Just This Once Ch. 02

Being in my senior year, the thought of summer should be my own personal wet dream. Freedom from school, from my family, from my social torment. And maybe 4 months ago it would've been. But I've never been so directionless in my life. And now that I stand on the precipice of escaping and enjoying my adulthood, I'm more miserable than I've ever been.

The crossdressing is all but out of control at this point. At first it was once or twice a week. Now it's any chance I get. Any alone time I get, I spend dressed, no, lived as a girl. I spend all my time at school ogling the boys (especially my "secret boyfriend" Jake). I spend every waking minute jealous of these beautiful girls. I want Jake to look at me the way he looks at his real girlfriend. It's maddening.

I at least managed to wean off using my mother's clothes. They aren't stylish for an 18 year old girly-boy like me anyway. I spent all of my money on summer clothes, bras, panties, lingerie and makeup. And I've learned so much in 4 months too. There's not a single hair on my body. I don't even touch my tiny cock anymore. I've been practicing with cucumbers (they're about the size and thickness of Jake's magnificent cock). But I can't work up the nerve to approach Jake (or any boy for that matter) and ask for them to take my virginity. And I'm afraid I won't before it's too late. Prom was tonight.

I stared in the mirror. Full makeup, outfit, long hair...everything. I didn't even recognize this person. With my face and body, if I stuffed my bra, I'd be at least an 8. Go fucking figure. I'm an ugly boy, but I'm a beautiful girl.

I crept down the stairs. I had already told my mom I wasn't going to prom. "Big surprise, loser," she said. Her words used to hurt, but not anymore. She was watching another movie on the TV, eating herself to sleep. I slipped out the door in full drag for the first time ever. No, not drag. To anyone else, I was just a normal 18-year-old girl. My heart began to race.

I knew I had no chance of going to the dance with Jake. I was after sex. I had waited long enough. 4 months of blowjobs. 4 months of being ignored. I did everything. I made myself into a girl for him. I learned to look like a girl, walk like a girl, talk like a girl, even fuck like a girl. I studied girls' habits, even the female voice, until they were second nature. I removed any semblance of a boy from my appearance. I watched porn, learning how to turn guys on, how to ride cock like a pro. I didn't care that my life fell apart. I didn't care that I didn't have any future planned. I needed this to help make sense of things again. I needed cock to make me feel whole again.

I made it to the school parking lot. Prom would be ending soon, and many inebriated teens were leaving the school and stumbling to their cars. As I was now clearly visible, I took a deep breath. "Moment of truth," I said to myself, knowing that if I was caught, my social life was completely over. Girls in dresses gave me stern looks, almost judgmental. I WAS wearing simple clothes: a girl's hoodie over a white t-shirt, and some jean shorts. But I still couldn't gauge whether I was pulling it off from their looks alone. I wasn't sure until the boys began to flash wolfish grins at me, some whistling and some asking me if I'd like to "hang out". While I turned down each one, my body grew hot and my cock threatened to stiffen from the attention. I couldn't help but smile.

After a quick search, I found Jake's cherry red Mustang (the same one I'd sucked him off in a few times). I leaned against the driver door. After about 5 minutes, I saw him. He was handsome as hell in a tuxedo. His bowtie was loose around his neck, and by now he had let a 5 O'Clock shadow grow on his face. He seemed to be alone...and distracted.

He arrived at his car, head down, before stopping suddenly, looking into my eyes with concern. "I'm sorry I didn't see you ma'am," he said almost flirtatiously. Or maybe that's just the way he sounds normally. "Where's your date," I said, trying to completely disguise my voice. He didn't give me any funny looks. "Oh, um, it didn't work out," he said, somberly. "I'm so sorry," I said trying to mask my excitement.

He studied me for a moment. "Please don't take this the wrong way...you're very beautiful. But, do I know you?" he asked.

I trembled at his compliment. "You do, actually. We met over there," I replied, pointing to the dark bleachers at the soccer field. He looked puzzled for a moment. "M-Matt?"

"Call me Megan when I'm dressed like this," I replied, smiling at him. He smiled back.

"I didn't recognize you...you're fucking gorgeous!" he said.

His eyes began to sparkle, as he began to work out he might be getting a blowjob tonight after all. Little did he know, I planned so much more.

"Does this mean you want to...?" He began to ask, making a stroking gesture with his hand.

I placed my hand on his face. "No, Jake."

He looked disappointed for a moment.

"I think what we have is more than just that. I'm in love with you and I want to be more than just your dirty secret. I want to be your girlfriend. I want you to deflower me and turn me into a girl Jake. It was you who made me realized what I was missing. I want to be your bitch to breed whenever you want," I confessed passionately. "I did all of this for you."

Jake looked taken aback. His face was beet red. He didn't speak for almost a minute.

"Matt...you're hotter than most girls at this school. But I'm not a faggot like you. I can't be seen walking around town with a boy dressed like a girl. I'm a Caldwell. I have a future."

My heart sank.

"I think its best if we just...don't talk anymore. I'm sorry I didn't mean to lead you on, I thought I was doing you a favor by giving you my cock...you know, letting you sort some shit out. I didn't mean to turn you into a girl. I think you should really get ahold of yourself. I mean, dude, you're dressed like a fucking slut in the middle of the school parking lot asking some guy you barely know to fuck you. That's some dirty whore shit right there. I mean, its no wonder Kaitlyn left you, she could sense how gay you were." The longer he talked, I could feel my will to live slip away. I couldn't even have this.

"Fuck dude...graduation's in a week. You've got to give a speech, man. What the fuck are you doing? This has gone too far. You want my advice? Straight girls don't want to fuck other girls. Lose the makeup, the panties, all of it if you want a girlfriend."

I was hearing but I wasn't listening. It took everything to keep the tears in. Jake stared at me for a while before getting in his car and driving away, without saying another word, leaving me standing in an almost empty parking lot at one in the morning, dressed like a slutty girl. I collapsed to my knees.

Before I knew it, I was on the other side of town (the dangerous side), walking under an overpass. I must've gone on autopilot, I told myself, and walked to clear my head. I took a deep breath, composing myself. Then I heard it.

"What's a pretty little thing like you doing in a place like this?" a gruff voice asked from the darkness. I could just make out a tall, slim figure...about 6'3".

"I was just leaving," I replied swiftly, almost forgetting to use my girl voice.

"I disagree," the voice said.

He stepped into the light. He was a tall, pale man. He was definitely rough, but not ugly. In fact, the more I looked at him, the more handsome he seemed. Maybe late 20's, early 30's? He had an unkempt stubble and shaggy but clean hair. He was dressed exactly like a 1950's biker: leather jacket, blue jeans, white t-shirt. Without warning, he came up from behind, wrapping his arms around me and pulling me into him, all the while grinding his pelvis into my butt.

"Damn baby...you're so damn fine, there's no way I'm tossing you back." His voice was smooth like molasses.

His thick, rough fingers began teasing the waistline of my panties out of my shorts and up to my hips. I should've been terrified if I wasn't so damn horny. I was into it, and as my mind began to melt away, my last thought before giving in was "Fuck Jake...fuck them all."

Before I knew it, I was back at his house. We were making out, my dark red lipstick smearing on his rough kissable lips. "This is my first kiss," I though to myself. I could smell alcohol on his breath, but it only turned me on more. He wasted no time, like Jake. He had his jacket and shirt off, and revealed a rugged set of washboard abs. His chest had some hair on it and a few scars, too. His back was covered in scars as well as tattoos. Similarly, his arms had entire sleeves of tattoos. As this went on, this guy was rapidly becoming hotter than Jake ever was. He was definitely more exciting.

He began to unbuckle his belt before pausing to remove my shirt. I returned to my senses for a moment as a thought crept into my head. "Does he know I'm a boy?" He stared at my flat chest through my underwire bra. He thought for a moment.

"You're a trap aren't you?" he asked.

Shit. I'm caught. I nodded my head glumly.

"You already got a master?" he asked.

My ears perked up. "A master?" I asked.

"You know, a master, someone to turn you into a girl properly. Make sure you're following your sissy regime and whatnot." He explained.

"I-I don't have anyone like that. I'm only 18. I'm still a virgin."

He stared for a moment. "I can be your master...if you want."

As I stared at him, I thought back at all the shitty things that had transpired these last few months. This man was like my guardian angel. He was...perfect.

"Yes...I want you to be my master, sir."

His mouth twisted into a wicked grin.

"Ok...Megan, was it?...I'm your master now. I have 3, and only 3, rules for you to follow."

"Yes sir, I'll do anything you ask!" I wasn't concealing my eagerness in any way.

"Rule number 1...you're my girl. You live here, you sleep in my bed, you fuck only me... understand?"

"Yes sir!" I nodded vigorously.

"Rule number 2...you will wear this..." he retrieved a small object from his coffee table.

"It's a chastity cage. You only cum like a girl from now on."

I studied the small pink cage for a moment before placing it over my cock and balls, locking it up and handing my new master the key.

"Rule number 3...I will work...you will stay here. You will clean my house, cook my food, make yourself look pretty, and offer your pussy to me whenever I want it...are we clear?"

I pondered for a moment. I was more than ready to leave my old life behind. I was more than ready to leave Jake, mom, dad, Kaitlyn (my ex) in the past. I nodded.

Without another word, my new master, Max, placed me on the bed. He ripped my shorts off and pulled my thong string aside, inspecting me. "That's a pretty pink pussy, Megan. You want daddy to breed it?" he asked in a low dominant tone.

My head was washed over with a wave of pink. I was only here, in this moment.

"Yes daddy, get me pregnant."

Max smiled, before pulling out a monster hairy cock from his pants. His was at least 10" (2" longer than Jakes) and thick as hell. His cock was uncut and hairy, like a wild man, and his heavy balls swung beneath it like two bowling balls. His cock was much veinier than Jake's too...like he had a whole other heart beating in his cock. For a moment, I felt like a female cow right before being bred by a bull. My cock tightened in the cage. Max bent over, letting a glob of spit down over my ass, before pushing the spit inside with two fingers.

"Damn baby your ass is smooth," he cooed.

He lowered himself between my legs, lining the thick, hot tip of his cock with my ass. He pressed my knees all the way back to my shoulders, giving him unrestricted access.

"I want to look you in the eyes when I take you, bitch."

As he said that, my clit began to leak. He stared me straight in the eye before shoving his entire length in, forcefully smacking his balls into me as he bottomed out. I moaned in ecstasy as he stuffed me. He placed the bridge of his nose against mine before passionately kissing me as his hips began to jerk. "I'm being fucked like a girl," I thought.

He began to grunt, piston fucking me faster and faster, all the while staring me directly in the eyes. I have never been more attracted to anyone in my life. It was as if I was a female in 10,000 BCE being taken by this powerful caveman. Every once in awhile, he'd say something like "Yeah, take it bitch!" which only turned me on more.

His thrusts began to slow but were twice as hard. He grunted "Oh bitch I'm gonna cum. I'm gonna knock you up." As he spoke, my own clit exploded without ever having been touched: my first orgasm as a girl. He shoved his cock deep inside me, his hot cum painting my insides white, his sperm coating my womb looking for eggs to fertilize. I was just his female bitch.

After about 15 minutes of post-sex panting, kissing, and him thrusting his cum deeper inside of me, he finally pulled out. As I began to get up, he pushed me back down, shoving a small round object into my ass...a buttplug. "The cum stays inside. Better chance of you getting pregnant that way."

I nodded, pulling my panties back up. He collapsed on the bed, sweating and panting. He pulled me into his chest, making me the "little spoon" as he fell asleep naked behind me. I pressed my ass back into him, submitting fully as his woman, and settled into my new life.