Windows Ch. 01

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Jill's first taste.
2.2k words
2.42
27.7k
25

Part 1 of the 5 part series

Updated 06/11/2023
Created 03/22/2022
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Asperger27
Asperger27
1,049 Followers

Every day for the past year, I've been having the same dream and it terrifies me to no end. In the dream, I'm drawn to the window in my bedroom. For some reason, I see my girlfriend Jill come in and appears to be talking to someone, who is obscured by wall. Then she starts to stripe, all while smiling naughtily at them.

I try to yell in my dream, but my voice doesn't come. I try pounding on my window, but I can't move my hands. I'm literally stuck in place and forced to watch my once faithful girlfriend get defiled by a guy who looked familiar to me.

Her loud moans only make it worse, along with the constant creaking of her bed and her headboard smacking against the wall. At one point she turns her head and looks at me. Giving me a "you like what you see?" look as she kisses him deeply. Then with a swift motion of her wrist, she pulls down her curtain blocking my view.

I always wake up in sweat afterwards.

I can never bring myself to tell Jill this, nor can I confide in my mom about it either. Because Jill would think I don't trust her, and my mom wouldn't trully understand and say it was just a dream.

Even though I know it was just a dream.

Just a dream.

It doesn't help that I'm always constantly being bullied at school by a guy named Collin Coxson. The guy was the complete opposite of me in everyway. Standing at 6'5, Collin was muscular, attractive and popular.

While I was short, skinny, and a loser.

Which Collin reminded me of everyday.

It also didn't help that every girl at school liked him. I even heard that he even SLEPT with half of them already. At least Jill or my mom don't appear to be fazed by his looks.

Jill. She's been my childhood friend for as long as I can remember. We live next door to each other too. But didn't really start dating until freshman year.

I remember going over to ask her mom's permission to date Jill, as my mom raised me old fashioned like that. Jill kissing my cheek as her mom gave her consent.

She has flowing light brown hair that reached to the middle of her back. Lightly tanned lustrous skin with a dimple on her bottom jaw. Narrow waist, with a shaplely bubble butt and an ample chest. She was a stunner.

She was also a virgin.

We planned on losing our virginities to each other after prom.

Anyway back to the story.

Not a day goes by where Collin doesn't pick on me. Somedays he just demands my lunch money. Other times, he trashcans me and I'll smell of garbage the whole day.

I think my mom knew after the first few times, but didn't say anything. She was the school nurse after all.

But this isn't about my mom...yet. This is about how my girlfriend Jill betrayed me.

Did I mention that sometimes he just pummels me for nothing at all? Like today.

My head hits the back of the wall with a loud thud. I'm seeing stars and feeling nauseated. My right right is swollen shut. Another blow bits my stomach as I crumble into a heap.

"Leave him alone!" screamed a voice to the left of me.

I look up and saw my girlfriend stand in front of me. Blocking Collin from his assault. Her shapely ass a few inches from my face.

"Why are you always picking on him?" she asked angrily, "Leave him alone!"

Collin scoffs and peers down at me.

"You having your girlfriend stand up for you?" he said, "What a fucking wuss!"

He then turns to leave. Jill then kneels down in front of me. Today she wore a light blue blouse with a pair of dark slim-fit blue jeans. Her hair was braided into a single long ponytail, that was draped over her left shoulder.

"You alright babe?" she asks sweetly.

I nod my head weakly. She then helps me stand up and leans into me for support. My right arm pressing into her left breast a bit.

Did she not wear a bra today? Either way, it felt fantastic!

"I'm...sorry for being so weak," I said weakly.

"It's fine Jack," she said softly, "I can't stand guys like him."

She then sighs.

"Let's get you to the nurse's office," she said, "have your mom treat that eye of yours."

Like I said, my mom was the school nurse and took her job very seriously. She was also very attractive. With raven black hair that reached the back of her neck, an hourglass figure and a shapely thick ass. Her breasts were also big too. There wasn't a single guy in school, who didn't want to fuck her.

One happens to be Collin. He's always goading me about what a hot piece of ass she was and how he is sure to fuck her good, after he fucked my girlfriend.

As we entered her office, mom rushed over to me and forces me to sit down on the folding bed she had in her office. She then looked at Jill. Worry in her eyes.

"What happened?" she asked.

"It was that asshole Collin again," said Jill.

Mom sighs and rubs her temples.

"Something has to be done about this!" mom said getting upset.

"I'll have a talk with him Mrs. Swithsen," Jill said.

"Jill...don't," I said, "it'll only make it worse."

"Trust me Jack," Jill said and gives me a soft kiss on my cheek.

"I...do," I said, "but I don't want you getting hurt either."

"I'll be fine," she said with a smile, "let me handle this."

She then left the nurse's office and went to class. Mom tells me to lay down and placed a ice pack over my eye. Why do I feel sp uneasy?

As school ended for the day, Jill came in and asked to talk to mom privately. Mom looked over at me and then said follow me.

They then went into the teacher's lounge for a bit. I wonder why Jill looked upset and nervous.

They came back in and mom sighed.

"You sure you are okay with this?" mom said.

"It's a small price to pay," said Jill.

Mom sighs again and squeezes Jill's hand a bit.

"Just...be careful sweetie," she said.

Jill gives her a quick smile and then kisses my cheek.

"I'll see you later," she whispered in my ear, "I love you."

"I love you too," I said back.

She then left the office. I found out later from my mom, that Jill went to "talk" to Collin.

All the while Jill was gone, I felt nervous. Girls passing-by say in gossip that Collin was a good kisser. I feared for the worst. I never got to go beyond holding hands and pecks on the cheek. I hope he doesn't steal her first kiss from me. I hope nothing comes by her going to talk to him.

I hope not.

Jill came back in half an hour later. She looked dazed, before coming back to her senses and walks towards me.

She then sat down next to me and hugged me. Then said that he will leave me alone for awhile.

"I'm glad you got him to stop" I said, "what did you say to him?"

"Oh you know," Jill said, "told him my mom had connections to the mob."

"Does she?" I asked.

"Course not!" she chuckled.

She then stood up.

"Well I got club now Mrs. Swithsen," she said addressing mom, "I'll see you both later."

She then hurried out of the office. Mom sighs.

"I don't understand why you don't join a club too," she said, "it'll help you make more friends."

"It'll help you man up and stop having to have your girlfriend defend you," is what I heard in my mind from her.

"I'll think about it," I said turning over on my side.

Suddenly my phone vibrates and I fish it out of my pocket. It was a text message from a unknown number.

"Hey I'm sorry for earlier," it read, "so I figured I'd sent you something to help you feel better."

There was another ping and now a video clip appeared. As I opened it, I dropped my phone. On my screen, was a 30 second video of Collin "french kissing" my girlfriend.

"Maybe I'll add her to my collection?" Collin texted a few seconds later, "Just to show how inferior you are to me."

"FUCK YOU" I said in all caps, "LEAVE HER ALONE!"

"Nah dude I don't swing that way." he sent back with a smiley emoji, "I might do her though."

He then sent another clip, this time of my mom in her office. Sitting at her desk.

"Maybe you prefer your mom?" he sent, "After all, she is the school nurse. I wonder how fast she'll cave?"

"Please not her either!" I sent.

He didn't respond for a bit.

"Look forward to more," he sent, "because I'm going to milk that slut for all she's got. Then I'll take her from you."

For the rest of the day, after mom took me home, I laid in my bed sobbing.

Why you may ask?

Because I am a worthless pathetic loser of a boyfriend. Who can not stand up for himself and always depends on his loving girlfriend.

I looked at the video clip Collin sent to my phone. The one of him french kissing Jill.

Just then, I got a text notification from Jill.

"You feeling okay?" she sent.

"I'm fine now." I sent back.

"You want me to come over?" she sent.

"For what reason?" I replied.

"Are you upset with me?" she sent.

"No...just feeling upset at myself." I replied.

"You're fine the way you are," she sent.

"You're just saying that." I replied.

"It's the truth," she sent.

I didn't respond back.

"Look I'll see you tomorrow morning," she sent.

"Yeah." I replied.

"Just know that I'm doing this all for you." She sent.

Sounded like something mom would say.

"You don't have to subject yourself to this for me," I sent.

"I'm not "subjecting" myself to anything." she replied.

Should I tell her about the video Collin sent to my phone?

"I know you kissed him," I sent.

She didn't respond for a bit.

"Did your mom tell you?" she replied.

So that was what they were whispering about?

"She told me reluctantly," I sent.

"Then you know that it was either that," she sent, "or something more degrading."

"Something more degrading?" I sent back.

"Let's just say," she replied, "it was something you wouldn't have liked."

The next thing I heard, was a rapping on my bedroom window. I sit up and notice it was Jill coming into my room.

"I'm sorry for being such a weak boyfriend," I said as I ran my hand up and down her left hip.

"It's fine Jack," she said holding my face between her breasts.

I inhaled her scent. Jill had on that flowery perfume she always wore. It was relaxing to me. I felt my eyes grow heavy as I fell asleep.

In the dream I had, I cane home and saw Jill, my mom and Jill's mom in the living room practically naked. All three sat on the couch as I came in. Then I saw HIM. Saw Collin walk from my mom's room naked as well. A big shit eating grin on his face, as he sat next to my mom and then kissed Jill's mom. Squeezing her left breast as he now sucked on her neck.

Jill then got between his legs and began blowing him. Now only my mom remained left out.

She then notices me and gets up. Pulling me to her and shakes me repeatedly.

"Wake up!" she said.

I was then awake and felt someone still shaking me. It was Jill. Her hair was tusseled about and covered half her face.

"You were having a nightmare," she said.

"Yeah," I said.

"Want to tell me about it?" she asked.

For a while I didn't say anything, just perched my head against her heaving chest and sighed. Finally I spoke.

"It was about you," I said slowly, "plus my mom and your mom. All three of you were taken by someone I hate and used in front of me...repeatedly."

She runs her fingers through my hair. The sensation feels nice.

"Must have been horrifying," she said softly.

I nod my head. She kisses my forehead.

"It was just a dream," she continued, "that will never happen. I promise you that."

She then lays back down on my bed and pulls me down with her. My head still nestled in her cleavage. Her heartbeat was soft and rhythmic against my ear.

Her voice kept repeating in my head as I drifted back off to sleep.

"It was just a dream".

"It was just a dream".

But why was I having a dream like that?

"It's just a dream".

What will happen next?

Asperger27
Asperger27
1,049 Followers
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AnonymousAnonymous9 days ago

@Asperger27

Since you have a gave a description for Jill and Janet (Jill's mom), what does Judy (Jack's mom) look like compared to them?

niggaplz101niggaplz101over 1 year ago

wanna see him mom bred by his bully

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