Raggedy
Copyright© 2023 by Krosis of the Collective
Chapter 1
Coming of Age Sex Story: Chapter 1 - Redheaded siblings get closer than they should.
Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft Ma/ft mt/Fa Consensual Reluctant Heterosexual Cheating Incest Mother Son Brother Sister Father Daughter First Massage Masturbation Oral Sex Pregnancy Big Breasts
In my mind’s eye I could see Michelle from school, the fit teen brunette’s body filling out her tight gym strip and her sixteen-year-old breasts pushing out her t-shirt from under her sports bra. She pulled off her shorts and turned toward me.
“Oh! What are you doing in the girls’ change room, Andy?” she exclaimed, dropping her shorts to reveal her pink panties.
“You’re in the boys’ change room,” I calmly informed her.
She looked around in shock. Nobody else was there to indicate which of us was correct; we were alone. Her eyes dropped to my shorts. “What ... what’re you gonna do with that?”
I looked down. My stiffy was tenting out my own shorts. “What do you want me to do with that?”
“Andy, you got the hand lotion?”
My eyes flew open to behold my older sister, Ann. She had opened my bedroom door and was now staring at me lying on my bed, stiffy in hand.
“Shit! Sorry!” Then she was gone.
My erection wilted like a flower in a torrential downpour. “Fuck.”
Before we go any further, let me explain about the names ... we’re not actually Ann and Andy, but both my sister and I had flaming red curly hair and pronounced freckles, so mean kids at school called us Raggedy Ann and Andy. Google it, or whatever you kids do these days, but at the time this story took place, decades ago, those dolls were still in the collective consciousness so the nicknames stuck. For our privacy, I’ll be using them in place of our real ones.
After bedtime, there was a knock on my door. “Andy?” It was my sister.
“Go away!”
The door opened and she walked in. Of course she did ... my older sister was the pushy one. She was less than a year older than me; ‘Irish twins’, they used to call it when we were a lot less politically correct about everything.
“I’m sorry about earlier.”
“It’s ... whatever.”
She closed the door. “Did you, um, finish?”
“What?!”
“I saw it kinda ... going down...? Did you get it back up?”
“PLEASE go away.”
She stepped closer to my bed. “You didn’t, did you? That’s my fault. Can I...?”
I stared at her. What the fuck?
She sat on my bed “ ... help you?”
I looked at my sister in her nightdress. Like me, she wasn’t very attractive. Aside from the aforementioned red hair and freckles, I was slim and she was kind of ... blocky? Both of us had bad skin and were essentially shapeless. “How ... how would you help me?”
She moved her fingers along my bed covers toward my center. “I could use my hand.”
“Ann, I really don’t...” She had reached my crotch, so naturally my brain stopped working. “ ... um...” Her fingers were finding the edges of my penis under the covers, which was quickly made more difficult due to its sudden growth.
“Ohh,” she sighed as she felt the lump of my penis under the covers. “Can I see it? Again, I guess?” She reached up and I let her pull my covers down, revealing my slim chest and mostly hard cock. She took the shaft in her fingers and I moaned at the sensation.
But my current erection was mostly due to the direct stimulation, as I didn’t find my sister attractive at all, she being so unlike any of the teen girls or movie starlets who caught my eye. “Ann, I can’t...”
She caught the look on my face and looked down at her disappointing body. “I understand ... why don’t you close your eyes?” She began stroking. “What were you thinking about when I walked in on you?”
“Um ... uhh ... Michelle Wright.”
“Oh, she’s pretty ... very nice, Andy...”
I was pretty sure she meant that Michelle was a very nice choice but she could have meant my penis was very nice. I had no frame of reference to know how I compared to other guys. Ann continued to stroke, though it was awkward. My sister had never had a boyfriend, so I was pretty sure she’d never done anything like this before, and it showed. I wasn’t going to cum like this. “Um, Ann ... this isn’t working for me.”
“Yeah, I’m sorry I’m not better at it ... I wonder...”
Then I felt a warm wetness surround the tip of my cock and my eyes flew open to see her mass of red curls down by my crotch. She had put my penis into her mouth! A moment later, she had taken my length and then started to bob up and down upon it. With the aborted masturbation earlier, replaced by my first blowjob, my delayed orgasm exploded. “Ugh!”
“GLLK!” Ann gurgled as she choked on my cum. She pulled back and I didn’t see where my next spurts went. Then she ran from the room, pulling the door closed behind her.
I went to clean up but couldn’t find more than a few drops. I must have covered my sister with the rest of my cum! I put on my pajama pants and tiptoed to Ann’s door, but paused. It sounded like she was crying on the other side. Realizing I had really fucked up, I went back to bed.
I had no chance to discuss the previous night with my sister because our parents were around. Our Mom and Dad looked very much like us, both redheaded and freckly, though Mom had some curves and Dad some muscle tone. I hoped I’d be able to grow into my body like him soon.
Ann and I also didn’t have any time to talk at school because we were in different grades and I couldn’t find her at recess or lunch. It wasn’t until we got home that we were finally alone again.
“I’m so sorry, Ann.”
“For what?”
“For ... doing it in your mouth?”
“It’s okay, you just took me by surprise.”
“So you’re not upset?”
“No, why would you think that?”
“You were crying.”
“When?”
“Last night ... after.”
She smiled and covered her mouth. “Oh ... I wasn’t crying.”
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