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Quick intro: I write erotic stories that are mostly fantasy, with elements of reality mixed in. This is not that.
This is documentary.
I have been tasked by my dom to wear a chastity cage for 90 days. Each day I send him a photo of me in my cage with a note saying "Thank You Master."
The purpose of this project is to feminize me. To change me. To rewire my psychology. To humble myself.
Here, I will record my thoughts and reflections. Everything will be 100% truthful. Anything omitted will be left out only if it's irrelevant.
Here goes.
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Preamble: These are the days of COVID-19. Ten years from now, young sissies are going to ask, "what the fuck is COVID-19?" Quick answer: it's a really annoying disease that makes us all stay in our houses.
Before I met my master, I was on a journey. I was starting to explore my feminine side. I've been a crossdresser since I was in preschool. Some girls made fun of me for wearing fingernail polish. I am a sensitive and at times a weak person. I took it personally. I put my crossdressing in the closet.
I am also a man attracted to other men. I am not, culturally, much of a gay man. I could pass for straight to all but the keenest eye.
Ultimately, I am a fairy--but only to those who can see me for who I am.
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In the early stages, I did not document myself on a daily basis. As a matter of fact, I was not sure who even started our relationship--me, or my master.
I just looked it up. Here is our correspondence.
SexyAmie 42MtF Bottom I'm Amie. I'm somewhere on the trans spectrum, trying to figure out where. I like to dress, not just in lingerie but in outfits, with makeup. I want to be a girl not just in bed but in life. Anyway, that's a little bit about me... can we be friends? Xxoo Amie
Master 50M Master I have accepted your request. I like your profile. I also have a SO. I have been married for 21 years. So we are in a similar situation. I see you are Los Angeles. I'm in Phoenix. Not that far away. Can you tell me more about you? What experience do you have? What are you seeking on here?
SexyAmieÊ 42MtF Bottom Yes, absolutely. I am looking for someone to be, in a way, my boyfriend. I love men. I am only attracted to men, have been since I was a teen. I've been "gay" for a long time (since 2001), but that label never felt like it described me. I want to be a woman for a man. I've been that... twice. I played a show with my band when I was dressed as a woman. A super, super slutty womanÑlike, over the top. I got laid that night. Which was fun. And then I tried to get laid with my husband but... he couldn't get it up. He is not into me dressed as a woman. So here I am, in a committed relationship and no way to express my femininity, at least not sexually.
Master 50M Master I totally understand. I have a deep need to dominate and my wife just isn't into it. So I am seeking a girlfriend like you seek a boyfriend. Not to replace my marriage but to add to it. I am not seeking to get stds though. I don't want to be with the town slut. I seek someone who is very safe sexually and does not have many partners. For me, my only partner is my wife and whoever I am with as a Dom. And I am very careful about who that is. Are you into being dominated at all or mostly just fucked as a woman?
SexyAmieÊ 42MtF Bottom I am into being dominated... I think. I say that with hesitation only because I haven't done it, really. I've ALWAYS been a total bottomÑmy goal, very literally, is to make you, the man, happy. Can you teach me?
Some of you are going to ask, who is my master? Well, he is someone I met on another website. If you find him there, try to seduce him. Give him 75 days. He's got his hands full with me.
Day 5 -- September 10, 2020 Master asked me to show myself with my natural hair. This is both a dream come true and a nightmare. I have grown my hair long because I want to be more femme. But the photos I've taken of myself in my natural hair are very revealing. I look sexy, quite femme, and 100% myself. My deniability once I send this is pretty much over.
I send a photo.
Day 8 -- September 13, 2020 So maybe I am a submissive? Maybe I'm more than just a bottom? I've now gone 8 days without a male orgasm, one day longer than I've ever gone. All I want to do is please him.
Day 10 -- September 15, 2020 Today is the best day so far.
I feel so fucking femme. I spent the entire day in bra, panties, and makeup. My husband, who is only attracted to men, is not impressed. I woke up in the panties. I put the bra on at about 11am. I started applying makeup at about 3pm (actually, I started tweezing my eyebrows then, but it was part of the full circuit).
Who sits in their desk chair all day in a bra, panties, and makeup?
That's the question I have to ask myself.
Because I did.
Day 11 -- September 16, 2020 Today was a bad day.
I told my husband that I was under chastity for 90 days in total because a man I do not know personally told me to do so.
He didn't like that so much.
That night, I drank a little too much. Then I stepped out for a cigarette.
I don't smoke.
The cigarette kicked my ass. Kicked my ass so hard I fell over backwards. Funny... I almost fell over backwards. For a second, I thought, "wow, I almost just fell backwards over the barbecue grill."
Ten seconds later, I fell backwards over the barbecue grill.
Funny, isn't it? Until I was covered in dirt, grit, and blood, it was hilarious.
I came into the house and made a big show of how wounded I was. Husband was super pissed and unimpressed. He figuratively took a shit on me.
I went to sleep on the couch.
I woke up at 3:30am. My leg was throbbing. I had tripped over a rusty grill. I had brought back in with me burs and dirt. I needed to wash up, my drunk ass thought.
But as I washed my leg, I saw a new problem emerge.
I was dripping blood from my crotch.
Fuck.
I'd been planning to wear this cock cage for the rest of the 90 days. Fuck sanitation. Fuck weekly cleanings. I was in it to win it.
That was a bad plan.
To clean up my crotch hair, I had used this "magic" powder. I think a little of it had gotten caught above the crotch bar.
You don't want that, I've learned, because it'll eat the fucking skin off your body.
I was dripping blood because there was no skin left on the underside of my balls.
This is pathetic, but... the next day I sent a photo to my master of my bloody panties.
Wow. Am I really that big of a pansy?
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Day 12 -- September 17, 2020 The next couple of days were spent in recovery. I did not sleep in my cage. By the way, most people do NOT sleep in their chastity cages. I do. It's a little gnarly--my boner tries to grow every night within the cage. Sometimes it wakes me up.
I gave myself two nights off.
Those nights were, weirdly, more miserable.
I spent entire nights with a hard-on, each one about one-and-a-half strokes away from cumming.
But I can't cum.
My master asked me not to cum.
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Day 14 -- September 19, 2020 My master is not feeling well. Still, he managed to make a request of me:
"It's very easy. I want you to keep your ass wet all day. Carry lube around with you and keep yourself wet 24/7."
I went around for a day trying to live my life as a man, with my dick in a cage and a perfectly-lubed pussy in my ass.
Quick aside: It's funny. You probably think of me as a full-on fag. You think I'm some petty princess crossdresser, a homo queen with limp wrists.
You couldn't pick me out of a lineup.
Unless I showed up in just the panties I'm wearing right now, you would have no idea I am the fairy that I am. You would never dream I'm the guy who will suck your cock to completion, no hands, then clean you up with just his mouth. That I could take your cock up my ass and work it like it's never been worked before. Take your load inside me with joy and enthusiasm like you've never gotten from any woman.
But that's what I do.
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Day 15 -- September 20, 2020 Day 2 of me with a lubed-up ass. Fine, baby. I can do that.
Today I had a busy day. I work Sundays. Most people hate that, but I love it.
At the end of the day, husband and I went for a bike ride. You can imagine I could feel my lubed-up ass (fuck... lubed-up pussy? I fucking hate terminology right now...) rubbing against my seat.
When we got home, I made him fuck me. It was too goddamn much to walk around with a WAP--a wet-ass pussy--that had not taken a proper fucking.
I rode on top of him.
I've never had sex when I never thought of my own penis. Today, my penis was irrelevant. The only point was using my ass to make him feel amazing.
He fucked me great.
I took him like a fucking champ. Some bottom bitches need to adjust. Not me. My man has a seven-inch, curved, above-average thickness dick. I rode it hard. He was polite until I said, "the best thing you can do for me ever in my life is to put your cum deep inside me."
Then he started going for it.
I held steady. I fucking loved it as he hammered against my ass.
A couple of minutes later, I had what I wanted.
As he went to the shower, I stayed in bed. I played with my g-spot while he cleaned up. I had a moment. I did not cum like a man, but I ended up weirdly satisfied.
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That's a true and brief report on Days 1-15. I'm going to go out and smoke a cigarette in my panties. See you on Day 30.
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What do you think? Drop me a line at sexyamie@hotmail.com if you're turned on.