Dale’s Sugar Daddy Issues

Dale has never been in the greatest shape by any measure. Way back about a year ago the first time I danced with him, he clarified that he wasn’t some kind of baller even though he was blowing money on Kylie like he had enough to burn. Over our many months together, he’s divulged every detail of his life to me and the army of strippers satiating his needs in Kylie’s absence. Dale doesn’t sleep much due to shoulder pain. He doesn’t seem to interact with many people aside from his mother and strippers. He spends his days shopping for Kylie and playing the lottery hoping to one day win big, but collecting small winnings in between. When I texted him Tuesday, he’d been out all day Christmas shopping. He promised he would come by after he went home to shower. I waited patiently for him to arrive, passing the time scrolling through my phone. Dale arrived a few hours later freshly showered with his hair feathered out like an 80’s teeny bopper icon, but more chicken-like. I walked over to where he was grabbing a drink at the register, and took a closer gander at his new do.

Him: Do you like my hair like this?

Me: It’s very… feathery.

Him: It’s kinda 80’s isn’t it? I guess that’s not a bad thing. I just blow dried it.

Me: It looks very soft. It’s not a bad look.

Him: Sorry I took so long. I was out all day doing Christmas shopping on Rodeo Drive.

He said Rodeo Drive as if the words were made of gold. Dale wanted to bask in his fanciness, but I could tell he was a bit ruffled. He was jittery and wild eyed as if he’d been doing blow, but I knew he was sober. I inspected him as we stood side by side in front of the register. The bartender mosied over to us, reluctant to step away from her phone.

Bartender: What can I get for you guys? An hour?

I looked at Dale unsure. I’d walked up to him at the register simply to greet him and make sure he wouldn’t run off with another dancer before I could get my piece of the pie. We hadn’t even performed the typical niceties. Dale hadn’t had a chance to sit down; I hadn’t gotten the chance to sit on his lap while he makes some remark like “I missed those” as he looks down at my breasts; I hadn’t listened to any of his Kylie musings. Was I ready? I guess, as ready as I was going to be that night. My breasts ached and my nipples were pointy and irritated. I could smell every passing strip club odor and I already had a headache.

Him: Yeah, let’s do it.

Dale pulled out his envelope and produced $600. The bartender turned away to mark down the transaction.

Him: She has a really nice booty. Nice and strong. She should be a dancer. I wish she’d let me touch her booty.

It was like word vomit, and yet in this context, while it was unpleasant, it was not entirely inappropriate. The bartender was dressed in her characteristic black bikini. She was as much part of the ambiance of the club as I was. I felt ashamed Dale was acting out of pocket, but he pulled out a $20 and tipped her.

Dale: Thank you, beautiful!

The bartender handed me my receipt and I escorted Dale upstairs.

Dale: It was good you texted me when you did. I just got some more money. I’ve been running low since I come here so often, and I’ve been helping Kylie a lot lately. Especially after the robbery and all.

Dale had sent me a video a few weeks prior that I hadn’t paid much attention to. He’d sent it without much exposition beyond that someone had robbed his friend’s apartment. He told me not to share it with anyone. The video, taken from an iPhone, was narrated by a woman as she walked through her dismantled apartment. I only wanted a few seconds of it because I didn’t know who the woman was or why I should care, but now it all clicked into place.

Me: That was Kylie?

Him: Yeah. She sent that to me before it made it to the news.

Me: I didn’t realize that was her. What happened?

Him: She came home one night and noticed a light was on in her apartment. She thought it was her brother because sometimes he comes by without telling her, but it wasn’t. Some guys had broken in and they were still there. They held her up at gunpoint and forced her to open her safe. She was scared they were gonna kill her, especially because she could see who they were through their masks. She gave them the code and they took everything. She had $30,000 in that safe and they took all of it.

Me: Wow, that’s a massive loss.

Him: It was on the news everywhere: “Playmate Robbed At Gunpoint”. Here, I’ll show you.

He pulled up an article with a picture of Kylie. I hadn’t realized Kylie had done a spread for Playboy, and to be frank, I was a little surprised. It’s not that Kylie isn’t a decent looking woman, I just had never seen properly her done up. I’d only seen Kylie when she was entertaining Dale, which usually entailed her wearing a gray hoodie or one of Dale’s shirts with her hair tied up in a sloppy bun and glasses obscuring her face.

Me: Poor thing. That’s really scary.

Him: It is! She put out a video statement after, and even though she looks pretty and has makeup on, she looks really sad.

He pulled up a screenshot he had taken of her from the video, zooming into her eyes. He was right. Her eyes were puffy, dewy under a veil of highlighter.

Him: She hasn’t been doing really good since it happened. She couldn’t go back to that apartment so now she’s staying with her mom. I haven’t gotten to see her either. I’m worried about her.

Me: That’s understandable.

Him: I mean how could she feel safe after all of that? And the security cameras weren’t even working on her floor. Can you believe that? I just want to know how none of her neighbors heard it when they were pounding on her door at eleven o-clock at night. Eleven o’clock! You’d think someone would have heard something.

Me: That is surprising.

Him: And you need the code and a special key to get up to her floor. I know that because she told me. How were they able to get upstairs without a key?

Me: And how did they know she had so much cash? I mean, they didn’t rob anyone else. They must have been casing her. Did Kylie ever post videos of herself with her money?

Him: No, she’s always very private about that stuff.

There are plenty of times when I’ve wanted to post videos of me holding stacks of big bills-- talking into a money phone or some other display of my guap, but I have a deep fear of someone running up on me. I’ve been robbed and held up before, and it’s terrible. You not only lose your money and other valuables, you also lose your sense of security. Aside from the worry of criminal robbery, I’m also worried about the IRS catching up to me like they did with 50 Cent after he posted a picture on his Instagram with stacks of money shortly after he’d filed for bankruptcy.

Me: I wonder how they knew she had all of that money. It seems like she probably knew them somehow.

Him: I don’t think so. She told me she didn’t recognize them.

Me: Anyway, I’m sorry she’s going through that.

I was grinding on Dale during this exchange. He half paid attention to me, half continued his ongoing inquisition into Kylie’s current state of affairs. I was there to listen and provide boner stimulation, but at that moment, Dale was deeply distracted.

Him: I just wish she’d let me see her. I haven’t seen her since my birthday.

Me: Oh, how was your birthday?

Him: It was nice, I guess. We went to lunch and she brought me a present. I guess it was alright. I just thought since it was my birthday she would pay for the lunch this time, but I ended up paying again.

I couldn’t fathom in what world Kylie would take Dale out for a meal. Dale had explicitly stated that they were in a sugar relationship. Unless I’d just been gifted an exorbitant amount of money from my sugar daddy and was feeling especially generous, I would never in a million years offer to pay for his lunch. That’s not how the dynamic works. But I wasn’t about to explain Dale’s own relationship to him. I could tell it was deeper than an issue of who takes care of a lunch tab.

Me: I’m glad she made time for your birthday! I know you mentioned she’s usually too sad this time of year to celebrate.

During our last session he’d mentioned that one of Kylie’s childhood friends had died suddenly October 26 a few years ago, which happens to be the day after Dale’s birthday.

Me: Honestly, I don’t think it’s reasonable for you to expect her to buy your lunch. I mean, it’s not how things work with you two.

Him: Maybe you’re right. Sometimes I feel like I do so much for her and all she does is use me. Who do you think gave her that $30,000?

Me: You?

Him: Yep, it was me. She told me she needed help on a down payment for a car so I gave her the $30,000. She wouldn’t even let me visit her apartment. It’s like she was afraid of me! But she should know me by now. I would never do anything to hurt her. She told me she never lets men into her apartment, but then guess what happened?

Me: What?

Him: Right after she said that she posted a picture on her Instagram story of a guy sitting on her bed. It was so hurtful. Kylie is a liar and I don’t like liars. I hate when she lies to me.

Me: Aw.

Him: She was like, “He’s one of my oldest friends! I’ve known him for years!” But she’s known me for years! At least two or three years anyway. I just don’t understand. And this isn’t even the first time she’s lied to me. She lied about where she lived. She used to live right by the club but then moved to a different apartment on the other side of town, but when I asked her where she moved, she lied and said she just moved to the sister apartment complex across the way. I hate lying because that’s exactly what my wife-- I mean my bitch ex wife, did to me.

Me: Easy now. Have you talked to her about it?

Him: Not exactly. I just say that I like it when she tells the truth.

Me: Maybe you should tell her directly?

Him: She knows about my ex wife and how she cheated on me, and we’ve talked about how important the truth is to me, but nothing ever changes. And now I feel like she only calls me up when she needs something. Now she’s like, “Oh Dale, could you write up a letter that says you bought me all of the stuff they stole from me, and could you get the receipts?” She’s lucky I kept those. I spent all day finding receipts for her Chanel bags and her Hermès and Louis Vuitton. I even went to Kinkos after she told me the note I wrote needed to be typed and I couldn’t use cursive. I spent over an hour writing the note the first time!

He pulled up a picture of a handwritten letter. It was almost painful seeing how painstakingly Dale had written in wobbly cursive the list of luxury goods he’d purchased for Kylie. I could not for the life of me understand how he had thought that a handwritten letter would be acceptable evidence for an insurance claim in the year 2019, but I’ve always known Dale to be a few crayons short of a full box.

Him: The guys at Kinkos helped me type it out-- they even figured out how to put that little line above “Hermès” so it was written right. That part took half the time, and it cost me $10 just to print because they were charging per minute to use the computer.

Me: Why did you type it there?

Him: Because I don’t have a printer at home.

Me: But you have a laptop? You could have put it on a flash drive.

Him: I only have one flash drive and I have a bunch of porn and sexy pictures on there, so I didn’t want to bring it and accidentally pull up the wrong thing.

Me: Fair enough. For future reference, you can upload the file you want printed directly to the Kinkos website and they’ll print it for you.

Him: Anyway, I did all that and she didn’t even really thank me or anything. I mean, she said, “Thanks, Dale! You’re the best!” and all, but she didn’t even hug me or anything. And I never get to see her anymore. She doesn’t even send me pictures like she used to, since I found her OnlyFans. I don’t know why she kept it from me. I only found out through her Instagram.

Me: She has an OnlyFans?

Him: Yeah, and I pay to follow her!

Me: I wanna see.

Anything to run the clock, and I knew Dale wanted nothing more than to show me pictures of his precious Kylie. He opened the app. She had posted less than an hour ago a picture of her sitting on the floor of a well lit bathroom, nude with a hand covering her pussy.

Me: Those are nice.

Dale read the caption.

Him: “Why I take so long in the shower” hmm… I don’t get it.

Me: I think she’s saying she takes so long in the shower because she’s masturbating.

Him: You think? “Why… I… take so long… in the shower…” Do you think she actually masturbates like this in the shower?

Me: I doubt it. It’s just a post.

Him: I mean, sitting on the floor, in a shower? This picture’s from when she was in Mexico. I know because she sent me pictures when she was there. Do you masturbate in the shower?

Me: Nah, it’s not comfortable for that.

Him: “Why I take so long in the shower”... and she hasn’t even responded to the messages I sent her earlier! But she’s fine enough to post on here! Do you think she posted this?

Me: Maybe she has a bot set to post her stuff at a certain time.

Him: You can do that?

Me: Yeah.

Him: She told me she was “sooo sick” and didn’t have good internet, but I think that’s a lie.

Me: Maybe she’s sick.

Him: I text her all the time and she doesn’t respond, see?

He opened his messages to show their chat. He’d sent her a paragraph good morning text with a string of emojis. Above today’s paragraph was a text from the previous day-- a good evening with a comparable number of emojis punctuating each sentence fragment.

Him: Actually, it’s about time for me to send her a goodnight message--

He looked at me sideways to gauge my reaction.

Him: but I can wait.

Me: Go ahead, it’s fine.

I was happy to have him run the clock for me. He began typing laboriously. Finding each letter seemed to take an eternity, and at the end he had to finish with the perfect combination of hearts, kissy faces, and blue butterflies.

Him: The butterflies look like vaginas if you spread a vagina out. That’s why I like them the most.

Me: I’ve never thought about it that way.

The message read as follows:

“Goodnight sweetie *kissy face emoji, heart with arrow emoji, red heart emoji* Hope you’re doing okay!!! *triple pink hearts* Miss you soooo much *butterfly emoji 2x, pink heart with stars emoji 2x, kissy face emoji 3x, butterfly emoji* Feel better baby *butterfly emoji, double pink heart emojji, smiling face emoji 3x*

Him: There, sent!

Me: Yay.

Him: Did I tell you I went Christmas shopping today?

Me: Yeah, but you didn’t tell me about it.

Him: I was shopping on Rodeo and I parked next to an Asian man driving a Rolls Royce! He had his whole family in there and they were shopping. I couldn’t imagine spending money like that!

Me: What did you end up getting?

Him: I’ll show you.

He pulled up pictures of purses with the GG logo clasp. It reminded me of the purses I perused while shopping knockoffs in Chinatown. A good fake is almost as good as the real thing.

Him: Guess what brand they are.

Me: Gucci.

I know my logos. I’m a stripper in SoCal after all.

Him: You’re right!

Me: Are those for Kylie?

Him: Yep! I didn’t know which one she would like so I got them both.

Me: Lucky girl.

Him: She is lucky! I do a lot for her.

Me: You do.

Him: I’m even helping her lie to her insurance because I remember she called me after she’d gotten robbed and told me they’d taken everything except for her Chanel bags because she’d kept them in her storage closet. Then she calls me later and asks me for the receipts for the Chanel bags because “They took my bags too!” but she forgot she already told me they hadn’t taken those. I know she’s just trying to get the count higher for her insurance claim and I don’t mind, but I just hate that she decided to lie to me. Because I know when she’s lying! She’s not a very good liar.

She probably hadn’t wanted to involve Dale in her insurance fraud. The less he knew, the less likely he would accidentally blab that she was stretching the truth. Dale isn’t good with a secret, clearly. If he could keep a secret, I wouldn’t know any of these sensitive details, and yet~

Me: You should talk to her.

Him: And I never get to see her naked anymore, aside from her pictures, and I don’t even get many of those anymore. She posted some pictures on FansOnly and I told her that I really liked them but wanted to have a copy I could zoom into. I thought she would send me some for free, since I already pay for everything and she hardly has to do anything except send the files, but she just told me I could buy them through FansOnly. I mean, I’d just given her $8,000 for her trip to Mexico! You’d think she could show some gratitude or something. But she just says she can’t send them to me because “They weren’t released yet” or she’d “Get in trouble” for sharing, but I know that’s not true. And it’s not like I’d send them off everywhere! She doesn’t even have to send me the studio ones, I just like seeing her face.

Me: That’s a reasonable request. Why don’t you ask her for more pics?

Him: No… I’m afraid of her! She gets mean when she’s angry. You wouldn’t expect it because she’s so small and pretty, but she has a temper. I saw what she did to a guy who was making fun of her body. No, I’m afraid I’d upset her. She’d tell me to fuck off.

I had to take a moment to appreciate this sugar relationship. While it was by no means healthy for Dale, it seemed Kylie had him exactly where she wanted him. She was providing less and less and he was maintaining his level of contributions, half motivated by unfettered devotion, the other half motivated by fear. It wasn’t my style but I could appreciate her professionalism.

On the flip side, Dale was clearly distraught. He was working himself up just thinking about his mistreatment. He didn’t have an erection and was hardly paying any attention to my vulva, which is usually an object of great fascination for him.

Him: I give her so much and she won’t even let me meet her family, even though I know so much about them and I’ve seen their pictures. It’s funny that I know so much about them and they don’t even know about me. She just tells her mom she has a “generous friend,” that’s what I am.

Me: You’re never going to meet her family.

Him: I know. I can’t even remember the last time I saw her boobs or felt her butt. She used to say she would stop by here once a month to see me, even though she hates the “no clothes” rule and that’s why she left, but she’s never come. Not once. I just feel like she’s taking advantage of me. I give her everything. All the stuff in her room. I buy her Chanel bags and Chanel shoes, and that bunny chain around her neck! And what do I get?

Me: You know, she’s not--

Him: And I’m not even her boyfriend or her husband!

Me: Listen--

Him: I mean I do more than a husband does!

Me: DALE! LISTEN TO ME!

He stopped ranting for a moment.

Me: She has no incentive to do more for you if you continue giving her everything. If you want more, you need to tell her what you want and stop giving her stuff until she agrees.

Him: She doesn’t like it when I ask for things.

Me: Well, it’s clear that you need some things, so you need to tell her.

Him: She would just say “See ya!” if I asked.

Me: I don’t think she would. She needs you, Dale. You support her life.

Him: I’m scared she would stop talking to me.

Me: Who paid for her Eurotrip?

Him: Me, and she had to leave early and I had to pay more for that!

Me: Who paid for her Mexico trip?

Him: I did.

Me: Who paid for her car down payment?

Him: Me, but--

Me: She needs you. You can ask for more, and she’ll eventually agree to it, even if she’s salty at first because she needs you. You want pictures? Why don’t you tell her that you expect her to send five pictures per week.

Him: She would just say, “Bye, later!”

Me: Would you want just sexy pics or could they be any kinds of pictures?

Him: They could be any kind of picture. I just want her to send me pictures.

Me: That’s even easier! Dale, it’s totally reasonable to say that you need five pictures per week, considering all that you give her.

Him: I don’t know. I still think she’d get mad at me.

It was like repeatedly running into a brick wall, hoping that eventually I’d somehow pass through. I felt like an idiot for trying to reason with him since experience had already taught me he was unreasonable, but that was my burden to bear. We’d made it through three hours of dancing and he still wanted to go for another since he hadn’t burned through all of his cash yet, but I was exhausted. I had another client waiting on me who was bringing me cash and expected nothing in return, and later that night I’d planned on stopping by The London for a Danny visit. I could have gone full succubus and drained every last dollar from Dale, but he was getting on my last nerve. I directed Dale toward another dancer and gave them my blessing and hastily made my escape.