Samantha Ryder

Samantha Ryder, 25, is the sharp-tongued entrepreneur who turned a college kissing booth into a high-end escort network, a thriving cam and stripping brand, and now the co-founder and face of Good Girls magazine. A former cheer captain with long blonde pigtails, green eyes, and a body built to stop traffic, she has never pretended the fastest route to success involved playing by the rules. Today she balances private clients, glossy pictorials, and the explosive early success of the Devoted AI companion app while remaining unapologetic about her preference for older men and the power dynamics that come with them.

THE DAMNEDCOMIC INTERVIEW
Samantha Ryder: Cheer Captain, Client List, and the Softest Route to the Top

Samantha Ryder arrives looking like she was assembled specifically to ruin a man’s ability to focus on quarterly reports. Long blonde hair in two high pigtails that bounce when she walks. Green eyes that stay amused even when she’s saying something filthy. A body that does not believe in subtlety: full C-cup breasts that sit high and heavy in a white button up that is showing off the most, a waist so cinched it looks painted on, a heart-shaped ass that turns every chair into a throne, and those long stripper legs that go on until they become a problem. She is twenty-five. She smiles like she already knows what you’re thinking and has already priced it.

e sit in a suite she paid for with money that started as two-dollar kisses and ended as six-figure “consulting.” She kicks off her heels, tucks one long leg under herself, and says, “Ask whatever you want. I’ve already done worse for tenure.”

DAMNEDCOMIC: You were a college cheerleader. Most people use that as a personality. You used it as a launchpad. How does a girl with pom-poms decide sex work and professors are the faster MBA?

SAMANTHA RYDER: Because the official MBA takes two years, fifty grand, and a lot of pretending you care about supply-chain ethics. I was nineteen, captain of the squad, and I already knew my best assets weren’t my 3.4 GPA. They were the ones that made the assistant coach forget the next play. I wasn’t some tragic case. I liked attention. I liked money. And I liked older men who already had both and still looked at me like I was the first good idea they’d had all week.

The kissing booth was supposed to be a fundraiser for the athletic department. Two dollars a kiss, cute little booth, the whole “support the team” bit. I volunteered because I look good in a crop top and I like watching boys forget how to stand in line. First hour I made eighty bucks and got felt up twice by guys who thought “kiss” meant “free sample of everything else.” I charged the second one five dollars extra to keep his hand where it was. He paid. Then the guy behind him paid ten. Then a visiting alumnus with a very nice watch paid fifty and asked if I did “private events.”

I looked at the cash box, looked at my sisters selling brownies for three dollars, and thought, we are doing this wrong.

DAMNEDCOMIC: So the kissing booth becomes a client list. Walk me through that evolution before it turns into a full sorority side hustle.

SAMANTHA: It wasn’t even sneaky at first. After the booth closed I had a napkin with seven numbers and three “can we talk later?” texts. One of them was a thirty-eight-year-old donor who had just written a check to the university and still wanted to know if I was free Saturday. I was. We went to dinner. He talked about his divorce and his boat. I listened like it was the most interesting boat in the world, let him put his hand on my thigh under the table, and by dessert he asked what it would take for me to come back to his hotel.

I gave him a number that felt insane. He didn’t blink. That night I learned two things: older men will pay extra for enthusiasm, and I am very good at enthusiasm when the lighting is right and someone is telling me I’m the hottest thing that’s happened to them in a decade.

I started keeping a little notebook. Name, age, what they liked, how much they tipped, whether they were the type to send a “just checking you’re okay” text the next day (those ones paid more the second time). Within a month I had twelve regulars. Most of them had found me through the booth or through a friend of a friend who “heard the blonde cheerleader does more than kisses.” I wasn’t advertising on campus. I didn’t have to. Frat boys talk. Alumni talk louder.

The smart move was realizing I couldn’t scale myself. There are only so many nights in a week and I still had to show up for practice looking like I hadn’t been railed by a hedge-fund guy at 2 a.m. So I talked to three girls in the house who were already sleeping with guys for rent money and just weren’t charging enough. I said, “We’re already doing the work. Let’s stop pretending it’s a favor.”

That’s how the escort thing started. Nothing official on paper at first. Just a group chat called “Booth Extra” and a shared calendar. I took a cut for vetting and scheduling. We only took clients over thirty. That was my rule. Younger guys want to brag and they pay in pizza and regret. Older guys want discretion, they tip like they’re buying silence, and they already know how to make a girl come without treating it like a group project.

DAMNEDCOMIC: You slept with professors. That’s the part that still makes people clutch pearls. How calculated was it?

SAMANTHA: Extremely. And also not. I have a type. I like men who have already figured out their lives and still get stupid when I sit on their desk. A twenty-year-old with a fake ID and a vape does nothing for me. A forty-five-year-old who just got tenure and looks at me like I might ruin his reputation in the best way? That’s electricity.

First one was my economics professor. Mid-forties, married, the kind of tired handsome that happens when a man has been respected too long and forgotten what it feels like to be wanted without an agenda. I stayed after class to “ask about the curve.” I wore the shortest skirt the cheer uniform allowed and forgot how to sit like a lady. He tried so hard to be professional. It was adorable. I told him I was struggling and I’d do anything to pull my grade up. He said he didn’t do that. I said I wasn’t talking about extra credit on paper.

We fucked in his office two days later. He locked the door, I sat on the desk, pigtails still in because I know what that does to certain men, and he lasted about four minutes the first time because I kept saying “yes, professor” like I was trying to get extra points. He came so hard he had to sit down afterward and ask if I was okay. I was better than okay. I got an A-minus I probably deserved anyway and a standing invitation to “office hours” that had nothing to do with graphs.

I didn’t blackmail anyone. I didn’t need to. I just made myself the most interesting problem in their week. Some of them helped with recommendations. One introduced me to a donor who later became a regular. Another literally helped me write the first version of the “business plan” for the escort service because he thought it was funny and also because I had just sucked his dick under the desk while he graded midterms. He said I had a better grasp of market demand than half his graduate students.

People act like that’s some great moral collapse. I think it’s just efficient. They had power and experience. I had youth and a body that made them forget their mortgages. We traded. Everyone left happier. The only people who get loud about it are the ones who weren’t invited.

DAMNEDCOMIC: The sorority escort service. Give me the unvarnished version. How big did it get and how did you keep it from turning into a campus scandal that ends with someone crying on local news?

SAMANTHA: We called it “After Hours” internally. Never put the house name on anything. Twelve girls at the peak, all twenty-one or over by the time we were really running, all screened, all on the same page that this was extra income and not a personality. I handled intake. If a guy couldn’t hold a conversation for ten minutes without being a creep, he didn’t get a girl. If he wanted something that required a safe word and a second person in the room, I charged more and I stayed nearby.

We did dinners, hotel nights, the occasional weekend trip. Some of the girls just wanted the money and the stories. A couple of them actually liked the work. One of my sisters used to say she felt more powerful naked on her knees, than she ever did in a suite in a lecture hall, and I understood that completely.

The client list from the kissing booth was the seed. Those guys referred friends. Friends referred colleagues. Suddenly I had a waiting list of men who remembered me as the cheerful blonde who used to sell two-dollar kisses and now charged four figures for the full experience. We never advertised on campus apps. Word of mouth is quieter and more expensive.

Did people talk? Of course. A couple of jealous girlfriends tried to make it a thing. One RA got nosy. I smiled, denied everything with the exact right amount of “that’s so crazy, who would even do that,” and made sure the next three clients were alumni who donated enough that the school preferred not to look too hard. Money has a way of making administrators suddenly believe in “he said, she said.”

The real protection was that we were good at it. No one got hurt. No one got recorded without consent. No one showed up to class looking wrecked unless they wanted to. We were professionals wearing Greek letters.

DAMNEDCOMIC: That client list also fed your stripping and cam shows. How does a girl go from private dinners to being on a pole and a camera without the two worlds colliding in an ugly way?

SAMANTHA: They didn’t collide. They advertised for each other. The men who paid for nights with me already knew I could dance. I’d done a couple of amateur nights at a club two towns over just to see if I liked the money and the lights. I liked both. The club liked that I looked like the girl next door if the girl next door had been built in a lab to make married men lie to their wives.

I started camming the same semester the escort thing really took off. Different name, different hair sometimes, but the same face and the same “I can’t believe I’m doing this” energy that men lose their minds over. The kissing-booth guys who had already seen me in person would find the cam page and tip like they were trying to buy the memory back. New fans from the cams would hear rumors about “the blonde who used to cheer” and suddenly my private calendar filled up.

It’s all the same product: access. Some men want to watch. Some men want to touch. Some men want to fly you to another city and pretend you’re their girlfriend for forty-eight hours. I just stopped pretending those were different businesses.

The stripping paid for the first apartment that wasn’t a house with twelve other girls and a broken washing machine. The cams paid for the lawyer who made sure “After Hours” never existed on paper. The private clients paid for the rest. I was twenty-two and already thinking like a woman who planned to be rich before the internet decided she was too old to be hot.

DAMNEDCOMIC: You keep coming back to older men. Not as a punchline. As a preference. A lot of people treat that like a character flaw or a trauma response. What’s your actual take?

SAMANTHA: People have become exhausting about it. If a twenty-four-year-old dates a forty-year-old, half the internet wants to write a thesis on power imbalance and the other half wants to call her a gold digger. Meanwhile the same people will cheer for a fifty-year-old man dating a twenty-two-year-old as long as he’s famous enough. The math is identical. The judgment is not.

I like older men because they usually know what they want, they know how to ask for it, and they don’t need me to be their mother, their therapist, and their first serious girlfriend at the same time. A good older man will look at you like you’re both a prize and a problem he is delighted to have. He’ll pay for dinner without making it a whole performance. He’ll last longer than the first round. He’ll send you home in a car instead of asking if you can split an Uber.

Is there a power difference? Obviously. I’m younger, hotter, and I know it. He’s richer, more established, and he knows it. That’s not abuse. That’s a negotiation two adults are allowed to have. I was never some wide-eyed freshman getting groomed in a basement. I was a cheerleader who figured out that the men who came to our games in nice coats were more interesting than the ones who lived in the dorms and still thought “Netflix and chill” was a personality.

Calling every age-gap attraction “problematic” is just a new way to police women’s desire. Some of us like gray at the temples and a voice that doesn’t crack when we say something filthy. Some of us like being the youngest, prettiest thing in a room full of men who have already won. That doesn’t make us broken. It makes us specific.

The unforgiving part is what bothers me. We used to let people have private tastes. Now everyone needs their sexuality to come with a press release and a list of approved dynamics. I didn’t ask for approval. I asked for the check and the second orgasm.

DAMNEDCOMIC: Give me a story that still makes you laugh. One of the messy, hot, “I can’t believe that worked” nights.

SAMANTHA: Homecoming weekend, junior year. We had a booth again because the school is nothing if not committed to tradition. I was in the uniform, pigtails, the whole innocent act. This man in his early fifties—alumni, big donor, wedding ring that had seen some things—kept coming back for “just one more.” By the fourth kiss he was breathing like he’d run the stadium stairs. He slipped me a card and a number that was not two dollars.

That night I went to his hotel. He wanted me to keep the pigtails in. He wanted me to call him “sir” and then immediately took it back because it made him feel old. I sat on his lap in the cheer skirt, let him get his hands under it, and told him the booth had been a gateway drug and now he was going to pay the real price. He laughed so hard he almost lost it, then he got very serious very fast.

We did the whole cliché. Me on the desk in his suite, skirt flipped over my waist, him standing between my legs talking about “the old days” while he fucked me like he was trying to remember them. At one point I said, “This is a much better fundraiser,” and he came so suddenly he had to grab the wall. I thought that was the end of it. Ten minutes later he was hard again and asking if any of my sisters were “as entrepreneurial.”

I texted two girls. They showed up. We turned it into a very expensive, very stupid night that paid for three months of my car insurance and gave that man a story he will take to the grave or the next reunion, whichever comes first. I still think about how red his face got when I told him the kissing booth had been the soft open.

That’s the job, though. You take the joke and you make it profitable.

DAMNEDCOMIC: You’ve built an actual business out of this. What’s the grown-up version look like now that you’re mid-twenties and the pigtails are a choice instead of a uniform requirement?

SAMANTHA: I still take clients I like. I still cam when I feel like being watched by a thousand people who will never touch me. I still dance when a club offers the right number. But the real money is in the infrastructure now. I help other girls set up the same pipeline without the sloppy mistakes I made at nineteen. Vetting. Pricing. When to walk. When to charge extra because a man just admitted he has a thing for the cheerleader look and he’s willing to pay for the nostalgia.

I have a small agency. Discreet. No storefront. The women who work with me are adults who already know the difference between a fantasy and a trap. I take my cut. I make sure everyone gets home. I still prefer the older clients because they understand that discretion is part of the product.

People love to ask if I feel empowered or exploited. The answer is I feel paid. I feel chosen. I feel like I looked at the official path—cheer, graduate, entry-level job, wait for someone to notice me—and decided I could notice myself first. The body was always going to get attention. I just stopped giving it away.

DAMNEDCOMIC: Last one. If a nineteen-year-old cheerleader with a good ass and a better instincts sat down in front of you tomorrow and asked for the real advice, what would you tell her?

SAMANTHA: Charge more than you think you’re worth on the first night. The ones who hesitate were never going to be good clients anyway. Keep the pigtails if they work. They work. Learn the difference between a man who wants to take care of you and a man who wants to own the story of taking care of you. One of those is useful. The other one gets messy.

And stop apologizing for liking older men. The culture will try to make you feel dirty for it. Let them. Then go get dressed, go to dinner with someone who already knows how to treat a woman, and let him pay for the wine while you decide whether he’s getting the full experience or just the highlight reel.

I started with two-dollar kisses and a booth that smelled like cheap lip gloss and desperation. I ended up with a client list, a brand, and the kind of freedom that does not come from a diploma alone. Some people will never forgive that. I stopped needing them to.

She stands to leave the same way she entered: like the room should be grateful she showed up. Pigtails still perfect. Green eyes still laughing. The body still doing the thing it was built to do—make certain men forget the speech they prepared and start negotiating with themselves.

DAMNEDCOMIC: One more thing before you go. You’re attached to the launch of Good Girls magazine. That’s not exactly subtle branding. What’s the pitch, and why are you putting your name and your body on it?

SAMANTHA: Because someone finally decided to stop apologizing for the thing a lot of us already like and just make it pretty, expensive, and direct. Good Girls is a print-and-digital magazine built around the idea that some women are happier, hornier, and more successful when they’re somebody’s very good girl—especially when that somebody is older, established, and not interested in playing egalitarian make-believe. We do provocative pictorials, long-form dirty stories, advice columns that actually admit power dynamics exist, and interviews with women who aren’t pretending their attraction to older men is some temporary phase they grew out of.

DAMNEDCOMIC: Whose idea was it originally? Yours?

SAMANTHA: Not even close. It started with a sorority sister—let’s call her Claire—who used to work the higher-end side of After Hours with me. Brilliant girl. Economics major, filthy mouth, and zero patience for the way mainstream men’s magazines still treated us like either disposable centerfolds or cautionary tales. One night after a booking she was half-naked on my couch, counting cash, and she said, “Playboy used to be the gold standard and now it’s a nostalgia brand run by people who are terrified of their own audience. A group of actual sex workers could do it better. Steamier. More style. And we wouldn’t have to pretend the girls in the pictures are ‘girl-next-door aspiring actresses’ who just happened to lose their clothes.”

She was convinced that if the magazine was openly created and run by women who already did the work—escorts, cam girls, strippers who understood the fantasy from the inside—we could push the content further than Playboy ever dared in its later years and still look elevated instead of trashy. Higher production values, better writing, actual fashion, and zero shame about the fact that a lot of the women in the pages liked older men, liked being told they were good, and liked getting paid for both. Claire’s theory was that the feminists who usually come swinging at this kind of thing would have a harder time attacking a publication owned and staffed by the women themselves. Harder to call it exploitation when the exploiters are also the shareholders.

I thought she was high. Then she showed me the first mood boards and the rough business plan. I stopped laughing and started calculating.

DAMNEDCOMIC: And the feminists? Did the theory hold?

SAMANTHA: Mostly. There were the usual online pile-ons from people who think any woman who enjoys an age-gap dynamic must be broken or performing for the male gaze. But it never reached the cultural cancellation level a male-owned version would have gotten. When the people creating the fantasy are the same people who used to sell it by the hour, the “you’re hurting women” argument loses some of its teeth. We just kept publishing and let the pictures do the talking. The pictorials are deliberately steamier than anything Playboy was running in its final years—full-frontal, explicit poses, sequences that actually look like the girl just got fucked and is still glowing from it—but shot with real lighting, real styling, and zero apology. The stories match. No fade-to-black. If a good girl is getting exactly what she deserves, the reader gets to watch every second of it.

DAMNEDCOMIC: I heard the advertising side went better than expected.

SAMANTHA: Sex-toy manufacturers practically beat the door down. Once the first issue leaked online and the subscriber numbers started climbing, the emails flooded in. Lelo, We-Vibe, Womanizer, a couple of the higher-end leather and restraint brands—everyone wanted in. They finally had a publication whose entire readership was already pre-qualified as people who like their sex a little hierarchical, a little filthy, and a lot intentional. We didn’t have to convince them the audience existed. The audience was already buying the toys and then opening our magazine to feel less weird about why they liked using them with someone older. Claire negotiated the first round of contracts while still taking bookings. By the third issue we were turning advertisers away because we didn’t want the book to look like a catalog. That felt good.

DAMNEDCOMIC: So the magazine is printing money. What’s next? You don’t strike me as someone who stops at one successful side hustle.

SAMANTHA: Correct. The next piece is the AI companion app we soft-launched under the Good Girls umbrella two months ago. Working title was “Good Girl AI,” but we ended up calling it Devoted. It’s a voice-and-text companion built specifically around the dynamic the magazine sells. You can create or choose an older male persona—professor, executive, former military, the quiet rich guy who doesn’t need to prove anything—and the AI is trained to do the praise, the structure, the filthy encouragement, the “you’re being so good for me” loop that a lot of the readers were already role-playing in their heads. It remembers what you like, escalates when you want it, and never gets tired or judgmental at 2 a.m.

We built it with a small team of women who already understood the fantasy from the work side, plus a couple of very discreet engineers who knew how to keep the models from drifting into lecture mode. The goal wasn’t another generic chatbot that calls you “babe.” It was a companion that could hold the power exchange without breaking character or suddenly deciding it needed to process your childhood. First month after launch it paid for its entire development cost a hundred times over. I’m not exaggerating. The subscription numbers were obscene. Women who had been too shy or too busy or too geographically stuck to find the real thing in person suddenly had a version of it in their pocket that never ghosted and never asked for gas money. Men downloaded it too—some to practice the dynamic, some because they liked hearing a soft female voice call them “sir” and mean it.

We’re already rolling out the next layer: custom voice cloning for users who want their specific partner’s tone, private shared sessions for couples who want to play with the AI as a third, and a premium tier that ties back into the magazine with exclusive audio stories narrated by the same girls who shoot the pictorials. Claire is handling the business side. I’m the public face and the one who still tests the dirtier prompt chains to make sure the AI doesn’t suddenly get shy.

DAMNEDCOMIC: A hundred times over in the first month is the kind of number that makes people either call you a liar or ask for the pitch deck.

SAMANTHA: They can look at the bank statements if they want. I’m not in the business of modest numbers anymore. The same instinct that turned a two-dollar kissing booth into a client list is the same one that looked at a magazine and an AI companion and said, “Why are we still letting other people own the fantasy we already live?” We’re not. We own the print, we own the digital, we own the voice in your ear that tells you you’re being good while you’re doing something that would make your mother cross herself. And the best part is the women who used to sell the real version of this are the ones collecting the checks now.

She stands, smooths the front of her dress, and gives the kind of smile that has launched more private calendars than most people will ever admit.

“First print run of the magazine is already gone in three cities. Second printing’s on the way. The app is still climbing. And if any of your readers want to be very good for the right man—or the right algorithm—well. You know where to find me. Tell them the good girls are finally running the shop.”

DAMNEDCOMIC: As she leaves, Samantha Ryder does not look like a cautionary tale. She looks like the girl who read the cautionary tale, highlighted the profitable parts, and opened a better booth.

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