A Comedy of AR's

by: Sammderr | Story In Progress | Last updated Jun 21, 2024

Chapter 64
CHAPTER 164 .......... Empathy Day- Part Five – Madeline’s Request

Chapter Description: 2 new pictures added 1/28/24 Images for this story can be found at the following web...... https://sites.google.com/view/comedy-ars-characters/home


(((Message from Sammderr to Alec Leamus, regarding your comment 'Sammantha' in the story "A comedy of AR's".   I'm not sure why none of my replies or comments are getting posted to the board... I'll just add it again here at the beginning of chapter 164 ... here was my reply................................

Yes, the regression of the adult female Sammantha (whose body is occupied by Derrek) occurs when Lake Erie water splashes on her in Chapter 70  (Freaky Friday 16)  ... so it is actually Derrek who experiences being a little girl.   Thank you for your interest in the story. )))


Still holding hands, and with a few jitters, I asked, “Where are we going, Madlock?”


“Behind the maintenance shed … under the bleachers.”


I didn’t say anything more on our walk to the bleachers.  I figured she was leading and I was following … and I’d find out her objectives soon enough.  The aluminum bleacher rows were twenty feet above our heads … and we walked under them until we got to the row that was only a foot above our heads.


Since we couldn’t go anything further, we stopped.  Then we turned and faced each other.  Madeline now took hold of both my hands.  This seemed like such a serious posture, like a couple about to get married … and with my secret crush of all people.


She began, “We’re going to be Derrek and Madeline now, since that’s how we know each other.”


I replied, “Okay.”


“Derrek, there are things I’ve wanted to tell you since the school year began … but I felt it was inappropriate until a day like today.   I feel confident enough now to tell you how I really feel.”


I swallowed hard and replied, “Okay.”


“Since the first day of school, I’ve always thought you were a beautiful, handsome boy who was so nice and so generous.  I could hardly believe that of all the girls in school, I was the one who got to sit next to you in most classes.”


Now I was really getting uptight.  “Okay.”


“You might as well know the truth now, Derrek.  Since the beginning of school, I’ve had a secret crush on you and it’s been driving me crazy.  But I always thought you were out of my league.”


I squeaked, “Really?”


“Oh, yes.  It was like you were this wonderful and perfect boy-next-door and I was just plain old Madeline.  On that first day, I was dying to be your lab partner in Biology.  But Hoshiko jumped in front of me.”


“I’m sorry.”


“No, it’s okay, Derrek.  At first, I was mad at Hoshiko, but as you can see, the two of us have become ‘besties’.  She’s a really nice person and a class act.”


I nodded.  “She absolutely is that.”


“But Derrek, I can’t help it that every night, I go to bed thinking about you.”


(This was getting really heavy and I wasn’t sure where it was going to lead.  The last girl who was so ‘into’ me was Sally Sukkemsilli, and I remembered how that ended up.)


“Derrek, I have to lock my bedroom door when I get undressed and spread my legs on the bed.  Girls masturbate too, you know.”


My eyes widened.  “They do?”  (I decided to play along innocently.)


“Yes, there’s a sensitive patch of skin near the opening of my vagina called a clitoris.  And every night, I rub my clitoris back and forth till it gets me really excited sexually.”


“You do?”


“Yes I do, Derrek … But the whole time I’m doing it, I’m really thinking about you … that you’re putting your penis inside me and getting me so worked up, that I have a sexual orgasm.  Do you know what that is?”


“I think so … And girls have them too?”


“Yes we do, Derrek … And that’s why I’ve brought you here today under the bleachers … I want to ask you a favor.”


(Oh shit … this is the worst of the worst.  I’m a 28 year old adult man and I’m about to be asked by a tweleve year old girl to fuck her brains out for fun.  I mean, there’s nothing in the world I’d probably enjoy more doing than having sex with my secret crush, but somewhere down the road, she could discover who I am and send me to jail.)


“This is the only day we can do it, Derrek.  Will you please do me this one little favor … just this once?”


(All this time since the start of school, Madeline was my secret crush and I was her secret crush and neither of us knew it.  Maybe that was for the best.  Sammantha warned me to absolutely not get romantically involved with any twelve-year-old girl.)


She squeezed my hands tighter and said, “Please, Derrek?”


(What a no-win situation I was in now.  Either commit the worst social transgression by having sex with a minor … or refuse Madeline and have her hate me for the rest of the school year … while she still sat beside me in every class.  I don’t know what to do.)


I quiety murmured, “What kind of favor, Madeline?”


She answered, “I want to fuck you.”


“Wait, what?”


(What the hell?!!  What the fuck?!!  All this time she was leading me into thinking that she wanted me to fuck HER, but instead, she wants to fuck ME???  I suppose I wouldn’t have to go to jail for that, but still … this is the third time today that a girl had desires to rape me … What a crappy day this has been.  I suppose if it has to happen, it might as well be with Madeline.)


“I’ll be very gentle … You’ll see.  I even brought a packet of Vaseline so I can slide in and out of you very easily.  I had to ask you now because this is the only day that I get to be the boy.”


(But you’re a fake boy!  Isn’t it extremely humiliating for a real boy to get fucked by a real girl?  I know she’s my secret crush, but won’t that just make it worse?)


“I think you’ll enjoy it.”


 (I don’t think that I’ll ever enjoy looking back at our ‘first time’ just to remember bending over and being de-flowered by a middle school girl.  Is this why I came to middle school?)


“Derrek, I would never do it without your consent because I’m not like the other girls in this school.  I really like you a lot.  I won’t say ‘love’ yet … but I can say that I love the curves and the muscles on your form.  You’re just twelve years old and yet your body is so delicious.  I want it badly and I promise I’ll never ask you again.”


My boner was getting so hard.  “Madeline, what would you use for this?”


“During the week, Starline and Duchess were passing out cheap, strap-on penises to all the girls if they decided to use them on Empathy Day.  The rubber penis is on the small side, so it shouldn’t hurt at all.”


Madeline took the phallus out of her pocket and showed me.  She was correct on the size in that it was only maybe four inches long and fairly narrow.


“Would I have to suck on it first, like giving you a blow job?”


“Oh no, Derrek.  This would be a purely physical expression of our sexuality, something we would both enjoy, and I would tell no one.  It would mean a lot to me if you consented.”


I must have looked like a sad little girl standing there next to my boy crush in a little dress with fake boobs.  But since I, as an adult, wouldn’t be psychologically harmed by this encounter, and if Madeline kept her word of secrecy … I decided to get it over with.


“Alright,” I quietly whispered. 


I swallowed my pride and readied myself to ‘take one for the team’ … by turning and facing the field through the bleacher slats.   Then I slid my panties down to my ankles and stepped out of them.


Madeline giggled when she saw my red stained sanity pad in my panties.  “Hee hee, Derrek, I didn’t realize you were having your period.”


I waited while Madeline fumbled around attaching the strap-on device to her pelvis.  Apparently, she never had a penis before.  I heard a ‘squishy’ sound as she applied the lube to the phallus.


I obliged the girl by bending over and putting my hands on my knees.  Then she came up behind me and lifted my dress … which let quite a good breeze in, refreshing my ass.


(The move she just made reminded me of a quarterback coming up behind his center and lifting up his towel before sticking his hands under his butt and calling out ‘Hut’.)


I gritted my teeth as I prepared myself to be penetrated.  The first touch of her rubber thingy felt cold and wasn’t even lined up straight with my butt hole.


“Derrek, I’m going to need to apply some lube directly on you, so hold still.”


(Oh god, this was so embarrassing.  Her dainty little finger was rubbing copious amounts of Vaseline on and in my anus.  I tried not to cry.)


Madeline pushed forward again, and this time, her fake penis found my hole.  She held my waist and pressed forward, half way at first, then all the way.  It wasn’t too painful … just uncomfortable … like I would need to go to the bathroom for a number two.


Then she slowly began her piston motion, moving her tool in and out.  Okay, so far, it wasn’t too bad.  It was just a matter of how long she wanted to keep this up.


Then suddenly, her rhythm changed.  She started plunging into me with much more force and with greater rapidity.


“Ummmph.”  I grunted when her phallus pressed hard into my prostate.  Then she did it again.


“Ummmph … Madeline,” I said, “Can you ease up a little bit?”


“Couldn’t hear you, Derrek,” she replied.


“Ummmmmmmmph.   Madeline, you’re starting to hurt me inside.  You need to ease up.”


“Why?” she asked.


“Ummmmmmmmph.  Because it HURTS!!”


“Good, it’s supposed to hurt,” she flippantly replied.


Now I was feeling more like a victim of date-rape.  She said she would be gentle.  She said she wouldn’t bully me today.  My rectum was getting really sore.  I thought that being butt-fucked by a girl wouldn’t be this traumatizing.


Maybe I was wrong.  Maybe I should reassess my relationship with Madeline.  For the rest of the school year, I would have to sit next to my rapist in almost every class.  How could I face her, knowing what she did to me?


“What do you mean?!!!” I yelled in pain.


Then she lectured, “Derrek, almost every time I go to bed, I have nightmares about that gun blast in our homeroom.  I wake up startled thinking it just went off again in my bedroom.  You scared me so bad that day.  You could have shut the door to keep Sally out.”




“But instead, you had to play the macho man and stage the ‘Gunfight at the OK Corral’.  You were no hero.  All you did was get lucky that day.  Sally had six bullets.  She could have killed you, me, Hoshiko, Miss Premo, and two of your football teammates.  But you didn’t care.  All you cared about was your selfish revenge.”


I now understood perfectly why Madeline was carrying out her own revenge against me.  And, unquestionably, she was right and I was wrong.  There was nothing I could say to apologize or defend my actions.


If she’ll now hate me for the rest of the school year, then so be it.  I brought this on myself and the only right thing to do now was to allow her to finish her revenge … to let her get it out of her system now … regardless of how long she’d abuse me.


“Fuck me HARDER, Madeline!!”  I called out.






End Chapter 64

A Comedy of AR's

by: Sammderr | Story In Progress | Last updated Jun 21, 2024


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