was equally unwilling to tempt David by becoming naked in front of him!

Our plan had so far been a total failure. Cassidy had not even succeeded in getting to feel him up, let alone get him naked!

Eventually Cassidy had reluctantly agreed with me that she would have to strip first and thus entice David to do the same.

Aaron may have only just turned 12, but he was mature in body and mind for his age. He was also very good with technology. Aaron had proved his abilities to me with videos showcasing my babysitting skills and other skills as well, but that's another story, so I was pretty quite sure he could succeed in what he planned.

Aaron knew that our plan had not worked and that Cassidy had eventually agreed to the far more embarrassing alternative of stripping first. So it came about that Aaron and the twins put a revised plan to me for revenge on Cassidy and at the same time incriminating David Colby.

The revised plan however presented me with a moral dilemma. It involved me condoning Cassidy being naked not just in front of David but in front of the twins as well and also allow them to punish her, before the planned video sex session with David Colby.

He was as keen as the twins to get some revenge on Cassidy; therefore like he had done with me, he produced a secret video of Cassidy punishing the twins and the three boys presented it to me. It proved beyond doubt that Cassidy was going overboard in her handling of Eli and Jacob.

Aaron's plan was to confronted Cassidy with the video evidence and then give her the choice of either being publicly exposed for what she had done to Eli and Jacob and the resultant probable criminal charges or agreeing to allow the twins to prepare her for David by stripping her then tying her up naked as the bait to tempt David into action.

What the boys did not want Cassidy told was that once she was immobilized, in retribution for her treatment and teasing of them, the Twins would spank her till she cried and if she had not already done so, shave off her pubes so she too was hairless like the twins.

It was against my principles to allow boys the upper hand over a female, but Aaron was persuasive. He had video evidence against me and that fact alone was a very great persuader! Also there was the fact that any public exposure of Cassidy's babysitting methods would wreck more than just her babysitting career. Finally I after a lot of thought I rationalized in my mind that Cassidy was going to get naked for David anyway and I needed ammunition against David, Aaron's plan presented me with much more damaging video against David than my original plan would have produced, so reluctantly, I agreed to Aaron's plan.

I did the right thing by Cassidy. I sat through as the boys presented the video evidence against her. At first I think she thought it was not important but gradually she realised the videos would be made public by the boys if she did not cooperate.

You can imagine her reaction to the revised plan. First, flat out refusal, second, when she realised that would mean going public with the video, she asked for a compromise solution, third she begged not to be made to do it, when the boys would not budge from their position.

I hated seeing my best friend and fellow female boxed so tightly into a corner but she had to a large extent bought this on herself and in my mind I knew that with Cassidy being naked, our plan would now stand a very good chance of actually snaring David Colby. I confess I was also secretly turned on by the thought of watching Cassidy being stripped naked!

By the end of the session an already humiliated and embarrassed Cassidy had reluctantly agreed to all the boys' demands. Before Saturday night when Cassidy was next rostered to sit the boys, she was to ring David and invite him over to the twins' house with the promise that as she was into bondage, she would be naked and tied up waiting for him to have his way with her, as long as he acted out her fantasy role play as well.

What 14 year old guy could turn down an offer like that?

My first worry was that he would brag about his upcoming triumph, so I instructed Cassidy to be firm on the point that if she heard even one slight whisper she was calling everything off! The second worry was to stop him bragging after his triumph. My original thought was to confront David as soon as he was finished with Cassidy but I was discussing David with my mother and she wanted me to hold off so she could organize some special punishments with David's mum. So I decided David would have to be kept quite by promises of additional sex with Cassidy provided he did not talk to anyone about it. It was a big risk as fourteen year old boys are not good at keeping secrets!

I am very open with my mother and the two of us keep very few things secret from each other. My mum as I have mentioned is right into female domination and is in fact the treasurer of a local female activist group. Mrs Colby was also a member it seems, but unlike mum she was not a female dominant, but merely one who wished she was. Mr Colby, mum told me, was a real male chauvinist and his attitude had rubbed off on David. Mr Colby worked in a very male environment, on oil rigs off the Brazilian coast. He would work 28 day shifts then fly home for 26 days before returning for another shift. He ruled the roost when he was home and when he was gone Mrs Colby was increasingly having trouble controlling David. If David objected to her wishes he would email his dad and Mr Colby would invariably come down on his sons' side.

When mum heard about Aaron's video plan and how it would appear that David had raped Cassidy she knew Mrs Colby would finally have something to make David tow her line. Even Mr Colby would be powerless in preventing David being bought to trial for rape if the video became public. Mum's idea was to let David know it existed, for Mrs Colby to pretend she was totally shocked and disgusted in his actions ..... BUT ..... if David agreed to her behavior modification structure she would try to have the video kept private.

So David's demise turned into a much more humiliating and elaborate plan with his mothers support, than I had originally planned.

On the chosen Saturday, a couple of hours before the appointed time for David to arrive, I went over to the twins' house along with Aaron to supervised proceedings.

Before I allowed Cassidy to be stripped by the twins, I rehearsed with her the lines she was to say and also went over how the twins were to greet David at the door and make sure he understood that Cassidy was role playing a bondage session and reaffirm that he had to act along with it.

After a few rehearsals I felt they had it down pretty good, so it was time for Cassidy's undressing!

Poor Cassidy, she had to stand before the three boys with me watching and allow the twins to remove her clothing piece by piece. I confess I found the whole scene very erotic and the gusset of my panties was very moist. Cassidy looked totally humiliated and embarrassed. Aaron had a prominent bulge in his jeans and the twins had less prominent boy-sized bulges in their pants.

It did not take all that much time for the profusely blushing Cassidy to be down to just her bra and panties. It was Eli that undid the hooks of her bra and Jacob who pulled it off, exposing Cassidy's upthrust B cup, pink nippled breasts!

"They look smaller exposed." observed Jacob who then reached out to feel them. Cassidy immediately stepped back, bumping into Eli who was still standing behind her. "No touching" Cassidy verbally asserted.

"Tonight we are in charge of you remember" Eli responded, "Go ahead bro, have a good feel of those titties."

Cassidy looked over to me for support, but all I could think of saying was, "Sorry Cas, you agreed and .... the video evidence, you know ......!"

Eli stood his ground behind Cassidy preventing her from moving further back as Jacob reached out again and cupped his hands over her breasts. Within seconds her nipples were hard and a red blush descended from her face all the way down her chest to her breasts as she let out an embarrassing low moan of pleasure.

As the twins began exploring Cassidy's tits, Aaron inspected the bra Jacob had just removed and reported that it was padded. Cassidy's natural breasts were quite a reasonable size and nothing to be too embarrassed about. Her bust to chest band difference looked to be about two inches which gave her B cup breasts, but this size difference placed her on the brink of having C cup size breasts like mine.

As Eli moved to the front of Cassidy and took over from his brother in caressing Cassidy's exposed breasts he commented, "Getting a bit excited I see, your nipples are so hard."

This released a new barrage of abuse from Cassidy's mouth.

Eli was a man of action and after a brief but thorough feel of Cassidy's tits; he moved on, but when he attempted to pull Cassidy's panties down Cassidy grabbed the waistband of her panties.

"Please Eli, don't" Cassidy's begged.

Cassidy had a firm grip and Eli was not making any progress in lowering her panties, until Aaron threatened her with a severe spanking and video exposure unless she let go and put her hands on her head!

Reluctantly Cassidy let go of her waistband and put her hands behind her head. Tears began flowing down her face as she began crying softly. Her crying intensified as Eli slipped a hand under each side of the waistband of her panties and tugged them down, letting them fall to her feet.

Eli and Jacob, who had remained standing to one side of Cassidy, both had their eyes glued to her crotch, as Aaron also leaned forward to look at the genitals of a real, live girl! From their reactions I think it was the very first time for all the boys seeing a girl naked.

The removal of Cassidy's panties exposed her extremely hairy pubic area. There was certainly no grooming of her pubic hair like I did let alone shaving like a lot of girls our age practised. "You're very hairy down there" was Jacob first observation.

"Yeah very 'a la natural' Aaron added. "She sure hasn't learned the art of the bikini trim. You know guys we could see a lot more of Cassidy if all this hair was not here!"

"Don't you even think of trimming my pubes" Cassidy threatened.

"Oh I wasn't thinking of a trim Cassidy" Aaron stated with a smirk, "I was thinking of removing it all, so you're totally bald down there."

The boys were well prepared and had bought rope to tie Cassidy up for the bondage session and shaving gear to do just what Aaron was suggesting..

Cassidy made to dash out of the house but the boys were too quick and the three of them with a lot of effort over powered her and then after quite a struggle succeeded in tying her up and spread star fashion on the floor. As they did so, she was yelling and pleading to them, but the boys ignored her every word.

Eli made the only comment, "Now you know how we felt."

Soon Jacob had trimmed her thick scraggy pubic bush right back exposing her previously hidden feminine charms. Her pink puffy lips were now clearly showing through the stubble.

When Jacob was finished, Eli lathered up the pubic stubble and within minutes the three boys had succeeded in shaving Cassidy's pubic area totally bald!

"That's much better' Aaron commented.

"Yeah I can see everything down there now" Justin replied as Eli reached out and as Cassidy visibly trembled in front of him, parted her totally exposed lips and poked his forefinger into her.

Cassidy gasped "Noooooooo" as he pushed into her dry channel!

.Despite herself Cassidy very soon appeared to be very aroused and she stopped yelling and was reacting to Eli's manipulations with heavy breathing and noticeable vaginal secretions.

Three sets of hands then fondled her naked bald body and it did not take long for Cassidy to scream out in ecstasy as she climaxed.

Still recovering from a public orgasm, the boys shifted her position, bending her over the arm of a chair and thus exposing her naked bottom.

"Noooo don't spank me please" Cassidy begged.

Again I was in too minds, embarrassed at a female being put in this situation but also highly aroused

"Cassidy, you have been a very naughty girl and we are going to spank you very hard." The twins announced together.

Cassidy begged for mercy but to no avail and soon gave up resisting!

I was beside myself with anticipation despite the fact that it was Cassidy who was about to be spanked. I knew that Cassidy like me had never ever been spanked in her life. Now she was going to get it. From the look on her face I could tell she was also thinking to herself. "I'm actually going to get a spanking!"

I thought of all the times she'd laughed at the twins as they received a thorough spanking, enjoying the sight of their little boy little boy genitals and felt the soft skin and firm muscle underneath each time her hand struck their naked bottoms.

From the look of fear and disbelief on Cassidy's face I could guess she was wondering how bad spankings hurt. Boys she had spanked always cried like their butts were on fire, and continued to cry afterward for quite some time. I know from our private conversations that Cassidy revelled in the power she had as their babysitter to make boys cry but I am sure she'd never dreamed she'd be on the receiving end. I hoped Cassidy would have the fortitude to hold still, and not yell or cry, no matter how much it hurt. She had to uphold the honour of us females

Aaron handed the twins a belt and they took turns in beating Cassidy's bottom. The first blow obviously surprised her with its sting. One moment she was tensing her butt and waiting for the impact, the next moment after the belt found its mark she let out a gasp and kicked out as much as possible with her legs bound.

"Ahhhhhhhhhhhh!" she cried out. "It hurrrrrrrts!" Tears sprang to her eyes immediately. "Please, pleeeeese," she wailed almost as soon as the twins began her belting! So much for holding up the female honour!

The twins response was to deliver even harder spanks and Cassidy soon lost all control and dissolved into incoherent sobs by the sixth spank.

From her reaction Cassidy obviously realized it hurt so badly! I think she now knew why the boys she spanked bawled and screamed so much! As the spanking continued unabated, Cassidy began flailing against her constraints, grasping for air, sobbing incoherently and screaming blue murder as the twins continued relentlessly smacking her butt, spreading the spanks around so that her whole posterior glowed.

As they continued with Cassidy's punishment, the twins and Aaron just smiled at each other enjoying her suffering.

When they finally stopped her strapping Cassidy was crying uncontrollably but the boys showed her little compassion, instead moving her into a position on the floor with legs again spread, revealing Cassidy's most private of parts and readying her for David's imminent arrival, wiping her runny nose, drying up her teary cheeks and then to keep her aroused fondled her naked body all over.

As Eli and Jacob were busy preparing Cassidy for David, Aaron and I retreated to the kitchen. After Cassidy's stripping and the continuing noise from the living room of Cassidy's heavy breathing and moaning as the twins felt her up, I was quite aroused and so was Aaron!

Soon Aaron and I had adjourned to the twin's bedroom to watch proceedings with David on their laptop. Aaron still had a large bulge in his jeans and I feeling equally flushed and aroused. I could understand Aaron's excitement at seeing Cassidy stripped and knowing that she was soon to loose her virginity. What Aaron didn't know was that I too was a virgin but at that moment I was so aroused I was unable to resist any advances Aaron made and like any horney twelve year old he hit fully onto me. I was virtually powerless to resist his sexual advances. The fact I was nearly fifteen and Aaron had just turned twelve didn't matter at that moment in time and so before David took Cassidy's virginity Aaron had taken mine, though I don't think he realized just how big a conquest he had just made!

I was so consumed with Aaron that I was distracted from the PC and only took in certain parts of the live action between Cassidy and David. Of course I had the video that Aaron had set up to go back over in my own time and during the next few weeks I masturbated myself to orgasm numerous times watching David lower his jeans and roll a condom on his rampant shaft and aim it at Cassidy's well lubricated and dripping target. David's cock was a good size for a guy of fourteen, it was thick and appeared to be about five and a half inches erect and crowned by an ample but not large bush of pubes. His cock and pubes were complimented by a hanging but still hairless set of balls!

The only time my full attention was on Cassidy and David was when David went down on his knees and made his first thrust into Cassidy, claiming her virginity and then with only a few additional thrusts, shoot his load, as almost simultaneously, I was again bought to my second orgasm in minutes by Aaron!

I confess that after Aaron's taking of my virginity I was beginning to feel I was no longer in a position of total control over Aaron. Was this a premonition about how my dominating relationship with him was about to change?

The End

With Steam Train's permission, Y. Lee Coyote has written a sequel to The Hunt for Cassidy's Virginity
which is available on his website The Coyote's Den using the following direct link:
"A" Is for Aaron and Alpha Male