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The following story is fiction about a youth humiliated publicly as punishment and then rehabilitated.  The story contains scenes of spanking and humiliation.  If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.

This a sequel to Steam Train's story "The Hunt for Cassidy's Virginity" which should be read first. In this section we hear from Aaron again.  This time he is writing right after the events unlike before when he was looking back from some seven years later in Aaron and His Babysitter.

This work is copyright by the author and commercial use is prohibited without permission.  Personal/private copies are permitted only if complete including the copyright notice.

The author would appreciate your comments – pro and con, including constructive criticism, and suggestions.  Please take a moment to email.

Caitlin's Saga
"A" Is for Aaron and Alpha Male


It was very exciting not only seeing but assisting the Turner twins, Eli and Jacob, punish Cassidy for being a card-carrying bitch.  Along with Caitlin, the Twins and I had ganged up on Cas to teach her a lesson.  She had been stripped, her mound shaved and she had been tied up waiting for David Colby to teach her an additional lesson for being a habitual cockteaser.  What David did not know was that there was also a plan to get an incriminating video of him with Cas so that his mother and Caitlin could get him into a behavioral management program.

The exciting and instructional preliminaries were over and I was alone with Caitlin in the Turner's kitchen while the Twins were having great fun playing with Cas' freshly shaved sex thus keeping her fully aroused and orgasmic while waiting for David.  I had observed that Caitlin had not only noticed the bulge in my jeans but was fascinated by it for she kept eyeing it.  I could see that her checks were flushed and even smelt her arousal.  I'm certain that I was putting out pheromones of my own arousal.  I understood my own excitement for I had at long last gotten to see and even to touch a mature girl's sex.  (I had previous gotten a feel of the little titties of a few younger girls.)  I was less certain about why Caitlin was so turned on.  After all, she had seen all of us dressed males today naked before and surely a lot of females including herself.  Frankly, I really did not care why for I hoped that it would make her less able to resist my advances.

One of the things that had gotten mentioned in sex class, was that we guys have to be careful which head controls our behavior – the one on top of our neck with a brain or the one-eyed one always intent on probing hot, dark, wet holes.  Could girls have a similar problem – get them sufficiently aroused so that their hooded clits take over?  If so, then the odds of my getting on base with Caitlin had just sky rocketed.

"Caitlin," I said, "let's go upstairs and watch on the Twins' 'puter.  We don't want to risk scaring David away."  She agreed and in a couple of minutes we were upstairs watching.  It was just in time for David then rang the bell.  The Twins let him in and told him the planned story.  With Cas all trussed up, David driven by his one-eyed head did not ask any questions but stripped and, after putting on a condom, proceeded to have his way with the tied down, freshly shaved, cockteaser Cassidy Di Medico.  I certainly felt that she deserved all that happened to her as she had been the one who had covered me with the depilatory that first time when both Mike and I lost our pubes and got bathed together.

Far more important was that Caitlin was really super excited.  It was obvious as her heart was racing, she was flushed and panting.  We were sitting next to each other on the bed watching and I made my advance.  I put my arm about her and pulled us together for a kiss.  I knew if she was in her usual state, she would have pushed me back and slapped my face for being fresh.  Then she would have spanked me long and hard.  I was betting that she was so aroused that she would kiss back.© YLeeCoyote


She kissed back far better than I expected for she opened her mouth and touched my lips with her tongue.  My mom did not raise any fools, so, like the courteous gentleman I am, I allowed her to enter and we dueled with our tongues.  I was on FIRST BASE with an older woman for the first time.  No matter what happened, or did not happen, next could never change that I was already a winner this day.  But I wanted more and was certain that Caitlin did also.

I slipped my hand under her blouse and felt her breasts still covered with her bra.  Her nipples were already hard as I could feel them through the silky cloth.  "How could I get further?" I wondered.  I had to open the clasp at the back.  Caitlin gave me the answer for she grabbed my crotch so I moved my hand down her back and then back up now under her blouse to undo the hook while continuing to fondle her.  I immediately got my hand inside the cup for an honest feel.  I practically came in my jeans.  Caitlin was as hot as I was for she opened my belt and jeans, got her hand into my boxers and started to play with my rock hard cock.  We were still kissing and I pushed her back on the bed while she continued puling my cock.  I slipped my hand under her skirt and found her panties – soaked with her juices – covering her wet sex.  I pushed them aside and felt her trimmed pubes and then her lips flanking the entrance to her sex tunnel.


As I played with her sex, she was moaning even more than Cassidy had and that was great.  Things were going smashingly but I had a problem.  I had to get the condom on without giving her a chance to stop this wonderful encounter.  I reached into my pocket and pulled it out.  She gave me the opportunity as my playing with her hooded head drove her over the top with a scream.  This broke our kiss and gave me the chance to tear the packet open.  Since my fingers were coated with her juices, I got a good whiff just then.  As I pressed our mouths together once again I could feel my cock harden even more.  I rolled the condom onto my cock as Caitlin continued to play with my shaft.

I was ready and she certainly was just as anxious as I was.  Her little head was definitely in full control of her and I did not care that we were mostly dressed.  My cock was rampant and free while her pussy hole was available and pulsating.  I brought her to the edge again and then got on top of her, pressed my hard shaft into her throbbing hole.  If I was crude, I would have said "that I mounted" her.  She was soaking and with the lube on the condom I slipped right into her pulsating tunnel with surprising ease.



WOW!  A home run!

I doubt that I was the best fucker for this was my just my first time.  I certainly did not last very long before filling the condom and driving Caitlin over the top.  What was important was that I was no longer a virgin and Caitlin could not honestly claim I forced her since she never objected.  When she recovered after her massive orgasm she was, however, furious but what happened could not be undone.  She was, thankfully, mollified because I used a condom.  "Only irresponsible kids don't use protections I reminded her.  I'm certainly not ready to be a father – yet." I explained maturely.  Caitlin was big on maturity and I hoped that she would act maturely.

"You are still a very naughty boy, Aaron." she declared.  Well, I knew what that meant.  I did not want her mad at me, so I stood up and lay down across her lap without a word to placate her.  She did not waste a second, for she immediately grabbed my waist and started to spank me with her other hand.  She did not have it in her to really spank me (which she certainly could do when she wanted to) at the moment so it was not much more than a birthday spanking but it allowed her to release her anger.  I promised to be a good boy for her as always.

Caitlin said that I should not talk about this and I told her that a gentleman never does.  We hugged.  Caitlin went downstairs so that she could comfort Cas.  I quickly saved all the videos that I had recorded and uploaded them to a secure site to deal with later when I had more time.  I even completely deleted them from the Twin's 'puter to assure that they did not get spread about.

* * * * * * * * * *

I saw Caitlin the next day at Travis' coming out party.  Outwardly she seemed the same and was definitely enjoying turning Travis into a little boy.  As you would expect, I saw her as the woman I had ravished.  I imagined that she saw me differently as well.  I sensed some relief in Travis' brother, Wade, as disaster after disaster befell his bullying big brother.  Of course, that was mixed with the horrible thought that it could happen to him as well.  I resolved to help him prevent his brother from bullying him ever again.

Over the next week I realized that all of us had changed.  I felt that I was now a man (certainly in the animal sense) since I had fucked a mature woman.  Even though I did not talk about it (as I promised Caitlin) it was enough that we knew that I had.  It definitely made me more self-confident in every aspect of my life.  I even brought a big box of condoms now that I was not a virgin just to be prepared.  I felt that I knew why both Cas and David were different even though they were not virgins either.  Cas had lost her pubes and been subjected to some pretty humiliating experiences at the hands the Twins and myself.  Her peer David not only used his hands but penetrated her with his shaft while she was bound.  David who had always followed Travis now became very much an alpha male who thought he was a warrior king.  Little did David know at that time what a high price he was going to have pay for his brief sexual triumph once Caitlin, Cassidy and his mother got their claws into him.

It was Caitlin who had me completely puzzled.  She was different.  She quickly calmed down over my fucking her as she had to admit to herself that she desired it as much as I did.  Yet, she was changed and a lot less standoffish when I wanted to be with her.  Not only did she consent to go to a movie midweek with me but once there she raised the armrest between us so that we could get close.  Rather than make her back off I stuck a handkerchief in my boxers so that I wouldn't mess my pants from her most pleasurable groping.  Of course, I had my hand in her wet crotch as well.  I don't remember much of the movie but it was definitely NOT a waste of money.

Unfortunately, Mom did not think I was a man or even a youth who could be left on his own and she still had Caitlin over to babysit me.  Caitlin was pretty distraught when she dropped by after school on Friday for her gig.  After what had happened last Saturday she could no longer think of me as a little boy so I was not unhappy that we would be alone in my house for a few hours.  She was not her usual very confident self partly because of our new relationship and also because of a messed up test and a paper (it got a grade of DO OVER).  She need some comforting.  I was delighted to help her without question.  I held her lovingly in my arms as she related her tail of woe including confessing neglecting her primary responsibilities – those of a student.  When she had finished, very gently I told her that she knew what had to happen – a naughty little girl, just like a naughty little boy, needs to get spanked.  She was silent for a long time as I hugged her.  She knew that I had told her the truth as she had told so many others.  Although she didn't object but she couldn't quite accept it either.  I wondered if our punishing of Cas, let her accept that girls were not so perfect in negation of her mom's beliefs .

"It is what you really and truly need, Caitlin.  But you have to say it yourself."  I prompted her.  I could not force her so she had to agree to it just as she had made others agree usually with some sort of blackmail.

She sobbed when she whispered.  "Yes, you're right, Aaron.  Please be gentle with me as it will be my very first spanking."

"Of course." I said with a hug.  I got her standing and then began to strip her like she had done to me ever so many times.  I had feelings that were at both extremes – just doing an unpleasant duty as an authority figure and joyful as getting back at her.  I undid her blouse and skirt and had her kick off her shoes leaving her in just her underwear.  I could control myself because I had fucked her and I also think that made it easier for her.  Her bra fell as I unhooked it and I couldn't resist giving her a kiss on each nipple.  Then I rolled down her panty hose until I could pull it off her legs.  She was stark naked in front of me.  I was tenting my jeans, of course, but she did not seem to notice this time.

I sat down and pulled her across my lap.  She did not fight back having, somehow, resigned herself to all this.  Perhaps because she had heard all those lectures she gave to her clients, she knew what was right.

I held her about her waist and caressed her beautiful butt.  I tried not to think of how close her slit was to me but only about her curvy alabaster bottom.  "Why are you being spanked, Caitlin?" I asked.

"Because …  I …  have …  been …  a … little … naughty … girl." she whispered.

Then I spanked her.  It was not a particularly long nor hard spanking (like Cas had gotten from the Twins) but it was effective.  I turned her lovely bottom a luscious rose and loved how my hand prints first formed and then merged.  I don't know how I managed not to cream in my jeans.  After a bit she was sobbing and then she cried.  It was the crying of release that she needed.  I continued to spank, but not very hard so that she would cry enough.

While she was still sobbing, I lead her to the bathtub and made her stand with her hands on her head.  I ran the clippers through her neatly trimmed pubes reducing them to just stubble before I smeared on the hair remover like both she and Cas had done to me.  I rinsed the terrible stuff off and then had her sit in the tub.  I gave her a bath being careful not to mess her hair while thoroughly but gently washing her beautiful tits and bald mound.  After I rinsed her off, I dried her very gently and got her back to my bedroom.

I put her on my bed and quickly stripped before getting close and cuddly with her.  It felt so wonderful.  She liked, no, loved it also as she was very responsive hugging me back.  I was very gentle with her; carefully caressing her and kissing her all over.  She responded in kind.  Fortunately, I had my condoms in the night stand and quickly put one on before sliding into her with her enthusiastic help.  We kept at it for a while and each of us climaxed three times.

I learnt something important about her for she made two comments about how "this time was better than our first time" and "my first time".  I put this together with the fact from sex ed class that a woman always bleeding on her first intercourse is a myth and concluded that they were the same event and she had been a virgin just like I was.  I had gotten her cherry!

* * * * * * * * * *

I must have been terribly confusing for Caitlin.  I was not anything like she had experienced.  I was no longer an immature, little boy who needed to be spanked regularly.  Nor was I a male chauvinist pig cretin who bullied everyone – especially women.  I was neither the class jock nor the class nerd.  What she become aware of was that I was in charge of her rather than she in charge of me.  Functionally, I was both a father, confident and mate to her.  She turned to me to function as all three at different times.  I made suggestions and she took them.  If I had said the same things as orders she would rebelled like a teenager.  That rebellion she had with her mother rather than with the man who had taken both her virginity and her pubes and made her his gentle little pussy.

I encouraged her to give up babysitting until she caught up with her school work.  That, strangely, increased my power for she turned the strictness she treated all her charges with on herself with the unforeseen consequence of placing me more under the influence of her younger sister, Tanya.  It took less and less prodding to get Caitlin to ask me to chastise her.  I was always happy to oblige her with a good hard spanking delightfully followed by some hot sex.  Her femdom mom would have had a fit if she knew her dear Caitlin loved to suck my dick dry.

Caitlin even took my side with my mom by telling her how much I had matured (taking the credit, of course) and that I did not need to be babysat as in the past.  I was hopeful, Mom would see things that way since I was almost thirteen, but alas, the best laid plans don't always work out.  Mom hired two girls to replace the young lady Caitlin while she caught up on her school work.  They were Tanya who was Caitlin's little sister, a year younger than I and her apprentice Shari, Travis' eleven and a half year old sister. I was very careful to mind them especially when they wanted me naked and to bathe me.  I did not worry about being modest and it was very easy to dream about them seducing me as they regularly examined my body in the tub while washing me.

With the strict Tanya and Shari looking after me, I had all the incentive I needed to get Caitlin back up to speed at school and to be able to look after me at home. My newly regrown pubes were again looking very threatened.

The Hunt for Caitlin's Bottom by Steam Train

© Copyright A.I.L. November 28, 2010

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Last updated:  September 15, 2023