The Hunt for Caitlin's Bottom

The Hunt for Caitlin's Bottom
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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Story Five of the Hunt Series

This is the 5th 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, The Hunt for Travis' Cum and The Hunt for Cassidy's Virginity available at: http://www.asstr.org/~nialos/steam_train.html#THFS

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The Hunt for Caitlin's Bottom

It may have taken a lot of effort and some time to get Travis Haussler naked but it was taking even longer to ensnare David Colby. Initially I had decided that David was a follower and that Travis that was the leader and so Travis became my first object of revenge.

David however surprised me somewhat, for immediately that Travis had been reduced to a hairless little boy in front of his peers at home and at school, David had stepped up and took over his mantle of arch bully. In fact David even turned on his former leader and bullied the now humbled and humiliated Travis.

I could have stopped David in his tracks as I had the video evidence taken by Aaron Cabane of the set up where it appeared that David had raped my best friend Cassidy Di Medico. The delay was caused by a discussion I had with my mother about David. She wanted me to hold off confronting David with the video evidence so she could organize some special punishments with David's mum.

My mum is right into female domination and is in fact the treasurer of a local female activist group. David's mom was also a member, but unlike mum she was not a female dominant, but merely one who wished she was. Mr Colby 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. Unfortunately Mr Colby had just commenced a home shift and so a further delay eventuated until he returned to Brazil.

This delay meant Cassidy would have to try and keep David quite about their sexual liaison by promises of additional sex if he did not talk to anyone about it. It was a big risk as fourteen year old boys are not good at keeping secrets and fourteen year old boys are very horney!

Thus it came about that poor Cassidy was having sex with David on an almost daily basis after he took her virginity.

When mum heard about Aaron's video and how it would appear that David had raped Cassidy she knew Mrs Colby would finally have something to make David tow her line. The video was a powerful tool as 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 and then for Mrs Colby to pretend she was totally shocked and disgusted in his actions, but if David agreed to visit Dr Sutherland for a complete physical and to participate in her new behavior modification program then the video would be kept private. It took some time to get a suitable weekend appointment with Dr Sutherland and order in the equipment Dr Sutherland had Mrs Colby authorize to be fitted to David. Therefore David's demise took longer to organize than I had originally planned but it also turned into a much more humiliating and elaborate event.

The count down to David's demise started on the day David had taken Cassidy's virginity. That afternoon I had glanced out through the kitchen door of the Turner's house and could see the uncertain look on David's face. Cassidy had always been a cocktease but tonight he had been told was finally going to score.

I watched with Aaron beside me as Eli Turner repeated to David what I had taught him to say. That was that Cassidy had asked Jacob and himself to tie her up naked ready for some fun with him when he arrived. They were to watch everything and make sure David did not go further than arranged. As we had practiced Eli went on and explained how Cassidy wanted to play a game where she would pretend that David had tied her up and would resist his efforts to have sex with her. Eli made sure David knew it was a game and that Cassidy really wanted David to have sex with her. David's uncertainty was almost certainly over having to do it in front of the Turner twins and an underlying doubt about if this some sort of a trick!

Any doubts soon evaporated when David's eyes nearly popped out when Eli and Jacob bought him into the living room and he saw Cassidy tied up and spread naked before him on the floor.

He readily entered into the conversation Cassidy had practiced with me and soon he was uttering the incriminating words that Aaron would capture and that when played back would clearly indicate that he had tied Cassidy up and that despite her pleas he would soon rape her.

Within half an hour it was all over! I had adjourned to the twins' bedroom with Aaron and lost my virginity around the same time as Cassidy had lost hers to David. David left happy, undoubtedly thinking that this had been his lucky day, the day when he had finally succeed with Cassidy where all others had failed!

The cock tease had experienced cock and David had obviously enjoyed the fantasy role play. I too had enjoyed cock and I know that as humiliating as her situation was there were aspects of enjoyment in Cassidy's deflowering just as there were in mine.

Another reason for the delay was that I had been neglecting my school work, what with babysitting and hunting down all these boys. I barely squeaked through with the lowest possible non-failing grade on an important test. I had to slow down the pace of the hunt so that I could devote more time to my studies.

I was still pretty distraught about my school results when later that week I dropped by Aaron's house after school on one of the days that Mrs Cabane only worked a couple of hours after school finished, so Aaron was allowed to be alone in the house for this short time.

When I arrived Aaron sensed my despondency and quizzed me until I confessed the reason for it.

Aaron commiserated with me, taking me lovingly in his arms as I related in detail my tail of woe.

I still don't understand how the next actions happened or how Aaron so easily overcame my resistance, but when I had finished, Aaron very gently told me that I knew what had to happen!

The blank look on my face prompted Aaron to say "a naughty little girl, just like a naughty little boy, needs to get spanked"

I was silent for a long time as Aaron hugged and caressed me breaking down my resistance. I knew that if it was one of my baby sit charges I would have said the same thing, but me spanked, I couldn't accept that, I was a girl, I was always in charge!

Just as I was about to dismiss his suggestion outright Aaron said, "A spanking is what you really and truly need, Caitlin but you have to ask for it yourself. I am not going to force you; you have to agree to it.

Suddenly I was sobbing like a little chastised girl! And blubbered out without thinking, "Yes, you're right Aaron, but please be gentle with me as it's will be my first spanking!"

"Of course" He replied with a hug.

Before I had time to object Aaron stood me up and began to strip me of my clothes like I had done to him so many times. I was sure Aaron was joyful at getting back at me but he showed no signs of gloating over his victory. First he undid my blouse and skirt and then had me kick off my shoes leaving me in just my underwear. Next my bra fell as he unhooked it, exposing my C cup breasts and allowing him to lean forward and kiss each of my erect nipples. Then he rolled down my panty hose until he could pull it off my legs.

All too quickly I was stark naked in front of Aaron.

As soon as I was naked he gave me no time to think, sitting down on a chair he pulled me across his lap.

I was so shocked I did not resist, somehow, I was deep down resigned to suffer my first spanking.

"Why are you being spanked" Aaron asked?

"Because ... I ... have ... been ... naughty." I whispered in shock

As I said this I was thinking to myself, "I'm going to get it, I'm actually going to get a spanking!

My mind turned to all the times I had laughed as I had spanked other boys, chiding them about their screaming and tears. I had never considered that I might also end up over a boys knees, just like so many boys had ended up over mine! As Aaron ran his hand over my exposed bottom I wondered how bad spankings hurt. I wondered if I would cry like a baby in front of Aaron who was three grades younger than me!

I reminded myself that I had to hold still, no matter how much it hurt, I couldn't let Aaron see that girls were not tougher and more mature than boys. As I felt Aaron's hand leave my bottom and rise above my lily white bottom, I tensed and tightened my buns.

I was about to get it!

To say the first spank surprised me with its sting would be an understatement. One moment I was tensing my bottom and waiting for the impact, the next there was a loud, slightly muffled smack and the right side of my bottom was on fire. Aaron told me later he had not spanked for long or hard, but to me who had never experienced a spanking before it was both!

After the first impact I let out a shameful gasp and kicked out with both legs, only to have the left side of my bottom suffer the same fate as the right.

"Ohhhhhh !" I exclaimed as shamefully tears immediately sprang to my eyes after only two smacks. Aaron's response was to deliver more spanks, this time to the lower centre of my bottom that burned all the way into my crack.

Soon to my shame I lost all control and dissolved into incoherent sobs like a little girl. I never realised that spanks hurt so badly! No wonder the boys bawled and screamed when I spanked them!

As Aaron's so called short and gentle spanking continued I began kicking my feet and flailing my arms and gasping for air, hoping some action would stop the burning pain that kept building and building in my bottom.

Finally Aaron stopped spanking and lifted me off his lap. Shamelessly my hands flew immediately to caress my stinging bottom. Much to Aaron's amusement I danced around momentarily, trying without success to rub away the pain.

I was still sobbing, as Aaron lead me to the bath room and made me stand in the bathtub with my hands on my head. I was utterly humiliated as Aaron then ran the clippers through her neatly trimmed pubes reducing them to just stubble before he smeared on the hair remover like I had done to him.

When he rinsed it off, I had a completely bald mound like Cassidy!

Then Aaron made me sit in the tub and he gave me a bath being careful not to mess up my hair while thoroughly but gently washing my breasts and bald pubis.

After rinsing me off, he dried me very gently and then took me back to his bedroom.

There Aaron laid me on his bed and quickly stripped off his clothes before getting close and cuddly with me.

Despite the trauma of my first ever spanking and shaving I felt wonderful!

Soon we were caressing and kissing and before long Aaron put on a condom and slipped into me with my now enthusiastic help. I was in such ecstasy that I blurted out to Aaron the fact that last Saturday was my first time. We kept at it and each of us climaxed three times before we stopped.

Truth was I was quickly becoming hooked on sex with Aaron; I wanted his body more and more and was secretly willing, despite the pain and humiliation, to let him chastise me with more spankings if it meant he would have sex with me. By the time I left I was already looking forward to my next visit.

A few days before the end of the twenty six day home section of Mr Colby's roster I again called in at Aaron's house after school on a day that I knew Mrs Cabane would not be home for about two hours. Because of Aaron's short time at home alone, I knew my sister Tanya was not rostered to call, as I still controlled the babysitting roster. She had taken over as Aaron's babysitter much to his displeasure whilst I concentrated on my school studies. I had tried to convince Mrs Cabane that he didn't need a sitter anymore but she insisted he did and asked me to arrange for Tanya to take over. Her only compromise was to allow Aaron the short two hour periods alone after school.

To make matters worse for Aaron, Tanya was younger than him and she also bought along on my mums urging a new apprentice, her fellow classmate and younger sister of Travis and Wade Haussler, Shari.

On this fateful day I had again submitted to being stripped naked by Aaron as I had done a lot over the last weeks and was prostrate over his lap receiving a ferocious spanking when Aaron paused and uttered a greeting that sent shivers down my spine!

"Well hello girls"

I had not noticed Tanya and Shari enter.

I reacted to Aaron's greeting by attempting to cover my exposed bottom.

Aaron didn't seem perplexed at all in being caught spanking me. I guess he was dressed; it was me who was naked and in the humiliating and embarrassing position.

Aaron pushed my attempt to cover up my bottom exposing my bright red bottom to the girls!

Out of the corner of my eye I could see both Tanya and Shari raise their eyebrows in shock and then grin as they both saw me exposed in the spanking position.

"Caitlin has been a naught little girl and let her school work slip so I have been helping her focus on her school work" Aaron casually informed the girls.

Why did he have to say "naughty little girl", my sister in particular would enjoy nothing better than to see me cut down to size. Already I was worried about her telling mum about Aaron spanking me and the consequences of my relationship with Aaron becoming public.

"In that position she sure looks like a naughty little girl and not a big 9th grade high schooler" Shari commented with a giggle.

"Oh since nearly flunking at school Caitlin is very much a little girl these days, off my lap and show the girls your new little girl look" Aaron ordered.

I tried to object and reassert some authority but the threat to spank me in front of the girls soon had me slowly rising from the relative privacy of being draped over Aaron's lap to standing facing my sister and Shari my bald mound totally exposed!

The girls burst out laughing they moment they took in my new hairless look and at that moment I wished the earth would swallow me up!

My demise from power moved quickly from there.

The girls wanted to see me spanked and when I objected they helped Aaron position me back over his lap despite my fearsome resistance.

Even when I was forced into the spanking position I tried to free myself, thrashing and wailing as befitted a girl who had just been demoted of all power and respect.

"Noooooooo, you caaaaan't! Noooooooooooo!" I screamed like a little girl.

Then to the amazement of Aaron, the girls and myself I lost control and from my raised bottom, piss spurted from between my legs and arched out backwards to land on the floor behind me.

"Such a little girl" Shari exclaimed.

"I should have known you'd do something like that sis, you don't deserve to be my big sister, I should be the one in charge."

"No harm done, she missed me and I can wipe up the floor later" Aaron replied almost cheerfully.

"It's probably just as well she emptied herself out before you started spanking her anyway" Tanya added.

"Please, you can't spank me in front of the girls!" I wailed, whilst trying to escape again.

The girls giggled as my wails dissolved into a squeal as Aaron brought his hand smashing down onto my bottom. Tanya and Shari had to hold on to me for dear life to keep me on Aaron's lap as I thrashed and tried over and over to escape the pain humiliation and embarrassment!

My humiliation and embarrassment didn't end there. When my session with Aaron finished, Tanya and Shari escorted me back home and quizzed me along the way about all the details of my school troubles and how Aaron was helping me out. By the time we reached home my sister had taken total control of me. On top of what she had just witnessed she informed me in front of Shari that she had also found out from Cassidy, who I had confided in, that I was having sex with Aaron.

My world was crashing down around me. My power and credibility were quickly disappearing. Tanya promised however not to tell mom anything provided I did whatever she asked. I hadn't expected this!

In the privacy of Tanya's bedroom to renewed humiliation and embarrassment I was ordered by Tanya to undress again and as soon as I was naked both girls undressed as well.

Tanya was still young but like me she was well developed for her age. Her B cup tits had stiffened nipples and between her legs she exhibited a thick but neatly trimmed bush not that much smaller than mine used to be. Shari was even younger and her breasts were not as developed. Just the same she was not some flat little girl. Already for her eleven and a half years of age she had small, cone-shaped breasts. Her nipples were like Tanya's as hard as a rock. Between her legs I expected to see more hair, both her older brothers were hairy but Shari didn't have much, just smooth skin with a few sparse little hairs scattered about. Her still smooth furrow ran virtuously unobstructed down the middle of the lily white triangle between her legs.

"Guess what?" Tanya announced, "You're going to get to lick out our pussies!"

My eyes snapped open with fear and shock. "What! How do you know about that?" I asked in shock.

"Mum told me all about it when I started babysitting. She says it's a great way for a girl to train a guy to service her needs without demeaning herself to sex, unlike you it would seem!"

"But I can't do that to you"

"Oh you will unless you want mum to know what you have been up to and you will to Shari too. She needs to learn all about it too as part of her training" Tanya replied.

"No please!" I begged.

"Tough titties Caitlin" Shari interjected, "You're such a whinger"

"You're gonna lick my pussy and you better do a good job or I'm gonna spank you harder and longer than Aaron so that your ass is so sore you won't be able to sit for a week" my sister threatened.

As Tanya made me lay on her bed with my legs spread I was already crying quietly.

'Now Shari watch how this is done" Tanya instructed.

Tanya then climbed on the bed and straddling me before sitting down on my chest, crushing my breasts, her wet pussy inches away from my mouth.

Taking my head in her hands, Tanya guided my mouth to her waiting cunt.

"Lick it and make me feel good' she ordered.

I was in total shock that my young sister knew all about this. Reluctantly I flicked my tongue into Tanya's wet hairy pussy. As I did this she pushed further forward, squashing her cunt against my mouth. She held my head steady as she moved her hips up and down on my face.

Despite my abhorrence I licked my sister to an earth shattering climax. I felt her stiffen and cum on my face!

Tanya then helped Shari take her place.

"Open her cunt with your hands," Tanya ordered as Shari pushed her nearly hairless cunt up to my mouth.

"Now kiss her pussy lips and move your tongue about."

My hands spread her open as instructed and my tongue darted in and out as I slurped and licked. My lips formed a vacuum as I sucked her pussy into my mouth. Despite myself I was getting into it. Soon I was moving up and down and back and forth as much as I could, trying to stimulate her clit and pussy.

Tanya stood in front of my wide-open legs, fingering my hairless pussy as I ate out Shari. Tanya's actions caused me to move about and buck as I was fingered fucked by her to a climax. Shari moaned and arched her back as she stiffened and came into my mouth almost at the same time as Tanya bought on my orgasm.

"Lick her clean," Tanya whispered in a horse voice, forcing me to tongue her again. By the time I had licked her clean I had Shari's pussy juice all over my face!

My life had changed dramatically. I was forced to spend the rest of that afternoon and early evening repeatedly eating out Tanya and Shari, being forced to do my homework naked and receiving spankings from them when I did not perform my duties up to expectation! By the end of that session I had lost control of the babysitting roster to Tanya and I knew that I was to become Shari and Tanya's personal sex slave. My little sister was now in control!

The End

With Steam Train's permission, Y. Lee Coyote has written two sequels to The Hunt for Caitlin's Bottom
both of which are available on his website The Coyote's Den using the following direct links:
Caitlin Gets a New Point of View
Aaron Gets a New Point of View