Have been a submissive male ever since my years in high school. Always had a strong attraction to Women of authority, those who would raise their voice, or who would be in control. Into my late twenties and early thirties, I began to explore this side of me much closer. Having changed from vanilla porn to FemDom porn, I knew the kind of images or scenarios that I enjoyed the most. In my early thirties, I had really begun to explore orgasm denial and male chastity. When I was 32, I began to meet a few Dominant Women online, and enjoy submitting in real life. For the next 8-10 years, I had served as a houseboy, errand slave, shopping slave and chastity slave (submitting to around 4-5 Women during that time). Now in my very early 40s, I have continued to serve, mainly online Dommes. Not too long ago, I met Mistress Luna on an adult website, and could not be happier! She is young, cruel, demanding and beautiful. She had me in chastity a short time after meeting each other online (pink Vice Mini). The connection i feel with Her brings me so much pleasure, and I am trying so hard not to disappoint Her. Now, for the first time in my life, Mistress has me exploring sissification and feminization. Already wearing the pink cage, I will be replacing all of my boxer shorts with Women's panties. Mistress wants me to purchase a depilator this week to help reduce my need for shaving unwanted body hair. She currently has me on a once per month schedule for an orgasm. With a necessary cum tax to be paid each time by me. It should be quite a thrill exploring being sissified, having never experienced it before. Wearing panties every day, along with having my penis shrink over time and having smoother, softer skin is a good beginning to my transformation. I will keep this blog updated as often as I can. Today is day 11 in chastity, with my next scheduled orgasm set for May 3rd.
From what I read it seems you have a good mindset. Mistress Luna seems to have an eager student who desires to be sissfied and learn. I wish you well into your journey to become a sissy. I look forward to reading and seeing your progress. MistressS
I hope that you like it as well cos having to do it if you dont like it must be horrible and after a bit you get use to a lot of thingys that you prob think now is hard to do and take a long time but they gets quicker to do when you are doing them all the time.
Best Wishes for your transformation journey @njboyincb6000 ! It will surely take a while and there may be a few bumps along the way, but as you adjust, your will find those feminine feelings and softness oddly comforting and really enjoyable! Sounds like you are in the control of a Mistress who is experienced and who takes Her time. That makes the fun even better and more memorable.
Good luck on your journey. I'm sure there might be a few hiccups. But it sounds like you are in good hands. Enjoy the ride.
Thank you so much for the kind words and best wishes! It will hopefully be a fun journey. A little sad to see my masculinity go bye bye, but Mistress knows that this is what i an destined for. Depilator shopping online this Thursday night, and panty shopping in May.
Update April 18, 2020 Day 16 with no release. Was unlocked yesterday for a cleaning and shavimg, then returned to chastity immediately afterwards. Lock #559801 Still have an expected release date of May 3rd. Very excited. Ordered a pair of pink nipple clamps this week, as well as two "Future is Female" t-shirts in pink. Will be shopping online for a depilator this weekend.
Enjoy the journey. It may seem sad at first to give up being a man. But allowing yourself to express your inner femininity is fun and addictive.
It is exhilarating right now. Have been submissive for many years, but was never into being sissified. Now with everything in pink, and my hair removal, it definitely makes my skin curl up. Mistress Luna has done this to a few boys in the past, so definitely in good hands.
Not intended to be a slight on your journey. The leap from Femdom to sissification and feminisation is significant, although quite prevalent in porn. Have you an insight into her rationale to move you from a male submissive serving a Dominant Woman, to a male submissive in female clothing serving a Dominant Woman? And how do you feel about that?
Haven't really had an insight into Her reasoning for this new direction. It is something that was pronounced to me early on, and so far we are still in the early stages. Although I have not experienced this before (sissification), it does give me an adrenaline rush just thinking about the possibilities. Exposure for me is a huge turn-on. Mistress has shown a few of my pics to Her friends, and knowing that my chastity is a source of amusement to others, gets me very excited. Just thinking about the images of me in panties and stockings (eventually being presented to others) makes me very accepting of this (because of the exposure). And of course, as a male submissive, i should listen and obey instead of questioning any of Her decisions. So up til now, i am playing along and enjoying myself very much. She has a close friend that is also a Female Dominant. Her friend has told me that my Mistress has much experience turning men into sissies, so this must be something Mistress really enjoys. And if Mistress is happy then She will hopefully spend more time with me.
Your story is interesting, as I assume that your Mistress is not someone you are physically with (proximity) all of the time? I assume that this is predominantly still an online connection. Have i got this right? In essence, most online D/s connections are limited, financial domination being the exception with its proliferation. So was the move to feminisation more to do with finding something that could work for an online D/s, or were you already predisposed to this genre?
Yes, my relationship with Mistrress is 100% online, as we do not live within close proximity of each other. Although we have discussed potentially meeting at some time in the future, as of now, it is online only. I have had online Keyholders many times in the past, and chastity was the main (and only) dynamic for each one of those relationships. Mistress' decision to initiate sissification was not really as a result of distance. It appears that Mistress will attempt to sissify the majority of men who serve Her. So it is something that i was destined for. If this will increase my level of submission to Her, then it will be even more enjoyable. However, being new to sissification, it is a little bit scary to see how much my personality will change after going through the process. Will I enjoy it a little bit too much? Will I begin having different fantasies? Will my friends detect a change in me? These are all questions I'm eager to find the answer to.
Or will you find it's not for you! But I detect obedience is key to you, so anything your Mistress commands must be obeyed regardless?
Sorry for disappearing recently. Have been battling some health issues (not virus related), and now beginning to get back to normal life. Thankfully, Mistress put me back into chastity on Tuesday. So been chaste now for a few days, and starting to realize how much I missed it. No release date has been set.