Back when I was 22/23, I had just graduated college and found a job working at a retail store to pay bills until I could land a job related to my degree. Still living at home and basically living the single bachelor life.

The staff at this store was pretty run of the mill. Some teenagers working summer shifts, some older people working a job to get some supplemental income while their spouse brought in better money, and one woman in her early 30's that was "working for fun" as she put it. I couldn't comprehend that at all, but she was pretty chill and we became friendly pretty quickly.

She was pretty average looking in work attire, but one day she came in wearing a sun dress and heels to grab her paycheck, and that was the talk of the store for a week. Like, holy crap did she look great in clothing that accentuated her body. She had really great curves, average size breasts but the dress made them POP out (maybe wearing a push up bra?) but holy crap did she turn heads by customers, workers, and even the managers.

Anyways, we really hit it off after working together for a few months. Had common schedules - mostly weekdays from open to about 4pm - so we worked together quite a bit. We shared a lot of conversations and had fun while working. It was great!

Anyways, as time went on, we started being a little more open. She would complain about a bad date, I would complain about a girl on Tinder ghosting me, we understood each other's frustrations.

One day, while talking, she asked me why I used Tinder instead of a more "modest" dating app, and I straight up told her I just wanted to have fun right now. She bluntly asked me if I wanted to have fun with her, and we kinda had that tense moment where we were standing inches from each other, matching breathing, and trying not to kiss each other at work. It was intoxicating and I had a huge smile the rest of the day. She could tell that I was excited.

We already had each other's numbers and aside from sending each other memes, we were now pretty much sexting back and forth. Teasing photos, planning a day to hang out, etc.

Later that week she sent me a text saying "Come over to my apartment around 4pm on Thurs, you know why ;)" and I literally could not wait to swing over to have some fun. It had been over a week since I had cum and I was very eager to say the least.

By the time Thursday rolls around, I'm all showered up and heading over to her place. I text her "I hope you're wearing the dress and heels you wore to pick up your paycheck that last time" to get a response "I can wear the heels".

When I arrive, she's wearing them, and side note I have a huge heel fetish, I love women in heels. She's a few inches taller than me in them and she guides me over to the couch and we have a pretty awkward first time hooking up. One thing to note though, I was adamant on giving her ALOT of oral. Pretty sure that was my saving grace for our hookup. I've got a pretty nice cock, but I was still pretty awkward with it and we had a few giggling fits because of my awkwardness.

After a while, we got comfortable with each other and stared having some real fun. She would do adventurous things like tie my hands to her bed or tie me to a chair and tease me. I would also get booty calls to come over and give her my tongue, and after doing that a few times she once had me come over to take care of her, then dismissed me to head home. I asked about my orgasm, and she said "Nah not today, tonight is about me". I had a rock hard erection from those words and I'm pretty sure she noticed.

A couple days later I'm coming over to hang out and smoke some weed and chill, and she asks me how I liked being used and sent home. I was honest - it was hot as fuck and really enjoyed it, although I masturbated like crazy when I got home that night.

She apparently didn't like that and told me I should ask for permission to cum. I, being horny as fuck, eagerly agreed. She asked if I liked her being in charge and I think we both realized that a new dynamic was emerging from our situation.

A few more times she would call me over to just take care of her and was sent home, or told that she was going to head to sleep and I was welcome to stay the night and she MIGHT be generous in the morning if I was lucky. This was turning into something really really fun for me.

Further down the road, she is now sitting on my face, tying me to the bed, and pushing her assertiveness one me, demanding foot rubs, etc. I'm also obsessively researching things online related to femdom, such as orgasm control, chastity play, feminization, etc. And I just forward these things to her and she asks at each step if I want to try those things. I sure do! She is just as eager as I am to go down this rabbit hole.

I ordered a chastity cage, some panties, and an anal plug. After some fiddling with them, I was able to comfortable wear all three. So I wore them over to see her for us hanging out. I tell her I ordered some fun things and wanted her to discover them. She takes lead, brings me to the bedroom, and lays me down. Unbuttoning my pants she first sees the panties. "ooooh someone wants to be pretty today". As she gets to the cage, she asks if I wanted her to keep me locked the whole day - I eagerly agree. And then I tell her about the plug. She is insanely turned on at this point and wants my tongue, so she sits on my face and rides me to orgasm. I've never been so turned on before while caged/locked up, in panties, and plugged. After some squirming around of my own,I actually came in the cage before she could orgasm a third time, and she gets off me, scoops up the cum, and tells me to open wide. She left me locked in that cage for the day, demanding that I hand over the keys so I don't "misbehave". I was allowed out when heading home.

Something switched that day. it sparked a new sexual obsession that has pushed me further and further down the rabbit hole in being submissive and exploring these kinks. We kept extending chastity time until I was basically going a week without being let out, only to have her ruin an orgasm and lock me back up after cleaning up.

As time went on, we went a bit further with me having a rather large wardrobe of feminine clothing and lingerie (heels too!), I've become VERY into anal. We also explored me worshipping her feet, which I learned is something I am VERY into!

After some time, she decided she was moving out west and I got a job in a city a few hours away. We still occasionally send each other memes and whatnot, but last I heard she was dating someone, and I wanted to respect that.

Once in a great while, she sends me a picture of her feet at the beach or at the pool with a "shhh" emoji. I miss those days.

Should any women find this interesting, reach out!