In early 2018 I was looking for a change. Sex with hookers was getting old. Sure, the girls were hot, and their skills considerable Some were true blowjob artists. But it always felt rushed. The clock was ticking, and there was no opportunity to get to know someone.

Of course it felt completely fake. Amazing how many experienced women would scream with passion, claim that I was their best lover ever, that they had never cum like that with others. Were there really men who believed this bullshit? I guess so or they wouldn’t have done it.

Looking for something different, I checked out Seeking Arrangement. By far the largest sugar-daddy site, SA seemed to offer the possibility of actually getting to know the girl, having less rushed sex and all at what I expected to be a more reasonable price point.

It didn’t quite work out that way. You have to screen through a huge amount of profiles to find a few that interested you. If I expected to deal with less mercenary women than the full professionals, I quickly learned otherwise. What I thought was a generous stipend did not pass muster with the hottest girls on the site.

Back then, before Seeking Arrangement got paranoid, you could have pretty clear discussions about money expectations. Nothing hinting at “pay for play,” that sounded too much like outright hooking. The site barred any discussion of sexual acts and banned guys for exploring in their messages how far a girl would be willing to go. But you could discuss what sort of monthly “allowance” you were willing to pay.

Jasmin’s ad was hot. It had several very revealing pictures of a slim young woman with legs for miles – and one picture of some S&M toys like handcuffs and a paddle. Her short profile clearly expressed her interest in “kink” and stated explicitly that she was “very submissive.”

Exactly what I was looking for! After a few messages back and forth, we agreed to meet at a local coffee shop.

I liked what I saw. Jasmin was on the short side, probably 5 ft 3 or 5 ft 4. She had kick-ass tattoos, along one shoulder and on her chest above her nicely-displayed B cups. Pierced tongue, but fortunately no piercings of her nose or eyelids.

Jasmin carried off the bad girl vibe. Even though it was a little cold out she was wearing short shorts that showed off her beautiful copper-shaded long legs to perfection. It turns out that she’s a physical fitness fanatic into working out five times a week, and it shows.

Jasmin and I made small talk for a while. We chatted about experiences on Seeking Arrangement, the number of assholes who had stood her up, the women who had ripped me off. Jasmin had just left her job as a retail manager and was looking for something to help pay the rent. She asked what my kink experience was and I filled her in, that it was mostly fantasies aside from some long-ago experiences with S&M hookers. Then it was her turn to describe how she got into the scene, what she had done, what she liked. She had me drooling.

The Making of a Masochist

Jasmin came from a conservative immigrant home. Her parents were devout churchgoers and expected her to be a “good girl.” They dragged Jasmin with them to church. Jasmin didn’t like it but had little choice but to go along – until she turned twelve. Then, no matter how much they threatened her, Jasmin refused to go to church. As she got a little older, she developed a taste for more revealing clothes than her parents wanted her to wear.

Jasmin knew that she had a high sex drive. She also discovered that she had a very high pain threshold and “crossed wires” - things that hurt “caused me a tingle down below.”

Once she turned sixteen, she became an ardent masturbator. She discovered internet porn shortly afterwards. Pictures of women being treated badly appealed to her most, although she couldn’t figure out why. After watching some S&M videos on the web, Jasmin began to incorporate pain into her masturbating. Using clothespins on her breasts, sticking large objects in her pussy, hitting herself with the bristles-end of her hairbrush – all those helped get her off. She fantasized about painful and humiliating sex – being ordered around by a strong master, kept as a slavegirl, passed around as a “party favour” among multiple guys. As she discovered BDSM websites her fantasies got more specific. She imagined herself being tied up, spanked and whipped.

Despite her new taste for more revealing clothes that showed off her body, Jasmin still went along with “being a good girl” to keep her parents off her back. She got adept at living in two worlds: a good girl at home and school, and an adventurous explorer outside.

Jasmin didn’t go on formal dates – her parents had made it clear that “good girls don’t date until they’re eighteen.” So she took to meeting boys secretly.

High school boys were clumsy and didn’t go very far. The logistics of finding a place to make out were challenging. Jasmin found herself the subject of fumbling explorations behind the schoolyard, in deserted buildings in the neighbourhood and in the occasional basement. She was too shy to let the boys know what it took to get her off. Not that they would have taken instruction very well, in any case. Losing her virginity at the age of seventeen was “nicely painful” but the guy came so quickly that Jasmin didn’t enjoy herself that much. She blew that boy off immediately afterwards.

I interrupted Jasmin’s tale to ask if she was ever into cutting herself or self-harm. “Fuck, no! Nothing sexy about that.” Jasmin was not your meek masochist. She was a strong woman who knew what she wanted. And what she wanted was painful sex.

After graduating high school Jasmin wasn’t prepared to continue her studies, despite her parents’ urging. She was certainly smart enough for university but had no idea what she wanted to study. And she was anxious to establish some independence. She went to work in a mall downtown. The retail job paid minimum wage but she was still living at home, saving up to get her own place – or more realistically, to get a room in an apartment shared with several other struggling young people.

In her daily life Jasmin developed into a direct, fearless woman who wouldn’t take any shit from anyone. At work she was quickly promoted to assistant manager of the store. She said that she was tough but fair. She got along well with her employees even though she didn’t hesitate to call them out if they were not working very hard.

At the gym where she worked out after her shift every day, Jasmin was frequently hit on by guys working out there. She would usually blow them off.  “I’m working out hard, I’m sweating a ton, really concentrating on my form with the weights. So why would these no-neck idiots think I would be interested in them?”

One guy at the gym was different. Hank was a little older, in his mid-twenties. Jasmin thought he was hot. He was a big guy, six foot two, towering over Jasmin’s petite frame. His body reflected the years he had spent in the gym. He was toned but not excessively like some of the steroid-using body builders at the gym. “Great six-pack, rock-hard pecs. And a sexy, rather cruel face.”

Hank was smart or lucky enough to meet her as both were leaving the gym. Now that Jasmin had a good buzz on from working out and had cleaned herself up, she was more amenable to his approach. Especially because Jasmin had noticed him working out and thought he was hot.

They went to a nearby bar for a drink. Hank was easy-going, and it was pleasant exchanging life stories. It was clear that he was no genius, and didn’t have a very wide vocabulary. “But I wasn’t looking for someone to have interesting conversations.”

You’ve heard about gaydar – gay people’s ability to sense others who share their orientation. Jasmin has kink-dar. She can sense when someone is interested in the BDSM or kink world. And Jasmin sensed something about Hank that got her even more interested.

Hank worked as a long-distance trucker. He had a fair amount of cash and his own apartment. On their second date, after a mediocre movie, they landed back at Hank’s place.

They started off making out and both quickly got naked. “Pretty decent vanilla sex” followed. Hank responded nicely to Jasmin’s urgings to go harder, be rougher. “Squeeze my nipples!” His strong fingers did just that, really hard – just the way Jasmin liked it.

It turned out that Jasmin’s kink-dar was spot on. Hank had some experience in the world of BDSM and turned out to be a good tutor. He coaxed Jasmin along as they graduated from somewhat rough sex to hair pulling, face slaps, and simple spankings. Then they moved on to light bondage and introduced toys like handcuffs, blindfolds and paddles.

Truth be told, Jasmin didn’t need much coaxing. She found that she was turned on when she was in pain. It was the combination of sex with pain that really made her stay on the brink of climax for a long time, and then cum explosively. Bondage on its own didn’t do much for her. When combined with pain, it was dynamite.

Hank was a stud. He could fuck her hard for thirty minutes, cum, and then go again. That hard body could really pile-drive Jasmin into the bed. Jasmin could go for hours. She loved fucking until her pussy was rubbed raw – that brought out the added dimension of pain that she craved.

Hank respected her boundary about no anal sex except for the occasional finger. Aside from that, she didn’t have many boundaries. She was willing to try anything more than once.

Hank brought out Jasmin’s inner slut. He liked to keep Jasmin naked in his apartment while he remained fully clothed. That was particularly degrading. Hank would play video games and ignore her for a while, or use her as a footrest. Occasionally he would reach out to slap her breast, stroke her pussy, unexpectedly shove a finger up her ass. Jasmin loved not knowing what was to come next, and being treated like a sexual object. And she loved degrading talk. It got her hot to be called a bitch, a slut, a cum-bucket. Hank didn’t hold back. His vocabulary was rather limited but the message was clear – particularly as it was often accompanied with slaps to her face and breasts, pinches to her butt, a few hard spanks.

The relationship with Hank went on for almost a year. Jasmin spent a lot of time at his apartment but would always go back home to the suburbs and her parents to sleep. She wasn’t prepared to have them discover that she was in a relationship and made up bullshit excuses about spending time with girlfriends. In fact Hank was tying her up, beating her butt and screwing her brains out.

The End of Hank

Jasmin found that she and Hank were falling into a rut. He lacked the initiative to change things up and keep her on edge. Jasmin was getting tired of always being the one to come up with the suggestions. “It’s not that degrading if I have to suggest it myself.” It didn’t help that Hank wasn’t very smart, they didn’t have much to talk about when they weren’t fucking.

The student quickly surpassed her teacher. Jasmin wanted to continue pushing their boundaries and try new things, and Hank resisted. Jasmin wanted to try threesomes. She thought that serving two masters would be hot. More abuse to go around, and she could be spit-roasted: fucked in her mouth and pussy at the same time. When Hank resisted, she suggested that they do a threesome with another girl. Jasmin had enjoyed a few interesting lesbian experiences but they always were plain vanilla, without kink. Hank wasn’t up for that, either.

Public display and humiliation of his slave didn’t seem to be Hank’s thing. He reluctantly accompanied Jasmin to a local sex club on a BDSM-themed night. Jasmin wore leather: a halter top that revealed more of her breasts than it covered, leather short shorts. And of course a leather collar studded with metal. Hank wasn’t into dressing up and just came in a pair of jeans and a T-shirt.

Jasmin had brought along a leather leash to attach to her slave collar. She wanted Hank to lead her around the club on all fours to advertise her subservience. He wouldn’t do that. Even though several interesting dominants, both male and female, approached Jasmin and complimented her on her outfit, Hank’s forbidding presence didn’t allow anything to develop. At Hank’s urging they left the sex club early, before things got more interesting. Jasmin was hot after the public display and was eager to fuck. But Hank said that he was leaving on a long trip early the next morning, and wouldn’t play.

For someone experienced in BDSM, Hank really wasn’t reading Jasmin’s signs very well. He was becoming romantic “like a sap. He even started to talk about moving in together, maybe even getting married!” Jasmin had visions of her immigrant parents’ stifling life in the suburbs. That wasn’t for her. She blew Hank off shortly afterwards.