The sleepless nights at Jack's house.

by Jack-N-Walker


Jack's first outing

When I woke up I got dressed and drank a cup of coffee and ate a toasted bagel. "Mmm. That's the stuff," Afterward I headed to into Ponyville to stock up on food and coffee but on the way I ran into a shy yellow Pegasus who blushed madly when she saw me and hid behind her brilliantly pink hair as she poked her fingers together. "Are you okay Fluttershy?" I was concerned because she wasn't usually this shy around me. 'Maybe I did something wrong' Soon she spoke up.

"Jack would you mind following me. I have something to tell you in private," I nodded in agreement and followed her to her cottage. "Jack. For the past week I've found that I keep waking up with a pair of your boxers in my arms...Not that I mind or anything...And I thought I should return them," She handed me a bag filled with my boxers.

"Thank you Fluttershy I was wondering where these were going. I was beginning to run low on boxers," I turned to exit the house but she grabbed my jacket hood. "Yes, Fluttershy?" She was blushing madly but she finally looked me in the eye and said something that caught me completely off guard.

"Putting those boxers in a bag, and let alone approaching you about it was an embarrassing feat for me. For that I want you to spend the day with me...I mean that is if you want to..." When I heard that I felt my jaw drop and I had the audacity to speak.

"Wh-what do you want with an ordinary person like me, I'm sure there are other guy's out there more fitting of your company than I," I began to shift uncomfortably as she stared at me. Her gaze felt like daggers in my soul, it wasn't a pleasant feeling

"I-I wanted to spend the day shopping with you," I stopped squirming and looked at her with a look of pure stupidity. She had noticed this and began giggling so she let go of my hood and I dusted myself off for no apparent reason.

"Then why didn't you just ask, instead of making this sound so intimate. You nearly gave me a heart attack Fluttershy," I smiled and scratched the back of my head awkwardly as I looked at her.

"I'm sorry...I didn't mean to," She looked at the ground and had misty eyes from the newly forming tears. When the dams were about to burst I cupped a hand under her chin and lifted her chin up so she was staring directly into my eyes.

"I'd love to. Plus I was headed into town to go get some coffee and other things I need daily. Before I ran into you that is. Shall we go?" I held out an arm for her to take but she seemed content to stand next to me. Knowing my gesture was a bit over the top I felt stupid. Almost as stupid as an arrow through the knee.

When we finished shopping I ended up carrying animal feed, shampoo, conditioner and other items I had forgotten because of the weight I was carrying. We quickly made our way to Fluttershy's cottage so I could drop off the stuff and she knew it was heavy. After I set her items in her living room I turned out to face the door but to be met with a kiss to the cheek from Fluttershy whom had been blushing profusely. "Thank you Jack. You're so kind," with that she pushed her way past me and to her room so I stepped outside blushing. A few minutes after I had closed the door it had registered in my brain that Fluttershy had kissed my cheek and I raised a hand to my cheek to make sure I was alive, sure enough I was.

After an hour of wandering around I made my way to my house putting away the coffee and food items for my daily meals. Content with the arrangement of the food articles in the pantry I closed the door and headed to my room and stretched. "Man what a long day," I dressed into my pajamas and sat in the living room waiting for night fall. I got up and began collecting energy drinks and I made myself a PB&J sandwich and headed to my room wishing I had a camera system. 'I'll have it installed tomorrow.' After finishing my sandwich I cracked open the first of many energy drinks to be consumed tonight.

I heard my front door creak open and the sound of footsteps coming down the left hallway. I poked my head out to see Twilight. "NOPE!" I then waited until she was in front of me to slam the door shut in her face. "GO HOME TWILIGHT, YOU NEED SLEEP!"

She was intentionally knocking on the metal to annoy me. "Come on Jack, Let me in these doors aren't as hospitable, or cute, as you," The knocking was beginning to get to me when I peeked out the other hall only to be met with a pair of emerald green eyes.

"Hi sugar cube," I scrambled inside slamming the door button. She began kicking the door and I opened the left door risking my life due to a lack of cameras and I was relieved when I saw nobody out there.

"Oh thank Celestia," I sat in my chair. "Please let her be gone," I opened the right door only to be met with Fluttershy. "AGAIN NOPE!!!!!!!" I slammed the door shut again. "Why me....Why not my two other friends that happen to be male....They, at least, are dating material," I was answered by a purple bookworm.

"We chase you because you push us away when we try to come into your house. It's very sexy. I can only imagine all the things I'm gonna do when I catch you," I died a little inside when I heard her speak and I slammed the right door open to see Fluttershy and Apple Jack waiting patiently.

"Please forgive me you two." I pushed the farm girl and animal lover into the wall and began sprinting. "THIS IS WHY I NEED A CAMERA SYSTEM!!!" I had gotten no further than 500 yards from my house before a rope entangled itself around my leg causing me to fall forward. "NO NOT LIKE THIS!!!!! I WANT IT TO BE CONSENSUAL!!!!!!!" I dug my fingers into the ground and surprisingly I held my place as the rope tugged on my leg.

"Sugar cube, You're makin' this hard on me. Now let go before ah have to make you," She began advancing on me keeping the rope taut. she had gotten a stones throw away before all three girls had gotten in a fight over who got the first turn with me.

'Oh Celestia....Help me...' As if my prayers were answered the rope around my leg had slipped loose allowing me to get up and run into the Everfree Forest. "I might just survive," I made a circle around to my back door of my house and ran to my safe room and before long all three girls were entering my house calling my name trying to be as seductive as possible.

"Jack, You are going to love me," Fluttershy was advancing in the left hall whilst Apple Jack and Twilight came from the right.

"THESE ARE NOT THE DROIDS YOU'RE LOOKING FOR!!!!!!!" I pushed both buttons to close the door a bit harder than necessary, but nothing would be taking my virginity tonight even if I had twenty percent battery and it was four in the morning. "Come on I'm gonna be screwed if they stay there any longer." Thirty minutes passed before the noise had stopped so I opened both doors, relieved to see nothing there. I had assumed Fluttershy had made her way to the guest room to steal more of my boxers, as Apple Jack and Twilight were headed to the front room. It was quiet for another hour and twenty five minutes before I had realized Fluttershy was staring at me from the right hall way. "DEAR SWEET CREATOR OF DUNGEONS AND DRAGONS!!!!" I closed both doors and the night went by without a single sound and Six o' clock came around.

'That was too close...I need to go get that camera system installed.' I chugged the rest of my fouth energy drink. The other three had been consumed during the time I had been waiting for an hour and twenty five minutes.

Running on no sleep whatsoever I got dressed and made my way to the electrical appliances store and met my friend Frost Nightwing or as I shortened it Frosty. He was an average height Pegasus he looked pale with electric blue hair and had three freckles on each cheek in the shape of triangles. "Oy Frosty I need cameras to last the night,"

"Oh getting kinky are we Jack??" He chuckled at his joke and motioned for me to follow him. He was significantly shorter than me but what he lacked in height he made up for in speed and agility.

"Oh ha ha ha Frosty, that was hilarious maybe you can be a stand up comedian some day," I smiled as he handed me the cameras "How much do I owe you?"

"One hundred and fifty bits," I smiled and pulled out my bits pouch and gave him the exact change. "Also the next time you see Rainbow could you tell her to come find me...I think I'm gonna pop the question and ask her out," I smiled coyly at Frost.

"I didn't know you had a thing for Rainbow." He told me to shut up and I headed home to install the cameras and monitor system after I thanked him. After I had finished setting up the camera system I had a camera in every room covering all fields of view including one on the wall in front and behind me up near the ceiling. Hey you can never be too safe. I tested the cameras and all of them worked. 'Now I can see Where they are at all times.' I decided to set my alarm to wake me up at eight in the evening and I went to bed still fully clothed.