Fem Creepypastas x Male Reader

Blackjack

Sorry for the extremely long delay, some personal issues came up. But I hope ya'll enjoy!

The Next Morning, 11:30 AM

Y/N Pov

I slowly opened my eyes and saw a feminine figure standing over my bed with her hands on her hips. When my vision cleared, I saw Trenda standing over my bed tapping her foot impatiently. She was wearing a long, light brown sweater that went down to her knees with the front unbuttoned. She had a white t-shirt with a black scarf around her neck. She black leggings and black and white Vans.

“Finally you’re awake,” she said impatiently. I slowly got out of bed and asked her, “What are you doing in here Trenda?” She responded, “We’re getting you new clothes. Your last ones were atrocious.” She grabbed my hand and led me into my closet. I said, “What’s wrong with a t-shirt, jeans, and boots?” She commented sarcastically, “What are we high schoolers?” I said back, “I’m old enough to be.” She stopped, when we entered my closet, and turned around and glared at me. “Whatever,” she said, “Let’s see what you have so you can look good for when we do go shopping.”

I watched her rummage through my closet looking at all of my clothes. She eventually picked out a white hoodie with two, red horizontal striped across the chest, faded blue jeans, and red and black sneakers. “Here,” she said as she handed me the clothes she picked out, “This is the best I could find. Now put them on, fix your hair and come to the kitchen.” She walked out of the closet and my room and went presumably to the kitchen.

Mini Time Skip

I walked into the kitchen and saw Trenda sitting at the table waiting for me with a bowl of fruit. “Eat this,” She told me, “You lost a lot of blood last night and you need your vitamins and nutrients.” After I ate, she grabbed my hand and teleported us in the middle of a large, crowded mall. I started to panic from all the people there (hopefully you guys didn’t forget about the social anxiety part Y/N). I thought to myself, “Why are there so many people here!? And why am I hiding behind Trenda!?” Trenda looked down at me and gave me a confused look until it clicked. She said, “Oh! You have social anxiety don’t you?” I just nodded my head.

“Just come with me and stay close if you have to,” Trenda said as we began to walk to the nearest clothes store.

Time Skip 2:30 PM

Trenda and I just go home and into my room from what seemed like shopping forever. But, I now have a lot more new clothes and they all look good on me too. As we were hanging up all of my new clothes I said as a hugged her, “Thank you so much, Trenda! I love all of the clothes you picked out for me.” Trenda blushed. “By the way,” I continued, “The girls and I have been planning a game of Blackjack for a while now. You’re invited to come if you want to, along with your sisters.” She responded, “Hmmm, I’ll think about it. I’ll let my sister’s know though.”

“Alright, I hope you all can make it,” I said as she walked out of my room. She left and closed the door behind her leaving just myself in my room. “I got nothing else to do,” I thought to myself, “might as well just chill in here until the game starts.”

Time Skip 8:00 PM

“Y/N OPEN UP!!” I heard someone shout outside my door as I shot up from a nap. I look at the clock and see that it’s already eight o’clock. “Ah shit,” I mumble to myself as I get out of bed and sleepily moved to my door. I opened it to see Clockwork and Jane waiting with their arms crossed and a slightly angered look on their face. “About time,” Jane said, “We’re here for the game we’ve all been planning.” I groggily motioned them to come in since we were having the game of Blackjack in my room.

After about thirty minutes of waiting for everyone else to come, Slenda and her sisters walk into my room. “You made it!” I shouted gleefully. “Yes, we d-” Slenda was cut off by Offenda, “Alright kiddies we’re going to make this interesting. Tonight we aren’t just playing Blackjack for gambling. We are playing strip Blackjack (A/N: Roll with it. I don’t know how to play poker but I know how to play Blackjack).

I looked around and saw everyone glancing at each other and eventually all looking at me with slight blushes on their faces. Luckily for me, I’m the best of the best at this. We all gathered around a large round table with a hole in the middle. It kinda looks like a giant donut. Slenda teleported into the middle of the table and began shuffling the cards and said, “Alright, so apparently the stakes have changed. The rules remain the same but if you have a lower number than me or if you go over twenty-one you strip an article of clothing off.”

We all took glances at each other again. I was sitting in between Jill and Jess. Slenda dealt everyone two cards face down. I looked at mine and saw I had a seven of clubs and an eight of diamonds. Adding up to fifteen in total. I put on my poker face and said, “Hit.” Slenda dealt me another card and it was five of diamonds. Twenty in total. Jess, Benny, Trenda, and Splenda as well said, “Hit.” Once everyone stood, we all flipped our cards over. Slenda had a nineteen, Jess had a seventeen, Jill had a nineteen, Angel had a fourteen, Jane had a twenty, Jackie and Tami had eighteen, Benny, Nurse Ann, and Trenda had fifteen, Offenda and Splenda had twenty-two.

Slenda said, “Alright Jess, Angel, Jackie, Tami, Ann, Benny, Trenda, Offenda, and Splenda should all know what happens now,” she said as she took off her suit jacket revealing a thin white dress shirt. Everyone who lost this round took off their shirts revealing their bras. I think to myself, “This is gonna be a long game.”

Eight Rounds Later

Nearly everyone was in their underwear, some like Jill, Benny, and Offenda were already topless. Some already naked. Jill throughout the game began to rub her breasts against my arm which made me blush and wake up a certain someone down there. She took notice and whenever her hand was free she would lay her hand on top of my member, rubbing it every once and a while. I had no shirt revealing a bunch of scars from the crash and all the stuff that has happened at the mansion so far. It gained a few stares and sympathetic looks but no one said anything. I also had no boots, socks, and pants on. So I was also in my underwear.

It was about ten o’clock and some people were getting tired. But the girls were determined to get me out of my underwear. “Hit,” I said as I get an ace. Adding my total to twenty-one. Just before we all showed our cards Trenda spoke up. “Before we put our cards down, whoever beats Slenda this round gets to go out on a date with Y/N. Now, if by some miracle Y/N has twenty-one, he gets to choose who he gets to go out on a date with. If someone also has twenty-one along with Y/N gets to go out on a date with him no matter what.”

We all glanced at each other with me getting devilish smiles from some of them. We put our cards down and Slenda read everyone's out loud. “I have seventeen. Y/N, twenty-one. Jess, seventeen. Jill, eighteen. Angel, nineteen. Clockwork, sixteen. Jane, twenty. Tami, twenty-one. Benny, nineteen. Ann, twenty. Trenda, fifteen. Offenda, twenty. And Splenda, eighteen.”

3rd Person Pov

Tami jumped out of her chair and tacked Y/N out of his and hugged him tightly, smiling wide. Some of the girls were upset and began to put their clothes back on, then walked to their rooms for the night. The four sisters packed everything up and left as well. Leaving a Y/N in his underwear and a naked Tami hugging him tightly. “Um Tami, you’re naked still,” Y/N told her being crushed to death by her bear hug. “I kn-know,” She said not letting go. She kissed him on the cheek and got up, making sure to brush her breasts against his face on her way up.

“This up-upcoming S-saturday nigh-night,” She said, “P-pick me up a-at my r-room at five thir-thirty.” Y/N responded with a smile, “Alright, I can’t wait.” Tami nodded and gathered her clothes and left Y/N’s room. Leaving him laying on the floor. He thought to himself, “And now we wait.”

About 1500 words. I liked writing this chapter and I hope you all enjoyed reading it too. Like I said before, issues came up in life and I'm trying my best to work on this. The plan is for next week to have the next chapter. Do widzenia!

UPDATE: I've realised I forgot Tami's stutter in the story. It's fixed now.