Finding Stephanie Ch. 02

I awoke to the sound of my alarm, quickly turning it off so it didn't wake up Kaitlyn. I decided on wearing the one cotton thong I had, only thing was that it was bright pink, but I thought satin or lace would be terrible for the gym. I put on my track pants, the material felt terrible against my ass, it was so rough. I threw on a gym appropriate shirt, went to cook breakfast and make coffee. I made a meal of pancakes with an egg. Kaitlyn awoke earlier than normal, came up behind me as I was cooking, she wrapped one arm around me and grabbed my ass with the other. She pulled down my pants over my ass.

"Nice choice! I like these ones." I could see her smile out of the corner of my eye.

"So... I know what you told me what to buy but I think I need to buy a few more thongs that are made to absorb sweat for the gym... and I also need a couple pairs of new gym pants, these feel terrible on my ass and against my bare legs." I looked at her with the best puppy dog eyes I could manage.

She pulled my pants down all the way and rubbed my legs, "I noticed you shaved your pubes but I didn't notice you did your legs! I approve." she sniffed my body "oh you used my body wash as well, I know that scent!"

"I'm sorry, I should have asked first before using your body wash." I apologized right away.

"It's fine babe! I told you we were going to have to share body wash, I just thought we would have to buy a more neutral scent, I'm glad that we don't have to." She smiled wider. "And to answer your previous question, I'm assuming you are going to be buying girls pants." I nodded, blushing. "Well then I say go for it. You should also buy some tight jeans that hug your ass and lift it up. Just don't go too crazy. You should take my credit card so we can slowly pay it off and keep your savings, so we can put that towards a house."

"That sounds like a good idea to me... one other thing, I think I'm going to go and apply for provincial income assistance... I've been applying for everything that I think I could do and am qualified for, short of going back to McDonald's... You were right, there is basically nothing out especially for entry level positions... it would be best for me to use some of my saved up money to get some IT certifications finally." I explained.

"That sounds like a really good plan babe. I think it's a good use of funds to be able to make more and to have a little extra money every month from the income support would be a bonus." She looked over at the clock and then back to me "Before we eat breakfast, come to the bathroom with me."

I followed her to the bathroom. "Okay, sit down on the toilet, facing the wrong way, like towards the tank." I followed her instructions, sitting down. I couldn't see what she was doing but I heard the spray bottle and then my hair was wet. She started with normal scissors and made a few small cuts, as I could feel only small bits of hair hitting my shoulders and back. After she was done with the regular scissors, she switched to texturizing scissors. She blow dried my hair and then added a bit of product to it. "Okay, all done! Have a look."

I stood up and checked out my new haircut. It was a punkie Pixie cut, short for most women but I thought it looked great, it reminded me of the pop star Pink's haircut. I hugged Kaitlyn, "Thank you, I love it!!"

"You're welcome babe, I'm glad you like it. I think we should dye it something cool like purple, pink or bleach blonde. Although the latter one might make you look like a ghost even more that you already do!" she giggled.

"I think I would like purple but a medium pink would look cool as well." I replied.

She pulled up a picture on her phone of the colour which looked similar to bubble gum but slightly darker, "like this colour?"

"Ooohhh that's really pretty!!" I exclaimed.

"I'll send you the colour code, once I find it and tell you what store to go to, what things all to get cause we will have to bleach your hair first to get it to that colour since yours is such a dark brown. We will dye your hair on our day off tomorrow! But let's get breakfast ate quickly, I don't want to be late for work."

We ate breakfast at quickly as we could, I threw in a pair of jeans and band shirt into a small gym bag and drove way too fast getting Kaitlyn to work on time but we made it. I had a very light quick cardio workout since I had so much to do. I got a few weird looks from some of the guys as I did my workout and went into the change room to get out of my gym clothes. I had forgot I was wearing the thong but one guy in specific noticed and I caught him looking at my ass. He smiled when we locked eyes, I quickly threw on my jeans and shirt, leaving the gym.

I made my way to the mall, made a bee line towards an athletic store. I looked around and there was no staff on the floor, I found a few pairs of girls workout pants of different sizes and styles, I took them to the change room and tried them on. Small was way too tight especially around my waist, large was too big, medium was just right. I found two pairs that hugged my ass nicely and the material was much softer than I was used to. I took them up to the counter and the person there could barely care, just rung me up and bagged my purchases. I went to the Levi's store, it was a bit more difficult process but the girl helping me find pairs showed no judgement. I guess she was used to some guys buying girls jeans especially since emo exploded in popularity. I found a dark blue pair that I loved and of course it was the most expensive pair, so I decided to just get the one. I kept them on rather than changing back into my guys jeans.

I finally made my way to Victoria Secret. It was the most awkward of my shopping experience. When I walked in the girl at the front was friendly enough, asking me if I was looking for something for my girlfriend. I stumbled over my response eventually settling on telling her no. Her face went a bit blank and she wasn't sure what else to say. I walked away rather than have a further awkward conversation. I found my way to where they had the active wear and grabbed 7 different sweat absorbing thongs, figuring it was cheaper to buy more underwear than run the washing machine more than our typical once a week. After that I found a lot of tables of regular underwear. I picked out 5 more thongs as Kaitlyn had made clear was her favorite. Finally I went to the lingerie, I found a really cute set of a satin black teddy with matching panties that I thought would look really cute once my hair was pink. I took my purchases to the front counter, the girl there was much more friendly and didn't ask me any more awkward questions.

I left the mall and made my way to the hair supply store and picked up the things that Kaitlyn had texted me. I then made my way to the income assistance place. It was a difficult conversation but eventually I got approved, it turned out to be only $1200 a month but it was better than nothing plus it came with basic health coverage for things that didn't fall under the national healthcare. I made one final stop at one of the nicer liquor stores to get a good bottle of wine, went home, realizing how late it was, I put together a quick dinner, stripped off my clothes put on the teddy and matching panties, then pulled on my new jeans and shirt back on over top of it. I hopped in my car and went to pick Kaitlyn up.

I arrived a couple minutes late, I apologized to her but she didn't care that I was late. She just leaned over and planted a big kiss on my lips, put her hand under my shirt to feel the silk. It put a big smile across her face. "I can already tell I'm going to like this." She giggled. As we drove home she couldn't keep her hands off of me. She even tried to put her hand down my jeans before realizing they were too tight to do that, so she just rubbed the front of my crotch.

We arrived home and immediately she said, "before you take off your clothes I need a better look at those jeans!" So I stood in front of her and stuck my ass out a bit, she cupped my ass and then gave it a smack. "Those are just about perfect!" she said with satisfaction. "Time to get them off though!"

On her command I stripped off my shirt and jeans, turned to face her, to see the most devilish grin I had ever seen from her. "Do you like my choice?" I asked blushing.

"Its almost perfect!!" she smiled "only thing that would have been better is if I got to pick out what you were wearing but that's something we can do tomorrow!" she seemed to be enjoying this much more than I ever expected.

I served us dinner with a glass of wine, we had a pretty normal conversation about our days, this time I didn't lie to her about anything or leave anything out. When I told her about the guy at the gym, she got this weird look on her face, I wasn't quite sure how to place it.

"I'm glad you got approved for income support, like you said, it's not a lot of money but at least it's something, it will help with the burden on me since that covers almost all of our monthly expenses. I still think it's bullshit that you can't claim employment insurance. We pay into that shit every pay period and yet you can only claim it if you were laid off." She reasoned.

"So you won't have to work six days a week anymore!?" I asked excitedly.

"Well it depends on how much my new girlfriend goes shopping!" she giggled and then stopped, looking at me "I'm sorry I just referred to you as a girl without checking to see how you felt about it first."

"I don't hate it..." I confessed to her "actually I kinda like to be honest." I could feel my cheeks burning red from answering that.

She smiled widely, "So... Stephen... that doesn't feel right anymore does it? Is it just as simple as making it Stephanie or do you have a different preferred name."

"As long as you don't call me by my last name, I know it's a girls name, but James always used to call me that... I never quite understood why. We had been friends since early grade school but he definitely took his chances to demean me." I frowned "I haven't put a ton of thought into it, so as you said, Stephanie is easy... also maybe now people will stop thinking I'm French" I laughed "I don't know that possessed my parents to do that to me."

"James is an asshole, I've only met him the once but I would prefer not to again. I thought Paul was bad." She laughed.

"Wait, you don't like Paul?" I said in a hushed tone "But you always used to hang out with him before you and I started dating."

"Sarah was my friend first and then Paul came along, Sarah was working such crazy hours and with Paul living upstairs, it just became easy." Kaitlyn confided in me.

"I didn't know that... I thought I was the only one who put up with him out of convenience." I laughed.

"Honestly, I think that's kind of everyone... I don't know that Sarah sees in him... where as Sarah is so happy that you are I are together. She hated Tim as well and was actually cheering me on when we were hooking up before he left." There was a bit of sadness in her voice recalling the actions she had taken.

I took another big sip of wine, "I'm glad Sarah likes me... I hope she still does now."

"Nothing that her and I have talked about would indicate that she is a bigot but I guess people can surprise you like your ex." She sighed.

"Oh... I knew she was like that, or at least part of me knew and I chose to ignore it until it hit me square in the face rather than some gay couple she was making fun of. Part of me had hoped she was just old fashioned like my Dad... but nope she was just a straight up bigot." I thought back on my previous relationship getting sad thinking about the year I wasted.

Kaitlyn smiled, "hey you, time to come out of your own head. You and I are together now and I don't see that changing. I love you."

"I'm sorry... you know how I can get lost in thought... I'm sorry for not being present there. I love you too." I apologized.

"It's okay babe. You're right, I do know you and your tendencies, you don't have to try to supress them with me, I just want you to be the best version of yourself!" she smiled again reassuringly.

I smiled back, looking at our now empty glasses of wine, I stood up and grabbed the bottle emptying the last of it between our two glasses. We both had another sip and then I asked, "so what's the plan for tonight?"

"Well you do your wifely duties and get the dishes clean, I'm going to go wash up and get the bedroom ready!" she winked at me. I blushed a bit after hearing "wifely" duties.

She kissed me on the cheek as she downed the rest of her glass of wine and then she headed off to shower. I cleaned the dishes and then I sat down on the couch, looking through Reddit for awhile before I felt her hand on my shoulder. She was naked other than a pair of black panties, her big breasts proudly out and in front of my face. She took my hand leading me to our bedroom.

She had lit all the candles on the raised half wall that surrounded our bedroom. It looked like the second night we hooked up, when we had actually planned it rather than it just drunkenly happening. We fell into our bed, making out, her hands all over my silk teddy and panties. She was grabbing and massaging my pecs as if they were breasts. I had always had a bit of extra fat on my chest, gynecomastia, I hated it as a kid being teased for it. It brought me a lot of shame but now as an adult it was a blessing in disguise having small a cup boobs. We made out like teenagers for a good half an hour.

I eventually kissed down her body, stopping at her boobs to give them and her nipples proper attention. I kissed the rest of the way down to her pussy and ate her out until she came. It didn't even take that long and I could tell how all of this was turning her on. After she came the first time, she demanded I fuck her, and so I did, unfortunately I was turned on too and didn't last as long as I had normally. I felt bad so I went back to eating her out, tasting my cum and her juices mixed together. She came again and brought me up to kiss her lips.

"That was fucking amazing Stephanie!" she said with a big smile of satisfaction across her face. We fell asleep together, her the big spoon cuddling me, it felt good to be held and I slept well.

I awoke before Kaitlyn but got more sleep than usual without the alarm. It felt good to be cooking breakfasts and making coffee in the teddy. As I was cooking, I saw Paul out of the corner of my eye, walking to his car which was parked in the back next to mine, as our door was a sliding glass door. We locked eyes, he just winked at me and got into his car. What was Paul doing awake this early, he usually went to work minutes before. I was a little panicked about it but I refocused on my cooking of waffles.

Kaitlyn awoke as I was almost done making food, she hugged and kissed me from behind, giving my butt a smack, and sitting back down at the table. I served her breakfast and coffee, finished making mine and sat down beside her with my food.

"We might have a bit of a problem..." I started.

"What do you mean?" she replied looking at me with concern in her eyes.

"Paul saw me cooking breakfast just before you got up... he winked at me." I said quietly.

She smiled and giggled a little, "what a horn dog. I wonder what he was doing up so early... but either way it's fine. I would be more concerned if he did something mean or aggressive."

"Yeah... I guess your right. So what's the plan for today?"

"After we are finished eating, I will dye your hair, then you can get showered, I think you should keep your entire body hair free, I like it a lot better! So you've got that to do and then we will head out."

"Sounds like a good plan to me!" I smiled.

We finished eating, we went to the bathroom where she spent the next hour bleaching and then coloring my hair. I got into the shower, giving my entire body another quick shave, when I got out Kaitlyn was waiting. She wrapped my body in a towel and then blow dried my hair, styling it again. As the steam from the mirror cleared up, I could see my hair now. She did a great job, it was exactly like the slightly darker bubble gum pink colour she showed me. I smiled widely.

"Two questions for you... Are you up for me doing your makeup and are you okay with having longer semi permanent eyelashes?" she questioned me.

"I'm good with both of those." I replied smiling.

"Good! I don't want to force you to do anything you don't want to do babe. Go lay down in the bed, I will be there in a second, lay down, further down then you would for sleeping, towards the bottom of bed, so I have room to sit above your head and have it in my lap."

I followed her instructions, she came to the bedroom shortly after with a bunch of individual minx lashes, tweezers and glue. She sat above my head, my head now in her lap. She went to work, it took about half an hour and then she was done with the eyelashes. She then went to shaping and trimming my eyebrows into a feminine shape. We went back to the bathroom, I loved how long my eyelashes were now even if they weren't technically mine. She proceeded to do my makeup, letting me know that we would have to buy foundation of my own since mine was such a lighter tone to hers. I looked in the mirror after she was done and I couldn't believe how good I looked. I didn't look just feminine... I looked like a girl. Having a girlfriend who had a degree in esthetics was a big help, she originally wanted to do makeup focusing on beauty makeup for Canadian Hollywood and weddings, but life changed for her.

I got dressed in pink satin thong, my new jeans and one of my tighter band shirts. Band shirts was practically all I owned except for a few dress shirts that I could wear for special occasions and going out to dinners. She got dressed in a pair of jeans and a tank top. We headed out and she directed me to a nail salon by our home. She didn't even ask me this time knowing my answer would be yes. She told them I wanted a standard French manicure to make them not too long so I could still type. I appreciated that she was that considerate but that was standard for her. I was very happy with my new nails.

I wanted to make a stop of my own and drove to a shop downtown that carried band shirts. We walked around and I found a few shirts and tank tops that were for girls of my favorite bands. I changed into my new AFI tank top as it was an unusually hot spring day. We went to an adult store to see if they had any higher quality lingerie. It was a fancy store and they had this really pretty light blue and white French lingerie, Kaitlyn picked it out. I questioned it cause it was $300, she said not to work about it. As we were about to leave the store Kaitlyn's eyes were drawn to the dildos. We walked over and she started to pick out things. She grabbed a butt plug first, a huge bottle of lube, then a holster and she asked me what dildo I liked best. I picked out a 6 inch realistic looking clear dildo. She approved of my choice but also grabbed a much bigger and thicker 9 inch black skin tone dildo, that she told me we would use when I got used to the smaller one.

I had hooked up with a few guys in the past, mostly blow jobs but I wasn't an anal virgin although none of them had really big dicks, at least not the ones I let fuck me. So the huge dildo caused me to be a bit nervous. We made another stop at a makeup store to get me my own foundation and beauty blender used to apply it. Kaitlyn told me some people used brushes for it but the sponges especially the BB one gave much more even coverage and you could fully clean the blender. Finally we hit up the liquor store and bought a couple bottle of Moscato wine, it's a sweet wine that both of us really enjoy when just drinking for fun rather than a nice pairing with a meal.