Chapter 1: The Induction
My roommate Britney was sitting on the couch watching Love Island when I came home from work. I had always had a major crush on her since the first time we met, but I never had the confidence to act on it. Instead, I had been stuck in the friend zone for the past year. We had met through some mutual friends at a house party, and became good friends not long after. While it was nice becoming close to her, it was never quite satisfying enough for me. In fact at times I almost wish we weren't as close, as she would share intimate details about her love life and all the "boys" she was with to me. I always lent an ear to her and gave her any advice I had, regardless of how it killed me inside.
Britney was a skinny, toned white girl. She had small but perky breasts, usually a turn off for me but on her it worked wonderfully. Her ass was perfectly round and plump, which was surprising every time she turned around since she was so skinny. Since living with her the past few months, I had caught many glimpses of her ass, leading to a nightly routine of jerking off imagining my face being sat on by her. Her legs were toned and long, and always looked amazingly smooth. She had probably close to 40 tattoos throughout her body, though none of them were very large. She was covered in patch work, many small tattoos pieced together. Most were covering her arms and thighs, and her tattoos really turned me on. She always had long, manicured fingernails, which I would constantly imagine gripping my cock. Yet they never did in reality. She also always had a nice pedicure, usually painting her toes white but she seemed to like softer pastel colors as well. I didn't really pay much attention to her feet however, as I was mostly an ass man.
Today she was wearing tight, black leggings with white socks to go along with a white tank top. Nothing crazy but she looked effortlessly sexy.
"You look like you had a rough day" she smirks.
After a long day of work I reply "An 8 hour shift will do that to you."
"Why don't you get showered up and come watch love island with me, I need someone to talk about all this tea with!" she states excitedly.
I nod and go to my room to take a shower. About 15 minutes later I walk out into the living room, ready to unwind. I sit next to her and we watch the show, gossiping every time someone says something cringey on the show.
After watching 2 episodes, she suddenly turns to me excitedly and shouts "I got some cute things at the thrift shop today I totally forgot to tell you!"
I am hyped to hear this, but for a much different reason than her. See, Britney loves to get new clothes often and does little fashion shows to show off her latest hauls.
"Why are we still watching Love Island when we haven't even seen the Britney fashion show yet?"
She gets up faster than lightning to grab her shopping bag. I watch her perfect ass bouncing as she dashes to her room. She walks back in with a giddy smile on her face, as her getting new clothes is always the highlight of her week. It becomes the highlight of my week whenever she actually tries on the clothes, so I always get hopeful that one of the outfits will speak to her enough to make her need to put it on.
"Okay I got like 5 things today, so don't get too excited. But I think I can use a couple of them as a matching outfit. They had a lot of other cute stuff, but none of it was in my size."
The first thing she pulls out is a checkered skirt, which I immediately hope she decides to try on as girls with short skirts means ass hanging out the back. I ooh and aah dramatically, hoping my excitement will get her hyped to try it on. The smile burns on her face, and I can tell she was excited by me reaction.
"I'm so glad you like it! I probably should've started with my least favorite thing but this skirt was my favorite part of the haul and I couldn't wait. These would be perfect to wear on a date or something." she exclaims. Damn, that felt bad but if it gave me a chance to see her in them then I had to hype her up.
I reply "who cares I'm sure all of these are going to be fire regardless, let's see what else you got! Any guy on a date with you would love your fashion."
Next she pulls out a white crop top with short black sleeves.
"Okay but why would those actually go OFF with the skirt!" I blurt out. Not only was this actually true, but I all I could think about was getting her to wear the skirt.
"RIGHT! I literally screamed in the store when I was this." Mission accomplished, the excitement on her face was impossible to miss.
Next she pulled out a silver necklace with a little crescent moon, it looked cheap but I knew she would look cute with it on. This was the most predictable item, as I'd noticed she loved wearing new necklaces all the time. She decided now was the time and slipped the necklace on.
"You know how I am with my moon jewelry" she giggled.
Next she pulled out a black zipper jacket. "This one isn't really that special but you can never have too many jackets" she said. I was underwhelmed but I was not gonna let her know that, "yeah but that'll go with like 30 different outfits so that's a win".
Lastly, she pulls out a tiny plastic bag. She takes out a silver toe ring. The band is extremely slim, wrapping around once and ending with a decently sized flower gem that is glistening green. "This is my favorite green so I just had to get this toe ring" she states. I normally would've shrugged this item off but something about it catches my eye. I am thoroughly intrigued for some reason.
"You need to put that on immediately Brit! That's the best part of the haul without question!" I exclaim.
Uhhhhh what. What did I just say? Why the hell did I sound so excited. How is a stupid toe ring better than a tiny skirt that will guarantee me seeing her ass popping out of the back? I look at her face and she is giving me a quizzical stare. I feel my face turning red but I still have a stupid smile.
"Of all the stuff I got, this one is your favorite for real?" she questions.