(22F) Just got with a sissy boyfriend and it's turning out to be one of the best decisions I have ever made.
I'm a pretty feminine straight girl and I've always been most attracted to more masculine men that can keep me safe, physically turn me on and take charge. The problem with those relationship dynamics though is that the woman typically ends up doing more favours for the man than vice versa because my submissive nature combined with their big egos makes them a bit selfish and view acts of service that aren't the classic "lead, provide and protect" as beneath them(and although have the physique and the hot dominant demeanour, are usually selfish in bed). It's frustrating for me because I can't stand simpy guys that put me on a pedestal and do everything for my approval so I never thought I'd be in an FLR. But despite that, I liked the idea of being served without it being from an intimate partner I'm supposed to have a normal sexual relationship with because it's way too much of a turn-off.
Last year I had a very upsetting breakup with a toxic boyfriend of over a year that I tolerated shitty behaviour from and did way too much for only to find out he was cheating on me with my close friend for months. I was completely disinterested in dating ever since then but still had needs to take care of. Which being freshly single left me with home-alone porn & bong nights with my vibrator.
I noticed an over-abundance of what was called "sissy" porn and intrigued, I checked some of it out. Much of it was solo-style porn(clearly directed at sex-starved single men) featuring lengthy-ish brain-rotting captions with stacked, dramatic short references to what I've learned is associated features to this sexual conduct like chastity cages, erection & orgasm denial, homosexuality feminine attire and anal. Much of it felt like dopamine pixel vomit that was sexually repulsive and made me cringe yet was simultaneously hilarious due to the sheer ridiculousness of the depictions. I couldn't help myself but keep exploring it a few particular nights and surprisingly ended up taking a liking to some of it that featured a big, strong masculine man dominating weak little twinks and those that involved women such as cucking and FLR/femdom depictions. I still found it very amusing but found myself getting off to the thought of having a whimpy little simp boyfriend that let's me fuck big burly hunks and potentially even watching him be fucked by them.
It quietly made it's way from my horny, THC-fuelled imagination to my resting, daily thoughts and I pondered what that would be like in real life. I know porn glorifies everything but the thought of having an obedient and humbled servant that will do everything I say and fill my life with leisure without expecting any sexual favours, acts of service or the typical affirmation of masculinity guys usually expect sounded great. I also knew that in this day and age, plenty of single men would tolerate being spoken down to, humiliated and sexually repressed just to have a young woman's attention & affection. So I was feeling somewhat optimistic.
Eventually when I was having cones at a friend's house, a guy 2 years younger that I'd met through her a few ties before and thought was sweet was there. As it does, after enough cones we were all being very open & honest about our dating lives and I still wasn't done with bad-mouthing my asshole ex. He was the only guy there with 4 stoned, giggling girls grilling him about what he's managed to get himself in to in the world of girls. He said that he's never managed to get more than a first date but would really like to have a relationship. My friend said deliberately said "Tell them about your femdom fantasy!" at the top of her lungs to embarrass him and we all absolutely lost it.
I was so glad that happened because I was dying to tell somebody about my own curiosities and I knew this was my opportunity. I ended up discussing it with him for a while and agreed that we would meet for breakfast that weekend.
I kind of felt pity for him because I knew I was not attracted to him at all and felt like I was taking advantage of his desperation but we're all adults and relationships are about compromise. I felt like if I was getting what I wanted and everything was agreed upon & consensual then I could let myself go to enjoy it. We discussed the dynamic and he said he would agree to being ordered around to serve my desires, be kept in a chastity cage I would keep the keys to and I had the final say in relationship matters. When the discussion moved to sex I said outright he would not be having any sex with me and that he would never get to see me naked which felt cruel but made him thinly smirk and widen his eyes so I realised part of him was hoping to hear that. He asked if I would get him to eat me out to which I said no to. I love the feeling of it but I have to be aroused to which I couldn't see happening with him.
At the end of it I discovered he was nice, passive, gentle and warm-hearted, just kind of spineless and timid. Which I thought was suitable for what we were getting in to. I told him he was able to come over to mine the next night to start exploring what our time together would look like and he agreed eagerly. So we agreed on a to-do list for his visit that would put his skills at serving me and handling emasculation to the test.
First was to go to the adult store to buy a French maid outfit, which I checked they had and choose a chastity cage. The worker approached us to ask if we needed any help so I took the opportunity to test his tolerance and loudly said "Oh I'm looking for a nice frilly maid outfit for my sissy-boy so he looks pretty while he cooks and cleans tonight! And for a nice little chastity cage to make sure he behaves!". He was gently grabbing at me trying to quieten me down as soon as I started but the worker just laughed with me while he nervously smiled and turned away. We left with a nice pink maid outfit that came with long white stockings and what was called a bird-cage steel cage that was 1.5 " long and dome shaped.
When we got home I told him to have a shower and to come out in his maid outfit and locked in the cage and hand me the key. He made us a stir-fry for dinner that we ate on the couch cuddled up together and damn he is a good cook. I then told him to clean up as I started hitting the bong. When he was done I told him to give me a foot massage and dayum he was good at that too.
I felt bad getting high and enjoying him slave away for me even though he seemed happy too but I let him smoke some cones and my intention was to send him home in an Uber still in the maid outfit for a laugh but we were so baked that I let get back in his clothes and sleep in bed with me.
He made us breakfast and we talked about what the foreseeable future of the relationship would look like since I had a great night and was getting really comfy with him and he was thrilled at everything that was happening. I told him if he wants to stay with me then he will only be unlocked if he needs to clean in there under my supervision but he would be locked and orgasm-free 24/7 outside of that. He was shocked and hesitant, tried to plea with me but I said he can take some time to think about if it's worth continuing seeing me, which I knew would get him to agree. We agreed next time he visited we would go get a mani-pedi and get our nails painted bright red and then go shopping for some heels in his size. He looked horrified for that but knew I meant business and understood he was prepared for humiliation and embarrassment.
He also asked if he would be involved in any way with the men I'll be seeing including if he can watch me fuck them which I gave him a maybe on. But we discussed his sexuality more and hinted he wouldn't mind "forced bi" which sounded really weird but he basically wanted to be ordered to give sexual favours to men which I connected with being forced to do other emasculating things he would quietly enjoy.
That was just over a week ago and I haven't been this happy in years! He's had a visit similar to the week prior last weekend, our friend circle knows about it(which they were very supportive, albeit amused about) and things are progressing very well. We are talking now about kinky play like ball-busting, internet and public humiliation and going to kink groups to meet willing male partners and show everyone what a good sissygirl I have.
What I love about this is that my pleasure and comfort is prioritized while all he expects in return is my attention and approval. Meanwhile I can get my sexual needs and masculine energy from any man I choose. I love seeing him tolerate having his male ego destroyed for my amusement, give unmatched subservience for my happiness, and knowing that over time he is enduring increasingly intense sexual frustration all because I'm enough of a prize. Really feels good.
I wanted to give some love to sissies around the world and please know that if you aspire to find a gal that's happy to be your Mistress, put yourself out there and you can get what you want! You might just show yourself and her a whole new world of fun. Anyway, sissies are the best!