Writing for Miss Melissa

Writing for Miss Melissa

smooth-boi

Author's note

We continue from Training for Miss Melissa. Please read that first!

Introduction

I've only been writing dialogue since Miss Melissa and I have started reconnecting. So now I have to actually write some content. Being an essay, this wasn't too bad because I'm only writing a stream of thought and not characters, plot. That's going to be the next challenge.

Miss Melissa was checking in a 2 to 3 times a week following our conversation, and I had to snap some pictures for her. She only asked at night, so I was all geared up already. She was thrilled of course.

I had to ask for an extra week before writing the essay because of work. Miss Melissa asked me to use my riding crop on myself 10 times to redden my ass and send her a picture as punishment. My clearly semi hard cock told her that we would be revisiting this.

It was way easier to maintain this level of discipline than I thought. The nudity was the easiest because I'm nude most of the time at home anyway. Now it's all the time. I do keep some clothes nearby in case anyone comes to the door. It's been too cold to go outside so far. The weather is just starting to change now.

One thing we didn't talk about was body hair removal. I've been shaving off everything most of my adult life, regularly. I don't think it came up because it's just part of my lifestyle. Miss Melissa has never seen me with body hair. In fact, last time I had any appreciable body hair was when I was a virgin.

Cock ring

Turns out if I moved the bottom of the cock ring behind my balls just a little forward, it didn't bite as much, and I could wear it a lot longer. I can go the entire day easy now. On the weekends or working from home, I just put it on when I get up and take it off for bed. For meetings at home too. Except in the shower or having to piss. I also got to the point where I didn't have to take it off after I jerked either. I can just relieve the pressure after cumming by shifting the ring just a bit forward. I also think the leather is more broken in now from regular use. I've worn the cockring out going grocery shopping with no issues. I've since taken to wearing it out for errands in general. Now, it's still cold out, so it's not noticeable. When the warmer weather comes around and I'm not wearing bulkier clothing, I am a little concerned. I don't want to get in any trouble in public places. Of course, I might not care by then either, so that's something to think about coming up. Basically, I've been wearing it all the time except at work or for sleep. It's not a distraction and totally comfortable. I crave wearing it and it's part of my identity. With the plug, it's not always easy to wear going outside. The chain, there's not really a reason to wear it while clothed. The ring is easy to wear anytime, and I'm always aware of it. Worse comes to worse, go to the bathroom and take it off. Maybe the metal ones might be a challenge, but just get one that snaps on and off.

Plugging my ass

Similarly, with the plug, I'm doing the same. I put it in once I get out of the shower and can leave it in all day. When I'm at home, that's 12 hours at least. Even with meetings. I forgot how much I enjoyed the full feeling it provides. I've been able to keep it in after jerking too. I haven't worn it out yet because it's really cold out still. I'm at the point where I could level up now. I have a huge metal plug that's about 7 inches around, but it's too much. I need something in between. It just feels good to be filled.

Chain

And with the chain, it's the same. At home, I just put it on when I get up and take it off for bed. Or, put everything on after I strip down when I get home from work. I even bought a couple more chains for variety. Miss Melissa went wild when she saw the new ones. They're much thinner and don't leave the mark like my original thicker one. We both think they look better. I really don't know why more men, or anyone really, doesn't wear them. The only reason they're for women is because only women really wear them. The chains I have aren't really feminine. I don't know if wearing the chain automatically translates to queer, but it might signal kinky or bottom on a male. It's less intrusive than a collar. I think any exhibitionist or nudist should really think of wearing them.

Jerking

I had been jerking only once per day, even on the weekends. I'm edging while I'm working, not totally hard but just staying kind of semi with a quick jerk every so often. I wait till early evening, and by the time I am ready, I've been having the strongest orgasms and the most in terms of quantity since I have in years. I'm actually more focused working because I know I'm only going to do it once, and I'm saving up for it. I'm surprised that only once per day was all I've needed for the most part. I've since been going to a second, but I'm still not jerking at all until early evening. More on the second below.

Dildo

The dildo practice needs more work, but that will come in time. Part of the difficulty is in mounting the dildo properly. I'm still looking for better solutions. I have to lube it up, but I can get in about half of it if I wear the plug to warm up. It does start to hurt after a while, but it's only been a few times I've been practicing. I think by the time the summer rolls around, I'll be able to take it all. Maybe not a huge pounding, but just taking the full length of it. The thickness isn't a problem. It's bigger than my strap on dildo. I tested that out after about 3 weeks, and I can take the strap on no problem. So it's just a matter of keeping at the dildo.

Porn

I consume much more porn now even though I am limiting my release. I started chatting on lit regularly. Usually after dinner and on the weekends. Not during work. I even created a gay male bdsm room. Not a lot of activity, but I'm keeping it going. What I like is that it's helping to maintain a submissive and queer headspace. Lots of men share my outlook on just not being hetero anymore and what that means for them. They're almost relieved to tell me. For most of the men my age, they're married, and that's a challenge if they can't talk openly about it. These interactions have been keeping me edged mentally. Since, I've sometimes had to jerk for a second time in a day. I stay focused on gay porn only as instructed and got super hard when I found muscle jock bottoms being tied up and fucked. Most are a too hairy for me, but the scene is incredibly arousing. I'm just exploding when I jerk to gay porn even for a second time in one day. That's a big deal for someone my age. Gay men have starting to be more of my jerk porn now than I used to. Even for the first time. I'm not saving it only for the second. It's probably more than half now. I've created a go-to gay male list. I'm still most interested in interracial gay bdsm, but the jocks and muscle bottoms have been a revelation. I'm not jacked up or ripped, but I am in good shape, probably more than average. Maybe it's easy to see myself in those scenes.

Pissing

Sitting down to piss was weird at first, but I got used to it in about a week. It's actually helpful at night. There's a night light in the bathroom, but it's still hard to see. Also, guys know sometimes the stream just goes all over the place for literally no reason no matter how hard you try. I haven't been to anyone else's house where I've had to sit down. I don't know if it makes me feel beta, but it's comfortable for me to do it. I actually was out at a work event in the evening and when I went to the bathroom, I almost did go in and sit down. Clearly, I'm becoming ingrained with this routine. I have had to take the ring off to piss because it took longer to get going, and I'm working on being able to leave it on.

So far so good

I'm really enjoying my discipline, and I'm motivated to keep it going. This is more structured than I've experienced, and it's clearly benefiting me. I'm actually banging at work, whether at home or in the office because I know if I can knock down everything for the day then I can just goon out and not think about anything until the next day. It almost feels irritating or annoying if I'm not nude with my stuff on and in. Even working at home, once I gear up and sit down to work, I'm highly focused.

Miss Melissa responds

I can't believe how much my gayboi is so submissive and obedient! And you are my gayboi now. You've proven it. You're thriving under my discipline, and I know you'll be able to do more when you submit to me in person. This may be the gayest you've ever been, at least mentally, even though you haven't had actual gay sex in a while. I like that you showed initiative to buy more chains and you've accepted wearing them as part of your look. You never wear watches or jewelry or anything like that so it's hot that you've found an accessory you're excited about wearing. I don't know why men don't wear them more either. I'm still saying, you're setting a trend. I would like you to wear it in a public setting. Wearing clothes, it's not like anyone knows, but you will know. Start with just for a little while.

Really love how the cock ring is part of your identity now after barely over a month. It's kind of exhibitionist, but you're just putting it on as part of your day. That's very exciting. I'm not going to require this, but at least check out some new plugs. You actually have a lot more experience than me with plugs, so you know what would be best to get. Seems like the one now is going well for every day.

It would be great if your plug wear was as a constant as the ring wear is, but, being real, you have to listen to your body. When it gets nicer out, try just a small excursion here and there like we talked about. Walking around shouldn't be an issue because you have a lot of experience there. I think getting just one short car ride under your belt will go a long way.

I'm positively thrilled you've taken up engaging with other men about your sexuality and being able for them to talk it out with you. That's not something I thought of, but it seems like it's a natural outlet from your training. I'm totally in to seeing how else this comes out. I want you to act on your impulses like this. Are you doing anything on the lit boards? I'd like you to find some discussion threads you can contribute to and keep chatting.

I know you're identifying as queer, and it took you a while to get there. I'm proud of your acceptance. In reading your essay though, I'm feeling your training might be revealing you're homoflexible. You're engaging with men more, and you're more attracted to gay males in your porn habits. I've known you for a while, and this is a trend in your sexuality we've seen before. Once you went to Dore, you started getting frustrated with your girlfriend. You tapered off sex with her, and you haven't had sex with a woman since. In real life, you're really only getting off with men, whether Folsom or when you went to the bookstore. Other than me, you haven't expressed any interest in a woman in your life. It's literally been over a decade. Back then, there wasn't really a term to describe it. In your essay, I noticed you didn't mention trans girls at all, and you were very enthusiastic about talking to men more. It really stood out to me how much the muscle bottoms resonated with you. That's been new.

You don't have to do anything, just keep it in the back of your mind. Neither of us think you were born gay, but your chatting now and supporting other men, which I love, and your growing attraction to gay porn to get off is telling me there's more going on. I think this is healthy for you! I'm more convinced that you should try some weed even though I'm a total pothead. I know that's a no go out there, but let's talk about it for real. I think we're learning a lot more about you in such a short time, and there's so much more to explore!

You're such a good boi. I don't know why I was embarrassed about saying I love you. I did tell my sissy. He wasn't totally thrilled at first. I had to explain that you're not actually any sexual competition for him. He couldn't quite get that because you were such a pussy hound. He came around though. I guess I'm poly now? That's something that I have to think about because there's no way I'm turning off my feelings for either of you. We've really taken quite the turn! I'm excited and I can't wait for what's next!