Derrick really took advantage of having me captive that first weekend. He spent the entire time making me watch porn videos, and then had me recreate the scenes with him. He said, that he needed his girlfriend to be fully versed in all the ways he liked to be pleased. His appetite for sex was unreal. The only time we ever really took a break was to eat. And I have to admit, he made the most amazing strawberry milkshakes to go with the food. It was almost worth the humiliation of being fucked sideways by my best friend’s b*****r just to get those shakes.
By Sunday night we were both exhausted and sore. Derrick said he’d let me go back to being Andy for the week but he had some conditions. Number one was that he wouldn’t let Michelle unglue my junk. Derrick said if I even attempted to unglue my pussy, he’d send the video viral. He laid out the terms of our relationship as follows: Everyday after school I was to come over and have Michelle teach me to do my hair and make up, and that I should be corseted, dressed and waiting in his room ready to serve by the time he got home from work. Any deviation from the plan, and the video would go live. He asked me if I understood. I nodded. He gave me a smack on the ass and sent me to Michelle’s room.
I knocked on her door.
“It’s open,” She yelled from inside.
I opened the door, and stumbled in exhausted. Michelle was still in girl mode – wearing the same sexy school girl outfit she wore the first time I saw her. She was watching a copy of the video Derrick made of me and rubbing her now unglued wang through her panties. She looked up at me.
“Rough night?” Michelle asked.
“I’m exhausted,” I sighed as I plopped down on the bed next to her.
“So, Derrick finally cut you loose?”
“In a manner of speaking.”
I filled her in on Derrick’s conditions. She laughed diabolically.
“Well, you wanted to know what it felt like to be pretty, right?”
“Careful what you wish for,” I sighed.
I got up, and looked around for my boy clothes. I couldn’t find them.
“Where are my clothes?”
“I hid them.”
“Oh, c’mon, dude. Enough with the games,” I complained.
Michelle stood up, came to me, and ran her fingers through my hair, and pouted.
“But I like playing games with you. Video games, sex games, All kinds of games. See, I’ve had your mouth on my cock, and your cock in mine…”
She rubbed my crotch.
“…But since you won’t be putting this in my ass anytime soon. You’re not going back to being Andy till I get this.”
She squeezed my ass, and ground her crotch into me. I could feel how hard she was.
“Michelle, please. I’m sore, and tired, and I need to get home.”
“So, go home, then. I’m sure your parents would love to see you like this.”
I stood there and tried to think of a response. Michelle reached up my skirt and stroked my pussy and kissed my neck. I was so fucked. Just her being this close to me made me tingle, and her stroking me was getting me rock hard. I couldn’t resist her. I kissed her full on the mouth.
“I want you,” I whispered.
She quickly shut the door and locked it. She pushed me onto the bed, and climbed on top of me. We made out passionately. And then a terrifying thought struck me.
“What if Derrick hears?” I asked nervously.
“Way ahead of you, babe,” Michelle grinned.
She reached under her pillow and pulled out some restraints and a pink ball gag. She quickly gagged me with the ball gag, and cuffed my wrists to the head board. She lifted my legs, and cuffed my ankles spread eagle to my wrists, forcing my ass into the air. She pulled her cock out of her panties, grabbed some lube from her nightstand drawer, and lubed her dick up. Not that I really needed it after Derrick spent the weekend stretching me out. She stroked her cock to maximum hardness.
“You may be Derrick’s ‘girlfriend’, but I made you. And I made you, so that I could fuck your sexy little ass, and cum on your pretty face… and you went and fucked it all up, bitch! So now you are going to make it up to me, understand?” She growled as she slapped my ass.
I groaned through the gag, and nodded. Michelle entered me, and pressed her cock deep into me, and held it there as she got in my face, and whispered menacingly.
“Good. Cuz I have a few conditions of my own. You better get used to the feeling of having a cock deep in your ass like this you little cunt, cuz your days of being a boy are over. You are just too damn sexy, bitch. And let’s face it, those newly arched eyebrows will make everyone suspect that something is up with you anyway, so we’re not going to hide it. Every morning before school, you will leave your parents house 90 minutes early and come here. I will do your hair and make-up, and make you all sexy, and pick out your clothes for the day. Then, I, myself, as Michael will walk you to school, like a gentlemen.”
I screamed through the gag, and shook my head.
“You’ll do it, or I’ll upload the video myself. And remember I have the before and after pictures – should anyone doubt that the hottie in the video is you. But don’t worry, darlin’, I have a plan that will make your transition practically seamless. You just have to trust me.”
Trusting her got me into this in the first place. But I couldn’t let anyone else see that video. I would be unable to show my face anywhere. I was terrified of what she had planned, but I had little choice. She slowly began grinding her cock into my ass. I tried to free myself from the restraints, and talk some sense into her. Michelle slapped my face hard.
“Don’t fight it. You know you like it. I heard you with Derrick remember. You LOVE getting fucked, dontcha slut?”
I moaned and pleaded through the gag. Michelle fed off my pain and fear. She fucked me with venom and anger, it was more like revenge for fucking Derrick, or an act of ownership. I started to cry a little, but the sensation of her fucking me brought me to climax, and when I came and nearly passed out. She pulled out and came on my face.
“Take that, you fucking slut,” she spat.
She slapped my ass hard, and then rubbed it lovingly. She gently caressed my “pussy”.
“It’s too bad I have to leave your pretty cock glued down like that. I’m so excited about the new you, I’m almost willing to let you tie me up and fuck me.”
I groaned through the gag, and rolled my eyes. Which made her laugh.
Michelle unbuckled me from the restraints, and removed the gag. She walked me into the bathroom, and pulled my clothes out from under the sink along with the new bottle of glue remover. She helped me out of my clothes, removed the silicon inserts from my chest, and for some reason I suddenly felt very naked without them. She helped me remove all the make-up, and then left so I could shower.
While I cleaned up I couldn’t get the look of Michelle leering over me, telling me of my fate. How was it I had know Michael all this time, and had never seen this side of him. Not just he’s alter ego, Michelle, but his truly twisted mind.
After my shower, I dried my hair, and changed back into my boy clothes. I glanced at myself in the mirror. I still looked kinda pretty. I scrunched up my nose and frowned. Something wasn’t right, something just–
“Feels wrong doesn’t it?” Michelle asked as she gazed at me from the hall.
“Yeah. I can’t quite put my finger on it… but yeah,” I admitted.
“I get it. I always feel ‘off’ when dressed as a boy. I love that I can totally be myself around you, now. This weekend has been awesome because I could spend it as Michelle. Thank you for that.”
She kissed me gently and continued.
“See? you might hate me for doing all of this now, but I’m doing you a favor. You’ll thank me one day.”
She had a point, but her plans for school terrified me.
“Do I really have to go to school dressed as a girl? Can’t you give me some time to think it over?”
“Andy, You’ve had your whole life to think it over, and you’ve spent every moment for as long as you could remember longing to be a girl, have you not?” Michelle asked.
“Yeah,” I admitted begrudgingly.
“You have tonight to think it over, but if you aren’t here at 6:30am tomorrow. I upload the video. And then it won’t matter…. so, don’t be late.”
I scowled at her, and she tickled me. I slapped her hand away.
“I hate you.”
“I hate you, more. You actually got some cock this weekend, you slut. I was stuck using a dildo to get off. Now get out of here before I use that dildo on you’re pretty ass.”
I half-smiled back. She slapped me lightly on the ass and pushed me toward the door.
I left Michelle’s, and walked the 2 miles back to my house. Not wearing heels was definitely more comfortable, but it felt weird after 3 straight days of pointing my toes. The night air cleared my head a bit, but I was definitely reeling. I needed to find a way to erase that video before school tomorrow, but in the meantime I needed to make up something to tell my parents to explain why I was leaving the house so early every morning, and hoped they wouldn’t notice my nice new arched eyebrows.
It was late when I walked in. The place was quiet. My parents were probably already upstairs in bed. Their bedroom door was open. I walked nonchalantly past their bedroom on the way to mine.
“I’m home. Going to bed,” I said off-hand.
“Honey,” My mother called, “You’re home late. Anything going on?”
I brushed my long bangs down in front of my face half covering my eyebrows as a backtracked to their room, and stepped into the doorway. My dad was at his computer with headphones on watching football highlights and managing his fantasy team. He glanced over at me for a second, and went back to it. I leaned in the doorway and sighed.
“Mike and I are working on this project for school. Havin’ a hard time wrapping our brains around it. I’m wiped out. Sorry I didn’t call.”
She raised an eyebrow in concern. I hoped it wasn’t because of my eyebrows. She shrugged it off.
“Okay, well get some sl**p. There’s some leftovers in the fridge if you are hungry.”
“Thanks. Oh, also we’re gonna start meeting up early before school to work on this, so I’ll probably be gone by 6.”
“Whatever,” she said.
She didn’t even flinch. I could never get a read on either one of them. Sometimes they seemed to not even give a shit beyond seeming to care just enough to not have people think they were bad parents, but not enough to actually be good parents. I began to suspect that they weren’t sl**ping together anymore. I hadn’t seen them be affectionate towards each other in years. Hopefully they’d be just disinterested enough in me not to notice what was going on.
I sauntered off to my room. I closed my door and locked it. I stripped naked and looked at my hairless body in the mirror, and lightly touched my flat nethers. I was getting used to the idea of being a girl which sent a chill through my spine. I had wanted to be a girl for so long -sometimes, painfully so. I had lived a double life secretly in my mind, so living one outwardly shouldn’t be terribly hard. Maybe someday I would be okay with it. But not now. The more I thought about it, getting to the video and destroying it seemed unlikely. I had to think of something Derrick and Michelle would want more than Andi, but nothing was coming to me.
I pulled on a pair of boxers, and sat on my bed to think. I didn’t have any money. I had no connections to anything of worth, and… I… I…. I was so completely fucked.
What had I gotten myself into? Between Derrick’s mad lust, and Michelle’s twisted sadism I was certain my life was going to get extremely complicated, but I had no idea how right I was.