by Penny Aimes
His eyes widened. “You’re absolutely right. I apologize, this is a particular fantasy of mine and when you were interested, I admit I leapt at it. I shouldn’t have...have I fucked this up already?”
His face looked so dismayed that she wanted to climb into his lap immediately and kiss it better. Damn it, French. “You didn’t fuck anything up,” she said gently. “Have you done this before? I think that might help me feel like it’s less...weird...” Because officially, she didn’t know he was a millionaire.
“Not less special?” he asked.
“I mean maybe a little?” she said. It honestly hadn’t occurred to her, but now she examined it. “I mean, I guess I know you didn’t invent spanking just for me, either. There’s only so many ways to be kinky no matter how hard we work at it.” She grinned, and he brightened in response.
“I did it with my ex. I guess it was different then because we were already living together before we got kinky. In a funny way it was just a kinky gloss on some household budgets. But doing it taught me a lot about what I liked.” Talking about this part of his life seemed to take his expression back into darkness.
“So what do you like?” she asked.
“I like spoiling the people I—I care about,” he said. “We haven’t talked about this, but honestly, it’s not a lot of money to me.”
“But it is to me,” she said neutrally. Some less disciplined parts of her brain were howling about the phrase “people I care about” but she was determined to do this right. This wouldn’t work for either of them if they didn’t do it right.
(I’m people he cares about!!!!)
“That’s—not what I meant,” he said quickly. “Look. I like to dress women up, okay? It’s a huge turn-on. If you did this, ultimately I’d like to have input into what you wear every day, or at least when I have time to plan something. Part of this is so I have a better idea what’s in your wardrobe, and so you have some...”
“Nicer things?” she prompted.
“Things in tune with my aesthetic for you. I’d love to just buy you the clothes, but I know I’ll get things wrong, at least at first. Maybe after a while I’ll know what you like and what I like and we can try that, too.”
“My own personal Stitch Fix,” she mused, trying different ways to think about it. Seeing if there was one that made it fit in her head. God knew she wanted to find a way forward.
He laughed. “I like that. Maybe I’ll use it next time I have to explain it to someone.”
She willed her smile not to dim. “Caroline would love this game. For sure.”
His own smile faded. “So what do you think? Are you in?”
She thought. “I need you to admit something first. It’s at least a little about the money, isn’t it? I mean...you have more money than me.” She’d had time to think about this. “That’s a fact. That’s power you have that I don’t. And this is all about power exchange, taking those imbalances and making them sexy, but...we can’t do that if you don’t admit it. We absolutely have to be ruthless about admitting it.”
He seemed to absorb that. “Okay. You’re right. It’s a little bit about the money.” He sighed, his eyes roaming around the room. “I didn’t grow up with...the kind of money I have today. When I got my first big bonus, I paid off my parents’ house. And I could do that, not because it was so much money, but because my parents’ mortgage in Illinois was that small. But they would’ve been working on paying it off the rest of their lives.
“I like that power. I like not having to think about whether or not I can afford it when I want to do something or solve a problem.” It came out in a flood; not an outburst, but something unlocked from deep within, coming out of his mouth fast and unplanned. “Having options.
“So I like having money, and yeah, I like to show it off a little. Not excessively, and not for its own sake, but because it protects you. It makes things easier. I’ve heard that Black men have trouble getting into some of the fancier bars on the West Side around here—”
She had not heard that, and was shocked, and then mad at herself for being shocked.
“—but I haven’t. Not when I’m dressed up. It’s not...a perfect defense,” he added quickly. Intently.
“But that’s...that’s the fantasy,” he concluded. She could see uncertainty in his eyes, wondering if she really understood, and she hurried to reassure him.
“No, I get it,” she said quickly, searching for her own words now. “I think I do. It’s like... I work...really hard. I work really hard on how I look. Because I feel like if I’ve done everything I can to send the message that I’m a, that I identify as a woman, then even though I don’t pass, I... I did my best.”
She didn’t consider herself totally ignorant on matters of race, but there was a long way between putting a Black Lives Matter sticker in your window and knowing how to be a good partner to someone who faced challenges you couldn’t understand. But there was something here she could understand.
She knew, she knew, she was just as much a woman in sweats and a day’s stubble, but it could be damn hard to find her voice to say so. When she was dressed up it was simultaneously more of an insult and that much easier to say, “it’s ma’am, actually.” Most of the protection was illusory, because nine out of ten times no one said anything anyway, and at the end of the day she knew she didn’t pass to anyone looking closely. But if she did her best, she didn’t feel quite so much like she was waiting for it to happen.
She went on: “It’s probably a little fucked up, but it makes me feel better, and I can face the world as my best self.” It wasn’t what she would expect of any other trans woman. But it was what she needed to go out the door in the morning.
He was nodding “Yes. And the money just makes it easier.” His eyes found hers again and all uncertainty was gone now; she felt like he was pouring some kind of energy into her that spread to the roots of her hair and the tips of her fingers.
“I want to share that with you. Yes, I want to retain some control of how it’s spent. And yes, I want to see you in the kind of things you can’t usually afford. It is about power—and I want you to feel my power head to toe when you walk out the door in the morning. But I never want you to feel trapped by it. I want you to wear it like armor.”
She sat very still, because she felt like if she moved at all she would explode. She felt pinned to the chair by the intensity of his gaze and his desire. Her own desire. She’d never had much of a sugar baby kink, but yes, she could understand this. She swallowed audibly. “O-okay. I’m still interested. I do feel like...it’s so much money. It feels a little wrong. But—it’s practical clothes, too? I mean, this isn’t just a lingerie account, it’s work clothes, jeans, stuff like that?”
“I’m absolutely going to veto any pants,” he said, quite seriously, “but yes, like that.”
“Well... I don’t have space for an entire second wardrobe. I’ll have to get rid of things I already have. I do know some clothing exchanges for trans women that could use them...” She was talking herself into it. “It’s so much, though.”
He laughed. “It’s really not,” he said. “But we can start with a lower number if you want. Work up to something more ambitious as you feel more comfortable.”
“As I feel more comfortable? What about you? It’s your money. What if I took it and ran?”
“I think we’re worth more than five hundred dollars,” he said, and it was like his first confession of desire; simple and stark and a line drawn in the sand, daring her to give a little. “Don’t you?”
She stared into her lap until she made up her mind, and then raised her head. “Yes, Sir.” It was the we that got her. More than anything, she wanted them to be a we. A thousand objections and fears fell at the feet of that we and surrendered.
“Terrific.” He really was beaming. “Can I see your closet?” he asked. “I’m not going to pass jud
gment, and I won’t tell you to get rid of anything. But I’d like to know what I’m working with.”
The inventory of her closet went smoothly until they came to her small collection of lingerie, and then the evening took a delightful turn where money didn’t come up at all. Of course, neither did an orgasm, because someone had had the bright idea to say, “Let’s make it two.”
July
She threw all of her building sexual frustration into organization; she created an online spreadsheet with a catalog of all her clothing, old and new, organized by type. It took a bit of work, but she rationalized it to herself as fair value for the money she was receiving. She laughed aloud in her apartment alone when she saw he’d simply hidden the “pants” tab. A man of uncomplicated tastes. Other items were bolded or color coded as he explored.
Over time the arrangement shifted, with explicit renegotiation. (There was a tab in the document for that, too.) She rapidly learned to recognize the colors he liked, or at least liked on her. Pinks, yellows, deep purples. Pencil skirts and blazers passed without a problem. Occasionally a dress was rejected as too shapeless or long. Tights were resolutely rejected until she started investing in stay-up stockings or garters.
It was fun; it was another opportunity to feel close to him. She had new expensive professional clothes and an excuse to wear them. It did feel like he was with her, all around her, when she walked into a meeting in his choices. She went into her performance review in a black and gold Versace shirtdress and another couple hundred dollars in lingerie underneath it, and when her compensation came up, she asked herself what Dennis Martin would say. She walked out with 5% more than she’d even dared to dream she would get.
Later in the summer, when she started sending him a picture of her outfit every day, the limit went up to a thousand dollars per week, although she rarely touched the maximum. By fall, he would be giving her instructions every other day or so, and the prepaid card would be replaced by one of his credit cards. They fought for a week about that before she agreed.
The card, not the instructions. As she had suspected she would, she found the instructions...fun. They texted and communicated endlessly. His expectations and affirmations; her fears and fantasies. It was pretty much always sexy, being dressed up by him, and sometimes it was extremely hot, wearing lingerie under her work clothes or being pushed, just slightly.
The night before their two-month appointment, before her next opportunity to orgasm, he texted her:
Dennis: You bought some bathing suits recently, right?
April: yes Sir
At that point, she’d only made a few purchases. It was simple enough to use the card and send him the links to her purchases for approval. He’d been sparing with the veto, and she was still trying to detect his taste. Nothing too kinky. So far.
Dennis: I want to see how they look on you. Send me pictures.
She wondered where this was going. She’d bought the bathing suits on a whim, but she rarely felt confident enough to swim in public. She’d gotten three suits; a staid black one-piece with a ruffled skirt, a sunny yellow two-piece tankini with matching shorts rather than briefs, and a green bandeau top she could wear with the same shorts.
She thought about shaving—it was after work and her five o’clock shadow was ticking—but she’d have to remove her makeup first and then either reapply or take photos barefaced. She didn’t want to keep him waiting too long. She took a deep breath, put the worries aside and let herself drop into the submissive headspace. Starting with the most conservative suit and ending with the bandeau top, her self-consciousness was forgotten as she modeled for him. By the end her arousal meant she could barely manage her tuck anymore. She was stroking herself as she sent him the pictures, although she’d already checked off her edge for the day.
Dennis: I can’t believe I didn’t veto that black thing. Can you still return it?
April: i think so Sir
Dennis: We’re meeting tomorrow for your one-month deadline. I want you to wear the bandeau top and cut off shorts.
April: i dont have any cut off shorts!
Dennis: You have scissors, don’t you?
I want to be able to see your tattoo.
Her stomach did a slow lazy roll. She had never once gone out in public in anything that short, let alone as revealing as the top. Her brain immediately thronged both with wordless, giddy glee—it was such a fantasy!—and a thousand unanswered questions. She took a deep breath, tried to resist—tried to hold on to her headspace and just obey—then typed in a rush:
April: where are we going to go dressed like that Sir?
Dennis: You’re going to show me your favorite barbecue spot.
It’s supposed to break 100 degrees tomorrow, I want you to be comfortable.
April: im not sure ill be comfortable like that Sir!!
Dennis: What color?
She bit her lip.
She could veto this. She absolutely could. And this was... This was close to the red. She was still in the top, and she looked in the mirror on her bathroom door. Right now, she felt sexy, liked the look of the simple scrap of green around her slight bust, liked the shorts hugging her hips, but how would she feel when she wasn’t aroused?
April: yellow
Dennis: Thank you for telling me, lovely.
What would make it more comfortable for you?
I had a vision of you as a summer goddess.
Well. Shit. That was sweet. Her heart swelled, and she looked in the mirror again.
Dennis: What if you wore a blouse over it?
April: buttoned or unbuttoned?
Dennis: How about tied off?
April: i could do that Sir
thank you for working with me
Dennis: Of course.
Do you have sandals?
April: yes Sir
Dennis: any with heels?
April: Sir I dont wear heels, I’m already so tall
Dennis: My sister is the same height as me and she wears heels all the time.
April: really?
Dennis: She says she would still be tall if she didn’t wear heels, so fuck ’em.
April:
does this mean you want me to get heels Sir?
Dennis: Just one to grow on, I guess. Your regular sandals are fine.
I don’t need to always be pushing your boundaries, doll.
Thank you for indulging my whims. You’re a good girl.
She shivered and squeaked as she brought herself to the edge of orgasm, then stopped abruptly, squeezing her eyes shut against the sudden flood of regret and longing. The impulse to continue warred with the impulse to be a good girl.
There was nothing stopping her but her word. With Marie, there’d been a padlock in the way, at least. But it was the moments like these that held her... Moments where she felt his intoxicating control, more exquisite than any orgasm. She’d gone a month. What if she went further? How depraved would she feel then? How desperate? She realized she was halfway to another edge and pulled her hand away.
April: thank you Sir
youre wonderful to me
And in the morning, she got up earlier to buy sandals with three-inch cork wedges before she met him at the food truck. The truck was located in the parking lot of a bar, right out on the boiling blacktop, and he was there already when she parked, sitting at a rough wooden picnic table soaking up the July heat like a lizard in a tank top and basketball shorts. It was by far the most casual thing she’d ever seen him in. The lean muscles of his arms and legs were on display, and his dark skin glowed with copper undertones highlighted by the glaring midday light.
He was wearing sunglasses—the blazing sun was nailed to a blue-white sky, they both were—but she could feel his eyes moving over her as she approached, and she tried to put a little extra sway into her hips. Combined w
ith the unfamiliar heels, she stumbled, and he leapt from the table to catch her before she hit the scorching asphalt.
“Oh dear, oh dear. You’re such a good, obedient doll. Come on.” He helped her to the table, her face flaming and her brief spark of confidence doused. “Hey. You’re all right.” He lifted her chin and kissed her thoroughly.
“I’m a clown,” she whispered ruefully, but she was able to say it now like a joke and not a confession.
“You’re learning. I’m so pleased with you for trying something new.” His dark hand stroked her tied-back hair, and for a moment she floated shamelessly between the heat of the sun and the heat growing inside of her.
Gradually, she regained consciousness of herself and her position, and she bit her lip. “Will you...”
“Yes, pet?”
“Will you order for us both? I don’t...” She came here all the time. The thought of looking the owners in the face and asking for a lunch special dressed like this felt...impossible. She’d never be able to come back.
He kissed her hand. “Absolutely. What do you want?”
They settled on splitting a three-meat plate, which came with two sides. She had misgivings about eating barbecue when an orgasm was supposed to be on the menu—post-barbecue sex didn’t sound like a great idea—but damn it, her honor was on the line. He had to see. “Get the chicken,” she said. “Most barbecue chicken in Texas isn’t worth a damn, but theirs is fantastic.”
“Yes, ma’am,” he chuckled, and stroked her hair one more time. It was too good. It didn’t feel like a scene, or even like a date, exactly. It felt like a dream. It felt like a normal Saturday morning with a (don’t say it) boyfriend.
Dennis seemed as cheerful and relaxed as she’d ever seen him, trading daps with Roger and laughing as he loped back to the picnic table on his long legs. If she kept looking at him, she was going to keep falling for him. She studied her nails instead—they were new, French tips with metallic gold edges instead of white—and tried to remind herself of her place. That this was a scene, with a beginning and end, and when it was over, he would just be her very good friend Dennis.