Chapter Text
I just couldn't take it anymore—the insults, the threats, all of that bullshit, but I also knew I didn't have the strength to detransition on my own. When I found an online forum dedicated to men whose kink was feminizing and detransitioning trans men, I knew I'd found just what I needed…
It was Monday morning when I met him in person. It was raining outside the diner window where we sat, cars rushing by in the twilight and kicking up spray in their wake. He introduced himself as Bob, and I could tell he was somewhere in his fifties. Bob wore a designer suit and a blue silk tie, and had a bearing that told me he made good money with his silver tongue. Physically, he had intense blue eyes and a full head of silver hair, and stood well over six feet tall. He had to be married. No way a fox like this stayed on the shelf. Still, I wasn't here for his upstanding moral character. Bob had agreed to my terms, but I wasn't stupid enough to think he hadn't lied. I was willing to bet Bob wasn't even his real name.
"Is this really what you want?" Bob asked, a twinkle of regret in his eyes. I hadn't expected him to care—this was a guy planning to be my detransition sugar daddy, after all. He would pay to feminize me and get off on it in the process. I'd already told him there were no limits. I'd already been disowned by my family, so I had nobody and nothing left to lose. I'd also quit my job due to rampant transphobic abuse, so it wasn't like anyone would notice or comment on my changes.
I rubbed my stubble nervously. I was going to miss it. I didn't really want to go through with all this, but at the same time, I was aroused at the thought of being molded into Bob's fantasy woman. The thought of giving up control and letting someone else shape me into what they wanted sent delightful shivers down my spine. I'd fucked everything up, and it was a relief to be rid of the burden of driving my own life. I could stop worrying about every little thing. I could abandon my laughable attempts at transition and passing. I'd even been denied the right to choose my own name when I was shot down by a judge because of an unpaid fine for possession of marijuana. My legal name emblazoned on everything had completely sunk any efforts I'd made to go stealth.
That was all over now. Once Bob was done with me, I'd want to use my legal name. It would match my body, and I wouldn't have to be ashamed of it anymore.
"It's what I need," I said. The abuse had almost driven me to suicide, but I wasn't convinced body dysphoria wouldn't do the same. That was why I needed Bob. He was going to watch over me and keep me safe while I detransitioned. He would stop me from hurting myself, while making sure I didn't give up on my goal of becoming an attractive woman.
Bob licked his lips. "Let's get out of here." He dropped a hundred-dollar bill on the table, not even asking for the check. I climbed into his Mercedes, wondering if I asked him to drop me off somewhere if he'd do it.
I needed to stop thinking like that. I'd asked Bob to help me. Wasting his time and leading him on was cruel. Sure, this wasn't an act of charity on his part, but he deserved to get what he was paying for.
Bob was quiet in the car as we sat in traffic at a red light. I leaned my forehead against the window.
"Why're you into this, anyway?" I asked. "You anti-trans?"
"Not at all," he said. "I don't have any intention of harming you. I think you know that, or you wouldn't have agreed to meet."
"So what's in it for you?" I think it was more curiosity than anything that prompted me to ask. I wondered if Bob would be honest, or whether he'd spin me a line to make himself sound better.
"I've got a kink. Well, a few, actually." He closed his eyes and breathed out, opening them only when the light turned green and he had to focus on driving. "Can I be honest with you? I think maybe I'm a trans woman. Sometimes, when I'm alone, I dress—"
"Ok," I said. I didn't need the whole spiel about how he dressed in stockings on weekends and jerked off to completion. Though it made for a tantalizing picture in my head, I felt sketchy about it. "So feminizing me—it's about your desire to feminize yourself. That's your motivation."
"You asked. Do you want out of the deal? Have I misrepresented myself?" I noticed a flash of sadness as his eyes met mine briefly, then he looked away and focused on the road ahead.
I shrugged. "No. If you feel that way, why don't you transition?"
"Same reason you want to detransition. I know I wouldn't survive the ordeal. I work for a top law firm. Do you think I'd keep my job if I showed up in a skirt and heels?" Bob's thick fingers clenched the steering wheel. "Look at my body. It's the masculine ideal. Square jawline, huge hands, deep voice. It's impossible for me to transition. I'd never pass. I'd be a walking joke."
I could have argued about surgeries and hormones, laser hair removal, and pretty wigs, but I recognized it for the hypocrisy it was and bit my tongue. If I couldn't make it through transition, what chance did Bob have? I had a lot less to lose than he did, and I'd still failed.
"I'm sorry." What else could I say?
Bob laughed, a deep, booming chuckle that made me wonder if he was just messing with me. "Don't be. I'm a sexual guy, anyway. Hormones would make my dick limp. I think I'd rather keep crossdressing in the realm of kinks."
I nodded.
Bob pulled onto a large driveway in a decent neighborhood and killed the engine. The houses here had to be worth half a million or more, with white picket fences and a homeowners' association. I had to wonder if this was his home, or a place he'd rented to keep his real life separate from the dirty little affair he was having with me. He'd probably told his wife he was working at the London office or something while he spent months in a strange new town halfway across the U.S. with me.
"Last chance to back out. I'm not gonna hold back. I've got big plans for you, starting with that flat chest. I like big tits. Really big tits. I'm gonna pay for implants until you're stuffed so huge you look ridiculous." His voice became thick with arousal, and I could see the tent in his slacks. He adjusted himself, rubbing his cock through his clothing. "Gonna grow out your pretty hair until it's halfway down your back, and put lipstick on those lovely full lips. Train your voice to be sultry and sweet, and once you're ready I'm gonna pump you full of my cum until you're pregnant, and your tits get even bigger and heavier with milk—" He gasped, and I realized he was cumming in his slacks, an obscene stain spreading across the front of them. Fuck, he'd barely touched himself and he was this excited, his head banging back against the headrest as he rode out the wave of his orgasm.
I swallowed, my mouth dry. I could run, but my little dick was excited. In some perverse way, I wanted this. I wanted Bob—who sorta, kinda looked like my Dad now that I thought about it—to turn me into something unrecognizable from who I was now. Someone who got positive attention from men, not negativity and insults. I wanted him to put a baby in me and change my brain chemicals until I didn't want to be a man anymore—just Bob's woman.
"Let's do it," I said.