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Little Miss Oakleigh – A love for gender play or for humiliation and exposure?

It seems to be still a taboo also for a lot of kinksters but the femboys and lingerie lovers are more and more visible on social media. They are coming more and more out of the closet. But there are different motivations to wear female cloths. Some like the gender play, others the humiliation and exposing. Let’s see why the porn actor James Oakleigh has decided to show himself in girly outfits.

Hi James. Some will be probably surprised to see you in fem cloths, but I know there are many who think that it looks real sexy. How does it come that you’ve started to buy female underwear?

I honestly can’t remember exactly when I noticed it, but I was scrolling through porn and kind of got sucked into the rabbit hole of the internet. I was watching one video of a fem boi playing with a bad dragon toy. I don’t know what exactly it was but I was kind of turned on by the silky smooth skin, cute thigh high socks and all the paraphernalia that goes with it.

At that point I admitted to myself it was hot, but never thought I could pull it off myself. And here we are, talking about pics of me in lingerie.

The emotions you get by seeing something on internet and trying it out by yourself can be totally different. How was it to wear the lingerie in real life? What kind of feelings have you had?

So the first time I tried it, was with some cheap and cheerful panties from somewhere online. I forget exactly where. I remember I had freshly trimmed/shaved body hair, so apart from the face stubble and slightly masculine/muscular physique it kind of worked as a fem look. Although I found it hot, I didn’t feel comfortable with it and was slightly disgusted with myself. Although I couldn’t help snap a few pics.

It took a while but a few days later I was talking with friends and kind of mentioned fem boi stuff, before I knew it I had shared the pictures with them, and they went down well. Some said it wasn’t for them, some found it hot, others revealed they were also into it. But I never got a negative response.

You’ve said that you didn’t feel comfortable … why did you continue and what has changed?

I tend to find it’s the same with some kinks I’ve found myself attracted to. Sometimes it just takes a while of working through things and realizing that what I’m into isn’t disgusting or filthy, but just a lesser known fetish I guess.

I find anything that’s not mainstream tends to disgust me a little before I find myself loving it.

The motivation for such kinks can be very various. Some like to wear lingerie to feel feminin, others love the humiliation they feel by wearing it and others just like the look. Which combination is it for you?

For me it’s a good mix of all of them. I don’t really ever feel feminine in a female sense, I am always a boy when I wear these things.

I think I am a mix of humiliation and aesthetics. I like to dress up and look all smooth and pretty with a chastity cage, serving real mean with my holes. There is something satisfying about being fucked, fisted and degraded in a fem boi outfit. It’s hard to explain, but I think that sums it up.

Can you tell us why you feel degraded by wearing fem cloths?

It’s definitely a submissive thing. I kind of get turned on by being turned into a fem boi, a regular guy being made to dress up in pretty lingerie and made to present for a real male or males pleasure.

I remember visiting a friend who knows I love cars, he let me drive a brand new BMW M2 and then took me out for dinner… But the condition was I had to wear pretty panties and stockings with a pink chastity cage underneath.

The sensation and feelings of driving quite a butch and powerful car, acting very manly yet looking like a pretty fem boi underneath was quite arousing. That and having to sit in a restaurant wearing that under my clothes. It was a headfuck … but so horny!

One thing is to wear it secretly … the other to expose yourself in such gear. Why do you like that other people can see you dressed up like a little bitch?

That’s a line I’ve only crossed a few times. I’m still yet to go to events or saunas dressed as a fem boi. I don’t think it’s something I could do on my own, I’d need a real man to guide and support me through such a thing. I mean, doing this article and showing off these pics is quite a big step for me 🙈.

Yes I know I was a bad boy to persuade you to do this interview. But I think at the end this little bitch will like it. Or am I wrong, boy?

If I didn’t like it I would not have said yes 😘

I would say EXPOSURE seems to be a big kink of you. Wasn’t it also one of the reasons to start with porn?

However did you guess? I know that even though I struggle to admit it, deep down I’m very much an exhibitionist. I guess it’s part of my naturally submissive side. I definitely derive satisfaction and pleasure from showing myself off and giving others pleasure. However that happens to be.

To play with limits is for most of us kinksters a special attraction, even more if they are connected with social taboos. Do you think this girlything is such a borderline you have been attracted to pass over?

I wouldn’t say I was attracted to it at first, but it’s certainly something I’ve been sucked into and found I loved… Even if at first glance I would have passed it off as a fetish that wasn’t for me.

But the more I’ve delved into it, the more I would like to be pushed past and over this limit I seem to have in my head.

Hehe. Good to know. But it is not the femininity which attracts you. It is not a gender play for you. It is the desire and need for humiliation and exposure which turns you on. Am I right and are there other such dirty secrets, other borderlines you would love to get forced into?

I would say it’s a 25:75 split. 25% femininity/forced gender play and 75% humiliation. I guess I’m still working things out, every time I try it’s a learning curve.

And you are right, I have many dirty and taboo secrets. But maybe that’s a story for another day? I could go on for hours.

James Oakleigh

United Kingdom

Hey, if you're cruising on KINKFINITY, you probably know I'm the master of this fetish blog. BDSM isn't just sex for me; it's a lifestyle I've embraced for over 25 years. Along the way, I've met some fantastic kinksters—some dropping by my massive 200m2 dungeon for parties, others for days or weeks, and a few as 24/7 long-term slaves. Swing by my Bluesky account for more:

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