Mia's Master Plan Ch. 01-02

This is my first post. All characters are 18 years old or older.

Chapter 1 - "You have to be bold"

It was late Sunday morning when I finally woke up. I brushed my wavy, shoulder length blonde hair out of my eyes as I looked at my clock and saw it was just past 12:00. "Maybe I shoulda watched less sissy hypno last night," I groggily thought to myself.

I rolled out of bed and looked around the room. Women's clothes and makeup was scattered throughout. I looked down and felt my cock throbbing in my chastity cage. I grabbed the key and took it off, deciding to give myself a break. I threw my chastity cage in a plastic bag with a pink dildo, jeweled butt plug, and vibrator. The sound of birds chirping outside my window made me want to go outside. "I'll clean the toys later."

I neatly folded the miniskirt and crop top and hid them in my closet with everything else. I quickly pulled some sweatpants over my thong, slipped on a T-shirt, and put my socks and running shoes on. I quickly checked the mirror to make sure there was no makeup left on my face. When I walked into the kitchen for a glass of water I found my roommate, Jack, already awake.

"Morning Jamie," Jack groaned, hunched over the kitchen table with his head in his hands.

"Long night with the boys?" I chuckled.

"There were girls too," he grumbled.

Despite being a freshman in college I rarely went out to party. I still hadn't lost my virginity, and no girl seemed interested in a skinny guy of average height. The most experience I had with a girl was Annie.

Annie was the only other freshman in one of my classes. We sat next to each other and got along well. She was very funny, and always laughed at my jokes. I guess she was kinda cute too, but nothing like some of the other girls on campus..

Jack finally lifted his head to look at me, seeming taking a minute to comprehend what he saw. "I don't know how you're going on a run right now. Especially in sweatpants."

"Perks of not being hung over," I replied. Though it was a little warm outside, I was too self conscious to wear shorts. I had enough close calls being caught as a sissy and didn't feel the need to show to him I shave my legs.

As I walked out the door I heard him groan "Wait!"

I froze as my heart beat faster in my chest. Did he catch me last night?

"I'm going home for the weekend Friday and won't be back 'til Monday morning. Just thought you should know."

My run began with an extra pep in my step after hearing the news. "Finally some privacy! I can dress all day without having to worry about being caught."

As I jogged through my sprawling college campus I tried to think of ways to capitalize on this rare opportunity. "I could take lots of pics to post online. Film a few videos. Maybe get a bigger dildo and see if I can take it. Play sissy hypno from our living room TV..."

As a strong breeze brushed against my skin, the sun peaked out from behind a cloud and shone right in my eyes. I turned away and saw a girl with jet black hair struggling not to drop some books she was carrying. As the wind blew it lifted her skirt above her waist, exposing her perfect ass in nothing but a thong. I tried not to stare but felt it was a sin to have an ass that perfect and hide it away.

Suddenly she turned her head and her piercing blue eyes looked right into mine. Time seemed to slow as I tried to decipher a complex expression. It seemed both kind and cunning, both friendly and devious. I quickly turned away, hoping she didn't notice me staring at her ass.

Squinting through the sun I saw a guy standing next to a girl on the stone steps of a dorm. She giggled as he spoke. Looking so innocent and sweet as her long blonde hair blew in the breeze with her red sundress. Then as suddenly as the sun appeared, it dipped behind the clouds.

With a clearer view I realized the guy was actually a girl as she leaned in and kissed the other girl right there. "What I'd give to be her," I thought. Then it hit me. "If I can't get a girl to fuck me as a guy, maybe I can find one to fuck me as a girl!"

I thought about it more while I struggled through my post run workout routine. Sweat dripped off my face as I cranked out pit sit-ups, pushups, and squats as I could muster. Afterwards I stared at myself through a mirror while stretching on the hardwood floor of our living room.

The mirror was impressive. It spanned from floor to ceiling and wall to wall. It made the already large room seem larger. It was so large that the old couch, wooden coffee table, and TV stand only took up a third of the room. The rest was empty. I always enjoyed the extra space while stretching. I was deep in thought when my roommate walked in.

"I think cheerleading tryouts already happened," Jack quipped loudly.

My face turned red with embarrassment.

"Yeesh don't be so embarrassed. I almost pulled a hamstring fucking some chick last night."

"Sounds terrible," I replied flatly.

"It actually was. You'd think for seeing me naked and wanting to fuck me that massaging my leg wouldn't be a deal breaker, but apparently it was." He took a deep sigh as he looked out the window with his thumbs in his belt. "Cherish your youth, Jamie, you won't always be so flexible."

"You're 6 months older than me."

"Yes but I'm also a sophomore. I see potential in you, Jamie. That's why I let you live with me despite being a freshman. And since you won't ask out Annie, I'll give you some advice. You have to be bold if you want to get laid."

Jack's words echoed in my head as he strolled out the room. "Maybe he has a point," I thought to myself.

Chapter 2 - "What you don't know can hurt you"

Later that night I put my plan into action. I used Tinder before but never got any matches. Now that was time to change. I deleted my profile and started from scratch.

When setting up a profile the first thing it asked was my name. I hesitated for a moment, staring at the screen as I sat on my bed. "Mia" was the name I typed out. It was the name I used online when I would post my sissy pics.

Next it asked for my gender. I hesitated again and put another lie; "female." Last, it asked for my orientation? I lied again; "gay."

Though I had watched plenty of sissy hypno and flirted with men online, I never actually had been with a guy. There was one late night earlier in the year when I almost did. I still remember him. A linebacker on the football team named Tyrone.

He seemed perfect. Tall, handsome, dark, ridiculously strong. Friendly but assertive. But still, I couldn't do it.

I remember getting all dolled up after setting up a date at his place. Standing alone in my living room, staring at my phone as I stood in front of the mirror. I had the address typed into Uber as my thumb hovered above the order button.

The idea seemed nice when watching hypno and edging endlessly. Yet actually imagining going to his place dressed as a girl? Sucking another man's cock? Then taking that same cock in my ass? Crazy. Repulsive even. I'm straight. Plus the thought of going out all dressed up was too risky. I blocked him without saying anything and went to bed. The last message I sent read "be there soon ;)."

Now my Tinder profile was created and all that was left was uploading some photos. I opened the secret folder on my phone, wondering what pictures I should choose.

There were so many. Different outfits and poses. Short skirts, crop tops, dresses, fishnets, bikinis, booty shorts, and thongs. Me bending over, me on my knees. Standing, sitting, laying, and everything in between. Being so flexible I even had pictures of my feet behind my head or doing a split.

I felt my cock get hard as I scrolled through the photos. My ass is fat, my hips are wide, my waist is skinny and my body is toned. "I look better than most women!" I thought smugly.

Eventually I found 5 photos I liked and uploaded them. There couldn't be any nudity, and there was no way I would show my face, but I found 4 somewhat modest pictures, and one showing off my ass in a thong. Thinking of all the people that would see those pictures turned me on, even if it made me nervous.

Yet over the next few days I didn't have much luck. I only had a handful of matches and only half bothered to respond. Mostly just asking why I didn't show my face. It was disheartening, swiping through girl after girl. Each swipe came with another sense of rejection.

I kept running out of people to swipe through, and had to increase my age and distance preferences more and more. Then on Tuesday night I opened the app and saw her. Her jet black hair and piercing blue eyes once again stared right back at mine through the screen.

I was mesmerized. I was standing on a grass field with the sun shining and birds chirping. Her hair blew softly in the wind as she stood there, looking at me. She seemed to radiate light. The sky was the same shade of blue as her eyes. Her smile seemed so friendly, yet so dangerous at the same time, as if she knew something I did not.

"Jamie, you wanna get food?" Jack's voice brought me back to reality.

"No, I'm not hungry." I yelled back, still staring at my phone.

"Ah no wonder you're in such good shape! Text me if you want anything." I heard the front door close behind him.

I stared at her picture, not wanting to swipe and lose the ability to look at her. Why hadn't she shown up in my feed earlier? Her name was Ashley. She was a year ahead of me.

Her pictures included her at the beach in a bikini, her with her friends at a party, a selfie at the gym, sitting on some stairs in a tight black dress. When I got to the last picture I nearly dropped my phone in shock. She was on the football field, wearing our school's blue and white cheer outfit with a white bow in her hair and Tyrone's arm around her waist.

"She's a cheerleader," I thought to myself. "A picture with a football player means nothing! Besides, he is probably gay since he wanted to fuck me." I read her bio and saw she was listed as a lesbian. "Few!" I thought. I went back to the picture of her in the bikini and took a screenshot.

What happened next would have been the most shocking thing that has happened to me all year, if it weren't for what happened immediately after. I swiped right and we matched! Then, she messaged me first! I couldn't believe my luck, this was too good to be true.

Little did I know, Ashley got notification from me letting her know I took a screenshot.