What’s the hardest thing you’ve done for a man out of obedience?

So basically, I agreed to it because he had his birthday coming up. I asked him what his favorite present would be - and that was his answer. He gave a budget to buy clothes, make-up etc with, and he would buy some himself for me as well. The deal was that I would buy four full outfits - two for during the day (ie that I could potentially even go outside in) and two for 'in the boudoir'. He would buy two of each as well. I would keep my choices a surprise from him, and he from me until it was time to put them on. I remember him putting four of those 'bags' you would put a suit or a dress in (not sure what they're called) into the car.

When we got settled in at the airbnb (large, spacious apartment in a small medieval city in the middle of the country), he asked me to choose and put on the first 'everyday' outfit. I knew he like costumes, and I thought it would be fun to role play a little, so I had chosen a French maid outfit. Not too racy, just a shiny black dress and little white apron. Black long stockings and shiny pumps (see picture for the shoes). This is where the bell that I mentioned came in, I had thought to bring it as a joke so that he could ring it whenever he needed my 'maid service'. I could have expected that he would only use it for one purpose.... So basically within an hour I was on my knees in front of him while he sat on the couch, watched TV and drank beer.

Not everything from that week was that exciting, but the fourth day - his actual birthday - was. Both picks (everyday outfit and boudoir outfit) were obviously his for the day. Now we had a slight clash of styles, I liked to think of myself as 'lady in the streets, whore in the sheets' so mostly elegant dresses coupled with racy lingerie. He liked me to be a little bit slutty, even trashy/bimbo-ish. So the everyday outfit was a short leopard-print dress, white hold-up overknee stockings and bright pink platform heels. Obviously platinum blonde wig, pink eyeshadow and lips and hoop earrings. We celebrated the big day with a glass of sparkling wine and cake, and he gave me the 'bimbo' treatment (slapping my ass, asking me to bend over to pick up stuff, etc. He took a shower, then immediately rang the bell so that I could 'service' him before he got dressed.

Although it was only around midday, he then already asked me to go back to the bedroom and put on the *other* outfit he had laid out. So generally, boudoir outfits (mine and his) consisted of some nice knickers and bras, elegant stockings, maybe a camisole or negligee or a bustier/body. But when I opened this one, it was.... different. The outfit consisted of a) stiletto heeled pink leather-look boots, b) a pink bob wig, c) a choker with the word 'bimbo' written on it and d) a butt plug with pink diamond end. I looked around the bag multiple times, but that was all that was there. And the bell was already going off...

I strut into the living room awkwardly in all my nakedness - high heels and buttplug was then still a new combination - where he was sitting on the couch. To my horror, I noticed the curtains were wide open, so anyone outside (we were on the first floor, but still...) could get a good look at what was going on. I moved to close them, but he stopped me. He then took out a 1,5m chain, clicked it around the chocker with a tiny lock, and fastened the other end to the radiator. So I was on my hands and knees, naked but for the leather pink boots and plugged up. He wanted me to beg for it before I would be released. So before long I positioned myself to show my plugged 'pussy' into his view and wiggled seductively and started asking him to come and take my hole. After about five minutes of me wiggling and begging for cock, he finally came over, pulled out the plug and replaced it with his member. Thankfully, we were 'down low' so not visible from outside, but I did have to awkwardly shuffle back past the window with his cum leaking out of me...

/r/sissyology Thread Parent