u/Charsfun

For men in a certain income bracket, there's an assistant or service that can help with literally any facet of life. Private chefs, personal schedulers, high-end private travel agents, and on and on - when your time is the most valuable asset, a truly rich man finds a way to turn his 24 hours a day into even more time.

This rule holds true for rich men looking for help with their interpersonal relationships too: high-end matchmaking services have been a thing for years. But in a small townhouse on the Upper West Side, there was a business that was a little less well-known that provided a more niche service.

Sweetness wasn't a dating service in the traditional sense. The men who paid its high registration and monthly fees weren't looking for wives or girlfriends. No, Sweetness was a sugar baby matchmaking service. The kept profiles on interested and eligible younger women across the US, mostly college students and all younger than 25, to be examined by appointment only.

The profiles were informative, but not exhaustive. Liza, Sweetness' 30-something founder, was fond of saying that no profile was as informative as a first date. Every woman answered the same question to start their profile: In 500 words or less, what would you do differently if you didn't have to worry about money for the next two years?

If a man liked a profile, the woman would be contacted. If the interest was mutual, she'd usually get flown to New York on her prospective Sugar Daddy's dime. Liza also like to arrange mixer and trips for her most intriguing clients; a European yacht trip the summer before had produced a 100% match rate. Sweetness was a dirty little secret, but it was one that worked.

***
Hi! Today I'm looking for a partner for a new story. Sweetness is a sugar baby matching service for the wealthiest men to find their perfect younger woman to spoil. This prompt can go a lot of different directions, so it would definitely benefit from some discussion OOC!

This dating service model could benefit character creation, if we decide we want to create an interesting man and start with him walking into the Sweetness townhouse for a consultation, but I'm open!

Let's talk OOC about sugar relationships and age gaps and what kind of story we might like to tell! I'd love to connect!

The breakup had hit Sophie like a freight train. She'd really been in love with Derek: he'd been her first everything dating back to welcome week of freshman year, and she'd thought they might be in things for the long haul. He'd shattered those illusions coming back from Christmas break of junior year. He'd had a whole story about finding himself and not being ready to commit long term, but she hadn't cared. That had been the last day they spoke.

It wasn't the thing that hurt the most getting dumped out of the blue, but Sophie had bought Derek a REALLY good birthday present and not given it to him yet. His favorite band was right in the middle of a world tour, and she'd splurged: meet and greet backstage, pit access, the whole nine yards. He'd have been over the moon, and it hurt Sophie to think about how much she'd spent on a gift that would never get used.

She could dump the tickets on the resale market and basically make all of her money back, but the meet and greet was non-transferrable. It had to be her and a guest, or no access. The contract was pretty explicit. Sophie didn't really think much about the band, it had been Derek's thing and she was just going to be the date. When she raised the issue to her roommate Cassidy, Cass hadn't had to think.

"Just go yourself, take me if you want," she'd said with a shrug. "It'll feel like revenge to do something he'd have enjoyed so much without him. And have you ever seen photos of those guy? Their music is whatever, but Soph they are SO hot."

And so, Sophie and Cassidy had waited until the first weekend of summer break, when the concert was in the next town over. They slipped into the sexiest concert outfits they could get away with, and made their way to the area. Sophie had no idea how that summer would change everything.

***
Hi! Today I'm looking for a partner for a story about sexy revenge. Sophie got dumped by the man she thought would be her forever guy. She and her roommate use the tickets Sophie had bought for his birthday and are going to meet his favorite band in private before the show!

Since this is DPP, you can see where this is going. Sophie already knows the band is a few very sexy men, and her paid meet and greet is going to turn into an invitation to hang out after the show. I've left what kind of band this is intentionally vague, so we'll talk about that together!

And of course a one night stand with your ex's favorite singer is sexy and fun, but I have bigger ambitions here: I'd love Sophie to turn groupie for her ex's favorite artists and spend the summer on the road with them, in casual relationships with some or all the members of the group! She'll have drinks, drugs, and dicks on demand and who knows? Maybe there will be a single called Sophie on their next album?

If you're F-identified and want to work a queer angle in here and make the idea less hetero I'm very open to that too! Let's make something hot and fun together, and enjoy a little revenge on a shitty ex!

The breakup had hit Sophie like a freight train. She'd really been in love with Derek: he'd been her first everything dating back to welcome week of freshman year, and she'd thought they might be in things for the long haul. He'd shattered those illusions coming back from Christmas break of junior year. He'd had a whole story about finding himself and not being ready to commit long term, but she hadn't cared. That had been the last day they spoke.

It wasn't the thing that hurt the most getting dumped out of the blue, but Sophie had bought Derek a REALLY good birthday present and not given it to him yet. His favorite band was right in the middle of a world tour, and she'd splurged: meet and greet backstage, pit access, the whole nine yards. He'd have been over the moon, and it hurt Sophie to think about how much she'd spent on a gift that would never get used.

She could dump the tickets on the resale market and basically make all of her money back, but the meet and greet was non-transferrable. It had to be her and a guest, or no access. The contract was pretty explicit. Sophie didn't really think much about the band, it had been Derek's thing and she was just going to be the date. When she raised the issue to her roommate Cassidy, Cass hadn't had to think.

"Just go yourself, take me if you want," she'd said with a shrug. "It'll feel like revenge to do something he'd have enjoyed so much without him. And have you ever seen photos of those guy? Their music is whatever, but Soph they are SO hot."

And so, Sophie and Cassidy had waited until the first weekend of summer break, when the concert was in the next town over. They slipped into the sexiest concert outfits they could get away with, and made their way to the area. Sophie had no idea how that summer would change everything.

***
Hi! Today I'm looking for a partner for a story about sexy revenge. Sophie got dumped by the man she thought would be her forever guy. She and her roommate use the tickets Sophie had bought for his birthday and are going to meet his favorite band in private before the show!

Since this is DPP, you can see where this is going. Sophie already knows the band is a few very sexy men, and her paid meet and greet is going to turn into an invitation to hang out after the show. I've left what kind of band this is intentionally vague, so we'll talk about that together!

And of course a one night stand with your ex's favorite singer is sexy and fun, but I have bigger ambitions here: I'd love Sophie to turn groupie for her ex's favorite artists and spend the summer on the road with them, in casual relationships with some or all the members of the group! She'll have drinks, drugs, and dicks on demand and who knows? Maybe there will be a single called Sophie on their next album?

If you're F-identified and want to work a queer angle in here and make the idea less hetero I'm very open to that too! Let's make something hot and fun together, and enjoy a little revenge on a shitty ex!

It was hard to believe that everything had started by flirting at a hotel bar. Darius had just lead his team to a victory in the college football national championship. He'd been on top of the world, but didn't have the energy to go clubbing with his teammates. One drink alone at the hotel bar, then I crash, he had promised himself. At the bar he'd run into Molly Vaughn, the sideline reporter who'd been covering his team through the playoffs. She was older, so confident, and stunningly beautiful. All the guys on the team had a crush on her. One drink had turned into four. They'd gone up to her room, and Darius had learned that he'd been sleeping on divorced women in their late 30s. She'd been the best he'd ever had.

Darius was a 21 year old college football star - he'd never had trouble with one night stands, but Molly was stuck in his head after that night. He'd given her his phone number, hooking up three more times in the semester that followed. He'd never felt a rush quite like knocking on Molly's hotel room door, or the peace he felt after sex when they just lay quietly in each other's arms. They weren't dating, her job made that impossible, but they were having fun together.

Molly had started talking about a summer trip pretty quickly. Since her divorce she'd stopped travelling, but it was her truest passion outside of work. She had a list of places she was still hoping to go, and the Europe section was miles long. Darius had never travelled outside the US, but if Molly was game he wanted to go with her. When she showed him the luxury hotel on the Cote D'Azur she'd been dreaming of, he said yes immediately. Three weeks in Europe with the woman he couldn't let go of felt like a dream come true.

It turned out, there was more to the story. Molly had a friend, another prominent female sports journalist, in a very similar situation. She had a pending divorce, or maybe it had gone through. She'd just taken up with a college boyfriend - a guy Darius had met, but didn't know well. Their little trip became a tryst for two couples to get away.

That was all on Darius' mind as he sat on the porch of a hotel room that cost as much as a month's rent back home, wearing just a robe and enjoying a glass of rose from the mini bar. Molly was in the shower, getting ready to go into town for a nice dinner. He'd join her in a minute. He was really living the high life.

***
Hi! Today I'm looking for a partner for a new story. I really want to write an age gap adventure with older women today! This story follows two football sideline/studio reporters in their late 30s/early 40s who are on vacation in Europe with the early 20s athletic studs. The relationships are new, secret, and sexy! I'm not looking for swapping here, just two couples who are enjoying their honeymoon phase and a fun vacation together to blow off some steam.

I'm open to lots of changes and discussion here - names and locations are not set in stone. I write a lot when I'm engaged with a partner, and love a realistic world to play in. So let's pick real college, real hotels, and make this feel as alive as possible. I'm looking for something long term, so let's talk!

Alice woke up with a shudder, not quite she where she was. Her head was pounding, and the sun streaming through the windows made her bury her head under the pillow. She wasn't a stranger to the feeling of a hangover, and she had a gnarly one. Flashes of the night before came through. She'd definitely had a lot to drink.

As she came to her senses, Alice realized a few more things. She was naked, for one. She was definitely in the hotel where she was staying, but on a much higher floor than her own room. And there was someone asleep in the bed next to her - a woman.

Alice had come to Vegas with her college's athletic department, where she worked as an assistant videographer. She loved her job: it was the closest a quiet, nerdy girl usually got to the bright lights of college sports. She made reels for the players and video packets for the jumbotron at home games. When her team had made it to the national championship, she'd signed on to work on the movie that would go out to alumni afterwards.

Alice was pulled out of her cloudy thoughts when the woman next to her rolled over. Alice's heart stopped. It was Kara Hopper, the head of the university's cheer team. She was also naked, and had the most incredible body Alice had ever seen. Alice felt like she should look away, but couldn't make herself do it. Kara was fucking beautiful.

Kara sat up in the bed, and Alice's heart race when her breasts jiggled with the motion. Kara's eyes were bloodshot, and she rubbed them as if gathering her thoughts.

"Last night was pretty wild," Kara finally said. Alice could barely believe what was happening. She had Kara had never spoken, to the best of her knowledge. Alice identified as bi, but talking to women like Kara sent her into a tailspinning panic. She nodded, hoping Kara would fill in the blanks.

"Do you remember anything? I got so fucked up," Kara laughed softly. Alice shook her head no.

Just then, the door to the hotel room clicked open. Alice's heart raced, unsure of whose room she was in if not Kara's.

The last person she'd expected was Jamaal Ryan, one of the team's defensive backs. He was tall, handsome, and by all accounts a great guy. He was holding three coffees, and walking gingerly though what Alice could only assume was HIS room. He caught Kara's eye first, then Alice's, then sat down on the bed.

"I thought you might need some caffeine," he explained as he handed over two caramel macchiatos. "Last night got pretty crazy."

***
Hi! Today I'm looking for a partner for a fun morning after story. Alice is a quiet, nerdy videographer who went to a party while her college's football team was in Vegas for the national championship. Somehow, she ended up having a threesome with a star player and the head cheerleader, and she doesn't remember much.

I'm open where we go from here! Do they all drink their coffee and deal with the awkwardness of the situation together? Does Kara want to hang out 1 on 1? Does Jamaal let it slip that the players all think Alice is really cute?

This could go a lot of ways, and I'm mostly interested in someone who wants to plan it out with me and make a broad college idea the best it can be!

Lucy Reynolds was getting everything she wanted out of college. She'd been recruited to run track, a sport she loved, and the highest level. There had only been a few people from her small town back in Montana who'd left to go to college in her year. But Lucy's athletic gifts had let her write her own ticket, more or less.

Being away from home had given her freedom. She'd grown up a prim and proper church girl, always looking for ways to please her domineering parents and be the perfect daughter. In college, she'd realized what it felt like not to care. She started wearing makeup, styled her hair how she like, and (most transgressively) started getting tattoos. The art on her body was her pride and joy. Her main piece was a flowing vine that wrapped up one of her legs. It reached from the back of her knee to just under the waistband of her underwear, but was on full display on the track. She had some other small pieces, and they were a visual reminder of who she had become.

Lucy had also started experimenting with sex and drugs as soon as she'd gotten to school. She liked a drink or two at a party, and she'd smoke in a group, but she'd decided the lifestyle wasn't for her. Boys though? That was another matter.

Lucy had always been forbidden to date, and she'd started trying as soon as she'd moved from home. There had been short hookups at first: she'd learned the ropes with a succession of men who didn't know what they had. By the end of her first year, she was ready for something more serious. That's when she'd met Zion.

Zion was the star of her university's football team, and the most famous athlete to walk the campus in years. He was a year older than Lucy, and already tagged as a future NFL prospect. They'd met at a party for athletes to celebrate the end of the year, and hooked up the first night. They'd been inseparable ever since.

As their first anniversary was coming up, they were more in love than ever. Lucy slept at Zion's apartment most nights, and reveled in being the star's girl. She knew the draft was coming, and there was a chance Zion was going off to another city and they'd have choices to make. But she was putting that off as long as she could.

***
Hi! Today I'm looking for a partner for a new story: Lucy is a college student who got out of her hometown and tough family on a track scholarship. She's become her own person, and left her conservative background in the dust. Now she's a sophomore, and coming up on a year dating the school's star football player, who's most likely NFL bound.

How we play this is super open! Do Lucy and Zion have a little accident in the bedroom a few months before the draft? They're fucking A LOT and maybe not that careful with protection. Do we start after his name gets called, and they have to decide what to do?

I love playing loving interracial stories, and this is something that I'm super interested in exploring, so let's talk OOC about what we might want to do together and create something fun!

Lucy Reynolds was getting everything she wanted out of college. She'd been recruited to run track, a sport she loved, and the highest level. There had only been a few people from her small town back in Montana who'd left to go to college in her year. But Lucy's athletic gifts had let her write her own ticket, more or less.

Being away from home had given her freedom. She'd grown up a prim and proper church girl, always looking for ways to please her domineering parents and be the perfect daughter. In college, she'd realized what it felt like not to care. She started wearing makeup, styled her hair how she like, and (most transgressively) started getting tattoos. The art on her body was her pride and joy. Her main piece was a flowing vine that wrapped up one of her legs. It reached from the back of her knee to just under the waistband of her underwear, but was on full display on the track. She had some other small pieces, and they were a visual reminder of who she had become.

Lucy had also started experimenting with sex and drugs as soon as she'd gotten to school. She liked a drink or two at a party, and she'd smoke in a group, but she'd decided the lifestyle wasn't for her. Boys though? That was another matter.

Lucy had always been forbidden to date, and she'd started trying as soon as she'd moved from home. There had been short hookups at first: she'd learned the ropes with a succession of men who didn't know what they had. By the end of her first year, she was ready for something more serious. That's when she'd met Zion.

Zion was the star of her university's football team, and the most famous athlete to walk the campus in years. He was a year older than Lucy, and already tagged as a future NFL prospect. They'd met at a party for athletes to celebrate the end of the year, and hooked up the first night. They'd been inseparable ever since.

As their first anniversary was coming up, they were more in love than ever. Lucy slept at Zion's apartment most nights, and reveled in being the star's girl. She knew the draft was coming, and there was a chance Zion was going off to another city and they'd have choices to make. But she was putting that off as long as she could.

***
Hi! Today I'm looking for a partner for a new story: Lucy is a college student who got out of her hometown and tough family on a track scholarship. She's become her own person, and left her conservative background in the dust. Now she's a sophomore, and coming up on a year dating the school's star football player, who's most likely NFL bound.

How we play this is super open! Do Lucy and Zion have a little accident in the bedroom a few months before the draft? They're fucking A LOT and maybe not that careful with protection. Do we start after his name gets called, and they have to decide what to do?

I love playing loving interracial stories, and this is something that I'm super interested in exploring, so let's talk OOC about what we might want to do together and create something fun!