Letter from Montgomery

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He finds to be more of a man you have to be less of one!
1.2k words
2.6
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Part 1 of the 2 part series

Updated 06/09/2023
Created 08/17/2019
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Dear Shoeblossom,

I didn't think there were any transgender men in Alabama, but apparently my husband and I got one as a client! This little convo was funny and somewhat arousing to friends of mine, so thus, I submit it.

Syndi

"Oh, thank you for letting me out, Syndi."

"How was it, Won Joo? Let me sponge off those perky tits of yours."

"Oh, that feels so good. I know I asked for more closet time, but it's so hot in there. Still, I had to rest up after the caning."

"You Koreans are tough. I've never had a sub that could take on such absurd amounts of discipline. And you're such a tiny little thing, too."

"Is-it there any way I could-service you, as a reward for being so uh, conscientious?"

"Honey, I really don't swing that way. When Pollux and I moved in with you, I thought we made that one clear."

"I-I know. Sometimes I've-convinced my Dominant to become more bi-curious."

"Well, you're a gorgeous young woman. A bit out of place here in Alabama. I grew up in a little shit-box in Milledgeville, Georgia, and it was not a party for a little black girl, but I can't imagine being an Asian here, at all."

"Will I be going into the stocks after dinner, Syndi?"

"Pollux, he's of the mind that it will take your mind off your career if you spend more time in forced contemplation. Besides, unlike me, my husband IS attracted to you, and loves to cane your cute little butt while you're locked in those holes."

"I-I got those tickets to the opera you wanted."

"Just two, right?"

"Yes. I understand why I can't go."

"Jesus, you are toying with your clit as you talk to me about it. "

"My clit...sorta."

"This is why we do one week on domination, one week off, so you can re-assemble some sense of your regular life, and not lose your friends, and so we can all do things together, Frisbee, basketball games...concerts."

"I know. I just don't...I want to serve you fully. It's not about me."

"Won Joo, you are serving us. At a rate of a thousand dollars a week."

"But I'm paying YOU."

"Yes, it's working out well."

"And you know, Syndi, I'm not really a woman, per se."

"But aren't you, Won Joo?"

"But...I still have my testicles."

"Won Joo, you can't eat your cake and have it too. The fact is, even if you were a full-blown, fire-breathing heterosexual male, you're four foot eleven and very slender, even with your new breasts."

"I-I know."

"Here's a good question. Why are you still a cashier at the Shopquik with all your money?"

"I got that money from an inheritance, and I'm spending it all on being trained by you and Pollux. I'll still need a job, right?"

"You wouldn't like to go back to school?"

"I'm a rare Asian in that I'm of about average intelligence, maybe bright normal. I'm forty years old and have had the same job since I was seventeen. They are really nice to let me stay on now that I'm a girl."

"Yes, but you might have some curiosity-"

"Syndi, the only curiosity I've ever had is what it would be like to be a submissive girl. And my dad's eighty thousand dollar life insurance will take care of the rest of the operation and six months of your company, which is amazing."

"That's so fascinating. And terribly flattering. Let me touch your little cock-clitty a little bit."

"Oooh, that' feels so good."

"This is why we have the little gadget on the end, Won Joo, so you can touch it but you can't have a nasty little mess. It's going to be so much more interesting for you when we remove it all."

" I know, it feels, oh when you rub the underside with your nails, ohhh."

"Pollux had one sub who just got off on having Pol watch as his balls were surgically removed. It was a little odd, but he was terribly devoted to us."

"Please-take off the guiche, Syndi. I am feeling cramped."

"Yes, of course you are! You're all excited and it's bulging in that tiny little space."

"God, it's starting to hurt a little. But it's exciting, too...I love your cleavage in that little leather top, Syndi."

"Hands behind your back now, girl. I don't want you having to lose control and grope me, and then me having to call Daddy to give you a whuppin."

"No, I understand."

"I could just whip your penis myself, and that would calm you down a bit, Won Joo."

"No, oh that would...if you really think it's necessary."

"I can feel how much stiffer your rod is when I stroke it. I might give you a little treat later, though."

"Really? Oooh, you rub it so lightly with your fingers-"

"Von Slyke, an old client is coming into town, and I hold his chastity keys. He might blow you, and that would be a thrill that you won't be getting much longer, Won Joo."

"Mr. Von Slyke owns a lot of the Shopquiks in Alabama. I wonder..."

"Yes, you'll have to put in for a raise as you cum all over his grotesque beard."

"That-wow he might make me manager of the Shopquik."

"Stranger things have happened. I want to start a new training with you, Won Joo."

"What's that?"

"Well, your operation isn't until next spring, and I want to be able to give you a nice hand job, and then snap my fingers, and make you go limp-instantly."

"That's not going to be easy."

"Well, if I cane you with a thorn branch from your rose bush, it might calm you down."

"Those bushes are so thick with sharp thorns that I have to wear gloves when I cut them down."

"That's right, but if I have to whip your dick down, say, four or five times, it might-"

"That's...it's arousing thinking about it, but I don't know-"

"The trouble is, you're too much like Timrod. Timrod is an old client of mine, an ex-jock who was always getting in trouble for sexual harassment. He was really proud of his big dick."

"Yeah, if I had a big one I would be, too..."

"I was able to put Tim in a Kali's Teeth Bracelet, which has very, very sharp needles in it, and then I let him watch porn, or check out the gals on the soap operas, whatever he wanted, and as his dick inflated, it deflated quite a bit."

"That must've been an experience."

"To say the least, Won Joo. Then I had Timrod kneel naked in front of his assembled secretaries, file clerks, typists, staff assistants, bookkeepers..."

"Really, the big boss?"

"Yup. And they took turns alternately jerking him and then whipping his cock until finally he became quite meek, our Timmie, and now, if I snap my fingers, he can go limp in seconds."

"I'm not that bad to women."

"Oh, no, but you still have that whole attitude. You want to strut around. Mrs. Ohrenstedt, your assistant manager caught you looking at the dirty magazines, and snorting, and she says she took you over her knee and whipped you with a spatula."

"She pulled my pants-"

"Of course she did. Grabbed the spatula from Kitchenwares and what good did it do you?"

"Yes. I probably-"

"I want you to go down on Mrs. Ohrenstedt in the employee's rest room every night for a week."

"She is disgusting! She weighs-OOOOOw!"

"We don't want a lot of back-talk, Won Joo."

N-no Syndi, of course not."

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