r/TrueSimpStories

A few months ago I started snapping this girl every day. We weren’t actually having conversations or anything, we just had one of those Snapchat streak-type things where we’d send snaps back and forth daily. Even though we didn’t really talk, I always thought she was attractive.

She’d always post herself wearing really nice outfits and honestly looked like a businesswoman. I don’t know exactly why, but I got the feeling she might be into findom. It was completely random and I had no real reason to think it, but the thought stuck in my head for months.

Eventually my curiosity got the better of me. Instead of asking from my main Snapchat account, I made a different account and added her on there. After a bit of small talk I just asked her straight up if she was into findom.

To my surprise she said yes.

She told me she’d done it before and used to be pretty popular doing it on Twitter. I honestly couldn’t believe my random guess had actually been right. After that I started asking questions about it and eventually we moved the conversation over to Telegram.

After talking for a while I told her that we actually knew each other in real life and asked if she’d ever be open to that kind of dynamic with someone she knew. At first she said no. Then she basically told me that she wasn’t going to continue talking about it unless I told her who I really was.

I was nervous as hell. I kept putting it off because I thought she would either block me or think I was weird. After going back and forth in my head for days, I finally told her who I was last week.

Her reaction was nothing like I expected.

She wasn’t angry and she didn’t stop talking to me. Instead she said she’d be willing to meet me and let me serve her. Since then I’ve sent her a little bit of money and we’ve been talking more.

The crazy part is that we’re actually supposed to be meeting tomorrow. Right now I’m excited but also pretty nervous because this whole thing started from a completely random suspicion I had while sending daily Snapchat streaks. I never thought asking one question from an anonymous account would end up leading to an actual meet-up.

Kinda scared to see her I’m thinking of wearing chastity and panties underneath my clothes.

I am just starting out simping for a woman I am crushing on. We've had several talks now and we chat daily on social media and she is planning our first "date." We've set some ground rules, including her not ever being sexual with me in any way and never seeing her naked. I asked her if she was willing to do things to make me want those things with her, she told me "Of, course. That's the tease part."

Our conversation finally came around to payment. We decided that I would pay a monthly fee to her, which would cover all our interactions, which she will be deciding on, directing, and initiating.

We discussed my income and budget and we decided on an amount that would hurt a little bit, but not cause me financial problems or be unsustainable.

One of the things I hadn't counted on was how much it would affect me. Now, every financial decision I make makes me think of her and how I am needing to sacrifice on small things to make sure I can afford her. No more Starbucks, no more eating out when I can make something at home. Cutting back on frivolous purchases.

I am already wondering how it is going to feel each month when I hand my fee over to her and spend the rest of the month having to be careful with every choice I make, so I can be sure to make ends meet and keep Princess happy.

This is my first post and English isn’t my first language therefore ignore any errors.

A few months ago I met this girl at a bar and we hit it off pretty good and started to meet again couple of times. I never had a Girlfriend but was still good at flirting and generally very popular. If you would have asked her if I was giving beta vibes she would have never said yes. Anyways we fell in love, started dating and she took my virginity.

After a while I started to introduce her to my foot Fetish and we started to play around with it while having sex (she is very vanilla when its about Femdom and Co but has tried other stuff with other guys before me)

One day I started to ask her if she would like to get her nails done and she said “only if you pay for them” and I obviously very happy to hear that told her of course and booked an appointment for her to get a manicure and pedicure. I went with her to the shop and waited for 90 minutes. She got some french tips and when it came to paying I went to the register and the lady behind it told me even though I paid in advance the fact that my girl wanted french tips would cost me 15$ extra. So in total around 120$

This week we went to a sex shop and got a chastity cage for me. We went home and I had to put it on (and are currently writing while wearing it) she already released me after a day but told me to put it back on for another two days. Right now she is swimming with a couple of her male friends while I sit at home, locked and writing. Tomorrow she is going to get a pedicure in a close town with some girl friends of hers and she already told me that I will pay for it.

I talked with her about cuckolding and all that and she said maybe in the future but for now she doesn’t want to because she loves me to much and thats what was always important to me. A girl that does this kind of things with me/ to me but still loves me and cares for me. I also love her so much and will always love her.

If you want you can dm me and ask anything I might update if you want.

So I was an idiot and I continued treating my ex-colleague to their monthly coffee tribute even after we had an argument and a huge falling out. I had set up a small monthly scheduled payment from my account to them so they can top up their Starbucks card and I really considered stopping after our argument but I kept it going as £15 wasn’t a big enough problem but hoped it’d make them happy and tbh gave me a small thrill seeing it automatically taken from me and knowing it’s going to her for an occasional treat.

This morning they messaged me unexpectedly informing me that our arrangement is no longer satisfactory for her and “adjusting for inflation” I would need to adjust my bank details and start sending £20.

This matter of face and brutally blunt diktat made me feel so immediately horny and I couldn’t help but navigate to my bank app and begin to edit the payment details…

I’m kinda scared this is a slippery slope and she’s just testing the waters to see what I’d do but right this moment it feels so good to have her toy with me after so long I’m kind of excited to find out.

In October of 2018 I was walking my dog in a local park when I bumped into a girl. Her dog and my dog got along well and she was very extroverted, so we started talking as our dogs ran around together. To my surprise, when I told her I was going home she suggested that we exchange numbers so that we can go on dog walks together. Being a 24 year old kiss-less virgin at the time who had become accustomed to zero attention from women and hadn't even had a female friend since I was a really little kid, I was of course very excited at the prospect of getting to hang out with a girl my age. I walked home feeling like I was on top of the world. Maybe I was finally getting somewhere. Maybe I would even lose my virginity.

This is how Tamara entered my life. Starting from that October we would go on dog walks together in London pretty regularly. I was a loser who didn't have much going on in life aside from a part time job at a supermarket and was enrolled at a college which I rarely attended.

I got to know her during these walks we went on. She had a boyfriend, who she openly told me was shit at sex and didn't know where her clit was. She would call him a pussy and was pushing for an open relationship with him. She had a sugar daddy that her BF didn't know about who would buy her things and invite her to his holiday home in Brighton. She was an ex-pole dancer. She'd had sex with tons of guys, but seemed pretty uninterested in doing it with her boyfriend, lol. She made fun of him for "only" being with one girl before her, and claimed that girl was ugly anyway. One quote from Tamara that has stuck in my head till this day is "if I want to fuck someone, i'm going to fuck them." She was bisexual and had a girlfriend in the past. She even had one funny story where she tried to sell some shoes online and some guy had messaged her asking to buy pics of her feet. Of course, during these chats I would make up stories of past girlfriends and sexual experiences.

Our walks went on until around the winter of 2019. Nothing happened between us for them to stop, but the frequency of our walks together kinda just died down from multiple times a week to maybe once every few weeks to eventually nothing. We just stopped texting each other to see if the other was up for going for a walk. It just ended like that, we drifted apart. Her house, where she lived with her parents and sisters, was actually very close to mine, but I never randomly ran into her in the park again like I did that day in October of 2018. Eventually a few years passed and we hadn't spoken at all.

For some reason in 2025 I got the idea to send her a message. I pretended to be some guy from a club she used to work at ( remember, I mentioned she was a former pole dancer) who was interested in buying some pictures of her feet. Two for £100. She responded asking which club it was as she had worked at a few and asked what my name was, and also teased me for thinking about her feet after all this time, lol. At this point, I parted with my original plan. I came clean and told her it was me, the guy who went on walks with her for about a year. I told her I originally lied because I was embarrassed. She remembered me, and my dogs name, and told me not to be embarrassed at all and that she doesn't judge. She said she was flattered and could definitely make it work for me, asking me what types of feet pics I like. This was the first time I had done anything like this, and I told her I would like them to have her soles and face in the shot if possible. She said she would do so when she had time over the weekend, and sure enough she did. She sent me her paypal info to pay her and Instead of two pics she sent me two ( very very short) vids of her face and feet. One in "the pose" and the other of her sitting on her sofa and sticking her leg out to show her bare foot. I thanked her a lot and then asked if she would ever be up for me paying her to rub her feet in my face. She said she would!

I haven't set it up with her yet, but as a 31 year old kissless virgin loser, I think it would be pretty cool if my first kiss was with the soles of her feet, right?

I've been doing photography for more than twenty years now and I've worked with hundreds of models. This last photo shoot was different. Something about the woman I was shooting triggered feelings that sent me back to my early day, the first time I was friendzoned and the first time I found myself as a simp.

The shoot went great and there was a nice connection, very professional. The only thing different than normal was that she referred to herself as a Princess. It was apt.

A few days pass and I send her the photos. All is going as normal. But that night I couldn't sleep and the next day, I sent her a text asking if she had any experience with Femdom. She said she had and asked me to be more specific and she would let me know if what I was asking about was within her "wheelhouse."

A few back and forths later and I had laid it on the line. I was looking for a Princess to friendzone me and make me her beta simp.

Long pause.

And then, "Oh, I can definitely do that!"

A few days later and an hour long phone conversation, we spelled out the details of our relationship. I'm paying her a monthly fee and she'll decide what happens from there.

I expected something like femdom sessions but she tells me there will be some of that of course, but the kind of humiliation I am describing really needs to be more public. We'll be meeting twice a month for our "dates." She will decide when and where. In the meantime, the texts continue as does the teasing.

I have no idea what is going to happen, but I shared a lot of my history as well as my most embarrassing secrets and fetishes, all of which she plans to use against me. There will never be any sexual contact between us, though she is very happy to make me want that and it is very likely she is going to be holding the keys to my chastity as well.

I am still waiting for her to set our first date, but I am absolutely squirming, waiting by the phone for her call or her text.