Meeting Miss Melissa (sort Of)

After getting a real job and moving to a much, much more red area, I continue my friendship with Miss Melissa and our exploration into bdsm and sexuality. Now, Miss Melissa has her own sissy who enjoys dressing and bondage. They have a part-time Domme/submissive relationship and are sometimes just boyfriend and girlfriend. She likes it, but she really wants to experiment with a submissive male into a wider range of kink. I'm paraphrasing a lot of our chats because she's helped me and I want to help others going through their own transformations. This is a huge amount of setup, but I think there's also some character development.

A few years later from Dore Alley and into Covid

Timejump -- I went to Dore Alley the next year for a second time. I didn't end up going to the bar again, but I felt more confident approaching other queer and gay men to frot and take pictures. Those are on my fetlife profile. I also went to Folsom later that year with a group of people I met on Craiglist (when you could do that) and was led around on a leash for the day with a few other gay male submissives. We were quite the attraction. I finally got a real job the next year and moved to a place not at all like San Francisco. But, I started going to munches, which was a huge step, and much to the delight of Miss Melissa. I still go and are friends with many people in the local kink community. I do wonder what I would have become if I had stayed and not moved.

smoothboi -- Hi Miss!

Miss Melissa -- smoothboi! How is the pandemic?

smoothboi -- Quiet and working from home. How about you?

Miss Melissa -- I'm considered 'essential' so I'm working and it's even crazier than usual because of having clients wait outside. Nice to work from home I bet. Are you nude? Plugged?

smoothboi -- For the most part. Also, wearing the belly chain a lot now too.

Miss Melissa -- I fucking love that. tbh, I'm really worn out though. On top of work, there's my kid's school from home to deal with. I'm glad I have help.

smoothboi -- I bet. I hear that here too. Everything is moving online only now, but it's not a ton of work though. I think we'll be working from home into the summer at least.

Miss Melissa -- More time for gayness.

smoothboi -- Yeah this queer side isn't much of a side anymore.

Miss Melissa -- Hahaha GOOD!! Finally. I love where you are now. You need to get something gay-gay going. Last thing you told me after Dore was getting jerked in the men's room at the mall.

smoothboi -- No, I went to the bookstore and jerked off for those guys.

Miss Melissa -- Yes! I'm so proud you did it on your own too! This pandemic killed fun for everyone. I'm so tired. ttyl.

... Summer

smoothboi -- I've been back to work. This is the longest I've been clothed all year. But, I've been hiking, and my legs are getting super jacked.

Miss Melissa -- You can do that type of gay porn when the men have those muscular legs and they're naked except for socks and sneakers while they pound each other's assholes. Except you'd always be the bottom.

smoothboi -- I wish I could get away with it. Are you still watching a lot of porn? You'd said a while back you lost interest.

Miss Melissa -- Not as often as I used to :/ The only porn I watch anymore is gay porn or sometimes trans. Because anything else I'm into I can do any time.

smoothboi -- I like femdomme if it's pegging or bi encouragement, but I go to trans and gay first. Not a lot for me much either. I do like the audios and captions for a quick jerk.

Miss Melissa -- Of course you do, because you're totally gay now. And that's hot. We need to get you fucked and go gay for real.

smoothboi -- I don't think there's any activity going on anywhere with the virus. We haven't had a munch in months.

Miss Melissa -- Yeah, I know. It's ruining everything. Thank god for weed.

smoothboi -- Oh right, it's legal there. Just about everywhere out here except where I live. So dumb.

Miss Melissa -- I got high and chilled out in our little pool after work. Then I got higher and took a shower and listened to this song on repeat and I can't stop listening to it. But that's not the best part. Why am I telling you this, you ask?

smoothboi -- Why, Miss?

Miss Melissa -- Because while showering and listening to this, I had to pee. So with my eyes closed I leaned against the wall like I was looking down and imagined I was pissing on you.

smoothboi -- Oh hell yes. I got my friend when I was in San Francisco to piss on me and I loved it.

Miss Melissa -- Your gf?

smoothboi -- No someone else.

Miss Melissa -- Who the hell was this? I don't remember another girl.

smoothboi -- I don't think I ever brought her up. We never ended up fucking.

Miss Melissa -- Because you were already pussy free?

smoothboi -- Yes, but it just didn't work out with the timing. She wanted to peg me. So you actually thought about pissing on me?

Miss Melissa -- Right on your chest and face.

smoothboi -- You never really said you thought of doing much with me before. Is it because you were high?

Miss Melissa -- Maybe. I have lately. Thought about you. And us. As Domme/sub. Helping you be a gayboi and just letting yourself be queer. I'm so impressed and turned on with your transformation. And so proud you go to munches now!

smoothboi -- I would be into that. A real Domme is something I've wanted to explore for a while now.

Miss Melissa -- I think I'd enjoy pissing on you before watching you service a gay top.

I think she passed out because the conversation just died.

Still summer

Miss Melissa -- Facebook told me it's your birthday! I hope you did something really really gay today. So you can tell me about it.

smoothboi -- I have been sucking off my dildo sometimes when I jerk.

Miss Melissa -- You need to be gay irl. Do you think maybe you are subconsciously? You told me when those people saw you skinny dipping in the river they probably thought you were gay. I know it makes you feel good.

smoothboi -- I haven't really thought about it too deeply.

Miss Melissa -- They totally did back at Dore and Folsom. That's why you went and you went without your gf. You weren't just acting like a gayboi anymore, and you loved it. Maybe don't think about it? Let it happen. Did you jerk off thinking about being watched. Thinking about them knowing what you are.

smoothboi -- Oh, when I got home for sure.

Miss Melissa -- Your body is responding to the changes you're making. Part of being submissive is acceptance. You need to just let go and let yourself be gay.

smoothboi -- Yeah. I got so hard so easy when I got jerked in the bathroom.

Miss Melissa -- Right. And you were not with your gf. Again. Just you and another man. Try to just relax and enjoy how your body is responding.

smoothboi -- It's hard to get to the discipline of that mindset on my own. Anyone can go out and suck cock, but that's not really what I think I need.

Miss Melissa -- Let me think about that some more. I want to help you get there.

... A New Year

Turns out Miss Melissa is incredibly entertaining when she is high. She could be all over the place. Keep in mind these are snapshots based on years of interactions back when there was yahoo chat and later texting. I noticed she took the initiative in texting me recently and our interactions were changing and becoming deeper.

Miss Melissa -- I have deteriorated into a degenerate pothead in the past year. I am at this moment incredibly high, assembling a storage cart while I squirm around on my couch because I have a glass dildo in my pussy. For some reason I thought of you and wondered if you were doing anything gay at this moment, such as folding laundry with your ass plugged and that gay chain around your waist.

smoothboi -- I actually did just that yesterday.

Miss Melissa -- You should start writing stories about how you've changed and how it feels.

smoothboi -- Can I talk about us and all this?

Miss Melissa -- Yes! I don't write much anymore. I've started things. It's the weed. I'm high as fuck and I'm thinking about pissing on your face. I'd have a male friend piss on you too. Maybe make you kneel on the floor so he can piss all over you.

smoothboi -- I only did it the once, but I loved it.

Miss Melissa -- You never cum without something in your ass, right?

smoothboi -- Yes. Whether the njoy plug or fingers.

Miss Melissa -- Do you ever make yourself cum without touching your cock? Like with a suction cup dildo or something?

smoothboi -- Just from the pegging. I don't have a suction cup one.

Miss Melissa -- You should get one. They're not expensive. I'll pick one for you. Let's look! I use extreme restraints a lot. Your gay asshole needs one. It's really disappointing you don't have one. You're not as gay as I want yet.

smoothboi -- I usually use the Mr S store out of San Francisco.

Miss Melissa -- Is that where you got your cock ring and they jerked you off in the store?

smoothboi -- Oh yes.

Miss Melissa -- I want you to buy one today before you cum. You can't cum until you do. Do it for me. She sent me some links and I got one. It's an 8 inch Titus silicone. Black, of course. It didn't take long to train on it, but it requires regular use to keep my ass in shape. It wasn't the thickness, but the depth. I still can't quite make myself orgasm from it, but I think that's a lack of places to attach the suction cup.

smoothboi -- Ok. Done.

Miss Melissa -- I can't wait for you to fuck yourself hands-free. You're going to want real dick even more.

...

smoothboi -- Guess what came in today?

Miss Melissa -- Yay! You test driving?

smoothboi -- I'm working on it. I sucked it and it feels really good in my mouth. I can handle the thickness without much difficulty.

Miss Melissa -- You're so gay now. So much hotter to me as a gayboi.

smoothboi -- I was thinking the same thing. This crosses a line I've wanted to cross for a while.

Miss Melissa -- You're going to want it all the time.

smoothboi -- I can get about half in without lube, so I think just some practice and I'll take it all. Fuck any last part of hetero right out.

Miss Melissa -- You're not that person anymore.

smoothboi -- I don't want to be that person.

Miss Melissa -- Don't think about it. He's gone now. Maybe part of your training should be not jerking off. Just practicing with the dildo. Maybe use chastity?

smoothboi -- I'd have to think about it.

Miss Melissa -- I think you'd enjoy it. If you like it, you could eventually get a custom metal cage like we did. Do you get hard when you fuck yourself on it?

smoothboi -- Semi, but just in general it's been amazing how easy it is to get hard. I still have to jerk it up, but it doesn't take nearly as long as it used to.

Miss Melissa -- Oh duh, because you were trying to deny who you are. Now you can be fulfilled and filled with cock.

smoothboi -- I don't know if I was denying. I just hadn't been exposed to anything like that up to that point. Once my last gf told me to be bi that was it. Because it was real life at that point. Maybe I needed the permission.

Miss Melissa -- Everything just fell into place. How do you feel?

smoothboi -- Relaxed. Better orgasms.

Miss Melissa -- Listen to Miss Melissa and listen to your body!

...

Miss Melissa -- I got totally high and masturbated in the car. I was watching gay porn then I started thinking about being there the first time you get fucked. Would you like that or do you only need to be with men now?

smoothboi -- That would be a great way to initiate me into cock. Maybe that's why I'm hedging.

Miss Melissa -- Why?

smoothboi -- Subconsciously I need you to be there?

Miss Melissa -- Hmm. I'd think I want that. You know I'm strict. I definitely want to be on camera. We should probably have you wear your mask and broadcast on chaturbate. Then other people could watch you get fucked and they could give suggestions too!

smoothboi -- I'd have to get into that headspace.

Miss Melissa -- I could get you into subspace for it. You want to be my sub and you know how willing you would be.

smoothboi -- That would take some doing but we could pull it off.

...

Miss Melissa -- I got high and made a fire in the pit outside. I'm thinking about you sucking that dildo and imagining sucking a real cock with you. I've always wanted to share a cock with a hot gayboi like you. When it was your turn, I'd hold the back of your head and make you take as much as you could until you started to gag. Then I'd ease up and watch you just play with the head of his cock... we'd choose a top with a nice thick cock to turn you out. I am out of my mind. How's your gay asshole?

smoothboi -- I still can't get it in all the way, but progress. You're thinking about this a lot.

Miss Melissa -- I'm thinking about you a lot since you turned your corner. You're much more comfortable with this emerging part of yourself that sometimes I wish I had a real cock so I could turn you out. I'd make you take the whole thing. We'd train every day until you could. I'd invite men over that you didn't know and make you suck their cock while I critiqued you. No one could touch your cock, either. Part of your training would be that your cock cannot be touched during sex until after the first time you cum with a real cock in your ass. It will make you train harder and want it more.

smoothboi -- All that training and the discipline part of bdsm is what really works for me. And I could be your houseboi.

Miss Melissa -- Is it? The discipline?

smoothboi -- Yes, for sure. It was so frustrating with my last gf because she liked being in charge basically, but couldn't take it to that higher level. Just a run of the mill relationship just isn't for me anymore.

Miss Melissa -- And what else?

smoothboi -- What else what? Like being a houseboi?

Miss Melissa -- That, and your submissive headspace has given you the freedom to let yourself be queer.

smoothboi -- It would be nice to actually share that with someone more actively.

Miss Melissa -- I like how there's just no pretense now. You need real cock so badly. Put your bbc on a kitchen chair and sit on it. Go slow till you can take a little more and more each day. The anticipation of training to be gay for is the best jerk fodder.

smoothboi -- I actually got it in deeper yesterday, but not the whole thing. The thickness isn't a problem. It's less than the njoy.

Miss Melissa -- I wish I could hold your head while you suck cock. And then watch you take it all the way up your ass.

smoothboi -- I'll keep at the dildo so I'm ready for you.

Miss Melissa -- Just keep trying. You'll get there if you want to. And I know you want to.

smoothboi -- Something to strive for.

Miss Melissa -- My sissy has been telling me to get a guy to clean for me for years.

smoothboi -- That's what I used to do. I'd do it for you no problem.

Miss Melissa -- I might want to get fucked after he cleans the house and you don't fuck women anymore.

smoothboi -- I want to fuck a man at least once.

Miss Melissa -- You should try it, for sure. To see the difference. I'd like to watch you be fucked while you fucked a man. I'd love to grab your ass and watch him push his cock inside of you. I've always wanted to do this. Have an uninhibited gayboi sub.

smoothboi -- We'd have to find the right men, but I could do that. Especially with you there.

Miss Melissa -- What type of top do you imagine when you think about getting fucked? What kind of man turns you on?

smoothboi -- Black men. But shaved all the way. Runner-athletic.

Miss Melissa -- Would you wear your chain?

smoothboi -- Oh, definitely.

Miss Melissa -- What about a collar? Do you have one?

smoothboi -- I do. I don't wear it much but I would.

Miss Melissa -- I know you'll be hard when he fucks you. Wonder what position we will have to put you in to make you cum from his cock, no hands? Sorry my mind went right to the fucking. You have to suck his cock first. I wonder how many inches you can take. Do you practice sucking big dildos?

smoothboi -- I suck the suction cup dildo before I fuck it.

Miss Melissa -- Would you consider short-term chastity?

smoothboi -- I probably would with you.

Miss Melissa -- Seeing a man get fucked while his cock is locked up is so hot. The way the precum just leaks out and his cock strains in the cage. It would look so gay to have your cock in a cage that matches your chain, and they could even be clipped together. What do you fantasize about the most when you think about the orgasm itself? Do you want to cum while being fucked? Do you want a reach-around? Do you want to be bred and then have him suck you off or jerk you off or he watches you jerk off?

smoothboi -- I definitely want to cum while being fucked and bred if possible.

Miss Melissa -- But would you want to cum from anal while caged? Your cock couldn't get fully hard.

smoothboi -- When I came from pegging I wasn't even hard, but I got really hard after I came.

Miss Melissa -- Oh that's pretty hot, to cum and not be hard.

smoothboi -- That's what started it all, really. I got myself to pre cum from the dildo.

Miss Melissa -- That's hot. Keep working at it.

smoothboi -- I can take the whole thing now.

Miss Melissa -- If you were ever out this way, I bet we could find someone for you.

smoothboi -- You're in a more populated area, so I would think so.

Miss Melissa -- So many more people. You want to get both ends fucked at once? You need to practice oral and deepthroating. And we have got to get you fucked. You're going to love it.

smoothboi -- I don't doubt it anymore. There's just always a reason to not pull the trigger I need to get over.

Miss Melissa -- What do you think you're afraid of? Are you afraid that once you finally give in completely to this, it will take over your life? I know how much of your time you spend on these gay thoughts and urges. Let's cross that line and make it real. I mean, this has been going on since the last woman you ever had sex with. You told her you were into cock and she pegged you and you've been on this path ever since.

smoothboi -- She didn't really look at me the same.

Miss Melissa -- Did you want her to though? You knew what you were becoming, what you are now. She was your experiment. Weren't you wishing she had a real cock to cum inside of you with? You need a man.

smoothboi -- I didn't like that she seemed disgusted with me, but I wanted to be humiliated.

Miss Melissa -- I just want you to know what it feels like to be fucked. There's nothing like it. Being fucked by a man with a cock that can cum inside of you. Then you'll be the town slut!

smoothboi -- Maybe not this town.

Miss Melissa -- I'd love if you took a gay vacation to see me. Why not? You got money now.

smoothboi -- Really?

Miss Melissa -- We're right near the train station to two big major cities. There's plenty to do like regular stuff.

smoothboi -- We get along great, so I'm sure we'll have fun.

Miss Melissa -- When the weather gets warmer, you can come here for a gaycation and we'll hang out. But no pretending to be hetero anymore. You won't know anyone and you can be free. But no pressure outside of that.

smoothboi -- Can we go to the nude beach too?

Miss Melissa -- Fuck yeah. The one here is all gay. So you could lay out and just enjoy being gay.

smoothboi -- That sounds really appealing.

Miss Melissa -- No pressure. If you want to get fucked, we'll get you fucked. And I'll be there to help you. If it doesn't work out, that's ok too.

smoothboi -- I should at least suck cock for real.

Miss Melissa -- Don't you want to cum with a real cock in your mouth? I think you'll like that.

smoothboi -- We can make that our goal.