Converted to Gay

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This story is partly inspired by messages from fans, with slight adjustments. Thank you for reading.


I wanted to share with you one of my current projects. A twenty five year old male by the name of Eric. Nothing too special in the looks department, but not too shabby either. He was neither heavy or slim, perhaps a slight softness to him. His eyes were a darker brown and green and their shape was pleasant. His nose was an adorable button to push, and his dark hair was short and messy in a way that was naturally stylish. He occasionally flirted with letting his facial hair grow in, though other parts of his body were sparsely coated. His penis was a darling thing, a full four and a half inches, though I doubt he thinks of it in those terms.

His situation fit my profile: a single male, with a moderate social life, a couple of friends, close friends, a couple of girlfriends but some time had passed since his last meaningful relationship. And importantly, he was a virgin. Employed, single, living alone, and a little secret: he would occasionally indulge in fantasies of sucking cock.

The internet has been a wonderful tool in this regard. Gaining access to peoples’ computers or phones, their online accounts, all their secrets. A person’s browsing history, what they download, their social media, and usually their dating information, all there, all help me narrow down my projects. I must admit, I’m rather proud of myself for how well this one is going with Eric, and I thought I’d share some of his journal entries with you.

Day 1:

Dear Diary,

My owner says I have to write in you every day, and that I have to be honest or they’ll know. That you’re to be my one and only confidant. They know I like to watch videos of men sucking on other men’s dicks. They know which pictures I liked to look at the most. It’s just an occasional thing. I’ve had girlfriends, and I do like women. Sometimes it just feels a little naughty to imagine sucking dick.

I am not doing this of my own free will. Blackmail is effective. With what they have on me, well, you just don’t want people to know that kind of stuff. So here I am. I’m promised that as long as I play along, they’d let me go, and things would stay between us. I don’t believe it, but I don’t have much of a choice. I know you’ll be reading this, and since you want me to be honest, so it shouldn’t be hard to believe this is fucking crazy.

My owner says they’re going to help me be a good gay boy. And as much as I wish I had a way out of it, I don’t. Today, they sent me a link to a video of a young man happily slurping away at another man’s dick. The angle had the camera looking down and capture the look of intense need in his eyes. My favorite part was when the shot changed to capture his face and his own rock hard dick tenting his boxers, the tip showing it was wet, and that meant he was turned on.

I’m too afraid not to be honest. I don’t want anyone to know, and writing this down is messed up.

Day 18:

Dear Diary,

The cock in today’s video wasn’t the biggest, but I think it was the best. It was thick, and very hard, you could clearly see the veins along the side. Owner keeps sending me videos with boys in panties, and now they’ve ordered me several of my own. So far nothing bad has happened. That doesn’t mean I like this. I’m a guy and I’m horny. But owner has kept their part of the bargain, so I guess I should continue keeping mine.

Day 24:

Dear Diary,

Owners has me by the balls. I had to take pictures in the panties they got me. They weren’t happy with the pictures, too much hair they said. So I had to go out and buy hair removal products. Owner said everything from the neck down had to go. That the men getting their cocks’ sucked in the videos had hair, but the young men didn’t. I was not eager to do this, but there I was rubbing creams and shaving in places I never had not even half an hour ago. I know you’re reading this, sicko, yes, it does feel kind of good.

I sent back pictures of my hard cock in a pair of pastel pink panties. This is terrifying. But no one is treating me any differently, no one knows a thing. The worst part is owner has been sending me more videos of cross dressers sucking cock, and effeminate men in lingerie providing their mouths for use. I’m not blind.

Day 26:

Dear Diary,

Another package was waiting for me when I got home from work today. It was a pair of matching floral pink stockings, to go with the first pair of panties. Owner says I have to get used to being a sissy by starting to dress like one. They already have pictures of me in panties, so me in lingerie wasn’t going to hurt any more. I took some pictures of me in them, for my owner.

It’s really starting to drive me nuts, I have no idea who’s doing this to me. But what’s really starting to scare me is I’m looking forward to this. It’s a sick and twisted game, but I’m thinking about it all day at work, what new video I’ll have waiting for me. Yesterday I was so turned on I had to take use my lunch break to masturbate casino siteleri in the bathroom. I really hope no one could tell.

Day 34:

Dear Diary,

Owner is displeased with me. I was sending pictures of me licking cum out of my hand after I had jerked off to the most recent video, a short haired young man sucking a dick through a gloryhole. Some of my body hair was showing, I didn’t think anything of it, but owner was not pleased, not at all. Getting rid of body hair is a pain in the ass. I said I was sorry, but I guess that wasn’t good enough.

Owner let me know in no uncertain terms that I was a sissy faggot, and that means I need to be hairless. I don’t like that word. I’m not gay. Owner hasn’t been letting me masturbate to anything but all this gay blowjob porn, and I’m too afraid not to go along. I do get turned on, and I can cum to it, but I just don’t like men that way.

Day 38:

Dear Diary,

I don’t think I’m out of the doghouse yet. Owner has been sending me lots of pictures. Mostly sissy training stuff. Pictures of sissies, gay men in lingerie sucking away on thick pricks. I can’t help but notice the similarities between me and them. I haven’t gotten any new clothes yet, but I find myself imagining what it would be like.

Owner had me jerking myself off all weekend, I didn’t even step outside, as you know. Sometimes I would get on my knees when I masturbated. Owner says I have to get used to the taste of cum, even if it’s my own sissy cum, so tonight I’ll be spilling my cum into my panties, then licking them clean. That turns me on now, but I know after the fact is a different story.

Day 58:

Dear Diary,

At this point, I’m pretty sure owner has quite a bit of money. I just got home, and there was another package in the mail. It was a very long, nice looking wig. It was long and a dark brown. It goes down almost all the way to my butt, which is looking better by the day. That gym membership has been paying off, and I’m even glad owner did it. Now I can look more like a sissy.

It’s just the gym, I keep telling myself. But I can understand owner, I think. They want me to be around all those men at the gym. They want me imagining what they’d be like naked, or what their cock’s look like. Or taste like. As if I needed a reminder, dick is pretty much all that’s on my mind lately. I don’t even know what they’d think if they had a clue what was going on. I can feel their eyes on me sometimes.

One of the guys is always there around the same time as I am. Same work schedule, I guess. He’s kind of wide, and he showers there, and my heart gets stuck in my throat each time he heads off to the showers. Even writing this and remembering it makes me hard.

Day 65:

Dear Diary,

Owner just wrote to me! I feel kind of proud right now. Owner said the latest video I sent him, with my make up right (finally!) and the wig on while I showed them how far I could swallow the dildo, showed I had the makings of a great sissy faggot. I know this is kind of fucked up, but sometimes I just like to hold it. It’s just a thick piece of rubber, but I like holding it. Owner said they’re glad I’m being a good queer boy.

I don’t feel gay. I’m reading this, and I know that sounds nuts. I know that every time I masturbate, it’s to more gay sissy porn: videos, pictures, captions, stories. Sloppy blowjobs, or a sissy’s eyes full of worship as they stare up at a more masculine man. One of the cuter ones I like has this choker, and I think I’m going to order one for myself. I’m going to go watch one of my favorite videos, while practicing my cocksucking and send owner another video.

Day 65 – Entry II:

Dear Diary,

Oh my god. I know I haven’t done two entries in a day, but I need to write this down. I guess I knew where this was going.

Owner really liked my latest video. They responded with one of their own though. The first one they’d send me with a sissy being fucked. The guy was referring to them as a woman. Y’know, “Get on your knees, girl.” Type of thing. It ended with the sissy on her hands and knees as this dude consistently fucked her. My favorite part was when the camera zoomed in on “her” face, and you could make no mistake, they were loving every second of it. They were barely moving, just clearly enjoying the act of being fucked by a real man. There is no doubt in my mind that sissy was gay, and if I’m like him…

Owner sending me this now must mean they want me to do that too. This is a new level. I’ve never had anything in my ass. I like the idea of being a cocksucker. But being a catcher? I don’t know about that. The sissy in the video certainly seemed to like it though. It’s been at least two hours and owner hasn’t said anything else. I don’t know if I can do that.

I’m going to sleep now. I’m going to listen to those audio files owner sent me. The voice is soft, and I know it’s not real, I just like hearing about cocks and gay sex.

Day 65 – Entry III:

Dear Diary,

I lubed up the dildo and pushed it half way in. I guess I know slot oyna if I can know.

Day 94:

Dear Diary,

I’ve been wearing my chastity cage for a whole week now. I wonder what my coworkers would think if they knew. It’s been almost unbearable. I don’t even know why I’m doing this. Owner says I need to get better at taking cock in my ass, and it still kinda hurts. I can’t quite get myself off with it, I just kind of leak for a while.

I was at the gym earlier today, and I saw that guy again too. I was eyeing him as he was changing. I wonder what kind of meat he had between his legs? Anyways, that got worked up and my dick was swelling inside the damn cage again. I had to masturbate with the dildo again until I could get the release I needed.

Day 108:

Dear Diary,

I was invited to tag along with some coworkers for a drink. I begged off because I wanted to get back home and all dressed up. I’ve got my second favorite wig on, you know, the pink one that curves around my face? My lipstick is a precocious pink as well. The black choker went on the minute I was inside, and small A-Cup bra was getting easier to put on. The pink and purple panties with hearts were covering my chastity cage, it had been a week since I’ve been allowed out.

Owner says I have to understand that my penis has no use, so I’ll need to get used to anal sex. Girls with strapons are not doing it for me nearly as well as I thought. I might start off thinking about them, but then I think about having a real dick in me. A real, flesh and blood cock. Like the guy at the gym’s.

I think owner was right. Putting up those posters helped me. Big, tall, masculine men with hard cocks, one on every wall. The mirror was a constant reminder of what I wasn’t. It was a reminder that I wanted those men to use me. To have gay sex with me. That I am a sissy faggot. I told owner as much, and they seemed pleased. I’m going to spend the entire weekend like this, I think.

Day 119:

Dear Diary,

Twenty eight today. It’s getting hard to keep track of them all. If I see a man, I try and sneak a peek at his crotch. It’s not that I can’t count, it’s just that I’m doing it so frequently, sometimes without even intending to, and it messes up my count. I’m sure owner wants it this way.

And while I don’t have much of a choice in this, y’know, I agree with owner: I am absolutely gay. I was useless as a guy. I like cocks, and I like them in all my holes. I’m gay now, I guess. OK, more than guess. I can’t even look at a guy without thinking about sex now, and my poor dick strains against my cage. Which hasn’t been off in a while. Milking myself is just not very satisfying, or maybe I’m just not very good at it. I’m just fucking horny all the time.

Day 134:

Dear Diary,

Owner has started to call me Erica. Fuck, that turned me on. I love being in the girls role. It’s the only one I can fulfill, the only one I want. I know what people would think if they knew, and that only makes me want it more. I am a sissy faggot.

I know owner can do whatever they want to me. I’m not worried about that. I think I’m going to ask owner if I can have sex with another man.

Day 135:

Dearest Diary,

Owner said I could have gay sex! Yes!

They also said they were proud of me, for asking for it and because I was becoming a fairy boy, but for now I still have some work to do. Apparently I’m not queer enough yet. Owner will help find me a man, but they want to make sure I’m ready.

Y’know, diary, this isn’t as bad as I thought it’d be. It’s not that bad. I can’t stop thinking about men, and it’s sort of taking control of my life, but I think it’ll get more under control once I’ve had gay sex with a man. I guess I was pretty repressed. If you’d asked me a few months ago if I’d have sex with a man I would’ve been disgusted. No way. Faggots do that. Even when I masturbated to gay sex before, once I was done, I didn’t think about it. Too ashamed. It’s not the same anymore.

Of course I’m often dressed up in lingerie, make up and a wig while I slide my dildo into my ass and dream of real cocks. If owner doesn’t think I’m sissy faggot enough yet, I can’t wait to see what’s coming!

Kisses, Erica

Day 140:

Dearest Diary,

Owner has been sending me lots of videos. All of the men are bigger than me, some taller, some wider, sometimes both, muscular and overweight, some have a lot of hair and some have a little. Bald guys and clean shaven men, and men with beards and they’re all older than me. I’d suck all of their cocks, happily. Being fucked also looks so tantalizing.

But owner said it’ll be another month before they’ll find me someone, and only if I’m ready. Coincidentally, I won’t be allowed to unlock myself until then either. I don’t know if I can make it that long! I’m really horny pretty much every day, most of the day. It’s not about my pleasure, it’s about their pleasure. But I am very greedy and horny sissy faggot now, and it’s really difficult when I can’t satisfy my homosexual urges. See you again canlı casino siteleri tomorrow!

Kisses, Erica.

Day 149:

Dearest Diary,

I am really regretting the time I spent being interested in women. I know how gay that sounds, but still. As you know, owner has been sending me more and more specific videos, of older guys. Bigger guys. And they’re always hairy. I’ve been keeping myself hairless like a good sissy, but even before that, well, these guys had way more hair than I’d have ever been able to grow. There’s all kinds of fucking now, but there’s a lot more foreplay now… and a lot more kissing. My caged dick starts throbbing at the thought. My milkings relieve some of the pressure, but it’s not satisfying enough, and I haven’t touched my penis with my own hands in well over a month now.

Kisses, Erica.

Day 155:

Dearest Diary,

Today I chose Matthew’s picture. Like the others, it’s just a headshot. He looks to be in his forties I think. He’s clean shaven, but you can tell there’s stubble. I like the hard edges of his jaw, it gives him a very “mountain man” look, and I wonder what the rest of him looks like. Especially what he might be packing. I know I’m supposed to focus on his face, but sometimes that’s difficult. He has bigger lips than mine, and his smile isn’t that bad. His eyes are a darker brown, and his hair was combed back a bit, and thick, like I could run my hand through it.

I kept the buttplug in me the whole hour, while I sat there fantasizing about Matthew. Wondering what it would be like to be kissed by him. That I wanted to kiss him. His smile is growing on me. That I would very much like to do some very gay things with him. Once the hour was up I swapped to my dildo, and came so close to orgasming, but in the end my penis had stayed mostly soft and some cum dribbled out for a while. It really was becoming useless. Good thing I don’t need it to please men, isn’t it?

Kisses, Erica.

Day 162

I’m sooooooooooo horny!

It’s so much work just to milk myself by this point. Like those silly audio files say, I’m just a sissy faggot, and don’t deserve to get off unless I’m pleasing a man. Maybe that’s why I can’t seem to orgasm. I know anal orgasms are a thing, I must be doing it wrong. Or maybe I just need a cock to get off. Mine doesn’t count, even if it weren’t locked away.

I’ve been trying out all the outfits owner has been sending me too! I was just posing for a bit in the classy black set I was so gaga about the other day. I want to be able to please my man, after all!

Kisses, Erica.

Day 166:

Dearest Diary,

Owner found me a man!

I only got to see his face, and what a face! It was mostly flat, but he had beautiful big lips. He was definitely a bit older, like not as old as my dad, but not that far behind. He had these little creases in his forehead above his bushy eyebrows. Large dark green eyes a sissy could lose their eyes in. It was all heard lines, covered in a thickening beard tinged with grey. His hair was dark and combed sort of to the sides, stopping before his ears, and there was definitely some grey there. I couldn’t really see any chest hair, but I’ll bet it’s there! His shoulders seem wide…

Owner says he’s safe, and that’s good enough for me. I’m clinching so tightly into my buttplug as I write this! I want to bend over for him and squeeze out my plug for him. I hadn’t ever felt anything like this for a woman before, and I guess the reason for that is because I’m gay.

So, yeah. Tomorrow. Here. I’m going to lose my virginity being penetrated by a real man. Whatever makes him happy, I need to do. Next time I write to you, I’ll have had cock in me. Surreal.

Kisses, Erica.

Day 167:

Dearest Diary,

Well, I can confirm I am no longer a virgin, and completely gay. I’m going to tell you everything I can remember, because I want to remember this forever!

I don’t even know his name, but I know I want to see him again. I had my buttplug in until ten minutes before he showed up, I wanted to be nice and ready for him. I knew I could not answer the door, I could hide. Owner would be angry, but I could. But I was too excited, my heart was jack hammering in my chest: I was standing there, completely as a gay sissy. I had my fishnet stockings on this time, with new two inch heels. I could barely walk in them! No panties either, nothing to hide my penis, soft and caged.

My make-up was subtle, accentuating my eyes and my lips which were painted bright pink. My favorite wig too, the one that wraps around my face, the silky black one that matches the sleeves I had on. I remember thinking I hoped I was pretty enough for him when his knock came at the door.

I peeked for just a moment, honestly, I looked so fast it could’ve been anyone, but I opened the door anyways. He looked like his picture! He had to be a little bit over six feet tall. And he’s built like a brick house. His shoulders are so much wider than mine! Even clothed, I could practically smell him once the door was closed. I could feel myself becoming aroused in my cage, the coldness against my warm flesh muting my pleasure for a moment. I had to look up at him, which was really hard to do! I guess I’m still kind of nervous about being a faggot.

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