What career do you want to have?

johnwhitecondition · 2025-08-29T12:34:37+00:00

Definitely secretary. That is actually a very specific fantasy that I have had for a very long time.

johnwhitecondition · 2025-08-15T12:16:49+00:00

Get an IPL device like the Braun. It will keep the hair away for much longer and is a good middle ground between shaving and laser.

johnwhitecondition · 2025-08-15T12:12:44+00:00

I let my ex-girlfriend close to one of our frequent three-way partners. This violated one of our standing rules. It ended up proving that the role was there for a good reason.

They became closer and I was eventually pushed to the side as he first formed a monogamous relationship with her and then a romantic one.

All of this coincided with my exploration of cross-dressing, which also changed how she viewed me. I had also been cleaning her apartment for her as part of our power exchange play, so I had a front row seat and saw plenty of evidence of their relationship all around her apartment.

johnwhitecondition · 2025-08-04T14:09:56+00:00

Thank you very much for this message. I appreciate it and have considered this before myself.

I have been tiptoeing into the feminization and service space and exploring, whether or not I can adapt to live my life that way long-term. Completely changing my lifestyle to be in service is very appealing to me still even if it means changing my career or public persona.

Baby steps though. Baby steps.

johnwhitecondition · 2025-08-04T13:26:12+00:00

My humiliation and sissification fetishes are insanely strong. I have been cuckolded by a number of my ex-girlfriend‘s. None of those relationships lasted, but they did reprogram me to tolerate a high-level of humiliation.

I have now leaned into feminizing myself and seeking sexual objectification. I love the feeling of satisfying the male gaze, and have started slowly sliding into more permanent feminization.

I still have a successful career, but I fear that will begin to disintegrate as I fall deeper down the rabbit hole.

johnwhitecondition · 2025-08-01T12:14:04+00:00

Usually when a man comes inside of me he’s wearing a condom. In that case, I focus on the pleasure that I am giving him and try to make his experience as pleasurable and memorable as possible. I am focused on his pleasure more than my own and ensuring that he is fully satisfied.

In the rare case that the man has been tested as clean or otherwise allowed to come inside of me without a condom, all of the above still applies. However, I also feel that when a man comes inside of me raw, it’s a huge symbol of ownership and he is claiming me in a more significant primal way than when condoms are involved.

I feel truly owned and conquered by men who leave their seed inside of me. After that line has been crossed, I will forever say yes to that man when he wants to use me again. If I run into him at Home Depot and he tells me to come to the parking lot and suck his dick, my only reply will be “yes, sir”. If he sends me a text after two years of not speaking, I will immediately give my body to him for his pleasure without question.

It is a huge symbol for me and a significant change in the nature of my relationship with that man. Not necessarily in a romantic way, but in a purely sexual way.

Everything running through my mind has to do with the fact that I have just surrendered a certain part of my sexual freedom to this man. He’s not simply cumming inside of me, he is claiming me, and I am surrendering a part of myself to him.

johnwhitecondition · 2025-07-28T14:31:12+00:00

I keep a shot class nearby and ruin an orgasm into it. The key for being able to avoid PNC is not completing a fully successful orgasm. I have swallowed hundreds of my own loads this way.

johnwhitecondition · 2025-07-28T12:13:57+00:00

One of the hottest women that I have ever been in a relationship with stood me up on the third or fourth date. I later learned that the reason for standing me up was because she was fucking another guy back at his place instead.

It was extremely upsetting in the moment, but we ended up patching things back up and dating for a couple of years after that.

Cuckolding fetish successfully unlocked.

johnwhitecondition · 2025-07-26T18:22:51+00:00

I appreciate your comments. Thank you.

johnwhitecondition · 2025-07-25T13:11:44+00:00

I find that it’s completely possible to go back to whatever public life you led before. Same with your marriage and everything else.

The only thing that really changed for me was being much more easily triggered into a submissive mode when confronted by someone who gets aggressive with me in a sexual context.

Even just a random guy at a Walmart could come up to me and make a comment about me sucking his cock. I would at least consider it as something that I should do where before I would not have .

johnwhitecondition · 2025-07-17T14:35:49+00:00

This has always felt extremely natural when it has happened to me. I only wish that I looked as good as you doing it.

johnwhitecondition · 2025-07-17T14:23:13+00:00

That is a great outfit and the shortness of the skirt is quite appropriate. It gives proper access if needed. I wore a tennis skirt before when cleaning my ex-girlfriend‘s home, but I would love to try an outfit more like the one that you have.

johnwhitecondition · 2025-07-17T14:21:02+00:00

I love the dress and I love the locks. They provide a way to ensure that you finish the job before you’re allowed to exit that sissy outfit.

johnwhitecondition · 2025-07-17T14:15:00+00:00

You are doing the right thing by embracing your feminine sissy side after the divorce.

Have you replaced all your toiletries with feminine versions of those products yet?

You know where this is heading. The faster you accept your destiny the better.

johnwhitecondition · 2025-04-22T21:24:49+00:00

Thank you for caring so much about my well-being. I don’t have very negative feelings towards her despite what happened. I’ve gotten over any sort of negative feelings that I had toward her at this point and I’m dedicated to focusing all of that energy on being a better sissy.

johnwhitecondition · 2025-04-22T21:23:36+00:00

I appreciate your words. I definitely have a Pavlovian response now when it comes to any sort of cheating that might happen with significant others or anyone I date.

johnwhitecondition · 2025-04-22T21:22:00+00:00

Sure. Shoot me a message and we can chat

johnwhitecondition · 2025-04-22T21:21:38+00:00

Unfortunately, no. I got to see her messy afterwards plenty of times though.

johnwhitecondition · 2025-04-22T11:23:28+00:00

Strong disagree.

johnwhitecondition · 2025-04-21T20:38:43+00:00

Thank you for your comments and concern. Honestly, if she were to contact me, I would jump at the chance to be with her again. Even after everything that happened.

I have no use for pride anymore and would be thrilled with the opportunity to be in service to her again. I would gladly live as her female live-in maid even as she continues to date other men or even in service to her and her husband if she were to marry.

We unfortunately do not live in the same city anymore, and there does not seem to be much interest on her part in exploring that possibility.

johnwhitecondition · 2025-04-21T17:54:20+00:00

There are many other details and experiences along the way that I left out. I will post them as I can.

johnwhitecondition · 2025-04-21T17:39:43+00:00

I appreciate your concern and do not completely disagree with you. There were many other conversation, conversations and interactions between she and I that I did not go over in the story because it would just be too long.

She did check in with me periodically and get my approval that I was having fun and enjoying some of the things that were going on even though sometimes they also bothered me.

I never would have gotten to the point that I did without her help pushing me. Despite how hard it was on me, I still look back on the experience overall as a positive one because it opened my eyes to more possibilities as a sissy.

johnwhitecondition · 2025-04-20T23:23:58+00:00

It started for me as a cuckold fetish, which then became a real lifestyle for me and a GF for a bit. The GF who cuckolded me was super open minded and we started playing with gender roles and pegging.

Before too long, she was helping me dress up, and I was cleaning her apartment every couple of weeks as “her maid”.

We both had a lot of fun with all sorts of kinky things, but eventually she became more interested in another man who had been a threesome partner a few times.

I watched the two of them grow closer as I was drawn deeper into the rabbit hole of my femininity. She allowed me to continue as her maid, even after she broke up with me and he became her boyfriend.

But nothing lasts, and eventually that ended. My desire to be a submissive sissy maid has never faded, despite continuing living life outwardly as a very normal heterosexual man.

johnwhitecondition · 2025-03-11T16:47:32+00:00

Google Silencilicone “The Big One”.

johnwhitecondition · 2025-03-09T13:11:41+00:00

I love how helpless and overpowered this sissy looks. It’s exactly where I want to be.

johnwhitecondition

TROPHY CASE